20-Hydroxyeicosatetraenoic acid

37: 1421:. Among its many other effects, the drug caused these cells to decrease their levels of 20-HETE in vitro; the addition of 20-HETE to these cultures rescued the cells from apoptosis. Isoliquiritigenin also inhibits the in vivo lung metastasis of MDA-MB-231 cell transplants while concurrently decreasing the tumor's levels of 20-HETE. The growth of MDA-MB-231 cells implanted into athymic nude female mice as well as the cells' production of a large variety of agents stimulating vascularization including vascular endothelial growth factor were inhibited by treating the mice with an inhibitor of 20-HETE production. 1177:(Cyp4a14(-/-) mice develop male-specific, androgen-dependent hypertension. This seemingly paradoxical result is due to the overexpression of Cyp4a12a; the knockout of Cyp4a14 (Cyp4a14 does not produce 20-HETE) leads to the overexpression of the 20-HETE-producing cytochrome, Cyp4a149(-/-), and consequent overproduction of 20-HETE. The model involves increased plasma androgens, increased vascular and urinary levels of 20-HETE, relief of hypertension by castration, and hypertension which is driven by excessive fluid reabsorption in the kidney's proximal tubule secondary to the overexpression of 280: 1501:

prostaglandin and thromboxane products. In addition, 20-HETE itself blocks prostaglandin and thromboxane metabolites from interacting with the thromboxane receptor. Both effects, i.e. replacement of prostaglandin and thromboxane production with platelet-inactive products and thromboxane A2 receptor blockade, are responsible for 20-HETE's platelet aggregation-inhibiting action. However, the platelet anti-aggregating activity of 20-HETE requires micromolar levels and therefore may be more of a pharmacological than physiological activity.

1248:=2.31); 1538 males and females from the Framingham Heart Study (Odds ratio=1.23); males but not females in 732 black Americans with hypertensive renal disease participating in the African American Study of Kidney Disease; males in a sample of 507 individuals in Japan and in the third MONICA (MONitoring trends and determinants In Cardiovascular disease survey of 1397 individuals the homozygous C8590C genotype to the homozygous T8590T genotype with odds ratios of 3.31 for all subjects, 4.30 for males 2.93 for women); 1271:(adjusted odds ratio of 1.50 in comparing homozygous and heterozygous C296T subjects to homozygous C286C subjects) in >2000 individuals taken from the Han Chinese population. The effect of the −296C>T single base pair substitution on baseline CYP411 transcriptional activity was not significant, suggesting that this polymorphism may not be the causal variant but instead may be in linkage disequilibrium with the causal variant. Regardless, this SNP may serve as a 1436:-binding sites, including those for miR-211, miR-125a-3p, miR-197, miR-1226, and miR-204'. Since these miRNA's reduce the translation of CYP4Z1, the expression of CYP4Z2P can bind these miRNAs to reduce their interference with CYP4Z1 and thereby increase the production of CYP4Z1 protein and perhaps 20-HETE; indeed, force expression of these 3'UTRs promoted in vitro tumor angiogenesis in breast cancer cells partly via miRNA-dependent activation of the 1001:. While significantly less potent than thromboxane A2 in activating this receptor, studies on rat and human cerebral artery preparations indicate that increased blood flow through these arteries triggers production of 20-HETE which in turn binds to thromboxane receptors to constrict these vessels and thereby reduce their blood blow. Acting in the latter capacity, 20-HETE, it is proposed, functions as a mediator regulating blood flow to the brain. 1517:. While significantly less potent than thromboxane A2 in activating this receptor, studies on human cerebral artery preparations indicate that increased blood flow through these arteries triggers production of 20-HETE which in turn binds to thromboxane receptors to constrict these vessels and thereby reduce their blood blow. Acting in the latter capacity, 20-HETE, it is proposed, functions as a mediator regulating blood flow to the human brain. 838:

activities to their prostaglandin and thromboxane precursors and since the 12-hydroxy and 11-hydroxy metabolites of 20-HETE may also be inactive, these metabolic pathways appear to function in inactivating 20-HETE with respect to the platelet system. However, the 20-hydroxy prostaglandin metabolites are able to contract rat aorta rings and thereby could contribute to the hypertensive actions of 20-HETE.

940:, angiotensin II. 20-HETE has a particularly complex interaction with the renin angiotensin system: angiotensin II stimulates the preglomerular microvessels of the rat kidney to produce 20-HETE; this production is required for angiotensin II to exert its full constrictor effects; and 20-HETE induces transcription of the enzyme which converts angiotensin I to angiotensin II, i.e. 719:, respectively. While many of the effects and diseases associated with the over- or under-expression, pharmacological inhibition, and single nucleotide or mutant variants of the cytochrome ω-hydroxylases have been attributed to their impact on 20-HETE production, the influence of these alternate metabolic actions have frequently not been defined. 1193:(EETs). The model involves normal levels of 20-HETE, reduced expression of Cyp2c44, reduced levels of EETs, and deficiencies in kidney tubule absorption of sodium regulated by EETs, and the normalization of hypertensive blood pressure by increasing expression of Cyp2c44 by treating the mice with an inducer of its expression, an activator of 1149:

infused kidney, and produced a mean arterial pressure rise from 115 at baseline to 142 mm of mercury; this study indicates that the hypertensive versus hypotensive effects of 20-HETE depend not only on the organ of its production but also, with respect to the kidney, the site within the organ where it is produced.

1312:(i.e. ischemic stroke) in a study of 175 subjects with infarction compared to 246 control subjects in Japan, in 507 stroke patients compared to 487 age- and sex-matched 487 controls in India, and in males but not females in a study of 558 patients compared to 557 controls in China. The variant is associated with 890:

this organ and species. Coronary artery endothelial cells isolated from pigs incorporate 20-HETE primarily into the sn-2 position of phospholipids through a coenzyme A-dependent process. It is likely, although not yet shown, that these mouse and pig 20-HETE metabolizing pathways also occur in humans.

1148:

models) that had one kidney removed and then fed a high salt diet are hypertensive. Kidney medullary interstitial infusion of an inhibitor of 20-HETE production reduced the formation of 20-HETE in the outer medulla of the infused kidney, had no effect on the production of 20-HETE in the cortex of the

1103:

As indicated above, 20-HETE may raise blood pressure by constricting arterial blood vessels but also may lower blood pressure by promoting the loss of sodium and fluids in the kidneys. The effects of 20-HETE therefore are complex, as indicated in studies of the following animal models. Many of these

1486:

glioma cells in culture; since these cells could not be shown to produce 20-HETE, it was proposed that some other metabolite may by the inhibitor's targeted cytochrome enzymes was responsible for maintaining these cells growth. It is also possible that any such inhibitor has off-target effects that

480:

reaction. CYP450 enzymes belong to a superfamily which in humans is composed of at least 57 members and in mice at least 120 members. Among this superfamily, certain members of the CYP4A and CYP4F subfamilies in the CYP4 family are considered predominant cytochrome P450 enzymes that are responsible

1444:

and thereby stimulating the production of vascular endothelium growth factor and possibly other endothelium growth factors. Taken together, these pre-clinical studies suggest that 20-HETE made by one or more of the cited cytochrome P450 enzymes may contribute to the progression of breast cancer by

1227:

Human CYP4A11 has 72.69% amino acid identity with murine cyp4a14 and 73.02% identity with murine cyp4a10 suggesting that it plays a role in humans similar to that of cyp4a14 and/or cyp4a10 in mice. The association of hypertension with defective CYP4A11 in humans as indicated below seems to parallel

898:

20-HETE-synthesizing enzymes are widely distributed to liver, kidney, brain, lung, intestine and blood vessels. In most vascular systems, 20-HETE synthesizing activity is limited to vascular smooth muscle of small blood vessels with little or no such activity in the vessel's endothelial cells or in

1500:

to mediate and/or promote the ensuing platelet aggregation response to most stimuli. The platelets metabolize 20-HETE to the 20-hydroxy analogs of prostaglandin H2 and thromboxane A2, products that are essentially inactive in platelets, while consequently form less of the arachidonic acid-derived

1316:

in a study of 507 patients compared to 487 age- and sex-matched controls in India, in males but not females in a study of 234 patients compared to 248 control subjects in Japan, and in male but not female patients in Sweden enrolled in the cardiovascular cohort of the Malmo Diet and Cancer Study.

889:

reactions. These shortening pathways also are likely to serve in inactivating 20-HETE, although the initial product of this shortening pathway, 20-carboxy-HETE, dilates coronary microvessels in the pig heart and thereby could serve to antagonize the vasoconstrictor actions of 20-HETE, at least in

666:

inhibitors may act as perhaps unwanted side effects to increase the levels of 20-HETE. There are a variety of pharmacological agents which inhibit the synthesis of 20-HETE including various fatty acid analogs that compete reversibly with arachidonic acid for the substrate binding site in the CYP

543:

with the predominant 20-HETE-synthesizing enzymes being CYP4F2, which is the major 20-HETE producing enzyme in the human kidney, followed by CYP4A11. CYP4F3 is expressed as two distinct enzymes, CYP4F3A and CYP4F3B, due to alternative splicing of a single pre-mRNA precursor molecule; CYP4F3A is

1367:

dysfunction. A second homozygous enzyme-disabling mutation has been identified in CYP2U1, c.1A>C/p.Met1?, that is associated with <1% of hereditary spastic paraplegia sufferers. While the role of 20-HETE in these mutations has not been established, the reduction in 20-HETE production and

837:

of the hydroperoxy and hydroxyl residues at positions 11 and 12 in the eicosatetraenoic acids are predicted based on studies defining the chirality of the arachidonic metabolites made by these enzymes.) Since the prostaglandin and thromboxane metabolites of 20-HETE lack the platelet-stimulating

438:

including the regulation of vascular tone, blood flow to specific organs, sodium and fluid transport in the kidney, and vascular pathway remodeling. These vascular and kidney effects of 20-HETE have been shown to be responsible for regulating blood pressure and blood flow to specific organs in

1481:

While these studies suggest that CYP4A11, CYP4A22, CYP4F2, and/or CYP4F3 produce 20-HETE which in turn promotes the growth of the cited cancers in model systems and therefore may do so in the human cancers, this suggestion clearly needs much further study. For example, an inhibitor of 20-HETE

1304:

in comparing 249 patients with hypertension to 238 age-matched controls in Japan, the variant was not associated with hypertension. The maintenance of the lower blood pressure that followed diet-induced weight loss was more difficult for carriers of the Val433Met variant and may be related to

1251:

A study of 1501 participants recruited from the Tanno-Sobetsu Study found that the variant -845G in the promoter region of CYP411 (−845A is the predominant genotype) is associated with reduced transcription of CYP411 as well as with hypertension (odds ratio of homozygous and heterozygous -845G

1024:

rats that underwent balloon injury of the common carotid artery exhibited elevated levels of CYP4A enzyme immunostaining in the smooth muscle of the injured arteries as well as elevated levels of 20-HETE in the injured arteries. Inhibition of 20-HETE production by two different agents greatly

1477:

Messenger RNAs for CYP4A11, CYP4A22, CYP4F2, and/or CYP4F3 are more highly expressed in ovary, colon, thyroid, lung, ovary, cancers compared to their normal tissue counterparts; in ovarian cancer, this higher expression is associated with an increased level of CYP4F2 protein expression and an

1104:

models appear relevant to hypertension in humans in that they parallel the human disease, i.e. men have higher rates of hypertension than women, and women with increased levels of androgens (e.g. postmenopausal women and women with polycystic ovarian disease) and higher rates of hypertension.

568:

In mice, the only 20-HETE- and 19-HETE-producing enzymes of the Cyp4a subfamily are two extensively homologous ones, Cyp4a12a and Cyp4a12b; Cyp4a12a is expressed in the male kidney in an androgen hormone-dependent manner. In rats, Cyp4a1, Cyp4a2, Cyp4a3, and Cyp4a8 make 20-HETE. The tissue

556:, the only member of the human CYP2U subfamily, is highly expressed in brain and thymus and to lesser extents in numerous other tissues such as kidney, lung and heart. CYP2U1 protein is also highly expressed, compared to several other cytochrome P450 enzymes, in malignant breast tissue; the 1184:

Mice depleted of Cyp4a10 maintain normal blood pressure on a low salt diet but become hypertensive on normal or high salt diets; this paradoxical result appears due to a decrease in kidney levels of Cyp2C44 caused by the loss of Cyp4a10. Cyp2C44 metabolizes arachidonic acid a family of

1239:

rs1126742 variant of CYP4A11 switches thymidine to cytosine at nucleotide 8590 and leads to a phenylalanine-to-serine substitution at amino acid 434); this F434S variant has significantly reduced ability to ω-oxidize arachidonic acid to 20-HETE and has been associated with

1136:

that in turn stimulates the CYp4A/20-HETE pathway. Non-selective and non-selective inhibitors of CYP4A and 20-HETE production reduce hypertension in this model. The hypertension in this model is more severe in male rats and appears to be mediated at least in part by

1283:

The T allele at rs2108622, which has been designated as CYP4F2*3 in the Human CYP Allele Nomenclature Database by the Pharmacogene Variation Consortium, produces the CYP4F2 enzyme with methionine residue instead of valine at position 433 (the Val433Met variant), a

1004:

These vasoconstrictor effects of 20-HETE can reduce blood flow to specific parts of the body, not only to brain (see previous paragraph) but also to kidney, liver, heart and other organs, as well as to portions of these organs; they can also contribute to systemic

1461:

cell line U251 and, when forced to overexpress CYP4Z1 by gene transfection, overproduced 20-HETE and exhibited a dramatically increased rate of growth that was blocked by inhibiting the cells from producing 20-HETE. A similar set of findings was found with human

1029:

hyperplasia and vascular remodeling that occurred after balloon injury. The studies suggest that the increase in expression of CYP4A and production of 20-HETE contribute to vascular intima growth, remolding, and thereby healing of injured rat carotid arteries.

986:; this inhibits the ability of eNOS to become activated. The endothelial cells become dysfunctional in exhibiting decreased ability to produce the vasodilating agent, nitric oxide, and in containing elevated levels of a potentially injurious oxygen radical, 443:; genetic and preclinical studies suggest that 20-HETE may similarly regulate blood pressure and contribute to the development of stroke and heart attacks. Additionally the loss of its production appears to be one cause of the human neurological disease, 2194:

Thomas RD, Green MR, Wilson C, Weckle AL, Duanmu Z, Kocarek TA, et al. (2006). "Cytochrome P450 expression and metabolic activation of cooked food mutagen 2-amino-1-methyl-6-phenylimidazo4,5-bpyridine (PhIP) in MCF10A breast epithelial cells".

4977:

Tatarunas V, Jankauskiene L, Kupstyte N, Skipskis V, Gustiene O, Grybauskas P, et al. (2014). "The role of clinical parameters and of CYP2C19 G681 and CYP4F2 G1347A polymorphisms on platelet reactivity during dual antiplatelet therapy".

1495:

20-HETE inhibits the aggregation of human platelets by competing with arachidonic acid for the enzymes that produce prostaglandin H2 and thromboxane A2. These products are formed in response to platelet stimulation and then act through the

5206:

Li Y, Zhao H, Wang Y, Zheng H, Yu W, Chai H, et al. (2013). "Isoliquiritigenin induces growth inhibition and apoptosis through downregulating arachidonic acid metabolic network and the deactivation of PI3K/Akt in human breast cancer".

5021:

Kim WY, Lee SJ, Min J, Oh KS, Kim DH, Kim HS, et al. (2018). "Identification of novel CYP4F2 genetic variants exhibiting decreased catalytic activity in the conversion of arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE)".

5253:

Zheng H, Li Y, Wang Y, Zhao H, Zhang J, Chai H, et al. (2014). "Downregulation of COX-2 and CYP 4A signaling by isoliquiritigenin inhibits human breast cancer metastasis through preventing anoikis resistance, migration and invasion".

1288:(1347C>T; NM_001082.5:c.1297G>A; p. Val433Met; rs2108622). This variant of the CYP4F2 enzyme has reduced capacity to metabolize arachidonic acid to 20-HETE but increased urinary excretion of 20-HETE. Studies found that: 1169:

mice overexpressing Cyp4a12 develop androgen-independent hypertension that is associated with increased levels of 20-HETE; this hypertension is fully reversible by treatment with a Cyp4a selective inhibitor of 20-HETE production.

707:, vascular responses, and other reactions. This metabolism-induced inactivation may underlie the proposed roles of the cytochromes in dampening inflammatory responses and the reported associations of certain CYP4F2 and CYP4F3 3169:

Watzer B, Reinalter S, Seyberth HW, Schweer H (2000). "Determination of free and glucuronide conjugated 20-hydroxyarachidonic acid (20-HETE) in urine by gas chromatography/negative ion chemical ionization mass spectrometry".

1115:

exhibit elevated levels of CYP4A2 and 20-HETE; blockade of 20-HETE production lowers blood pressure in this model. The effect is particularly well seen in female rats: aging post-menopausal but not pre-menopausal female

3246:

Hill E, Murphy RC (May 1992). "Quantitation of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) produced by human polymorphonuclear leukocytes using electron capture ionization gas chromatography/mass spectrometry".

1868:"CYP4 enzymes as potential drug targets: Focus on enzyme multiplicity, inducers and inhibitors, and therapeutic modulation of 20-hydroxyeicosatetraenoic acid (20-HETE) synthase and fatty acid ω-hydroxylase activities" 7535: 6671: 6406: 2674:

Kikuta Y, Kusunose E, Sumimoto H, Mizukami Y, Takeshige K, Sakaki T, et al. (1998). "Purification and characterization of recombinant human neutrophil leukotriene B4 omega-hydroxylase (cytochrome P450 4F3)".

1317:

The incidence of cerebral and myocardial infarction in these studies appears to be independent of hypertension. (The platelets of individuals heterozygous or homozygous for the Val433Met variant exhibit increased

520:)-HETE, inhibits the action of 20-HETE on vascular endothelial cells. Based on studies analyzing the production of other HETEs by CYP enzymes, the production of 19-HETE by these enzymes may include both its 3358:

Zhang F, Wang MH, Wang JS, Zand B, Gopal VR, Falck JR, et al. (2004). "Transfection of CYP4A1 cDNA decreases diameter and increases responsiveness of gracilis muscle arterioles to constrictor stimuli".

1066:

which in turn stimulates the adhesion of platelets to the endothelial cells. The endothelial, platelet, and pro-clotting actions of 20-HETE may contribute to its ability to disrupt blood flood to tissues.

2112:

Toselli F, Booth Depaz IM, Worrall S, Etheridge N, Dodd PR, Wilce PA, et al. (2015). "Expression of CYP2E1 and CYP2U1 proteins in amygdala and prefrontal cortex: Influence of alcoholism and smoking".

5152:

Citterio A, Arnoldi A, Panzeri E, d'Angelo MG, Filosto M, Dilena R, et al. (2014). "Mutations in CYP2U1, DDHD2 and GBA2 genes are rare causes of complicated forms of hereditary spastic paraparesis".

3000:"Different catalytically competent arrangements of arachidonic acid within the cyclooxygenase active site of prostaglandin endoperoxide H synthase-1 lead to the formation of different oxygenated products" 5732:

Guo M, Roman RJ, Falck JR, Edwards PA, Scicli AG (2005). "Human U251 glioma cell proliferation is suppressed by HET0016 N-hydroxy-N'-(4-butyl-2-methylphenyl)formamidine, a selective inhibitor of CYP4A".

1336:

of CYP4F2 is associated with essential hypertension in men only in a study of 249 hypertensive versus 238 age-matched controls in Japan. The impact of this variant on CYP4F2 expression is not known.

5828: 5689:

Rieger MA, Ebner R, Bell DR, Kiessling A, Rohayem J, Schmitz M, et al. (2004). "Identification of a novel mammary-restricted cytochrome P450, CYP4Z1, with overexpression in breast carcinoma".

1296:

among a large number of Swedish patients enrolled and monitored over 10 years in the cardiovascular cohort of the Malmö Diet and Cancer Study only males with this variant exhibited hypertension;

4877: 1424:

Messenger RNAs not only for CYP4Z2 but also for CYP4A11, CYP4A22, CYP4F2, and CYP4F3 are more highly expressed in samples of human breast cancer tumors compared to normal breast tissue. The

1363:

as well as other cytochrome P450 proteins; the p.Asp314Val mutation is located in the enzyme's functional domain, is predicted to be damaging to the enzyme's activity, and is associated with

3282:

Tsai IJ, Croft KD, Puddey IB, Beilin LJ, Barden A (Apr 2011). "20-Hydroxyeicosatetraenoic acid synthesis is increased in human neutrophils and platelets by angiotensin II and endothelin-1".

5646:

Downie D, McFadyen MC, Rooney PH, Cruickshank ME, Parkin DE, Miller ID, et al. (2005). "Profiling cytochrome P450 expression in ovarian cancer: Identification of prognostic markers".

2077:

Devos A, Lino Cardenas CL, Glowacki F, Engels A, Lo-Guidice JM, Chevalier D, et al. (2010). "Genetic polymorphism of CYP2U1, a cytochrome P450 involved in fatty acids hydroxylation".

1132:) and ameliorated by low salt intake. In this model, rats exhibit an up-regulated CYP4A/20-HETE pathway within their cerebral vasculature and vascular endothelial cell overproduction of 576:

Mouse CYP2J9, rat CYP2J3, and sheep CYP2J metabolize arachidonic acid primarily to 19-HETE but also to smaller amounts of 20-HETE, and, in the case of the sheep enzyme, 18-HETE; human

4750:

Munshi A, Sharma V, Kaul S, Al-Hazzani A, Alshatwi AA, Shafi G, et al. (2012). "Association of 1347 G/A cytochrome P450 4F2 (CYP4F2) gene variant with hypertension and stroke".

924:

In various rodent models, 20-HETE, at low concentrations (<50 nanomolar), acts to constrict arteries by sensitizing (i.e. increasing) the contraction responses of these artery's

7296: 1478:

increased ability to metabolize arachidonic acid to 20-HETE. Ovarian cancers also overexpress CYP4Z1 mRNA protein; this overexpression is associated with a poorer disease outcome.

3126:

Ward NC, Rivera J, Hodgson J, Puddey IB, Beilin LJ, Falck JR, et al. (2004). "Urinary 20-hydroxyeicosatetraenoic acid is associated with endothelial dysfunction in humans".

1325:. This platelet hyper-responsiveness to epinephrine, particularly if also exhibited to other platelet-aggregating agents, could contribute to cerebral and coronary infarctions.) 3394:

Kaide J, Zhang F, Wei Y, Wang W, Gopal VR, Falck JR, et al. (2004). "Vascular CO counterbalances the sensitizing influence of 20-HETE on agonist-induced vasoconstriction".

1181:; these effects are presumed but not yet shown to be due to the overproduction of 20-HETE. The Cyp4a12-transgenic model (above) is referred to in support of this presumption. 1758:

Bylund J, Ericsson J, Oliw EH (1998). "Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS".

675:

The cytochrome ω-oxidases including those belonging to the CYP4A and CYP4F sub-families and CYPU21 hydroxylate not only arachidonic acid but also various shorter chain (e.g.

6060: 5821: 4258:

Imaoka S, Ogawa H, Kimura S, Gonzalez FJ (1993). "Complete cDNA sequence and cDNA-directed expression of CYP4A11, a fatty acid omega-hydroxylase expressed in human kidney".

1529:

exhibited significantly elevated levels of plasma and urinary 20-HETE compared to matched controls; women with the syndrome had particularly higher urinary 20-HETE levels.

1157:

Androgen treatment causes hypertension in normal male and female rats; this hypertensive response is greatly reduced by diverse inhibitors of Cyp4a and 20-HETE production.

1359:

in that it segregates with the disease at the homozygous state in two afflicted families. The mutation affects an amino acid (p.Asp316Val) highly conserved among CYP2U1

5776:

Tsai IJ, Croft KD, Mori TA, Falck JR, Beilin LJ, Puddey IB, et al. (2009). "20-HETE and F2-isoprostanes in the metabolic syndrome: The effect of weight reduction".

5109:

Wortmann SB, Espeel M, Almeida L, Reimer A, Bosboom D, Roels F, et al. (2015). "Inborn errors of metabolism in the biosynthesis and remodelling of phospholipids".

4413:

Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008). "A haplotype of the CYP4A11 gene associated with essential hypertension in Japanese men".

4942:

Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2009). "A haplotype of the CYP4F2 gene associated with myocardial infarction in Japanese men".

447:. Preclinical studies also suggest that the overproduction of 20-HETE may contribute to the progression of certain human cancers, particularly those of the breast. 5814: 1405:

mice show a greater increase in tumor weight and vascularity compared to control T47D cells; these increases are prevented by an inhibitor of 20-HETE production.

1292:

among 161 hypertensive and 74 normotensive subjects in Australia, the incidence of the Val433Met variant was significantly increased in the hypertensive subjects;

1974:

Corcos L, Lucas D, Le Jossic-Corcos C, Dréano Y, Simon B, Plée-Gautier E, et al. (2012). "Human cytochrome P450 4F3: Structure, functions, and prospects".

3439:"Dietary Omega-3 Polyunsaturated Fatty Acids Prevent Vascular Dysfunction and Attenuate Cytochrome P4501A1 Expression by 2,3,7,8-Tetrachlorodibenzo-P-Dioxin" 906:

and platelets and by the ascending tubule cells in the medulla as well the pre-glomerular arterioles and certain other localized areas of the rabbit kidney.

125: 5418:

Zheng L, Li X, Gu Y, Lv X, Xi T (2015). "The 3'UTR of the pseudogene CYP4Z2P promotes tumor angiogenesis in breast cancer by acting as a ceRNA for CYP4Z1".

7014: 6299: 6033: 3087:"Metabolism of 20-hydroxyeicosatetraenoic acid by cyclooxygenase. Formation and identification of novel endothelium-dependent vasoconstrictor metabolites" 7242: 2557:"Renal drug metabolism in humans: The potential for drug-endobiotic interactions involving cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT)" 310:

InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-

1209:, also known as the capsaicin receptor and the vanilloid receptor 1), and through this receptor, cultured dorsal root ganglion cells taken from mice. 4839:"The effect of a single nucleotide polymorphism of the CYP4F2 gene on blood pressure and 20-hydroxyeicosatetraenoic acid excretion after weight loss" 4838: 5358:"Gene expression profiling reveals new aspects of PIK3CA mutation in ERalpha-positive breast cancer: Major implication of the Wnt signaling pathway" 5299:"HET0016, a selective inhibitor of 20-HETE synthesis, decreases pro-angiogenic factors and inhibits growth of triple negative breast cancer in mice" 4627:"Hypertension, cardiovascular risk and polymorphisms in genes controlling the cytochrome P450 pathway of arachidonic acid: A sex-specific relation?" 899:

large blood vessels. However, both the smooth muscle and endothelial cells obtained from mouse brain microvasculature, produce 20-HETE in culture.

3643:

Wang J, Li H, He J, Li B, Bao Q, Zhang X, et al. (2015). "20-Hydroxyeicosatetraenoic acid involved in endothelial activation and thrombosis".

3596:"20-Hydroxyeicosatetraenoic acid inhibition attenuates balloon injury-induced neointima formation and vascular remodeling in rat carotid arteries" 6538: 2910:"Omega-oxidation of 20-hydroxyeicosatetraenoic acid (20-HETE) in cerebral microvascular smooth muscle and endothelium by alcohol dehydrogenase 4" 990:; the blood vessels to which these dysfunctional endothelial cells belong are less able to dilate in response to the vasodilator, acetylcholine. 17: 6543: 548:, which is expressed in a limited range of tissues such as human breast and ovary, may also metabolize arachidonic acid to 20-HETE while human 1723:, Narsimhaswamy D, Pritchard Jr KA, et al. (2008). "20-hydroxyeicosatetraenoic acid causes endothelial dysfunction via eNOS uncoupling". 1120:

exhibit highly significant falls in blood pressure when treated with non-selective or selective inhibitors of CYP-induced 20-HETE production.

7625: 7485: 6497: 6426: 2753:"Interactions between the dietary polyunsaturated fatty acid ratio and genetic factors determine susceptibility to pediatric Crohn's disease" 6676: 323: 7480: 7341: 6736: 6635: 6588: 6518: 4115:

Fidelis P, Wilson L, Thomas K, Villalobos M, Oyekan AO (2010). "Renal function and vasomotor activity in mice lacking the Cyp4a14 gene".

7585: 3319:"Structural identification of cytochrome P450-dependent arachidonate metabolites formed by rabbit medullary thick ascending limb cells" 3046:"A single nucleotide polymorphism in the CYP4F2 but not CYP4A11 gene is associated with increased 20-HETE excretion and blood pressure" 3729:"Roles played by 20-HETE, angiotensin II and endothelin in mediating the hypertension in aging female spontaneously hypertensive rats" 1347:(2024C>G P85A; 80 C>T A27V rs771576634; 139C>T R47C rs115517770) which may affect conversion of arachidonic acid to HETE-20. 841:

Cultured smooth muscle and endothelial cells from mouse brain microvasculature oxidize 20-HETE to its 20-carboxy analog, 20-carboxy- 5

7600: 5507:"Cytochrome P450 ω-hydroxylase promotes angiogenesis and metastasis by upregulation of VEGF and MMP-9 in non-small cell lung cancer" 3825:

Crofton JT, Ota M, Share L (1993). "Role of vasopressin, the renin-angiotensin system and sex in Dahl salt-sensitive hypertension".

224: 6578: 1386: 6817: 6789: 1471: 6456: 2151:

Murray GI, Patimalla S, Stewart KN, Miller ID, Heys SD (2010). "Profiling the expression of cytochrome P450 in breast cancer".

1639:"CYP2U1, a novel human thymus- and brain-specific cytochrome P450, catalyzes omega- and (omega-1)-hydroxylation of fatty acids" 1055: 643: 4662: 6843: 6809: 3547:"Impact of vascular thromboxane prostanoid receptor activation on hemostasis, thrombosis, oxidative stress, and inflammation" 2951:"Downregulation of human platelet reactivity by neutrophils. Participation of lipoxygenase derivatives and adhesive proteins" 1051: 187: 4209:"20-Hydroxyeicosatetraenoic acid (20-HETE) is a novel activator of transient receptor potential vanilloid 1 (TRPV1) channel" 1474:

cell lines in culture; the 20-HETE antagonist also inhibited the growth of 786-O cells transplanted into athymic nude mice.

956:. likewise stimulate 20-HETE production and have vasoconstrictive actions which are enhanced by 20-HETE. These circular or 5837: 1394: 7580: 6696: 6436: 1681:

Hardwick JP (2008). "Cytochrome P450 omega hydroxylase (CYP4) function in fatty acid metabolism and metabolic diseases".

1466:

cells. A selective inhibitor of 20-HETE synthesis and a 20-HETE antagonist reduced the growth of two human kidney cancer

1267:) variant of CYP4A11, C296T (cytosine to thymine at position 296), was associated with a significantly increased risk of 964: 5062:"Alteration of fatty-acid-metabolizing enzymes affects mitochondrial form and function in hereditary spastic paraplegia" 4499:"A polymorphism regulates CYP4A11 transcriptional activity and is associated with hypertension in a Japanese population" 2805:"Determination of major UDP-glucuronosyltransferase enzymes and their genotypes responsible for 20-HETE glucuronidation" 1368:

thereby 20-HETE's activation of the TRPV1 receptor in nerve tissues, it is hypothesized, may contribute to the disease.

4688:"The V433M variant of the CYP4F2 is associated with ischemic stroke in male Swedes beyond its effect on blood pressure" 4590:

Stec DE, Roman RJ, Flasch A, Rieder MJ (2007). "Functional polymorphism in human CYP4F2 decreases 20-HETE production".

4458:"Association of the T8590C polymorphism of CYP4A11 with hypertension in the MONICA Augsburg echocardiographic substudy" 1079:

in the epithelial cells of the proximal tubules of the kidney; the kinase then phosphorylates and thereby inhibits the

5556:"Down-regulation of 20-HETE synthesis and signaling inhibits renal adenocarcinoma cell proliferation and tumor growth" 469: 294: 2639:

Konkel A, Schunck WH (2011). "Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids".

552:, once considered as contributing to 20-HETE production, is now regarded as being metabolically inactive. Finally, 1178: 683:) fatty acids. They can also ω-hydroxylate and thereby reduce the activity of various fatty acid metabolites (e.g. 4295:"Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension" 2604:

Kroetz DL, Xu F (2005). "Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation".

2247:"Arachidonic acid monooxygenase: Genetic and biochemical approaches to physiological/pathophysiological relevance" 1550:

Kroetz DL, Xu F (2005). "Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation".

395: 7658: 1425: 1128:

Dahl salt-sensitive rats develop hypertension that develops more quickly and exacerbated by high intake of salt (

1088: 4160:"Salt-sensitive hypertension is associated with dysfunctional Cyp4a10 gene and kidney epithelial sodium channel" 3870:"Testosterone-dependent hypertension and upregulation of intrarenal angiotensinogen in Dahl salt-sensitive rats" 7545: 6966: 6961: 6411: 1340: 1329: 1285: 1260: 1117: 1112: 2782: 6946: 6941: 5888: 4798:"Haplotype-based case-control study of the human CYP4F2 gene and essential hypertension in Japanese subjects" 1356: 941: 444: 7654: 6931: 6492: 4068:"Increased renal proximal convoluted tubule transport contributes to hypertension in Cyp4a14 knockout mice" 3493:"Isolated human and rat cerebral arteries constrict to increases in flow: role of 20-HETE and TP receptors" 974:

Studies in rats also indicate that in vascular endothelial cells 20-HETE inhibits the association of the

731: 692: 639: 258: 1205:

20-HETE activates the mouse and human transient receptor potential cation channel subfamily V member 1 (

36: 1463: 1437: 1010: 734:(UGTs) is thought to be a primary pathway of 20-HETE elimination and thereby inactivation in humans. 708: 570: 275: 4704: 4311: 7046: 6956: 6951: 6936: 6753: 6253: 5883: 5878: 1401:-2. T47D cells that overexpress CYP4Z1 also overproduce 20-HETE and when transplanted into athymic 1190: 1050:-inducing agent, ferric chloride, in the common carotid and femoral arteries; companion studies on 937: 218: 638:

binding site of the 20-HETE producing cytochrome p450 enzymes. Drugs that are substrates for the

7237: 7019: 5597:"Targeting 20-HETE producing enzymes in cancer - rationale, pharmacology, and clinical potential" 5297:

Borin TF, Zuccari DA, Jardim-Perassi BV, Ferreira LC, Iskander AS, Varma NR, et al. (2014).

1133: 873:-octadecatetraenoic acid, and then to the further chain-shortened dicarboxylic acid, 16-carboxy-5 4543:"Association of common variants of CYP4A11 and CYP4F2 with stroke in the Han Chinese population" 600:

are particularly potent stimulators of this production. Other stimulators include the powerful

7540: 7387: 7104: 6976: 6882: 6248: 5893: 4699: 4306: 3960:"Androgen-sensitive hypertension associates with upregulated vascular CYP4A12-20-HETE synthase" 3868:

Yanes LL, Sartori-Valinotti JC, Iliescu R, Romero DG, Racusen LC, Zhang H, et al. (2009).

1241: 1059: 968: 4399: 4009:"Alterations in the regulation of androgen-sensitive Cyp 4a monooxygenases cause hypertension" 2617: 2022:"Increased expression of CYP4Z1 promotes tumor angiogenesis and growth in human breast cancer" 1563: 7678: 7215: 5356:

Cizkova M, Cizeron-Clairac G, Vacher S, Susini A, Andrieu C, Lidereau R, et al. (2010).

4387: 2856:"Biological activity and metabolism of 20-hydroxyeicosatetraenoic acid in the human platelet" 1313: 1084: 1063: 993:

20-HETE can also constrict rodent (and human) artery preparations by directly activating the

983: 979: 165: 3919:"Inhibition of renal outer medullary 20-HETE production produces hypertension in Lewis rats" 1355:

A mutation (c.947A>T) in CYP2U1 has been associated with a small number of patients with

7688: 7683: 7595: 7416: 7358: 7287: 7195: 7148: 6583: 6446: 6384: 6364: 6238: 5926: 5369: 5310: 5263: 5216: 4020: 2404:"Androgen-induced hypertension in angiotensinogen deficient mice: Role of 20-HETE and EETS" 2204: 2033: 1510: 1497: 1318: 1300:

among several hundred subjects in India, the variant was associated with hypertension; and

994: 680: 101: 49: 4837:

Ward NC, Croft KD, Puddey IB, Phillips M, Van Bockxmeer F, Beilin LJ, et al. (2014).

3778:"Role of the CYP4A/20-HETE pathway in vascular dysfunction of the Dahl salt-sensitive rat" 279: 8: 7500: 7420: 7362: 7320: 7262: 7030: 6209: 4642: 4344:

Gainer JV, Lipkowitz MS, Yu C, Waterman MR, Dawson EP, Capdevila JH, et al. (2008).

3044:

Ward NC, Tsai IJ, Barden A, Van Bockxmeer FM, Puddey IB, Hodgson JM, et al. (2008).

2415: 2367: 2262: 1823: 1309: 925: 91: 5789: 5373: 5314: 5267: 5220: 4024: 3205:

Kaduce TL, Fang X, Harmon SD, Oltman CL, Dellsperger KC, Teesch LM, et al. (2004).

2208: 2037: 145: 7381: 7247: 7042: 6988: 6553: 6227: 6119: 5905: 5852: 5758: 5714: 5671: 5623: 5596: 5572: 5555: 5531: 5506: 5482: 5465: 5443: 5392: 5357: 5333: 5298: 5188: 5134: 5086: 5061: 5003: 4903:"A haplotype of the CYP4F2 gene is associated with cerebral infarction in Japanese men" 4869: 4775: 4727: 4714: 4687: 4654: 4603: 4567: 4542: 4515: 4498: 4474: 4457: 4438: 4370: 4345: 4321: 4294: 4235: 4208: 4184: 4159: 4140: 4092: 4067: 3984: 3959: 3894: 3869: 3850: 3802: 3777: 3753: 3728: 3704: 3679: 3620: 3595: 3576: 3517: 3492: 3463: 3438: 3419: 3407: 3151: 3139: 3062: 3045: 2880: 2871: 2855: 2831: 2804: 2581: 2556: 2532: 2507: 2483: 2424: 2403: 2376: 2351: 2320: 2295: 2271: 2246: 2176: 2054: 2021: 1999: 1948: 1923: 1892: 1867: 1832: 1807: 1611: 1586: 1526: 1446: 712: 4497:

Sugimoto K, Akasaka H, Katsuya T, Node K, Fujisawa T, Shimaoka I, et al. (2008).

3335: 3318: 3103: 3086: 2975: 2950: 569:

distribution of these enzymes differs from those of humans making extrapolations from

481:

in most tissues for forming 20-HETE and, concurrently, smaller amounts of 19-hydroxy-5

7575: 7098: 6686: 6609: 6600: 6431: 6200: 6155: 6145: 6090: 6043: 5843: 5793: 5750: 5706: 5663: 5628: 5577: 5536: 5487: 5435: 5397: 5338: 5279: 5232: 5180: 5126: 5091: 5039: 4995: 4959: 4924: 4861: 4819: 4767: 4719: 4646: 4607: 4572: 4520: 4479: 4430: 4375: 4326: 4275: 4240: 4189: 4132: 4097: 4048: 4043: 4008: 3989: 3940: 3899: 3842: 3838: 3807: 3758: 3709: 3660: 3625: 3568: 3522: 3468: 3411: 3376: 3340: 3299: 3264: 3228: 3187: 3143: 3108: 3067: 3021: 2980: 2949:

Valles J, Santos MT, Marcus AJ, Safier LB, Broekman MJ, Islam N, et al. (1993).

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inhibit 20-HETE production; these non-pharmacological agents do so by binding to the

5762: 5675: 5447: 5192: 5138: 5060:

Tesson C, Nawara M, Salih MA, Rossignol R, Zaki MS, Al Balwi M, et al. (2012).

5007: 4779: 4686:

Fava C, Montagnana M, Almgren P, Rosberg L, Lippi G, Hedblad B, et al. (2008).

4442: 4293:

Gainer JV, Bellamine A, Dawson EP, Womble KE, Grant SW, Wang Y, et al. (2005).

4207:

Wen H, Östman J, Bubb KJ, Panayiotou C, Priestley JV, Baker MD, et al. (2012).

3854: 3580: 3207:"20-hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells" 967:

to promote the entry of ionic calcium into vascular smooth muscle cells through the

246: 7510: 7276: 7114: 6523: 6184: 5868: 5785: 5742: 5718: 5698: 5655: 5618: 5608: 5567: 5526: 5518: 5477: 5427: 5387: 5377: 5328: 5318: 5271: 5224: 5170: 5162: 5118: 5081: 5073: 5031: 4987: 4951: 4914: 4873: 4853: 4809: 4759: 4731: 4709: 4658: 4638: 4599: 4562: 4554: 4510: 4469: 4422: 4365: 4357: 4316: 4267: 4230: 4220: 4179: 4171: 4124: 4087: 4079: 4038: 4028: 3979: 3971: 3930: 3889: 3881: 3834: 3797: 3789: 3748: 3740: 3699: 3691: 3652: 3615: 3607: 3558: 3512: 3504: 3458: 3450: 3403: 3368: 3330: 3291: 3256: 3218: 3179: 3155: 3135: 3098: 3057: 3011: 2970: 2962: 2921: 2875: 2867: 2826: 2816: 2764: 2723: 2684: 2648: 2613: 2576: 2568: 2527: 2519: 2487: 2465: 2419: 2411: 2371: 2363: 2315: 2307: 2266: 2258: 2212: 2180: 2160: 2122: 2086: 2049: 2041: 2003: 1983: 1943: 1935: 1887: 1879: 1827: 1819: 1767: 1732: 1690: 1650: 1606: 1598: 1559: 1441: 1076: 987: 949: 893: 746: 613: 601: 473: 431: 346: 5702: 5659: 4144: 3423: 2908:

Collins XH, Harmon SD, Kaduce TL, Berst KB, Fang X, Moore SA, et al. (2005).

971:; the attendant rise in intracellular calcium triggers these muscles to contract. 596:

Many agents stimulate cells and tissues to produce 20-HETE in vitro and in vivo.

7630: 7550: 7353: 7346: 6748: 6741: 6681: 6593: 6461: 6416: 5963: 5873: 5382: 5323: 4991: 4857: 4558: 4426: 2769: 2751:

Costea I, Mack DR, Lemaitre RN, Israel D, Marcil V, Ahmad A, et al. (2014).

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Messina A, Nencioni S, Gervasi PG, Gotlinger KH, Schwartzman ML, Longo V (2010).

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Chuang SS, Helvig C, Taimi M, Ramshaw HA, Collop AH, Amad M, et al. (2004).

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Mayer B, Lieb W, Götz A, König IR, Aherrahrou Z, Thiemig A, et al. (2005).

3885: 3656: 3372: 3295: 2090: 1736: 7377: 7292: 7062: 6984: 6691: 6223: 6130: 6100: 5993: 5901: 5275: 5228: 5077: 3744: 3695: 2402:

Garcia V, Cheng J, Weidenhammer A, Ding Y, Wu CC, Zhang F, et al. (2015).

2045: 1514: 1445:

promoting its survival, growth, and vascular endothelial growth factor-induced

1272: 1145: 1021: 998: 953: 886: 754: 750: 742: 700: 617: 605: 505:

can metabolize arachidonic acid to 19-HETE while forming little or no 20-HETE.

389: 79:

20-HETE, 20-Hydroxy-5,8,11,14-eicosatetraenoic, 20-Hydroxyeicosatetraenoic acid

5522: 5431: 5166: 5122: 4763: 2311: 2216: 1694: 1602: 7672: 7610: 7590: 7185: 6900: 6731: 6711: 6441: 6329: 6140: 6013: 5930: 4901:

Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008).

4796:

Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008).

3958:

Wu CC, Mei S, Cheng J, Ding Y, Weidenhammer A, Garcia V, et al. (2013).

3678:

Yanes LL, Lima R, Moulana M, Romero DG, Yuan K, Ryan MJ, et al. (2011).

3594:

Orozco LD, Liu H, Perkins E, Johnson DA, Chen BB, Fan F, et al. (2013).

1720: 1229: 1174: 5746: 4271: 4225: 4128: 4007:

Holla VR, Adas F, Imig JD, Zhao X, Price Jr E, Olsen N, et al. (2001).

3935: 3918: 3611: 3454: 3016: 2999: 2728: 2711: 1042:

mouse laboratory model, 20-HETE pretreatment accelerates the development of

7490: 7306: 7266: 7199: 7189: 7180: 7175: 7118: 7076: 6666: 6451: 6360: 6273: 6085: 6080: 5983: 5797: 5754: 5710: 5667: 5632: 5581: 5540: 5491: 5439: 5401: 5342: 5283: 5236: 5184: 5130: 5095: 5043: 4999: 4963: 4928: 4865: 4823: 4814: 4797: 4771: 4723: 4650: 4611: 4576: 4524: 4483: 4434: 4379: 4361: 4330: 4244: 4193: 4158:

Nakagawa K, Holla VR, Wei Y, Wang WH, Gatica A, Wei S, et al. (2006).

4136: 4101: 4052: 4033: 3993: 3975: 3903: 3811: 3762: 3713: 3664: 3629: 3572: 3526: 3472: 3415: 3380: 3303: 3260: 3232: 3223: 3206: 3191: 3183: 3147: 3071: 3025: 2935: 2926: 2909: 2840: 2778: 2737: 2688: 2660: 2625: 2590: 2541: 2479: 2433: 2385: 2329: 2280: 2224: 2172: 2134: 2098: 2063: 1995: 1987: 1957: 1901: 1841: 1771: 1744: 1702: 1664: 1655: 1638: 1620: 1571: 1390: 1364: 1186: 1006: 975: 704: 623: 513: 5554:

Alexanian A, Rufanova VA, Miller B, Flasch A, Roman RJ, Sorokin A (2009).

4279: 3944: 3846: 3508: 3344: 3268: 3112: 2984: 2889: 2696: 1779: 7530: 7458: 7442: 7310: 7282: 7165: 7109: 7052: 7038: 6726: 6721: 6661: 6390: 6375: 6370: 6324: 6263: 6190: 6170: 6149: 6110: 5973: 5938: 5806: 4919: 4902: 2397: 2395: 2345: 2343: 2341: 2339: 1322: 1138: 929: 903: 817:-eicosatetraenoic acid which is also rapidly reduced to 12,20-dihydroxy-5 676: 651: 581: 560:

human breast cancer cell line express messenger RNA for this cytochrome.

2821: 2803:

Jarrar YB, Cha EY, Seo KA, Ghim JL, Kim HJ, Kim DH, et al. (2014).

2470: 2453: 1509:

20-HETE constricts human artery preparations by directly activating the

1308:

The Val433Met variant is also associated with an increased incidence of

1091:(TALH); these effects reduce the absorption of sodium and fluids in the 7520: 7411: 7326: 7316: 7272: 7256: 7252: 7143: 7009: 6877: 6860: 6758: 6604: 6532: 6528: 6475: 6421: 6380: 6205: 6195: 6180: 6048: 5958: 5613: 5175: 3793: 2126: 1429: 1410: 1245: 1166: 1047: 1043: 933: 631: 609: 427: 374: 177: 156: 6914: 6772: 6343: 4626: 4083: 3563: 3546: 2966: 2572: 2454:"Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system" 2392: 2336: 1587:"Cytochrome P450-derived eicosanoids: the neglected pathway in cancer" 7635: 7620: 7615: 7565: 7560: 7205: 7124: 7082: 7072: 6309: 6174: 4976: 4175: 2458:

Journal of Smooth Muscle Research = Nihon Heikatsukin Gakkai Kikanshi

1418: 1360: 1256: 945: 834: 738: 597: 465: 5851: 1806:

Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC (Jul 2015).

777:-eicosatetraenoic acid which is rapidly reduced to 11,20-dihydroxy-5 544:

mostly expressed in leukocytes, CYP4F3B mostly in the liver. Human

388:

Except where otherwise noted, data are given for materials in their

7570: 7555: 7524: 7514: 7504: 7494: 7475: 7463: 7432: 7427: 7391: 7302: 7155: 7094: 7066: 7056: 7034: 6716: 6701: 6625: 6563: 6548: 6508: 6314: 6289: 6242: 6233: 6160: 6126: 6070: 6065: 6027: 6023: 5997: 5987: 5977: 5967: 5953: 5911: 5505:

Yu W, Chen L, Yang YQ, Falck JR, Guo AM, Li Y, et al. (2011).

3867: 3545:

Capra V, Bäck M, Angiolillo DJ, Cattaneo M, Sakariassen KS (2014).

2752: 1397:

while under expressing message and protein for tissue inhibitor of

659: 508:

The production of 19-HETE with 20-HETE may be significant since 19(

207: 5355: 5296: 5151: 4346:"Association of a CYP4A11 variant and blood pressure in black men" 3437:

Wiest EF, Walsh-Wilcox MT, Rothe M, Schunck WH, Walker MK (2016).

2111: 1194: 124: 7605: 7470: 7436: 7405: 7369: 7227: 7209: 7129: 7086: 7026: 6994: 6804: 6705: 6656: 6629: 6621: 6568: 6502: 6318: 6294: 6215: 6164: 6053: 5916: 3084: 2710:

Curley CR, Monsuur AJ, Wapenaar MC, Rioux JD, Wijmenga C (2006).

2296:"Molecular cloning and enzymatic characterization of sheep CYP2J" 1973: 1264: 1092: 1039: 737:

There are several other pathways that metabolize 20-HETE. Human

696: 647: 585: 549: 532: 233: 4066:

Quigley R, Chakravarty S, Zhao X, Imig JD, Capdevila JH (2009).

3645:

American Journal of Physiology. Heart and Circulatory Physiology

3284:

American Journal of Physiology. Heart and Circulatory Physiology

2076: 2020:

Yu W, Chai H, Li Y, Zhao H, Xie X, Zheng H, et al. (2012).

1160: 960:

interactions may serve to perpetuate vasoconstrictor responses.

894:

Tissue distribution of 20-HETE-producing enzymes and/or activity

7397: 7373: 7331: 7231: 7159: 6998: 6980: 6838: 6799: 6794: 6572: 6558: 6303: 6219: 6114: 6105: 6095: 6074: 6037: 6008: 6003: 5942: 5934: 5920: 5897: 5645: 4541:

Ding H, Cui G, Zhang L, Xu Y, Bao X, Tu Y, et al. (2010).

2508:"Cytochrome P450 eicosanoids in hypertension and renal disease" 2293: 1458: 1402: 1333: 1026: 928:

to other contracting agents such as alpha adrenergic agonists,

688: 577: 553: 545: 540: 536: 502: 498: 440: 3168: 2673: 1924:"20-HETE and blood pressure regulation: Clinical implications" 1305:

increased arterial stiffness and increased 20-HETE synthesis.

7401: 7137: 7133: 7090: 7004: 6773: 6640: 6617: 6257: 6134: 6017: 5948: 5553: 5466:"20-HETE-producing enzymes are up-regulated in human cancers" 4114: 3436: 2641:

Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics

1584: 1467: 1457:

20-HETE stimulated the proliferation of cultured human brain

1433: 1414: 1206: 663: 655: 557: 501:

may also contribute to the production of these two HETEs and

136: 114: 4685: 2150: 1009:

as well as to the physiological and pathological effects of

263: 7336: 7170: 6915: 6861: 6822: 6513: 6476: 6344: 5463: 5108: 4292: 3544: 3043: 2401: 1805: 1483: 1382: 684: 635: 198: 5059: 4749: 4496: 4065: 3317:

Carroll MA, Sala A, Dunn CE, McGiff JC, Murphy RC (1991).

3085:

Schwartzman ML, Falck JR, Yadagiri P, Escalante B (1989).

2709: 563: 4343: 4257: 2712:"A functional candidate screen for coeliac disease genes" 1922:

Wu CC, Gupta T, Garcia V, Ding Y, Schwartzman ML (2014).

1585:

Panigrahy D, Kaipainen A, Greene ER, Huang S (Dec 2010).

1275:

for large vessel disease stroke risk in this population.

5688: 3726: 2948: 2907: 2750: 1636: 793:-eicosatetraenoic acid; they also metabolize it through 591: 7221: 5024:

Prostaglandins, Leukotrienes, and Essential Fatty Acids

4836: 4206: 3733:

AJP: Regulatory, Integrative and Comparative Physiology

3684:

AJP: Regulatory, Integrative and Comparative Physiology

3593: 3172:

Prostaglandins, Leukotrienes, and Essential Fatty Acids

3125: 2352:"The role of 20-HETE in androgen-mediated hypertension" 2193: 2079:

Prostaglandins, Leukotrienes, and Essential Fatty Acids

1075:

In animal models, 20-HETE stimulates the activation of

4624: 3677: 3491:

Toth P, Rozsa B, Springo Z, Doczi T, Koller A (2011).

3204: 2997: 2146: 2144: 1409:, a proposed drug for treating cancer, cause cultured 1152: 5735:

Journal of Pharmacology and Experimental Therapeutics

4589: 3600:

Journal of Pharmacology and Experimental Therapeutics

3490: 3316: 3281: 2853: 1123: 5838: 5731: 4157: 2554: 5464:Alexanian A, Miller B, Roman RJ, Sorokin A (2012). 4941: 4900: 4795: 4412: 2903: 2901: 2899: 2141: 1107: 1054:indicate that 20-HETE stimulates the activation of 186: 5775: 4455: 3775: 3727:Lima R, Yanes LL, Davis DD, Reckelhoff JF (2013). 2244: 1757: 4006: 3393: 3357: 1921: 1718: 7670: 5594: 3916: 2896: 2802: 670: 245: 5504: 5459: 5457: 5413: 5411: 5252: 5248: 5246: 5205: 5055: 5053: 4791: 4789: 4745: 4743: 4741: 4681: 4679: 4536: 4534: 4013:Proceedings of the National Academy of Sciences 3824: 3540: 3538: 3536: 3486: 3484: 3482: 3039: 3037: 3035: 2501: 2499: 2497: 2447: 2445: 2443: 2240: 2238: 2236: 2234: 2015: 2013: 1969: 1967: 1417:human breast cancer cells to die by triggering 1232:in mice (see above section on genetic models). 1141:, the renin-angiotensin system, and androgens. 642:(UGT) enzymes which metabolize 20-HETE such as 225:acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid 100: 4540: 3957: 3680:"Postmenopausal hypertension: Role of 20-HETE" 2512:Current Opinion in Nephrology and Hypertension 2505: 2115:Alcoholism: Clinical and Experimental Research 1917: 1915: 1913: 1911: 1861: 1859: 1857: 1855: 1853: 1851: 1714: 1712: 1676: 1674: 1632: 1630: 1393:overexpress messenger RNA for and overproduce 1189:-inducing and anti-hypertensive products, the 963:Again in rodent models, 20-HETE acts to block 909: 5822: 4625:Fava C, Ricci M, Melander O, Minuz P (2012). 4350:Journal of the American Society of Nephrology 3964:Journal of the American Society of Nephrology 3497:Journal of Cerebral Blood Flow and Metabolism 2638: 2349: 1801: 1799: 1797: 1795: 1793: 1791: 1789: 1578: 1545: 1543: 1541: 1161:Genetically engineered models of hypertension 5769: 5725: 5682: 5639: 5588: 5547: 5498: 5454: 5408: 5349: 5290: 5243: 5199: 5145: 5102: 5050: 5014: 4970: 4935: 4894: 4830: 4786: 4738: 4676: 4618: 4583: 4531: 4490: 4449: 4406: 4337: 4286: 4200: 4151: 4108: 4059: 4000: 3951: 3861: 3769: 3720: 3671: 3636: 3587: 3533: 3479: 3430: 3387: 3351: 3198: 3162: 3119: 3032: 2998:Thuresson ED, Lakkides KM, Smith WL (2000). 2991: 2796: 2744: 2703: 2632: 2606:Annual Review of Pharmacology and Toxicology 2597: 2548: 2494: 2440: 2287: 2231: 2187: 2105: 2070: 2019: 2010: 1964: 1552:Annual Review of Pharmacology and Toxicology 1482:production blocks the growth of human brain 1339:Researchers have identified at least 3 more 1332:rs1558139 guanine to cytosine variant in an 1252:genotype versus homozygous -845A was 1.42); 857:-eicosatetraenoic acid, then to 18-carboxy-5 497:-eicosatetraenoic acid (19-HETE). However, 5417: 5020: 4251: 3910: 3818: 3310: 3078: 2942: 2847: 2667: 2451: 1908: 1865: 1848: 1709: 1671: 1627: 1095:and thereby tend to reduce blood pressure. 919: 531:In humans, the CYP4 ω-hydroxylases include 70:)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid 5836: 5829: 5815: 4631:Prostaglandins & Other Lipid Mediators 3642: 3245: 2408:Prostaglandins & Other Lipid Mediators 2356:Prostaglandins & Other Lipid Mediators 2251:Prostaglandins & Other Lipid Mediators 1812:Prostaglandins & Other Lipid Mediators 1786: 1751: 1538: 1525:One study found that 30 patients with the 1033: 278: 164: 5622: 5612: 5571: 5530: 5481: 5391: 5381: 5332: 5322: 5174: 5085: 4918: 4813: 4713: 4703: 4566: 4514: 4473: 4369: 4320: 4310: 4234: 4224: 4183: 4091: 4042: 4032: 3983: 3934: 3893: 3801: 3752: 3703: 3619: 3562: 3516: 3462: 3334: 3239: 3222: 3102: 3061: 3015: 2974: 2925: 2879: 2854:Hill E, Fitzpatrick F, Murphy RC (1992). 2830: 2820: 2768: 2727: 2618:10.1146/annurev.pharmtox.45.120403.100045 2580: 2555:Knights KM, Rowland A, Miners JO (2013). 2531: 2469: 2423: 2375: 2319: 2270: 2053: 1947: 1891: 1831: 1654: 1610: 1564:10.1146/annurev.pharmtox.45.120403.100045 1228:the hypertension associated with Cyp4a14 2603: 2561:British Journal of Clinical Pharmacology 1680: 1549: 434:that has a wide range of effects on the 331:C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCO 2677:Archives of Biochemistry and Biophysics 2245:Capdevila JH, Wang W, Falck JR (2015). 1490: 1222: 885:-hexadecatrrenoic acid, in a series of 564:Production by rodents and other animals 455: 410:, also known as 20-HETE or 20-hydroxy-5 274: 223: 14: 7671: 5111:Journal of Inherited Metabolic Disease 5066:The American Journal of Human Genetics 3917:Stec DE, Mattson DL, Roman RJ (1997). 1278: 1056:Extracellular signal-regulated kinases 1052:human umbilical vein endothelial cells 1016: 745:(s) to form the 20-hydroxy analogs of 644:non-steroidal anti-inflammatory agents 6009:CS gas (2-chlorobenzal malononitrile) 5810: 3551:Journal of Thrombosis and Haemostasis 3361:AJP: Heart and Circulatory Physiology 1976:Drug Metabolism and Drug Interactions 1872:Current Topics in Medicinal Chemistry 1725:AJP: Heart and Circulatory Physiology 1520: 1046:and reduces blood flow caused by the 592:Factors regulating 20-HETE production 303:Key: NNDIXBJHNLFJJP-DTLRTWKJSA-N 144: 5511:Cancer Chemotherapy and Pharmacology 5420:Breast Cancer Research and Treatment 4980:Blood Coagulation & Fibrinolysis 4643:10.1016/j.prostaglandins.2011.11.007 2416:10.1016/j.prostaglandins.2014.12.001 2368:10.1016/j.prostaglandins.2011.06.006 2263:10.1016/j.prostaglandins.2015.05.004 1824:10.1016/j.prostaglandins.2015.03.002 1428:(3'UTRs) of the CYP4Z1 gene and its 1395:vascular endothelial growth factor A 1381:Two human breast cancer cell lines, 1244:in: 512 white males from Tennessee ( 965:Calcium-activated potassium channels 741:and other tissues metabolize it via 7581:N-(p-Amylcinnamoyl)anthranilic acid 6697:N-(p-Amylcinnamoyl)anthranilic acid 6437:N-(p-Amylcinnamoyl)anthranilic acid 5790:10.1016/j.freeradbiomed.2008.10.028 5256:Toxicology and Applied Pharmacology 5209:Toxicology and Applied Pharmacology 3776:Lukaszewicz KM, Lombard JH (2013). 3323:The Journal of Biological Chemistry 3091:The Journal of Biological Chemistry 3004:The Journal of Biological Chemistry 2026:Toxicology and Applied Pharmacology 1350: 1200: 1153:Androgen-induced hypertensive model 1070: 584:, metabolizing arachidonic acid to 236: 206: 24: 4715:10.1161/HYPERTENSIONAHA.108.114199 4604:10.1152/physiolgenomics.00003.2007 4516:10.1161/HYPERTENSIONAHA.108.114082 4475:10.1161/01.HYP.0000182658.04299.15 4322:10.1161/01.CIR.0000151309.82473.59 3408:10.1161/01.HYP.0000135658.57547.bb 3140:10.1161/01.CIR.0000136808.72912.D9 3063:10.1161/HYPERTENSIONAHA.107.104463 2872:10.1111/j.1476-5381.1992.tb14327.x 2716:European Journal of Human Genetics 2506:Fan F, Muroya Y, Roman RJ (2015). 1217: 1124:Salt-sensitive hypertension models 1087:and 70 pS K+ channel in the thick 470:Cytochrome P450 omega hydroxylases 25: 7700: 5778:Free Radical Biology and Medicine 4944:Molecular Genetics and Metabolism 4164:Journal of Clinical Investigation 4117:Experimental Biology and Medicine 2955:Journal of Clinical Investigation 1487:are responsible for its actions. 1083:and concurrently also blocks the 914: 667:enzymes and benzene-based drugs. 5470:Cancer Genomics & Proteomics 4907:American Journal of Hypertension 4852:(7): 1495–502, discussion 1502. 3839:10.1097/00004872-199310000-00005 2165:10.1111/j.1365-2559.2010.03606.x 1452: 1426:Three prime untranslated regions 1389:, made to overexpress CYP4Z1 by 1376: 1212: 1108:Spontaneously hypertensive model 573:to humans somewhat complicated. 358: 35: 30:20-Hydroxyeicosatetraenoic acid 5595:Alexanian A, Sorokin A (2013). 4883:from the original on 2019-10-01 4665:from the original on 2024-03-08 4213:Journal of Biological Chemistry 3275: 3211:Journal of Biological Chemistry 2914:Journal of Biological Chemistry 2860:British Journal of Pharmacology 2785:from the original on 2020-07-03 2197:Chemico-Biological Interactions 1643:Journal of Biological Chemistry 1341:single-nucleotide polymorphisms 1118:spontaneously hypertensive rats 1113:Spontaneously hypertensive rats 1098: 1089:Ascending limb of loop of Henle 978:-producing enzyme, endothelial 450: 408:20-Hydroxyeicosatetraenoic acid 392:(at 25 °C , 100 kPa). 18:20-hydroxyeicosatetraenoic acid 2350:Wu CC, Schwartzman ML (2011). 1504: 1330:Single-nucleotide polymorphism 1286:single-nucleotide polymorphism 1261:single-nucleotide polymorphism 833:-eicosatetraenoic acid. (The 426:-eicosatetraenoic acid, is an 364: 352: 13: 1: 7655:Receptor/signaling modulators 6004:CR gas (dibenzoxazepine; DBO) 5703:10.1158/0008-5472.can-03-0849 5660:10.1158/1078-0432.CCR-05-0466 4547:Pharmacogenetics and Genomics 3336:10.1016/S0021-9258(18)98897-6 3104:10.1016/S0021-9258(18)80115-6 2809:The Journal of Lipid Research 1808:"Vascular actions of 20-HETE" 1591:Cancer and Metastasis Reviews 1532: 1357:Hereditary spastic paraplegia 942:angiotensin-converting enzyme 902:20-HETE is produced by human 722: 671:Proviso on 20-HETE production 445:Hereditary spastic paraplegia 5383:10.1371/journal.pone.0015647 5324:10.1371/journal.pone.0116247 4992:10.1097/MBC.0000000000000053 4858:10.1097/HJH.0000000000000208 4559:10.1097/FPC.0b013e328336eefe 4427:10.1097/HJH.0b013e3282f2f10c 3249:Biological Mass Spectrometry 2770:10.1053/j.gastro.2013.12.034 2653:10.1016/j.bbapap.2010.09.009 2524:10.1097/MNH.0000000000000088 1940:10.1097/CRD.0b013e3182961659 1884:10.2174/15680266113139990110 1866:Edson KZ, Rettie AE (2013). 1179:Sodium–hydrogen antiporter 3 1173:Mice depleted of Cyp4a14 by 732:UDP-glucuronosyltransferases 679:) and/or longer chain (e.g. 7: 7283:Paracetamol (acetaminophen) 6191:Paracetamol (acetaminophen) 6061:Farnesyl thiosalicylic acid 5889:15-Deoxy-Δ-prostaglandin J2 5036:10.1016/j.plefa.2018.02.003 4956:10.1016/j.ymgme.2008.11.161 3886:10.1152/ajprenal.90389.2008 3657:10.1152/ajpheart.00802.2014 3373:10.1152/ajpheart.00627.2003 3296:10.1152/ajpheart.00733.2010 2452:Miyata N, Roman RJ (2005). 2091:10.1016/j.plefa.2010.06.005 1737:10.1152/ajpheart.01172.2007 1058:to cause ERK-dependent and 910:Vascular-related activities 693:5-oxo-eicosatetraenoic acid 640:UDP-glucuronosyltransferase 468:-bound ω-hydroxylases, the 10: 7705: 5276:10.1016/j.taap.2014.07.018 5229:10.1016/j.taap.2013.05.031 5078:10.1016/j.ajhg.2012.11.001 3745:10.1152/ajpregu.00380.2012 3696:10.1152/ajpregu.00387.2010 2046:10.1016/j.taap.2012.07.019 1464:non-small cell lung cancer 801:)-hydroperoxy-20-hydroxy-5 761:)-hydroperoxy-20-hydroxy-5 709:single nucleotide variants 7648: 7451: 6924: 6913: 6893: 6870: 6859: 6831: 6782: 6771: 6649: 6485: 6474: 6399: 6353: 6342: 6282: 5861: 5850: 5523:10.1007/s00280-010-1521-8 5432:10.1007/s10549-015-3298-2 5167:10.1007/s00415-013-7206-6 5123:10.1007/s10545-014-9759-7 4764:10.1007/s11033-011-0907-y 4752:Molecular Biology Reports 2312:10.3109/00498250903410590 2217:10.1016/j.cbi.2006.01.007 1719:Cheng J, Ou JS, Singh H, 1695:10.1016/j.bcp.2008.03.004 1603:10.1007/s10555-010-9264-x 1438:phosphoinositide 3-kinase 1432:, CYP4Z2P, share several 1371: 1191:Epoxyeicosatrienoic acids 512:)-HETE, although not its 386: 339: 319: 290: 84: 76: 48: 43: 34: 6268:Umbellularia californica 5648:Clinical Cancer Research 4633:(Submitted manuscript). 1683:Biochemical Pharmacology 944:. Other agents such as 938:renin angiotensin system 920:Blood vessel contraction 7238:N-Arachidonoyl dopamine 7020:Andrographis paniculata 5747:10.1124/jpet.105.088567 5601:OncoTargets and Therapy 4846:Journal of Hypertension 4415:Journal of Hypertension 4272:10.1089/dna.1993.12.893 4226:10.1074/jbc.M111.334896 4129:10.1258/ebm.2010.009233 3936:10.1161/01.HYP.29.1.315 3827:Journal of Hypertension 3612:10.1124/jpet.113.203844 3017:10.1074/jbc.275.12.8501 2729:10.1038/sj.ejhg.5201687 1760:Analytical Biochemistry 1134:reactive oxygen species 1034:Blood vessel thrombosis 7659:Ion channel modulators 7388:Tetrahydrocannabivarin 6883:Tripterygium wilfordii 6249:Tetrahydrocannabiorcol 4815:10.1291/hypres.31.1719 4592:Physiological Genomics 4362:10.1681/ASN.2008010063 4034:10.1073/pnas.081627898 3976:10.1681/ASN.2012070714 3443:Toxicological Sciences 3261:10.1002/bms.1200210505 3224:10.1074/jbc.M306849200 3184:10.1054/plef.2000.0138 2927:10.1074/jbc.M504055200 2689:10.1006/abbi.1998.0724 1988:10.1515/dmdi-2011-0037 1772:10.1006/abio.1998.2897 1656:10.1074/jbc.M311830200 1242:essential hypertension 1062:-dependent release of 1060:L-type calcium channel 969:L-type calcium channel 7216:Lysophosphatidic acid 4802:Hypertension Research 3874:AJP: Renal Physiology 3509:10.1038/jcbfm.2011.74 3455:10.1093/toxsci/kfw145 1314:myocardial infarction 1085:Na-K-Cl cotransporter 1064:von Willebrand factor 1025:reduced the vascular 984:heat shock protein 90 980:nitric oxide synthase 7596:Pregnenolone sulfate 7417:Euphorbia resinifera 7359:Euphorbia resinifera 7288:Phenylacetylrinvanil 7248:N-Oleoylethanolamide 7196:Homodihydrocapsaicin 6584:Pregnenolone sulfate 6447:Pregnenolone sulfate 6254:Thiopropanal S-oxide 6239:Tetrahydrocannabinol 5927:Allyl isothiocyanate 5155:Journal of Neurology 4920:10.1038/ajh.2008.276 4260:DNA and Cell Biology 1928:Cardiology in Review 1498:thromboxane receptor 1491:Platelet aggregation 1319:platelet aggregation 1223:CYP4A11 polymorphism 1011:thromboxane receptor 681:docosahexaenoic acid 456:Production in humans 50:Preferred IUPAC name 7501:Cannabigerolic acid 7263:Nordihydrocapsaicin 7224:(acidic conditions) 5560:Anticancer Research 5374:2010PLoSO...515647C 5315:2014PLoSO...9k6247B 5268:2014ToxAP.280...10Z 5221:2013ToxAP.272...37L 4025:2001PNAS...98.5211H 2822:10.1194/jlr.M051169 2471:10.1540/jsmr.41.175 2410:. 116–117: 124–30. 2209:2006CBI...160..204T 2038:2012ToxAP.264...73Y 1310:cerebral infarction 1279:CYP4F2 polymorphism 1017:Blood vessel injury 936:, and a product of 926:smooth muscle cells 382: g·mol 31: 7464:Vernonia tweediana 7043:African blue basil 7015:Bisandrographolide 6601:Steviol glycosides 6554:Hydroxycitronellal 6300:Dehydroligustilide 6120:Angelica acutiloba 6034:Dehydroligustilide 5614:10.2147/OTT.S31586 4398:has generic name ( 4072:Nephron Physiology 3794:10.1042/CS20120483 2127:10.1111/acer.12697 1527:metabolic syndrome 1521:Metabolic syndrome 1447:neovascularization 952:compounds such as 604:-inducing agents, 396:Infobox references 29: 7666: 7665: 7644: 7643: 7576:Meclofenamic acid 7382:melegueta peppers 7253:Nonivamide (PAVA) 6989:melegueta peppers 6909: 6908: 6855: 6854: 6767: 6766: 6687:Meclofenamic acid 6610:Stevia rebaudiana 6470: 6469: 6432:Meclofenamic acid 6338: 6337: 6228:melegueta peppers 6201:Phenacyl chloride 6156:N-Methylmaleimide 6146:Methyl salicylate 6091:Hydrogen peroxide 6044:Diallyl disulfide 5906:melegueta peppers 4084:10.1159/000235774 3929:(1 Pt 2): 315–9. 3564:10.1111/jth.12472 2967:10.1172/JCI116709 2573:10.1111/bcp.12086 1407:Isoliquiritigenin 1399:metalloproteinase 1237:gene polymorphism 958:positive feedback 580:, however, is an 476:to 20-HETE by an 404:Chemical compound 402: 401: 259:CompTox Dashboard 126:Interactive image 16:(Redirected from 7696: 7511:Cannabigerovarin 7243:N-Oleoyldopamine 7149:Euodia ruticarpa 7115:Dihydrocapsaicin 6922: 6921: 6918: 6868: 6867: 6864: 6780: 6779: 6776: 6524:Cooling Agent 10 6483: 6482: 6479: 6351: 6350: 6347: 5869:4-Hydroxynonenal 5859: 5858: 5855: 5840: 5831: 5824: 5817: 5808: 5807: 5802: 5801: 5773: 5767: 5766: 5729: 5723: 5722: 5686: 5680: 5679: 5643: 5637: 5636: 5626: 5616: 5592: 5586: 5585: 5575: 5551: 5545: 5544: 5534: 5502: 5496: 5495: 5485: 5461: 5452: 5451: 5415: 5406: 5405: 5395: 5385: 5353: 5347: 5346: 5336: 5326: 5294: 5288: 5287: 5250: 5241: 5240: 5203: 5197: 5196: 5178: 5149: 5143: 5142: 5106: 5100: 5099: 5089: 5057: 5048: 5047: 5018: 5012: 5011: 4974: 4968: 4967: 4939: 4933: 4932: 4922: 4898: 4892: 4891: 4889: 4888: 4882: 4843: 4834: 4828: 4827: 4817: 4793: 4784: 4783: 4747: 4736: 4735: 4717: 4707: 4683: 4674: 4673: 4671: 4670: 4622: 4616: 4615: 4587: 4581: 4580: 4570: 4538: 4529: 4528: 4518: 4494: 4488: 4487: 4477: 4453: 4447: 4446: 4410: 4404: 4403: 4397: 4393: 4391: 4383: 4373: 4341: 4335: 4334: 4324: 4314: 4290: 4284: 4283: 4255: 4249: 4248: 4238: 4228: 4219:(17): 13868–76. 4204: 4198: 4197: 4187: 4176:10.1172/JCI27546 4155: 4149: 4148: 4112: 4106: 4105: 4095: 4063: 4057: 4056: 4046: 4036: 4004: 3998: 3997: 3987: 3955: 3949: 3948: 3938: 3914: 3908: 3907: 3897: 3865: 3859: 3858: 3822: 3816: 3815: 3805: 3782:Clinical Science 3773: 3767: 3766: 3756: 3724: 3718: 3717: 3707: 3675: 3669: 3668: 3651:(11): H1359–67. 3640: 3634: 3633: 3623: 3591: 3585: 3584: 3566: 3542: 3531: 3530: 3520: 3503:(10): 2096–105. 3488: 3477: 3476: 3466: 3434: 3428: 3427: 3391: 3385: 3384: 3355: 3349: 3348: 3338: 3329:(19): 12306–12. 3314: 3308: 3307: 3290:(4): H1194–200. 3279: 3273: 3272: 3243: 3237: 3236: 3226: 3202: 3196: 3195: 3166: 3160: 3159: 3123: 3117: 3116: 3106: 3097:(20): 11658–62. 3082: 3076: 3075: 3065: 3041: 3030: 3029: 3019: 2995: 2989: 2988: 2978: 2946: 2940: 2939: 2929: 2920:(39): 33157–64. 2905: 2894: 2893: 2883: 2851: 2845: 2844: 2834: 2824: 2800: 2794: 2793: 2791: 2790: 2772: 2757:Gastroenterology 2748: 2742: 2741: 2731: 2707: 2701: 2700: 2671: 2665: 2664: 2636: 2630: 2629: 2601: 2595: 2594: 2584: 2552: 2546: 2545: 2535: 2503: 2492: 2491: 2473: 2449: 2438: 2437: 2427: 2399: 2390: 2389: 2379: 2347: 2334: 2333: 2323: 2291: 2285: 2284: 2274: 2242: 2229: 2228: 2191: 2185: 2184: 2148: 2139: 2138: 2109: 2103: 2102: 2074: 2068: 2067: 2057: 2017: 2008: 2007: 1971: 1962: 1961: 1951: 1919: 1906: 1905: 1895: 1863: 1846: 1845: 1835: 1803: 1784: 1783: 1755: 1749: 1748: 1716: 1707: 1706: 1678: 1669: 1668: 1658: 1634: 1625: 1624: 1614: 1582: 1576: 1575: 1547: 1442:MAPK/ERK pathway 1351:CYP2U1 mutations 1201:Other activities 1144:Lewis rats (see 1077:protein kinase C 1071:Renal absorption 988:superoxide anion 950:alpha adrenergic 747:prostaglandin G2 703:) that regulate 616:compounds (e.g. 614:alpha adrenergic 602:vasoconstriction 474:arachidonic acid 432:arachidonic acid 381: 366: 360: 354: 347:Chemical formula 283: 282: 267: 265: 249: 238: 227: 210: 190: 168: 148: 128: 104: 39: 32: 28: 21: 7704: 7703: 7699: 7698: 7697: 7695: 7694: 7693: 7669: 7668: 7667: 7662: 7640: 7631:Tolfenamic acid 7551:Flufenamic acid 7447: 7354:Resiniferatoxin 7347:Ruta graveolens 7110:Diacyl glycerol 6905: 6889: 6851: 6847: 6827: 6813: 6763: 6749:Tolfenamic acid 6742:Ruta graveolens 6682:Flufenamic acid 6645: 6594:Ruta graveolens 6505:(intracellular) 6466: 6462:Tolfenamic acid 6417:Flufenamic acid 6395: 6371:Diacyl glycerol 6334: 6278: 5964:Cannabichromene 5874:4-Oxo-2-nonenal 5846: 5835: 5805: 5774: 5770: 5730: 5726: 5691:Cancer Research 5687: 5683: 5654:(20): 7369–75. 5644: 5640: 5593: 5589: 5566:(10): 3819–24. 5552: 5548: 5503: 5499: 5462: 5455: 5416: 5409: 5354: 5350: 5309:(12): e116247. 5295: 5291: 5251: 5244: 5204: 5200: 5150: 5146: 5107: 5103: 5058: 5051: 5019: 5015: 4975: 4971: 4940: 4936: 4913:(11): 1216–23. 4899: 4895: 4886: 4884: 4880: 4841: 4835: 4831: 4794: 4787: 4748: 4739: 4705:10.1.1.541.9456 4684: 4677: 4668: 4666: 4623: 4619: 4588: 4584: 4539: 4532: 4495: 4491: 4454: 4450: 4411: 4407: 4395: 4394: 4385: 4384: 4342: 4338: 4312:10.1.1.335.1764 4291: 4287: 4256: 4252: 4205: 4201: 4170:(6): 1696–702. 4156: 4152: 4123:(11): 1365–74. 4113: 4109: 4064: 4060: 4005: 4001: 3956: 3952: 3915: 3911: 3866: 3862: 3823: 3819: 3788:(12): 695–700. 3774: 3770: 3725: 3721: 3676: 3672: 3641: 3637: 3592: 3588: 3543: 3534: 3489: 3480: 3435: 3431: 3392: 3388: 3367:(3): H1089–95. 3356: 3352: 3315: 3311: 3280: 3276: 3244: 3240: 3203: 3199: 3167: 3163: 3124: 3120: 3083: 3079: 3042: 3033: 2996: 2992: 2947: 2943: 2906: 2897: 2852: 2848: 2815:(11): 2334–42. 2801: 2797: 2788: 2786: 2749: 2745: 2722:(11): 1215–22. 2708: 2704: 2672: 2668: 2637: 2633: 2602: 2598: 2553: 2549: 2504: 2495: 2450: 2441: 2400: 2393: 2348: 2337: 2292: 2288: 2243: 2232: 2192: 2188: 2149: 2142: 2110: 2106: 2075: 2071: 2018: 2011: 1972: 1965: 1920: 1909: 1878:(12): 1429–40. 1864: 1849: 1804: 1787: 1756: 1752: 1731:(2): H1018–26. 1717: 1710: 1689:(12): 2263–75. 1679: 1672: 1635: 1628: 1583: 1579: 1548: 1539: 1535: 1523: 1507: 1493: 1455: 1379: 1374: 1353: 1281: 1269:ischemic stroke 1225: 1220: 1218:Genetic studies 1215: 1203: 1163: 1155: 1130:sodium chloride 1126: 1110: 1101: 1073: 1036: 1019: 1013:-activation . 922: 917: 912: 896: 795:12-lipoxygenase 728:Glucuronidation 725: 717:Coeliac disease 713:Krohn's disease 673: 628:carbon monoxide 594: 566: 528:stereoisomers. 478:omega oxidation 462:Cytochrome P450 458: 453: 436:vascular system 405: 398: 393: 379: 369: 363: 357: 349: 335: 332: 327: 326: 315: 312: 311: 305: 304: 298: 297: 286: 276:DTXSID601009895 268: 261: 252: 239: 213: 193: 180: 171: 151: 131: 118: 107: 94: 80: 72: 71: 23: 22: 15: 12: 11: 5: 7702: 7692: 7691: 7686: 7681: 7664: 7663: 7649: 7646: 7645: 7642: 7641: 7639: 7638: 7633: 7628: 7623: 7618: 7613: 7608: 7603: 7598: 7593: 7588: 7583: 7578: 7573: 7568: 7563: 7558: 7553: 7548: 7543: 7538: 7533: 7528: 7518: 7508: 7498: 7488: 7483: 7478: 7473: 7468: 7455: 7453: 7449: 7448: 7446: 7445: 7440: 7430: 7425: 7409: 7395: 7385: 7367: 7351: 7339: 7334: 7329: 7324: 7321:Dorrigo pepper 7314: 7300: 7293:Phorbol esters 7290: 7285: 7280: 7270: 7260: 7250: 7245: 7240: 7235: 7225: 7218: 7213: 7203: 7193: 7183: 7178: 7173: 7168: 7163: 7153: 7141: 7127: 7122: 7112: 7107: 7102: 7080: 7070: 7063:Cannabidivarin 7060: 7050: 7031:camphor laurel 7024: 7012: 7007: 7002: 6992: 6974: 6969: 6964: 6959: 6954: 6949: 6944: 6939: 6934: 6928: 6926: 6919: 6911: 6910: 6907: 6906: 6904: 6903: 6897: 6895: 6891: 6890: 6888: 6887: 6874: 6872: 6865: 6857: 6856: 6853: 6852: 6850: 6849: 6845: 6841: 6835: 6833: 6829: 6828: 6826: 6825: 6820: 6815: 6811: 6807: 6802: 6797: 6792: 6786: 6784: 6777: 6769: 6768: 6765: 6764: 6762: 6761: 6756: 6751: 6746: 6734: 6729: 6724: 6719: 6714: 6709: 6699: 6694: 6692:Mefenamic acid 6689: 6684: 6679: 6674: 6669: 6664: 6659: 6653: 6651: 6647: 6646: 6644: 6643: 6638: 6633: 6614: 6598: 6586: 6581: 6576: 6566: 6561: 6556: 6551: 6546: 6541: 6536: 6526: 6521: 6516: 6511: 6506: 6500: 6495: 6489: 6487: 6480: 6472: 6471: 6468: 6467: 6465: 6464: 6459: 6454: 6449: 6444: 6439: 6434: 6429: 6424: 6419: 6414: 6409: 6403: 6401: 6397: 6396: 6394: 6393: 6388: 6385:St John's wort 6378: 6373: 6368: 6365:St John's wort 6357: 6355: 6348: 6340: 6339: 6336: 6335: 6333: 6332: 6327: 6322: 6312: 6307: 6297: 6292: 6286: 6284: 6280: 6279: 6277: 6276: 6271: 6261: 6251: 6246: 6236: 6231: 6213: 6210:Dorrigo pepper 6203: 6198: 6193: 6188: 6178: 6168: 6158: 6153: 6143: 6138: 6131:Sichuan pepper 6124: 6108: 6103: 6101:Isothiocyanate 6098: 6093: 6088: 6083: 6078: 6068: 6063: 6058: 6046: 6041: 6031: 6021: 6011: 6006: 6001: 5994:Cinnamaldehyde 5991: 5981: 5971: 5961: 5956: 5951: 5946: 5924: 5914: 5909: 5891: 5886: 5881: 5876: 5871: 5865: 5863: 5856: 5848: 5847: 5834: 5833: 5826: 5819: 5811: 5804: 5803: 5768: 5724: 5697:(7): 2357–64. 5681: 5638: 5587: 5546: 5497: 5453: 5407: 5368:(12): e15647. 5348: 5289: 5242: 5198: 5144: 5101: 5072:(6): 1051–64. 5049: 5013: 4969: 4934: 4893: 4829: 4808:(9): 1719–26. 4785: 4758:(2): 1677–82. 4737: 4675: 4637:(3–4): 75–85. 4617: 4582: 4530: 4489: 4448: 4405: 4356:(8): 1606–12. 4336: 4285: 4250: 4199: 4150: 4107: 4058: 3999: 3970:(8): 1288–96. 3950: 3909: 3860: 3833:(10): 1031–8. 3817: 3768: 3739:(3): R248–51. 3719: 3690:(6): R1543–8. 3670: 3635: 3586: 3532: 3478: 3429: 3386: 3350: 3309: 3274: 3238: 3217:(4): 2648–56. 3197: 3161: 3118: 3077: 3031: 3010:(12): 8501–7. 2990: 2961:(3): 1357–65. 2941: 2895: 2846: 2795: 2743: 2702: 2666: 2631: 2596: 2567:(4): 587–602. 2547: 2493: 2439: 2391: 2362:(1–4): 45–53. 2335: 2286: 2230: 2186: 2153:Histopathology 2140: 2104: 2069: 2009: 1963: 1907: 1847: 1785: 1750: 1708: 1670: 1649:(8): 6305–14. 1626: 1577: 1536: 1534: 1531: 1522: 1519: 1515:thromboxane A2 1506: 1503: 1492: 1489: 1454: 1451: 1378: 1375: 1373: 1370: 1352: 1349: 1280: 1277: 1273:genetic marker 1224: 1221: 1219: 1216: 1214: 1211: 1202: 1199: 1162: 1159: 1154: 1151: 1146:Laboratory rat 1125: 1122: 1109: 1106: 1100: 1097: 1072: 1069: 1035: 1032: 1022:Sprague Dawley 1018: 1015: 999:thromboxane A2 954:norepinephrine 921: 918: 916: 915:Rodent studies 913: 911: 908: 895: 892: 887:Beta oxidation 755:thromboxane B2 751:thromboxane A2 743:cyclooxygenase 730:of 20-HETE by 724: 721: 701:prostaglandins 699:, and several 672: 669: 662:, and various 618:norepinephrine 606:angiotensin II 593: 590: 571:rodent studies 565: 562: 457: 454: 452: 449: 430:metabolite of 403: 400: 399: 394: 390:standard state 387: 384: 383: 377: 371: 370: 367: 361: 355: 350: 345: 342: 341: 337: 336: 334: 333: 330: 322: 321: 320: 317: 316: 314: 313: 309: 308: 306: 302: 301: 293: 292: 291: 288: 287: 285: 284: 271: 269: 257: 254: 253: 251: 250: 242: 240: 232: 229: 228: 221: 215: 214: 212: 211: 203: 201: 195: 194: 192: 191: 183: 181: 176: 173: 172: 170: 169: 161: 159: 153: 152: 150: 149: 141: 139: 133: 132: 130: 129: 121: 119: 112: 109: 108: 106: 105: 97: 95: 90: 87: 86: 82: 81: 78: 74: 73: 53: 52: 46: 45: 41: 40: 9: 6: 4: 3: 2: 7701: 7690: 7687: 7685: 7682: 7680: 7677: 7676: 7674: 7661: 7660: 7656: 7653: 7647: 7637: 7634: 7632: 7629: 7627: 7624: 7622: 7619: 7617: 7614: 7612: 7611:Ruthenium red 7609: 7607: 7604: 7602: 7599: 7597: 7594: 7592: 7591:Niflumic acid 7589: 7587: 7584: 7582: 7579: 7577: 7574: 7572: 7569: 7567: 7564: 7562: 7559: 7557: 7554: 7552: 7549: 7547: 7544: 7542: 7539: 7537: 7534: 7532: 7529: 7526: 7522: 7519: 7516: 7512: 7509: 7506: 7502: 7499: 7496: 7492: 7489: 7487: 7484: 7482: 7479: 7477: 7474: 7472: 7469: 7466: 7465: 7460: 7459:α-Spinasterol 7457: 7456: 7454: 7450: 7444: 7441: 7438: 7434: 7431: 7429: 7426: 7423: 7422: 7418: 7413: 7410: 7407: 7403: 7399: 7396: 7393: 7389: 7386: 7383: 7379: 7375: 7371: 7368: 7365: 7364: 7360: 7355: 7352: 7349: 7348: 7343: 7340: 7338: 7335: 7333: 7330: 7328: 7325: 7322: 7318: 7315: 7312: 7308: 7304: 7301: 7298: 7294: 7291: 7289: 7286: 7284: 7281: 7278: 7274: 7271: 7268: 7264: 7261: 7258: 7254: 7251: 7249: 7246: 7244: 7241: 7239: 7236: 7233: 7229: 7226: 7223: 7219: 7217: 7214: 7211: 7207: 7204: 7201: 7197: 7194: 7191: 7187: 7186:Homocapsaicin 7184: 7182: 7179: 7177: 7174: 7172: 7169: 7167: 7164: 7161: 7157: 7154: 7151: 7150: 7145: 7142: 7139: 7135: 7131: 7128: 7126: 7123: 7120: 7116: 7113: 7111: 7108: 7106: 7103: 7100: 7099:wild bergamot 7096: 7092: 7088: 7084: 7081: 7078: 7074: 7071: 7068: 7064: 7061: 7058: 7054: 7051: 7048: 7047:camphor basil 7044: 7040: 7036: 7032: 7028: 7025: 7022: 7021: 7016: 7013: 7011: 7008: 7006: 7003: 7000: 6996: 6993: 6990: 6986: 6982: 6978: 6975: 6973: 6970: 6968: 6965: 6963: 6960: 6958: 6955: 6953: 6950: 6948: 6945: 6943: 6940: 6938: 6935: 6933: 6930: 6929: 6927: 6923: 6920: 6917: 6912: 6902: 6901:Ruthenium red 6899: 6898: 6896: 6892: 6885: 6884: 6879: 6876: 6875: 6873: 6869: 6866: 6863: 6858: 6848: 6842: 6840: 6837: 6836: 6834: 6830: 6824: 6821: 6819: 6816: 6814: 6808: 6806: 6803: 6801: 6798: 6796: 6793: 6791: 6788: 6787: 6785: 6781: 6778: 6775: 6770: 6760: 6757: 6755: 6752: 6750: 6747: 6744: 6743: 6738: 6735: 6733: 6732:Ruthenium red 6730: 6728: 6725: 6723: 6720: 6718: 6715: 6713: 6712:Niflumic acid 6710: 6707: 6703: 6700: 6698: 6695: 6693: 6690: 6688: 6685: 6683: 6680: 6678: 6675: 6673: 6670: 6668: 6665: 6663: 6660: 6658: 6655: 6654: 6652: 6648: 6642: 6639: 6637: 6634: 6632:; indirectly) 6631: 6627: 6623: 6619: 6615: 6612: 6611: 6606: 6602: 6599: 6596: 6595: 6590: 6587: 6585: 6582: 6580: 6577: 6574: 6570: 6567: 6565: 6562: 6560: 6557: 6555: 6552: 6550: 6547: 6545: 6542: 6540: 6539:Frescolat MGA 6537: 6534: 6530: 6527: 6525: 6522: 6520: 6517: 6515: 6512: 6510: 6507: 6504: 6501: 6499: 6496: 6494: 6491: 6490: 6488: 6484: 6481: 6478: 6473: 6463: 6460: 6458: 6455: 6453: 6450: 6448: 6445: 6443: 6442:Niflumic acid 6440: 6438: 6435: 6433: 6430: 6428: 6425: 6423: 6420: 6418: 6415: 6413: 6410: 6408: 6405: 6404: 6402: 6398: 6392: 6389: 6386: 6382: 6379: 6377: 6374: 6372: 6369: 6366: 6362: 6359: 6358: 6356: 6352: 6349: 6346: 6341: 6331: 6330:Ruthenium red 6328: 6326: 6323: 6320: 6316: 6313: 6311: 6308: 6305: 6301: 6298: 6296: 6293: 6291: 6288: 6287: 6285: 6281: 6275: 6272: 6269: 6265: 6262: 6259: 6255: 6252: 6250: 6247: 6244: 6240: 6237: 6235: 6232: 6229: 6225: 6221: 6217: 6214: 6211: 6207: 6204: 6202: 6199: 6197: 6194: 6192: 6189: 6186: 6182: 6179: 6176: 6172: 6169: 6166: 6162: 6159: 6157: 6154: 6151: 6147: 6144: 6142: 6141:Methylglyoxal 6139: 6136: 6132: 6128: 6125: 6122: 6121: 6116: 6112: 6109: 6107: 6104: 6102: 6099: 6097: 6094: 6092: 6089: 6087: 6084: 6082: 6079: 6076: 6072: 6069: 6067: 6064: 6062: 6059: 6056: 6055: 6050: 6047: 6045: 6042: 6039: 6035: 6032: 6029: 6025: 6022: 6019: 6015: 6014:Cuminaldehyde 6012: 6010: 6007: 6005: 6002: 5999: 5995: 5992: 5989: 5985: 5982: 5979: 5975: 5972: 5969: 5965: 5962: 5960: 5957: 5955: 5952: 5950: 5947: 5944: 5940: 5936: 5932: 5928: 5925: 5922: 5918: 5915: 5913: 5910: 5907: 5903: 5899: 5895: 5892: 5890: 5887: 5885: 5882: 5880: 5877: 5875: 5872: 5870: 5867: 5866: 5864: 5860: 5857: 5854: 5849: 5845: 5842: 5832: 5827: 5825: 5820: 5818: 5813: 5812: 5809: 5799: 5795: 5791: 5787: 5784:(2): 263–70. 5783: 5779: 5772: 5764: 5760: 5756: 5752: 5748: 5744: 5741:(2): 526–33. 5740: 5736: 5728: 5720: 5716: 5712: 5708: 5704: 5700: 5696: 5692: 5685: 5677: 5673: 5669: 5665: 5661: 5657: 5653: 5649: 5642: 5634: 5630: 5625: 5620: 5615: 5610: 5606: 5602: 5598: 5591: 5583: 5579: 5574: 5569: 5565: 5561: 5557: 5550: 5542: 5538: 5533: 5528: 5524: 5520: 5517:(3): 619–29. 5516: 5512: 5508: 5501: 5493: 5489: 5484: 5479: 5475: 5471: 5467: 5460: 5458: 5449: 5445: 5441: 5437: 5433: 5429: 5426:(1): 105–18. 5425: 5421: 5414: 5412: 5403: 5399: 5394: 5389: 5384: 5379: 5375: 5371: 5367: 5363: 5359: 5352: 5344: 5340: 5335: 5330: 5325: 5320: 5316: 5312: 5308: 5304: 5300: 5293: 5285: 5281: 5277: 5273: 5269: 5265: 5261: 5257: 5249: 5247: 5238: 5234: 5230: 5226: 5222: 5218: 5214: 5210: 5202: 5194: 5190: 5186: 5182: 5177: 5172: 5168: 5164: 5161:(2): 373–81. 5160: 5156: 5148: 5140: 5136: 5132: 5128: 5124: 5120: 5117:(1): 99–110. 5116: 5112: 5105: 5097: 5093: 5088: 5083: 5079: 5075: 5071: 5067: 5063: 5056: 5054: 5045: 5041: 5037: 5033: 5029: 5025: 5017: 5009: 5005: 5001: 4997: 4993: 4989: 4986:(4): 369–74. 4985: 4981: 4973: 4965: 4961: 4957: 4953: 4949: 4945: 4938: 4930: 4926: 4921: 4916: 4912: 4908: 4904: 4897: 4879: 4875: 4871: 4867: 4863: 4859: 4855: 4851: 4847: 4840: 4833: 4825: 4821: 4816: 4811: 4807: 4803: 4799: 4792: 4790: 4781: 4777: 4773: 4769: 4765: 4761: 4757: 4753: 4746: 4744: 4742: 4733: 4729: 4725: 4721: 4716: 4711: 4706: 4701: 4698:(2): 373–80. 4697: 4693: 4689: 4682: 4680: 4664: 4660: 4656: 4652: 4648: 4644: 4640: 4636: 4632: 4628: 4621: 4613: 4609: 4605: 4601: 4597: 4593: 4586: 4578: 4574: 4569: 4564: 4560: 4556: 4553:(3): 187–94. 4552: 4548: 4544: 4537: 4535: 4526: 4522: 4517: 4512: 4509:(6): 1142–8. 4508: 4504: 4500: 4493: 4485: 4481: 4476: 4471: 4468:(4): 766–71. 4467: 4463: 4459: 4452: 4444: 4440: 4436: 4432: 4428: 4424: 4421:(3): 453–61. 4420: 4416: 4409: 4401: 4396:|first8= 4389: 4381: 4377: 4372: 4367: 4363: 4359: 4355: 4351: 4347: 4340: 4332: 4328: 4323: 4318: 4313: 4308: 4304: 4300: 4296: 4289: 4281: 4277: 4273: 4269: 4266:(10): 893–9. 4265: 4261: 4254: 4246: 4242: 4237: 4232: 4227: 4222: 4218: 4214: 4210: 4203: 4195: 4191: 4186: 4181: 4177: 4173: 4169: 4165: 4161: 4154: 4146: 4142: 4138: 4134: 4130: 4126: 4122: 4118: 4111: 4103: 4099: 4094: 4089: 4085: 4081: 4077: 4073: 4069: 4062: 4054: 4050: 4045: 4040: 4035: 4030: 4026: 4022: 4019:(9): 5211–6. 4018: 4014: 4010: 4003: 3995: 3991: 3986: 3981: 3977: 3973: 3969: 3965: 3961: 3954: 3946: 3942: 3937: 3932: 3928: 3924: 3920: 3913: 3905: 3901: 3896: 3891: 3887: 3883: 3880:(4): F771–9. 3879: 3875: 3871: 3864: 3856: 3852: 3848: 3844: 3840: 3836: 3832: 3828: 3821: 3813: 3809: 3804: 3799: 3795: 3791: 3787: 3783: 3779: 3772: 3764: 3760: 3755: 3750: 3746: 3742: 3738: 3734: 3730: 3723: 3715: 3711: 3706: 3701: 3697: 3693: 3689: 3685: 3681: 3674: 3666: 3662: 3658: 3654: 3650: 3646: 3639: 3631: 3627: 3622: 3617: 3613: 3609: 3605: 3601: 3597: 3590: 3582: 3578: 3574: 3570: 3565: 3560: 3557:(2): 126–37. 3556: 3552: 3548: 3541: 3539: 3537: 3528: 3524: 3519: 3514: 3510: 3506: 3502: 3498: 3494: 3487: 3485: 3483: 3474: 3470: 3465: 3460: 3456: 3452: 3448: 3444: 3440: 3433: 3425: 3421: 3417: 3413: 3409: 3405: 3401: 3397: 3390: 3382: 3378: 3374: 3370: 3366: 3362: 3354: 3346: 3342: 3337: 3332: 3328: 3324: 3320: 3313: 3305: 3301: 3297: 3293: 3289: 3285: 3278: 3270: 3266: 3262: 3258: 3255:(5): 249–53. 3254: 3250: 3242: 3234: 3230: 3225: 3220: 3216: 3212: 3208: 3201: 3193: 3189: 3185: 3181: 3178:(3): 175–81. 3177: 3173: 3165: 3157: 3153: 3149: 3145: 3141: 3137: 3134:(4): 438–43. 3133: 3129: 3122: 3114: 3110: 3105: 3100: 3096: 3092: 3088: 3081: 3073: 3069: 3064: 3059: 3056:(5): 1393–8. 3055: 3051: 3047: 3040: 3038: 3036: 3027: 3023: 3018: 3013: 3009: 3005: 3001: 2994: 2986: 2982: 2977: 2972: 2968: 2964: 2960: 2956: 2952: 2945: 2937: 2933: 2928: 2923: 2919: 2915: 2911: 2904: 2902: 2900: 2891: 2887: 2882: 2877: 2873: 2869: 2866:(2): 267–74. 2865: 2861: 2857: 2850: 2842: 2838: 2833: 2828: 2823: 2818: 2814: 2810: 2806: 2799: 2784: 2780: 2776: 2771: 2766: 2763:(4): 929–31. 2762: 2758: 2754: 2747: 2739: 2735: 2730: 2725: 2721: 2717: 2713: 2706: 2698: 2694: 2690: 2686: 2682: 2678: 2670: 2662: 2658: 2654: 2650: 2647:(1): 210–22. 2646: 2642: 2635: 2627: 2623: 2619: 2615: 2611: 2607: 2600: 2592: 2588: 2583: 2578: 2574: 2570: 2566: 2562: 2558: 2551: 2543: 2539: 2534: 2529: 2525: 2521: 2517: 2513: 2509: 2502: 2500: 2498: 2489: 2485: 2481: 2477: 2472: 2467: 2464:(4): 175–93. 2463: 2459: 2455: 2448: 2446: 2444: 2435: 2431: 2426: 2421: 2417: 2413: 2409: 2405: 2398: 2396: 2387: 2383: 2378: 2373: 2369: 2365: 2361: 2357: 2353: 2346: 2344: 2342: 2340: 2331: 2327: 2322: 2317: 2313: 2309: 2306:(2): 109–18. 2305: 2301: 2297: 2290: 2282: 2278: 2273: 2268: 2264: 2260: 2256: 2252: 2248: 2241: 2239: 2237: 2235: 2226: 2222: 2218: 2214: 2210: 2206: 2203:(3): 204–16. 2202: 2198: 2190: 2182: 2178: 2174: 2170: 2166: 2162: 2159:(2): 202–11. 2158: 2154: 2147: 2145: 2136: 2132: 2128: 2124: 2120: 2116: 2108: 2100: 2096: 2092: 2088: 2085:(2): 105–10. 2084: 2080: 2073: 2065: 2061: 2056: 2051: 2047: 2043: 2039: 2035: 2031: 2027: 2023: 2016: 2014: 2005: 2001: 1997: 1993: 1989: 1985: 1981: 1977: 1970: 1968: 1959: 1955: 1950: 1945: 1941: 1937: 1933: 1929: 1925: 1918: 1916: 1914: 1912: 1903: 1899: 1894: 1889: 1885: 1881: 1877: 1873: 1869: 1862: 1860: 1858: 1856: 1854: 1852: 1843: 1839: 1834: 1829: 1825: 1821: 1817: 1813: 1809: 1802: 1800: 1798: 1796: 1794: 1792: 1790: 1781: 1777: 1773: 1769: 1765: 1761: 1754: 1746: 1742: 1738: 1734: 1730: 1726: 1722: 1715: 1713: 1704: 1700: 1696: 1692: 1688: 1684: 1677: 1675: 1666: 1662: 1657: 1652: 1648: 1644: 1640: 1633: 1631: 1622: 1618: 1613: 1608: 1604: 1600: 1597:(4): 723–35. 1596: 1592: 1588: 1581: 1573: 1569: 1565: 1561: 1557: 1553: 1546: 1544: 1542: 1537: 1530: 1528: 1518: 1516: 1512: 1502: 1499: 1488: 1485: 1479: 1475: 1473: 1469: 1465: 1460: 1453:Other cancers 1450: 1448: 1443: 1439: 1435: 1431: 1427: 1422: 1420: 1416: 1412: 1408: 1404: 1400: 1396: 1392: 1388: 1384: 1377:Breast cancer 1369: 1366: 1362: 1358: 1348: 1346: 1342: 1337: 1335: 1331: 1326: 1324: 1321:responses to 1320: 1315: 1311: 1306: 1303: 1299: 1295: 1291: 1287: 1276: 1274: 1270: 1266: 1262: 1258: 1253: 1249: 1247: 1243: 1238: 1233: 1231: 1230:gene knockout 1213:Human studies 1210: 1208: 1198: 1196: 1192: 1188: 1182: 1180: 1176: 1175:gene knockout 1171: 1168: 1158: 1150: 1147: 1142: 1140: 1135: 1131: 1121: 1119: 1114: 1105: 1096: 1094: 1090: 1086: 1082: 1081:Na+/K+-ATPase 1078: 1068: 1065: 1061: 1057: 1053: 1049: 1045: 1041: 1031: 1028: 1023: 1014: 1012: 1008: 1002: 1000: 996: 991: 989: 985: 981: 977: 972: 970: 966: 961: 959: 955: 951: 947: 943: 939: 935: 931: 927: 907: 905: 900: 891: 888: 884: 880: 876: 872: 868: 864: 860: 856: 852: 848: 844: 839: 836: 832: 828: 824: 820: 816: 812: 808: 804: 800: 796: 792: 788: 784: 780: 776: 772: 768: 764: 760: 756: 752: 748: 744: 740: 735: 733: 729: 720: 718: 714: 710: 706: 702: 698: 694: 690: 686: 682: 678: 668: 665: 661: 657: 653: 649: 645: 641: 637: 633: 629: 625: 621: 619: 615: 611: 607: 603: 599: 589: 587: 583: 579: 574: 572: 561: 559: 555: 551: 547: 542: 538: 534: 529: 527: 523: 519: 515: 511: 506: 504: 500: 496: 492: 488: 484: 479: 475: 472:, metabolize 471: 467: 463: 448: 446: 442: 437: 433: 429: 425: 421: 417: 413: 409: 397: 391: 385: 378: 376: 373: 372: 351: 348: 344: 343: 338: 329: 328: 325: 318: 307: 300: 299: 296: 289: 281: 277: 273: 272: 270: 260: 256: 255: 248: 244: 243: 241: 235: 231: 230: 226: 222: 220: 217: 216: 209: 205: 204: 202: 200: 197: 196: 189: 185: 184: 182: 179: 175: 174: 167: 163: 162: 160: 158: 155: 154: 147: 143: 142: 140: 138: 135: 134: 127: 123: 122: 120: 116: 111: 110: 103: 99: 98: 96: 93: 89: 88: 83: 75: 69: 65: 61: 57: 51: 47: 42: 38: 33: 27: 19: 7679:Cell biology 7651: 7650: 7491:Cannabigerol 7462: 7415: 7357: 7345: 7307:black pepper 7267:chili pepper 7200:chili pepper 7190:chili pepper 7181:Hepoxilin B3 7176:Hepoxilin A3 7147: 7119:chili pepper 7077:chili pepper 7018: 6971: 6881: 6740: 6667:Clotrimazole 6608: 6592: 6544:Frescolat ML 6452:Progesterone 6361:Adhyperforin 6274:WIN 55,212-2 6267: 6118: 6086:Hepoxilin B3 6081:Hepoxilin A3 6052: 5984:Cannabigerol 5781: 5777: 5771: 5738: 5734: 5727: 5694: 5690: 5684: 5651: 5647: 5641: 5604: 5600: 5590: 5563: 5559: 5549: 5514: 5510: 5500: 5476:(4): 163–9. 5473: 5469: 5423: 5419: 5365: 5361: 5351: 5306: 5302: 5292: 5262:(1): 10–20. 5259: 5255: 5215:(1): 37–48. 5212: 5208: 5201: 5158: 5154: 5147: 5114: 5110: 5104: 5069: 5065: 5027: 5023: 5016: 4983: 4979: 4972: 4950:(3): 145–7. 4947: 4943: 4937: 4910: 4906: 4896: 4885:. Retrieved 4849: 4845: 4832: 4805: 4801: 4755: 4751: 4695: 4692:Hypertension 4691: 4667:. Retrieved 4634: 4630: 4620: 4598:(1): 74–81. 4595: 4591: 4585: 4550: 4546: 4506: 4503:Hypertension 4502: 4492: 4465: 4462:Hypertension 4461: 4451: 4418: 4414: 4408: 4388:cite journal 4353: 4349: 4339: 4302: 4298: 4288: 4263: 4259: 4253: 4216: 4212: 4202: 4167: 4163: 4153: 4120: 4116: 4110: 4075: 4071: 4061: 4016: 4012: 4002: 3967: 3963: 3953: 3926: 3923:Hypertension 3922: 3912: 3877: 3873: 3863: 3830: 3826: 3820: 3785: 3781: 3771: 3736: 3732: 3722: 3687: 3683: 3673: 3648: 3644: 3638: 3606:(1): 67–74. 3603: 3599: 3589: 3554: 3550: 3500: 3496: 3449:(1): 43–54. 3446: 3442: 3432: 3402:(2): 210–6. 3399: 3396:Hypertension 3395: 3389: 3364: 3360: 3353: 3326: 3322: 3312: 3287: 3283: 3277: 3252: 3248: 3241: 3214: 3210: 3200: 3175: 3171: 3164: 3131: 3127: 3121: 3094: 3090: 3080: 3053: 3050:Hypertension 3049: 3007: 3003: 2993: 2958: 2954: 2944: 2917: 2913: 2863: 2859: 2849: 2812: 2808: 2798: 2787:. Retrieved 2760: 2756: 2746: 2719: 2715: 2705: 2683:(2): 201–5. 2680: 2676: 2669: 2644: 2640: 2634: 2609: 2605: 2599: 2564: 2560: 2550: 2518:(1): 37–46. 2515: 2511: 2461: 2457: 2407: 2359: 2355: 2303: 2299: 2289: 2254: 2250: 2200: 2196: 2189: 2156: 2152: 2121:(5): 790–7. 2118: 2114: 2107: 2082: 2078: 2072: 2032:(1): 73–83. 2029: 2025: 1982:(2): 63–71. 1979: 1975: 1931: 1927: 1875: 1871: 1815: 1811: 1766:(1): 55–68. 1763: 1759: 1753: 1728: 1724: 1686: 1682: 1646: 1642: 1594: 1590: 1580: 1555: 1551: 1524: 1508: 1494: 1480: 1476: 1456: 1423: 1391:transfection 1380: 1365:mitochondria 1354: 1344: 1338: 1327: 1307: 1301: 1297: 1293: 1289: 1282: 1254: 1250: 1234: 1226: 1204: 1187:vasodilation 1183: 1172: 1164: 1156: 1143: 1127: 1111: 1102: 1099:Hypertension 1074: 1037: 1020: 1007:hypertension 1003: 992: 982:(eNOS) with 976:nitric oxide 973: 962: 923: 901: 897: 882: 878: 874: 870: 866: 862: 858: 854: 850: 846: 842: 840: 830: 826: 822: 818: 814: 810: 806: 802: 798: 790: 786: 782: 778: 774: 770: 766: 762: 758: 736: 726: 705:inflammation 674: 624:Nitric oxide 622: 595: 575: 567: 530: 525: 521: 517: 514:stereoisomer 509: 507: 494: 490: 486: 482: 460:A subset of 459: 451:Biosynthesis 423: 419: 415: 411: 407: 406: 85:Identifiers 77:Other names 67: 63: 59: 55: 26: 7689:Eicosanoids 7684:Fatty acids 7626:Tivanisiran 7531:Capsazepine 7443:Zucapsaicin 7311:long pepper 7277:Pacific yew 7166:GSK1016790A 7053:Cannabidiol 7039:camphorweed 6727:RQ-00203078 6722:PF-05105679 6662:Capsazepine 6427:GSK2293017A 6391:Substance P 6376:GSK1702934A 6325:PF-04745637 6264:Umbellulone 6185:Pacific yew 6171:Oleocanthal 6150:wintergreen 6111:Ligustilide 5974:Cannabidiol 5939:horseradish 5176:2434/421160 4305:(1): 63–9. 4299:Circulation 4078:(4): 23–8. 3128:Circulation 2300:Xenobiotica 1934:(1): 1–12. 1505:Vasculature 1323:epinephrine 1263:(SNP) (see 1139:vasopressin 930:vasopressin 904:neutrophils 797:to form 12( 711:with human 677:lauric acid 652:gemfibrozil 610:endothelins 582:epoxygenase 340:Properties 146:CHEBI:34306 7673:Categories 7521:Cannabinol 7421:pooissonii 7412:Tinyatoxin 7363:pooissonii 7327:Probenecid 7317:Polygodial 7273:Paclitaxel 7257:PAVA spray 7144:Evodiamine 7095:pepperwort 7010:Anandamide 6977:α-Sanshool 6925:Activators 6878:Triptolide 6871:Activators 6783:Activators 6759:TRPM4-IN-5 6677:Elismetrep 6605:stevioside 6533:eucalyptus 6529:Eucalyptol 6493:ADP-ribose 6486:Activators 6422:GSK417651A 6381:Hyperforin 6354:Activators 6234:Tear gases 6206:Polygodial 6196:PF-4840154 6181:Paclitaxel 6049:Dicentrine 5959:Bradykinin 5894:α-Sanshool 5862:Activators 5844:modulators 5607:: 243–55. 4887:2020-05-24 4669:2018-08-27 2789:2019-08-16 2612:: 413–38. 1558:: 413–38. 1533:References 1430:Pseudogene 1411:MDA-MB-231 1246:Odds ratio 1167:transgenic 1048:Thrombosis 1044:thrombosis 934:endothelin 757:and to 11( 723:Metabolism 632:superoxide 588:products. 428:eicosanoid 375:Molar mass 178:IUPHAR/BPS 157:ChemSpider 113:3D model ( 102:79551-86-3 92:CAS Number 7652:See also: 7636:TRPV3-74a 7621:SB-705498 7616:SB-366791 7566:Lanthanum 7561:HC-067047 7481:Asivatrep 7342:Rutamarin 7206:Incensole 7156:Gingerols 7125:Estradiol 7101:, others) 7083:Carvacrol 7073:Capsaicin 6967:13-oxoODE 6957:12S-HpETE 6937:5',6'-EET 6737:Rutamarin 6636:Thio-BCTC 6589:Rutamarin 6519:Coolact P 6310:HC-030031 6175:olive oil 6071:Gingerols 5884:12S-HpETE 4700:CiteSeerX 4307:CiteSeerX 1419:apoptosis 1361:orthologs 1257:haplotype 946:Androgens 835:chirality 739:platelets 598:Androgens 466:microsome 464:(CYP450) 7586:NGD-8243 7571:Mavatrep 7556:GRC-6211 7525:cannabis 7515:cannabis 7505:cannabis 7495:cannabis 7476:AMG-9810 7452:Blockers 7433:Vanillin 7428:Tramadol 7392:cannabis 7370:Shogaols 7303:Piperine 7067:cannabis 7057:cannabis 7035:rosemary 6952:12S-HETE 6947:9-oxoODE 6894:Blockers 6844:PI(4,5)P 6832:Blockers 6810:PI(3,5)P 6717:Ononetin 6702:Nicotine 6650:Blockers 6626:fructose 6618:tastants 6564:Linalool 6549:Geraniol 6509:CIM-0216 6400:Blockers 6315:Nicotine 6290:A-967079 6283:Blockers 6243:cannabis 6216:Shogaols 6161:Nicotine 6127:Linalool 6066:Formalin 6028:turmeric 6024:Curcumin 5998:cinnamon 5988:cannabis 5978:cannabis 5968:cannabis 5954:ASP-7663 5912:Acrolein 5798:19013235 5763:21503433 5755:16081682 5711:15059886 5676:37734580 5668:16243809 5633:23569388 5582:19846914 5541:21120482 5492:22798501 5448:11952881 5440:25701119 5402:21209903 5362:PLOS ONE 5343:25549350 5303:PLOS ONE 5284:25094029 5237:23747687 5193:19189811 5185:24337409 5139:13728834 5131:25178427 5096:23176821 5044:29628049 5030:: 6–13. 5008:34470511 5000:24418943 4964:19097922 4929:18787519 4878:Archived 4866:24984178 4824:18971550 4780:14217802 4772:21625857 4724:18574070 4663:Archived 4651:22173545 4612:17341693 4577:20130494 4525:18936345 4484:16144986 4443:23680415 4435:18300855 4380:18385420 4331:15611369 4245:22389490 4194:16691295 4137:20943934 4102:19713718 4053:11320253 3994:23641057 3904:19211690 3855:30640395 3812:23438293 3763:23220478 3714:21474427 3665:25820395 3630:23658377 3581:26569858 3573:24298905 3527:21610722 3473:27492226 3416:15226275 3381:15130884 3304:21239640 3233:14612451 3192:10841040 3148:15262846 3072:18391101 3026:10722687 2936:16081420 2841:25249502 2783:Archived 2779:24406470 2738:16835590 2661:20869469 2626:15822183 2591:23362865 2542:25427230 2480:16258232 2434:25526688 2386:21722750 2330:20021200 2281:25986599 2257:: 40–9. 2225:16527260 2173:20716162 2135:25872594 2099:20630735 2064:22841774 1996:22706230 1958:23584425 1902:23688133 1842:25813407 1818:: 9–16. 1745:18156192 1721:Falck JR 1703:18433732 1665:14660610 1621:20941528 1572:15822183 1511:receptor 1259:tagging 1165:Cyp4a12- 995:receptor 660:propanol 7606:RN-9893 7601:RN-1734 7471:AMG-517 7437:vanilla 7406:oregano 7378:Sichuan 7356:(RTX) ( 7332:Protons 7295:(e.g., 7228:Menthol 7210:incense 7130:Eugenol 7087:oregano 7027:Camphor 6995:Allicin 6985:Sichuan 6972:20-HETE 6962:13-HODE 6805:ML2-SA1 6706:tobacco 6657:AMG-333 6630:sucrose 6622:glucose 6620:(e.g., 6603:(e.g., 6569:Menthol 6503:Calcium 6319:tobacco 6295:AM-0902 6224:Sichuan 6165:tobacco 6054:Lindera 5931:mustard 5917:Allicin 5902:Sichuan 5879:4,5-EET 5841:channel 5719:5252711 5624:3615879 5573:2807614 5532:3839420 5483:3601443 5393:3012715 5370:Bibcode 5334:4280215 5311:Bibcode 5264:Bibcode 5217:Bibcode 5087:3516610 4874:6754178 4732:6884532 4659:7528853 4568:3932492 4371:2488260 4280:8274222 4236:3340178 4185:1459070 4093:2790762 4021:Bibcode 3985:3736709 3945:9039121 3895:2670635 3847:8258666 3803:4106241 3754:3567350 3705:3119152 3621:3684845 3518:3208155 3464:5091366 3345:1648091 3269:1525186 3156:9244739 3113:2501294 2985:7690778 2890:1327375 2881:1907511 2832:4617135 2697:9675028 2582:3791982 2533:4260681 2488:4694718 2425:4385421 2377:3248593 2321:3067055 2272:4575609 2205:Bibcode 2181:3481077 2055:3439529 2034:Bibcode 2004:5258044 1949:4292790 1893:4245146 1833:4575602 1780:9866708 1612:2962793 1265:Tag SNP 1093:nephron 1040:C57BL/6 1038:In the 697:12-HETE 648:opioids 586:epoxide 550:CYP4A22 533:CYP4A11 441:rodents 380:320.473 247:5283157 234:PubChem 166:4446281 7546:DHEA-S 7398:Thymol 7374:ginger 7297:4α-PDD 7160:ginger 6999:garlic 6981:ginger 6942:9-HODE 6839:ML-SI3 6800:ML-SA1 6795:MK6-83 6616:Sweet 6579:PMD 38 6559:Icilin 6412:DHEA-S 6304:celery 6220:ginger 6115:celery 6106:JT-010 6096:Icilin 6075:ginger 6038:celery 5943:wasabi 5935:radish 5921:garlic 5898:ginger 5796: 5761: 5753: 5717: 5709: 5674: 5666: 5631: 5621: 5580: 5570: 5539: 5529: 5490: 5480: 5446: 5438: 5400: 5390: 5341: 5331: 5282: 5235: 5191: 5183: 5137: 5129: 5094: 5084: 5042: 5006: 4998: 4962: 4927: 4872: 4864: 4822: 4778: 4770: 4730: 4722: 4702: 4657: 4649: 4610: 4575: 4565: 4523: 4482: 4441: 4433: 4378: 4368: 4329: 4309: 4278: 4243: 4233: 4192: 4182: 4145:959890 4143: 4135: 4100: 4090: 4051: 4041: 3992: 3982: 3943: 3902: 3892: 3853: 3845: 3810: 3800: 3761: 3751: 3712: 3702: 3663: 3628: 3618: 3579: 3571: 3525: 3515: 3471: 3461: 3424:434047 3422: 3414: 3379: 3343: 3302: 3267: 3231: 3190: 3154: 3146: 3111: 3070: 3024: 2983: 2976:288277 2973: 2934: 2888: 2878: 2839: 2829: 2777: 2736: 2695: 2659: 2624: 2589: 2579: 2540: 2530: 2486: 2478: 2432: 2422: 2384: 2374: 2328: 2318: 2279: 2269: 2223: 2179: 2171: 2133: 2097: 2062: 2052: 2002: 1994: 1956: 1946: 1900: 1890: 1840: 1830: 1778: 1743: 1701: 1663: 1619: 1609: 1570: 1459:Glioma 1403:Balb/c 1387:BT-474 1372:Cancer 1345:CYP4F2 1334:intron 1027:intima 689:5-HETE 630:, and 612:, and 578:CYP2J2 554:CYP2U1 546:CYP4Z1 541:CYP4F3 539:, and 537:CYP4F2 503:CYP4F8 499:CYP2U1 324:SMILES 208:C14748 44:Names 7536:DCDPC 7402:thyme 7138:clove 7134:basil 7091:thyme 7005:AM404 6932:2-APB 6818:SF-22 6790:EVP21 6774:TRPML 6672:DCDPC 6641:WS-12 6407:DCDPC 6258:onion 6135:thyme 6057:spp.) 6018:cumin 5949:AM404 5759:S2CID 5715:S2CID 5672:S2CID 5444:S2CID 5189:S2CID 5135:S2CID 5004:S2CID 4881:(PDF) 4870:S2CID 4842:(PDF) 4776:S2CID 4728:S2CID 4655:S2CID 4439:S2CID 4141:S2CID 4044:33189 3851:S2CID 3577:S2CID 3420:S2CID 3152:S2CID 2484:S2CID 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