311:
198:
24:
498:
33:
493:
601:
652:
606:
605:
778:
mutations in genes, with 1 to 2 of these mutations being within essential genes and therefore lethal. However, since it is unlikely the same essential gene is mutated in independent gametes, and if loss of the essential gene did not kill the gamete itself, downstream gamete fusion often allows for
604:
918:
were found to be more sensitive to inactivation by EMS than wild type bacteriophage. This finding suggests that a recombination process catalyzed by the proteins specified by these six genes is employed in repairing EMS lethal lesions in DNA.
939:"inactivating solution", for at least six half-lives (>24 hours). The half-life of EMS in 1M NaOH is 6 hours at room temperature, while in a 10% w/v sodium thiosulfate solution it has a half-life of 1.4 hours.
506:
473:
764:
EMS can induce mutations at a rate of 5x10 to 5x10 per gene without substantial killing. A 5x10 per gene mutation rate observed in a typical EMS mutagenesis experiment of the model organism
770:, corresponds to a raw mutation rate of ~7x10 mutations per G/C base pair, or about 250 mutations within an originally mutagenized gamete (containing a ~100 Mbp, 36%
607:
1462:
FROESE-GERTZEN, EDITH E.; KONZAK, C. F.; FOSTER, R.; NILAN, R. A. (1963). "Correlation between Some
Chemical and Biological Reactions of Ethyl Methanesulphonate".
927:
Generally speaking EMS is unstable in water. It hydrolyzes to ethanol and methanesulfonic acid. At neutral to acidic pH at room temperature, it has a fairly long
665:
1365:
Yost Jr, H. T.; Chaleff, R. S.; Finerty, J. P. (1967). "Induction of mitotic recombination in
Saccharomyces cerevisiae by ethyl methane sulphonate".
629:
931:
of over 1 day. Therefore, EMS must be specifically degraded before disposal. Protocols call for degradation of EMS in an equal volume of a 0.1M
360:
1419:
Johns, V.; Bernstein, C.; Bernstein, H. (1978). "Recombinational repair of alkylation lesions in phage T4. II. Ethyl methanesulfonate".
622:
968:
660:
861:
1297:"Persistence of O6-Ethylguanine in Rat-Brain DNA: Correlation with Nervous System-Specific Carcinogenesis by Ethylnitrosourea"
1525:
1185:
1560:
325:
894:
672:
615:
1021:
1050:
107:
542:
268:
193:
289:
155:
1069:
560:
497:
1555:
872:-ethylguanine was reported to be about 9 days in mouse brain, while it was about 1 day in mouse liver.
492:
32:
23:
205:
1580:
889:
884:
306:
1209:
Gerchman, Lois L.; Ludlum, David B. (1973). "The properties of in templates for RNA polymerase".
973:
831:
mutation). This changes the genetic information, is often harmful to cells, and can result in
1575:
915:
828:
747:
692:
520:
485:
1471:
1374:
1308:
904:
715:
277:
45:
175:
8:
1570:
775:
548:
73:
1475:
1378:
1312:
310:
197:
135:
83:
1495:
1444:
1398:
1090:
936:
1339:
1296:
1265:
1177:
1565:
1531:
1521:
1487:
1436:
1390:
1344:
1326:
1277:
1269:
1234:
1226:
1222:
1191:
1181:
1145:
1137:
1133:
1095:
1516:
Kodym, Andrea; Afza, Rownak (2003). "Chapter 12 Physical and
Chemical Mutagenesis".
1499:
1448:
1479:
1455:
1428:
1402:
1382:
1334:
1316:
1261:
1218:
1173:
1129:
1120:
Sega, Gary A. (1984). "A review of the genetic effects of ethyl methanesulfonate".
1085:
1077:
978:
719:
383:
812:
556:
257:
564:
758:
727:
643:
458:
1549:
1491:
1330:
1273:
1230:
1195:
1141:
1081:
860:
in a stoichiometric fashion by reacting with the active site cysteine of the
448:
438:
186:
1535:
823:-ethylguanine. Following subsequent rounds of replication, the original G:C
1281:
1099:
780:
1394:
1348:
1321:
1252:
Pegg, Anthony E (2000). "Repair of O6-alkylguanine by alkyltransferases".
1238:
1149:
628:
568:
1440:
1211:
Biochimica et
Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis
1003:
800:
774:
haploid genome). Such a mutagenized gamete would have about 9 different
614:
1432:
956:
898:
771:
766:
754:
743:
621:
410:
206:
166:
1483:
1386:
952:
928:
824:
788:
819:
the process frequently place thymine, instead of cytosine, opposite
642:
Except where otherwise noted, data are given for materials in their
1172:. Methods in Cell Biology. Vol. 48. Elsevier. pp. 31–58.
816:
739:
723:
587:
232:
580:
106:
1170:
Caenorhabditis elegans: Modern
Biological Analysis of an Organism
948:
881:
856:
836:
832:
751:
722:. EMS is the most commonly used chemical mutagen in experimental
552:
428:
244:
1461:
1202:
907:
784:
761:. Due to its potency and well understood mutational spectrum,
146:
453:
85–86 °C (185–187 °F; 358–359 K) /10 mmHg(lit)
126:
96:
726:. Mutations induced by EMS exposure can then be studied in
294:
932:
911:
223:
1470:(4879). Springer Science and Business Media LLC: 447–448.
779:
survival of the resulting zygote and organism, as the now
983:
804:
534:
1288:
1418:
530:
1364:
1113:
1245:
1168:Anderson, Philip (1995). "Chapter 2 Mutagenesis".
526:
1074:WormBook: The Online Review of C. Elegans Biology
1547:
256:
1520:. Totowa, N.J: Humana Press. pp. 189–203.
1301:Proceedings of the National Academy of Sciences
1122:Mutation Research/Reviews in Genetic Toxicology
1070:"Forward and reverse mutagenesis in C. elegans"
603:
82:
1254:Mutation Research/Reviews in Mutation Research
1208:
1163:
1161:
1159:
1067:
746:substitution; particularly through G:C to A:T
718:. A colorless liquid, it is classified as an
576:
875:
846:
733:
1414:
1412:
1294:
1511:
1509:
1360:
1358:
1156:
794:
572:
334:InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
309:
196:
174:
1515:
1409:
1338:
1320:
1089:
1029:Report on Carcinogens, Fourteenth Edition
969:Mutagenesis (molecular biology technique)
344:InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
276:
1506:
1355:
1295:Goth, R.; Rajewsky, M. F. (1974-03-01).
1167:
1068:Kutscher, Lena M.; Shaham, Shai (2014).
862:O-6-methylguanine-DNA methyltransferase
305:
1548:
187:
791:allele provided by the other gamete.
337:Key: PLUBXMRUUVWRLT-UHFFFAOYSA-N
154:
134:
1251:
1119:
839:(RNA analog of thymine) opposite an
347:Key: PLUBXMRUUVWRLT-UHFFFAOYAM
247:
231:
13:
599:
14:
1592:
1421:Molecular & General Genetics
835:. RNA polymerase can also place
650:
496:
491:
31:
22:
646:(at 25 °C , 100 kPa).
1061:
1043:
1014:
996:
854:-ethylguanine can be repaired
803:of EMS reacts with guanine in
757:. EMS typically produces only
1:
1266:10.1016/s1383-5742(00)00017-x
1178:10.1016/s0091-679x(08)61382-5
1128:(2–3). Elsevier BV: 113–142.
989:
901:leading to genetic exchange.
893:. It was suggested that EMS
1260:(2–3). Elsevier BV: 83–100.
1223:10.1016/0005-2787(73)90160-3
1134:10.1016/0165-1110(84)90007-1
922:
910:defective in any one of six
807:, forming the abnormal base
787:may be rescued by the still
714:. It is the ethyl ester of
7:
1217:(2). Elsevier BV: 310–316.
962:
10:
1597:
876:Induction of recombination
847:Repair of mutagenic lesion
827:can become an A:T pair (a
734:Use in biological research
415:124.16 g/mol
1561:IARC Group 2B carcinogens
1518:Plant functional genomics
942:
914:known to be required for
640:
472:
467:
376:
356:
321:
66:
56:
44:
39:
30:
21:
1082:10.1895/wormbook.1.167.1
1055:pubchem.ncbi.nlm.nih.gov
1051:"Ethyl methanesulfonate"
1022:"Ethyl Methanesulfonate"
890:Saccharomyces cerevisiae
795:Mechanism of mutagenesis
543:Precautionary statements
815:, DNA polymerases that
783:non-functional mutated
742:in genetic material by
423:Clear colorless liquid
61:Ethyl methanesulphonate
17:Ethyl methanesulfonate
843:-ethylguanine lesion.
811:-ethylguanine. During
685:Ethyl methanesulfonate
610:
50:Ethyl methanesulfonate
1322:10.1073/pnas.71.3.639
916:genetic recombination
693:organosulfur compound
609:
864:repair protein. The
738:EMS produces random
716:methanesulfonic acid
592:(fire diamond)
433:1.1452 g/cm (22 °C)
46:Preferred IUPAC name
1476:1963Natur.198..447F
1379:1967Natur.215..660Y
1313:1974PNAS...71..639G
18:
1433:10.1007/BF00266913
1076:. WormBook: 1–26.
937:sodium thiosulfate
673:Infobox references
611:
16:
1556:Ethylating agents
1527:978-1-58829-145-5
1373:(5101): 660–661.
1187:978-0-12-564149-4
730:or other assays.
695:with the formula
681:Chemical compound
679:
678:
521:Hazard statements
463:0.044 kPa @ 25˚C
290:CompTox Dashboard
108:Interactive image
1588:
1540:
1539:
1513:
1504:
1503:
1484:10.1038/198447a0
1459:
1453:
1452:
1416:
1407:
1406:
1387:10.1038/215660a0
1362:
1353:
1352:
1342:
1324:
1292:
1286:
1285:
1249:
1243:
1242:
1206:
1200:
1199:
1165:
1154:
1153:
1117:
1111:
1110:
1108:
1106:
1093:
1065:
1059:
1058:
1047:
1041:
1040:
1038:
1036:
1026:
1018:
1012:
1007:, 11th Edition,
1000:
905:Bacteriophage T4
897:may result in a
776:loss-of-function
720:alkylating agent
713:
663:
657:
654:
653:
631:
624:
617:
602:
582:
578:
574:
570:
566:
562:
558:
554:
550:
536:
532:
528:
500:
495:
384:Chemical formula
314:
313:
298:
296:
280:
260:
249:
235:
208:
200:
189:
178:
158:
138:
110:
86:
35:
26:
19:
15:
1596:
1595:
1591:
1590:
1589:
1587:
1586:
1585:
1581:Mesylate esters
1546:
1545:
1544:
1543:
1528:
1514:
1507:
1460:
1456:
1417:
1410:
1363:
1356:
1293:
1289:
1250:
1246:
1207:
1203:
1188:
1166:
1157:
1118:
1114:
1104:
1102:
1066:
1062:
1049:
1048:
1044:
1034:
1032:
1024:
1020:
1019:
1015:
1001:
997:
992:
965:
945:
925:
878:
849:
813:DNA replication
797:
759:point mutations
736:
728:genetic screens
712:
708:
704:
700:
696:
682:
675:
670:
669:
668: ?)
659:
655:
651:
647:
636:
635:
634:
633:
626:
619:
612:
608:
600:
545:
523:
509:
488:
404:
400:
396:
392:
386:
372:
369:
364:
363:
352:
349:
348:
345:
339:
338:
335:
329:
328:
317:
299:
292:
283:
263:
250:
238:
218:
181:
161:
141:
113:
100:
89:
76:
62:
60:
52:
51:
12:
11:
5:
1594:
1584:
1583:
1578:
1573:
1568:
1563:
1558:
1542:
1541:
1526:
1505:
1454:
1427:(2): 197–207.
1408:
1354:
1307:(3): 639–643.
1287:
1244:
1201:
1186:
1155:
1112:
1060:
1042:
1013:
994:
993:
991:
988:
987:
986:
981:
976:
971:
964:
961:
944:
941:
924:
921:
899:repair process
877:
874:
848:
845:
796:
793:
735:
732:
710:
706:
702:
698:
680:
677:
676:
671:
649:
648:
644:standard state
641:
638:
637:
627:
620:
613:
598:
597:
596:
595:
593:
584:
583:
546:
541:
538:
537:
524:
519:
516:
515:
510:
505:
502:
501:
489:
484:
481:
480:
470:
469:
465:
464:
461:
459:Vapor pressure
455:
454:
451:
445:
444:
441:
435:
434:
431:
425:
424:
421:
417:
416:
413:
407:
406:
402:
398:
394:
390:
387:
382:
379:
378:
374:
373:
371:
370:
367:
359:
358:
357:
354:
353:
351:
350:
346:
343:
342:
340:
336:
333:
332:
324:
323:
322:
319:
318:
316:
315:
302:
300:
288:
285:
284:
282:
281:
273:
271:
265:
264:
262:
261:
253:
251:
243:
240:
239:
237:
236:
228:
226:
220:
219:
217:
216:
212:
210:
202:
201:
191:
183:
182:
180:
179:
171:
169:
163:
162:
160:
159:
151:
149:
143:
142:
140:
139:
131:
129:
123:
122:
119:
118:Abbreviations
115:
114:
112:
111:
103:
101:
94:
91:
90:
88:
87:
79:
77:
72:
69:
68:
64:
63:
59:Ethyl mesylate
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
9:
6:
4:
3:
2:
1593:
1582:
1579:
1577:
1574:
1572:
1569:
1567:
1564:
1562:
1559:
1557:
1554:
1553:
1551:
1537:
1533:
1529:
1523:
1519:
1512:
1510:
1501:
1497:
1493:
1489:
1485:
1481:
1477:
1473:
1469:
1465:
1458:
1450:
1446:
1442:
1438:
1434:
1430:
1426:
1422:
1415:
1413:
1404:
1400:
1396:
1392:
1388:
1384:
1380:
1376:
1372:
1368:
1361:
1359:
1350:
1346:
1341:
1336:
1332:
1328:
1323:
1318:
1314:
1310:
1306:
1302:
1298:
1291:
1283:
1279:
1275:
1271:
1267:
1263:
1259:
1255:
1248:
1240:
1236:
1232:
1228:
1224:
1220:
1216:
1212:
1205:
1197:
1193:
1189:
1183:
1179:
1175:
1171:
1164:
1162:
1160:
1151:
1147:
1143:
1139:
1135:
1131:
1127:
1123:
1116:
1101:
1097:
1092:
1087:
1083:
1079:
1075:
1071:
1064:
1056:
1052:
1046:
1030:
1023:
1017:
1010:
1006:
1005:
999:
995:
985:
982:
980:
977:
975:
972:
970:
967:
966:
960:
958:
954:
950:
940:
938:
934:
930:
920:
917:
913:
909:
906:
902:
900:
896:
895:damage to DNA
892:
891:
886:
885:recombination
883:
873:
871:
868:half-life of
867:
863:
859:
858:
853:
844:
842:
838:
834:
830:
826:
822:
818:
814:
810:
806:
802:
792:
790:
786:
782:
777:
773:
769:
768:
762:
760:
756:
753:
749:
745:
741:
731:
729:
725:
721:
717:
694:
690:
686:
674:
667:
662:
645:
639:
632:
625:
618:
594:
591:
590:
586:
585:
547:
544:
540:
539:
525:
522:
518:
517:
514:
511:
508:
504:
503:
499:
494:
490:
487:
483:
482:
478:
476:
471:
466:
462:
460:
457:
456:
452:
450:
449:Boiling point
447:
446:
442:
440:
439:Melting point
437:
436:
432:
430:
427:
426:
422:
419:
418:
414:
412:
409:
408:
388:
385:
381:
380:
375:
368:O=S(=O)(OCC)C
366:
365:
362:
355:
341:
331:
330:
327:
320:
312:
308:
307:DTXSID6025309
304:
303:
301:
291:
287:
286:
279:
275:
274:
272:
270:
267:
266:
259:
255:
254:
252:
246:
242:
241:
234:
230:
229:
227:
225:
222:
221:
214:
213:
211:
209:
204:
203:
199:
195:
192:
190:
188:ECHA InfoCard
185:
184:
177:
173:
172:
170:
168:
165:
164:
157:
153:
152:
150:
148:
145:
144:
137:
133:
132:
130:
128:
125:
124:
120:
117:
116:
109:
105:
104:
102:
98:
93:
92:
85:
81:
80:
78:
75:
71:
70:
65:
55:
47:
43:
38:
34:
29:
25:
20:
1576:Ethyl esters
1517:
1467:
1463:
1457:
1424:
1420:
1370:
1366:
1304:
1300:
1290:
1257:
1253:
1247:
1214:
1210:
1204:
1169:
1125:
1121:
1115:
1103:. Retrieved
1073:
1063:
1054:
1045:
1033:. Retrieved
1028:
1016:
1008:
1002:
998:
957:carcinogenic
946:
935:and 20% w/v
926:
903:
888:
880:EMS induces
879:
869:
865:
855:
851:
850:
840:
820:
808:
798:
781:heterozygous
765:
763:
737:
688:
684:
683:
588:
512:
474:
156:ChEMBL338686
67:Identifiers
57:Other names
1004:Merck Index
953:teratogenic
801:ethyl group
750:induced by
748:transitions
507:Signal word
443:< 25 °C
420:Appearance
377:Properties
194:100.000.488
136:CHEBI:23994
1571:Teratogens
1550:Categories
990:References
829:transition
767:C. elegans
755:alkylation
744:nucleotide
486:Pictograms
411:Molar mass
278:9H154DI0UP
167:ChemSpider
95:3D model (
74:CAS Number
1492:0028-0836
1331:0027-8424
1274:1383-5742
1231:0005-2787
1196:0091-679X
1142:0165-1110
949:mutagenic
929:half-life
923:Stability
825:base pair
740:mutations
565:P301+P317
477:labelling
215:200-536-7
207:EC Number
1566:Mutagens
1536:51445955
1500:12359460
1449:30597383
1282:10767620
1100:24449699
963:See also
817:catalyze
789:wildtype
724:genetics
691:) is an
589:NFPA 704
468:Hazards
1472:Bibcode
1403:1982778
1395:6050236
1375:Bibcode
1349:4522778
1309:Bibcode
1239:4706005
1150:6390190
1105:18 June
1091:4078664
1035:18 June
1031:. NIEHS
947:EMS is
908:mutants
882:mitotic
866:in vivo
857:in vivo
837:uridine
833:disease
752:guanine
666:what is
664: (
429:Density
405:
245:PubChem
84:62-50-0
1534:
1524:
1498:
1490:
1464:Nature
1447:
1441:215891
1439:
1401:
1393:
1367:Nature
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785:allele
661:verify
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513:Danger
361:SMILES
233:C19239
147:ChEMBL
40:Names
1496:S2CID
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1025:(PDF)
912:genes
326:InChI
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557:P270
553:P264
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535:H351
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527:H302
269:UNII
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224:KEGG
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