491:
268:
179:
1848:
511:
35:
413:
737:
Halliwell, B (December 1998). "Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies".
831:
1155:
1087:
774:"Cellular background level of 8-oxo-7,8-dihydro-2'-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up"
1379:
1232:
1374:
1364:
1275:
1198:
702:
Kasai, H (December 1997). "Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis".
1247:
824:
817:
594:; as noted in the article about them, such species may have a role in aging and male infertility, and 8-oxoguanine can be used to measure such stress.
426:
1044:
1039:
574:, deficient expression of this enzyme causes 8-oxoguanine to accumulate in DNA. This accumulation may then lead upon replication of DNA to
327:
538:
Care must be taken in the assay of 8-oxoguanine due to the ease with which it can be oxidised during extraction and the assay procedure.
772:
Ravanat, JL; Douki, T; Duez, P; Gremaud, E; Herbert, K; Hofer, T; Lasserre, L; Saint-Pierre, C; Favier, A; Cadet, J (November 2002).
109:
116:
1781:
1755:
1416:
1471:
421:
1724:
1655:
282:
1739:
433:
610:
527:
Increased concentrations of 8-oxoguanine in body fluids have been found to be associated with increased risk of
1178:
1173:
192:
1714:
1621:
1316:
1130:
1125:
225:
174:
17:
1354:
1349:
1145:
246:
1643:
1467:
1460:
1369:
1265:
1260:
1150:
1140:
547:
1280:
263:
1638:
1560:
1409:
1107:
472:
resulting in G to T and C to A substitutions in the genome. In humans, it is primarily repaired by
186:
1336:
1294:
1135:
1082:
1077:
583:
461:
1750:
1660:
1455:
1359:
1311:
1306:
1097:
916:
571:
559:
663:"8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and C→A substitutions"
1516:
1326:
1270:
1227:
1222:
1092:
47:
1433:
490:
156:
1441:
1331:
1321:
1242:
567:
484:
234:
85:
8:
1872:
1851:
1538:
1402:
1237:
1117:
1006:
909:
499:
267:
178:
75:
136:
983:
480:
715:
679:
662:
514:
For comparison here is a standard (non-mutagenic) GC base pair with both bases in the
1734:
1193:
1165:
795:
754:
719:
684:
643:
1877:
963:
785:
746:
711:
674:
635:
591:
355:
214:
1450:
953:
882:
473:
790:
773:
1069:
1019:
1014:
935:
579:
532:
404:
750:
1866:
1762:
1583:
1188:
1183:
1102:
1034:
973:
167:
809:
1698:
1648:
1631:
1578:
1531:
1029:
872:
840:
799:
758:
647:
626:
Kanvah, S.; et al. (2010). "Oxidation of DNA: Damage to
Nucleobases".
723:
688:
528:
1665:
1486:
1425:
1058:
996:
991:
926:
889:
849:
389:
301:
InChI=1/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)
147:
639:
291:
InChI=1S/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12)
1024:
948:
943:
510:
311:
InChI=1/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12)
403:
Except where otherwise noted, data are given for materials in their
1746:
968:
904:
877:
660:
575:
661:
Cheng KC; Cahill DS; Kasai H; Nishimura S; Loeb LA (Jan 5, 1992).
115:
108:
1693:
1445:
978:
958:
899:
867:
862:
614:
587:
469:
465:
201:
1818:
1573:
1526:
1521:
894:
857:
555:
551:
34:
1833:
1828:
1823:
1813:
1806:
1801:
1796:
1791:
1786:
1776:
1771:
1626:
1590:
1511:
1506:
1501:
1491:
1394:
127:
98:
251:
1719:
1675:
1670:
1605:
1600:
1595:
1568:
1548:
1543:
1496:
476:
1481:
1476:
563:
582:. 8-oxoguanine is usually formed by the interaction of
771:
460:) is one of the most common DNA lesions resulting from
546:
The role of the deoxyriboside form of 8-oxoguanine,
63:7,8-Dihydro-8-oxoguanine; 8-Oxo-7,8-dihydroguanine
518:configuration of the bond between base and sugar.
1864:
562:is employed in the removal of 8-oxoguanine from
213:
84:
468:, and can result in a mismatched pairing with
1410:
839:
825:
541:
1417:
1403:
832:
818:
266:
177:
155:
789:
736:
678:
233:
509:
489:
262:
191:
14:
1865:
625:
168:
1398:
813:
701:
294:Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N
135:
550:(abbreviated 8-oxo-dG or 8-OHdG) in
611:8-hydroxyguanine - Compound Summary
314:Key: UBKVUFQGVWHZIR-UHFFFAOYAW
304:Key: CLGFIVUFZRGQRP-UHFFFAOYAZ
204:
24:
1725:Proliferating Cell Nuclear Antigen
1656:Microhomology-mediated end joining
578:including some that contribute to
25:
1889:
522:
1847:
1846:
1740:Meiotic recombination checkpoint
590:base in DNA under conditions of
411:
373:
367:
33:
558:also applies to 8-oxoguanine.
407:(at 25 °C , 100 kPa).
1424:
765:
730:
695:
654:
619:
604:
379:
361:
13:
1:
716:10.1016/s1383-5742(97)00035-5
680:10.1016/S0021-9258(18)48474-8
597:
1622:Transcription-coupled repair
7:
335:O=C2NC=1N\C(=N/C(=O)C=1N2)N
10:
1894:
1644:Non-homologous end joining
1468:Nucleotide excision repair
1461:Poly ADP ribose polymerase
1062:(Nucleoside monophosphate)
542:Cancer, aging, infertility
1842:
1707:
1686:
1614:
1559:
1432:
1345:
1302:
1293:
1256:
1218:
1211:
1164:
1116:
1068:
1057:
1005:
934:
925:
917:Unnatural base pair (UBP)
848:
791:10.1093/carcin/23.11.1911
751:10.1080/10715769800300531
401:
348:
323:
278:
68:
60:
46:
41:
32:
1639:Homology directed repair
1561:Homologous recombination
1295:Nucleoside triphosphate
584:reactive oxygen species
548:8-oxo-2'-deoxyguanosine
462:reactive oxygen species
340:c12=NC(=O)N=c1c(nc2=O)N
1661:Postreplication repair
1456:Uracil-DNA glycosylase
1248:Xanthosine diphosphate
1212:Nucleoside diphosphate
572:oxoguanine glycosylase
560:Oxoguanine glycosylase
519:
507:
479:. It can be caused by
739:Free Radical Research
513:
493:
483:, in connection with
51:2-Amino-7,9-dihydro-1
1767:core protein complex
1442:Base excision repair
568:base excision repair
485:oxidative metabolism
1539:DNA mismatch repair
1118:Deoxyribonucleotide
1007:Deoxyribonucleoside
910:Pyrimidine analogue
570:. As described in
500:Hoogsteen base pair
397: g·mol
29:
566:by the process of
520:
508:
481:ionizing radiation
434:Infobox references
27:
1860:
1859:
1735:Adaptive response
1392:
1391:
1388:
1387:
1289:
1288:
1207:
1206:
1166:Cyclic nucleotide
1053:
1052:
704:Mutation Research
640:10.1021/ar900175a
442:Chemical compound
440:
439:
247:CompTox Dashboard
117:Interactive image
110:Interactive image
55:-purine-6,8-dione
16:(Redirected from
1885:
1850:
1849:
1419:
1412:
1405:
1396:
1395:
1300:
1299:
1216:
1215:
1066:
1065:
987:-Methyladenosine
964:5-Methylcytidine
932:
931:
834:
827:
820:
811:
810:
804:
803:
793:
769:
763:
762:
734:
728:
727:
699:
693:
692:
682:
658:
652:
651:
623:
617:
608:
592:oxidative stress
450:8-hydroxyguanine
424:
418:
415:
414:
396:
381:
375:
369:
363:
356:Chemical formula
271:
270:
255:
253:
237:
217:
206:
195:
193:8-hydroxyguanine
181:
170:
159:
139:
119:
112:
88:
37:
30:
26:
21:
1893:
1892:
1888:
1887:
1886:
1884:
1883:
1882:
1863:
1862:
1861:
1856:
1838:
1708:Other/ungrouped
1703:
1682:
1610:
1555:
1451:DNA glycosylase
1434:Excision repair
1428:
1423:
1393:
1384:
1341:
1285:
1252:
1203:
1160:
1112:
1061:
1049:
1045:Deoxyxanthosine
1001:
954:5-Methyluridine
921:
883:Purine analogue
844:
838:
808:
807:
770:
766:
735:
731:
700:
696:
659:
655:
624:
620:
609:
605:
600:
586:(ROS) with the
544:
525:
474:DNA glycosylase
443:
436:
431:
430:
429: ?)
420:
416:
412:
408:
394:
384:
378:
372:
366:
358:
344:
341:
336:
331:
330:
319:
316:
315:
312:
306:
305:
302:
296:
295:
292:
286:
285:
274:
256:
249:
240:
220:
207:
162:
142:
122:
102:
91:
78:
64:
56:
23:
22:
15:
12:
11:
5:
1891:
1881:
1880:
1875:
1858:
1857:
1855:
1854:
1843:
1840:
1839:
1837:
1836:
1831:
1826:
1821:
1816:
1811:
1810:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1759:
1758:
1753:
1743:
1742:
1737:
1732:
1727:
1722:
1717:
1711:
1709:
1705:
1704:
1702:
1701:
1696:
1690:
1688:
1684:
1683:
1681:
1680:
1679:
1678:
1673:
1663:
1658:
1653:
1652:
1651:
1641:
1636:
1635:
1634:
1629:
1618:
1616:
1615:Other pathways
1612:
1611:
1609:
1608:
1603:
1598:
1593:
1588:
1587:
1586:
1576:
1571:
1565:
1563:
1557:
1556:
1554:
1553:
1552:
1551:
1546:
1536:
1535:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1499:
1494:
1489:
1484:
1479:
1465:
1464:
1463:
1458:
1453:
1438:
1436:
1430:
1429:
1422:
1421:
1414:
1407:
1399:
1390:
1389:
1386:
1385:
1383:
1382:
1377:
1372:
1367:
1362:
1357:
1352:
1346:
1343:
1342:
1340:
1339:
1334:
1329:
1324:
1319:
1314:
1309:
1303:
1297:
1291:
1290:
1287:
1286:
1284:
1283:
1278:
1273:
1268:
1263:
1257:
1254:
1253:
1251:
1250:
1245:
1240:
1235:
1230:
1225:
1219:
1213:
1209:
1208:
1205:
1204:
1202:
1201:
1196:
1191:
1186:
1181:
1176:
1170:
1168:
1162:
1161:
1159:
1158:
1153:
1148:
1143:
1138:
1133:
1128:
1122:
1120:
1114:
1113:
1111:
1110:
1105:
1100:
1095:
1090:
1085:
1080:
1074:
1072:
1070:Ribonucleotide
1063:
1055:
1054:
1051:
1050:
1048:
1047:
1042:
1037:
1032:
1027:
1022:
1020:Deoxyguanosine
1017:
1015:Deoxyadenosine
1011:
1009:
1003:
1002:
1000:
999:
994:
989:
981:
976:
971:
966:
961:
956:
951:
946:
940:
938:
936:Ribonucleoside
929:
923:
922:
920:
919:
914:
913:
912:
907:
902:
897:
887:
886:
885:
880:
875:
870:
865:
854:
852:
846:
845:
837:
836:
829:
822:
814:
806:
805:
784:(11): 1911–8.
778:Carcinogenesis
764:
729:
694:
653:
634:(2): 280–287.
628:Acc. Chem. Res
618:
602:
601:
599:
596:
580:carcinogenesis
543:
540:
533:carcinogenesis
524:
523:In body fluids
521:
441:
438:
437:
432:
410:
409:
405:standard state
402:
399:
398:
392:
386:
385:
382:
376:
370:
364:
359:
354:
351:
350:
346:
345:
343:
342:
339:
337:
334:
326:
325:
324:
321:
320:
318:
317:
313:
310:
309:
307:
303:
300:
299:
297:
293:
290:
289:
281:
280:
279:
276:
275:
273:
272:
264:DTXSID60231515
259:
257:
245:
242:
241:
239:
238:
230:
228:
222:
221:
219:
218:
210:
208:
200:
197:
196:
189:
183:
182:
172:
164:
163:
161:
160:
152:
150:
144:
143:
141:
140:
132:
130:
124:
123:
121:
120:
113:
105:
103:
96:
93:
92:
90:
89:
81:
79:
74:
71:
70:
66:
65:
62:
58:
57:
50:
44:
43:
39:
38:
9:
6:
4:
3:
2:
1890:
1879:
1876:
1874:
1871:
1870:
1868:
1853:
1845:
1844:
1841:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1769:
1768:
1764:
1763:FANC proteins
1761:
1760:
1757:
1754:
1752:
1748:
1745:
1744:
1741:
1738:
1736:
1733:
1731:
1728:
1726:
1723:
1721:
1718:
1716:
1713:
1712:
1710:
1706:
1700:
1697:
1695:
1692:
1691:
1689:
1685:
1677:
1674:
1672:
1669:
1668:
1667:
1664:
1662:
1659:
1657:
1654:
1650:
1647:
1646:
1645:
1642:
1640:
1637:
1633:
1630:
1628:
1625:
1624:
1623:
1620:
1619:
1617:
1613:
1607:
1604:
1602:
1599:
1597:
1594:
1592:
1589:
1585:
1584:RecQ helicase
1582:
1581:
1580:
1577:
1575:
1572:
1570:
1567:
1566:
1564:
1562:
1558:
1550:
1547:
1545:
1542:
1541:
1540:
1537:
1533:
1530:
1528:
1525:
1523:
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1474:
1473:
1469:
1466:
1462:
1459:
1457:
1454:
1452:
1449:
1448:
1447:
1443:
1440:
1439:
1437:
1435:
1431:
1427:
1420:
1415:
1413:
1408:
1406:
1401:
1400:
1397:
1381:
1378:
1376:
1373:
1371:
1368:
1366:
1363:
1361:
1358:
1356:
1353:
1351:
1348:
1347:
1344:
1338:
1335:
1333:
1330:
1328:
1325:
1323:
1320:
1318:
1315:
1313:
1310:
1308:
1305:
1304:
1301:
1298:
1296:
1292:
1282:
1279:
1277:
1274:
1272:
1269:
1267:
1264:
1262:
1259:
1258:
1255:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1221:
1220:
1217:
1214:
1210:
1200:
1197:
1195:
1192:
1190:
1187:
1185:
1182:
1180:
1177:
1175:
1172:
1171:
1169:
1167:
1163:
1157:
1154:
1152:
1149:
1147:
1144:
1142:
1139:
1137:
1134:
1132:
1129:
1127:
1124:
1123:
1121:
1119:
1115:
1109:
1106:
1104:
1101:
1099:
1096:
1094:
1091:
1089:
1086:
1084:
1081:
1079:
1076:
1075:
1073:
1071:
1067:
1064:
1060:
1056:
1046:
1043:
1041:
1038:
1036:
1035:Deoxycytidine
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1013:
1012:
1010:
1008:
1004:
998:
995:
993:
990:
988:
986:
982:
980:
977:
975:
974:Pseudouridine
972:
970:
967:
965:
962:
960:
957:
955:
952:
950:
947:
945:
942:
941:
939:
937:
933:
930:
928:
924:
918:
915:
911:
908:
906:
903:
901:
898:
896:
893:
892:
891:
888:
884:
881:
879:
876:
874:
871:
869:
866:
864:
861:
860:
859:
856:
855:
853:
851:
847:
842:
835:
830:
828:
823:
821:
816:
815:
812:
801:
797:
792:
787:
783:
779:
775:
768:
760:
756:
752:
748:
745:(6): 469–86.
744:
740:
733:
725:
721:
717:
713:
710:(3): 147–63.
709:
705:
698:
690:
686:
681:
676:
673:(1): 166–72.
672:
668:
664:
657:
649:
645:
641:
637:
633:
629:
622:
616:
612:
607:
603:
595:
593:
589:
585:
581:
577:
573:
569:
565:
561:
557:
553:
549:
539:
536:
534:
530:
517:
512:
505:
501:
497:
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28:8-Oxoguanine
19:
1766:
1747:DNA helicase
1730:8-Oxoguanine
1729:
1699:SOS response
1579:RecF pathway
1532:Excinuclease
1040:Deoxyinosine
1030:Deoxyuridine
984:
873:Hypoxanthine
843:constituents
841:Nucleic acid
781:
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742:
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446:8-Oxoguanine
445:
444:
69:Identifiers
61:Other names
52:
18:8-oxoguanine
667:J Biol Chem
529:mutagenesis
349:Properties
175:100.024.578
137:CHEBI:44605
1873:DNA repair
1867:Categories
1687:Regulation
1666:Photolyase
1426:DNA repair
1059:Nucleotide
997:Wybutosine
992:Xanthosine
927:Nucleoside
890:Pyrimidine
850:Nucleobase
598:References
464:modifying
390:Molar mass
235:V5WDN6HY4L
148:ChemSpider
97:3D model (
76:CAS Number
48:IUPAC name
1507:XPG/ERCC5
1492:XPD/ERCC2
1025:Thymidine
949:Guanosine
944:Adenosine
576:mutations
502:with dA (
454:8-oxo-Gua
86:5614-64-2
1852:Category
1502:XPF/DDB1
1497:XPE/DDB1
1189:c-di-AMP
1184:c-di-GMP
969:Cytidine
905:Cytosine
878:Xanthine
800:12419840
759:10098453
648:19938827
494:8-oxoG (
1878:Purines
1694:SOS box
1446:AP site
979:Inosine
959:Uridine
900:Thymine
868:Guanine
863:Adenine
724:9439711
689:1730583
615:PubChem
588:guanine
498:) in a
470:adenine
466:guanine
427:what is
425: (
395:167.128
202:PubChem
1819:FANCD2
1814:FANCD1
1574:RecBCD
1527:RAD23B
1522:RAD23A
895:Uracil
858:Purine
798:
757:
722:
687:
646:
552:cancer
422:verify
419:
328:SMILES
215:119315
157:106574
42:Names
1834:FANCN
1829:FANCJ
1824:FANCI
1807:FANCM
1802:FANCL
1797:FANCG
1792:FANCF
1787:FANCE
1782:FANCC
1777:FANCB
1772:FANCA
1632:ERCC8
1627:ERCC6
1591:RAD51
1512:ERCC1
1199:cGAMP
1194:cADPR
556:aging
458:OHGua
456:, or
283:InChI
128:ChEBI
99:JSmol
1720:PcrA
1676:CRY2
1671:CRY1
1606:LexA
1601:Slx4
1596:Sgs1
1569:RecA
1549:MSH2
1544:MLH1
1472:ERCC
1380:dXTP
1375:dITP
1370:dCTP
1365:dUTP
1360:dTTP
1355:dGTP
1350:dATP
1317:mUTP
1281:dCDP
1276:dUDP
1271:dTDP
1266:dGDP
1261:dADP
1233:mUDP
1179:cGMP
1174:cAMP
1156:dXMP
1151:dIMP
1146:dCMP
1141:dUMP
1136:dTMP
1131:dGMP
1126:dAMP
1088:mUMP
796:PMID
755:PMID
720:PMID
685:PMID
644:PMID
554:and
531:and
516:anti
504:anti
477:OGG1
226:UNII
187:MeSH
1756:WRN
1751:BLM
1715:Ogt
1517:RPA
1487:XPC
1482:XPB
1477:XPA
1337:XTP
1332:ITP
1327:CTP
1322:UTP
1312:GTP
1307:ATP
1243:CDP
1238:UDP
1228:GDP
1223:ADP
1108:XMP
1103:IMP
1098:CMP
1093:UMP
1083:GMP
1078:AMP
786:doi
747:doi
712:doi
708:387
675:doi
671:267
636:doi
564:DNA
496:syn
252:EPA
205:CID
1869::
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1649:Ku
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383:2
380:O
377:5
374:N
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368:H
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362:C
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