277:
164:
462:
33:
24:
1271:
Paoletti, C; Le Pecq, J B; Dat-Xuong, N; Juret, P; Garnier, H; Amiel, J L; Rouesse, J (1980). "Antitumor
Activity, Pharmacology, and Toxicity of Ellipticines, Ellipticinium, and 9-Hydroxy Derivatives: Preliminary Clinical Trials of 2-Methyl-9-Hydroxy Ellipticinium (NSC 264-137)".
1341:
Stiborová, M; Poljaková, J; Martínková, E; Ulrichová, J; Šimánek, V; Dvořák, Z; Frei, E (2012). "Ellipticine oxidation and DNA adduct formation in human hepatocytes is catalyzed by human cytochromes P450 and enhanced by cytochrome
442:
805:
Sbai, M; Ait
Lyazidi, S; Lerner, D A; del Castillo, B; Martin, M A (1996). "Use of micellar media for the fluorimetric determination of ellipticine in aqueous solutions".
647:, capable of entering a DNA strand between base pairs. In its intercalated state, ellipticine binds strongly and lies parallel to the base pairs, increasing the
1410:
313:
1224:"Topoisomerase II binds to ellipticine in the absence or presence of DNA. Characterization of enzyme–drug interactions by fluorescence spectroscopy"
101:
663:, inhibiting the enzyme and resulting in powerful antitumour activity. In clinical trials, ellipticine derivatives have been observed to induce
1289:
1420:
1430:
291:
1400:
1415:
1098:
423:
529:
644:
569:
498:
484:
234:
255:
1435:
1395:
171:
1099:"The anticancer agent ellipticine unwinds DNA by intercalative binding in an orientation parallel to base pairs"
159:
560:
1440:
915:
632:
470:
461:
454:
780:
742:
Miller, R B; Dugar, S (1989). "A regiospecific total synthesis of ellipticine via nitrene insertion".
1113:
664:
45:
272:
1405:
494:
67:
1315:
614:
554:
1425:
1371:
1363:
1303:
1295:
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1253:
1245:
1204:
1186:
1147:
1139:
1076:
1068:
1037:
1019:
978:
970:
935:
830:
822:
759:
692:
300:
InChI=1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3
1355:
1277:
1235:
1194:
1178:
1129:
1121:
1027:
1009:
962:
927:
894:
814:
751:
652:
585:
565:
406:
336:
1167:"Ellipticine increases the superhelical density of intracellular SV40 DNA by intercalation"
953:
Auclair, C (1987). "Multimodal action of antitumor agents on DNA: The ellipticine series".
502:
243:
1327:
714:
660:
276:
163:
141:
77:
1117:
853:
1032:
997:
523:
121:
1199:
1166:
818:
755:
32:
1389:
966:
648:
628:
395:
152:
1056:
514:
684:
602:
490:
1281:
223:
608:
1359:
1125:
718:
711:
707:
700:
364:
132:
1367:
1299:
1249:
1240:
1223:
1190:
1182:
1143:
1072:
1023:
1014:
974:
939:
826:
763:
624:
596:
1375:
1151:
1041:
1307:
1257:
1208:
1080:
982:
834:
918:; Iacobucci, G A; Hochstein, I A (1959). "The synthesis of ellipticine".
680:
672:
590:
545:
1134:
931:
898:
23:
722:
696:
619:
385:
210:
172:
1222:
Froelich-Ammon, S J; Patchan, M W; Osheroff, N; Thompson, R B (1995).
1276:. Recent Results in Cancer Research. Vol. 74. pp. 107–123.
676:
668:
656:
522:
Except where otherwise noted, data are given for materials in their
198:
688:
476:
112:
100:
90:
671:
growth, but are not used for medical purposes due to their high
549:
510:
189:
631:
which gives the alkaloid its name, in 1959, and synthesised by
573:
1055:
Kohn, K W; Waring, M J; Glaubiger, D; Friedman, C A (1975).
506:
260:
881:
Goodwin, S; Smith, A F; Horning, E C (1959). "Alkaloids of
706:
Further DNA damage results from the formation of covalent
998:"Anticancer Alkaloids from Trees: Development into Drugs"
1092:
1090:
910:
908:
651:
of the DNA. Intercalated ellipticine binds directly to
876:
874:
710:
following enzymatic activation of ellipticine by with
1097:
Canals, A; Purciolas, M; Aymamí, J; Coll, M (2005).
400:316–318 °C (601–604 °F; 589–591 K)
807:Journal of Pharmaceutical and Biomedical Analysis
222:
76:
775:
773:
721:, meaning that ellipticine is classified as a
1057:"Intercalative Binding of Ellipticine to DNA"
8:
588:present in several trees within the genera
275:
162:
140:
15:
1239:
1198:
1133:
1031:
1013:
848:
846:
844:
242:
920:Journal of the American Chemical Society
887:Journal of the American Chemical Society
955:Archives of Biochemistry and Biophysics
734:
321:CC1=C2C(=C(C3=C1C=CN=C3)C)C4=CC=CC=C4N2
318:
296:
271:
1323:
1313:
153:
120:
7:
1274:Cancer Chemo- and Immunopharmacology
1411:Heterocyclic compounds with 4 rings
213:
197:
854:"Ellipticine | C17H14N2 - PubChem"
14:
580:Natural occurrence and synthesis
460:
354:
348:
31:
22:
1228:Journal of Biological Chemistry
526:(at 25 °C , 100 kPa).
424:Occupational safety and health
342:
1:
819:10.1016/S0731-7085(96)01759-1
756:10.1016/S0040-4039(00)95184-0
623:, a flowering tree native to
612:. It was first isolated from
1282:10.1007/978-3-642-81488-4_15
967:10.1016/0003-9861(87)90463-2
564:, which inhibits the enzyme
1457:
1421:DNA replication inhibitors
380:Yellow crystalline powder
1360:10.1016/j.tox.2012.08.004
1165:Chu, Y; Hsu, M T (1992).
1126:10.1107/S0907444905015404
520:
441:
421:
416:
329:
309:
287:
60:
44:
39:
30:
21:
1431:Topoisomerase inhibitors
1241:10.1074/jbc.270.25.14998
1106:Acta Crystallographica D
1015:10.4103/0973-7847.194047
781:"Ellipticine | 519-23-3"
485:Precautionary statements
675:; side effects include
643:Ellipticine is a known
1401:Isoquinoline alkaloids
1183:10.1093/nar/20.15.4033
1171:Nucleic Acids Research
561:Rauvolfia sandwicensis
1416:Nitrogen heterocycles
1002:Pharmacognosy Reviews
695:, mouth dryness, and
635:later the same year.
633:Robert Burns Woodward
570:intercalative binding
548:first extracted from
649:superhelical density
46:Preferred IUPAC name
1234:(25): 14998–15004.
1118:2005AcCrD..61.1009C
932:10.1021/ja01525a085
899:10.1021/ja01517a031
744:Tetrahedron Letters
639:Biological activity
407:Solubility in water
372: g·mol
18:
883:Ochrosia elliptica
699:of the tongue and
615:Ochrosia elliptica
584:Ellipticine is an
555:Ochrosia elliptica
530:Infobox references
16:
1436:DNA intercalaters
1291:978-3-642-81490-7
1177:(15): 4033–4038.
926:(16): 4434–4435.
622:
544:is a tetracyclic
538:Chemical compound
536:
535:
471:Hazard statements
256:CompTox Dashboard
102:Interactive image
1448:
1396:Indole alkaloids
1380:
1379:
1354:(2–3): 233–241.
1338:
1332:
1331:
1325:
1321:
1319:
1311:
1268:
1262:
1261:
1243:
1219:
1213:
1212:
1202:
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1156:
1155:
1137:
1112:(7): 1009–1012.
1103:
1094:
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1084:
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1046:
1045:
1035:
1017:
996:Isah, T (2016).
993:
987:
986:
950:
944:
943:
912:
903:
902:
893:(8): 1903–1908.
878:
869:
868:
866:
865:
850:
839:
838:
802:
796:
795:
793:
792:
777:
768:
767:
739:
653:topoisomerase II
618:
586:organic compound
566:topoisomerase II
516:
512:
508:
504:
500:
496:
492:
478:
464:
390:1.257±0.06 g/cm
371:
356:
350:
344:
337:Chemical formula
280:
279:
264:
262:
246:
226:
215:
201:
174:
166:
155:
144:
124:
104:
80:
54:-pyridocarbazole
35:
26:
19:
1456:
1455:
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1446:
1445:
1386:
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1312:
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1216:
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1096:
1095:
1088:
1061:Cancer Research
1054:
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803:
799:
790:
788:
779:
778:
771:
741:
740:
736:
731:
661:DNA replication
641:
582:
552:of the species
539:
532:
527:
487:
473:
457:
434:
409:
369:
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353:
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127:
107:
94:
83:
70:
56:
55:
50:5,11-Dimethyl-6
12:
11:
5:
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1438:
1433:
1428:
1423:
1418:
1413:
1408:
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1388:
1387:
1382:
1381:
1343:
1333:
1324:|journal=
1290:
1263:
1214:
1157:
1086:
1047:
988:
945:
904:
870:
840:
813:(8): 959–965.
797:
769:
750:(3): 297–300.
733:
732:
730:
727:
640:
637:
581:
578:
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534:
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524:standard state
521:
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273:DTXSID30199855
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1058:
1051:
1048:
1043:
1039:
1034:
1029:
1025:
1021:
1016:
1011:
1008:(20): 90–99.
1007:
1003:
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992:
989:
984:
980:
976:
972:
968:
964:
960:
956:
949:
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921:
917:
916:Woodward, R B
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738:
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728:
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724:
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694:
691:, pronounced
690:
686:
682:
678:
674:
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662:
658:
654:
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646:
638:
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634:
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629:New Caledonia
626:
621:
617:
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579:
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531:
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431:
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396:Melting point
394:
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154:ECHA InfoCard
151:
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29:
25:
20:
1441:Plant toxins
1351:
1347:
1336:
1273:
1266:
1231:
1227:
1217:
1174:
1170:
1160:
1135:10261/108793
1109:
1105:
1067:(1): 71–76.
1064:
1060:
1050:
1005:
1001:
991:
958:
954:
948:
923:
919:
890:
886:
882:
862:. Retrieved
857:
810:
806:
800:
789:. Retrieved
785:ChemicalBook
784:
747:
743:
737:
705:
685:hypertension
659:involved in
645:intercalator
642:
613:
607:
603:Aspidosperma
601:
595:
589:
583:
559:
553:
541:
540:
443:
433:Main hazards
422:
61:Identifiers
51:
17:Ellipticine
961:(1): 1–14.
719:peroxidases
712:cytochromes
708:DNA adducts
609:Apocynaceae
542:Ellipticine
427:(OHS/OSH):
377:Appearance
330:Properties
160:100.007.514
1406:Carbazoles
1390:Categories
1348:Toxicology
864:2017-05-30
791:2017-05-30
729:References
701:oesophagus
455:Pictograms
365:Molar mass
244:117VLW7484
133:ChemSpider
122:CHEBI:4776
89:3D model (
68:CAS Number
1368:0300-483X
1326:ignored (
1316:cite book
1300:0080-0015
1250:0021-9258
1191:0305-1048
1144:0907-4449
1073:0008-5472
1024:0973-7847
975:0003-9861
940:0002-7863
885:Labill".
827:0731-7085
764:0040-4039
665:remission
625:Australia
597:Rauvolfia
499:P301+P310
446:labelling
412:Very low
181:208-264-0
173:EC Number
1426:Prodrugs
1376:22917556
1152:15983425
1042:28082790
681:vomiting
673:toxicity
591:Ochrosia
546:alkaloid
417:Hazards
78:519-23-3
1308:7003658
1258:7797481
1209:1324474
1114:Bibcode
1081:1109798
1033:5214563
983:3318697
858:PubChem
835:8818001
723:prodrug
697:mycosis
693:fatigue
620:Labill.
386:Density
370:246.313
211:PubChem
1374:
1366:
1306:
1298:
1288:
1256:
1248:
1207:
1200:334084
1197:
1189:
1150:
1142:
1079:
1071:
1040:
1030:
1022:
981:
973:
938:
860:. 2016
833:
825:
787:. 2016
762:
677:nausea
669:tumour
657:enzyme
606:, and
437:toxic
314:SMILES
199:C09154
40:Names
1102:(PDF)
689:cramp
655:, an
550:trees
292:InChI
113:ChEBI
91:JSmol
1372:PMID
1364:ISSN
1328:help
1304:PMID
1296:ISSN
1286:ISBN
1254:PMID
1246:ISSN
1205:PMID
1187:ISSN
1148:PMID
1140:ISSN
1077:PMID
1069:ISSN
1038:PMID
1020:ISSN
979:PMID
971:ISSN
936:ISSN
831:PMID
823:ISSN
760:ISSN
717:and
715:P450
679:and
627:and
568:via
558:and
515:P501
511:P405
507:P330
503:P321
495:P270
491:P264
477:H301
235:UNII
224:3213
190:KEGG
142:3100
1356:doi
1352:302
1346:".
1278:doi
1236:doi
1232:270
1195:PMC
1179:doi
1130:hdl
1122:doi
1028:PMC
1010:doi
963:doi
959:259
928:doi
895:doi
815:doi
752:doi
667:of
574:DNA
572:to
444:GHS
261:EPA
214:CID
1392::
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942:.
930::
901:.
897::
867:.
837:.
817::
794:.
766:.
754::
358:2
355:N
349:H
343:C
263:)
259:(
93:)
52:H
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