629:
is able to reverse the MC-binding to DNA. Lung and kidney tissue are not capable of doing this, which may explain why MC is more carcinogenic in lungs and kidneys than in the liver. To be carcinogenic, the MC metabolite has to be covalently bound to DNA. Therefore, it is necessary for MC to be oxygenated in order to carcinogenic. Injected MC does not move away from the injection site. In a rat body MC has a half-life of about 4 weeks. After 8 weeks, 80% of MC is metabolized into water-soluble metabolites. MC and its metabolites mainly exit the body via feces (a ninefold more urine). Three months after injection with MC, 85% of the rats are reported to have tumors. 82% of the tumors is a form of spindle-cell sarcoma.
638:
adenoid hyperplasia or adenomas, and squamous cell carcinoma occurred in 15 (88.2%), 12 (70.6%) and 3 (17.7%) out of 17 rats respectively. After 60 days, the incidences were 15/18 (83.3%), 4/17 (23.5%) and 7/18 (38.9%). All of the precancerous lesions and carcinomas showed positive expression of gamma-glutamyltranspeptidase (GGT). Jin et al. (2013) found that the cellular redox balance is altered by acute exposure to 3-MC. This causes the nuclear factor erythroid 2-related factor 2 (Nrf2)-regulated response pathway to induce antioxidant responses.
24:
273:
198:
543:
566:
33:
670:
Ah genotype. A single ip injection (in inducible fetal lung supernatants) of 100 mg/kg of 3-MC to the mothers resulted in a maximal 50-fold induction of AHH activity by 8 hr, which persisted for 48 hr. The same injections to adult F1 mice revealed only a 4- to 7—fold increase in lung AHH activity, compared to the large fetal induction ratio.
438:
553:
N,N-diethyl-1-naphthamide (2). At -60 ̊C the reaction of 1 and 2 afforded evenly to the lactone (3), the carbonyl addition product which underwent conversion on treatment with acid. The free acid (4) was obtained when the latter was cleaved reductively with zinc and alkali. Cyclization of the product occurred when treated with ZnCl
532:, its responses and change in response are compared. It is also known that due to genetic mutations, the compound causes cancer cells to develop. In 1982, the last article appeared on the synthesis of methylcholanthrene. The yield of 93% was reached and therefore no further adjustments were made to the synthesis scheme.
492:. This compound forms pale yellow solid crystals when crystallized from benzene and ether. It has a melting point around 180 °C and its boiling point is around 280 °C at a pressure of 80 mmHg. Methylcholanthrene is used in laboratory studies of chemical carcinogenesis. It is an alkylated derivative of
637:
Methylcholanthrene is often used to induce tumors in rodents for carcinogenesis and mutagenesis research. In a study from 1991, lung precancerous and cancerous lesions were induced in Wistar rats by one intrabronchial injection of 3-MC. After 30 days, atypical hyperplasia of bronchiolar epithelium,
628:
MC is metabolized by rat liver microsomes into oxygenated forms which alkylate DNA. These oxygenated metabolites bind to double-stranded and single-stranded. Empirical data show that MC tends to bind mostly to G-bases8. When injected in lung, kidney or liver tissue of rats, it appears that the liver
669:
The administration of 3-MC to pregnant mice results in the formation of lung tumors in the offspring. Miller et al. (1990) compared the effects of fetal versus adult exposure to 3-MC on both induction of aryl hydrocarbon hydroxylase (AHH) activity in lung and dependence of lung tumorigenesis on the
580:
process in rat livers. Inhibition could happen on by interfering in demethylase conformations or by interfering in synthesis and/or degradation of demethylase. Experiments showed that the Km doesn't change after 3-MC treatment. This strongly indicates that enzyme affinity is not influenced by 3-MC.
552:
First 3-MC was synthesized with the method of reference. Later the synthesis of the compound was improved. The synthesis of 3-MC consists of a few steps, visualized in figure 1; the first step is the key to success for the synthesis. 4-methylindanone (1) reacts in condensation with lithium salt of
523:
In 1933, the first article about methylcholanthrene was published. Here they described the synthesis of the compound. Not many years later, it became clear that this compound had toxic properties to humans and animals. Therefore, a lot of interest was shown in the compound and it was used often in
646:
3-MC is a ligand of the aryl hydrocarbon receptor (AhR), which stimulates transcription directed by xenobiotic response elements. AhR ligands can induce formation of an AhR-estrogen receptor (ER) complex. 3-MC was found to elicit estrogenic activity by this mechanism, and by stimulation of the
660:
3-MC is mutagenic to human cells. Curren et al. (1978) were the first to report successfully induced mutations in human cells with 3-MC. Skin epithelial cells are thought to metabolize the compound to mutagenic products. The ability to metabolize mutagens may express genetically regulated
619:
Research on the effect of 3-MC in rat uteri concludes that 3-MC acts as an estrogen antagonist. The sexhormone is, like 3-MC, a polycyclic aromatic hydrocarbon. 3-MC and estrogen bind to estrogenreceptors competitively, reducing the estrogen expression.
600:. The second epoxide is not hydrolysed immediately because it is localized next to a bay region, which shields the epoxide. This way, the metabolite is able to travel and bind to DNA in figure (2). The mechanism is derived from the binding mechanism of
1230:
Hutton JJ, Meier J, Hackney C (January 1979). "Comparison of the in vitro mutagenicity and metabolism of dimethylnitrosamine and benzopyrene in tissues from inbred mice treated with phenobarbital, 3-methylcholanthrene or polychlorinated biphenyls".
615:
There appears to be an equilibrium in 3-MC-free and 3-MC-bound. It is hard to determine how when the equilibrium is formed due to difficulties with radioactive measurements. A probable saturating dose is thought to be around 40 mg 3-MC/kg.
585:. These results point towards inhibition of demethylase synthesis and/or induction of demetylase degradation. Unpublished observations of Venkatesan, Argus and Arcos suggest that demethylase synthesis inhibition is most plausible.
1266:
Miller MS, Jones AB, Park SS, Anderson LM (June 1990). "The formation of 3-methylcholanthrene-initiated lung tumors correlates with induction of cytochrome P450IA1 by the carcinogen in fetal but not adult mice".
1332:
484:
at very high temperatures. Methylcholanthrene is also known as 3-methylcholanthrene, 20-methylcholanthrene or the IUPAC name 3-methyl-1,2-dyhydrobenzoaceanthrylene. The short notation often used is
451:
1325:
661:
differences within a species such as man or mouse, causing environmental chemicals to show a different level of mutagenicity and carcinogenicity to specific individuals.
528:
research. Methylcholanthrene is often tested on mice and rats to derive information for cancer medicine development. Due to the influence of the compound on the
1318:
312:
1146:
Shipley JM, Waxman DJ (June 2006). "Aryl hydrocarbon receptor-independent activation of estrogen receptor-dependent transcription by 3-methylcholanthrene".
1552:
1420:
105:
1001:
Sheen YY, Kim SS, Yun HC (1993). "Effect of 3-methylcholanthrene on rat uterus: Uterine growth and mechanism of action of 3-methylcholanthrene".
557:
in acetic acid anhydride and gave the compound 6-acetoxy-3-MC (5). Reducing this product with hydriodic acid in propionic acid resulted in 3-MC.
822:
Cook JW, Haslewood GA (1934). "The synthesis of 5 : 6-dimethyl-1 : 2-benzanthraquinone, a degradation product of deoxycholic acid".
1305:
914:
Eastman A, Sweetenham J, Bresnick E (December 1978). "Comparison of in vivo and in vitro binding of polycyclic hydrocarbons to DNA".
287:
1099:"Acute exposure to 3-methylcholanthrene induces hepatic oxidative stress via activation of the Nrf2/ARE signaling pathway in mice"
1406:
647:
expression of some endogenous ER target genes. 3-MC may cause respiratory tract irritation, skin irritation or eye irritation.
1430:
605:
477:
771:
Duran-Reynals ML, Stanley B (December 1961). "Vaccinia dermal infection and methylcholanthrene in cortisone-treated mice".
1402:
458:
1520:
230:
856:
Harvey RG, Cortez C, Jacobs SA (1982). "Synthesis of polycyclic aromatic hydrocarbons via a novel annelation method".
251:
1352:
1341:
612:
is used in the figure, since that base appears to be bound to
Benzopyrene far more often than the other bases.
1195:
Curren RD, Homer CJ, Price PJ, Freeman AE (March 1979). "Mutagenesis of human cells by 3-methylcholanthrene".
687:
1425:
415:
193:
529:
296:
InChI=1S/C21H16/c1-13-6-7-15-12-20-17-5-3-2-4-14(17)8-9-18(20)19-11-10-16(13)21(15)19/h2-9,12H,10-11H2,1H3
23:
1547:
155:
1493:
882:"Mechanism of 3-methylcholanthrene-induced inhibition of dimethylnitrosamine demethylase in rat liver"
1542:
1434:
1398:
780:
45:
1503:
1474:
1450:
1181:
574:
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268:
71:
1344:
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1163:
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983:
931:
893:
796:
753:
493:
596:
and another epoxidation, to a very reactive epoxide. Epoxidations are realized by the enzyme
496:
and has a similar UV spectrum. The most common isomer is 3-methylcholanthrene, although the
1379:
1368:
1276:
1240:
1204:
1155:
1110:
1010:
973:
965:
923:
881:
788:
743:
725:
481:
403:
335:
588:
A possible mechanism for this reaction is depicted in figure (2). 3-MC is metabolized, via
239:
1040:
597:
582:
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784:
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81:
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792:
712:
Malins DC, Anderson KM, Gilman NK, Green VM, Barker EA, Hellström KE (July 2004).
701:
Lide DR (2007). "CRC Handbook of
Chemistry and Physics 88th Edition". p. 173.
32:
219:
1461:
589:
577:
504:
503:
3-Methylcholanthrene, a known carcinogen which builds up in the prostate due to
1159:
718:
Proceedings of the
National Academy of Sciences of the United States of America
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1375:
1371:
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1414:
1306:
National
Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
1252:
1216:
969:
935:
512:
1395:
1014:
739:
372:
206:
1115:
1098:
1072:
Zhongguo Yi Xue Ke Xue Yuan Xue Bao. Acta
Academiae Medicinae Sinicae
146:
428:
Except where otherwise noted, data are given for materials in their
581:
Instead, incubation with 3-MC leads to a decrease in the amount of
837:
Jacobs SA, Harvey RG (1981). "Synthesis of 3-methylcholanthrene".
564:
541:
126:
104:
94:
714:"Development of a cancer DNA phenotype prior to tumor formation"
1314:
1097:
Jin Y, Miao W, Lin X, Pan X, Ye Y, Xu M, Fu Z (December 2014).
954:"3-Methylcholanthrene uptake and metabolism in organ culture"
256:
909:
907:
947:
945:
604:
to DNA. This is likely because it is plausible that two
446:
875:
873:
871:
1041:"A study of the metabolism of 20-methylcholanthrene"
1351:
1353:
952:Lasnitzki I, Bard DR, Franklin HR (August 1975).
880:Venkatesan N, Argus MF, Arcos JC (October 1970).
218:
80:
1034:
1032:
1326:
8:
1333:
1319:
1311:
320:CC1=C2CCC3=C2C(=CC4=C3C=CC5=CC=CC=C54)C=C1
271:
196:
174:
15:
1114:
977:
747:
729:
238:
409:not, but in xylene, toluene and benzene
50:3-Methyl-1,2-dihydrocyclopentatetraphene
679:
317:
292:
267:
608:are metabolized via the same pathway.
397:280 °C (536 °F; 553 K)
387:180 °C (356 °F; 453 K)
187:
573:3-MC has an inhibitory function in a
299:Key: PPQNQXQZIWHJRB-UHFFFAOYSA-N
154:
134:
7:
1184:. U.S. National Library of Medicine.
1269:Toxicology and Applied Pharmacology
1148:Toxicology and Applied Pharmacology
209:
546:1. Synthesis of methylcholanthrene
14:
1426:Modified low-density lipoproteins
1358:Tooltip Aryl hydrocarbon receptor
1039:Dauben WG, Mabee D (March 1951).
511:. It "readily produces" primary
1553:Polycyclic aromatic hydrocarbons
1431:Polycyclic aromatic hydrocarbons
858:The Journal of Organic Chemistry
606:polycyclic aromatic hydrocarbons
436:
31:
22:
916:Chemico-Biological Interactions
824:Journal of the Chemical Society
478:polycyclic aromatic hydrocarbon
432:(at 25 °C , 100 kPa).
1403:polychlorinated dibenzodioxins
1003:Archives of Pharmacal Research
569:2.Methylcholanthrene mechanism
1:
1521:Receptor/signaling modulators
793:10.1126/science.134.3494.1984
359:268.35174 g/mol
1281:10.1016/0041-008x(90)90298-9
1245:10.1016/0165-1218(79)90010-7
1209:10.1016/0027-5107(79)90214-8
928:10.1016/0009-2797(78)90095-9
507:breakdown, is implicated in
500:can occur in other places.
377:1.28 g/cu cm at 20 °C
1569:
1160:10.1016/j.taap.2005.09.011
665:Non-human toxicity studies
1512:
1342:Aryl hydrocarbon receptor
1070:He R (October 1991). "".
958:British Journal of Cancer
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308:
283:
64:
56:
44:
39:
30:
21:
1103:Environmental Toxicology
731:10.1073/pnas.0403888101
416:Magnetic susceptibility
1457:Tapinarof (benvitimod)
688:"3-methylcholanthrene"
570:
547:
530:central nervous system
1399:aromatic hydrocarbons
568:
545:
59:20–Methylcholanthrene
17:3-Methylcholanthrene
1435:3-methylcholanthrene
970:10.1038/bjc.1975.152
480:produced by burning
46:Preferred IUPAC name
1504:Cyproterone acetate
1386:Dietary carotenoids
839:Tetrahedron Letters
785:1961Sci...134.1984D
779:(3494): 1984–1985.
724:(29): 10721–10725.
575:dimethylnitrosamine
404:Solubility in water
18:
1015:10.1007/bf02977516
651:Effects on animals
571:
548:
471:Methylcholanthrene
459:Infobox references
367:Pale yellow solid
16:
1530:
1529:
1494:7-Ketocholesterol
1233:Mutation Research
1197:Mutation Research
1116:10.1002/tox.21870
1109:(12): 1399–1408.
892:(10): 2556–2562.
482:organic compounds
467:Chemical compound
465:
464:
252:CompTox Dashboard
106:Interactive image
1560:
1451:β-naphthoflavone
1380:prostaglandin G2
1369:Arachidonic acid
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864:(11): 2120–2125.
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598:cytochrome P450
583:enzyme activity
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538:
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509:prostate cancer
468:
461:
456:
455:
454: ?)
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441:
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433:
422:-194·10 cm/mol
419:
406:
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344:
338:
324:
321:
316:
315:
304:
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291:
290:
279:
261:
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212:
181:
161:
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120:
111:
98:
87:
74:
60:
52:
51:
12:
11:
5:
1566:
1564:
1556:
1555:
1550:
1545:
1535:
1534:
1528:
1527:
1525:
1524:
1517:
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1510:
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1507:
1506:
1501:
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1487:
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1428:
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1418:
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1300:External links
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1203:(1): 109–113.
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625:
622:
610:Deoxyguanosine
562:
559:
554:
550:
549:
537:
534:
520:
517:
494:benzanthracene
466:
463:
462:
457:
435:
434:
430:standard state
427:
424:
423:
420:
414:
411:
410:
407:
402:
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398:
395:
389:
388:
385:
379:
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123:
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117:
116:Abbreviations
113:
112:
110:
109:
101:
99:
92:
89:
88:
86:
85:
77:
75:
70:
67:
66:
62:
61:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1565:
1554:
1551:
1549:
1546:
1544:
1541:
1540:
1538:
1523:
1522:
1518:
1515:
1514:
1511:
1505:
1502:
1500:
1497:
1495:
1492:
1489:
1488:
1484:
1480:
1476:
1473:
1470:
1467:
1463:
1460:
1458:
1455:
1452:
1448:
1447:benzoflavones
1444:
1440:
1436:
1432:
1429:
1427:
1424:
1422:
1419:
1416:
1412:
1411:dibenzofurans
1408:
1404:
1400:
1397:
1394:
1392:
1389:
1387:
1384:
1381:
1377:
1373:
1370:
1367:
1364:
1363:
1361:
1356:
1350:
1346:
1343:
1336:
1331:
1329:
1324:
1322:
1317:
1316:
1313:
1307:
1304:
1303:
1299:
1290:
1286:
1282:
1278:
1274:
1270:
1262:
1259:
1254:
1250:
1246:
1242:
1238:
1234:
1226:
1223:
1218:
1214:
1210:
1206:
1202:
1198:
1191:
1188:
1183:
1177:
1174:
1169:
1165:
1161:
1157:
1153:
1149:
1142:
1139:
1134:
1130:
1126:
1122:
1117:
1112:
1108:
1104:
1100:
1093:
1090:
1085:
1081:
1077:
1073:
1066:
1063:
1058:
1054:
1050:
1046:
1042:
1035:
1033:
1029:
1024:
1020:
1016:
1012:
1008:
1004:
997:
994:
989:
985:
980:
975:
971:
967:
963:
959:
955:
948:
946:
942:
937:
933:
929:
925:
921:
917:
910:
908:
904:
899:
895:
891:
887:
883:
876:
874:
872:
868:
863:
859:
852:
849:
844:
840:
833:
830:
825:
818:
815:
810:
806:
802:
798:
794:
790:
786:
782:
778:
774:
767:
764:
759:
755:
750:
745:
741:
737:
732:
727:
723:
719:
715:
708:
705:
697:
694:
689:
683:
680:
673:
671:
664:
662:
655:
650:
648:
641:
639:
632:
630:
623:
621:
617:
613:
611:
607:
603:
599:
595:
591:
586:
584:
579:
576:
567:
560:
558:
544:
540:
539:
535:
533:
531:
527:
526:toxicological
518:
516:
514:
510:
506:
501:
499:
495:
491:
487:
483:
479:
476:
472:
460:
453:
448:
431:
425:
421:
417:
413:
412:
408:
405:
401:
400:
396:
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188:ECHA InfoCard
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20:
1548:Hepatotoxins
1519:
1491:Antagonists:
1490:
1462:Tetrapyroles
1365:
1272:
1268:
1261:
1239:(1): 75–94.
1236:
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1200:
1196:
1190:
1176:
1154:(2): 87–97.
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845:: 1093–1096.
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498:methyl group
489:
485:
475:carcinogenic
473:is a highly
470:
469:
65:Identifiers
57:Other names
1543:Carcinogens
1475:derivatives
1439:benzopyrene
1396:Halogenated
1372:metabolites
602:benzopyrene
590:epoxidation
578:demethylase
505:cholesterol
364:Appearance
329:Properties
194:100.000.252
156:ChEMBL40583
136:CHEBI:34342
1537:Categories
1479:indigo dye
1472:Tryptophan
1376:lipoxin A4
1345:modulators
1009:(4): 276.
674:References
624:Metabolism
594:hydrolysis
355:Molar mass
240:214U33M1RL
167:ChemSpider
93:3D model (
72:CAS Number
1499:CH-223191
1483:indirubin
1466:bilirubin
1415:biphenyls
1391:Flutamide
1366:Agonists:
561:Mechanism
536:Synthesis
515:in mice.
1516:See also
1182:"TOXNET"
1168:16257430
1125:23712962
1057:14821965
1023:95829643
809:40961133
801:13888610
758:15249662
642:Toxicity
633:Efficacy
513:sarcomas
418:(χ)
1477:(e.g.,
1464:(e.g.,
1449:(e.g.,
1433:(e.g.,
1405:(e.g.,
1401:(e.g.,
1374:(e.g.,
1289:2363175
1133:6071670
1084:1686852
988:1240005
979:2024855
898:5474178
781:Bibcode
773:Science
740:3372726
519:History
452:what is
450: (
373:Density
349:
207:PubChem
82:56-49-5
1287:
1253:106274
1251:
1217:431552
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1021:
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936:719814
934:
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749:490001
746:
738:
447:verify
444:
313:SMILES
147:ChEMBL
121:20-MC
40:Names
1129:S2CID
1019:S2CID
805:S2CID
736:JSTOR
288:InChI
127:ChEBI
95:JSmol
1407:TCDD
1285:PMID
1249:PMID
1213:PMID
1164:PMID
1121:PMID
1080:PMID
1053:PMID
984:PMID
932:PMID
894:PMID
797:PMID
754:PMID
486:3-MC
231:UNII
220:1674
176:1611
119:3-MC
1421:ΙΤΕ
1409:),
1354:AhR
1277:doi
1273:104
1241:doi
1205:doi
1156:doi
1152:213
1111:doi
1011:doi
974:PMC
966:doi
924:doi
789:doi
777:134
744:PMC
726:doi
722:101
490:MCA
488:or
257:EPA
210:CID
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345:H
341:C
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