Comparative tumorigenicity in newborn mice of chrysene- and 5-alkylchrysene-1,2-diol-3,4-epoxides.
We determined the tumorigenicity in newborn mice of racemic anti-1,2-diol-3,4-epoxides of chrysene, 5-methylchrysene, 5-ethylchrysene and 5-propylchrysene. Among the four diol epoxides, only anti-5-methylchrysene-1,2-diol-3,4-epoxide was highly tumorigenic. It was 15-30 times more potent in induction of pulmonary tumors than the other compounds. The results demonstrate that molecular shape is critical in determining the tumorigenic activity of alkylchrysene diol epoxides. A methyl group in the same bay region as the epoxide ring leads to exceptional activity. This may be a consequence of DNA adduct conformation.
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Division of Chemical Carcinogenesis, American Health Foundation, Valhalla, New York.
Misra
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Braley
J
J
Hecht
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SS
D000236:Adenoma / Q000139:chemically induced*; D000818:Animals; D000831:Animals, Newborn; D002273:Carcinogens; D002911:Chrysenes / Q000633:toxicity*; D004852:Epoxy Compounds / Q000633:toxicity*; D008113:Liver Neoplasms / Q000139:chemically induced*; D008175:Lung Neoplasms / Q000139:chemically induced*; D051379:Mice; D008813:Mice, Inbred ICR; D009690:Nucleic Acid Conformation; D013237:Stereoisomerism
D002273:Carcinogens; D002911:Chrysenes; D004852:Epoxy Compounds; C037783:1,2-dihydroxy-epoxy-1,2,3,4-tetrahydro-5-methylchrysene