Comparison of the tumor-initiating activities of benzo(a)pyrene arene oxides and diol-epoxides.
The ability of arene oxides, and diol epoxides of benzo(a)pyrene to initiate skin tumors in mice was determined by using a two-stage system of tumorigenesis. (+/-)-7beta,8alpha-Dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene was a more effective tumor initiator than was (+/-)-7beta,8alpha-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene when applied topically to CD-1 mice and then followed by twice-weekly applications of the promotor 12-O-tetradecanoylphorbol-13-acetate. (+/-)-7beta,8alpha-Dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene was approximately 20 to 30% as active as benzo(a)pyrene was as a tumor initiator. (+/-)-7beta,8alpha-Dihydroxy-7beta,8beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene, benzo(a)pyrene, 9,10-oxide, and benzo(a)pyrene 11, 12-oxide, possessed about 1, 2, and 10%, respectively, of the tumor-initiating activity of benzo(a)pyrene.
D000818:Animals; D001580:Benzopyrenes / Q000633:toxicity*; D004852:Epoxy Compounds / Q000633:toxicity; D005260:Female; D006018:Glycols / Q000633:toxicity; D051379:Mice; D009374:Neoplasms, Experimental / Q000139:chemically induced; D010087:Oxides / Q000633:toxicity; D010212:Papilloma / Q000139:chemically induced*; D012878:Skin Neoplasms / Q000139:chemically induced*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013755:Tetradecanoylphorbol Acetate
D001580:Benzopyrenes; D004852:Epoxy Compounds; D006018:Glycols; D010087:Oxides; D013755:Tetradecanoylphorbol Acetate