Metabolism of polycyclic aromatic hydrocarbon derivatives to ultimate carcinogens during lipid peroxidation.
Lipid peroxidation triggered by ascorbate or reduced nicotinamide adenine dinucleotide in rat liver microsomes can initiate the epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene. The stereochemistry of epoxidation is indicative of a peroxide-dependent free radical process. Since the epoxides formed may be the most carcinogenic derivatives of benzo[a]pyrene yet identified, lipid peroxidation can effect the metabolic activation of proximate carcinogens to ultimate carcinogens.
D000818:Animals; D001564:Benzo(a)pyrene; D001580:Benzopyrenes / Q000378:metabolism; D002273:Carcinogens / Q000378:metabolism*; D004101:Dihydroxydihydrobenzopyrenes; D004852:Epoxy Compounds / Q000378:metabolism; D008054:Lipid Peroxides / Q000378:metabolism*; D008862:Microsomes, Liver / Q000378:metabolism; D009249:NADP / Q000378:metabolism; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000378:metabolism*; D051381:Rats
D001580:Benzopyrenes; D002273:Carcinogens; D004101:Dihydroxydihydrobenzopyrenes; D004852:Epoxy Compounds; D008054:Lipid Peroxides; D011083:Polycyclic Compounds; C017228:benzo(a)pyrene 7,8-dihydrodiol; D001564:Benzo(a)pyrene; D009249:NADP