title: Benzo(a)pyrene metabolism in mouse epidermis. Analysis by high pressure liquid chromatography and DNA binding.
abstract: Mouse epidermal homogenates contain an inducible aryl hydrocarbon hydroxylase (AHH) complex that catalyzes the formation of benzo(a)pyrene-7,8-dihydrodiol from benzo(a)pyrene (BP) as assessed by high pressure liquid chromatography (HPLC). 5,6-Benzoflavone (5,6-BF), 7,8-benzoflavone (7,8-BF) and 17-beta-estradiol decreased and butylated hydroxytoluene (BHT) enhanced oxidative metabolism of BP when added in vitro. Epoxide hydrase activity (hydration of benzo(a)pyrene-4,5-epoxide) (BP-4,5-epoxide) was enhanced by 17-beta-estradiol, 5,6-BF, and 7,8-BF. BHT exhibited no significant effect and 1,2-epoxy-3,3,3-trichloropropane (TCPO) inhibited hydrase activity. The capacity of epidermal homogenates to catalyze the covalent binding of BP to DNA indicated that addition of both 5,6-BF and 7,8-BF decreased binding. BHT and TCPO did not significantly affect DNA-binding.
mesh_terms: D000818:Animals; D001189:Aryl Hydrocarbon Hydroxylases / Q000378:metabolism; D001578:Benzopyrans / Q000378:metabolism*; D001665:Binding Sites; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000378:metabolism*; D004851:Epoxide Hydrolases / Q000378:metabolism; D004852:Epoxy Compounds / Q000494:pharmacology; D004958:Estradiol / Q000494:pharmacology; D005260:Female; D005419:Flavonoids / Q000494:pharmacology; D008748:Methylcholanthrene / Q000494:pharmacology; D051379:Mice; D010636:Phenols / Q000378:metabolism; D011407:Propane / Q000031:analogs & derivatives / Q000494:pharmacology; D011809:Quinones / Q000378:metabolism; D012867:Skin / Q000378:metabolism
chemical_list: D001578:Benzopyrans; D004852:Epoxy Compounds; D005419:Flavonoids; D010636:Phenols; D011809:Quinones; D002084:Butylated Hydroxytoluene; D004958:Estradiol; D008748:Methylcholanthrene; D004247:DNA; D001189:Aryl Hydrocarbon Hydroxylases; D004851:Epoxide Hydrolases; D011407:Propane