title: Mutagenicity of isomeric diol-epoxides of benzo[a]pyrene and benz[a]anthracene in S. typhimurium TA98 and TA100 and in V79 Chinese hamster cells.
abstract: Pairs of isomeric vicinal diol-epoxides derived from benzo[a]pyrene 7,8- and 9,10-dihydrodiols and from benz[a]anthracene 8,9-dihydrodiol were tested for their abilities to revert salmonella typhimurium strains TA98 and TA100 to histidine prototrophy and to induce the formation of 8-azaguanine- or of ouabain-resistant V79 Chinese hamster cells. All six diol-epoxides were active in both bacterial strains, but 7beta,8alpha-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (the syn isomer) was considerably more mutagenic than the other diol-epoxides. Within the three pairs of stereo-isomeric diol-epoxides, the ratio of the mutagenic potencies of the syn over the related anti isomers varied bothwith the chemical structure and the bacterial strain. The half lives of hydration of these diol-epoxides at pH 7.4 were inversely related to their mutagenic potencies in bacteria. In V79 cells, the two benzo[a]pyrene 7,8-diol 9,10-oxides were mutagenic and the anti isomer was more active than the syn isomer; a reversed order of mutagenic potency with these stereo isomers was observed in S. typhimurium. The other four diol-epoxides were non-mutagenic in V79 cells at the concentrations tested.
mesh_terms: D001551:Benz(a)Anthracenes / Q000494:pharmacology*; D001580:Benzopyrenes / Q000494:pharmacology*; D002460:Cell Line; D004852:Epoxy Compounds / Q000494:pharmacology*; D004988:Ethers, Cyclic / Q000494:pharmacology*; D006639:Histidine / Q000378:metabolism; D009153:Mutagens; D009154:Mutation / Q000187:drug effects; D012486:Salmonella typhimurium / Q000187:drug effects*
chemical_list: D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D009153:Mutagens; D006639:Histidine