Mutagenicity of the optical isomers of the diastereomeric bay-region chrysene 1,3-diol-3,4-epoxides in bacterial and mammalian cells.
The mutagenic activities of the four optically pure (+)- and (-)-enantiomers of the two diastereomeric bay-region chrysene 1,2-diol-3,4-epoxides were evaluated in histidine-dependent strains of Salmonella typhimurium and in cultured Chinese hamster V79 cells. In strain TA98 of S. typhimurium, (-)-1 alpha, 2 beta-dihydroxy-3 beta, 4 beta-epoxy-1,2,3,4-tetrahydrochrysene was 5 to 10 times more active than the other three optical isomers. However, in strain TA100 of S. typhimurium and in Chinese hamster V79 cells, (+)-1 beta, 2 alpha-dihydroxy-3 alpha, 4 alpha-epoxy-1,2,3,4-tetrahydrochrysene was the most mutagenic diol-epoxide and was from 5 to 40 times more active than the other three optical isomers. The bay-region (+)- and (-)-3,4-epoxy-1,2,3,4-tetrahydrochrysene isomers has identical mutagenic activities in all three systems. These studies indicate that the presence and orientation of the hydroxyl groups play an important role in modulating the mutagenic activity of bay-region epoxides of chrysene in both bacterial and mammalian cells.
D000818:Animals; D001711:Biotransformation; D002460:Cell Line; D002911:Chrysenes / Q000494:pharmacology*; D006224:Cricetinae; D003412:Cricetulus; D004851:Epoxide Hydrolases / Q000378:metabolism; D008168:Lung; D009152:Mutagenicity Tests; D009154:Mutation; D010616:Phenanthrenes / Q000494:pharmacology*; D051381:Rats; D012486:Salmonella typhimurium / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002911:Chrysenes; D010616:Phenanthrenes; C021977:chrysene,2-diol-3,4-epoxide-1; D004851:Epoxide Hydrolases