Mutagenicity of chloroalkene epoxides in bacterial systems.
6 alpha-chloroepoxides have been tested for in vitro activity in a variety of systems. The epoxides were cis- and trans-1-chloropropene oxide, cis- and trans-1,3-dichloropropene oxide, trichloroethylene oxide and tetrachloroethylene oxide. The epoxides were assayed for mutagenicity in the absence of metabolic activation in S. typhimurium TA1535 and E. coli WP2 uvrA and for preferential inhibition of growth of DNA-repair-deficient E. coli. All 6 epoxides possessed DNA-modifying activity as evidenced by their ability to preferentially inhibit DNA polymerase-deficient E. coli. All of the test chemicals except trichloroethylene oxide were mutagenic for S. typhimurium and all except trichloroethylene oxide and tetrachloroethylene oxide were mutagenic for E. coli Wp2 uvrA. Cis- and trans-1,3-dichloropropene oxide were the most potent mutagens and DNA modifiers. For all cases, the cis isomers were more active than the corresponding trans isomers. alpha-Chloroepoxides are considered likely to be the active intermediates of the carcinogenic parent halo-olefins. These mutagenicity studies are considered relevant in assessing the carcinogenicity of the parent hydrocarbons.
D004256:DNA Polymerase I / Q000172:deficiency; D004260:DNA Repair / Q000187:drug effects; D004269:DNA, Bacterial / Q000235:genetics; D004852:Epoxy Compounds / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects* / Q000235:genetics; D004988:Ethers, Cyclic / Q000494:pharmacology*; D006843:Hydrocarbons, Chlorinated / Q000494:pharmacology*; D009152:Mutagenicity Tests; D009153:Mutagens; D012486:Salmonella typhimurium / Q000187:drug effects*
D004269:DNA, Bacterial; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D006843:Hydrocarbons, Chlorinated; D009153:Mutagens; D004256:DNA Polymerase I