Alkylating properties and genetic activity of 4-vinylcyclohexene metabolites and structurally related epoxides.
The mutagenicity of the epoxides 4-vinyl-1,2-epoxycyclohexane, 4-epoxyethyl-1,2-epoxycyclohexane, 4-epoxyethyl-1,2-dihydroxycyclohexane, 1,2-epoxycyclohexane and styrene oxide was assayed on the TA100 strain of S. typhimurium and V79 Chinese hamster cells. In the latter cell system, both point mutation (6-thioguanine resistance) and chromosomal damage (anaphase bridges and micronuclei) were scored. Genetic effects were related to the alkylating properties of the epoxides. For this purpose, alkylation of 4-(p-nitrobenzyl)pyridine (NBP) and sodium-p-nitrothiophenolate (NTP) was measured and values for the substrate constant (s) were calculated. 4-Epoxyethyl-1,2-epoxycyclohexane, 1,2-epoxycyclohexane and styrene oxide, characterized by the highest reactivity toward NBP and by an s value in the vicinity of 1, were mutagenic in all test systems. 4-Vinyl-1,2-epoxycyclohexane and 4-epoxyethyl-1,2-dihydroxycyclohexane, characterized by lower NBP reactivity and higher s value (1.30-1.38), did not induce reversion in S. typhimurium or 6-thioguanine-resistant mutants in V79 cells, but were as effective as the 3 other compounds in the induction of chromosomal damage.
D000818:Animals; D002460:Cell Line; D006224:Cricetinae; D003412:Cricetulus; D003510:Cyclohexanes / Q000494:pharmacology*; D053138:Cyclohexenes; D004852:Epoxy Compounds / Q000494:pharmacology; D008168:Lung; D009152:Mutagenicity Tests; D009153:Mutagens; D012486:Salmonella typhimurium / Q000235:genetics
D003510:Cyclohexanes; D053138:Cyclohexenes; D004852:Epoxy Compounds; D009153:Mutagens; C013733:4-vinylcyclohexene