title: Mutagenicity and chemical reactivity of epoxidic intermediates of the isoprene metabolism and other structurally related compounds.
abstract: The mutagenic activities of the epoxidic intermediates of the isoprene biotransformation were investigated using Salmonella typhimurium and compared with those of other structurally related epoxides. The compound 2-methyl-1,2,3,4-diepoxybutane, chemically analogous to the well known carcinogenic 1,2,3,4-diepoxybutane, was found to be as mutagenic as the latter. Moreover, the mutagenic activities of oxiranes were correlated to their alkylating powers towards nicotinamide and to their half-lives for spontaneous hydrolysis. The relationship between alkylating power and mutagenicity was found to hold for the stable epoxides that react mainly by an SN2 substitution mechanism.
authors.forename: P G
authors.initials: PG
authors.lastname: Gervasi
authors.forename: L
authors.initials: L
authors.lastname: Citti
authors.forename: M
authors.initials: M
authors.lastname: Del Monte
authors.forename: V
authors.initials: V
authors.lastname: Longo
authors.forename: D
authors.initials: D
authors.lastname: Benetti
mesh_terms: D001711:Biotransformation; D002070:Butadienes / Q000378:metabolism / Q000633:toxicity*; D004852:Epoxy Compounds / Q000378:metabolism / Q000633:toxicity*; D004988:Ethers, Cyclic / Q000633:toxicity*; D045782:Hemiterpenes; D007700:Kinetics; D009154:Mutation / Q000187:drug effects*; D009536:Niacinamide / Q000378:metabolism; D010420:Pentanes; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D002070:Butadienes; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D045782:Hemiterpenes; D010420:Pentanes; C005059:isoprene; D009536:Niacinamide