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  • Title: Mutagenicity and chemical reactivity of epoxidic intermediates of the isoprene metabolism and other structurally related compounds.
    Author: Gervasi PG, Citti L, Del Monte M, Longo V, Benetti D.
    Journal: Mutat Res; 1985; 156(1-2):77-82. PubMed ID: 3158813.
    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.
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