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Published on: December 21, 2016

Mutagenicity of halogenated and oxygenated three-carbon compounds

S J Stolzenberg, C H Hine

    Journal of Toxicology and Environmental Health
    |November 1, 1979
    PubMed

    Insights

    Epoxide compounds like epichlorohydrin and epibromohydrin are potent mutagens, while DBCP requires metabolic activation. These three-carbon compounds primarily showed mutagenicity in base-pair substitution tests, not frameshift mutations.

    Area of Science:

    • Toxicology
    • Mutagenesis
    • Chemical Safety

    Background:

    • Three-carbon compounds with antifertility activity were investigated for mutagenic potential.
    • The study focused on structurally related compounds and their brominated derivatives.

    Purpose of the Study:

    • To assess the mutagenic activity of specific three-carbon compounds using the Salmonella typhimurium assay.
    • To determine the activation requirements and dose-response relationships for these compounds.

    Main Methods:

    • Utilized the Salmonella typhimurium mutagenicity test (Ames test) with strains TA-100 (base-pair substitution) and TA-98 (frameshift).
    • Tested compounds both with and without S9 microsomal preparation for metabolic activation.
    • Evaluated dose-related responses for mutagenic activity.

    Main Results:

    • Epichlorohydrin, epibromohydrin, and glycidol were direct, highly active mutagens without S9 activation.
    • 1,2-dibromo-3-chloropropane (DBCP) required S9 activation to exhibit mutagenicity.
    • Alpha-bromohydrin was significantly more mutagenic than alpha-chlorohydrin.
    • Compounds showed activity against base-pair substitution strains but were inactive against frameshift strains.
    • Glycerol, propylene glycol, and n-propanol were inactive.

    Conclusions:

    • Epoxide-containing three-carbon compounds are potent direct mutagens.
    • Metabolic activation is crucial for the mutagenicity of certain halogenated propanes like DBCP.
    • The mutagenic potential of these compounds is primarily associated with base-pair substitution mechanisms.

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