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Mutagenicity of some monoaromatic hydroxamic acids.

C I Wei, M D Cohen, D D Swartz

    Toxicology Letters
    |January 1, 1985
    PubMed
    Summary

    Certain hydroxamic acids, particularly N-arylformohydroxamic acids, show mutagenicity in Salmonella typhimurium tester strains TA98 and TA100 after metabolic activation with rat liver S-9. N-acetyl-type hydroxamic acids were not mutagenic.

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    Area of Science:

    • Toxicology
    • Medicinal Chemistry
    • Genetics

    Background:

    • Hydroxamic acids are a class of organic compounds with diverse biological activities.
    • Assessing the mutagenicity of chemical compounds is crucial for understanding their potential health risks.
    • Metabolic activation by rat liver S-9 fraction is a standard method to evaluate pro-mutagens.

    Purpose of the Study:

    • To investigate the mutagenicity of various monoaromatic hydroxamic acids.
    • To determine the influence of structural modifications, specifically the aryl group and substitution pattern, on mutagenic potential.
    • To evaluate the role of metabolic activation in the mutagenicity of these compounds.

    Main Methods:

    • Bacterial reverse mutation assay using Salmonella typhimurium tester strains TA98 and TA100.

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  • Testing was conducted in the presence and absence of rat liver S-9 fraction for metabolic activation.
  • A series of N-(chlorophenyl)-substituted hydroxamic acids, N-arylformohydroxamic acids, and N-acetyl-type hydroxamic acids were synthesized and tested.

    • Main Results:

    • Four out of seven N-arylformohydroxamic acids tested were mutagenic to both Salmonella strains upon metabolic activation.
    • Two out of five N-(chlorophenyl)-substituted hydroxamic acids exhibited mutagenicity after metabolic activation.
    • None of the four N-acetyl-type hydroxamic acids showed mutagenic activity, even with metabolic activation.

    Conclusions:

    • The mutagenicity of monoaromatic hydroxamic acids is dependent on their chemical structure, particularly the presence of a formyl group on the N-aryl substituent.
    • N-arylformohydroxamic acids with specific aromatic nuclei are potential mutagens requiring metabolic activation.
    • N-acetyl-type hydroxamic acids appear to be non-mutagenic under the tested conditions, suggesting a protective effect of the acetyl group.