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Interaction of halocompounds with nucleic acids.

G Prodi, G Arfellini, A Colacci

    Toxicologic Pathology
    |January 1, 1986
    PubMed
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    This study investigated chemical binding to DNA and proteins in mice. Brominated compounds showed higher activation than chlorinated ones, with reactivity correlating to genotoxicity and carcinogenicity.

    Area of Science:

    • Toxicology
    • Molecular Biology
    • Biochemistry

    Background:

    • Chemicals like epichlorohydrin, haloalkanes, and aryl halides can interact with biological macromolecules.
    • Understanding their binding and activation is crucial for assessing health risks.

    Purpose of the Study:

    • To investigate the in vivo and in vitro binding of specific chemicals to nucleic acids and proteins.
    • To compare the enzymatic activation pathways and relative reactivity of these compounds.
    • To correlate binding data with genotoxicity and oncogenicity.

    Main Methods:

    • Studied chemical binding in murine organs using in vivo and in vitro systems.
    • Assessed enzymatic activation via microsomal P-450-dependent mixed function oxidase and cytosolic GSH-transferases.

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  • Quantified relative reactivity using the Covalent Binding Index (CBI) to rat liver DNA.

    • Main Results:

    • In vivo enzymatic activation was higher for brominated compounds than chlorinated ones.
    • Aryl halides preferentially bound to liver DNA; alkyl halides showed similar binding in liver, kidney, and lung.
    • Reactivity order (CBI) was: 1,2-dibromoethane > bromobenzene > 1,2-dichloroethane > chlorobenzene > epichlorohydrin > benzene.
    • In vitro activation involved P-450 and GSH-transferases, consistent with in vivo findings.

    Conclusions:

    • Binding patterns and enzymatic activation varied between alkyl and aryl halides.
    • CBI values correlated well with genotoxicity and oncogenicity data.
    • Chlorobenzene and bromobenzene demonstrated clear genotoxicity and potential carcinogenicity.