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Nitroso transfer from alpha-nitrosamino aldehydes: implications for carcinogenesis.

R N Loeppky, W Tomasik, B E Kerrick

    Carcinogenesis
    |July 1, 1987
    PubMed
    Summary

    Biochemical oxidation of beta-oxidized nitrosamines yields reactive aldehydes. These aldehydes readily transfer their nitroso group to amines, potentially activating nitrosamines as carcinogens.

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    Area of Science:

    • Biochemistry
    • Organic Chemistry
    • Toxicology

    Background:

    • Certain beta-oxidized nitrosamines are potent carcinogens.
    • Liver alcohol dehydrogenase catalyzes the oxidation of alkylnitrosamino ethanols.

    Purpose of the Study:

    • To synthesize and characterize alpha-nitrosamino aldehydes derived from alkylnitrosamino ethanols.
    • To investigate the transnitrosation properties of these aldehydes.
    • To explore the role of these reactions in nitrosamine carcinogenicity.

    Main Methods:

    • Synthesis of five representative nitrosamino-ethanals.
    • Study of transnitrosation reactions with various secondary and primary amines.
    • Analysis of reaction kinetics and products in organic solvents and aqueous buffers at different pH levels.

    Main Results:

    • Synthesized nitrosamino-ethanals undergo facile transnitrosation with secondary amines.
    • Transnitrosation rates are pH-dependent in aqueous media.
    • Transnitrosation to primary amines results in deamination.
    • Formation of glyoxal imines and other byproducts observed.

    Conclusions:

    • Beta-oxidized nitrosamines can be activated to proximate or ultimate carcinogens via biochemical oxidation.
    • The resulting alpha-nitrosamino aldehydes are reactive intermediates capable of transnitrosation.
    • These findings support a mechanism for nitrosamine-induced carcinogenesis.

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