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Reactive intermediates from 3-hydroxybenzo[a]pyrene and its glucuronide.

O Ribeiro, C A Kirkby, P C Hirom

    Carcinogenesis
    |March 1, 1986
    PubMed
    Summary
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    Horseradish peroxidase oxidizes 3-hydroxybenzo[a]pyrene to a quinone. N-acetylcysteine and glutathione form adducts with this metabolite, indicating detoxification pathways for polycyclic aromatic hydrocarbons.

    Area of Science:

    • Environmental Chemistry
    • Biochemistry
    • Toxicology

    Background:

    • 3-Hydroxybenzo[a]pyrene (3-OH-BaP) is a metabolite of the polycyclic aromatic hydrocarbon benzo[a]pyrene.
    • Polycyclic aromatic hydrocarbons (PAHs) are environmental pollutants with known carcinogenic properties.
    • Understanding PAH metabolism is crucial for assessing their health risks.

    Purpose of the Study:

    • To investigate the metabolic fate of 3-hydroxybenzo[a]pyrene (3-OH-BaP) using the horseradish peroxidase/H2O2 system.
    • To identify and characterize the products formed from the reaction of 3-OH-BaP with nucleophiles like N-acetylcysteine and glutathione.
    • To explore potential detoxification pathways for 3-OH-BaP.

    Main Methods:

    • Enzymatic oxidation of 3-OH-BaP using horseradish peroxidase and hydrogen peroxide.

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  • Incubation of reaction products with N-acetylcysteine and glutathione.
  • Chemical and spectral analysis (UV, mass spectrometry, NMR) for product identification.
  • Enzymatic hydrolysis of benzo[a]pyrene-3-glucuronide followed by analysis.

    • Main Results:

    • 3-OH-BaP was oxidized to benzo[a]pyrene-3,6-quinone.
    • A novel adduct, 6-(N-acetyl-cystein-S-yl)-3-hydroxybenzo[a]pyrene (6-NAc-cys-3-OH-BaP), was formed in the presence of N-acetylcysteine.
    • Glutathione also formed an adduct with 3-OH-BaP.
    • Enzymic hydrolysis of benzo[a]pyrene-3-glucuronide yielded a product identical to 6-NAc-cys-3-OH-BaP.

    Conclusions:

    • The horseradish peroxidase system facilitates the oxidation of 3-OH-BaP to a reactive quinone.
    • N-acetylcysteine and glutathione can conjugate with 3-OH-BaP metabolites, suggesting these thiols play a role in detoxification.
    • The formation of the 6-NAc-cys-3-OH-BaP adduct is consistent with nucleophilic attack on the benzo[a]pyrene-3,6-quinone intermediate.