Lack of contribution of covalent benzo[a]pyrene-7,8-quinone-DNA adducts in benzo[a]pyrene-induced mouse lung tumorigenesis

Chem Biol Interact. 2010 Jul 30;186(2):157-65. doi: 10.1016/j.cbi.2010.03.037. Epub 2010 Mar 25.

Abstract

Benzo[a]pyrene (B[a]P) is a potent human and rodent lung carcinogen. This activity has been ascribed in part to the formation of anti-trans-7,8-dihydroxy-7,8-dihydroB[a]P-9,10-epoxide (BPDE)-DNA adducts. Other carcinogenic mechanisms have been proposed: (1) the induction of apurinic sites from radical cation processes, and (2) the metabolic formation of B[a]P-7,8-quinone (BPQ) that can form covalent DNA adducts or reactive oxygen species which can damage DNA. The studies presented here sought to examine the role of stable BPQ-DNA adducts in B[a]P-induced mouse lung tumorigenesis. Male strain A/J mice were injected intraperitoneally once with BPQ or trans-7,8-dihydroxy-7,8-dihydroB[a]P (BP-7,8-diol) at 30, 10, 3, or 0mg/kg. Lungs and livers were harvested after 24h, the DNA extracted and subjected to (32)P-postlabeling analysis. Additional groups of mice were dosed once with BPQ or BP-7,8-diol each at 30 mg/kg and tissues harvested 48 and 72 h later, or with B[a]P (50mg/kg, a tumorigenic dose) and tissues harvested 72 h later. No BPQ or any other DNA adducts were observed in lung or liver tissues 24, 48, or 72 h after the treatment with 30 mg/kg BPQ. BP-7,8-diol gave BPDE-DNA adducts at all time points in both tissues and B[a]P treatment gave BPDE-DNA adducts in the lung. In each case, no BPQ-DNA adducts were detected. Mouse body weights significantly decreased over time after BPQ or BP-7,8-diol treatments suggesting that systemic toxicity was induced by both agents. Model studies with BPQ and N-acetylcysteine suggested that BPQ is rapidly inactivated by sulfhydryl-containing compounds and not available for DNA adduction. We conclude that under these treatment conditions BPQ does not form stable covalent DNA adducts in the lungs or livers of strain A/J mice, suggesting that stable BPQ-covalent adducts are not a part of the complex of mechanisms involved in B[a]P-induced mouse lung tumorigenesis.

MeSH terms

  • 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide / chemistry*
  • Acetylcysteine / pharmacology
  • Animals
  • Benzo(a)pyrene / chemistry
  • Benzo(a)pyrene / metabolism
  • Benzo(a)pyrene / toxicity*
  • Carcinogens / chemistry
  • Carcinogens / metabolism
  • Carcinogens / toxicity*
  • DNA Adducts / biosynthesis*
  • DNA Adducts / chemistry*
  • Free Radical Scavengers / pharmacology
  • Humans
  • Lung Neoplasms / chemically induced*
  • Lung Neoplasms / metabolism*
  • Male
  • Mice
  • Mice, Inbred A
  • Models, Biological
  • Phosphorus Radioisotopes
  • Polycyclic Aromatic Hydrocarbons / chemistry
  • Polycyclic Aromatic Hydrocarbons / metabolism
  • Polycyclic Aromatic Hydrocarbons / toxicity

Substances

  • Carcinogens
  • DNA Adducts
  • Free Radical Scavengers
  • Phosphorus Radioisotopes
  • Polycyclic Aromatic Hydrocarbons
  • benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide-DNA
  • Benzo(a)pyrene
  • 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
  • Acetylcysteine