Fluorescence line narrowing spectrometric analysis of benzo[a]pyrene-DNA adducts formed by one-electron oxidation

Chem Res Toxicol. 1989 Jan-Feb;2(1):29-34. doi: 10.1021/tx00007a005.

Abstract

Fluorescence line narrowing (FLN) was demonstrated for five benzo[a]pyrene (BP)-nucleoside adducts synthesized by one-electron oxidation of BP in the presence of guanosine, deoxyguanosine, and deoxyadenosine. The standard FLN spectra were used to prove that a major depurination adduct from the binding of BP to DNA in rat liver nuclei is 7-(benzo[a]pyren-6-yl)guanine (N7Gua). The structural characterization was performed with only 20 pg of the adduct. Metabolic activation of BP by one-electron oxidation in the horseradish peroxidase catalyzed reaction of BP with DNA (in vitro) was also investigated. The major adduct identified was 8-(benzo[a]pyren-6-yl)guanine (C8Gua).

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Benzo(a)pyrene / chemistry*
  • Benzo(a)pyrene / metabolism
  • Cell Nucleus / metabolism
  • Chromatography, High Pressure Liquid
  • DNA / chemistry*
  • DNA / metabolism
  • DNA Adducts*
  • Guanine / metabolism
  • Liver / metabolism
  • Liver / ultrastructure
  • Oxidation-Reduction
  • Rats
  • Spectrometry, Fluorescence / methods
  • Spectrum Analysis / methods

Substances

  • DNA Adducts
  • benzo(a)pyrene-DNA adduct
  • Benzo(a)pyrene
  • Guanine
  • DNA