Comparative laser spectroscope study of DNA and polynucleotide adducts from the (+)-anti-diol epoxide of benzo[a]pyrene

Peiqi Lu, Hyuk Jeong, Ryszard Jankowiak, G. J. Small, S. K. Kim, Monique Cosman, Nicholas Geacintov

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Abstract

A recently developed methodology [Jankowiak, R., Lu, P., Small, G. J., and Geacintov, N. E. (1990) Chem. Res. Toxicol. 3, 39-46], which combines fluorescence line narrowing spectroscopy at 4.2 K with non-line-narrowed (S2 ← S0 laser excitation) fluorescence spectroscopy at 77 K and fluorescence quenching, is used to characterize adducts formed from (+)-anti-BPDE and the alternating copolymers poly(dG-dC)·poly(dG-dC) and poly(dA-dT)·poly(dA-dT), the non-alternating poly(dG)·poly(dC), single-strand poly(dG), and the oligonucleotide d(ATATGTATA). Detailed comparisons of the fluorescence spectra and quenching (with acrylamide) of the properties of the adducts with those of (+)-anti-BPDE-DNA adducts are made. Fluorescence spectra of the trans and cis isomers of the adduct formed from guanosine monophosphate and the adducts of d(ATATGTATA) are used to assign the stereochemistry of the two major DNA adducts as irons-N2-dG moieties which occupy two different DNA sites. Evidence for the existence of minor cis-type guanine adducts is provided. Finally, a fourth type of DNA adduct (minor) is identified and assigned as trans-N6-dA.

Original languageEnglish (US)
Pages (from-to)58-69
Number of pages12
JournalChemical Research in Toxicology
Volume4
Issue number1
Publication statusPublished - 1991

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ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Toxicology
  • Health, Toxicology and Mutagenesis

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