Kinetics of hydrolysis to tetraols and binding of benzo(a)pyrene-7,8-dihydrodiol-9,10-oxide and its tetraol derivatives to DNA. Conformation of adducts

Nicholas E. Geacintov, Victor Ibanez, Antoine G. Gagliano, Hiroko Yoshida, Ronald G. Harvey

Research output: Contribution to journalArticle

Abstract

When the major reactive metabolite of benzo(a)pyrene, trans -7,8-dihydroxy - anti-9,10-epoxy -7,8,9,10-tetrahydrobenzo(a)pyrene (anti-BPDE) is incubated with DNA in aqueous solution at 25°C, both covalent binding and hydrolysis of anti-BPDE to its tetraols occur. Using fluorescence and absorption spectroscopy it is shown that hydrolysis of anti-BPDE is markedly accelerated by DNA. In the presence of 5A260 units of DNA per ml in cacodylate buffer solution, at an initial concentration of DNA phosphate/anti-BPDE ratio of 100, both the extent of covalent binding to DNA ( < 7% of the total anti-BPDE initially present) and hydrolysis of anti-BPDE reach their maximum levels within less than five minutes after mixing. Absorption and electric linear dichroism spectra indicate that the tetraols bind non-covalently to DNA by an intercalation mechanism, whereas the covalent product displays the characteristics of an externally bound complex.

Original languageEnglish (US)
Pages (from-to)1335-1342
Number of pages8
JournalBiochemical and Biophysical Research Communications
Volume92
Issue number4
DOIs
StatePublished - Feb 27 1980

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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