Conformations of adducts and kinetics of binding to DNA of the optically pure enantiomers of anti-benzo(a)pyrene diol epoxide

Nicholas E. Geacintov, Hiroko Yoshida, Victor Ibanez, Stephen A. Jacobs, Ronald G. Harvey

Research output: Contribution to journalArticle

Abstract

Kinetic flow dichroism studies indicate that the (+) enantiomer of 7β, 8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene physically bound at intercalative-type sites in double-stranded DNA undergoes covalent binding reactions to form adducts at external binding sites. The conformation of the non-covalent complex derived from the (-) stereoisomer is also intercalative in nature, but the conformations of the covalent adducts are heterogeneous and are characterized by both intercalative-type and external conformations. It is suggested that the distinctly higher biological activity of the (+) enantiomer relative to the activity of the (-) enantiomer may be related to the preponderance of 7,8,9-triol benzo(a)pyrene residues covalently linked to deoxyguanine and located at external binding sites in the DNA adducts.

Original languageEnglish (US)
Pages (from-to)33-39
Number of pages7
JournalBiochemical and Biophysical Research Communications
Volume122
Issue number1
DOIs
StatePublished - Jul 18 1984

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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