The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA

Ercole L. Cavalieri, Eleanor G. Rogan, Robert W. Roth, Richard K. Saugier, Alaeddin Hakam

Research output: Contribution to journalArticle

85 Scopus citations

Abstract

The ionization potentials (IP) of 91 alternant polycyclic aromatic hydrocarbons (PAH) were determined from the absorption maximum of the chargetransfer complex of each hydrocarbon and chloranil in chloroform. The extent of horseradish peroxidase (HRP)-catalyzed binding to DNA of 14 hydrocarbons of varying IP was measured. Only hydrocarbons with IP < approx. 7.35eV were significantly bound to DNA. These results provide further evidence that HRP-mediated binding of PAH to DNA occurs by one-electron oxidation and indicate that hydrocarbons must have IP < approx. 7.35eV to be activated by one-electron oxidation. Thus, determination of IP and HRP-catalyzed binding to DNA can offer some guidelines for selecting aromatic hydrocarbons which might undergo carcinogenic activation by this mechanism.

Original languageEnglish (US)
Pages (from-to)87-109
Number of pages23
JournalChemico-Biological Interactions
Volume47
Issue number1
DOIs
StatePublished - Oct 15 1983

Keywords

  • Carcinogenic activation
  • DNA binding
  • Horseradish peroxidase
  • Ionization potential
  • One-electron oxidation
  • Polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

  • Toxicology

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