Cigarette smoke-induced DNA-damage: role of hydroquinone and catechol in the formation of the oxidative DNA-adduct, 8-hydroxydeoxyguanosine

Chem Biol Interact. 1990;75(1):71-81. doi: 10.1016/0009-2797(90)90023-g.

Abstract

This study demonstrates the ability of cigarette smoke condensate to generate hydrogen peroxide and to hydroxylate deoxyguanosine (dG) residues in isolated DNA to 8-hydroxydeoxyguanosine (8-OHdG). Both the formation of hydrogen peroxide and that of 8-OHdG in DNA was significantly decreased when catalase or tyrosinase was added to the smoke condensates, and this also occurred when pure hydroquinone or catechol, two major constitutes in cigarette smoke, was used instead of smoke condensate. Moreover, pure hydroquinone and catechol both caused dose-dependent formation of hydrogen peroxide and 8-OHdG, and there was good correlation between the amounts of hydrogen peroxide and 8-OHdG formed. These findings suggest that (i) hydroquinone and catechol may be responsible for the ability of cigarette smoke to cause 8-OHdG formation in DNA, (ii) this oxidative DNA-damage is due to the action of hydroxyl radicals formed during dissociation of hydrogen peroxide and (iii) the hydrogen peroxide in cigarette smoke is generated via autooxidation of hydroquinone and catechol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 8-Hydroxy-2'-Deoxyguanosine
  • Animals
  • Catalase / metabolism
  • Catechols / metabolism
  • Catechols / toxicity*
  • Cattle
  • DNA / drug effects
  • DNA Damage*
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / metabolism
  • Hydrogen Peroxide / metabolism
  • Hydroquinones / metabolism
  • Hydroquinones / toxicity*
  • Hydroxylation
  • Monophenol Monooxygenase / metabolism
  • Oxidation-Reduction
  • Plants, Toxic*
  • Smoke / adverse effects*
  • Smoke / analysis
  • Tobacco*

Substances

  • Catechols
  • Hydroquinones
  • Smoke
  • 8-Hydroxy-2'-Deoxyguanosine
  • DNA
  • Hydrogen Peroxide
  • Catalase
  • Monophenol Monooxygenase
  • Deoxyguanosine