DNA damage by ethylbenzenehydroperoxide formed from carcinogenic ethylbenzene by sunlight irradiation

Biochem Biophys Res Commun. 2003 May 16;304(4):638-42. doi: 10.1016/s0006-291x(03)00652-1.

Abstract

Ethylbenzene, widely used in human life, is a non-mutagenic carcinogen. Sunlight-irradiated ethylbenzene caused DNA damage in the presence of Cu2+, but unirradiated ethylbenzene did not. A Cu+ -specific chelator bathocuproine inhibited DNA damage and catalase showed a little inhibitory effect. The scopoletin assay revealed that peroxides and H(2)O(2) were formed in ethylbenzene exposed to sunlight. These results suggest that Cu+ and alkoxyl radical mainly participate in DNA damage, and H(2)O(2) partially does. When catalase was added, DNA damage at thymine and cytosine was inhibited. Ethylbenzenehydroperoxide, identified by GC/MS analysis, induced the formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine and caused DNA damage at consecutive guanines, as observed with cumenehydroperoxide. Equimolar concentrations of H(2)O(2) and acetophenone were produced by the sunlight-irradiation of 1-phenylethanol, a further degraded product of ethylbenzene. These results indicate a novel pathway that oxidative DNA damage induced by the peroxide and H(2)O(2) derived from sunlight-irradiated ethylbenzene may lead to expression of the carcinogenicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzene Derivatives / metabolism*
  • Carcinogens / metabolism*
  • Copper / metabolism
  • DNA / metabolism
  • DNA / radiation effects
  • DNA Damage*
  • Genes, p53
  • Humans
  • Molecular Structure
  • Oxidation-Reduction
  • Peroxides / metabolism*
  • Sunlight*

Substances

  • Benzene Derivatives
  • Carcinogens
  • Peroxides
  • ethylbenzene hydroperoxide
  • Copper
  • DNA
  • ethylbenzene