Epigallocatechin gallate markedly enhances formation of 8-oxo-7,8-dihydro-2′-deoxyguanosine in the reaction of 2′-deoxyguanosine with hypochlorous acid

Toshinori Suzuki, Toshiki Nakano, Mitsuharu Masuda, Hiroshi Ohshima

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

A tea polyphenol, (-)-epigallocatechin gallate (EGCG), which can scavenge a variety of reactive oxygen species, enhances the yield of 8-oxo-7,8-dihydro- 2′-deoxyguanosine (8-oxo-dG) up to 20-fold in the reaction of 2′-deoxyguanosine with hypochlorous acid (HOCl), compared with the reaction without EGCG. Certain concentrations of EGCG inhibited HOCl-mediated oxidation of 2′-deoxyguanosine to 8-oxo-dG to a limited extent, but efficiently inhibited further oxidation of 8-oxo-dG to spiroiminodihydantoin nucleoside, resulting in the accumulation of 8-oxo-dG in the reaction mixture. Conversely, EGCG inhibited dose-dependently an increase in 8-oxo-dG levels in calf thymus DNA incubated with HOCl. However, addition of HOCl to the DNA preoxidized with an oxidant-generating system (CuCl2, ascorbate, H2O2), led to the extensive loss of 8-oxo-dG due to its further oxidation. EGCG effectively inhibited this HOCl-mediated loss of 8-oxo-dG in the oxidized DNA, resulting in an apparent increase in 8-oxo-dG levels in the oxidized DNA, compared with the levels found without EGCG. The conversion of 8-oxo-dG into other oxidized lesions will inevitably affect recognition by DNA repair enzymes as well as the rates of mutations and DNA synthesis. Thus, our results suggest that as a biomarker of oxidative DNA damage, not only 8-oxo-dG but also the products of its further oxidation should be analyzed.

Original languageEnglish
Pages (from-to)1087-1093
Number of pages7
JournalFree Radical Biology and Medicine
Volume36
Issue number9
DOIs
Publication statusPublished - 2004 May 1

Keywords

  • (-)-epigallocatechin gallate
  • 2′-Deoxyguanosine
  • 2′-deoxyguanosine
  • 8-Oxo-7,8-dihydro-2′-deoxyguanosine
  • 8-oxo-dG
  • EGCG
  • Epigallocatechin gallate
  • Free radicals
  • Hypochlorous acid
  • Spiroiminodihydantoin
  • Spiroiminodihydantoin nucleoside
  • dG
  • dS

ASJC Scopus subject areas

  • Biochemistry
  • Physiology (medical)

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