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

Free Radical Biology and Medicine

Volumn 36, Issue 9, 2004, Pages 1087-1093

  Suzuki, Toshinori ^b   Nakano, Toshiki ^c   Masuda, Mitsuharu ^d   Ohshima, Hiroshi ^a  

^a INTERNATIONAL AGENCY FOR RESEARCH ON CANCER   (France)

^b SHUJITSU UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

^d KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

Author keywords

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

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; ASCORBIC ACID; COPPER CHLORIDE; DNA; EPIGALLOCATECHIN GALLATE; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; NUCLEOSIDE DERIVATIVE; POLYDEOXYRIBONUCLEOTIDE SYNTHASE; POLYPHENOL; REACTIVE OXYGEN METABOLITE; SPIROIMINODIHYDANTOIN NUCLEOSIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA SYNTHESIS; INCUBATION TIME; MUTATION; MUTATION RATE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; THYMUS;

CATECHIN; DEOXYGUANOSINE; DNA; FREE RADICAL SCAVENGERS; FREE RADICALS; HYPOCHLOROUS ACID; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEROXIDES;

EID: 1842634540     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.02.004     Document Type: Article

References (43)

1. Kettle A.J., Winterbourn C.C. Myeloperoxidase: a key regulator of neutrophil oxidant production. Redox Rep. 3:1997;3-15.
2. Foote C.S., Goyne T.E., Lehrer R.I. Assessment of chlorination by human neutrophils. Nature. 301:1983;715-716.
3. IARC Working Group Hypochlorite salts. Chlorinated drinking water; chlorination by-products; some other halogenated compounds; cobalt and cobalt compounds. 1991;159-176 IARC Press, Lyon.
4. Schmittinger P. Schmittinger P. Chlorine - principles and industrial practice. 2000;159-222 Wiley-VCH, Weinheim.
5. Wlodkowski T.J., Rosenkranz H.S. Mutagenicity of sodium hypochlorite for Salmonella typhimurium. Mutat. Res. 31:1975;39-42.
6. Hayatsu H., Hoshino H., Kawazoe Y. Potential cocarcinogenicity of sodium hypochlorite. Nature. 233:1971;495.
7. Patton W., Bacon V., Duffield A.M., Halpern B., Hoyano Y., Pereira W., Lederberg J. Chlorination studies: I. The reaction of aqueous hypochlorous acid with cytosine. Biochem. Biophys. Res. Commun. 48:1972;880-884.
8. Hayatsu H., Pan S., Ukita T. Reaction of sodium hypochlorite with nucleic acids and their constituents. Chem. Pharm. Bull. (Tokyo). 19:1971;2189-2192.
9. Whiteman M., Jenner A., Halliwell B. Hypochlorous acid-induced base modifications in isolated calf thymus DNA. Chem. Res. Toxicol. 10:1997;1240-1246.
10. Hoyano Y., Bacon V., Summons R.E., Pereira W.E., Halpern B., Duffield A.M. Chlorination studies: IV. The reaction of aqueous hypochlorous acid with pyrimidine and purine bases. Biochem. Biophys. Res. Commun. 53:1973;1195-1199.
11. Bernofsky C., Bandara B.M., Hinojosa O., Strauss S.L. Hypochlorite-modified adenine nucleotides: structure, spin-trapping, and formation by activated guinea pig polymorphonuclear leukocytes. Free Radic. Res. Commun. 9:1990;303-315.
12. Whiteman M., Jenner A., Halliwell B. 8-Chloroadenine: a novel product formed from hypochlorous acid-induced damage to calf thymus DNA. Biomarkers. 4:1999;303-310.
13. Masuda M., Suzuki T., Friesen M.D., Ravanat J.L., Cadet J., Pignatelli B., Nishino H., Ohshima H. Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils: Catalysis by nicotine and trimethylamine. J. Biol. Chem. 276:2001;40486-40496.
14. - system: identification of diimino-imidazole and amino-imidazolone nucleosides. Nucleic Acids Res. 30:2002;2555-2564.
15. - system. Chem. Res. Toxicol. 16:2003;382-389.
16. - system. Chem. Res. Toxicol. 14:2001;1163-1169.
17. Suzuki T., Ohshima H. Nicotine-modulated formation of spiroiminodihydantoin nucleoside via 8-oxo-7,8-dihydro-2′-deoxyguanosine in 2′-deoxyguanosine-hypochlorous acid reaction. FEBS Lett. 516:2002;67-70.
18. Guo Q., Zhao B., Shen S., Hou J., Hu J., Xin W. ESR study on the structure-antioxidant activity relationship of tea catechins and their epimers. Biochim. Biophys. Acta. 1427:1999;13-23.
19. ·OH radical-induced strand breaks and base damage through fast chemical repair of DNA radicals. Carcinogenesis. 22:2001;1189-1193.
20. Sakagami H., Sakagami T., Yoshida H., Omata T., Shiota F., Takahashi H., Kawazoe Y., Takeda M. Hypochlorite scavenging activity of polyphenols. Anticancer Res. 15:1995;917-921.
21. Fujiki H., Suganuma M., Imai K., Nakachi K. Green tea: cancer preventive beverage and/or drug. Cancer Lett. 188:2002;9-13.
22. Hazen S.L., Hsu F.F., Gaut J.P., Crowley J.R., Heinecke J.W. Modification of proteins and lipids by myeloperoxidase. Methods Enzymol. 300:1999;88-105.
23. Whiteman M., Hong H.S., Jenner A., Halliwell B. Loss of oxidized and chlorinated bases in DNA treated with reactive oxygen species: implications for assessment of oxidative damage in vivo. Biochem. Biophys. Res. Commun. 296:2002;883-889.
24. Shigenaga M.K., Aboujaoude E.N., Chen Q., Ames B.N. Assays of oxidative DNA damage biomarkers 8-oxo-2′-deoxyguanosine and 8-oxoguanine in nuclear DNA and biological fluids by high-performance liquid chromatography with electrochemical detection. Methods Enzymol. 234:1994;16-33.
25. Masuda M., Nishino H., Ohshima H. Formation of 8-nitroguanosine in cellular RNA as a biomarker of exposure to reactive nitrogen species. Chem. Biol. Interact. 139:2002;187-197.
26. Uppu R.M., Cueto R., Squadrito G.L., Salgo M.G., Pryor W.A. Competitive reactions of peroxynitrite with 2′-deoxyguanosine and 7,8-dihydro-8-oxo- 2′-deoxyguanosine (8-oxodG): relevance to the formation of 8-oxodG in DNA exposed to peroxynitrite. Free Radic. Biol. Med. 21:1996;407-411.
27. Kasai H. Chemistry-based studies on oxidative DNA damage: formation, repair, and mutagenesis. Free Radic. Biol. Med. 33:2002;450-456.
28. Helbock H.J., Beckman K.B., Shigenaga M.K., Walter P.B., Woodall A.A., Yeo H.C., Ames B.N. DNA oxidation matters: the HPLC-electrochemical detection assay of 8-oxo-deoxyguanosine and 8-oxo-guanine. Proc. Natl Acad. Sci. USA. 95:1998;288-293.
29. Yanagawa H., Ogawa Y., Ueno M. Redox ribonucleosides: isolation and characterization of 5-hydroxyuridine, 8-hydroxyguanosine, and 8-hydroxyadenosine from Torula yeast RNA. J. Biol. Chem. 267:1992;13320-13326.
30. Niles J.C., Burney S., Singh S.P., Wishnok J.S., Tannenbaum S.R. Peroxynitrite reaction products of 3′,5′-di-O-acetyl-8-oxo-7, 8-dihydro-2′-deoxyguanosine. Proc. Natl Acad. Sci. USA. 96:1999;11729-11734.
31. Sheu C.M., Foote C.S. Solvent and electronic effects on the reaction of guanosine derivatives with singlet oxygen. J. Org. Chem. 60:1995;4498-4503.
32. Buchko G.W., Wagner J.R., Cadet J., Raoul S., Weinfeld M. Methylene blue-mediated photooxidation of 7,8-dihydro-8-oxo-2′-deoxyguanosine. Biochim. Biophys. Acta. 1263:1995;17-24.
33. Hickerson R.P., Prat F., Muller J.G., Foote C.S., Burrows C.J. Sequence and stacking of 8-oxoguanine oxidation: comparison of one-electron vs singlet oxygen mechanism. J. Am. Chem. Soc. 121:1999;9423-9428.
34. Ravanat J.L., Saint-Pierre C., Cadet J. One-electron oxidation of the guanine moiety of 2′-deoxyguanosine: influence of 8-oxo-7,8-dihydro- 2′-deoxyguanosine. J. Am. Chem. Soc. 125:2003;2030-2031.
35. Burrows C.J., Muller J.G., Kornyushyna O., Luo W., Duarte V., Leipold M.D., David S.S. Structure and potential mutagenicity of new hydantoin products from guanosine and 8-oxo-7,8-dihydroguanine oxidation by transition metals. Environ. Health Perspect. 110:2002;713-717.
36. Henderson P.T., Delaney J.C., Gu F., Tannenbaum S.R., Essigmann J.M. Oxidation of 7,8-dihydro-8-oxoguanine affords lesions that are potent sources of replication errors in vivo. Biochemistry. 41:2002;914-921.
37. Kornyushyna O., Berges A.M., Muller J.G., Burrows C.J. In vitro nucleotide misinsertion opposite the oxidized guanosine lesions spiroiminodihydantoin and guanidinohydantoin and DNA synthesis past the lesions using Escherichia coli DNA polymerase I (Klenow fragment). Biochemistry. 41:2002;15304-15314.
38. Duarte V., Muller J.G., Burrows C.J. Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Res. 27:1999;496-502.
39. Nishimura S. Involvement of mammalian OGG1(MMH) in excision of the 8-hydroxyguanine residue in DNA. Free Radic. Biol. Med. 32:2002;813-821.
40. Le Page F., Kwoh E.E., Avrutskaya A., Gentil A., Leadon S.A., Sarasin A., Cooper P.K. Transcription-coupled repair of 8-oxoguanine: requirement for XPG, TFIIH, and CSB and implications for Cockayne syndrome. Cell. 101:2000;159-171.
41. Hazra T.K., Muller J.G., Manuel R.C., Burrows C.J., Lloyd R.S., Mitra S. Repair of hydantoins, one electron oxidation product of 8-oxoguanine, by DNA glycosylases of Escherichia coli. Nucleic Acids Res. 29:2001;1967-1974.
42. Leipold M.D., Muller J.G., Burrows C.J., David S.S. Removal of hydantoin products of 8-oxoguanine oxidation by the Escherichia coli DNA repair enzyme FPG. Biochemistry. 39:2000;14984-14992.
43. Duarte V., Gasparutto D., Jaquinod M., Ravanat J., Cadet J. Repair and mutagenic potential of oxaluric acid, a major product of singlet oxygen-mediated oxidation of 8-oxo-7,8-dihydroguanine. Chem. Res. Toxicol. 14:2001;46-53.