Preparation of Oligoselenodiglutathiones and Their Suppressive Effects on Oxidative DNA Damage Induced by Catechol and Copper

Journal of Health Science

Volumn 57, Issue 1, 2011, Pages 72-77

  Ando, Motozumi ^a   Nishida, Hiroyuki ^a   Ueda, Koji ^a   Itoh, Kazuo ^a   Okamoto, Yoshinori ^a   Kojima, Nakao ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

Antiox idative; Glutathione; Oligoselenodiglutathione; Oxidative DNA damage; Selenium; Selenotrisulfide

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; CATECHOL; COPPER; DISELENODIGLUTATHIONE; GLUTATHIONE DERIVATIVE; GLUTATHIONE DISULFIDE; SELENITE; SELENIUM; SELENODIGLUTATHIONE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DNA DAMAGE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METAL METABOLISM; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PROTEIN FUNCTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 79952588078     PISSN: 13449702     EISSN: 13475207     Source Type: Journal    
DOI: 10.1248/jhs.57.72     Document Type: Article

References (26)

1. Rayman, M. P. (2000) The importance of selenium to human health. Lancet, 356, 233-241.
2. Rotruck, J. T., Pope, A. L., Ganther, H. E., Swanson, A. B., Hafeman, D. G., and Hoekstra, W. G., (1973) Selenium: biochemical role as a component of glutathione peroxidase. Science, 179, 588-590.
3. Barceloux, D. G. (1999) Selenium. J. Toxicol. Clin. Toxicol., 37, 145-172.
4. Ganther, H. E. (1999) Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase. Carcino genesis, 20, 1657-1666.
5. Turner, R. J., Weiner, J. H. and Taylor, D. E. (1998) Selenium metabolism in Escherichia coli. Biometals, 11, 223-227.
6. Park, Y. C., Kim, J. B., Heo, Y., Park, D. C., Lee, I. S., Chung, H. W., Han, J. H., Chung, W. G., Vendeland, S. C. and Whanger, P. D. (2004) Metabolism of subtoxic level of selenite by double perfused small intestine in rats. Biol. Trace Elem. Res., 98, 143-157.
7. Ganther, H. E. (1968) Selenotrisulfides. Formation by the reaction of thiols with selenious acid. Biochemistry, 7, 2898-2905.
8. Painter, E. P. (1941) The chemistry and toxicity of selenium compounds, with special reference to the selenium problem. Chem. Rev., 28, 179-213.
9. Gammelgaard, B., Gabel-Jensen, C., Stürup, S. and Hansen, H. R. (2008) Complementary use of molecular and element-specific mass spectrometry for identification of selenium compounds related to human selenium metabolism. Anal. Bioanal. Chem., 390,1691-1706.
10. Stadtman, T. C. (1996) Selenocysteine. Annu. Rev. Biochem., 65, 83-100.
11. Kryukov, G. V., Castellano, S., Novoselov, S. V., Lobanov, A. V., Zehtab, O., Guigó, R. and Gladyshev, V. N. (2003) Characterization of mam- malian selenoproteomes. Science, 300, 1439-1443.
12. Lindemann, T. and Hintelmann, H. (2002) Identification of selenium-containing glutathione S- conjugates in a yeast extract by two-dimensional liquid chromatography with inductively coupled plasma MS and nanoelectrospray MS/MS detection. Anal. Chem., 74, 4602-4610.
13. Nishida, Y.,Ando, M., Ioth, K.,Ueda, K.,Nishida, Y. Okamoto, Y., Toda, C. and Kojima, N. (2010) Production of polyselenodipenicillamines, unique selenium compounds. Chem. Pharm. Bull. (Tokyo), 58,957-960.
14. Ando, M., Nishida, H., Itoh, K., Okamoto, Y., Ueda, K. and Kojima, N. (2010) Penicillamine selenotrisulfide suppressed DNA strand breaks and oxidative DNA damage in vitro. Journal of Research Institute of Meijo University, 9, 27-33.
15. Gabel-Jensen, C., Gammelgaard, B., Bendahl, L., Stürup, S. and Jøns, O. (2006) Separation and identification of selenotrisulfides in epithelial cell homogenates by LC-ICP-MS and LC-ESI-MS after incubation with selenite. Anal. Bioanal. Chem., 384, 697-702.
16. Hsieh, H. S. and Ganther, H. E. (1975) Acid-volatile selenium formation catalyzed by glutathione reductase. Biochemistry, 14, 1632-1636.
17. Pederson, J. Z., Steinkühler, C., Weser, U. and Rotilio, G. (1996) Copper-glutathione complexes under physiological conditions: structures in solution different from the solid state coordination. Biometals, 9, 3-9.
18. Hirakawa, K., Oikawa, S., Hiraku, Y., Hirosawa, I. and Kawanishi, S. (2002) Catechol and hydroquinone have different redox properties responsible for their differential DNA-damaging ability. Chem. Res. Toxicol., 15, 76-82.
19. Saito, Y., Baba, Y., Sato, T. and Chikuma, M. (2008) DNA damages induced by selenite in the presence of glutathione. Reactive oxygen species involved in DNA damages. Biomed. Res. Trace Elem., 19, 317-320.
20. Jain, A., Alvi, N. K., Parish, J. H. and Hadi, S. M. (1996) Oxygen is not required for degradation of DNA by glutathione and Cu(II). Mutat. Res., 357, 83-88.
21. Steinkühler, C., Pedersen, J. Z., Weser, U. and Rotilio, G. (1991) Oxidative stress induced by a dischiff base copper complex is both mediated and modulated by glutathione. Biochem. Pharmacol., 42,1821-1827.
22. Rafferty T. S., Green, M. H. L., Lowe, J. E., Arlett, C., Hunter, J. A. A., Beckett, G. J. and McKenzie, R. C. (2003) Effects of selenium compounds on induction of DNA damage by broadband ultraviolet radiation in human keratinocytes. Br. J. Dermatol., 148,1001-1009.
23. Stewart, M. S., Cameron, G. S. and Pence, B. C. (1996) Antioxidant nutrients protect against UVB- induced oxidative damage to DNA of mouse keratinocytes in culture. J. Invest. Dermatol., 106, 1086-1089.
24. Newairy, A. A., El-Sharaky, A. S., Badreldeen, M. M., Eweda, S. M. and Sheweita, S. A. (2007) The hepatoprotective effects of selenium against cadmium toxicity in rats. Toxicology, 242, 23-30.
25. Fairweather-Tait, S. J., Collings, R. and Hurst, R. (2010) Selenium bioavailability: current knowledge and future research requirements. Am. J. Clin. Nutr., 91,1484-1491.
26. Vendeland, S. C., Deagen, J. T. and Whanger, P. D. (1992) Uptake of selenotrisulfides of glutathione and cysteine by brush border membranes from rat intestines. J. Inorg. Biochem., 47, 131-140.