Skip to main content
Download PDF
  • Published:

The protective effects of selenoorganic compounds against peroxynitrite-induced changes in plasma proteins and lipids

Cellular & Molecular Biology Letters volume 11, pages 1–11 (2006)Cite this article

Abstract

Many selenoorganic compounds play an important role in biochemical processes and act as antioxidants, enzyme inhibitors or drugs. The effects of a new selenocompound — bis(2-aminophenyl)-diselenide on oxidative/nitrative changes in human plasma proteins induced by peroxynitrite (ONOO−) were studied in vitro and compared with the those of ebselen, a well-known antioxidant. We also studied the role of the tested selenocompounds in peroxynitrite-induced plasma lipid peroxidation. Exposure of the plasma to peroxynitrite (0.1 mM) resulted in an increase in the level of carbonyl groups and nitrotyrosine residues in plasma proteins (estimated using the ELISA method and Western blot analysis). In the presence of different concentrations (0.025–0.1 mM) of the tested selenocompounds, 0.1 mM peroxynitrite caused a distinct decrease in the level of carbonyl group formation and tyrosine nitration in plasma proteins. Moreover, these selenocompounds also inhibited plasma lipid peroxidation induced by ONOO−1 (0.1 mM). The obtained results indicate that in vitro bis(2-aminophenyl)-diselenide and ebselen have very similar protective effects against peroxynitrite-induced oxidative/nitrative damage to human plasma proteins and lipids.

Abbreviations

DMSO:

dimethylsufoxide

DNPH:

dinitrophenylhydrazine

ONOO− :

peroxynitrite

TBARS:

thiobarbituric acid reactive substance

References

  1. Soriano-Garcia, M. Organoselenium compounds as potential therapeutic and chemopreventive agents: a review. Curr. Med.Chem. 11 (2004) 1657–1669.

    PubMed  CAS  Google Scholar 

  2. Gromer, S., Johansson, L., Bauer, H., Arscott, L.D., Rauch, S., Ballou, D.P., Williams, C.H., Jr., Schirmer, R.H. and Arner, E.S. Active sites of thioredoxin reductases: why selenoproteins? Proc. Natl. Acad. Sci. USA 100 (2003) 12618–12623.

    Article  PubMed  CAS  Google Scholar 

  3. Rotruck, J.T., Pope, A.L., Ganther, H.E., Swanson, A.B., Hafeman, D.G. and Hoekstra, W.G. Selenium: biochemical role as a component of glutathione peroxidase. Science 179 (1973) 588–590.

    PubMed  CAS  Google Scholar 

  4. Low, S.C. and Berry, M.J. Knowing when not to stop: selenocysteine incorporation in eukaryotes. Trends Biochem. Sci. 21 (1996) 203–208.

    Article  PubMed  CAS  Google Scholar 

  5. Schewe, T. Molecular actions of ebselen — an antiinflammatory antioxidant. Gen. Pharmacol. 26 (1995) 1153–1169.

    PubMed  CAS  Google Scholar 

  6. Furstenau, C.R., Spier, A.P., Rucker, B., Luisa, B.S., Battastini, A.M. and Sarkis, J.J. The effect of ebselen on adenine nucleotide hydrolysis by platelets from adult rats. Chem. Biol Interact. 148 (2004) 93–99.

    Article  PubMed  Google Scholar 

  7. Lindenblatt, N., Schareck, W., Belusa, L., Nickels, R.M., Menger, M.D. and Vollmar, B. Anti-oxidant ebselen delays microvascular thrombus formation in the rat cremaster muscle by inhibiting platelet P-selectin expression. Thromb. Haemost. 90 (2003) 882–892.

    PubMed  CAS  Google Scholar 

  8. Sies, H. Ebselen, a selenoorganic compound as glutathione peroxidase mimic. Free Radic. Biol Med. 14 (1993) 313–323.

    Article  PubMed  CAS  Google Scholar 

  9. Briviba, K., Roussyn, I., Sharov, V.S. and Sies, H. Attenuation of oxidation and nitration reactions of peroxynitrite by selenomethionine, selenocystine and ebselen. Biochem. J. 319 (1996) 13–15.

    PubMed  CAS  Google Scholar 

  10. Beckman, J.S., Beckman, T.W., Chen, J., Marshall, P.A. and Freeman, B.A. Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. USA 87 (1990) 1620–1624.

    Article  PubMed  CAS  Google Scholar 

  11. Pryor, W.A. and Squadrito, G.L. The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 268 (1995) L699–L722.

    PubMed  CAS  Google Scholar 

  12. Arteel, G.E., Briviba, K. and Sies, H. Protection against peroxynitrite. FEBS Lett. 445 (1999) 226–230.

    Article  PubMed  CAS  Google Scholar 

  13. Groves, J.T. Peroxynitrite: reactive, invasive and enigmatic. Curr. Opin. Chem. Biol. 3 (1999) 226–235.

    Article  PubMed  CAS  Google Scholar 

  14. Hogg, N., Darley-Usmar, V.M., Graham, A. and Moncada, S. Peroxynitrite and atherosclerosis. Biochem. Soc. Trans. 21 (1993) 358–362.

    PubMed  CAS  Google Scholar 

  15. Olas, B., Nowak, P., Kolodziejczyk, J., Ponczek, M. and Wachowicz, B. Protective effects of resveratrol against oxidative/nitrative modifications of plasma proteins and lipids exposed to peroxynitrite. J. Nutr. Biochem. 17 (2005) 96–102.

    Article  PubMed  Google Scholar 

  16. Olas, B., Nowak, P., Kolodziejczyk, J. and Wachowicz, B. The effects of antioxidants on peroxynitrite-induced changes in platelet proteins. Thromb. Res. 113 (2004) 399–406.

    Article  PubMed  CAS  Google Scholar 

  17. Khan, J., Brennand, D.M., Bradley, N., Gao, B., Bruckdorfer, R. and Jacobs, M. 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochem. J. 330 (1998) 795–801.

    PubMed  CAS  Google Scholar 

  18. Buss, H., Chan, T.P., Sluis, K.B., Domigan, N.M. and Winterbourn, C.C. Protein carbonyl measurement by a sensitive ELISA method. Free Rad. Biol. Med. 23 (1997) 361–366.

    Article  PubMed  CAS  Google Scholar 

  19. Levine, R.L. Carbonyl modified proteins in cellular regulation, aging, and disease. Free Rad. Biol. Med. 32 (2002) 790–796.

    Article  PubMed  CAS  Google Scholar 

  20. Wachowicz, B. and Kustron, J. Effect of cisplatin on lipid peroxidation in pig blood platelets. Cytobios 70 (1992) 41–47.

    PubMed  CAS  Google Scholar 

  21. Lupidi, G., Angeletti, M., Eleuteri, A.M., Tacconi, L., Coletta, M. and Fioretti, E. Peroxynitrite-mediated oxidation of fibrinogen inhibits clot formation. FEBS Lett. 462 (1999) 236–240.

    Article  PubMed  CAS  Google Scholar 

  22. Pignatelli, B., Li, C.Q., Boffetta, P., Chen, Q., Ahrens, W., Nyberg, F., Mukeria, A., Bruske-Hohlfeld, I., Fortes, C., Constantinescu, V., Ischiropoulos, H. and Ohshima, H. Nitrated and oxidized plasma proteins in smokers and lung cancer patients. Cancer Res. 61 (2001) 778–784.

    PubMed  CAS  Google Scholar 

  23. Pannala, A.S., Rice-Evans, C.A., Halliwell, B. and Singh, S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem. Biophys. Res. Commun. 232 (1997) 164–168.

    Article  PubMed  CAS  Google Scholar 

  24. Radi, R., Beckman, J.S., Bush, K.M. and Freeman, B.A. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288 (1991) 481–487.

    Article  PubMed  CAS  Google Scholar 

  25. Klotz, L.O. and Sies, H. Defenses against peroxynitrite: selenocompounds and flavonoids. Toxicol. Lett. 140 (2003) 125–132.

    Article  PubMed  Google Scholar 

  26. Dinis, T.C., Santosa, C.L. and Almeida, L.M. The apoprotein is the preferential target for peroxynitrite-induced LDL damage protection by dietary phenolic acids. Free Radic. Res. 36 (2002) 531–543.

    Article  PubMed  CAS  Google Scholar 

  27. Sies, H., Klotz, L.O., Sharov, V.S., Assmann, A. and Briviba, K. Protection against peroxynitrite by selenoproteins. Z. Naturforsch. 53 (1998) 228–232.

    CAS  Google Scholar 

  28. Assmann, A., Briviba, K. and Sies, H. Reduction of methionine selenoxide to selenomethionine by glutathione. Arch. Biochem. Biophys. 349 (1998) 201–203.

    Article  PubMed  CAS  Google Scholar 

  29. Mouithys-Mickalad, M.A., Faez, J.M., Chistiaens, L., Kohnen, S., Deby, C., Hoebeke, M., Lamy, M. and Deby-Dupont, G. In vitro evaluation of glutathione peroxidase (GPx)-like activity and antioxidant properties of some Ebselen analogues. Redox. Rep. 9 (2004) 81–87.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of General Biochemistry, University of łódź, Banacha 12/16, 90-237, łódź, Poland

    Paweł Nowak, Joanna Saluk-Juszczak, Beata Olas, Joanna Kołodziejczyk & Barbara Wachowicz

Authors
  1. Paweł Nowak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Joanna Saluk-Juszczak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Beata Olas
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Joanna Kołodziejczyk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Barbara Wachowicz
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Paweł Nowak.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nowak, P., Saluk-Juszczak, J., Olas, B. et al. The protective effects of selenoorganic compounds against peroxynitrite-induced changes in plasma proteins and lipids. Cell. Mol. Biol. Lett. 11, 1–11 (2006). https://doi.org/10.2478/s11658-006-0001-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11658-006-0001-y

Key words

Cellular & Molecular Biology Letters

ISSN: 1689-1392

Contact us