Inhibitory effect of ebselen on lactate dehydrogenase activity from mammals: a comparative study with diphenyl diselenide and diphenyl ditelluride

References

• Arteel, G. E., Sies, H. (2001). The biochemistry of selenium and the glutathione system. Environ Toxicol Pharmacol 10:153–158.
   PubMed Web of Science ®Google Scholar
• Abad-Zapatero, C., Griffith, J. P., Sussman, J. L., Rossman, M. G. (1987). Refined crystal structure of dogfish M4 apo-lactate dehydrogenase. J Mol Biol 198:445–467.
   PubMed Web of Science ®Google Scholar
• Barbosa, N. B., Rocha, J. B., Soares, J. C., Wondracek, D. C., Gonçalves, J. F., Schetinger, M. R., Nogueira, C. W. (2008). Dietary diphenyl diselenide reduces the STZ-induced toxicity. Food Chem Toxicol 46:186–194.
   PubMed Web of Science ®Google Scholar
• Delanty, N., Dichter, M. A. (2000). Antioxidant therapy in neurologic disease. Arch Neurol 57:1265–1270.
   PubMed Web of Science ®Google Scholar
• Dixon, M., Webb, E. C. (1964). Enzyme inhibitors. In: Enzymes, vol 2 (pp 315–329 ). London: Longmans.
   Google Scholar
• Ellman, G. L. (1959). Tissue sulphydryl groups. Arch Biochem Biophys 82: 70–77.
   PubMed Web of Science ®Google Scholar
• Engman, L. (1989). Expedient synthesis of ebselen and related compounds. J Org Chem 54:2964–2966.
   Web of Science ®Google Scholar
• Engman, L., Andersson, C., Morgenstern, R., Cotgreave, I. A., Andersson, C. M., Hallberg, A. (1994) Evidence for a common selenolate intermediate in the glutathione peroxidase-like catalysis of A-(phenylselenenyl) ketones and diphenyl diselenide. Tetrahedron 50:2929–2938.
   Web of Science ®Google Scholar
• Farina, M., Barbosa, N. B., Nogueira, C. W., Folmer, V., Zeni, G., Andrade, L. H. et al. (2002). Reaction of diphenyl diselenide with hydrogen peroxide and inhibition of delta-aminolevulinate dehydratase from rat liver and cucumber leaves. Braz J Med Biol Res 35:623–631.
   PubMed Web of Science ®Google Scholar
• Farina, M., Folmer, V., Bolzan, R. C., Andrade, L. H., Zeni, G., Braga, A. L. et al. (2001). Selenoxides inhibit delta-aminolevulinic acid dehydratase. Toxicol Lett 119:27–37.
   PubMed Web of Science ®Google Scholar
• Galet, V., Bernier, J.L., Henichart, J.P., Lesieur, D., Abadie, C., Rochette, L., Lindenbaum, A., Chalas, J., de la Faverie, J.F.R., Pfeiffer, B., Renard, P. (1994). Benzoselenazolinone derivatives designed to be glutathione peroxidase mimetics feature inhibition of cyclooxygenase/5-lipoxygenase pathways and anti-inflammatory activity. J Med Chem 119:2903–2911.
   Google Scholar
• Golombieski, R. M., Graichen, D. A., Pivetta, L. A., Nogueira, C. W., Loreto, E. L., Rocha, J. B. (2008) Diphenyl diselenide [(PhSe)2] inhibits Drosophila melanogaster delta-aminolevulinate dehydratase (delta-ALA-D) gene transcription and enzyme activity. Comp Biochem Physiol C Toxicol Pharmacol 147:198–204.
   PubMed Web of Science ®Google Scholar
• Hewitt, C. O., Eszes, C. M., Sessions, R. B., Moreton, K. M., Dafforn, T. R., Takei, J., et al. (1999). A general method for relieving substrate inhibition in lactate dehydrogenases. Prot Eng 12:491–496.
   PubMedGoogle Scholar
• Imai, H., Graham, D. I., Masayasu, H., Macrae, I. M. (2003). Antioxidant ebselen reduces oxidative damage in focal cerebral ischemia. Free Radic Biol Med 34:56–63.
   PubMed Web of Science ®Google Scholar
• Kade, I. J., Paixao, M. W., Rodrigues, O. E., Ibukun, E. O., Braga, A. L., Zeni, G., et al. (2009). Studies on the antioxidant effect and interaction of diphenyl diselenide and dicholesteroyl diselenide with hepatic delta-aminolevulinic acid dehydratase and isoforms of lactate dehydrogenase. Toxicol In Vitro 23:14–20.
   PubMed Web of Science ®Google Scholar
• Le Bras, G., Garel, J. R. (1991). Properties of D-lactate dehydrogenase from Lactobacillus bulgaricus: a possible different evolutionary origin for the D- and L-lactate dehydrogenases. FEMS Microbiol Lett 63:89–93.
   PubMedGoogle Scholar
• Maciel, E. N., Bolzan, R. C., Braga, A. L., Rocha, J. B. (2000). Diphenyl diselenide and diphenyl ditelluride differentially affect delta-aminolevulinate dehydratase from liver, kidney, and brain of mice. J Biochem Mol Toxicol 14:310–319.
   PubMed Web of Science ®Google Scholar
• Mugesh, G., du Mont, W. W., Sies, H. (2001). Chemistry of biologically important synthetic organoselenium compounds. Chem Rev 101:2125–2179.
   PubMed Web of Science ®Google Scholar
• Mugesh, G., Singh, H. B. (2000). Synthetic organoselenium compounds as antioxidants: glutathione peroxidase activity. Chem Soc Rev 29:347–357.
   Web of Science ®Google Scholar
• Nogueira, C. W., Borges, V. C., Zeni, G., Rocha, J. B. (2003). Organochalcogens effects on delta-aminolevulinate dehydratase activity from human erythrocytic cells in vitro. Toxicology 191:169–178.
   PubMed Web of Science ®Google Scholar
• Nogueira, C. W., Zeni, G., Rocha, J. B. (2004). Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem Rev 104:6255–6285.
   PubMed Web of Science ®Google Scholar
• Ozaki, M., Nakamura, M., Teraoka, S., Ota, K. (1997). Ebselen, a novel antioxidant compound, protects the rat liver from ischemia-reperfusion injury. Transpl Int 10:96–102.
   PubMed Web of Science ®Google Scholar
• Pamp, K., Bramey, T., Kirsch, M., De Groot, H., Petrat, F. (2005). NAD(H) enhances the Cu(II)-mediated inactivation of lactate dehydrogenase by increasing the accessibility of sulfhydryl groups. Free Radic Res 39:31–40.
   PubMed Web of Science ®Google Scholar
• Paulmier, C. (1986). Selenium reagents and intermediates in organic synthesis. Oxford, UK: Pergamon Books.
   Google Scholar
• Pereira, M. E., Bordignon, A. M., Burger, C., Huang, C. I., Rocha, J. B. (1991). Long-term treatment with 2,5-hexanedione has no effect on the specific activity of some brain and liver glycolytic enzymes of adult rats. Braz J Med Biol Res 24:735–740.
   PubMed Web of Science ®Google Scholar
• Petragnani, N. (1994). Tellurium in organic synthesis (p 248). San Diego, California, USA: Academic Press.
   Google Scholar
• Phillips, D., Blake, C. C. F., Watson, H. C. (1981). The enzymes of glycolysis: structure, activity, and evolution. Philos Trans R Soc Lond B Biol Sci 293:1–214.
   PubMedGoogle Scholar
• Prigol, M., Wilhelm, E. A., Schneider, C. C., Nogueira, C. W. (2007). Involvement of oxidative stress in seizures induced by diphenyl diselenide in rat pups. Brain Res 1147:226–232.
   PubMed Web of Science ®Google Scholar
• Puntel, R. L., Roos, D. H., Paixao, M. W., Braga, A. L., Zeni, G., Nogueira, C. W., et al. (2007). Oxalate modulates thiobarbituric acid reactive species (TBARS) production in supernatants of homogenates from rat brain, liver, and kidney: effect of diphenyl diselenide and diphenyl ditelluride. Chem Biol Interact 165:87–98.
   PubMed Web of Science ®Google Scholar
• Santos, F. W., Zeni, G., Rocha, J. B., Weis, S. N., Fachinetto, J. M., Favero, A. M., et al. (2005). Diphenyl diselenide reverses cadmium-induced oxidative damage on mice tissues. Chem Biol Interact 151:159–165.
   PubMed Web of Science ®Google Scholar
• Sies, H. (1995). Ebselen. Meth Enzymol 252:341–342.
   PubMed Web of Science ®Google Scholar
• Vinals, C., De Bolle, X., Depiereux, E., Feytmans, E. (1995). Knowledge-based modeling of the D-lactate dehydrogenase three-dimensional structure. Proteins 21:307–318.
   PubMed Web of Science ®Google Scholar
• Zhao, R., Holmgren, A. (2002). A novel antioxidant mechanism of ebselen involving ebselen diselenide, a substrate of mammalian thioredoxin and thioredoxin reductase. J Biol Chem 277:39456–39462.
   PubMed Web of Science ®Google Scholar
• Zhao, R., Masayasu, H., Holmgren, A. (2002). Ebselen: a substrate for human thioredoxin reductase strongly stimulating its hydroperoxide reductase activity and a superfast thioredoxin oxidant. Proc Natl Acad Sci U S A 99:8579–8584.
   PubMed Web of Science ®Google Scholar
• Zheng, Y. B., Wang, Z., Chen, B. Y., Wang, X. C. (2003). Multiple effects of chemical reagent on enzyme: o-phthalaldehyde-induced inactivation, dissociation, and partial unfolding of lactate dehydrogenase from pig heart. Int J Biol Macromol 32: 191–197.
   PubMed Web of Science ®Google Scholar