Ebselen as a peroxynitrite scavenger in vitro and ex vivo

Biochemical Pharmacology

Volumn 59, Issue 2, 2000, Pages 153-160

  Daiber, Andreas ^a   Zou, Ming Hui ^a   Bachschmid, Markus ^a   Ullrich, Volker ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Antioxidants; Glutathione adduct; Prostacyclin synthase; Selenocompounds; Tyrosine nitration

Indexed keywords

EBSELEN; GLUTATHIONE; PEROXYNITRITE; PROSTACYCLIN; PROSTACYCLIN SYNTHASE; TYROSINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; IN VITRO STUDY; MICROSOME; NITRATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; VASOCONSTRICTION; VASODILATATION;

ANIMALS; ANTIOXIDANTS; AORTA; AZOLES; CATTLE; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INTERACTIONS; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; INTRAMOLECULAR OXIDOREDUCTASES; NITRATES; ORGANOSELENIUM COMPOUNDS; OXIDANTS; SULFHYDRYL COMPOUNDS;

EID: 0033990512     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00309-3     Document Type: Article

References (41)

1. Moncada S., Palmer R.M.J., Higgs E.A. Nitric oxide Physiology, pathophysiology and pharmacology . Pharmacol Rev. 43:1991;109-142.
2. Nathan C. Nitric oxide as a secretory product of mammalial cells. FASEB J. 6:1992;3051-3064.
3. Beckman J.S. Oxidative damage and tyrosine nitration from peroxynitrite. Chem Res Toxicol. 9:1996;836-844.
4. Kissner R., Nauser T., Bugnon P., Lye P.G., Koppenol W.H. Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis. Chem Res Toxicol. 10:1997;1285-1292.
5. Epe B., Ballmaier D., Roussyn I., Briviba K., Sies H. DNA damage by peroxynitrite characterized with DNA repair enzymes. Nucleic Acids Res. 24:1996;4105-4110.
6. Heinecke J.W. Mechanisms of oxidative damage of low density lipoprotein in human atherosclerosis. Curr Opin Lipidol. 8:1997;268-274.
7. Ischiropoulos H., Al-Mehdi A.B. Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 364:1995;279-282.
8. Packer L (Ed.), Nitric Oxide: Part B Physiological and pathological processes. Methods Enzymol 269: 1-375, 1996.
9. Beckman J.S., Koppenol W.H. Nitric oxide, superoxide and peroxynitrite The good, the bad and the ugly . Am J Physiol. 271:1996;C1424-C1437.
10. Crow J.P., Beckman J.S., McCord J.M. Sensitivity of the essential zinc-thiolate moiety of yeast alcohol dehydrogenase to hypochlorite and peroxynitrite. Biochemistry. 34:1995;3544-3552.
11. Vogt W. Oxidation of methionyl residues in proteins Tools, targets, and reversal . Free Radic Biol Med. 18:1995;93-105.
12. Crow J.P., Ye Y.Z., Strong M., Kirk M., Barnes S., Beckman J.S. Superoxide dismutase catalyzes nitration of tyrosine by peroxynitrite in the rod and head domains of neurofilament-L. J Neurochem. 69:1997;1945-1953.
13. Zou M.H., Ullrich V. Peroxynitrite formed by simultaneous generation of nitric oxide and superoxide selectively inhibits bovine aortic prostacyclin synthase. FEBS Lett. 382:1996;101-104.
14. MacMillan-Crow L.A., Crow J.P., Kerby J.D., Beckman J.S., Thompson A. Nitration and inactivation of manganese superoxide dismutase in chronic rejection of human renal allografts. Proc Natl Acad Sci USA. 93:1996;11853-11858.
15. Wang P., Zweier J.L. Measurement of nitric oxide and peroxynitrite generation in the postischemic heart. J Biol Chem. 271:1996;29223-29230.
16. Christen A.A., Woodall M.K., Southwell-Keely P.T., Duncan W., Ames B.N. Reactions of peroxynitrite with alpha-tocopherol. Proc Natl Acad Sci USA. 94:1997;3218-3223.
17. Bartlett D., Church D.F., Bounds P.L., Koppenol W.H. The kinetics of the oxidation of L-ascorbic acid by peroxynitrite. Free Radic Biol Med. 18:1995;85-92.
18. Squadrito G.L., Jin X., Pryor W.A. Stopped-flow kinetic study of the reaction of ascorbic acid with peroxynitrite. Arch Biochem Biophys. 322:1995;53-59.
19. Arteel G.E., Briviba K., Sies H. Protection against peroxynitrite. FEBS Lett. 445:1999;226-230.
20. Zou M.H., Martin C., Ullrich V. Tyrosine nitration as a mechanism of selective inactivation of prostacyclin synthase by peroxynitrite. Biol Chem. 378:1997;707-713.
21. Zou M.H., Klein T., Pasquet J.P., Ullrich V. Interleukin 1beta decreases prostacyclin synthase activity in rat mesangial cells via endogenous peroxynitrite formation. Biochem J. 336:1998;507-512.
22. Mehl M., Daiber A., Herold S., Shoun H., Ullrich V. Peroxynitrite reaction with heme proteins. Nitric Oxide. 3:1999;142-152.
23. Daiber A., Mehl M., Ullrich V. New aspects in the reaction mechanism of phenol with peroxynitrite The role of phenoxy radicals . Nitric Oxide. 2:1998;259-269.
24. Masumoto H., Kissner R., Koppenol W.H., Sies H. Kinetic study of the reaction of ebselen with peroxynitrite. FEBS Lett. 398:1996;179-182.
25. Hara S., Miyata A., Yokoyama C., Inoue H., Brugger R., Lottspeich F., Ullrich V., Tanabe T. Isolation and molecular cloning of prostacyclin synthase from bovine endothelial cells. J Biol Chem. 31:1994;19897-19903.
26. Bunting S., Gryglewski R., Moncada S., Vane J.R. Arterial walls generate from prostaglandin endoperoxides a substance (prostaglandin X) which relaxes strips of mesenteric and coeliac arteries and inhibits platelet aggregation. Prostaglandins. 12:1976;897-913.
27. Zou M.H., Jendral M., Ullrich V. Peroxynitrite induces prostaglandin endoperoxide dependent-vasospasm in bovine coronary arteries via nitration of prostacyclin synthase. Br J Pharmacol. 126:1999;1283-1292.
28. Ullrich V., Weber P., Meisch F., von Appen F. Ebselen-binding equilibria between plasma and target proteins. Biochem Pharmacol. 52:1996;15-19.
29. Haenen G., De Roorj B., Vermeulen N., Bast A. Mechanism of the reaction of ebselen with endogenous thiols. Mol Pharmacol. 37:1989;412-422.
30. Masumoto H., Sies H. The reaction with ebselen with peroxynitrite. Chem Res Toxicol. 9:1996;262-267.
31. Pfeiffer S., Gorren A.C.F., Schmidt K., Werner E.R., Hansert B., Bohle D.S., Mayer B. Metabolic fate of peroxynitrite in aqueous solution. J Biol Chem. 272:1997;3465-3470.
32. Hughes MN and Niklin HG, The chemistry of pernitrides. I. Kinetics of decomposition of pernitrous acid. J Am Soc (Part A): 450-462, 1968.
33. Scorza G., Minetti M. One-electron oxidation pathway of thiols by peroxynitrite in biological fluids Bicarbonate and ascorbate promote the formation of albumin disulfide dimers in human blood plasma . Biochem J. 329:1998;405-413.
34. Ramezanian M.S., Padmaja S., Koppenol W.H. Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem Res Toxicol. 9:1996;232-240.
35. Lemercier J.N., Padmaja S., Cueto R., Squadrito G.L., Uppu R.M., Pryor W.A. Carbon dioxide modulation of hydroxylation and nitration of phenol by peroxynitrite. Arch Biochem Biophys. 345:1997;160-170.
36. Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite oxidations of sulfhydryls. J Biol Chem. 266:1991;4244-4250.
37. Gow A.J., Buerk D.G., Ischiropoulos H. A novel reaction mechanism for the formation of S-nitrosothiol in vivo. J Biol Chem. 272:1997;2841-2845.
38. Masumoto H., Sies H. The reaction of 2-(methylseleno)benzanilide with peroxynitrite. Chem Res Toxicol. 9:1996;1057-1062.
39. Briviba K., Roussyn I., Sharov V.S., Sies H. Attenuation of oxidation and nitration reactions of peroxynitrite by selenomethionine, selenocysteine and ebselen. Biochem J. 319:1996;13-15.
40. Zou M.H., Leist M., Ullrich V. Selective nitration of prostacyclin synthase and defective vasorelaxation in atherosclerotic bovine coronary arteries. Am J Pathol. 154:1999;1354-1365.
41. Szabo C., Salzman A.L., Ischiropoulos H. Endotoxin triggers the expression of an inducible isoform of nitric oxide synthase and the formation of peroxynitrite in the rat aortae in vivo. FEBS Lett. 363:1995;235-238.