ESR spin trapping of a carbon-centered free radical from agonist-stimulated human platelets

Free Radical Biology and Medicine

Volumn 39, Issue 2, 2005, Pages 237-248

  Chou, Duen Suey ^a   Hsiao, George ^a   Shen, Ming Yi ^a   Tsai, Yan Jyu ^a   Chen, Tzeng Fu ^a   Sheu, Joen Rong ^a  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Carbon centered free radical; Electron spin resonance; Peroxides; Platelets; Prostaglandin H synthase

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ARACHIDONIC ACID; CARBON; FREE RADICAL; GLUTATHIONE; NITROXIDE; PEROXIDE; POTASSIUM CYANIDE; PRONASE; PROSTAGLANDIN; PROSTAGLANDIN SYNTHASE; THROMBIN;

ARTICLE; BIOSYNTHESIS; CATALYSIS; DIGESTION; ELECTRON SPIN RESONANCE; ENZYME ACTIVITY; HUMAN; HUMAN CELL; INCUBATION TIME; NORMAL HUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; SPIN TRAPPING; SYNTHESIS; THROMBOCYTE; THROMBOCYTE AGGREGATION;

ARACHIDONIC ACID; BLOOD PLATELETS; CARBON; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; GLUTATHIONE; HUMANS; MODELS, BIOLOGICAL; NITRIC OXIDE; NITROGEN OXIDES; PEROXIDES; PLATELET AGGREGATION; PROSTAGLANDINS; TIME FACTORS;

EID: 20444444693     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2005.03.011     Document Type: Article

References (51)

1. T. Miyamoto, N. Ogino, S. Yamamoto, and O. Hayaishi Purification of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes J. Biol. Chem. 251 1976 2629 2636
2. W.L. Smith, D.L. DeWitt, and R.M. Garavito Cyclooxygenases: structural, cellular, and molecular biology Annu. Rev. Biochem. 69 2000 145 182
3. R. Karthein, R. Dietz, W. Nastainczyk, and H.H. Ruf Higher oxidation states of prostaglandin H synthase: EPR study of a transient tyrosyl radical in the enzyme during the peroxidase reaction Eur. J. Biochem. 171 1988 313 320
4. R.W. Egan, P.H. Gale, W.J. VandenHeuvel, E.M. Baptista, and F.A. Kuehl Jr. Mechanism of oxygen transfer by prostaglandin hydroperoxidase J. Biol. Chem. 255 1980 323 326
5. L.J. Marnett, P.H. Siedlik, and L.W. Fung Oxidation of phenidone and BW755C by prostaglandin endoperoxide synthetase J. Biol. Chem. 257 1982 6957 6964
6. P.R. West, L.S. Harman, P.D. Josephy, and R.P. Mason Acetaminophen: enzymatic formation of a transient phenoxyl free radical Biochem. Pharmacol. 33 1984 2933 2936
7. T.E. Eling, R.P. Mason, and K. Sivarajah The formation of aminopyrine cation radical by the peroxidase activity of prostaglandin H synthase and subsequent reactions of the radical J. Biol. Chem. 260 1985 1601 1607
8. D. Ross, R.J. Mehlhorn, P. Moldeus, and M.T. Smith Metabolism of diethylstilbestrol by horseradish peroxidase and prostaglandin-H synthase: generation of a free radical intermediate and its interaction with glutathione J. Biol. Chem. 260 1985 16210 16214
9. L.J. Marnett, P. Wlodawer, and B. Samuelsson Light emission during the action of prostaglandin synthetase Biochem. Biophys. Res. Commun. 60 1974 1286 1294
10. B. Samuelsson Prostaglandins and thromboxanes Recent Prog. Horm. Res. 34 1978 239 258
11. F. Bartoli, H.K. Lin, F. Ghomashchi, M.H. Gelb, M.K. Jain, and R. Apitz-Castro Tight binding inhibitors of 85-kDa phospholipase A2 but not 14-kDa phospholipase A2 inhibit release of free arachidonate in thrombin-stimulated human platelets J. Biol. Chem. 269 1994 15625 15630
12. 3H]arachidonic acid and changes in cytosolic free calcium in fura-2-loaded human platelets stimulated by ionomycin and collagen Biochem. J. 235 1986 869 877
13. V.B. O'Donnell, B. Coles, M.J. Lewis, B.C. Crews, L.J. Marnett, and B.A. Freeman Catalytic consumption of nitric oxide by prostaglandin H synthase-1 regulates platelet function J. Biol. Chem. 275 2000 38239 38244
14. G. Hsiao, M.Y. Shen, and K.H. Lin Inhibitory activity of kinetin on free radical formation of activated platelets in vitro and on thrombus formation in vivo Eur. J. Pharmacol. 465 2003 281 287
15. L. Iuliano, J.Z. Pedersen, D. Pratico, G. Rotilio, and F. Violi Role of hydroxyl radicals in the activation of human platelets Eur. J. Biochem. 221 1994 695 704
16. J.L. Zweier, R. Broderick, P. Kuppusamy, S. Thompson-Gorman, and G.A. Lutty Determination of the mechanism of free radical generation in human aortic endothelial cells exposed to anoxia and reoxygenation J. Biol. Chem. 269 1994 24156 24162
17. C. Bernofsky, and B.M. Bandara Spin trapping endogenous radicals in MC-1010 cells: evidence for hydroxyl radical and carbon-centered ascorbyl radical adducts Mol. Cell Biochem. 148 1995 155 164
18. S.Y. Qian, H.P. Wang, F.Q. Schafer, and G.R. Buettner EPR detection of lipid-derived free radicals from PUFA, LDL, and cell oxidations Free Radic. Biol. Med. 29 2000 568 579
19. R.W. Egan, P.H. Gale, and F.A. Kuehl Jr. Reduction of hydroperoxides in the prostaglandin biosynthetic pathway by a microsomal peroxidase J. Biol. Chem. 254 1979 3295 3302
20. S. Ohki, N. Ogino, S. Yamamoto, and O. Hayaishi Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes J. Biol. Chem. 254 1979 829 836
21. M. d'Arcy Doherty, I. Wilson, P. Wardman, J. Basra, L.H. Patterson, and G.M. Cohen Peroxidase activation of 1-naphthol to naphthoxy or naphthoxy-derived radicals and their reaction with glutathione Chem. Biol. Interact. 58 1986 199 215
22. S.D. Nelson, D.C. Dahlin, E.J. Rauckman, and G.M. Rosen Peroxidase-mediated formation of reactive metabolites of acetaminophen Mol. Pharmacol. 20 1981 195 199
23. A. Bosia, P. Spangenberg, D. Ghigo, R. Heller, W. Losche, G.P. Pescarmona, and U. Till Effect of GSH depletion by 1-chloro-2,4-dinitrobenzene on human platelet aggregation, arachidonic acid oxidative metabolism and cytoskeletal proteins Thromb. Res. 37 1985 423 434
24. J. Schreiber, G.L. Foureman, M.F. Hughes, R.P. Mason, and T.E. Eling Detection of glutathione thiyl free radical catalyzed by prostaglandin H synthase present in keratinocytes: study of co-oxidation in a cellular system J. Biol. Chem. 264 1989 7936 7943
25. R.V. Panganamala, J.S. Miller, E.T. Gwebu, H.M. Sharma, and D.G. Cornwell Differential inhibitory effects of vitamin E and other antioxidants on prostaglandin synthetase, platelet aggregation and lipoxidase Prostaglandins 14 1977 261 271
26. E.J. Langford, A.S. Brown, and R.J. Wainwright Inhibition of platelet activity by S-nitrosoglutathione during coronary angioplasty Lancet 344 1994 1458 1460
27. M.P. Gordge, J.S. Hothersall, and A.A. Noronha-Dutra Evidence for a cyclic GMP-independent mechanism in the anti-platelet action of S-nitrosoglutathione Br. J. Pharmacol. 124 1998 141 148
28. R.W. Egan, J. Paxton, and F.A. Kuehl Jr. Mechanism for irreversible self-deactivation of prostaglandin synthetase J. Biol. Chem. 251 1976 7329 7335
29. B. Kalyanaraman, R.P. Mason, B. Tainer, and T.E. Eling The free radical formed during the hydroperoxide-mediated deactivation of ram seminal vesicles is hemoprotein-derived J. Biol. Chem. 257 1982 4764 4768
30. L.M. Landino, and L.J. Marnett Mechanism of hydroperoxide reduction by mangano-prostaglandin endoperoxide synthase Biochemistry 35 1996 2637 2643
31. L.J. Marnett Cyclooxygenase mechanisms Curr. Opin. Chem. Biol. 4 2000 545 552
32. W.L. Smith, and W.E. Lands Oxygenation of polyunsaturated fatty acids during prostaglandin biosynthesis by sheep vesicular gland Biochemistry 11 1972 3276 3285
33. C. Su, M. Sahlin, and E.H. Oliw A protein radical and ferryl intermediates are generated by linoleate diol synthase, a ferric hemeprotein with dioxygenase and hydroperoxide isomerase activities J. Biol. Chem. 273 1998 20744 20751
34. G. Wu, C. Wei, R.J. Kulmacz, Y. Osawa, and A.L. Tsai A mechanistic study of self-inactivation of the peroxidase activity in prostaglandin H synthase-1 J. Biol. Chem. 274 1999 9231 9237
35. G. Wu, J.L. Vuletich, R.J. Kulmacz, Y. Osawa, and A.L. Tsai Peroxidase self-inactivation in prostaglandin H synthase-1 pretreated with cyclooxygenase inhibitors or substituted with mangano protoporphyrin IX J. Biol. Chem. 276 2001 19879 19888
36. G. Wu, R.J. Kulmacz, and A.L. Tsai Cyclooxygenase inactivation kinetics during reaction of prostaglandin H synthase-1 with peroxide Biochemistry 42 2003 13772 13777
37. C. Calzada, E. Vericel, and M. Lagarde Low concentrations of lipid hydroperoxides prime human platelet aggregation specifically via cyclo-oxygenase activation Biochem. J. 325 Pt. 2 1997 495 500
38. D. Pratico, L. Iuliano, F.M. Pulcinelli, M.S. Bonavita, P.P. Gazzaniga, and F. Violi Hydrogen peroxide triggers activation of human platelets selectively exposed to nonaggregating concentrations of arachidonic acid and collagen J. Lab. Clin. Med. 119 1992 364 370
39. G. Hecker, J. Utz, R.J. Kupferschmidt, and V. Ullrich Low levels of hydrogen peroxide enhance platelet aggregation by cyclooxygenase activation Eicosanoids 4 1991 107 113
40. D. Aharony, J.B. Smith, and M.J. Silver Regulation of arachidonate-induced platelet aggregation by the lipoxygenase product, 12-hydroperoxyeicosatetraenoic acid Biochim. Biophys. Acta 718 1982 193 200
41. E. Vericel, and M. Lagarde 15-Hydroperoxyeicosatetraenoic acid inhibits human platelet aggregation Lipids 15 1980 472 474
42. D. Pietraforte, and M. Minetti Direct ESR detection or peroxynitrite-induced tyrosine-centred protein radicals in human blood plasma Biochem. J. 325 Pt 3 1997 675 684
43. 2-activated metmyoglobin and other proteins Free Radic. Biol. Med. 23 1997 754 761
44. G. Lassmann, B. Liermann, W. Lehmann, H. Graetz, A. Koberling, and P. Langen Ribonucleotide reductase in ascites tumour cells detected by electron paramagnetic resonance spectroscopy Biochem. Biophys. Res. Commun. 132 1985 1137 1143
45. M. Sahlin, G. Lassmann, S. Potsch, A. Slaby, B.M. Sjoberg, and A. Graslund Tryptophan radicals formed by iron/oxygen reaction with Escherichia coli ribonucleotide reductase protein R2 mutant Y122F J. Biol. Chem. 269 1994 11699 11702
46. D.C. Goodwin, M.R. Gunther, and L.C. Hsi Nitric oxide trapping of tyrosyl radicals generated during prostaglandin endoperoxide synthase turnover: detection of the radical derivative of tyrosine 385 J. Biol. Chem. 273 1998 8903 8909
47. 2: involvement of a thiyl radical produced at cysteine 110 J. Biol. Chem. 275 2000 20391 20398
48. M.E. Hemler, and W.E. Lands Evidence for a peroxide-initiated free radical mechanism of prostaglandin biosynthesis J. Biol. Chem. 255 1980 6253 6261
49. L.J. Marnett, P.H. Siedlik, and L.W. Fung Oxidation of phenidone and BW755C by prostaglandin endoperoxide synthetase J. Biol. Chem. 257 1982 6957 6964
50. J.L. Humes, C.A. Winter, S.J. Sadowski, and F.A. Kuehl Jr. Multiple sites on prostaglandin cyclooxygenase are determinants in the action of nonsteroidal antiinflammatory agents Proc. Natl. Acad. Sci. USA 78 1981 2053 2056
51. P. Nowak, B. Olas, E. Bald, R. Glowacki, and B. Wachowicz Peroxynitrite-induced changes of thiol groups in human blood platelets Platelets 14 2003 375 379