Reprint of "Oxidative alterations of cyclooxygenase during atherogenesis" [Prostag. Oth. Lipid. M. 80 (2006) 1-14]

Prostaglandins and Other Lipid Mediators

Volumn 82, Issue 1-4, 2007, Pages

  Upmacis, Rita K ^a   Deeb, Ruba S ^a   Hajjar, David P ^a  

^a Weill Cornell Medical College of Cornell University   (United States)

Author keywords

Atherosclerosis; Cyclooxygenase; Cysteine oxidation; Heme oxidation; Nitric oxide; Nitrogen oxides; Peroxynitrite; Prostaglandin H2 synthase; S Nitrosation

Indexed keywords

ERROR; REVIEW;

EID: 33845467527     PISSN: 10988823     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1098-8823(06)00182-1     Document Type: Review

References (110)

1. Spencer A.G., Woods J.W., Arakawa T., Singer I.I., and Smith W.L. Subcellular localization of prostaglandin endoperoxide H synthases-1 and -2 by immunoelectron microscopy. J Biol Chem 273 (1998) 9886-9893
2. 2 synthase-1. Nature 367 (1994) 243-249
3. Luong C., Miller A., Barnett J., Chow J., Ramesha C., and Browner M.F. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 3 (1996) 927-933
4. 2 enzymes. Prostagland Other Lipid Mediat 68/69 (2002) 3-58
5. Garavito R.M., Malkowski M.G., and De Witt D.L. The structures of prostaglandin endoperoxide H synthases-1 and -2. Prostagland Other Lipid Mediat 69 (2002) 129-152
6. Smith W.L., and Song I. The enzymology of prostaglandin endoperoxide H synthases-1 and -2. Prostagland Other Lipid Mediat 69 (2002) 115-128
7. Oshima M., Dinchuk J.E., Kargman S.L., et al. Suppression of intestinal polyposis in Apc delta716 knockout mice by inhibition of cyclooxygenase 2 (COX-2). Cell 87 (1996) 803-809
8. Baker C.S., Hall R.J., Evans T.J., et al. Cyclooxygenase-2 is widely expressed in atherosclerotic lesions affecting native and transplanted human coronary arteries and colocalizes with inducible nitric oxide synthase and nitrotyrosine particularly in macrophages. Arterioscler Thromb Vasc Biol 19 (1999) 646-655
9. Schonbeck U., Sukhova G.K., Graber P., Coulter S., and Libby P. Augmented expression of cyclooxygenase-2 in human atherosclerotic lesions. Am J Pathol 155 (1999) 1281-1291
10. Wu K. Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med 3 (2003) 107-112
11. Moncada S., Gryglewski R., Bunting S., and Vane J.R. An enzyme isolated from arteries transforms prostaglandin endoperoxides to an unstable substance that inhibits platelet aggregation. Nature 263 (1976) 663-665
12. Bombardier C., Laine L., Reicin A., et al. Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. VIGOR Study Group. N Engl J Med 343 (2000) 1520-1528
13. 2 and prostacyclin in the development of atherosclerosis in apoE-deficient mice. J Clin Invest 114 (2004) 784-794
14. Rolland P.H., Jouve R., Pellegrin E., Mercier C., and Serradimigni A. Alteration in prostacyclin and prostaglandin E2 production. Correlation with changes in human aortic atherosclerotic disease. Arteriosclerosis 4 (1984) 70-78
15. Serneri G.G., Masotti G., Poggesi L., Galanti G., Morettini A., and Scarti L. Reduced prostacyclin production in patients with different manifestations of ischemic heart disease. Am J Cardiol 49 (1982) 1146-1151
16. Fitz Gerald G.A., Smith B., Pedersen A.K., and Brash A.R. Increased prostacyclin biosynthesis in patients with severe atherosclerosis and platelet activation. N Engl J Med 310 (1984) 1065-1068
17. Pratico D., Cyrus T., Li H., and Fitz Gerald G.A. Endogenous biosynthesis of thromboxane and prostacyclin in 2 distinct murine models of atherosclerosis. Blood 96 (2000) 3823-3826
18. Salvemini D., Misko T.P., Masferrer J.L., Seibert K., Currie M.G., and Needleman P. Nitric oxide activates cyclooxygenase enzymes. Proc Natl Acad Sci USA 90 (1993) 7240-7244
19. Hajjar D.P., Lander H.M., Pearce S.F., Upmacis R.K., and Pomerantz K.B. Nitric oxide enhances prostaglandin-H synthase-1 activity by a heme-independent mechanism: evidence implicating nitrosothiols. J Am Chem Soc 117 (1995) 3340-3346
20. Maccarrone M., Putti S., and Finazzi Agro A. Nitric oxide donors activate the cyclo-oxygenase and peroxidase activities of prostaglandin H synthase. FEBS Lett 410 (1997) 470-476
21. Landino L.M., Crews B.C., Timmons M.D., Morrow J.D., and Marnett L.J. Peroxynitrite, the coupling product of nitric oxide and superoxide, activates prostaglandin biosynthesis. Proc Natl Acad Sci USA 93 (1996) 15069-15074
22. 2 synthase activity by nitrogen oxides. Biochemistry 38 (1999) 12505-12513
23. Kim S.F., Huri D.A., and Snyder S.H. Inducible nitric oxide synthase binds, S-nitrosylates, and activates cyclooxygenase-2. Science 310 (2005) 1966-1970
24. Kanner J., Harel S., and Granit R. Nitric oxide, an inhibitor of lipid oxidation by lipoxygenase, cyclooxygenase and hemoglobin. Lipids 27 (1992) 46-49
25. Curtis J.F., Reddy N.G., Mason R.P., Kalyanaraman B., and Eling T.E. Nitric oxide: a prostaglandin H synthase 1 and 2 reducing cosubstrate that does not stimulate cyclooxygenase activity or prostaglandin H synthase expression in murine macrophages. Arch Biochem Biophys 335 (1996) 369-376
26. Salvemini D., Settle S.L., Masferrer J.L., Seibert K., Currie M.G., and Needleman P. Regulation of prostaglandin production by nitric oxide: an in vivo analysis. Br J Pharmacol 114 (1995) 1171-1178
27. Sautebin L., Ialenti A., Ianaro A., and Di Rosa M. Modulation by nitric oxide of prostaglandin biosynthesis in the rat. Br J Pharmacol 114 (1995) 323-328
28. Nogawa S., Forster C., Zhang F., Nagayama M., Ross M.E., and Iadecola C. Interaction between inducible nitric oxide synthase and cyclooxygenase-2 after cerebral ischemia. Proc Natl Acad Sci USA 95 (1998) 10966-10971
29. Marnett L.J., Wright T.L., Crews B.C., Tannenbaum S.R., and Morrow J.D. Regulation of prostaglandin biosynthesis by nitric oxide is revealed by targeted deletion of inducible nitric-oxide synthase. J Biol Chem 275 (2000) 13427-13430
30. Davidge S.T., Baker P.N., Laughlin M.K., and Roberts J.M. Nitric oxide produced by endothelial cells increases production of eicosanoids through activation of prostaglandin H synthase. Circ Res 77 (1995) 274-283
31. Corbett J.A., Kwon G., Turk J., and McDaniel M.L. IL-1 beta induces the coexpression of both nitric oxide synthase and cyclooxygenase by islets of Langerhans: activation of cyclooxygenase by nitric oxide. Biochemistry 32 (1993) 13767-13770
32. Tetsuka T., Daphna-Iken D., Srivastava S.K., Baier L.D., Du Maine J., and Morrison A.R. Cross-talk between cyclooxygenase and nitric oxide pathways: prostaglandin E2 negatively modulates induction of nitric oxide synthase by interleukin 1. Proc Natl Acad Sci USA 91 (1994) 12168-12172
33. 2 production by vascular smooth muscle cells. Biochem Biophys Res Commun 194 (1993) 420-424
34. Tetsuka T., Daphna-Iken D., Miller B.W., Guan Z., Baier L.D., and Morrison A.R. Nitric oxide amplifies interleukin 1-induced cyclooxygenase-2 expression in rat mesangial cells. J Clin Invest 97 (1996) 2051-2056
35. Swierkosz T.A., Mitchell J.A., Warner T.D., Botting R.M., and Vane J.R. Co-induction of nitric oxide synthase and cyclo-oxygenase: interactions between nitric oxide and prostanoids. Br J Pharmacol 114 (1995) 1335-1342
36. Habib A., Bernard C., Lebret M., et al. Regulation of the expression of cyclooxygenase-2 by nitric oxide in rat peritoneal macrophages. J Immunol 158 (1997) 3845-3851
37. Beverelli F., Bea M.L., Puybasset L., Giudicelli J.F., and Berdeaux A. Chronic inhibition of NO synthase enhances the production of prostacyclin in coronary arteries through upregulation of the cyclooxygenase type 1 isoform. Fundam Clin Pharmacol 11 (1997) 252-259
38. Sun D., Huang A., Smith C.J., et al. Enhanced release of prostaglandins contributes to flow-induced arteriolar dilation in eNOS knockout mice. Circ Res 85 (1999) 288-293
39. Loscalzo J., and Welch G. Nitric oxide and its role in the cardiovascular system. Prog Cardiovasc Dis 38 (1995) 87-104
40. Buttery L.D., Springall D.R., Chester A.H., et al. Inducible nitric oxide synthase is present within human atherosclerotic lesions and promotes the formation and activity of peroxynitrite. Lab Invest 75 (1996) 77-85
41. 2. Acta Crystallogr 14 (1961) 1100-1101
42. Marnett L.J., Rowlinson S.W., Goodwin D.C., Kalgutkar A.S., and Lanzo C.A. Arachidonic acid oxygenation by COX-1 and COX-2. Mechanisms of catalysis and inhibition. J Biol Chem 274 (1999) 22903-22906
43. 2. Eur J Biochem 171 (1988) 321-328
44. Karthein R., Dietz R., Nastainczyk W., and Ruf H. 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) p313-p320
45. Tsai A.L., Palmer G., and Kulmacz R.J. Prostaglandin H synthase. Kinetics of tyrosyl radical formation and of cyclooxygenase catalysis. J Biol Chem 267 (1992) 17753-17759
46. Goodwin D.C., Gunther M.R., Hsi L.C., et al. 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 synthase nitration and suppresses eicosanoid production. Am J Pathol 168 (2006) 349-362
48. Schmidt P., Youhnovski N., Daiber A., et al. Specific nitration at tyrosine 430 revealed by high resolution mass spectrometry as basis for redox regulation of bovine prostacyclin synthase. J Biol Chem 278 (2003) 12813-12819
49. Guidarelli A., Palomba L., and Cantoni O. Peroxynitrite-mediated release of arachidonic acid from PC12 cells. Br J Pharmacol 129 (2000) 1539-1541
50. Upmacis R.K., Deeb R.S., Resnick M.J., et al. Involvement of the mitogen-activated protein kinase cascade in peroxynitrite-mediated arachidonic acid release in vascular smooth muscle cells. Am J Physiol Cell Physiol 286 (2004) C1271-C1280
51. Perez-Sala D., and Lamas S. Regulation of cyclooxygenase-2 expression by nitric oxide in cells. Antioxid Redox Signal 3 (2001) 231-248
52. Huie R.E., and Padmaja S. The reaction of NO with superoxide. Free Radic Res Commun 18 (1993) 195-199
53. Oemar B.S., Tschudi M.R., Godoy N., Brovkovich V., Malinski T., and Luscher T.F. Reduced endothelial nitric oxide synthase expression and production in human atherosclerosis. Circulation 97 (1998) 2494-2498
54. Ohara Y., Peterson T.E., and Harrison D.G. Hypercholesterolemia increases endothelial superoxide anion production. J Clin Invest 91 (1993) 2546-2551
55. Beckman J.S., and Crow J.P. Pathological implications of nitric oxide, superoxide and peroxynitrite formation. Biochem Soc Trans 21 (1993) 330-334
56. Boulos C., Jiang H., and Balazy M. Diffusion of peroxynitrite into the human platelet inhibits cyclooxygenase via nitration of tyrosine residues. J Pharm Exp Ther 293 (2000) 222-229
57. Schildknecht S., Bachschmid M., and Ullrich V. Peroxynitrite provides the peroxide tone for PGHS-2-dependent prostacyclin synthesis in vascular smooth muscle cells. Faseb J, FJ Express 19 (2005) 1169-1171
58. Bachschmid M., Schildknecht S., and Ullrich V. Redox regulation of vascular prostanoid synthesis by the nitric oxide-superoxide system. Biochem Biophys Res Commun 338 (2005) 536-542
59. Floris R., Piersma S.R., Yang G., Jones P., and Wever R. Interaction of myeloperoxidase with peroxynitrite. A comparison with lactoperoxidase, horseradish peroxidase and catalase. Eur J Biochem 215 (1993) 767-775 published erratum appears in Eur J Biochem 1993;216(3):881
60. Shimokawa T., Kulmacz R.J., De Witt D.L., and Smith W.L. Tyrosine 385 of prostaglandin endoperoxide synthase is required for cyclooxygenase catalysis. J Biol Chem 265 (1990) 20073-20076
61. Hsi L.C., Hoganson C.W., Babcock G.T., Garavito R.M., and Smith W.L. An examination of the source of the tyrosyl radical in ovine prostaglandin endoperoxide synthase-1. Biochem Biophys Res Commun 207 (1995) 652-660
62. Tsai A., Hsi L.C., Kulmacz R.J., Palmer G., and Smith W.L. Characterization of the tyrosyl radicals in ovine prostaglandin H synthase-1 by isotope replacement and site-directed mutagenesis. J Biol Chem 269 (1994) 5085-5091
63. Shi W., Hoganson C.W., Espe M., et al. Electron paramagnetic resonance and electron nuclear double resonance spectroscopic identification and characterization of the tyrosyl radicals in prostaglandin H synthase 1. Biochemistry 39 (2000) 4112-4121
64. Rogge C., Liu W., Wu G., Wang L., Kulmacz R., and Tsai A. Identification of Tyr504 as an alternative tyrosyl radical site in human prostaglandin H synthase-2. Biochemistry 43 (2004) 1560-1568
65. 2 synthase. J Lipid Res 43 (2002) 1718-1726
66. Kulmacz R.J., Ren Y., Tsai A.L., Palmer G., and Prostaglandin. H synthase: spectroscopic studies of the interaction with hydroperoxides and with indomethacin. Biochemistry 29 (1990) 8760-8771
67. Gunther M.R., Hsi L.C., Curtis J.F., et al. Nitric oxide trapping of the tyrosyl radical of prostaglandin H synthase-2 leads to tyrosine iminoxyl radical and nitrotyrosine formation. J Biol Chem 272 (1997) 17086-17090
68. Kim Y.M., Bergonia H.A., Muller C., Pitt B.R., Watkins W.D., and Lancaster Jr. J.R. Loss and degradation of enzyme-bound heme induced by cellular nitric oxide synthesis. J Biol Chem 270 (1995) 5710-5713
69. O'Donnell V.B., Chumley P.H., Hogg N., Bloodsworth A., Darley-Usmar V.M., and Freeman B.A. Nitric oxide inhibition of lipid peroxidation: kinetics of reaction with lipid peroxyl radicals and comparison with alpha-tocopherol. Biochemistry 36 (1997) 15216-15223
70. Ischiropoulos H. Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch Biochem Biophys 356 (1998) 1-11
71. Ischiropoulos H. Biological selectivity and functional aspects of protein tyrosine nitration. Biochem Biophys Res Commun 305 (2003) 776-783
72. Beckmann J.S., Ye Y.Z., Anderson P.G., et al. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol Chem Hoppe Seyler 375 (1994) 81-88
73. Leeuwenburgh C., Hardy M.M., Hazen S.L., et al. Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima. J Biol Chem 272 (1997) 1433-1436
74. Pratico D., Tillmann C., Zhang Z.B., Li H., and FitzGerald G.A. Acceleration of atherogenesis by COX-1-dependent prostanoid formation in low density lipoprotein receptor knockout mice. Proc Natl Acad Sci USA 98 (2001) 3358-3363
75. Kuhlencordt P.J., Chen J., Han F., Astern J., and Huang P.L. Genetic deficiency of inducible nitric oxide synthase reduces atherosclerosis and lowers plasma lipid peroxides in apolipoprotein E-knockout mice. Circulation 103 (2001) 3099-3104
76. Berry C., Hamilton C.A., Brosnan M.J., et al. Investigation into the sources of superoxide in human blood vessels: angiotensin II increases superoxide production in human internal mammary arteries. Circulation 101 (2000) 2206-2212
77. Xia Y., and Zweier J.L. Superoxide and peroxynitrite generation from inducible nitric oxide synthase in macrophages. Proc Natl Acad Sci USA 94 (1997) 6954-6958
78. Beckman J. Oxidative damage and tyrosine nitration from peroxynitrite. Chem Res Toxicol 9 (1996) 836-844
79. 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
80. Radi R., Beckman J.S., Bush K.M., and Freeman B.A. Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. J Biol Chem 266 (1991) 4244-4250
81. Lymar S., Jiang Q., and Hurst J. Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35 (1996) 7855-7861
82. Burner U., Furtmuller P., Kettle A., Koppenol W., and Obinger C. Mechanism of reaction of myeloperoxidase with nitrite. J Biol Chem 275 (2000) 20597-20601
83. Gebicka L. Kinetic studies on the oxidation of nitrite by horseradish peroxidase and lactoperoxidase. Acta Biochim Pol 46 (1999) 919-927
84. van der Vliet A., Eiserich J.P., Halliwell B., and Cross C.E. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity. J Biol Chem 272 (1997) 7617-7625
85. Hazell L.J., Baernthaler G., and Stocker R. Correlation between intima-to-media ratio, apolipoprotein B-100, myeloperoxidase, and hypochlorite-oxidized proteins in human atherosclerosis. Free Radic Biol Med 31 (2001) 1254-1262
86. Brennan M.L., and Hazen S.L. Emerging role of myeloperoxidase and oxidant stress markers in cardiovascular risk assessment. Curr Opin Lipidol 14 (2003) 353-359
87. Sampson J.B., Ye Y., Rosen H., and Beckman J.S. Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch Biochem Biophys 356 (1998) 207-213
88. Podrez E.A., Schmitt D., Hoff H.F., and Hazen S.L. Myeloperoxidase-generated reactive nitrogen species convert LDL into an atherogenic form in vitro. J Clin Invest 103 (1999) 1547-1560
89. Nicolis S., Monzani E., Roncone R., Gianelli L., and Casella L. Metmyoglobin-catalyzed exogenous and endogenous tyrosine nitration by nitrite and hydrogen peroxide. Chemistry 10 (2004) 2281-2290
90. Schildknecht S., Heinz K., Daiber A., et al. Autocatalytic tyrosine nitration of prostaglandin endoperoxide synthase-2 in LPS-stimulated RAW 264.7 macrophages. Biochem Biophys Res Commun 340 (2005) 318-325
91. 2 synthase-1 by peroxynitrite. J Lipid Res 47 (2006) 898-911
92. Smith C.D., Carson M., Vanderwoerd M., Chen J., Ischiropoulos H., and Beckman J.S. Crystal-structure of peroxynitrite-modified bovine Cu, Zn superoxide-dismutase. Arch Biochem Biophys 299 (1992) 350-355
93. Daiber A., Bachschmid M., Beckman J.S., Munzel T., and Ullrich V. The impact of metal catalysis on protein tyrosine nitration by peroxynitrite. Biochem Biophys Res Commun 317 (2004) 873-881
94. Zou M.H., Leist M., and Ullrich V. Selective nitration of prostacyclin synthase and defective vasorelaxation in atherosclerotic bovine coronary arteries. Am J Pathol 154 (1999) 1359-1365
95. Stamler J.S., Jaraki O., Osborne J., et al. Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin. Proc Natl Acad Sci USA 89 (1992) 7674-7677
96. Jia L., Bonaventura C., Bonaventura J., and Stamler J.S. S-Nitrosohaemoglobin: a dynamic activity of blood involved in vascular control. Nature 380 (1996) 221-226
97. Kennedy T.A., Smith C.J., and Marnett L.J. Investigation of the role of cysteines in catalysis by prostaglandin endoperoxide synthase. J Biol Chem 269 (1994) 27357-27364
98. Saville B. A scheme for the colorimetric determination of microgram amounts of thiols. Analyst 83 (1958) 670-672
99. Ignarro L.J., Lippton H., Edwards J.C., et al. Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: evidence for the involvement of S-nitrosothiols as active intermediates. J Pharmacol Exp Ther 218 (1981) 739-749
100. Upmacis R.K., Hajjar D.P., Chait B.T., and Mirza U.A. Direct observation of nitrosylated heme in myoglobin and hemoglobin by electrospray ionization mass spectrometry. J Am Chem Soc 119 (1997) 10424-10429
101. Goodwin D.C., Landino L.M., and Marnett L.J. Effects of nitric oxide and nitric oxide-derived species on prostaglandin endoperoxide synthase and prostaglandin biosynthesis. FASEB J 13 (1999) 1121-1136
102. Jaffrey S.R., and Snyder S.H. The biotin switch method for the detection of S-nitrosylated proteins. Sci STKE 2001 (2001) PL1
103. Hao G., Derakhshan B., Shi L., Campagne F., and Gross S. SNOSID, a proteomic method for identification of cysteine S-nitrosylation sites in complex protein mixtures. Proc Natl Acad Sci USA 103 (2006) 1012-1017
104. 2. J Biol Chem 272 (1997) 16709-16712
105. 2). FEBS Lett 410 (1997) 49-53
106. 2 is phosphorylated and activated by MAP kinase. Cell 72 (1993) 269-278
107. 2 by p42 microtubule-associated protein 2 kinase and protein kinase C. J Biol Chem 268 (1993) 1960-1964
108. 2 are abrogated by an inhibitor of the p38 mitogen-activated protein kinase cascade in human neutrophils. Biochem J 319 (1996) 17-20
109. Jope R.S., Zhang L., and Song L. Peroxynitrite modulates the activation of p38 and extracellular regulated kinases in PC12 cells. Arch Biochem Biophys 376 (2000) 365-370
110. Takakura K., Beckman J.S., MacMillan-Crow L.A., and Crow J.P. Rapid and irreversible inactivation of protein tyrosine phosphatases PTP1B, CD45, and LAR by peroxynitrite. Arch Biochem Biophys 369 (1999) 197-207