Tyrosine nitration in prostaglandin H2 synthase

Journal of Lipid Research

Volumn 43, Issue 10, 2002, Pages 1718-1726

  Deeb, Ruba S ^a   Resnick, Matthew J ^a   Mittar, Dev ^a   McCaffrey, Timothy ^a   Hajjar, David P ^a   Upmacis, Rita K ^a  

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

Author keywords

Atherosclerosis; Cyclooxygenase; Peroxynitrite

Indexed keywords

NITROGEN DIOXIDE; NITROGEN OXIDE; PEROXYNITRITE; PROSTAGLANDIN SYNTHASE; TETRANITROMETHANE; TRIAZENE DERIVATIVE; TYROSINE;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; ATHEROGENESIS; ATHEROSCLEROSIS; CAROTID ARTERY DISEASE; CAROTID ENDARTERECTOMY; CONTROLLED STUDY; ENZYME ACTIVITY; HUMAN; HUMAN TISSUE; MASS SPECTROMETRY; NONHUMAN; PATHOGENESIS; PRIORITY JOURNAL; RAT; SEMINAL VESICLE; ULTRAVIOLET SPECTROSCOPY; VASCULAR SMOOTH MUSCLE;

ANIMALS; AORTA, THORACIC; BLOTTING, WESTERN; CULTURE TECHNIQUES; ENDARTERECTOMY, CAROTID; HUMANS; MALE; MUSCLE, SMOOTH, VASCULAR; NITRIC OXIDE DONORS; NITROGEN OXIDES; PRECIPITIN TESTS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RATS; SEMINAL VESICLES; SHEEP; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY; TYROSINE;

EID: 0036795635     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M200199-JLR200     Document Type: Article

References (53)

1. Huie, R. E., and S. Padmaja. 1993. The reaction of no with superoxide. Free Radic. Res. Commun. 18: 195-199.
2. Radi, R., J. S. Beckman, K. M. Bush, and B. A. Freeman. 1991. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288: 481-487.
3. Radi, R., J. S. Beckman, K. M. Bush, and B. A. Freeman. 1991. Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. J. Biol. Chem. 266: 4244-4250.
4. Ischiropoulos, H., and A. B. al-Mehdi. 1995. Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 364: 279-282.
5. Matheis, G., M. P. Sherman, G. D. Buckberg, D. M. Haybron, H. H. Young, and L. J. Ignarro. 1992. Role of L-arginine-nitric oxide pathway in myocardial reoxygenation injury. Am. J. Physiol. 262: H616-H620.
6. Upmacis, R. K., R. S. Deeb, and D. P. Hajjar. 1999. Regulation of prostaglandin H2 synthase activity by nitrogen oxides. Biochemistry. 38: 12505-12513.
7. Oshima, M., J. E. Dinchuk, S. L. Kargman, H. Oshima, B. Hancock, E. Kwong, J. M. Trzaskos, J. F. Evans, and M. M. Taketo. 1996. Suppression of intestinal polyposis in Apc delta716 knockout mice by inhibition of cyclooxygenase 2 (COX-2). Cell. 87: 803-809.
8. Baker, C. S., R. J. Hall, T. J. Evans, A. Pomerance, J. Maclouf, C. Creminon, M. H. Yacoub, and J. M. Polak. 1999. 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: 646-655.
9. Schonbeck, U., G. K. Sukhova, P. Graber, S. Coulter, and P. Libby. 1999. Augmented expression of cyclooxygenase-2 in human atherosclerotic lesions. Am. J. Pathol. 155: 1281-1291.
10. Moncada, S., and J. Vane. 1978. Unstable metabolites of arachidonic acid and their role in haemostasis and thrombosis. Br. Med. Bull. 34: 129-135.
11. Libby, P., S. J. Warner, and G. B. Friedman. 1988. Interleukin 1: a mitogen for human vascular smooth muscle cells that induces the release of growth-inhibitory prostanoids. J. Clin. Invest. 81: 487-498.
12. Salvemini, D., T. P. Misko, J. L. Masferrer, K. Seibert, M. G. Currie, and P. Needleman. 1993. Nitric oxide activates cyclooxygenase enzymes. Proc. Natl. Acad. Sci. USA. 90: 7240-7244.
13. Landino, L. M., B. C. Crews, M. D. Timmons, J. D. Morrow, and L. J. Marnett. 1996. Peroxynitrite, the coupling product of nitric oxide and superoxide, activates prostaglandin biosynthesis. Proc. Natl. Acad. Sci. USA. 93: 15069-15074.
14. Kanner, J., S. Harel, and R. Granit. 1992. Nitric oxide, an inhibitor of lipid oxidation by lipoxygenase, cyclooxygenase and hemoglobin. Lipids. 27: 46-49.
15. Tsai, A. L., C. Wei, and R. J. Kulmacz. 1994. Interaction between nitric oxide and prostaglandin H synthase. Arch. Biochem. Biophys. 313: 367-372.
16. Curtis, J. F., N. G. Reddy, R. P. Mason, B. Kalyanaraman, and T. E. Eling. 1996. 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: 369-376.
17. Stamler, J. S., D. J. Singel, and J. Loscalzo. 1992. Biochemistry of nitric oxide and its redox-activated forms. Science. 258: 1898-1902.
18. Boulos, C., H. Jiang, and M. Balazy. 2000. Diffusion of Peroxynitrite into the Human Platelet Inhibits Cyclooxygenase via Nitration of Tyrosine Residues. J. Pharmacol. Exp. Ther. 293: 222-229.
19. Dietz, R., W. Nastainczyk, and H. H. Ruf. 1988. Higher oxidation states of prostaglandin H synthase. Rapid electronic spectroscopy detected two spectral intermediates during the peroxidase reaction with prostaglandin G2. Eur. J. Biochem. 171: 321-328.
20. Lee, J., J. A. Hunt, and J. T. Groves. 1998. Mechanisms of Iron Porphyrin Reactions with Peroxynitrite. J. Am. Chem. Soc. 120: 7493-7501.
21. Beckmann, J. S., Y. Z. Ye, P. G. Anderson, J. Chen, M. A. Accavitti, M. M. Tarpey, and C. R. White. 1994. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe Seyler. 375: 81-88.
22. Leeuwenburgh, C., M. M. Hardy, S. L. Hazen, P. Wagner, S. Ohishi, U. P. Steinbrecher, and J. W. Heinecke. 1997. Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima. J. Biol. Chem. 272: 1433-1436.
23. Mevkh, A. T., G. F. Sud'ina, N. B. Golub, and S. D. Varfolomeev. 1985. Purification of prostaglandin H synthetase and a fluorometric assay for its activity. Anal. Biochem. 150: 91-96.
24. Kulmacz, R. J., and W. E. M. Lands. 1987. Prostaglandins and Related Substances: A Practical Approach. IRL Press, Washington, D.C.
25. Roepstorff, P., and J. Fohlmam. 1984. Biomed. Mass Spectrom. 11: 601.
26. Hughes, M. N., and H. G. Nicklin. 1968. The Chemistry of Pernitrites. Part I. Kinetics of Decomposition of Pernitrous Acid. J. Chem. Soc. (A): 450-452.
27. Sokolovsky, M., J. F. Riordan, and B. L. Vallee. 1966. Tetranitromethane. A reagent for the nitration of tyrosyl residues in proteins. Biochemistry. 5: p3582-p3589.
28. Markwell, M. A., S. M. Haas, L. L. Bieber, and N. E. Tolbert. 1978. A modification of the Lowry procedure to simplify protein determination in membrane and lipoprotein samples. Anal. Biochem. 87: p206-p210.
29. Hrabie, J. A., J. R. Klose, D. A. Wink, and L. K. Keefer. 1993. New Nitric Oxide-Releasing Zwitterions Derived from Polyamines. J. Org. Chem. 58: 1472-1476.
30. Prutz, W. A., H. Monig, J. Butler, and E. J. Land. 1985. Reactions of nitrogen dioxide in aqueous model systems: oxidation of tyrosine units in peptides and proteins. Arch. Biochem. Biophys. 243: p125-p134.
31. Rosenkranz, B., B. R. Winkelmann, and M. J. Parnham. 1996. Clinical pharmacokinetics of molsidomine. Clin. Pharmacokinet. 30: 372-384.
32. van der Vliet, A., J. P. Eiserich, H. Kaur, C. E. Cross, and B. Halliwell. 1996. Nitrotyrosine as biomarker for reactive nitrogen species. Methods Enzymol. 269: 175-184.
33. Wu, K. K. 1995. Inducible cyclooxygenase and nitric oxide synthase. Adv. Pharmacol. 33: 179-207.
34. Goodwin, D. C., M. R. Gunther, L. C. Hsi, B. C. Crews, T. E. Eling, R. P. Mason, and L. J. Marnett. 1998. Nitric oxide trapping of tyrosyl radicals generated during prostaglandin endoperoxide synthase turnover. Detection of the radical derivative of tyrosine 385. J. Biol. Chem. 273: 8903-8909.
35. Pfeiffer, S., A. Lass, K. Schmidt, and B. Mayer. 2001. Protein tyrosine nitration in cytokine-activated murine macrophages. Involvement of a peroxidase/nitrite pathway rather than peroxynitrite. J. Biol. Chem. 276: p34051-p34058.
36. Espey, M. G., S. Xavier, D. D. Thomas, K. M. Miranda, and D. A. Wink. 2002. Direct real-time evaluation of nitration with green fluorescent protein in solution and within human cells reveals the impact of nitrogen dioxide vs. peroxynitrite mechanisms. Proc. Natl. Acad. Sci. USA. 99: p3481-p3486.
37. Singh, R. J., N. Hogg, J. Joseph, E. Konorev, and B. Kalyanaraman. 1999. The peroxynitrite generator, SIN-1, becomes a nitric oxide donor in the presence of electron acceptors. Arch. Biochem. Biophys. 361: p331-p339.
38. Koppenol, W. H., and R. Kissner. 1998. Can O=NOOH undergo homolysis? Chem. Res. Toxicol. 11: p87-90.
39. Lymar, S. V., and J. K. Hurst. 1995. Rapid Reaction Between Peroxonitrite Ion and Carbon Dioxide: Implications for Biological Activity. J. Am. Chem. Soc. 117: 8867-8868.
40. Kulmacz, R. J., Y. Ren, A. L. Tsai, and G. Palmer. 1990. Prostaglandin H synthase: spectroscopic studies of the interaction with hydroperoxides and with indomethacin. Biochemistry. 29: p8760-p8771.
41. Tsai, A. L., G. Palmer, and R. J. Kulmacz. 1992. Prostaglandin H synthase. Kinetics of tyrosyl radical formation and of cyclooxygenase catalysis. J. Biol. Chem. 267: 17753-17759.
42. Hsi, L. C., C. W. Hoganson, G. T. Babcock, R. M. Garavito, and W. L. Smith. 1995. An examination of the source of the tyrosyl radical in ovine prostaglandin endoperoxide synthase-1. Biochem. Biophys. Res. Commun. 207: 652-660.
43. Torre, D., G. Ferrario, F. Speranza, A. Orani, G. P. Fiori, and C. Zeroli. 1996. Serum concentrations of nitrite in patients with HIV-1 infection. J. Clin. Pathol. 49: p574-p576.
44. Koppenol, W. H. 1998. The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radic. Biol. Med. 25: p385-p391.
45. Dartey-Usmar, V. M., N. Hogg, V. J. O'Leary, M. T. Wilson, and S. Moncada. 1992. The simultaneous generation of superoxide and nitric oxide can initiate lipid peroxidation in human low density lipoprotein. Free Radic. Res. Commun. 17: 9-20.
46. van der Vliet, A., J. P. Eiserich, B. Halliwell, and C. E. Cross. 1997. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity. J. Biol. Chem. 272: 7617-7625.
47. Domigan, N. M., T. S. Charlton, M. W. Duncan, C. C. Winterbourn, and A. J. Kettle. 1995. Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils. J. Biol. Chem. 270: 16542-16548.
48. Hazen, S. L., J. R. Crowley, D. M. Mueller, and J. W. Heinecke. 1997. Mass spectrometric quantification of 3-chlorotyrosine in human tissues with attomole sensitivity: a sensitive and specific marker for myeloperoxidase-catalyzed chlorination at sites of inflammation. Free Radic. Biol. Med. 23: 909-916.
49. Ohara, Y., T. E. Peterson, and D. G. Harrison. 1993. Hypercholesterolemia increases endothelial superoxide anion production. J. Clin. Invest. 91: 2546-2551.
50. Olken, N. M., and M. A. Marletta. 1993. NG-methyl-L-arginine functions as an alternate substrate and mechanism-based inhibitor of nitric oxide synthase. Biochemistry. 32: p9677-p9685.
51. Xia, Y., L. J. Roman, B. S. Masters, and J. L. Zweier. 1998. Inducible nitric-oxide synthase generates superoxide from the reductase domain. J. Biol. Chem. 273: p22635-p22639.
52. Xia, Y., and J. L. Zweier. 1997. Superoxide and peroxynitrite generation from inducible nitric oxide synthase in macrophages. Proc. Natl. Acad. Sci. USA. 94: p6954-p6958.
53. Zou, M. H., M. Leist, and V. Ullrich. 1999. Selective nitration of prostacyclin synthase and defective vasorelaxation in atherosclerotic bovine coronary arteries. Am. J. Pathol. 154: 1359-1365.