Reactive nitrogen species and tyrosine nitration in the respiratory tract: Epiphenomena or a pathobiologic mechanism of disease?

American Journal of Respiratory and Critical Care Medicine

Volumn 160, Issue 1, 1999, Pages 1-9

  Van Der Vliet, Albert ^a   Eiserich, Jason P ^b   Shigenaga, Mark K ^b   Cross, Carroll E ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3 NITROTYROSINE; NITRIC OXIDE; NITROGEN DERIVATIVE; REACTIVE NITROGEN SPECIES; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; DISEASE ASSOCIATION; DISEASE MARKER; HUMAN; LUNG DISEASE; NITRATION; OXIDATION; PATHOGENESIS; PRIORITY JOURNAL; RESPIRATORY SYSTEM; REVIEW;

EID: 0032794510     PISSN: 1073449X     EISSN: None     Source Type: Journal    
DOI: 10.1164/ajrccm.160.1.9807044     Document Type: Review

References (78)

1. Moncada, S., R. M. J. Palmer, and E. A. Higgs. 1991. Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev. 43:109-142.
2. Gaston, B., J. M. Drazen, J. Loscalzo, and J. S. Stamler. 1994. The biology of nitrogen oxides in the airways. Am. J. Respir. Crit. Care Med 149:538-551.
3. Fang, F. C. 1997. Mechanisms of nitric oxide-related antimicrobial activity. J. Clin. Invest. 100:S43-S50.
4. Beckman, J. S., and W. H. Koppenol. 1996. Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and the ugly. Am. J. Physiol. 271: C1424-C1437.
5. Beckman, J. S. 1996. Oxidative damage and tyrosine nitration from peroxynitrite. Chem. Res. Toxicol. 9:836-844.
6. Ischiropoulos, H. 1998. Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356:1-11.
7. Nathan, C. 1997. Inducible nitric oxide synthase: what difference does it make? J. Clin. Invest. 100:2417-2423.
8. Rubbo, H., V. Darley-Usmar, and B. A. Freeman. 1996. Nitric oxide regulation of tissue free radical injury. Chem. Res. Toxicol 9:809-820.
9. Kroncke, K.-D., K. Fehsel, and V. Kolb-Bachofen. 1997. Nitric oxide: cytotoxicity versus cyloprotcction - how, why, when, and where? Nitric Oxide: Biol. Chem. 1:107-120.
10. Bigetello, L. M., W. E. Hurfold, and D. Hess. 1998. Use of inhaled nitric oxide for ARDS. Respir. Care. Clin. North Am. 3:437-458.
11. Stamler, J. S., D. J. Singel, and J. Loscalzo. 1992. Biochemistry of nitric oxide and its redox activated forms. Science 258:1898-1902.
12. Parks, N. J., K. A. Krohn, C. A. Mathis, J. H. Chasko, K. R. Geiger, M. E. Gregor, and N. F. Peek. 1981. Nitrogen-13-labeled nitrite and nitrate: distribution and metabolism after intratracheal administration. Science 212:58-61.
13. Pryor, W. A., and G. L. Squadrilo. 1995. The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. Am. J. Physiol 268:L699-L722.
14. Tamir, S., S. Burney, and S. R. Tannenbaum. 1996. DNA damage by nitric oxide. Chem. Res. Toxicol. 9:821-827.
15. Haddad, L. Y., G. Pataki, P. Hu, C. Galliani, J. S. Beckman, and S. Matalon. 1994. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J. Clin. Invest. 94:2407-2413.
16. Beckman, J. S., Y. Z. Ye, P. Anderson, J. Chen, M. A. Accavetti, M. M. Tarpey, and C. R. White. 1994. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Boil. Chem. Hoppe Seyler 375:81-88.
17. Khan, J., D. M. Brennan, N. Bradley, B. Gao, R. Bruckdorfer, and M. Jacobs. 1998. 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochem. J. 330:795-801.
18. 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.
19. Eiserich, J. P., M. Hristova, C. E. Cross, A. D. Jones, B. A. Freeman, B. Halliwell, and A. van der Vliet. 1998. Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391:393-397.
20. van der Vliet, A., J. P. Eiserich, H. Kaur, C. E. Cross, and B. Halliwell. 1996. Nitrotyrosine as a biomarker for reactive nitrogen species. Methods Enzymol. 269:175-184.
21. Hensley, K., M. L. Maidt, Q. N. Pye, C. A. Stewart, M. Wack, T. Tahatabiae, and R. A. Floyd. 1997. Quantitation of protein-bound 3-nitrotyrosine and 3,4-dihydroxyphenylalanine by high-performance liquid chromatography with electrochemical array detection. Anal. Biochem. 251:187-195.
22. Kamisaki, Y., K. Wada, K. Nakamoto, Y. Kishimoto, M. Kitano and T. Itoh. 1996. Sensitive determination of nitrotyrosine in human plasma by isocratic high-performance liquid chromatography. J. Chromatogr. Biomed. Appl. 685:343-347.
23. x-induced nitration: assay for 3-nitrotyrosine by HPLC with electrochemical detection. Proc. Natl. Acad. Sci. U.S.A. 94:3211-3216.
24. Ohshima, H., M. Friesen, I. Brouet, and H. Bartsch. 1990. Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem. Toxicol. 28:647-652.
25. Leeuwenburgh, C., M. M. Hardy. S. L. Hazen, P. Wagner, S. Oh-ishi, 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.
26. Crowley, J. R., K. Yarasheski, C. Leeuwenburgh, J. Turk, and J. W. Heinecke. 1998. Isotope dilution mass spectrometric quantification of 3-nitrotyrosine in proteins and tissues is facilitated by reduction to 3-aminotyrosine. Anal. Biochem. 259:127-135.
27. Greis, K. D., S. Zhu, and S. Matalon. 1996. Identification of nitration sites on surfactant protein A by tandem electrospray mass spectrometry. Arch. Biochem Biophys. 335:396-402.
28. Yi, D., G. A. Smythe, B. C. Blount, and M. W. Duncan. 1997. Peroxrnitrite-mediated nitration of peptides: characterization of the products by electrospray and combined gas chromatography-mass spectrometry. Arch. Biochem. Biophys. 344:253-259.
29. Wizeman, T. M., C. R. Gardner, J. D. Laskin, S. Quinones, S. K. Durham, N. L. Goller, S. T. Ohnishi, and D. L. Laskin. 1994. Production of nitric oxide and peroxynitrite in the lung during acute endotoxemia. J. Leukoc. Biol. 56:759-768.
30. Numata, M., S. Suzuki. N. Miyazawa, A. Miyashita, Y. Nagashima, S. Inoue, T, Kaneko, and T. Okubo. 1998. Inhibition of inducible nitric oxide synthase prevents LPS-induced acute lung injury in dogs. J. Immunol. 160:3031-3037.
31. Ischiropoulos, H., A. B. Al-Mehdi, and A. B. Fisher. 1995. Reactive species in ischemic rat lung injury: contribution of peroxynitrite. Am. J. Physiol. 269:L158-L164.
32. Akaike, T., Y. Noguchi, S. Ijiri, K. Setoguch, M. Suga, Y. M. Zheng, B. Dietzschold, and H. Maeda. 1996. Pathogenesis of influenza virus-induced pneumonia: involvement of both nitric oxide and oxygen radicals. Proc. Natl. Acad. Sci. U.S.A. 93:2448-2453.
33. Tanaka, S., N. Choe, D. R. Hemenway, S. Zhu, S. Matalon, and F. Kagan. 1998. Asbestos inhalation induces reactive nitrogen species and nitrotyrosine formation in the lungs and pleura or the rat. J. Clin. Invest. 102:445-454.
34. Kooy, N. W., J. A. Royall Y. Z. Ye, D. R. Kelly, and J. S. Beckman. 1995. Evidence for in vivo peroxynitrile production in human acute lung injury. Am. J. Respir. Crit. Care. Med. 151:1250-1254.
35. Salch, D., P. J. Barnes, and A. Giaid. 1997. Increased production of the potent oxidant peroxynitrite in the lungs of patients with idopathic pulmonary fibrosis. Am. J. Respir. Crit. Care Med. 155:1763-1769.
36. McDermott, C. D., S. M. Gavita, H. Shennib, and A. Giaid, 1997. Immunohistochemical localization of nitric oxide synthase and the oxidant peroxynitrite in lung transplant recipients with obliterative bronchiolitis. Transplantation 64:270-274.
37. van der Vliet, A., J. P. Eiserich, G. P. Marelich, B. Halliwell, and C. E. Cross. 1997. Oxidative stress in cystic fibrosis: does it occur and does it matter? Adv. Pharmacol. 38:491-513.
38. Kaminsky, D. A., and Y. M. W. Janssen. 1998. Evidence for peroxynitrite formation in severe human asthma (abstract). Am. J. Respir. Crit. Care. Med. 157:A876.
39. Saleh, D., P. Ernst, S. Lim, P. J. Barnes, and A. Giaid. 1998. Increased formation of the potent oxidant peroxynitrite in the airways of asthmatic patients is associated with induction of nitric oxide synthase: effect of inhaled glucocorticoid. FASEB J. 12:929-937.
40. Sato, M., N. Fukuyama, M. Sakai, and H. Nakazawa. 1998. Increased nitric oxide in nasal lavage fluid and nitrotyrosine formation in nasal mucosa - indices for severe perennial nasal allergy. Clin. Exp. Allergy 28:597-605.
41. Olah, G. A., R. Malhotra, and S. C. Narang. 1989. Nitration: Methods and Mechanisms. VCH Publishers, New York.
42. Peluso, A., and G. Del Re. 1996. On the occurrence of an electron-trans fer step in aromatic nitration. J. Phys. Chem. 100:5303-5309.
43. Lymar, S. V., and J. K. Hurst. 1996. Carbon dioxide: physiological catalyst for peroxynitrite-mediated cellular damage or cellular protectant. Chem. Res. Toxicol. 9:845-850.
44. van der Vliet, A., J. P. Eiserich, C. A. O'Neill, B. Halliwell, and C. E. Cross. 1995. Tyrosine modification by reactive nitrogen species: a closer look. Arch. Biochem. Biophys. 319:341-349.
45. Pietraforte, D., and M. Minetti. 1997. Direct ESR detection of peroxynitrite-induced tyrosine-centred protein radicals in human blood plasma. Biochem. J. 325:675-684.
46. Floris, R., S. R. Piersma, G. Yang, P. Jones, and R. Wever. 1993. Interaction of myeloperoxidase with peroxynitrite: a comparison with lactoperoxidase, horseradish peroxidase and catalase. Eur. J. Biochem. 215:767-775.
47. Salvemini, D., Z.-Q. Wang, M. K. Stern, M. G. Currie, and T. P. Misko. 1998. Peroxynitrite decomposition catalysts: therapeutics for peroxynitrite-mediated pathology. Proc. Natl. Acad. Sci. U.S.A. 95:2659-2663.
48. 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.
49. Zhou, M. C. Martin, and V. Ullrich. 1997. Tyrosine nitration as a mechanism of selective inactivation of prostacyclin synthase by peroxynitrite. Biol. Chem. 378:707-713.
50. Stubbe, J., and W. A. van der Donk. 1998. Protein radicals in enzyme catalysis. Chem. Rev. 98:705-762.
51. Ortiz de Montellano, P. R. 1992. Catalytic sites of hemoprotein peroxidases. Annu. Rev. Pharmacol. Toxicol. 32:89-107.
52. Heinecke, J. W. 1997. Mechanisms of oxidative damage of low density lipoprotein in human atherosclerosis. Curr. Opin. Lipidol. 8:268-274.
53. Eiserich, J. P., C. E. Cross, A. D. Jones, B. Halliwell, and A. van der Vliet. 1996. Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid: a novel mechanism for nitric oxide-dependent protein modification. J. Biol. Chem. 271:19199-19208.
54. Pfeiffer, S., and B. Mayer. 1998. Lack of tyrosine nitration by peroxynitrite generated at physiological pH. J. Biol. Chem. 273:27280-27285.
55. Basagra, O., F. H. Michaels, Y. M. Zheng, L. E. Bobroski, S. V. Spitsin, Z. F. Fu, R. Tawadros, and H. Koprowski. 1995. Activation of the inducible form of nitric oxide synthase in the brains of patients with multiple sclerosis. Proc. Natl. Acad. Sci. U.S.A. 92:12041-12045.
56. Nagra, R. M., B. Becher, W. W. Tourtellotte, J. P. Antel, D. Gold, T. Paladino, R. A. Smith, J. R. Nelson, and W. F. Reynolds. 1997. Immunohistochemical and genetic evidence of myeloperoxidase involvement in multiple sclerosis. J. Neuroimmunol. 78:97-107.
57. Shin, J. T., L. Barbeito, L. A. Mac-Millan-Crow, J. S. Beckman, and J. A. Thompson. 1996. Acidic fibroblast growth factor enhances peroxynitrite-induced apoptosis in primary murine fibroblasts. Arch. Biochem. Biophys. 335:32-41.
58. Estévez, A. G., N. Spear, S. M. Manuel, R. Radi, C. F. Henderson L. Barbeito, and J. S. Beckman. 1998. Nitric oxide and superoxide contribute to motor neuron apoptosis induced by trophic factor deprivation. J. Neurosci. 18:923-931.
59. Janssen, Y. M. W., S. Matalon, and B. T. Mossman. 1997. Differential induction of c-fos, c-jun, and apoptosis in lung epithelial cells exposed to ROS or RNS. Am. J. Physiol. 273:L789-L796.
60. Yermilov, V., J. Rubio, and H. Ohshima. 1995. Formation of 8-nitroguanine in DNA treated with peroxynitrile in vitro and its rapid removal from DNA by depurination. FEBS Lett. 376:207-210.
61. Juedes, M. J., and G. N. Wogan. 1996. Peruxynitrite-induced mutation spectra of pSPI89 following replication in bacteria and in human cells. Mutation Res. 349:51-61.
62. Kong, S.-K., M. B. Yim, E. R. Stadman, and P. B. Chock. 1996. Peroxynitrite disables the tyrosine phosphorylation regulatory mechanism: lymphocyte-specific tyrosine kinase fails to phosphorylate nitrated cdc2(6-20)NH2 peptide. Proc. Natl. Acad. Sci. U.S.A. 93:3377-3382.
63. Gow, A. J., D. Duran, S. Malcolm, and H. Ischiropoulos. 1996. Effects of peroxynitrite-induced protein modifications on tyrosine phosphorylation and degradation. FEBS Lett. 385:63-66.
64. Li, X., P. De Sarno, L. Song, J. S. Beckman, and R. S. Jope. 1998. Peroxynitrite modulates tyrosine phosphorylation and phosphoinositide signalling in human neuroblasmma SH-SY5Y cells: attenuated effects in human 1321N1 astrocytoma cells. Biochem. J. 331:599-606.
65. Mallozzi, C., A. M. M. Di Stasi, and M. Minetti. 1997. Peroxynitrite modulates tyrosine-dependent signal transduction pathway of human erythrocyte band 3. FASEB J. 11:1281-4290.
66. van der Vliet, A. M. Hristova, C. E. Cross, J. P. Eiserich, and T. Goldkorn. 1998. Peroxynitrite induces covalent dimerization of epidermal growth factor receptors in A431 epidermoid carcinoma cells. J. Biol. Chem. 273:3186-31866.
67. Berlett, B. S., R. L. Levine, and E. R. Stadtman. 1998. Carbon dioxide stimulates peroxynitrite-mediated nitration of tyrosine residues and inhibits oxidation of methionine residues of glutamate synthase: both modifications mimic effects of adenylation. Proc. Natl. Acad. Sci. U.S.A 95:2784-2789.
68. Landino, L. M., B. C. Vrews, M. D. Timmons, J. D. Morrow, and L. J. Marnett. 1996. Peroxynitrite, the coupling product of nitric oxide and superoxide, activates prostaglandin synthesis. Proc. Natl. Acad. Sci. U.S.A. 93:15069-15074.
69. Boota, A., H. Zar, Y.-M. Kim, B. Johnson, B. Pitt, and P. Davies. 1997. IL-1β stimulates superoxide and delayed peroxynitrite production by pulmonary vascular smooth muscle cells. Am. J. Physiol. 271:L932-L938.
70. Kooy, N. W., S. J. Lewis, J. A. Royall, Y. Z. Ye, D. R. Kelly, and J. S. Beckman. 1997. Extensive tyrosine nitration in human myocardial inflammation: evidence for the presence of peroxynitrite. Crit. Care Med. 25:812-819.
71. Eiserich, J. P., A. G. Estévez, T. Bamberg, Y. Z. Ye, P. H. Chumley, J. S. Beckman, and B. A. Freeman. 1998. Microtubule dysfunction by posttranslational nitrotyrosination of α-tubulin: a nitric oxide-dependent mechanism of cellular injury. Proc. Natl. Acad. Sci. U.S.A. 96:6365-6370.
72. Zhu, S., I. Y, Haddad, and S. Matalon. 1996. Nitration of surfactant protein A (SP-A) tyrosine residues results in decreased mannose binding ability. Arch. Biochem. Biophys. 333:282-290.
73. Haddad, I. Y., S. Zhou, H. Ischiropoulos, and S. Matalon. 1996. Nitration of surfactant protein A results in decreased ability to aggregate lipids. Am, J. Physiol. 270:L281-L288.
74. Evans, T. J., L. D. Buttery, A. Carpenter, D. R. Springall, J. M. Polak, and J. Cohen. 1996. Cytokine-treated human neutrophils contain inducible nitric oxide synthase that produces nitration of ingested bacteria. Proc. Natl. Acad. Sci. U.S.A. 93:9553-9558.
75. Klebanoff, S. J. 1993. Reactive nitrogen intermediates and antimocrobial activity: role of nitrite. Free Radic. Biol. Med. 14:351-360.
76. Jiang, O., and J. K. Hurst. 1997. Relative chlorinating, nitrating, and oxidizing capabilities of neutrophils determined with phagocytosable probes. J. Biol. Chem. 272:32767-32772.
77. Salathe, M., M. Holderby, R. Forteza, W. M. Abraham, A. Wanner, and G. E. Conner. 1997. Isolation and characterizaton of a peroxidase from the airway. Am. J. Respir. Cell Mol. Biol. 17:97-105.
78. Kamisaki, Y., K. Wada, K. Bian, B. Balabanli, K. Davis, E. Martin, F. Behbod, Y.-C. Lee. and F. Murad. 1998. An activity in rat tissues that modifies nitrotyrosine-containing proteins. Proc. Natl. Acad. Sci. U.S.A. 95:11584-11589.