A review of approaches to the analysis of 3-nitrotyrosine

Amino Acids

Volumn 25, Issue 3-4, 2003, Pages 351-361

  Duncan, M W ^a,b  

^a UNIVERSITY OF COLORADO   (United States)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

3 Nitrotyrosine; Artifactual formation; Assay validation; Mass spectrometry; Trace analysis

Indexed keywords

3 NITROTYROSINE;

CHEMICAL ANALYSIS; ELECTROCHEMICAL ANALYSIS; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NITRATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REVIEW;

ANIMALS; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; ELECTROCHEMISTRY; HUMANS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; TYROSINE;

EID: 0346100517     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-003-0022-z     Document Type: Review

References (77)

1. Abe K, Pan LH, Watanabe M, Kato T, Itoyama Y (1995) Induction of nitrotyrosine-like immunoreactivity in the lower motor neuron of amyotrophic lateral sclerosis. Neurosci Lett 199: 152-154
2. Akizuki E, Akaike T, Okamoto S, Fujii S, Yamaguchi Y, Ogawa M, Maeda H (2000) Role of nitric oxide and superoxide in acute cardiac allograft rejection in rats. Proc Soc Exp Biol Med 225: 151-159
3. Albrecht EW, Stegeman CA, Tiebosch AT, Tegzess AM, van Goor H (2002) Expression of inducible and endothelial nitric oxide synthases, formation of peroxynitrite and reactive oxygen species in human chronic renal transplant failure. Am J Transplant 2: 448-453
4. Althaus JS, Schmidt KR, Fountain ST, Tseng MT, Carroll RT, Galatsis P, Hall ED (2000) LC-MS/MS detection of peroxynitrite-derived 3-nitrotyrosine in rat microvessels. Free Radic Biol Med 29: 1085-1095
5. Balint B, Kharitonov SA, Hanazawa T, Donnelly LE, Shah PL, Hodson ME, Barnes PJ (2001) Increased nitrotyrosine in exhaled breath condensate in cystic fibrosis. Eur Respir J 17: 1201-1207
6. Banks BA, Ischiropoulos H, McClelland M, Ballard PL, Ballard RA (1998) Plasma 3-nitrotyrosine is elevated in premature infants who develop bronchopulmonary dysplasia. Pediatrics 101: 870-874
7. Beal MF, Ferrante RJ, Browne SE, Matthews RT, Kowall NW, Brown RH Jr (1997) Increased 3-nitrotyrosine in both sporadic and familial amyotrophic lateral sclerosis. Ann Neurol 42: 644-654
8. Beckman JS, Ye YZ, Anderson PG, Chen J, Accavitti MA, Tarpey MM, White CR (1994) Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol Chem Hoppe Seyler 375: 81-88
9. Brennan ML, Wu W, Fu X, Shen Z, Song W, Frost H, Vadseth C, Narine L, Lenkiewicz E, Borchers MT, Lusis AJ, Lee JJ, Lee NA, Abu-Soud HM, Ischiropoulos H, Hazen SL (2002) A tale of two controversies: defining both the role of peroxidases in nitrotyrosine formation in vivo using eosinophil peroxidase and myeloperoxidase-deficient mice, and the nature of peroxidase-generated reactive nitrogen species. J Biol Chem 277: 17415-17427
10. Ceriello A, Mercuri F, Quagliaro L, Assaloni R, Motz E, Tonutti L, Taboga C (2001) Detection of nitrotyrosine in the diabetic plasma: evidence of oxidative stress. Diabetologia 44: 834-838
11. Cesselli D, Jakoniuk I, Barlucchi L, Beltrami AP, Hintze TH, Nadal-Ginard B, Kajstura J, Leri A, Anversa P (2001) Oxidative stress-mediated cardiac cell death is a major determinant of ventricular dysfunction and failure in dog dilated cardiomyopathy. Circ Res 89: 279-286
12. Cromheeke KM, Kockx MM, De Meyer GR, Bosmans JM, Bult H, Beelaerts WJ, Vrints CJ, Herman AG (1999) Inducible nitric oxide synthase colocalizes with signs of lipid oxidation/peroxidation in human atherosclerotic plaques. Cardiovasc Res 43: 744-754
13. Cross AH, Manning PT, Keeling RM, Schmidt RE, Misko TP (1998) Peroxynitrite formation within the central nervous system in active multiple sclerosis. J Neuroimmunol 88: 45-56
14. Crow JP (1999) Measurement and significance of free and protein-bound 3-nitrotyrosine, 3-chlorotyrosine, and free 3-nitro-4-hydroxyphenyl-acetic acid in biologic samples: a high-performance liquid chromatography method using electrochemical detection. Methods Enzymol 301: 151-160
15. Crow JP, Ischiropoulos H (1996) Detection and quantitation of nitrotyrosine residues in proteins: in vivo marker of peroxynitrite. Methods Enzymol 269: 185-194
16. Crowley JR, Yarasheski K, Leeuwenburgh C, Turk J, Heinecke JW (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
17. Cuzzocrea S, Zingarelli B, Villari D, Caputi AP, Longo G (1998) Evidence for in vivo peroxynitrite production in human chronic hepatitis. Life Sci 63: PL25-PL30
18. De Andrade JA, Crow JP, Viera L, Bruce Alexander C, Randall Young K, McGiffin DC, Zorn GL, Zhu S, Matalon S, Jackson RM (2000) Protein nitration, metabolites of reactive nitrogen species, and inflammation in lung allografts. Am J Respir Crit Care Med 161: 2035-2042
19. Delatour T, Guy PA, Stadler RH, Turesky RJ (2002a) 3-Nitrotyrosine butyl ester: a novel derivative to assess tyrosine nitration in rat plasma by liquid chromatography-tandem mass spectrometry detection. Anal Biochem 302: 10-18
20. Delatour T, Richoz J, Vouros P, Turesky R (2002b) Simultaneous determination of 3-nitrotyrosine and tyrosine in plasma proteins of rats and assessment of artifactual tyrosine nitration. J Chromatogr B Analyt Technol Biomed Life Sci 779: 189
21. Feng Q, Lu X, Jones DL, Shen J, Arnold JM (2001) Increased inducible nitric oxide synthase expression contributes to myocardial dysfunction and higher mortality after myocardial infarction in mice. Circulation 104: 700-704
22. Ferdinandy P, Danial H, Ambrus I, Rothery RA, Schulz R (2000) Peroxynitrite is a major contributor to cytokine-induced myocardial contractile failure. Circ Res 87: 241-247
23. Ferrante RJ, Hantraye P, Brouillet E, Beal MF (1999) Increased nitrotyrosine immunoreactivity in substantia nigra neurons in MPTP treated baboons is blocked by inhibition of neuronal nitric oxide synthase. Brain Res 823: 177-182
24. Forster C, Clark HB, Ross ME, Iadecola C (1999) Inducible nitric oxide synthase expression in human cerebral infarcts. Acta Neuropathol (Berl) 97: 215-220
25. Frost MT, Halliwell B, Moore KP (2000) Analysis of free and protein-bound nitrotyrosine in human plasma by a gas chromatography/mass spectrometry method that avoids nitration artifacts. Biochem J 345 Pt 3: 453-458
26. Garcia-Monzon C, Majano PL, Zubia I, Sanz P, Apolinario A, Moreno-Otero R (2000) Intrahepatic accumulation of nitrotyrosine in chronic viral hepatitis is associated with histological severity of liver disease. J Hepatol 32: 331-338
27. Gaut JP, Byun J, Tran HD, Heinecke JW (2002a) Artifact-free quantification of free 3-chlorotyrosine, 3-bromotyrosine, and 3-nitrotyrosine in human plasma by electron capture-negative chemical ionization gas chromatography mass spectrometry and liquid chromatography-electrospray ionization tandem mass spectrometry. Anal Biochem 300: 252-259
28. Gaut JP, Byun J, Tran HD, Lauber WM, Carroll JA, Hotchkiss RS, Belaaouaj A, Heinecke JW (2002b) Myeloperoxidase produces nitrating oxidants in vivo. J Clin Invest 109: 1311-1319
29. Giasson BI, Duda JE, Murray IV, Chen Q, Souza JM, Hurtig HI, Ischiropoulos H, Trojanowski JQ, Lee VM (2000) Oxidative damage linked to neurodegeneration by selective alpha-synuclein nitration in synucleinopathy lesions. Science 290: 985-989
30. Good PF, Hsu A, Werner P, Perl DP, Olanow CW (1998) Protein nitration in Parkinson's disease. J Neuropathol Exp Neurol 57: 338-342
31. Good PF, Werner P, Hsu A, Olanow CW, Perl DP (1996) Evidence of neuronal oxidative damage in Alzheimer's disease. Am J Pathol 149: 21-28
32. Green JM (1996) A practical guide to analytical method validation. Anal Chem 68: 305A-309A
33. Haddad IY, Pataki G, Hu P, Galliani C, Beckman JS, Matalon S (1994) Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J Clin Invest 94: 2407-2413
34. Halliwell B, Zhao K, Whiteman M (1999) Nitric oxide and peroxynitrite. The ugly, the uglier and the not so good: a personal view of recent controversies. Free Radic Res 31: 651-669
35. Hanazawa T, Kharitonov SA, Barnes PJ (2000) Increased nitrotyrosine in exhaled breath condensate of patients with asthma. Am J Respir Crit Care Med 162: 1273-1276
36. Hansen PR, Holm AM, Svendsen UG, Olsen PS, Andersen CB (2000) Apoptosis and formation of peroxynitrite in the lungs of patients with obliterative bronchiolitis. J Heart Lung Transplant 19: 160-166
37. Hashimoto S, Takahashi K, Ochs RL, Coutts RD, Amiel D, Lotz M (1999) Nitric oxide production and apoptosis in cells of the meniscus during experimental osteoarthritis. Arthritis Rheum 42: 2123-2131
38. Hensley K, Maidt ML, Pye QN, Stewart CA, Wack M, Tabatabaie T, Floyd RA (1997) Quantitation of protein-bound 3-nitrotyrosine and 3,4- dihydroxyphenylalanine by high-performance liquid chromatography with electrochemical array detection [published erratum appears in Anal Biochem 1998 Feb 1; 256(1): 148]. Anal Biochem 251: 187-195
39. Hensley K, Maidt ML, Yu Z, Sang H, Markesbery WR, Floyd RA (1998) Electrochemical analysis of protein nitrotyrosine and dityrosine in the Alzheimer brain indicates region-specific accumulation. J Neurosci 18: 8126-8132
40. Hurst JK (2002) Whence nitrotyrosine? J Clin Invest 109: 1287-1289
41. Ishida N, Hasegawa T, Mukai K, Watanabe M, Nishino H (2002) Determination of nitrotyrosine by HPLC-ECD and its application. J Vet Med Sci 64: 401-404
42. Jiang H, Balazy M (1998) Detection of 3-nitrotyrosine in human platelets exposed to peroxynitrite by a new gas chromatography/mass spectrometry assay. Nitric Oxide 2: 350-359
43. Kamisaki Y, Wada K, Nakamoto K, Kishimoto Y, Kitano M, Itoh T (1996) Sensitive determination of nitrotyrosine in human plasma by isocratic high-performance liquid chromatography. J Chromatogr B Biomed Appl 685: 343-347
44. Kaur H, Halliwell B (1994) Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitrotyrosine in serum and synovial fluid from rheumatoid patients. FEBS Lett 350: 9-12
45. Kaur H, Lyras L, Jenner P, Halliwell B (1998) Artefacts in HPLC detection of 3-nitrotyrosine in human brain tissue. J Neurochem 70: 2220-2223
46. Khan J, Brennand DM, Bradley N, Gao B, Bruckdorfer R, Jacobs M, Brennan DM (1998) 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method [published erratum appears in Biochem J 1998 Jun 15; 332 (Pt 3): 808]. Biochem J 330: 795-801
47. Kharitonov SA, Barnes PJ (2002) Biomarkers of some pulmonary diseases in exhaled breath. Biomarkers 7: 1-32
48. Leeuwenburgh C, Hardy MM, Hazen SL, Wagner P, Oh IS, Steinbrecher UP, Heinecke JW (1997) Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima. J Biol Chem 272: 1433-1436
49. Leeuwenburgh C, Hansen P, Shaish A, Holloszy JO, Heinecke JW (1998) Markers of protein oxidation by hydroxyl radical and reactive nitrogen species in tissues of aging rats. Am J Physiol 274: R453-R461
50. Liu D, Ling X, Wen J, Liu J (2000) The role of reactive nitrogen species in secondary spinal cord injury: formation of nitric oxide, peroxynitrite, and nitrated protein. J Neurochem 75: 2144-2154
51. Mihm MJ, Coyle CM, Schanbacher BL, Weinstein DM, Bauer JA (2001) Peroxynitrite induced nitration and inactivation of myofibrillar creatine kinase in experimental heart failure. Cardiovasc Res 49: 798-807
52. Morrissey B, Schilling K, Weil J, Silkoff P, Rodman D (2002) Nitric oxide and protein nitration in the cystic fibrosis airway. Arch Biochem Biophys 406: 33
53. Nag S, Picard P, Stewart DJ (2001) Expression of nitric oxide synthases and nitrotyrosine during blood-brain barrier breakdown and repair after cold injury. Lab Invest 81: 41-49
54. Ohshima H, Celan I, Chazotte L, Pignatelli B, Mower HF (1999) Analysis of 3-nitrotyrosine in biological fluids and protein hydrolyzates by high-performance liquid chromatography using a postseparation, on-line reduction column and electrochemical detection: results with various nitrating agents. Nitric Oxide 3: 132-141
55. Ohshima H, Friesen M, Brouet I, Bartsch H (1990) Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem Toxicol 28: 647-652
56. Oldreive C, Bradley N, Bruckdorfer R, Rice-Evans C (2001) Lack of influence of dietary nitrate/nitrite on plasma nitrotyrosine levels measured using a competitive inhibition of binding ELISA assay. Free Radic Res 35: 377-386
57. Oleszak EL, Zaczynska E, Bhattacharjee M, Butunoi C, Legido A, Katsetos CD (1998) Inducible nitric oxide synthase and nitrotyrosine are found in monocytes/macrophages and/or astrocytes in acute, but not in chronic, multiple sclerosis. Clin Diagn Lab Immunol 5: 438-445
58. Pelletier JP, Lascau-Coman V, Jovanovic D, Fernandes JC, Manning P, Connor JR, Currie MG, Martel-Pelletier J (1999) Selective inhibition of inducible nitric oxide synthase in experimental osteoarthritis is associated with reduction in tissue levels of catabolic factors. J Rheumatol 26: 2002-2014
59. Pennathur S, Jackson-Lewis V, Przedborski S, Heinecke JW (1999) Mass spectrometric quantification of 3-nitrotyrosine, ortho-tyrosine, and o,o′-dityrosine in brain tissue of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine-treated mice, a model of oxidative stress in Parkinson's disease. J Biol Chem 274: 34621-34628
60. Petruzzelli S, Puntoni R, Mimotti P, Pulera N, Baliva F, Fornai E, Giuntini C (1997) Plasma 3-nitrotyrosine in cigarette smokers. Am J Respir Crit Care Med 156: 1902-1907
61. Ravalli S, Albala A, Ming M, Szabolcs M, Barbone A, Michler RE, Cannon PJ (1998) Inducible nitric oxide synthase expression in smooth muscle cells and macrophages of human transplant coronary artery disease. Circulation 97: 2338-2345
62. Sakurai M, Fukuyama N, Iguchi A, Akimoto H, Ohmi M, Yokoyama H, Nakazawa H, Tabayashi K (1999) Quantitative analysis of cardiac 3-L-nitrotyrosine during acute allograft rejection in an experimental heart transplantation. Transplantation 68: 1818-1822
63. Schwedhelm E, Tsikas D, Gutzki FM, Frolich JC (1999) Gas chromatographic-tandem mass spectrometric quantification of free 3-nitrotyrosine in human plasma at the basal state. Anal Biochem 276: 195-203
64. Shigenaga MK (1999) Quantitation of protein-bound 3-nitrotyrosine by high-performance liquid chromatography with electrochemical detection. Methods Enzymol 301: 27-40
65. Shigenaga MK, Lee HH, Blount BC, Christen S, Shigeno ET, Yip H, Ames BN (1997) Inflammation and NO(X)-induced nitration: assay for 3-nitrotyrosine by HPLC with electrochemical detection. Proc Natl Acad Sci USA 94: 3211-3216
66. Singer II, Kawka DW, Scott S, Weidner JR, Mumford RA, Riehl TE, Stenson WF (1996) Expression of inducible nitric oxide synthase and nitrotyrosine in colonic epithelium in inflammatory bowel disease. Gastroenterology 111: 871-885
67. Smith MA, Richey HP, Sayre LM, Beckman JS, Perry G (1997) Widespread peroxynitrite-mediated damage in Alzheimer's disease. J Neurosci 17: 2653-2657
68. Szabolcs M, Michler RE, Yang X, Aji W, Roy D, Athan E, Sciacca RR, Minanov OP, Cannon PJ (1996) Apoptosis of cardiac myocytes during cardiac allograft rejection. Relation to induction of nitric oxide synthase. Circulation 94: 1665-1673
69. Szabolcs MJ, Ravalli S, Minanov O, Sciacca RR, Michler RE, Cannon PJ (1998) Apoptosis and increased expression of inducible nitric oxide synthase in human allograft rejection. Transplantation 65: 804-812
70. ter Steege JC, Koster-Kamphuis L, van Straaten EA, Forget PP, Buurman WA (1998) Nitrotyrosine in plasma of celiac disease patients as detected by a new sandwich ELISA. Free Radic Biol Med 25: 953-963
71. Teunissen CE, de Vente J, Steinbusch HW, De Bruijn C (2002) Biochemical markers related to Alzheimer's dementia in serum and cerebrospinal fluid. Neurobiol Aging 23: 485-508
72. Tohgi H, Abe T, Yamazaki K, Murata T, Ishizaki E, Isobe C (1999) Alterations of 3-nitrotyrosine concentration in the cerebrospinal fluid during aging and in patients with Alzheimer's disease. Neurosci Lett 269: 52-54
73. van der Veen RC, Hinton DR, Incardonna F, Hofman FM (1997) Extensive peroxynitrite activity during progressive stages of central nervous system inflammation. J Neuroimmunol 77: 1-7
74. Viera L, Ye YZ, Estevez AG, Beckman JS (1999) Immunohistochemical methods to detect nitrotyrosine. Methods Enzymol 301: 373-381
75. Yamaguchi Y, Okabe K, Matsumura F, Akizuki E, Matsuda T, Ohshiro H, Liang J, Yamada S, Mori K, Ogawa M (1999) Peroxynitrite formation during rat hepatic allograft rejection. Hepatology 29: 777-784
76. Yi D-H, Ingelse BA, Duncan MW, Smythe GA (2000) Quantification of 3-nitrotyrosine in biological tissues and fluids: generating valid results by eliminating artifactual formation. J Am Soc Mass Spectrom 11: 578-586
77. Zweier JL, Fertmann J, Wei G (2001) Nitric oxide and peroxynitrite in postischemic myocardium. Antioxid Redox Signal 3: 11-22