Analytical methods for 3-nitrotyrosine quantification in biological samples: The unique role of tandem mass spectrometry

Amino Acids

Volumn 42, Issue 1, 2012, Pages 45-63

  Tsikas, Dimitrios ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

Author keywords

Misidentification; Nitration; Peroxynitrite; Quantification; Tandem mass spectrometry; Tyrosine; Validation

Indexed keywords

3 NITROTYROSINE; ATORVASTATIN; CARVEDILOL; GLYCERYL TRINITRATE; ISOSORBIDE DINITRATE; NEBIVOLOL; PENTAERYTHRITYL TETRANITRATE; PLACEBO; REACTIVE NITROGEN SPECIES; TYROSINE; 3-NITROTYROSINE; DRUG DERIVATIVE; PROTEIN;

AEROBIC METABOLISM; BLOOD LEVEL; CEREBROSPINAL FLUID LEVEL; CONFERENCE PAPER; ELECTROCHEMICAL DETECTION; ELECTRON CAPTURE DETECTION; ENZYME LINKED IMMUNOSORBENT ASSAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIMIT OF DETECTION; LIMIT OF QUANTITATION; MASS FRAGMENTOGRAPHY; NITRATION; NITROSATIVE STRESS; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEOMICS; QUANTITATIVE ANALYSIS; RELIABILITY; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; URINARY EXCRETION; URINE LEVEL; ANIMAL; BLOOD; CHEMISTRY; HUMAN; METABOLISM; REVIEW; URINE;

ANIMALS; HUMANS; PROTEINS; TANDEM MASS SPECTROMETRY; TYROSINE;

EID: 84858079161     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0604-5     Document Type: Conference Paper

References (149)

1. Abello N, Kerstjens HAM, Postma DS, Bischoff R (2009) Protein tyrosine nitration: selectivity, physicochemical and biological consequences, denitration, and proteomics methods for the identification of tyrosine-nitrated proteins. J Prot Res 8:3222-3238
2. Ahmed N, Battah S, Karachalias N, Babaei-Jadidi R, Horányi M, Baróti K, Hollan S, Thornalley PJ (2003) Increased formation of methylglyoxal and protein glycation, oxidation and nitrosation in triosephosphate isomerase deficiency. Biochim Biophys Acta 1639(2):121-132 (Pubitemid 38366216)
3. Ahmed N, Babaei-Jadidi R, Howell SK, Beisswenger PJ, Thornalley PJ (2005) Degradation products of proteins damaged by glycation, oxidation and nitration in clinical type 1 diabetes. Diabetologia 48:1590-1603 (Pubitemid 41175513)
4. Amoresano A, Chiappetta G, Pucci P, D'Ischia M, Marino G (2007) Bidimensional tandem mass spectrometry for selective identification of nitration sites in proteins. Anal Chem 79:2109-2117 (Pubitemid 46355246)
5. Araujo P (2009) Key aspects of analytical method validation and linearity evaluation. J Chromatogr B 877:2224-2234
6. 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 (Pubitemid 32717479)
7. Baraldi E, Giordano G, Pasquale MF, Carraro S, Mardegan A, Bonetto G, Bastardo C, Zacchello F, Zanconato S (2006) 3-Nitrotyrosine, a marker of nitrosative stress, is increased in breath condensate of allergic asthmatic children. Allergy 61:90-96 (Pubitemid 43381197)
8. Bigelow DJ, Qian WJ (2008) Quantitative proteome mapping of nitrotyrosines. Methods Enzymol 440:191-205
9. Celio S, Troxler H, Durka SS, Chládek J, Wildhaber JH, Sennhauser FH, Heizmann CW, Moeller A (2006) Free 3-nitrotyrosine in exhaled breath condensates of children fails as a marker for oxidative stress in stable cystic fibrosis and asthma. Nitric Oxide 15:226-232 (Pubitemid 44466433)
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 (Pubitemid 32642455)
11. Chatterjee S, Lardinois O, Bonini MG, Bhattacharjee S, Stadler K, Corbett J, Deterding LJ, Tomer KB, Kadiiska M, Mason RP (2009) Site-specific carboxypeptidase B1 tyrosine nitration and pathophysiological implications following its physical association with nitric oxide synthase-3 in experimental sepsis. J Immunol 183:4055-4066
12. Chen HJ, Chiu WL (2008) Simultaneous detection and quantification of 3-nitrotyrosine and 3-bromotyrosine in human urine by stable isotope dilution liquid chromatography tandem mass spectrometry. Toxicol Lett 181:31-39
13. Chen HJ, Chang CM, Lin WP, Cheng DL, Leong MI (2008a) H2O2/ nitrite-induced post-translational modifications of human hemoglobin determined by mass spectrometry: redox regulation of tyrosine nitration and 3-nitrotyrosine reduction by antioxidants. Chembiochem 9:312-323
14. Chen CL, Chen J, Rawale S, Varadharaj S, Kaumaya PP, Zweier JL, Chen YR (2008b) Protein tyrosine nitration of the flavin subunit is associated with oxidative modification of mitochondrial complex II in the post-ischemic myocardium. J Biol Chem 283:27991-28003
15. Conventz A, Musiol A, Brodowsky C, Müller-Lux A, Dewes P, Kraus T, Schettgen T (2007) Simultaneous determination of 3-nitrotyrosine, tyrosine, hydroxyproline and proline in exhaled breath condensate by hydrophilic interaction liquid chromatography/ electrospray ionization tandem mass spectrometry. J Chromatogr B 860:78-85 (Pubitemid 350161461)
16. Dalle-Donne I, Rossi R, Colombo R, Giustarini D, Milzani A (2006) Biomarkers of oxidative damage in human disease. Clin Chem 42:601-623
17. Danielson SR, Held JM, Schilling B, Oo M, Gibson BW, Andersen JK (2009) Preferentially increased nitration of alpha-synuclein at tyrosine-39 in a cellular oxidative model of Parkinson's disease. Anal Chem 81:7823-7828
18. 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 (Pubitemid 34174604)
19. Delatour T, Richoz J, Vuichoud J, Stadler RH (2002b) Artifactual nitration controlled measurement of protein-bound 3-nitro-Ltyrosine in biological fluids and tissues by isotope dilution liquid chromatography electrospray ionization tandem mass spectrometry. Chem Res Toxicol 15:1209-1217 (Pubitemid 35222187)
20. Denicola A, Freemann BA, Trujillo M, Radi R (1996) Peroxynitrite reaction with carbon dioxide/bicarbonate: kinetics and influence on peroxynitrite- mediated oxidations. Arch Biochem Biophys 333:49-58 (Pubitemid 26276973)
21. Dewé W (2009) Review of statistical methodologies used to compare (bio)assays. J Chromatogr B 877:2208-2213
22. Ducrocq C, Blanchard B, Pignatelli B, Ohshima H (1999) Peroxynitrite: an endogenous oxidizing and nitrating agent. Cell Mol Life Sci 55:1068-1077 (Pubitemid 29361073)
23. Duncan MW (2003) A review of approaches to the analysis of 3-nitrotyrosine. Amino Acids 25:351-361 (Pubitemid 38041271)
24. Duncan MW (2007) Omics and its 15 minutes. Exp Biol Med 232:471-472 (Pubitemid 46524467)
25. Duncan MW, Yergey AL, Patterson SD (2009) Quantifying proteins by mass spectrometry: the selectivity of SRM is only part problem. Proteomics 9:1124-1127
26. Fahlbusch SA, Tsikas D, Mehl C, Gutzki FM, Böger RH, Frölich JC, Stichtenoth DO (2004) Effects of carvedilol on oxidative stress in human endothelial cells and healthy volunteers. Eur J Clin Pharmacol 60:83-88 (Pubitemid 38656126)
27. Fatouros IG, Jamurtas AZ, Villiotou V, Pouliopoulou S, Fotinakis P, Taxildaris K, Deliconstantinos G (2004) Oxidative stress responses in older men during endurance training and detraining. Med Sci Sports Exerc 36:2065-2072 (Pubitemid 39612847)
28. Fontana M, Pecci L, Schininá ME, Montefoschi G, Rosei MA (2006) Oxidative and nitrative modifications of enkephalins by reactive nitrogen species. Free Radic Res 40:697-706 (Pubitemid 44489863)
29. 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 345:453-458 (Pubitemid 30099072)
30. Fujigaki H, Saito K, Lin F, Fujigaki S, Takahashi K, Martin BM, Chen CY, Masuda J, Kowalak J, Takikawa O, Seishima M, Markey SP (2006) Nitration and inactivation of IDO by peroxynitrite. J Immunol 176:372-379 (Pubitemid 43023283)
31. Gaut JP, Byun J, Tran HD, Heinecke JW (2002) 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 (Pubitemid 34093701)
32. Ghesquière B, Goethals M, Van Damme J, Staes A, Timmerman E, Vandekerckhove J, Gevaert K (2006) Improved tandem mass spectrometric characterization of 3-nitrotyrosine sites in peptides. Rapid Commun Mass Spectrom 20:2885-2893 (Pubitemid 44526626)
33. Ghosh S, Janocha AJ, Aronica MA, Swaidani S, Comhair SA, Xu W, Zheng L, Kaveti S, Kinter M, Hazen SL, Erzurum SC (2006) Nitrotyrosine proteome survey in asthma identifies oxidative mechanism of catalase inactivation. J Immunol 176:5587-5597
34. Giustarini D, Milzani A, Dalle-Donne I, Rossi R (2007) Detection of S-nitrosothiols in biological fluids: a comparison among the most widely applied methodologies. J Chromatogr B 851:124-139 (Pubitemid 46720138)
35. Giustarini D, Dalle-Donne I, Tsikas D, Rossi R (2009) Oxidative stress in human diseases: origin, link, measurement, mechanisms, and biomarkers. Crit Rev Clin Lab Sci 46:241-281
36. Göen T, Muller-Lux A, Dewes P, Musiol S, Kraus T (2005) Sensitive and accurate analyses of free 3-nitrotyrosine in exhaled breath condensate by LC-MS/MS. J Chromatogr B 826:261-266 (Pubitemid 41446460)
37. Goldstein S, Czapski G (1999) Viscosity effects on the reaction of peroxynitrite with CO2: evidence for radical formation in a solvent cage. J Am Chem Soc 121:2444-2447 (Pubitemid 29153454)
38. Gow A, Duran D, Thom SR, Ischiropoulos H (1996) Carbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Arch Biochem Biophys 333:42-48 (Pubitemid 26276972)
39. Halliwell B (1997) What nitrates tyrosine? Is nitrotyrosine specific as a biomarker of peroxynitrite formation in vivo? FEBS Lett 411:155-160
40. Hong SJ, Gokulrangan G, Schöneich C (2007) Proteomic analysis of age dependent nitration of rat cardiac proteins by solution isoelectric focusing coupled to nanoHPLC tandem mass spectrometry. Exp Gerontol 42(7):639-651 (Pubitemid 46756107)
41. Hsiai TK, Hwang J, Barr ML, Correa A, Hamilton R, Alavi M, Rouhanizadeh M, Cadenas E, Hazen SL (2007) Hemodynamics influences vascular peroxynitrite formation: implication for lowdensity lipoprotein apo-B-100 nitration. Free Radic Biol Med 42:519-529 (Pubitemid 46162120)
42. Huie RE, Padmaja S (1993) The reaction of NO with superoxide. Free Radic Res Commun 18:195-199
43. Ikeda K, Yukihiro Hiraoka B, Iwai H, Matsumoto T, Mineki R, Taka H, Takamori K, Ogawa H, Yamakura F (2007) Detection of 6- nitrotryptophan in proteins by Western blot analysis and its application for peroxynitrite-treated PC12 cells. Nitric Oxide 16:18-28 (Pubitemid 44820876)
44. Inoue H, Hisamatsu K, Ando K, Ajisaka R, Kumagai N (2002) Determination of nitrotyrosine and related compounds in biological specimens by competitive enzyme immunoassay. Nitric Oxide 7:11-17 (Pubitemid 35007254)
45. Ischiropoulos H (1998) Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch Biochem Biophys 356:1-11 (Pubitemid 28364347)
46. Janué A, Odena MA, Oliveira E, Olivé M, Ferrer I (2007) Desmin is oxidized and nitrated in affected muscles in myotilinopathies and desminopathies. J Neuropathol Exp Neurol 66:711-723 (Pubitemid 47344250)
47. Jiao K, Mandapati S, Skipper PL, Tannenbaum SR, Wishnok JS (2001) Site-selective nitration of tyrosine in human serum albumin by peroxynitrite. Anal Biochem 293:43-52 (Pubitemid 32500504)
48. Jourd'heuil D, Miranda KM, Kim SM, Espey MG, Vodovotz Y, Laroux S, Mai CT, Miles AM, Grisham MB, Wink DA (1999) The oxidative and nitrosative chemistry of the nitric oxide/ superoxide reaction in the presence of bicarbonate. Arch Biochem Biophys 365:92-100 (Pubitemid 29394254)
49. 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 685:343-347 (Pubitemid 26382417)
50. Kanski J, Schöneich C (2005) Protein nitration in biological aging: proteomic and tandem mass spectrometric characterization of nitrated sites. Methods Enzymol 396:160-171 (Pubitemid 41603547)
51. Kanski J, Hong SJ, Schöneich C (2005a) Proteomic analysis of protein nitration in aging skeletal muscle and identification of nitrotyrosine- containing sequences in vivo by nanoelectrospray ionization tandem mass spectrometry. J Biol Chem 280:24261-24266 (Pubitemid 40884916)
52. Kanski J, Behring A, Pelling J, Schöneich C (2005b) Proteomic identification of 3-nitrotyrosine-containing rat cardiac proteins: effects of biological aging. Am J Physiol Heart Circ Physiol 288:H371-H381 (Pubitemid 40023869)
53. Kato Y, Dozaki N, Nakamura T, Kitamoto N, Yoshida A, Naito M, Kitamura M, Osawa T (2009) Quantification of modified tyrosines in healthy and diabetic human urine using liquid chromatography/ tandem mass spectrometry. J Clin Biochem Nutr 44:67-78
54. Keimer R, Stutzer FK, Tsikas D, Troost R, Gutzki FM, Frölich JC (2003) Lack of oxidative stress during sustained therapy with isosorbide dinitrate and pentaerythrityl tetranitrate in healthy humans: a randomized, double-blind crossover study. J Cardiovasc Pharmacol 41:284-292 (Pubitemid 36135254)
55. Khan J, Brennan DM, Bradley N, Gao B, Bruckdorfer R, Jacobs M (1998) 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochem J 330:795-801 (Pubitemid 28111980)
56. Kim CH, Zou Y, Kim DH, Kim ND, Yu BP, Chung HY (2006) Proteomic analysis of nitrated and 4-hydroxy-2-nonenal-modified serum proteins during aging. J Gerontol A Biol Sci Med Sci 61:332-338
57. Kingdon EJ, Mani AR, Frost MT, Denton CP, Powis SH, Black CM, Moore KP (2006) Low plasma protein nitrotyrosine levels distinguish primary Raynaud's phenomenon from scleroderma. Ann Rheum Dis 65:952-954
58. Kissner R, Koppenol W (2002) Product distribution of peroxynitrite decay as a function of pH, temperature, and concentration. J Am Chem Soc 124:234-239 (Pubitemid 34062755)
59. Lärstad M, Söderling AS, Caidahl K, Olin AC (2005) Selective quantification of free 3-nitrotyrosine in exhaled breath condensate in asthma using gas chromatography/tandem mass spectrometry. Nitric Oxide 13:134-144 (Pubitemid 41133680)
60. Lemercier JN, Padmaja S, Cueto R, Squadrito GL, Uppu RM, Pryor WA (1997) Carbon dioxide modulation of hydroxylation and nitration of phenol by peroxynitrite. Arch Biochem Biophys 345:160-170 (Pubitemid 27374287)
61. Lin HL, Myshkin E, Waskell L, Hollenberg PF (2007) Peroxynitrite inactivation of human cytochrome P450s 2B6 and 2E1: heme modification and site-specific nitrotyrosine formation. Chem Res Toxicol 20:1612-1622 (Pubitemid 350275606)
62. Liu B, Tewari AK, Zhang L, Green-Church KB, Zweier JL, Chen YR, He G (2009) Proteomic analysis of protein tyrosine nitration after ischemia reperfusion injury: mitochondria as the major target. Biochim Biophys Acta 1794:476-485
63. Lorch SA, Banks BA, Christie J, Merrill JD, Althaus J, Schmidt K, Ballard PL, Ischiropoulos H, Ballard RS (2003) Plasma 3-nitrotyrosine and outcome in neonates with severe bronchopulmonary dysplasia after inhaled nitric oxide. Free Radic Biol Med 34:1146-1152 (Pubitemid 36423365)
64. 2-catalyzed one-electron oxidations by peroxynitrite: properties of the reactive intermediated. Inorg Chem 37:294-301 (Pubitemid 128483312)
65. Maeso N, Cifuentes A, Barbas C (2004) Large-volume sample stacking-capillary electrophoresis used for the determination of 3-nitrotyrosine in rat urine. J Chromatogr B 809:147-152 (Pubitemid 38998432)
66. Magné J, Huneau JF, Tsikas D, Delamasure S, Rochette L, Tomé D, Mariotti F (2009) Rapeseed protein in a high-fat mixed meal alleviates postprandial systemic and vascular endothelial dysfunction in healthy rats. J Nutr 139:1660-1666
67. Matalon S, Shrestha K, Kirk M, Waldheuser S, McDonald B, Smith K, Gao Z, Belaaouaj A, Crouch EC (2009) Modification of surfactant protein D by reactive oxygen-nitrogen intermediates is accompanied by loss of aggregating activity, in vitro and in vivo. FASEB J 23:1415-1430
68. Nakagawa H, Komai N, Takusagawa M, Miura Y, Toda T, Miyata N, Ozawa T, Ikota N (2007) Nitration of specific tyrosine residues of cytochrome C is associated with caspase-cascade inactivation. Biol Pharm Bull 30:15-20 (Pubitemid 46066312)
69. Nemirovskiy OV, Radabaugh MR, Aggarwal P, Funckes-Shippy CL, Mnich SJ, Meyer DM, Sunyer T, Mathews WR, Misko TP (2009) Plasma 3-nitrotyrosine is a biomarker in animal models of arthritis: pharmacological dissection of iNOS's role in disease. Nitric Oxide 20:150-156
70. Nicholls SJ, Shen Z, Fu X, Levison BS, Hazen SL (2005) Quantification of 3-nitrotyrosine levels using a benchtop ion trap mass spectrometry method. Methods Enzymol 396:245-266 (Pubitemid 41613564)
71. Nicholls SJ, Wang Z, Koeth R, Levison B, DelFraino B, Dzavik V, Griffith OW, Hathaway D, Panza JA, Nissen SE, Hochman JS, Hazen SL (2007) Metabolic profiling of arginine and nitric oxide pathways predicts hemodynamic abnormalities and mortality in patients with cardiogenic shock after acute myocardial infarction. Circulation 116:2315-2324 (Pubitemid 350100338)
72. Niki E (2009) Lipid peroxidation: physiological levels and dual biological effects. Free Radic Biol Med 47:469-484
73. Nuriel T, Deeb RS, Hajjar DP, Gross SS (2008) Protein 3- nitrotyrosine in complex biological samples: quantification by high-pressure liquid chromatography/electrochemical detection and emergence of proteomic approaches for unbiased identification of modification sites. Methods Enzymol 441:1-17
74. Ohshima H, Friesen M, Brouet I, Bartsch H (1990) Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem Toxic 28:647-652
75. Ohshima H, Celan I, Chazotte L, Pignatelli B, Mower HF (1999) Analysis of 3-nitrotyrosine in biological fluids and protein hydrolysates 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 (Pubitemid 29394858)
76. Ohya M, Marukawa S, Inoue T, Ueno N, Hosohara K, Terada N, Kosaka H (2002) Plasma nitrotyrosine concentration relates to prognosis in human septic shock. Shock 18:116-118
77. Orhan H, Vermeulen NP, Tump C, Zappey H, Meerman JH (2004) Simultaneous determination of tyrosine, phenylalanine and deoxyguanosine oxidation products by liquid chromatographytandem mass spectrometry as non-invasive biomarkers for oxidative damage. J Chromatogr B 799:245-254 (Pubitemid 37510227)
78. Orhan H, Coolen S, Meerman JHN (2005) Quantification of urinary o,o-dityrosine, a biomarker of oxidative damage to proteins, by high performance liquid chromatography with triple quadrupole tandem mass spectrometry. A comparison with ion-trap tandem mass spectrometry. J Chromatogr B 827:104-108 (Pubitemid 41551603)
79. Palamalai V, Darrow RM, Organisciak DT, Miyagi M (2006) Lightinduced changes in protein nitration in photoreceptor rod outer segments. Mol Vis 12:1543-1551 (Pubitemid 46029771)
80. Pannala AS, Mani AR, Spencer JP, Skinner V, Bruckdorfer KR, Moore KP, Rice-Evans CA (2003) The effect of dietary nitrate on salivary, plasma, and urinary nitrate metabolism in humans. Free Radic Biol Med 34:576-584 (Pubitemid 36254831)
81. Pannala AS, Mani AR, Rice-Evans CA, Moore KP (2006) pHdependent nitration of para-hydroxyphenylacetic acid in the stomach. Free Radic Biol Med 41:896-901 (Pubitemid 44247542)
82. Parastatidis I, Thomson L, Fries DM, Moore RE, Tohyama J, Fu X, Hazen SL, Heijnen HF, Dennehy MK, Liebler DC, Rader DJ, Ischiropoulos H (2007) Increased protein nitration burden in the atherosclerotic lesions and plasma of apolipoprotein A-I deficient mice. Circ Res 101:368-376 (Pubitemid 47267705)
83. Park SW, Huq MD, Hu X, Wei LN (2005) Tyrosine nitration on p65: a novel mechanism to rapidly inactivate nuclear factor-kappaB. Mol Cell Proteomics 4:300-309 (Pubitemid 40439773)
84. Pavlovic R, Santaniello E, Chiesa LM, Biondi PA (2009) New procedure for the determination of 3-nitrotyrosine in plasma by GC-ECD. Chromatographia 70:637-641
85. Pennathur S, Bergt C, Shao B, Byun J, Kassim SY, Singh P, Green PS, McDonald TO, Brunzell J, Chait A, Oram JF, O'Brien K, Geary RL, Heinecke JW (2004) Human atherosclerotic intima and blood of patients with established coronary artery disease contain high density lipoprotein damaged by reactive nitrogen species. J Biol Chem 279:42977-42983 (Pubitemid 39372190)
86. Peters T Jr (1985) Serum albumin. Adv Prot Chem 37:161-245
87. Petersson AS, Steen H, Kalume DE, Caidahl K, Roepstorff P (2001) Investigation of tyrosine nitration in proteins by mass spectrometry. J Mass Spectrom 36:616-625 (Pubitemid 32624621)
88. Petre BA, Youhnovski N, Lukkari J, Weber R, Przybylski M (2005) Structural characterisation of tyrosine-nitrated peptides by ultraviolet and infrared matrix-assisted laser desorption/ionisation Fourier transform ion cyclotron resonance mass spectrometry. Eur J Mass Spectrom (Chichester, Eng) 11:513-518 (Pubitemid 41796539)
89. 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 (Pubitemid 28011800)
90. Pfeiffer S, Gorren ACF, Schmidt K, Werner ER, Hansert B, Bole DS, Mayer B (1997) Metabolic fate of peroxynitrite in aqueous solution: Reaction with nitric oxide and pH-dependent decomposition to nitrite and oxygen in a 2:1 stoichiometry. J Biol Chem 272:3465-3470
91. Pham VV, Stichtenoth DO, Tsikas D (2009) Nitrite correlates with 3-nitrotyrosine but not with the F2-isoprostane 15(S)-8-iso-PGF2a in urine of rheumatic patients. Nitric Oxide 21:210-215
92. Pietraforte D, Salzano AM, Scorza G, Minetti M (2004) Scavenging of reactive nitrogen species by oxygenated hemoglobin: globin radicals and nitrotyrosines distinguish nitrite from nitric oxide reaction. Free Radic Biol Med 37:1244-1255 (Pubitemid 39296749)
93. Pignatelli B, Li CQ, Boffetta P, Chen Q, Ahrens W, Nyberg F, Mukeria A, Bruske-Hohlfeld I, Fortes C, Constantinescu V, Ischiropoulos H, Ohshima H (2001) Nitrated and oxidized plasma proteins in smokers and lung cancer patients. Cancer Res 61:778-784 (Pubitemid 32128646)
94. Pop-Busui R, Oral E, Raffel D, Byun J, Bajirovic V, Vivekanandan- Giri A, Kellogg A, Pennathur S, Stevens MJ (2009) Impact of rosiglitazone and glyburide on nitrosative stress and myocardial blood flow regulation in type 2 diabetes mellitus. Metabolism 58:989-994
95. Prokai L (2009) Misidentification of nitrated peptides: comments on Hong SJ, Gokulrangan G, Scöneich C (2007) Proteomic analysis of age-dependent nitration of rat cardiac proteins by solution isoelectric focusing coupled to nanoHPLC tandem mass spectrometry. Exp Gerontol 42:639-651.
96. Exp Gerontol 44:367-369
97. Rabbani N, Thornalley PJ (2008) Assay of 3-nitrotyrosine in tissues and body fluids by liquid chromatography with tandem mass spectrometric detection. Methods Enzymol 440:337-359
98. Radabaugh MR, Nemirovskiy OV, Misko TP, Aggarwal P, Mathews WR (2008) Immunoaffinity liquid chromatography-tandem mass spectrometry detection of nitrotyrosine in biological fluids: development of a clinically translatable biomarker. Anal Biochem 380:68-76 (Pubitemid 351938675)
99. Radi R, Peluffo G, Alvarez MN, Naviliat M, Cayota A (2001) Unravelling peroxynitrite formation in biological systems. Free Radic Biol Med 30:463-488 (Pubitemid 32162954)
100. Richards DA, Silva MA, Devall AJ (2006) Electrochemical detection of free 3-nitrotyrosine: application to microdialysis studies. Anal Biochem 351:77-83
101. Rossner P Jr, Svecova V, Milcova A, Lnenickova Z, Solansky I, Santella RM, Sram RJ (2007) Oxidative and nitrosative stress markers in bus drivers. Mutat Res 617:23-32 (Pubitemid 46386096)
102. Ryberg H, Caidahl K (2007) Chromatographic and mass spectrometric methods for quantitative determination of 3-nitrotyrosine in biological samples and their application to human samples. J Chromatogr B 851:160-171 (Pubitemid 46720146)
103. Ryberg H, Söderling AS, Davidsson P, Blennow K, Caidahl K, Persson LI (2004) Cerebrospinal fluid levels of free 3-nitrotyrosine are not elevated in the majority of patients with amyotrophic lateral sclerosis or Alzheimer's disease. Neurochem Int 45:57-62 (Pubitemid 38479564)
104. Safinowski M, Wilhelm B, Reimer T, Weise A, Thomé N, Hänel H, Forst T, Pfützner A (2009) Determination of nitrotyrosine concentrations in plasma samples of diabetes mellitus patients by four different immunoassays leads to contradictive results and disqualifies the majority of the tests. Clin Chem Lab Med 47:483-488
105. Sarver A, Scheffler NK, Shetlar MD, Gibson BW (2001) Analysis of peptides and proteins containing nitrotyrosine by matrix-assisted laser desorption/ionization mass spectrometry. J Am Soc Mass Spectrom 12:439-448 (Pubitemid 34546613)
106. Schwedhelm E, Tsikas D, Gutzki FM, Frölich JC (1999) Gas chromatographic-tandem mass spectrometric quantification of free 3-nitrotyrosine in human plasma at the basal state. Anal Biochem 276:195-203 (Pubitemid 30013041)
107. Schwemmer M, Fink B, Köckerbauer R, Bassenge E (2000) How urine analysis reflects oxidative stress-nitrotyrosine as a potential marker. Clin Chim Acta 297:207-216 (Pubitemid 30332291)
108. Shao B, Bergt C, Fu X, Green P, Voss JC, Oda MN, Oram JF, Heinecke JW (2005) Tyrosine 192 in apolipoprotein A-I is the major site of nitration and chlorination by myeloperoxidase, but only chlorination markedly impairs ABCA1-dependent cholesterol transport. J Biol Chem 280:5983-5993 (Pubitemid 40280082)
109. Sharov VS, Galeva NA, Kanski J, Williams TD, Schöneich C (2006) Age-associated tyrosine nitration of rat skeletal muscle glycogen phosphorylase b: characterization by HPLC-nanoelectrospraytandem mass spectrometry. Exp Gerontol 41:407-416
110. Sharov VS, Galeva NA, Dremina ES, Williams TD, Schöneich C (2009) Inactivation of rabbit muscle glycogen phosphorylase b by peroxynitrite revisited: does the nitration of Tyr613 in the allosteric inhibition site control enzymatic function? Arch Biochem Biophys 484:155-166
111. Shimizu K, Ogawa F, Thiele JJ, Lee JB, Bae S, Sato S (2008) Increased levels of urinary nitrite and nitrotyrosine in Yusho victims 40 years after accidental poisoning witch polychlorinated biphenyls in Nagasaki, Japan. J Appl Toxicol 28:1040-1044
112. Shishehbor MH, Aviles RJ, Brennan ML, Fu X, Goormastic M, Pearce GL, Gokce N, Keaney JF Jr, Penn MS, Sprecher DL, Vita JA, Hazen SL (2003a) Association of nitrotyrosine levels with cardiovascular disease and modulation by statin therapy. JAMA 289:1675-1680 (Pubitemid 37430273)
113. Shishehbor MH, Brennan ML, Aviles RJ, Fu X, Penn MS, Sprecher DL, Hazen SL (2003b) Statins promote potent systemic antioxidant effects through specific inflammatory pathways. Circulation 108:426-431 (Pubitemid 36935535)
114. Söderling AS, Ryberg H, Gabrielson A, Lärstad M, Torén K, Niari S, Caidahl K (2003) A derivatization assay using gaschromatography/ negative chemical ionization tandem mass spectrometry to quantify 3-nitrotyrosine in human plasma. J Mass Spectrom 38:1187-1196 (Pubitemid 37508686)
115. Stevens SM, Prokai-Tatrai K, Prokai L (2008) Factors that contribute to the misidentification of tyrosine nitration by shotgun proteomics. Mol Cell Proteomics 7:2442-2451
116. Stöckl D, D'Hondt H, Thienpont LM (2009) Method validation across the disciplines-critical investigation of major validation criteria and associated experimental protocols. J Chromatogr B 877:2180-2190
117. Strand OA, Leone A, Gierrcksky KE, Kirkebøen KA (2000) Nitric oxide indices in human septic shock. Crit Care Med 28:2779-2785
118. Svatikova A, Wolk R, Wang HH, Otto ME, Bybee KA, Singh RJ, Somers VK (2004) Circulating free nitrotyrosine in obstructive sleep apnea. Am J Physiol Regul Comp Physiol 287:R284-R287 (Pubitemid 38970278)
119. Tedeschi G, Cappelletti G, Negri A, Pagliato L, Maggioni MG, Maci R, Ronchi S (2005) Characterization of nitroproteome in neuronlike PC12 cells differentiated with nerve growth factor: identification of two nitration sites in alpha-tubulin. Proteomics 5:2422-2432 (Pubitemid 40835413)
120. Tedeschi G, Cappelletti G, Nonnis S, Taverna F, Negri A, Ronchi C, Ronchi S (2007) Tyrosine nitration is a novel post-translational modification occurring on the neural intermediate filament protein peripherin. Neurochem Res 32:433-441 (Pubitemid 46295143)
121. ter Steege JCA, 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 (Pubitemid 28538562)
122. Thompson M, Ellison SLR, Wood R (2002) Harmonized guidelines for single-laboratory validation of methods of analysis. Pure Appl Chem 74:835-855
123. Thornalley PJ, Battah S, Ahmed N, Karachalias N, Agalou S, Babaei- Jadidi R, Dawnay A (2003) Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry. Biochem J 375(Pt 3):581-592 (Pubitemid 37433506)
124. Tohgi H, Abe T, Yamazaki K, Murata T, Ishizaki E, Isobe C (1999) Remarkable increase in cerebrospinal fluid 3-nitrotyrosine in patients with sporadic amyotrophic lateral sclerosis. Ann Neurol 46:129-131 (Pubitemid 29314394)
125. Troost R, Schwedhelm E, Rojczyk S, Tsikas D, Frölich JC (2000) Nebivolol decreases systemic oxidative stress in healthy volunteers. Br J Clin Pharmacol 50:377-379
126. Tsikas D (2006) Quantitative determination of free and proteinassociated 3-nitrotyrosine and S-nitrosothiols in the circulation by mass spectrometry and other methodologies: A critical review and discussion from the analytical and review point of view. In: Dalle-Donne I, Scaloni A, Butterfield DA (eds) Redox proteomics: from protein modifications to cellular dysfunction and diseases. Wiley, Hoboken, p 287
127. Tsikas D (2008) A critical review and discussion of analytical methods in the L-arginine/nitric oxide (NO) area of basic and clinical research. Anal Biochem 379:139-163
128. Tsikas D (2009a) A proposal for comparing methods of quantitative analysis of endogenous compounds in biological systems by using the relative lower limit of quantification (rLLOQ). J Chromatogr B 877:2244-2251
129. Tsikas D (2009b) Reliable quantification of endogenous free 3-nitrotyrosine in human plasma by GC-ECD or GC-MS in health and disease? Chromatographia 70:1767-1768
130. Tsikas D (2010a) Measurement of nitrotyrosine in plasma by immunoassays is fraught with danger: commercial availability is no guarantee of analytical reliability. Clin Chem Lab Med 48:141-143
131. Tsikas D (2010b) Quantitative analysis of biomarkers, drugs and toxins in biological samples by immunoaffinity chromatography coupled to mass spectrometry or tandem mass spectrometry: a focused review of recent applications. J Chromatogr B 878:133-148
132. Tsikas D, Caidahl K (2005) Recent methodological advances in the mass spectrometric analysis of free and protein-associated 3-nitrotyrosine in human plasma. J Chromatogr B 814:1-9 (Pubitemid 40017929)
133. Tsikas D, Schwedhelm E, Frölich JC (2002) Methodological considerations on the detection of 3-nitrotyrosine in the cardiovascular system. Circ Res 90:e70
134. Tsikas D, Schwedhelm E, Stutzer FK, Gutzki FM, Rode I, Mehls C, Frölich JC (2003) Accurate quantification of basal plasma levels of 3-nitrotyrosine and 3-nitrotyrosinoalbumin by gas chromatography- tandem mass spectrometry. J Chromatogr B 784:77-90 (Pubitemid 36009343)
135. Tsikas D, Mitschke A, Suchy MT, Gutzki FM, Stichtenoth DO (2005) Determination of 3-nitrotyrosine in human urine at the basal state by gas chromatography-tandem mass spectrometry and evaluation of the excretion after oral intake. J Chromatogr B 827:146-156 (Pubitemid 41551608)
136. Tsikas D, Dehnert S, Urban K, Surdacki A, Meyer HH (2009a) GCMS analysis of S-nitrosothiols after conversion to S-nitroso-Nacetyl cysteine ethyl ester and in-injector nitrosation of ethyl acetate. J Chromatogr B 877:3442-3455
137. Tsikas D, Zoerner A, Mitschke A, Homsi Y, Gutzki FM, Jordan J (2009b) Specific GC-MS/MS stable-isotope dilution methodology for free 9- and 10-nitro-oleic acid in human plasma challenges previous LC-MS/MS reports. J Chromatogr B 877:2895-2908
138. Tsikas D, Zoerner AA, Mitschke A, Gutzki FM (2009c) Nitro-fatty acids occur in human plasma in the picomolar range: a targeted nitro-lipidomics GC-MS/MS study. Lipids 44:855-865
139. Ulrich M, Petre A, Youhnovski N, Prömm F, Schirle M, Schumm M, Pero RS, Doyle A, Checkel J, Kita H, Thiyagarajan N, Acharya KR, Schmid-Grendelmeier P, Simon HU, Schwarz H, Tsutsui M, Shimokawa H, Bellon G, Lee JJ, Przybylski M, Döring G (2008) Post-translational tyrosine nitration of eosinophil granule toxins mediated by eosinophil peroxidase. J Biol Chem 283:28629-28640
140. Uppu RM, Squadrito GL, Pryor WA (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch Biochem Biophys 327:335-343 (Pubitemid 26086587)
141. van der Vliet A, t Hoen PAC, Wong PSY, Bast A, Cross CE (1998) Formation of S-nitrosothiols via direct nucleophilic nitrosation of thiols by peroxynitrite with elimination of hydrogen peroxide. J Biol Chem 273:30255-30262 (Pubitemid 28545492)
142. Van Eeckhaut A, Lanckmans K, Sarre S, Smolders I, Michotte Y (2009) Validation of bioanalytical LC-MS/MS assays: Evaluation of matrix effects. J Chromatogr B 877:2198-2207
143. Wayenberg JL, Ransy V, Vermeylen D, Damis E, Bottari SP (2009) Nitrated plasma albumin as a marker of nitrative stress and neonatal encephalopathy in perinatal asphyxia. Free Radic Biol Med 47:975-982
144. Webster RP, Macha S, Brockman D, Myatt L (2006a) Peroxynitrite treatment in vitro disables catalytic activity of recombinant p38 MAPK. Proteomics 6:4838-4844 (Pubitemid 44369063)
145. Webster RP, Brockman D, Myatt L (2006b) Nitration of p38 MAPK in the placenta: association of nitration with reduced catalytic activity of p38 MAPK in pre-eclampsia. Mol Hum Reprod 12:677-685 (Pubitemid 44605600)
146. Yan LJ (2009) Analysis of oxidative modification of proteins. Curr Protoc Protein Sci. Chapter 14:Unit14.4
147. Yi D, 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 (Pubitemid 34521245)
148. Zhang H, Squadrito GL, Uppu RM, Lemercier JN, Cueto R, Pryor WA (1997) Inhibition of peroxynitrite-mediated oxidation of glutathione by carbon dioxide. Arch Biochem Biophys 339:183-189 (Pubitemid 27199768)
149. Zou MH, Martin C, Ulrich V (1997) Tyrosine nitration as a mechanism of selective inactivation of prostacyclin synthase by peroxynitrite. J Biol Chem 378:707-713 (Pubitemid 27361864)