Kinetics of 3-nitrotyrosine modification on exposure to hypochlorous acid

Free Radical Research

Volumn 48, Issue 11, 2014, Pages 1355-1362

  Curtis, M P ^a   Neidigh, J W ^a  

^a LOMA LINDA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

3 chlorotyrosine; Biomarker; Chloramine; Protein damage; Reactive species

Indexed keywords

3 NITROTYROSINE; AMINO ACID; AMINO ACID MIXTURE; CHLORAMINE DERIVATIVE; HYPOCHLOROUS ACID; REACTIVE NITROGEN SPECIES; TYROSINE DERIVATIVE; 3-NITROTYROSINE; BIOLOGICAL MARKER; PEPTIDE FRAGMENT; PEROXIDASE; TYROSINE;

ARTICLE; CHEMICAL REACTION KINETICS; CHLORINATION; CONJUGATE; EXPOSURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IN VIVO STUDY; LIMIT OF QUANTITATION; PEPTIDE SYNTHESIS; PROTEIN DEPLETION; PROTEIN MODIFICATION; PROTEIN PURIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY; ULTRAVIOLET SPECTROSCOPY; ANALOGS AND DERIVATIVES; CHEMISTRY; KINETICS; METABOLISM;

BIOLOGICAL MARKERS; CHLORAMINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; HYPOCHLOROUS ACID; KINETICS; PEPTIDE FRAGMENTS; PEROXIDASE; REACTIVE NITROGEN SPECIES; TYROSINE;

EID: 84907540584     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2014.954110     Document Type: Article

References (35)

1. Ohshima H, Tatemichi M, Sawa T. Chemical basis of infl ammation-induced carcinogenesis. Archives of Biochemistry and Biophysics 2003; 417: 3-11.
2. Halliwell B. Oxidative stress and neurodegeneration: where are we now? J Neurochem 2006; 97: 1634-1658.
3. Stocker R, Keaney JF. Role of oxidative modifi cations in atherosclerosis. Physiol Rev 2004; 84: 1381-1478.
4. Dedon PC, Tannenbaum SR. Reactive nitrogen species in the chemical biology of infl ammation. Arch Biochem Biophys 2004; 423: 12-22.
5. Hawkins CL, Pattison DI, Davies MJ. Hypochlorite-induced oxidation of amino acids, peptides and proteins. Amino Acids 2003; 25: 259-274.
6. van der Vliet A, Eiserich JP, Kaur H, Cross CE, Halliwell B. Nitrotyrosine as biomarker for reactive nitrogen species. Methods Enzymol 1996; 269: 175-184.
7. Gaut JP, Byun J, Tran HD, Heinecke JW. Artifact-free quantifi cation 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 2002; 300: 252-259.
8. Whiteman M, Halliwell B. Loss of 3-nitrotyrosine on exposure to hypochlorous acid: Implications for the use of 3-nitrotyrosine as a bio-marker in vivo. Biochem Biophys Res Commun 1999; 258: 168-172.
9. Abu-Soud HM, Hazen SL. Nitric oxide is a physiological substrate for mammalian peroxidases. J Biol Chem 2000; 275: 37524-37532.
10. Eiserich JP, Hristova M, Cross CE, Jones AD, Freeman BA, Halliwell B, van der Vliet A. Formation of nitric oxide derived infl ammatory oxidants by myeloperoxidase in neutrophils. Nature 1998; 391: 393-397.
11. Evans TJ, Buttery LDK, Carpenter A, Springall DR, Polak JM, Cohen J. Cytokine-treated human neutrophils contain inducible nitric oxide synthase that produces nitration of ingested bacteria. Proc Natl Acad Sci U S A 1996; 93: 9553-9558.
12. Cedergren J, Follin P, Forslund T, Lindmark M, Sungqvist T, Skogh T. Inducible nitric oxide synthase (NOS II) is constitutive in human neutrophils. Apmis 2003; 111: 963-968.
13. Zheng LM, Nukuna B, Brennan ML, Sun MJ, Goormastic M, Settle M, et al. Apolipoprotein A-I is a selective target for myeloperoxidase-catalyzed oxidation and functional impairment in subjects with cardiovascular disease. J Clin Invest 2004; 114: 529-541.
14. Hensley K, Maidt ML, Yu ZQ, Sang H, Markesbery WR, Floyd RA. Electrochemical analysis of protein nitrotyrosine and dityrosine in the Alzheimer brain indicates region-specifi c accumulation. J Neurosci 1998; 18: 8126-8132.
15. Green PS, Mendez AJ, Jacob JS, Crowley JR, Growdon W, Hyman BT, Heinecke JW. Neuronal expression of myeloperoxidase is increased in Alzheimer ' s disease. J Neurochem 2004; 90: 724-733.
16. Riordan JF, Sokolovs M, Vallee BL. Environmentally sensitive tyrosyl residues. Nitration with tetranitromethane. Biochemistry 1967; 6: 358-361.
17. Morris JC. Acid Ionization constant of Hocl from 5 to 35 degrees. J Phys Chem 1966; 70: 3798-3805.
18. Pattison DI, Davies MJ. Kinetic analysis of the role of histidine chloramines in hypochlorous acid mediated protein oxidation. Biochemistry 2005; 44: 7378-7387.
19. Curtis MP, Hicks AJ, Neidigh JW. Kinetics of 3-Chlorotyrosine formation and loss due to hypochlorous acid and chloramines. Chem Res Toxicol 2011; 24: 418-428.
20. Pattison DI, Davies MJ. Absolute rate constants for the reaction of hypochlorous acid with protein side chains and peptide bonds. Chem Res Toxicol 2001; 14: 1453-1464.
21. Fu SL, Wang HJ, Davies M, Dean R. Reactions of hypochlorous acid with tyrosine and peptidyl-tyrosyl residues give dichlorinated and aldehydic products in addition to 3-chlorotyrosine. J Biol Chem 2000; 275: 10851-10858.
22. Adam LC, Fabian I, Suzuki K, Gordon G. Hypochlorous acid decomposition in the Ph 5-8 region. Inorg Chem 1992; 31: 3534-3541.
23. Pattison DI, Hawkins CL, Davies MJ. Hypochlorous acidmediated protein oxidation: How important are chloramine transfer reactions and protein tertiary Structure? Biochemistry 2007; 46: 9853-9864.
24. Bergt C, Fu XY, Huq NP, Kao J, Heinecke JW. Lysine residues direct the chlorination of tyrosines in YXXK motifs of apolipoprotein A-I when hypochlorous acid oxidizes high density lipoprotein. J Biol Chem 2004; 279: 7856-7866.
25. Chapman ALP, Senthilmohan R, Winterbourn CC, Kettle AJ. Comparison of mono- and dichlorinated tyrosines with carbonyls for detection of hypochlorous acid modifi ed proteins. Arch Biochem Biophys 2000; 377: 95-100.
26. Kang JI, Neidigh JW. Hypochlorous acid damages histone proteins forming 3-chlorotyrosine and 3,5-dichlorotyrosine. Chem Res Toxicol 2008; 21: 1028-1038.
27. Gallard H, Von Gunten U. Chlorination of phenols: Kinetics and formation of chloroform. Environ Sci Technol 2002; 36: 884-890.
28. Heasley VL, Fisher AM, Herman EE, Jacobsen FE, Miller EW, Ramirez AM, et al. Investigations of the reactions of monochloramine and dichloramine with selected phenols: Examination of humic acid models and water contaminants. Environ Sci Technol 2004; 38: 5022-5029.
29. Domigan NM, Charlton TS, Duncan MW, Winterbourn CC, Kettle AJ. Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils. J Biol Chem 1995; 270: 16542-16548.
30. Peskin AV, Winterbourn CC. Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate. Free Radic Biol Med 2001; 30: 572-579.
31. Shao BH, Bergt C, Fu XY, Green P, Voss JC, Oda MN, et al. Tyrosine 192 in apolipoprotein A-I is the major site ofnitration and chlorination by myeloperoxidase, but only chlorination markedly impairs ABCA1-dependent cholesterol transport. J Biol Chem 2005; 280: 5983-5993.
32. Gunaydin H, Houk KN. Mechanisms of peroxynitritemediated nitration of tyrosine. Chem Res Toxicol 2009; 22: 894-898.
33. Jiao KS, Mandapati S, Skipper PL, Tannenbaum SR, Wishnok JS. Site-selective nitration of tyrosine in human serum albumin by peroxynitrite. Anal Biochem 2001; 293: 43-52.
34. Radi R. Protein tyrosine nitration: biochemical mechanisms and structural basis of functional eff ects. Acc Chem Res 2013; 46: 550-559.
35. Souza JM, Daikhin E, Yudkoff M, Raman CS, Ischiropoulos H. Factors determining the selectivity of protein tyrosine nitration. Arch Biochem Biophys 1999; 371: 169-178.