Kinetic analysis of the role of histidine chloramines in hypochlorous acid mediated protein oxidation

Biochemistry

Volumn 44, Issue 19, 2005, Pages 7378-7387

  Pattison, David I ^a   Davies, Michael J ^a  

^a HEART RESEARCH INSTITUTE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CELLS; DISEASES; ENZYME KINETICS; HEALTH CARE; HEALTH RISKS; RATE CONSTANTS; REACTION KINETICS; ULTRAVIOLET RADIATION;

ANTIBACTERIAL EFFECTS; CHLORAMINES; HUMAN DISEASES; OXIDANTS;

AMINO ACIDS;

4 IMIDAZOLEACETIC ACID; AMIDE; CYSTEINE; HISTIDINE; HYPOCHLOROUS ACID; LYSINE; METHIONINE; N ALPHA ACETYL HISTIDINE; OXIDIZING AGENT; TOSYLCHLORAMIDE SODIUM; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; DISULFIDE BOND; FLOW KINETICS; OXIDATION; PRIORITY JOURNAL; PROTEIN MODIFICATION; ULTRAVIOLET SPECTROSCOPY;

6-AMINOCAPROIC ACID; AMIDES; AMINES; ARGININE; CHLORAMINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCINE; HISTIDINE; HYPOCHLOROUS ACID; IMIDAZOLES; KINETICS; LYSINE; OLIGOPEPTIDES; OXIDATION-REDUCTION; PROTEIN CONFORMATION; TYROSINE;

EID: 18544368511     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0474665     Document Type: Article

References (40)

1. Zgliczynski, J. M., Stelmaszynska, T., Ostrowski, W., Naskalski, J., and Sznajd, J. (1968) Myeloperoxidase of human leukaemic leucocytes. Oxidation of amino acids in the presence of hydrogen peroxide, Eur. J. Biochem. 4, 540-547.
2. Morris, J. C. (1967) Kinetics of reactions between aqueous chlorine and nitrogen compounds, in Principles and Applications of Water Chemistry (Faust, E. D., and Hunter, J. V., Eds.) pp 23-53, John Wiley and Sons, New York.
3. Klebanoff, S. J. (1999) Myeloperoxidase, Proc. Assoc. Am. Physicians 111, 383-389.
4. Hoy, A., Leininger-Muller, B., Kutter, D., Siest, G., and Visvikis, S. (2002) Growing significance of myeloperoxidase in non-infectious diseases, Clin. Chem. Lab. Med. 40, 2-8.
5. Malle, E., Buch, T., and Grone, H.-J. (2003) Myeloperoxidase in kidney disease, Kidney Int. 64, 1956-1967.
6. Podrez, E. A., Abu-Soud, H. M., and Hazen, S. L. (2000) Myeloperoxidase-generated oxidants and atherosclerosis, Free Radical Biol. Med. 28, 1717-1725.
7. Zhang, R., Brennan, M. L., Fu, X., Aviles, R. J., Pearce, G. L., Penn, M. S., Topol, E. J., Sprecher, D. L., and Hazen, S. L. (2001) Association between myeloperoxidase levels and risk of coronary artery disease, J. Am. Med. Assoc. 286, 2136-2142.
8. Weitzman, S. A., and Gordon, L. I. (1990) Inflammation and cancer: role of phagocyte-generated oxidants in carcinogenesis, Blood 76, 655-663.
9. van der Vliet, A., Nguyen, M. N., Shigenaga, M. K., Eiserich, J. P., Marelich, G. P., and Cross, C. E. (2000) Myeloperoxidase and protein oxidation in cystic fibrosis, Am. J. Physiol. Lung Cell. Mol. Physiol. 279, L537-L546.
10. Hawkins, C. L., Pattison, D. I., and Davies, M. J. (2003) Hypochlorite-induced oxidation of amino acids, peptides and proteins, Amino Acids 25, 259-274.
11. Armesto, X. L., Canle, M., Garcia, M. V., and Santaballa, J. A. (1998) Aqueous chemistry of N-halo-compounds, Chem. Soc. Rev. 27, 453-460.
12. Winterbourn, C. C. (1985) Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant to hypochlorite, Biochim. Biophys. Acta 840, 204-210.
13. Pattison, D. I., and Davies, M. J. (2001) Absolute rate constants for the reaction of hypochlorous acid with protein side-chains and peptide bonds, Chem. Res. Toxicol. 14, 1453-1464.
14. Armesto, X. L., Canle, M., Fernandez, M. I., Garcia, M. V., and Santaballa, J. A. (2000) First steps in the oxidation of sulfur-containing amino acids by hypohalogenation: very fast generation of intermediate sulfenyl halides and halosulfonium cations, Tetrahedron 56, 1103-1109.
15. Folkes, L. K., Candeias, L. P., and Wardman, P. (1995) Kinetics and mechanisms of hypochlorous acid reactions, Arch. Biochem. Biophys. 323, 120-126.
16. Thomas, E. L., Grisham, M. B., and Jefferson, M. M. (1986) Preparation and characterization of chloramines, Methods Enzymol. 132, 569-585.
17. Prutz, W. A. (1998) Reactions of hypochlorous acid with biological substrates are activated catalytically by tertiary amines, Arch. Biochem. Biophys. 357, 265-273.
18. Prutz, W. A. (1998) Interactions of hypochlorous acid with pyrimidine nucleotides, and secondary reactions of chlorinated pyrimidines with GSH, NADH, and other substrates, Arch. Biochem. Biophys. 349, 183-191.
19. Peskin, A. V., Midwinter, R. G., Harwood, D. T., and Winterbourn, C. C. (2004) Chlorine transfer between glycine, taurine and histamine: reaction rates and impact on cellular reactivity, Free Radical Biol. Med. 37, 1622-1630.
20. Peskin, A. V., and Winterbourn, C. C. (2001) Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate, Free Radical Biol. Med. 30, 572-579.
21. Peskin, A. V., and Winterbourn, C. C. (2003) Histamine chloramine reactivity with thiol compounds, ascorbate, and methionine and with intracellular glutathione, Free Radical Biol. Med. 35, 1252-1260.
22. Hazen, S. L., d'Avignon, A., Anderson, M. A., Hsu, F. F., and Heinecke, J. W. (1998) Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize α-amino-acids to a family of reactive aldehydes, J. Biol. Chem. 273, 4997-5005.
23. Hawkins, C. L., and Davies, M. J. (1998) Reaction of HOCl with amino acids and peptides: EPR evidence for rapid rearrangement and fragmentation reactions of nitrogen-centered radicals, J. Chem. Soc., Perkin Trans. 2, 1937-1945.
24. Hawkins, C. L., and Davies, M. J. (1998) Hypochlorite-induced damage to proteins: formation of nitrogen-centred radicals from lysine residues and their role in protein fragmentation, Biochem. J. 332, 617-625.
25. Hawkins, C. L., Rees, M. D., and Davies, M. J. (2002) Superoxide radicals can act synergistically with hypochlorite to induce damage to proteins, FEBS Lett. 510, 41-44.
26. Domigan, N. M., Charlton, T. S., Duncan, M. W., Winterbourn, C. C., and Kettle, A. J. (1995) Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils, J. Biol. Chem. 270, 16542-16548.
27. Bergt, C., Fu, X., Huq, N. P., Kao, J., and Heinecke, J. W. (2004) Lysine residues direct the chlorination of tyrosines in YXXK motifs of apolipoprotein A-I when hypochlorous acid oxidizes HDL, J. Biol. Chem. 279, 7856-7866.
28. Hsu, Y.-C. (1964) Resistance of infectious RNA and transforming DNA to iodine which inactivates f2 phage and cells, Nature 203, 152-153.
29. Vissers, M. C. M., Lee, W. G., and Hampton, M. B. (2001) Regulation of apoptosis by vitamin C: specific protection of the apoptotic machinery against exposure to chlorinated oxidants, J. Biol. Chem. 276, 46835-46840.
30. Thomas, E. L., Grisham, M. B., and Jefferson, M. M. (1986) Cytotoxicity of chloramines, Methods Enzymol. 132, 585-593.
31. Prutz, W. A. (1999) Consecutive halogen transfer between various functional groups induced by reaction of hypohalous acids: NADH oxidation by halogenated amide groups, Arch. Biochem. Biophys. 371, 107-114.
32. Pattison, D. I., Hawkins, C. L., and Davies, M. J. (2003) Hypochlorous acid mediated oxidation of lipid components and antioxidants present in low density lipoproteins: absolute rate constants, product analysis and computational modeling, Chem. Res. Toxicol. 16, 439-449.
33. Morris, J. C. (1966) The acid ionization constant of HOCl from 5°C to 35°C, J. Phys. Chem. 70, 3798-3805.
34. Pattison, D. I., and Davies, M. J. (2004) Kinetic analysis of the reactions of hypobromous acid with protein components: implications for cellular damage and use of 3-bromotyrosine as a marker of oxidative stress, Biochemistry 43, 4799-4809.
35. Hunt, S. (1984) Halogenated tyrosine derivatives in invertebrate scleroproteins: isolation and identification, Methods Enzymol. 107, 413-438.
36. Prutz, W. A., Kissner, R., Koppenol, W. H., and Ruegger, H. (2000) On the irreversible destruction of reduced nicotinamide nucleotides by hypohalous acids, Arch. Biochem. Biophys. 380, 181-191.
37. Fu, X., Kao, J. L. F., Bergt, C., Kassim, S. Y., Huq, N. P., d'Avignon, A., Parks, W. C., Mecham, R. P., and Heinecke, J. W. (2004) Oxidative cross-linking of tryptophan to glycine restrains matrix metalloproteinase activity: specific structural motifs control protein oxidation, J. Biol. Chem. 279, 6209-6212.
38. Wright, C. D., and Low, J. E. (1989) Formation of chloramine derivatives of histamine: role of histamine chloramines in bronchoconstriction, Biochem. Biophys. Res. Commun. 165, 1018-1026.
39. Fu, S., Wang, H., Davies, M. J., and Dean, R. T. (2000) Reaction of hypochlorous acid with tyrosine and peptidyl-tyrosyl residues gives dichlorinated and aldehydic products in addition to 3-chlorotyrosine, J. Biol. Chem. 275, 10851-10857.
40. Nightingale, Z. D., Lancha, A. H., Jr., Handelman, S. K., Dolnikowski, G. G., Busse, S. C., Dratz, E. A., Blumberg, J. B., and Handelman, G. J. (2000) Relative reactivity of lysine and other peptide-bound amino acids to oxidation by hypochlorite, Free Radical Biol. Med. 29, 425-433.