Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid

Brazilian Journal of Medical and Biological Research

Volumn 38, Issue 11, 2005, Pages 1575-1583

  Ximenes, V F ^a   Paino, I M M ^a   de Faria Oliveira, O M M ^a   da Fonseca, L M ^a   Brunetti, I L ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

Hypochlorous acid; Indole ring; Indole 3 acetic acid; Leukocytes; Melatonin; Myeloperoxidase

Indexed keywords

ASCORBIC ACID; BUFFER; HYPOCHLOROUS ACID; INDOLE; INDOLE DERIVATIVE; INDOLEACETIC ACID; INDOMETACIN; MELATONIN; MYELOPEROXIDASE; PHORBOL 13 ACETATE 12 MYRISTATE; PHOSPHATE; SODIUM CHLORIDE; SUPEROXIDE; TAURINE; TOSYLCHLORAMIDE SODIUM; TRYPTOPHAN;

ARTICLE; CELL ISOLATION; CELL VIABILITY; CHLORINATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LEUKOCYTE ACTIVATION; OXIDATION; PEROXIDATION;

EID: 27944458872     PISSN: 0100879X     EISSN: 1414431X     Source Type: Journal    
DOI: 10.1590/S0100-879X2005001100003     Document Type: Article

References (34)

1. Munn DH, Zhou M, Attwood JT et al. (1998). Prevention of allogeneic fetal rejection by tryptophan catabolism. Science, 281: 1191-1193.
2. Betten A, Dahlgren C, Hermodsson S et al. (2001). Serotonin protects NK cells against oxidatively induced functional inhibition and apoptosis. Journal of Leukocyte Biology, 70: 65-72.
3. Tan DX, Reiter RJ, Manchester LC et al. (2002). Chemical and physical properties and potential mechanisms: melatonin as a broad spectrum antioxidant and free radical scavenger. Current Topics in Medicinal Chemistry, 2: 181-197.
4. Reiter RJ, Calvo JR, Karbownik M et al. (2000). Melatonin and its relation to the immune system and inflammation. Annals of the New York Academy of Sciences, 917: 376-386.
5. Nauseef WM (2001). Contributions of myeloperoxidase to proinflammatory events: more than an antimicrobial system. International Journal of Hematology, 74: 125-133.
6. Baldus S, Heeschen C, Meinertz T et al. (2003). Myeloperoxidase serum levels predict risk in patients with acute coronary syndromes. Circulation, 108: 1440-1445.
7. Li JX, Pang YZ, Tang CS et al. (2004). Protective effect of taurine on hypochlorous acid toxicity to nuclear nucleoside triphosphatase in isolated nuclei from rat liver. World Journal of Gastroenterology, 10: 694-698.
8. Jerlich A, Fritz G, Kharrazi H et al. (2000). Comparison of HOCl traps with myeloperoxidase inhibitors in prevention of low density lipoprotein oxidation. Biochimica et Biophysica Acta, 1481: 109-118.
9. Brandolini L, Allegretti M, Berdini V et al. (2003). Carbocysteine lysine salt monohydrate (SCMC-LYS) is a selective scavenger of reactive oxygen intermediates (ROIs). European Cytokine Network, 14: 20-26.
10. Allegra M, Furtmuller PG, Regelsberger G et al. (2001). Mechanism of reaction of melatonin with human myeloperoxidase. Biochemical and Biophysical Research Communications, 282: 380-386.
11. Chapman AL, Winterbourn CC, Brennan SO et al. (2003). Characterization of non-covalent oligomers of proteins treated with hypochlorous acid. Biochemical Journal, 375: 33-40.
12. Ciz M & Lojek A (1997). Improved dextran preparation of human leucocytes for chemiluminescence analysis of the oxidative burst of polymorphonuclear cells. Clinical and Laboratory Haematology, 19: 49-51.
13. Costa M, Ximenes VF & Fonseca LM (2004). Hypochlorous acid inhibition by acetoacetate: implications on neutrophil functions. Biological and Pharmaceutical Bulletin, 27: 1183-1187.
14. Hallett MB, Cole C & Dewitt S (2003). Detection and visualization of oxidase activity in phagocytes. Methods in Molecular Biology, 225: 61-67.
15. Kettle AJ, Gedye CA & Winterbourn CC (1997). Mechanism of inactivation of myeloperoxidase by 4-aminobenzoic acid hydrazide. Biochemical Journal, 321: 503-508.
16. Mosmann T (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65: 55-63.
17. Dellegar SM, Murphy SA, Bourne AE et al. (1999). Identification of the factors affecting the rate of deactivation of hypochlorous acid by melatonin. Biochemical and Biophysical Research Communications, 257: 431-439.
18. Fu X, Kao JL, Bergt C et al. (2004). Oxidative cross-linking of tryptophan to glycine restrains matrix metalloproteinase activity: specific structural motifs control protein oxidation. Journal of Biological Chemistry, 279: 6209-6212.
19. Castro-Gamboa I & Castro O (2004). Iridoids from the aerial parts of Verbena littoralis (Verbenaceae). Phytochemistry, 65: 2369-2372.
20. Furtmuller PG, Obinger C, Hsuanyu Y et al. (2000). Mechanism of reaction of myeloperoxidase with hydrogen peroxide and chloride ion. European Journal of Biochemistry, 267: 5858-5864.
21. Spickett CM, Jerlich A, Panasenko OM et al. (2000). The reactions of hypochlorous acid, the reactive oxygen species produced by myeloperoxidase, with lipids. Acta Biochimica Polonica, 47: 889-899.
22. Domigan NM, Chariton TS, Duncan MW et al. (1995). Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils. Journal of Biological Chemistry, 270: 16542-16548.
23. Winterbourn CC, Vissers MC & Kettle AJ (2000). Myeloperoxidase. Current Opinion in Hematology, 7: 53-58.
24. Kato Y, Nagao A, Terao J et al. (2003). Inhibition of myeloperoxidase-catalyzed tyrosylation by phenolic antioxidants in vitro. Bioscience, Biotechnology, and Biochemistry, 67: 1136-1139.
25. Karasyova EI, Naumchik IV & Metelitza DI (2003). Activation of peroxidase-catalyzed oxidation of aromatic amines with 2-aminothiazole and melamine. Biochemistry, 68: 54-62.
26. Jantschko W, Furtmuller PG, Allegra M et al. (2002). Redox intermediates of plant and mammalian peroxidases: a comparative transient-kinetic study of their reactivity toward indole derivatives. Archives of Biochemistry and Biophysics, 398: 12-22.
27. Kettle AJ & Winterbourn CC (1991). Mechanism of inhibition of myeloperoxidase by anti-inflammatory drugs. Biochemical Pharmacology, 41: 1485-1492.
28. Neve J, Parij N & Moguilevsky N (2001). Inhibition of the myeloperoxidase chlorinating activity by non-steroidal anti-inflammatory drugs investigated with a human recombinant enzyme. European Journal of Pharmacology, 417: 37-43.
29. Berlin A, Canavesi A, Schiavon G et al. (1996). Electrooxidation products of methylindoles: Mechanisms and structures. Tetrahedron, 52: 7947-7960.
30. Candeias LP, Folkes LK, Porssa M et al. (1996). Rates of reaction of indoleacetic acids with horseradish peroxidase compound I and their dependence on the redox potentials. Biochemistry, 35: 102-108.
31. Marquez LA, Dunford HB & Van Wart H (1990). Kinetic studies on the reaction of compound II of myeloperoxidase with ascorbic acid: Role of ascorbic acid in myeloperoxidase function. Journal of Biological Chemistry, 265: 5666-5670.
32. Burner U, Obinger C, Paumann M et al. (1999). Transient and steady-state kinetics of the oxidation of substituted benzoic acid hydrazides by myeloperoxidase. Journal of Biological Chemistry, 274: 9494-9502.
33. de Melo MP, de Lima TM, Pithon-Curi TC et al. (2004). The mechanism of indole acetic acid cytotoxicity. Toxicology Letters, 148: 103-111.
34. Greco O, Rossiter S, Kanthou C et al. (2001). Horseradish peroxidase-mediated gene therapy: choice of prodrugs in oxic and anoxic tumor conditions. Molecular Cancer Therapeutics, 1: 151-160.