Kinetics of oxidation of serotonin by myeloperoxidase compounds I and II

Biochemistry and Cell Biology

Volumn 77, Issue 5, 1999, Pages 449-457

  Dunford, H Brian ^a   Hsuanyu, Yuchiong ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Blood platelets; Chloride; Competition of serotonin; Myeloperoxidase; Neutrophils; Serotonin oxidation

Indexed keywords

CHLORIDE; ENZYME; FREE RADICAL; LIPOPROTEIN; MYELOPEROXIDASE; SEROTONIN;

ARTICLE; CHEMICAL REACTION KINETICS; COMPETITION; ENZYME INACTIVATION; LIPID OXIDATION; NEUTROPHIL; OXIDATION; PH; REACTION ANALYSIS; REDUCTION; SPECTROSCOPY; THROMBOCYTE;

EID: 0033429040     PISSN: 08298211     EISSN: None     Source Type: Journal    
DOI: 10.1139/o99-052     Document Type: Article

References (37)

1. Albrich, J.M., McCarthy, C.A., and Hurst, J.K. 1981. Biological reactivity of hypochlorous acid: implications for microbicidal mechanisms of leukocyte myeloperoxidase. Proc. Natl. Acad. Sci. U.S.A. 78: 210-214.
2. Atkinson, T.P., White, M.V., and Kaliner, M.A. 1992. Histamine and serotonin. In Inflammation. Basic principles and clinical correlates. 2nd ed. Edited by J.I Gallin, I.M. Goldstein, and R. Snyderman. Raven Press, New York. pp. 193-209.
3. Clark, R.A., and Klebanoff, S.J. 1979. Myeloperoxidase-mediated platelet release reaction. J. Clin. Invest. 63: 177-183.
4. Clark, R.A., and Klebanoff, S.J. 1980. Neutrophil-platelet interaction mediated by myeloperoxidase and hydrogen peroxide. J. Immunol. 124: 399-405.
5. Cotton, M.L., and Dunford, H.B. 1973. Studies on horseradish peroxidase. XI. Nature of compounds I and II as determined from the kinetics of the oxidation of ferrocyanide. Can. J. Chem. 51: 582-587.
6. Dunford, H.B. 1991. Horseradish peroxidase: structure and kinetic properties. In Peroxidases in chemistry and biology. Vol. II. Edited by J. Everse and M.B. Grisham. CRC Press, Boca Raton, Fla. pp. 1-24.
7. Filippini, G.A., Costa, C.V.L., and Bertazzo, A., 1996. Recent advances in tryptophan research. Tryptophan and serotonin pathways. Plenum, New York.
8. Golino, P., Piscione, F., Willerson, J.T., et al. 1991. Divergent effects of serotonin on coronary-artery dimensions and blood flow in patients with coronary athersclerosis and control patients. N. Engl. J. Med. 324: 641-648.
9. Harrison, J.E., and Schultz, J. 1976. Studies on the chlorinating activity of myeloperoxidase. J. Biol. Chem. 251: 1371-1374.
10. Hurst, J.K., and Barrette, W.C., Jr. 1989. Leukocytic oxygen activation and microbicidal oxidative toxins. Crit. Rev. Biochem. Mol. Biol. 24: 271-328.
11. 2. J. Neural Transm. Suppl. 32: 249-257.
12. Jensen, M.S., and Bainton, D.F. 1973. Temporal changes in pH within the phagocytic vacuole of the polymorphonuclear neutrophilic leukocyte. J. Cell Biol. 56: 379-388.
13. Klebanoff, S.J., and Clark, R.A. 1978. The neutrophil: function and clinical disorders. North-Holland Publishing Co., Amsterdam.
14. Marquez, L.A., and Dunford, H.B. 1994. Chlorination of taurine by myeloperoxidase. Kinetic evidence for an enzyme-bound intermediate. J. Biol. Chem. 269: 7950-7956.
15. Marquez, L.A., and Dunford, H.B. 1995. Kinetics of oxidation of tyrosine and dityrosine by myeloperoxidase compounds I and II. Implications for lipoprotein peroxidation studies. J. Biol. Chem. 270: 30434-30440.
16. Marquez, L.A., Huang, J.T., and Dunford, H.B. 1994. Spectral and kinetic studies on the formation of myeloperoxidase compounds I and II: roles of hydrogen peroxide and superoxide. Biochemistry, 33: 1447-1454.
17. Martin, G.M., Benditt, E.P., and Eriksen, N. 1960. Enzymic oxidation of the indole nucleus of 5-hydroxytryptamine: properties of an enzyme in human serum and the products of oxidation. Arch. Biochem. Biophys. 90: 208-217.
18. McFadden, E.P., Clarke, J.G., Davies, G.J., Kashi, J.C., Haider, A.W., and Maseri, A. 1991. Effect of intracoronary serotonin on coronary vessels in patients with stable angina and patients with invariant angina. N. Engl. J. Med. 324: 648-654.
19. Metodiewa, D., and Dunford, H. B. 1991. Involvement of lactoperoxidase in the peroxidative degradation of serotonin: a potential pathway for indolaminergic melanin formation. Biochem. Internat. 23: 183-191.
20. Napolitano, A., d'Ischia, M., and Prota, G. 1988. A profile of the oxidation chemistry of 5-hydroxyindole under biomimetic conditions. Tetrahedron, 44: 7265-7270.
21. 2 solutions in the UV). Anal. Biochem. 49: 474-478.
22. Nelson, D.R., and Huggins, A.G. 1975. The interaction of 5-hydroxytryptamine and related hydroxyindoles with horseradish and mammalian peroxidase systems. Biochem. Pharmacol. 24: 181-192.
23. Oertling, W.A., Hoogland, H., Babcock, G.T., and Wever, R. 1988. Identification and properties of an oxoferryl structure in myeloperoxidase compound II. Biochemistry, 27: 5395-5400.
24. Perez-Reyes, E., and Mason, R.P. 1981. Characterization of the structure and reactions of free radicals from serotonin and related indoles. J. Biol. Chem. 256: 2427-2432.
25. Poulos, T.L., and Fenna, R.E. 1994. Peroxidases: structure, function and engineering. In Metals in biological systems. Vol. 30. Edited by H. Siegel. Marcel Dekker, New York. pp. 25-75.
26. Rapport, M.M., Green, A.A., and Page, I.H. 1948. Serum vasoconstrictor (serotonin). IV. Isolation and characterization. J. Biol. Chem. 176: 1243-1251.
27. Salman-Tabcheh, S., Guérin, M.-C., and Torreilles, J. 1996. Potential role of the peroxidase-dependent metabolism of serotonin in lowering the polymorphonuclear leukocyte bactericidal function. Free Radical Res. 24: 61-68.
28. Schultz, J., and Kaminker, K. 1962. Myeloperoxidase of the leukocyte of normal human blood. I. Content and localization. Arch. Biochem. Biophys. 96: 465-467.
29. Stelmaszynska, T., Kukovitz, E., Egger, G., and Schaur, R.J. 1992. Possible involvement of myeloperoxidase in lipid peroxidation. Int. J. Biochem. 23: 121-128.
30. Stoltz, J.F. 1985. Uptake and storage of serotonin by platelets. In Serotonin and the cardiovascular system. Edited by P.M. Vanhoutte. Raven Press, New York. pp. 37-42.
31. Svensson, B.E. 1989. Involvement of cysteine, serotonin and their analogues in peroxidase-oxidase reactions. Chem. Biol. Interactions, 70: 305-321.
32. Tobler, A., and Koeffler, H.P. 1991. Myeloperoxidase: localization, structure, and founction. In Blood cell biochemistry. Vol. 3. Edited by J.R. Harris. Plenum Publishing Co., New York. pp. 255-288.
33. Uemera, T., Shimazu, T., Miura, R., and Yamano, T. 1980. NADPH-dependent melanin pigment formation from 5-hydroxyindolealkylamines by hepatic and cerebral microsomes. Biochem. Biophys. Res. Commun. 93: 1074-1081.
34. Verbeuren, T.J. 1990. The distribution and biochemistry of 5-hydroxytryptamine in the cardiovascular system. In Cardiovascular pharmacology of 5-hydroxytryptamine. Edited by P.R. Saxena, D.I. Wallis, W. Wouters, and P. Bevan. Kluwer, Dordrecht. pp. 3-13.
35. 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.
36. Wrona, M.Z., and Dryhurst, G. 1987. Oxidation chemistry of 5-hydroxytryptamine. 1. Mechanism and products formed at micromolar concentrations. J. Org. Chem. 52: 2817-2825.
37. Wrona, M.Z., and Dryhurst, G. 1988. Further insights into the oxidation chemistry of 5-hydroxytryptamine. J. Pharmaceut. Sci. 77: 911-917.