Lactoperoxidase-catalyzed oxidation of melanin by reactive nitrogen species derived from nitrite (NO2-): An EPR study

Free Radical Biology and Medicine

Volumn 25, Issue 2, 1998, Pages 208-216

  Reszka, Krzysztof J ^a   Matuszak, Zenon ^a   Chignell, Colin F ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

EPR; Free radical; Lactoperoxidase; Melanin; Nitrite; Nitrogen dioxide radical

Indexed keywords

DOPA; HYDROGEN PEROXIDE; LACTOPEROXIDASE; MELANIN; NITRITE; NITROGEN; NITROGEN DIOXIDE; PEROXIDASE; SEMIQUINONE;

ARTICLE; CELL TRANSFORMATION; ELECTRON SPIN RESONANCE; ENZYME ANALYSIS; METAL BINDING; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROPHOTOMETRY;

CATALYSIS; DIHYDROXYPHENYLALANINE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HYDROGEN PEROXIDE; LACTOPEROXIDASE; MELANINS; MODELS, CHEMICAL; NITRITES; NITROGEN DIOXIDE; OXIDATION-REDUCTION;

EID: 0032527947     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00058-6     Document Type: Article

References (44)

1. Jimbow K., Fitzpatrick T. B., Quevedo W. C. Jr. Formation, chemical composition and function of melanin pigments. Matoltsy A. G. Biology of the integument, vol. 2. 1984;278-292 Springer, New York.
2. Nordlund J. J., Abdel-Malek Z. A., Boissy R. E., Rheins L. A. Pigment cell biology an historical review . J. Invest. Dermatol. (Suppl.). 92:1989;53S-60S.
3. Tsukamoto K., Palumbo A., D'Ischia M., Hearing V. J., Prota G. 5,6-Dihydroxyindole-2-carboxylic acid is incorporated in mammalian melanin. Biochem. J. 286:1992;491-495.
4. Sealy R. C. Free radicals in melanin formation, structure and reactions. Armstrong D., Sohal R. S., Cutler R. G. C., Slater T. R. Free radicals in molecular biology, aging, and disease. 1984;67-76 Raven Press, New York.
5. Reszka J., Jimbow K. Electron donor and acceptor properties of melanin pigments in the skin. Fuchs J., Packer L. Oxidative stress in dermatology. 1993;287-320 Marcel Dekker, Inc. New York.
6. Chauffe L., Windle J. J., Friedman M. Electron spin resonance study of melanin treated with reducing agents. Biophys. J. 15:1975;565-571.
7. Crippa P. R., Mazzini A., Salmelli D. Oxidation of NADH by melanin effect of UV light and copper ions . Physiol. Chem. Phys. 11:1979;491-499.
8. Oniki T., Takahama U. Effect of redox reagents on ESR line shape of synthetic melanins. Bull. Chem. Soc. Jpn. 65:1992;6-13.
9. Felix C. C., Hyde J. S., Sarna T., Sealy R. C. Interactions of melanin with metal ions. Electron spin resonance evidence for chelate complexes of metal ions with free radicals. J. Am. Chem. Soc. 100:1978;3922-3926.
10. Sarna T., Pilas B., Land E. J., Truscott T. G. Interaction of radicals from water radiolysis with melanin. Biochim. Biophys. Acta. 833:1986;162-167.
11. Korytowski W., Kalyanaraman B., Menon I. A., Sarna T., Sealy R. C. Reaction of superoxide anions with melanins Electron spin resonance and spin trapping studies . Biochim. Biophys. Acta. 882:1986;145-153.
12. Pilas B., Sarna T., Kalyanaraman B., Swartz H. M. The effect of melanin on iron associated decomposition of hydrogen peroxide. Free Radic. Biol. Med. 4:1988;285-293.
13. Bustamante J., Bredeston L., Malanga G., Mordoh J. Role of melanin as a scavenger of active oxygen species. Pigment Cell Res. 6:1993;348-353.
14. Korytowski W., Sarna T., Zareba M. Antioxidant action of neuromelanin The mechanism of inhibitory effect on lipid peroxidation . Arch. Biochem. Biophys. 319:1995;142-148.
15. Dong Z., Staroselsky A. H., Qi X., Xie K., Fidler I. J. Inverse correlation between expression of inducible nitric oxide synthase activity and production of metastasis in K-1735 murine melanoma cells. Cancer Res. 54:1994;789-793.
16. Joshi M., Strandhoy J., White W. L. Nitric oxide synthase activity is up-regulated in melanoma cell lines A potential mechanism for metastases formation . Melanoma Res. 6:1996;121-126.
17. Romero-Graillet C., Aberdam E., Clement M., Ortonne J. P., Ballotti R. Nitric oxide produced by ultraviolet-irradiated keratinocytes stimulates melanogenesis. J. Clin. Invest. 99:1997;635-642.
18. Weller R., Pattullo S., Smith L., Golden M., Ormerod A., Benjamin N. Nitric oxide is generated on the skin surface by reduction of sweat nitrate. J. Invest. Dermatol. 107:1996;327-331.
19. de la Breteche M.-L., Servy C., Lenfant M., Ducrocq C. Nitration of catecholamines with nitrogen oxides in mild conditions. Tetrahed. Lett. 35:1994;7231-7232.
20. Coombes R. G., Diggle A. W., Kempsell S. P. The mechanism of nitration of phenol and 4-methylphenol by nitrogen dioxide in solution. Tetrahed. Lett. 35:1994;6373-6376.
21. Kohler H., Jenzer H. Interaction of lactoperoxidase with hydrogen peroxide. Free Radic. Biol. Med. 6:1989;323-339.
22. Metodiewa D., Reszka K., Dunford H. B. Evidence for a peroxidatic oxidation of norepinephrine, a catecholamine, by lactoperoxidase. Biochem. Biophys. Res. Commun. 160:1989;1183-1188.
23. Metodiewa D., Reszka K., Dunford H. B. Oxidation of the substituted catechols dihydroxyphenylalanine methyl ester and trihydroxyphenylalanine by lactoperoxidase and its compounds. Arch. Biochem. Biophys. 274:1989;601-608.
24. Metodiewa D., Dunford H. B. Involvement of lactoperoxidase in the peroxidative degradation of serotonin A potential pathway for indolaminergic melanin formation . Biochem. Int. 23:1991;183-191.
25. Dunford R., Land E. J., Rozanowska M., Sarna T., Truscott T. G. Interaction of melanin with carbon- and oxygen centered radicals from methanol and ethanol. Free Radic. Biol. Med. 19:1995;735-740.
26. Paul K.-G., Ohlsson P.-I. The chemical structure of lactoperoxidase. Pruitt K. M., Tenovuo J. O. The lactoperoxidase system. Chemistry and biological significance. 1985;15-29 Mercel Dekker Inc. New York.
27. Hu S., Treat R. W., Kincaid J. R. Distinct heme active-site structure in lactoperoxidase revealed by resonance Raman spectroscopy. Biochemistry. 32:1993;10125-10130.
28. Reszka K. J., Bilski P., Chignell C. F. EPR and spin trapping investigations of nitric oxide (NO) from UV irradiated nitrite anions in alkaline aqueous solutions. J. Am. Chem. Soc. 118:1996;8719-8720.
29. Chance B. The kinetics and stoichiometry of the transition from the primary to the secondary peroxidase complexes. Arch. Biochem. Biophys. 41:1952;416-424.
30. Roman R., Dunford H. B. Studies on horseradish peroxidase. XII. A kinetic study of the oxidation of sulfite and nitrite by compounds I and II. Can. J. Chem. 51:1973;588-596.
31. Klebanoff S. J. Reactive nitrogen intermediates and antimicrobial activity Role of nitrite . Free Radic. Biol. Med. 14:1993;351-360.
32. Shibata H., Kono Y., Yamashita S., Sawa Y., Ochiai H., Tanaka K. Degradation of chlorophyll by nitrogen dioxide generated from nitrite by the peroxidase reaction. Biochim. Biophys. Acta. 1230:1995;45-50.
33. Van der Vliet A., Eiserich J. P., Halliwell B., Cross C. E. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. J. Biol. Chem. 272:1997;7617-7625.
34. Prutz W. A., Monig H., Butler J., Land E. J. Reactions of nitrogen dioxide in aqueous model systems oxidation of tyrosine units in peptides and proteins . Arch. Biochem. Biophys. 243:1985;125-134.
35. 2. Toxicology. 89:1994;193-216.
36. Halliwell B., Hu M-L., Louie S., Duvall T. R., Tarkington B. K., Motchnik P., Cross C. E. Interaction of nitrogen dioxide with human plasma. FEBS Lett. 313:1992;62-66.
37. Forni, L. G.; Mora-Arellano, V. O.; Packer, J. E.; Willson, R. L. Nitrogen dioxide and related free radicals: electron-transfer reactions with organic compounds in solutions containing nitrite or nitrate. J. Chem. Soc. Perkin Trans.II:1-6; 1986.
38. Stanbury D. M. Reduction potentials involving inorganic free radicals in aqueous solution. Adv. Inorg. Chem. 33:1989;69-138.
39. Jovanovic S. V., Steenken S., Simic M. G. One-electron reduction potentials of 5-indoloxyl radicals, a pulse radiolysis and laser photolysis study. J. Phys. Chem. 94:1990;3583-3588.
40. Jovanovic, S. V.; Simic, M. G. Redox properties of oxy and antioxidant radicals. In: Simic, M. G.; Taylor, K. A.; Ward, J. F.; von Sonntag, C. eds. Oxygen radicals in biology and medicine. New York: Plenum Press; 1988:115-121.
41. Steenken S., Neta P. One-electron redox potentials of phenols. Hydroxy- and aminoxyphenols and related compounds of biological interest. J. Phys. Chem. 86:1982;3661-3667.
42. Xie K., Huang S., Dong Z., Juang S-H., Gutman M., Xie Q-W., Nathan C., Fidler I. J. Transfection with the inducible nitric oxide synthase gene suppresses tumorigenicity and abrogates metastasis by K-1735 Murine melanoma cells. J. Exp. Med. 181:1995;1333-1343.
43. Xie K., Dong Z., Fidler I. J. Activation of nitric oxide synthase gene for inhibition of cancer metastasis. J. Leukoc. Biol. 59:1996;797-803.
44. Wang Y., Casadevall A. Susceptibility of melanized and nonmelanized Cryptococcus neoformans to nitrogen- and oxygen-derived oxidants. Infection Immun. 62:1994;3004-3007.