Bleaching of melanin pigments. Role of copper ions and hydrogen peroxide in autooxidation and photooxidation of synthetic dopa-melanin.

作者: W Korytowski , T Sarna

DOI: 10.1016/S0021-9258(19)38362-0

关键词:

摘要: Bleaching of eumelanin has been studied in model systems consisting synthetic dopa-melanin and various concentrations hydrogen peroxide, molecular oxygen, copper(II) ions at neutral alkaline pH. The data show that pH, the dark, metal-ion-free melanin is very resistant to oxidation by peroxide. However, rate bleaching melanin, induced H2O2 significantly accelerated illumination from UVA-visible light. Bound-to-melanin also accelerates with efficiency dependent on concentration oxygen. It suggests possible involvement melanin-copper complexes Fenton-like processes. formation hydroxyl radicals during concluded basis electrochemical detection hydroxylation products salicylate used as OH scavenger. Redox conversion bound-to-melanin copper was monitored EPR spectroscopy direct measurement melanin-Cu(II) complexes. shown melanin-copper(I) were readily oxidized either oxygen or indicate a complex process two distinct stages, reversible hydroquinone moieties followed irreversible reactions monomers lead degradation polymer.

参考文章(29)
Robert A. Floyd, C.Ann Lewis, Peter K. Wong, [27] High-pressure liquid chromatography-electrochemical detection of oxygen free radicals Methods in Enzymology. ,vol. 105, pp. 231- 237 ,(1984) , 10.1016/S0076-6879(84)05030-8
B Halliwell, J M C Gutteridge, OXYGEN TOXICITY, OXYGEN RADICALS, TRANSITION METALS AND DISEASE Biochemical Journal. ,vol. 219, pp. 1- 14 ,(1984) , 10.1042/BJ2190001
George V. Buxton, Clive L. Greenstock, W. Phillips Helman, Alberta B. Ross, Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/⋅O− in Aqueous Solution Journal of Physical and Chemical Reference Data. ,vol. 17, pp. 513- 886 ,(1988) , 10.1063/1.555805
T.M. Florence, The production of hydroxyl radical from hydrogen peroxide Journal of Inorganic Biochemistry. ,vol. 22, pp. 221- 230 ,(1984) , 10.1016/0162-0134(84)85007-2
Shiu-Shin Chio, James S. Hyde, Roger C. Sealy, Paramagnetism in melanins: pH dependence Archives of Biochemistry and Biophysics. ,vol. 215, pp. 100- 106 ,(1982) , 10.1016/0003-9861(82)90283-1
B PILAS, T SARNA, B KALYANARAMAN, H SWARTZ, The effect of melanin on iron associated decomposition of hydrogen peroxide. Free Radical Biology and Medicine. ,vol. 4, pp. 285- 293 ,(1988) , 10.1016/0891-5849(88)90049-4
R. Sealy, J. Hyde, C. Felix, I. Menon, G Prota, Eumelanins and pheomelanins: characterization by electron spin resonance spectroscopy Science. ,vol. 217, pp. 545- 547 ,(1982) , 10.1126/SCIENCE.6283638
Giuseppe Prota, None, Progress in the chemistry of melanins and related metabolites Medicinal Research Reviews. ,vol. 8, pp. 525- 556 ,(1988) , 10.1002/MED.2610080405