Mechanism of inhibition of melanogenesis by hydroquinone.

作者: Anna Palumbo , Marco d'Ischia , Giovanna Misuraca , Giuseppe Prota

DOI: 10.1016/0304-4165(91)90186-K

关键词:

摘要: Hydroquinone (HQ) is one of the most effective inhibitors melanogenesis in vitro and vivo, widely used for treatment melanosis other hyperpigmentary disorders. In an attempt to get some insight into molecular mechanism depigmenting action, which still very poorly understood, we have investigated effect HQ on tyrosinase catalysed conversion tyrosine melanin. Incubation 0.5 mM with 0.07 U/ml phosphate buffer at pH 6.8 presence led no detectable melanin formation, due preferential oxidation respect (HPLC evidence). Kinetic investigations showed that a poorer substrate than tyrosine; yet, it may be effectively oxidised owing generation catalytic amounts dopa acting as cofactor tyrosinase. Product analysis predominant formation early stages hydroxybenzoquinone (HBQ), arising from enzymic hydroxylation subsequent HQ, along lower benzoquinone (BQ). These results suggest activity partly related ability compound act alternate tyrosinase, thereby competing active melanocytes.

参考文章(13)
Cleveland R. Denton, Aaron Bunsen Lerner, Thomas B. Fitzpatrick, Inhibition of Melanin Formation by Chemical Agents Journal of Investigative Dermatology. ,vol. 18, pp. 119- 135 ,(1952) , 10.1038/JID.1952.16
Howard S. Mason, The chemistry of melanin; mechanism of the oxidation of dihydroxyphenylalanine by tyrosinase. Journal of Biological Chemistry. ,vol. 172, pp. 83- 99 ,(1948) , 10.1016/S0021-9258(18)35614-X
V J Hearing, T M Ekel, Mammalian tyrosinase. A comparison of tyrosine hydroxylation and melanin formation Biochemical Journal. ,vol. 157, pp. 549- 557 ,(1976) , 10.1042/BJ1570549
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
P. A. Riley, Mechanism of pigment‐cell toxicity produced by hydroxyanisole The Journal of Pathology. ,vol. 101, pp. 163- 169 ,(1970) , 10.1002/PATH.1711010211
W Chavin, E. Jelonek, A. Reed, L. Binder, Survival of mice receiving melanoma transplants is promoted by hydroquinone Science. ,vol. 208, pp. 408- 410 ,(1980) , 10.1126/SCIENCE.7367868
Frank C. Spencer, Successful Replacement of a Thrombosed Mitral Ball-Valve Prosthesis JAMA: The Journal of the American Medical Association. ,vol. 194, pp. 1249- 1251 ,(1965) , 10.1001/JAMA.1965.03090240083031
Kathryn B Penney, Christopher J Smith, John C Allen, Depigmenting Action of Hydroquinone Depends on Disruption of Fundamental Cell Processes Journal of Investigative Dermatology. ,vol. 82, pp. 308- 310 ,(1984) , 10.1111/1523-1747.EP12260588
S. PASSI, M. NAZZARO-PORRO, Molecular basis of substrate and inhibitory specificity of tyrosinase: phenolic compounds. British Journal of Dermatology. ,vol. 104, pp. 659- 665 ,(1981) , 10.1111/J.1365-2133.1981.TB00752.X
Aaron Bunsen Lerner, Thomas B. Fitzpatrick, BIOCHEMISTRY OF MELANIN FORMATION Physiological Reviews. ,vol. 30, pp. 91- 126 ,(1950) , 10.1152/PHYSREV.1950.30.1.91