IFPCS presidential lecture: A chemist's view of melanogenesis

Pigment Cell Research

Volumn 16, Issue 3, 2003, Pages 230-236

  Ito, Shosuke ^a  

^a FUJITA HEALTH UNIVERSITY   (Japan)

Author keywords

5,6 dihydroxyindole; 5,6 dihydroxyindole 2 carboxylic acid; Cysteinyldopa; Eumelanin; Pheomelanin

Indexed keywords

5,6 DIHYDROXYINDOLE; CYSTEINE; CYSTEINYLDOPA; DOPACHROME; DOPACHROME TAUTOMERASE; DOPAQUINONE; INDOLE DERIVATIVE; MELANIN; MONOPHENOL MONOOXYGENASE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

BINDING AFFINITY; BINDING KINETICS; CATALYSIS; CELL FATE; CONFERENCE PAPER; CORRELATION ANALYSIS; CYTOTOXICITY; DECOMPOSITION; ENZYME ACTIVITY; MELANOGENESIS; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; OXIDATION; PROTEIN BINDING; PROTEIN SYNTHESIS; PULSE RADIOLYSIS; REACTION ANALYSIS;

ANIMALS; CYSTEINE; HUMANS; MELANINS; MELANOCYTES; MODELS, BIOLOGICAL; MODELS, CHEMICAL; TIME FACTORS;

EID: 0037902622     PISSN: 08935785     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1600-0749.2003.00037.x     Document Type: Conference Paper

References (31)

1. Prota G. Melanin and Melanogenesis. New York: Academic Press, 1992: pp. 1-290
2. Napolitano A, Pezzella A, Prota G, Seraglia R, Traldi P. Structural analysis of synthetic melanins from 5,6-dihydroxyindole by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun Mass Spectrometry 1996;10:468-472
3. Ito S, Wakamatsu K, Ozeki H. Chemical analysis of melanins and its application to the study of the regulation of melanogenesis. Pigment Cell Res 2000;13 (Suppl. 8):103-109
4. Ito S, Fujita K. Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid chromatography. Anal Biochem 1985;144:527-536
5. Wakamatsu K, Ito S, Rees JL. The usefulness of 4-amino-3-hydroxyphenylalanine as a specific marker of pheomelanin. Pigment Cell Res 2002;15:225-232
6. Ozeki H, Ito S, Wakamatsu K, Hirobe T. Chemical characterization of hair melanins in various coat-color mutants of mice. J Invest Dermatol 1995;105:361-366
7. Tse DCS, McCreery RL, Adams RN. Potential oxidative pathways of brain catecholamines. J Med Chem 1976;19:37-40
8. Cooksey CJ, Land EJ, Rushton FAP, Ramsden CA, Riley PA. Tyrosinase-mediated cytotoxicity of 4-substituted phenols: use of QSAR to forecast reactivities of thiols towards the derived orthoquinones. Quant Struct-Act Relat 1996;15:498-503
9. Land EJ, Ramsden CA, Riley PA. Pulse radiolysis studies of orthoquinone chemistry relevant to melanogenesis. J Photochem Photobiol B Biol 2001;64:123-135
10. Land EJ, Riley PA. Spontaneous redox reactions of dopaquinone and the balance between the eumelanic and phaeomelanic pathways. Pigment Cell Res 2000;13:273-277
11. Ito S, Prota G. A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase. Experientia 1977;33:1118-1119
12. Wakamatsu K, Ito S. Evaluation of 5-S-cysteinyldopa as a marker of melanoma progression: 10 years' experience. Melanoma Res 2002;12:245-253
13. Ozeki H, Ito S, Wakamatsu K, Ishiguro I. Chemical characterization of pheomelanogenesis starting from dihydroxyphenylalanine and cysteine. Effects of tyrosinase and cysteine concentrations and reaction time. Biochim Biophys Acta 1997;1336:539-548
14. del Marmol V, Ito S, Bouchard B, Libert A, Wakamatsu K, Ghanem G, Solano F. Cysteine deprivation promotes eumelanogenesis in human melanoma cells. J Invest Dermatol 1996;107:698-702
15. Palumbo A, d'Ischia M, Misuraca G, Prota G. Effect of metal ions on the rearrangement of dopachrome. Biochim Biophys Acta 1987;925:203-209
16. Palumbo A, Solano F, Misuraca G, Aroca P, Garcia Borron JC, Lozano JA, Prota G. Comparative action of dopachrome tautomerase and metal ions on the rearrangement of dopachrome. Biochim Biophys Acta 1991;1115:1-5
17. Wakamatsu K, Ito S. Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and their O-methyl derivatives. Anal Biochem 1988;170:335-340
18. Pawelek J, Korner A, Bergstrom A, Bologna J. New regulators of melanin biosynthesis and the autodestruction of melanoma cells. Nature 1980;286:617-619
19. Ito S. Reexaminaton of the structure of eumelanin. Biochim Biophys Acta 1986;883:155-161
20. Ozeki H, Wakamatsu K, Ito S, Ishiguro I. Chemical characterization of eumelanins with special emphasis on 5,6-dihydroxyindole-2-carboxylic acid content and molecular size. Anal Biochem 1997;248:149-157
21. Lamoreux ML, Wakamatsu K, Ito S. Interaction of major coat color gene function in mice as studied by chemical analysis of eumelanin and pheomelanin. Pigment Cell Res 2001;14:23-31
22. Hearing V. The melanosome: the perfect model for cellular responses to the environment. Pigment Cell Res 2000;13(Suppl. 8):23-34
23. Napolitano A, Crescenzi O, Prota G. Copolymerization of 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid in melanogenesis: isolation of a cross-coupling product. Tetrahedron Lett 1993;34:885-888
24. Graham DG, Tiffany SM, Bell WR, Gutknecht WF. Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro. Mol Pharmacol 1978;14:644-653
25. Ito S, Kato T, Fujita K. Covalent binding of catechols to proteins through the sulphydryl group. Biochem Pharmacol 1988;37:1707-1710
26. Hawley MD, Tatawawadi SV, Piekarski S, Adams RN. Electrochemical studies of the oxidation pathways of catecholamines. J Am Chem Soc 1967;89:447-450
27. Barzilai A, Zilkha-Falb R, Daily D, Stern N, Offen D, Ziv I, Melamed E, Shirvan A. The molecular mechanism of dopamine-induced apoptosis: identification and characterization of genes that mediate dopamine toxicity. J Neural Transm 2000;60 (Suppl.):59-76
28. Riley PA, Cooksey CJ, Johnson CI, Land EJ, Latter AM, Ramsden CA. Melanogenesis-targeted anti-melanoma pro-drug development effect of side-chain variations on cytotoxicity of tyrosinase-generated ortho-quinones in a model system. Eur J Cancer 1997;33:135-143
29. Inoue S, Hasegawa K, Wakamatsu K, Ito S. Comparison of antimelanoma effects of 4-S-cysteaminylphenol and its homologues. Melanoma Res 1998;8:105-112
30. Mascagna D, Costantini C, d'Ischia M, Prota G. Biomimetic oxidation of the antimelanoma agent 4-S-cysteaminylphenol and related catechol thioethers: isolation and reaction behaviour of novel dihydrobenzothiazinequinones. Tetrahedron 1994;50:8757-8764
31. Hasegawa K, Ito S, Inoue S, Wakamatsu K, Ozeki H, Ishiguro I. Dihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4-S-cysteaminylphenol and 4-S-cysteaminylcatechol. Biochem Pharmacol 1997;53:1435-1444