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Melanin, Melanogenesis, and Vitiligo

  • Chapter
Progress in the Chemistry of Organic Natural Products

Abstract

Melanins, pigments of diverse origin and chemical function, have been subjects of interest for a long time (Aristotle, in “Historia Animalia”, 315 B.C.). These natural cosmetics of skin, hair, and feathers usually occur in the form of insoluble fine granules in certain dendritic cells of the epidermis. The term melanin (μɛλαζ = black) is, however, misleading and confusing since not all biogenetically related pigments are black. The melanogenic enzyme, tyrosinase, is known to catalyze the biosynthesis of not only black but also red to brown, or even yellow pigments, e.g. pheomelanins (208, 266). On the other hand, the fascinating colors in the feathers of birds, skins of reptiles and fishes and the blue eyes in animals are optical phenomena due to diffraction, light absorption and scattering, interference, that are produced by melanin granules either in combination or not, with other pigmentary colors (94, 156) and by complex formation of the granules with heavy metals (21, 156).

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References

  1. Alexandrova M (1994) Stress Induced Tyrosine Aminotransferase Activity via Glucocorticoid Receptor. Hormone Metabolic Res 26: 97

    CAS  Google Scholar 

  2. Al-Kazwini AT, O’Neill P, Cundall RB, Adams GE, Junino A, Maignan J (1992) Direct Observation of the Reaction of the Quinone Methide from 5,6-Dihydroxyindole with the Nucleophilic Azide Ion. Tetrahedron Lett 33: 3045

    CAS  Google Scholar 

  3. Allegri G, Biasiolo M, Frison G, Pelli B, Traldi P (1987) Collisional Spectroscopy in Structural Characterization of Melanins. 1. A First Study on C8H7ON+ Ions Originating from Pyrolysis of Biosynthetic and Synthetic Tryptophan Melanins. Pigment Cell Res 1: 87

    CAS  Google Scholar 

  4. Aroca P, Garcia-Borron JC, Solano F, Lozano JA (1990) Regulation of Distal Mammalian Melanogenesis. 1: Partial Purification and Characterization of a Dopachrome Converting Factor: Dopachrome Tautomerase. Biochim Biophys Acta 1035: 266

    CAS  Google Scholar 

  5. Ban TA, Lehmann HE, Gallai Z, Warnes H, Lee H (1965) Relation Between Photosensitivity and the Pathological Pigmentation of the Skin Produced by High Doses of Chlorpromazine. Union Med Canada 94: 305

    CAS  Google Scholar 

  6. Barua A, Banik UK, Chakraborty DP (1961) Endocrinological Studies on Plant Products: Part 1. Preliminary Investigation of Hormonal Action of Psorelen. Ann Biochem Expt Med 21: 132

    Google Scholar 

  7. Beer RJS, Broadhurst T, Robertson A (1954) The Chemistry of the Melanins, Part V: The Autooxidation of 5,6-Dihydroxyindoles. J Chem Soc (London): p. 1947

    Google Scholar 

  8. Benathan M, Wyler H (1980) Contribution a l’Analyse Quantitative des Melanines. Yale J Biol Med 53: 389

    Google Scholar 

  9. Bertrand G (1986) Sur un Nouvelle Oxydase on Ferment Soluble Oxydant, d’Origine Vegitable. Comp Rend Acad Sci (Paris) 122: 1215

    Google Scholar 

  10. Billingham RE, Silvers WK (1960) The Melanocytes of Mammals. Q Rev Biol 35: 1

    CAS  Google Scholar 

  11. Bischitz PG, Snell RS (1959) The Effect of Testosterone on the Melanocytes and Melanin in the Skin of the Intact and Orchidectomised Male Guinea-Pig. J Inves Dermatol 33: 299

    CAS  Google Scholar 

  12. Bischitz PG, Snell RS (1960) A Study of the Effect of Ovariectomy, Estrogen and Progesterone on the Melanocytes and Melanin in the Skin of the Female Guinea-Pig. J Endocrinol 20: 312

    CAS  Google Scholar 

  13. Biswas NM, Chakraborty DP, Dev C (1965) Influences of Pituitary on the Melanin Formation in Psoralen Treated Tode (Bufo melanostictus). Naturwiss 22: 622

    Google Scholar 

  14. Biswas NM, Dev C, Chakraborty DP (1967) Effects of Psoralen on Pigmentation in Hypophysectomized Tode (Bufo melanostictus). Endokrinologie 52: 271

    CAS  Google Scholar 

  15. Bleehen SS, Pathak MA, Hori Y, Fitzpatrick TB (1965) Depigmentation of Skin with 4-Isopropylcatechol, Mercaptoamines and Other Compounds. J Invest Dermatol 50: 103

    Google Scholar 

  16. Blois MS (1969) Biological Free Radicals and the Melanins. In: Wyard SJ (ed.) Solid State Biophysics, p. 243. McGraw-Hill, New York

    Google Scholar 

  17. Blois MS (1972) The Binding Properties of Melanin: in vivo and in vitro. In: Montagna W, Stoughton RB, Van Scott EJ (eds.) Advances in Biology of Skin, Vol. XII. Pharmacology and the Skin, p. 65. Appleton-Century-Crofts, New York

    Google Scholar 

  18. Blois MS (1978) The Melanins: Their Synthesis and Structure. Photochem Photobiol Rev 3: 115

    CAS  Google Scholar 

  19. Bolognia JL, Powelek JM (1988) Biology of Hypopigmentation. Am Acad Dermatol 19: 217

    CAS  Google Scholar 

  20. Borkovic SP, Alper JC, McDonald CJ (1983) Stimulation of Pigmentation in Melanoma Cells by Trimethylpsoralen in Absence of Ultraviolet Irradiation. Br J Dermatol 108: 525

    CAS  Google Scholar 

  21. Bowness JM, Morton RA (1953) The Association of Zinc and Other Metals with Melanin and Melanin-Protein Complex. Biochem J 53: 620

    CAS  Google Scholar 

  22. Bowers RR, Lujan J, Bibso A, Kridel S, Varkey C (1994) Premature Avian Melanocyte Death Due to Low Antioxidant Levels of Protection: Fowl Model for Vitiligo. Pigment Cell Res 7: 409

    CAS  Google Scholar 

  23. Boyland E, Willium DC (1956) The Metabolism of Tryptophan. Biochem J 64: 578

    CAS  Google Scholar 

  24. Breathnach AS, Bor S, Wyllie LMA (1966) Electron Microscopy of Peripheral Nerve Terminals and Marginal Melanocytes in Vitiligo. J Invest Dermatol 47: 125

    CAS  Google Scholar 

  25. Bridelli M, Capelleti R, Crippa PR (1981) Electret State and Hydrated Structure of Melanin. Bioelectrochem Bioeng 8: 555

    CAS  Google Scholar 

  26. Brown KT (1965) An Early Potential Evoked by Light from the Pigment Epithelium-Choroid Complex of the Eye of the Tode. Nature 207: 1249

    CAS  Google Scholar 

  27. Brown FC, Ward DN, Griffin AC (1959) Preparation and Properties of Mammalian Tyrosinase. In: Gorden M (ed.) Pigment Cell Biology, p. 525. Academic Press, New York

    Google Scholar 

  28. Bruenger FW, Stover BJ, Atherton DR (1967) The Incorporation of Various Metal Ions into in vivo- and in vitro-Produced Melanin. Rad Res 32: 1

    CAS  Google Scholar 

  29. Burn R (1972) A Propose de Etiologie du Vitiligo. Dermatologica 145: 169

    Google Scholar 

  30. Bu’Lock JD, Harley-Mason J (1951) Melanin and Its Precursors, Part II: Model Experiments on the Reactions Between Quinones and Indoles, and Consideration of a Possible Structure for the Melanin Polymer. J Chem Soc (London): p. 703

    Google Scholar 

  31. Burger AC, Van Oordt GJ (1962) Regulation of Pigment Migration in the Amphibian Melanophore. Gen Comp Endocrinol 1: 99

    Google Scholar 

  32. Cabanes J, Garcia-Canovas F, Lozano JA, Garcia-Carmona P (1987) A Kinetic Study of the Melanization Pathway Between L-Tyrosine and Dopachrome. Biochim Biophys Acta 923: 187

    CAS  Google Scholar 

  33. Cassidy HG, Kun KA (1965) In: Oxidation-Reduction Polymer: Redox Polymer. Wiley (Interscience), New York

    Google Scholar 

  34. Carter DM, Powelek JM, Candit ES, Koch NG (1974) Stimulation of Tyrosinase by Trimethylpsoralen and Ultraviolet Light in Pigment Cells (Abstr). J Invest Dermatol 62: 347

    Google Scholar 

  35. de Castro LF (1958) Neuropigmentary System and Cell Division in the Maintenance of the Vital Equilibrium of Tissue; A New Theory. Hospital (Rio de Janeiro) 53: 553

    Google Scholar 

  36. Chakraborty AK, Chakraborty DP (1993) The Effect of Tryptophan on Dopa-Oxidation on Melanosomal Tyrosinase. Int J Biochem 25: 1277

    CAS  Google Scholar 

  37. Chakraborty AK, Chakraborty A, Chakraborty DP (1993) Hydroquinone Simultaneously Induces Indoleamine-2,3-dioxygenase and Inhibits Tyrosinase in Bufo melanostictus. Life Sci 52: 1695

    CAS  Google Scholar 

  38. Chakraborty AK, Pawelek J: Unpublished data

    Google Scholar 

  39. Chakraborty C, Chakraborty AK, Dutta AK, Chakraborty DP (1983) Abnormal Tryptophan Pyrrolase and Amino Acids Related to Melanogenesis in Vitiligo. Experientia 39: 280

    CAS  Google Scholar 

  40. Chakraborty C, Chatterjee A, Chakraborty AK, Chakraborty DP (1984) Inverse-Relationship Between Melanogenesis and Endogenous Hydroquinone. Experientia 40: 829

    CAS  Google Scholar 

  41. Chakraborty C, Ichihashi M, Ueda M, Mishima Y, Chakraborty DP (1986) Effects of Tryptophan on Melanogenesis in B16-F10 Melanoma Cells in Culture. IRCS Med Sci 14: 463

    CAS  Google Scholar 

  42. Chakraborty DP, Das Gupta A, Bose PK (1957) On the Antifungal Activity of Some Natural Coumarins. Ann Biochem Expt Med 17: 59

    CAS  Google Scholar 

  43. Chakraborty DP, Dev C, Mukherjee M (1959) Effect of Psoralen on Tyrosinase Activity and Melanin Pigmentation. Sci Cult 25: 386

    Google Scholar 

  44. Chakraborty DP, Sen M, Bose PK (1961) On the Antibiotic Activity of Some Natural Coumarins. Trans Bose Res Inst 24: 31

    CAS  Google Scholar 

  45. Chakraborty DP (1966) Some Biochemical and Chemotherapeutic Aspects of Vitiligo. Indian J Dermatol 11: 1

    Google Scholar 

  46. Chakraborty DP (1968) Some Aspects of Psoralen Drugs. Sci Cult 34: 33

    CAS  Google Scholar 

  47. Chakraborty DP, Chatterjee A, Chakraborty AK (1977) In: Abstracts. Indian Chemical Society Symposium. Jaipur, India

    Google Scholar 

  48. Chakraborty DP, Chatterjee A (1977) Urinary Indole Profile of Bufo melanostictus During Hydroquinone Induced Leucoderma and Its Regeneration. Clin Chem Acta 79: 399

    CAS  Google Scholar 

  49. Chakraborty DP, Roychowdhury SK, Dey RN, Chatterjee A (1978) Interrelationship of Tryptophan Pyrrolase with Tyrosinase in Melanogenesis of Bufo melanostictus. Clin Chem Acta 82: 55

    CAS  Google Scholar 

  50. Chakraborty DP, Chakraborty C, Ganguly M, Chakraborty AK (1983) Trace Metals and Melanogenesis. Experientia 39: 282

    CAS  Google Scholar 

  51. Chakraborty DP, Roy S, Chakraborty AK, Rakshit R (1986) Tryptophan Participation in Melanogenesis: A Biomimetic Study. IRCS Med Sci 14: 940

    CAS  Google Scholar 

  52. Chakraborty DP, Roy S, Chakraborty AK, Rakshit R, Chakraborty A (1988) Profile of Stress Conditions During Induced Depigmentation: Tryptophan Participation in Melanogenesis and Composite Hypothesis of Vitiligo. IRCS Med Sci 16: 21

    CAS  Google Scholar 

  53. Chakraborty DP, Roy S, Chakraborty AK, Rakshit R (1989) Tryptophan Participation in Melanogenesis: Modification of Raper-Mason-Powelek Scheme of Melanin Formation. J Ind Chem Soc 66: 699

    CAS  Google Scholar 

  54. Chakraborty DP, Roy S, Chakraborty AK (1996) Vitiligo, Psoralen, and Melanogenesis: Some Observations and Understanding. Pigment Cell Res 9: 107

    CAS  Google Scholar 

  55. Chakraborty DP, Roy S (2003) Chemical and Biological Aspects of Melanin. In: Cordell Geoffreya A (ed.) The Alkaloids, Vol. 60, p. 345

    Google Scholar 

  56. Chavin H, Schlesinger W (1967) Effects of Melanin Depigmental Agents Upon Normal Pigment Cells, Melanoma and Tyrosinase Activity. In: Montagna W, Hu H (eds.) Advances in the Biology of Skin, Vol. 1, p. 421. Pergamon Press, New York

    Google Scholar 

  57. Chedekel MR, Post PW, Deibel RM, Kalus M (1977) Photodestruction of Phaeomelanin. Photochem Photobiol 26: 651

    CAS  Google Scholar 

  58. Chedekel MR, Land EJ, Sinelair RS, Tait D, Truscott TG (1980) Photochemistry of 4-Hydroxybenzothiazole: A Model for Phaeomelanin Photodegradation. J Am Chem Soc 102: 6587

    CAS  Google Scholar 

  59. Chedekel MR, Subbarao KV, Bahan P, Schultz TM (1987) Biosynthetic and Structural Studies on Phaeomelanin. Biochim Biophys Acta 912: 239

    CAS  Google Scholar 

  60. Chedekel MR, Patil DG, Rao KV, Murphy BP, Clark M, Gardella J, Schultz TM (1988) Solid Phase Carbon 13NMR of 13C-Enriched Eumelanins: The Fate of the Pyrrolic Ring. Pigment Cell Res 1: 282

    Google Scholar 

  61. Chen YM, Chavin W (1965) Radiometric Assay of Tyrosinase and Theoretical Consideration for Melanin Formation. Analyt Biochem 13: 234

    CAS  Google Scholar 

  62. Chen YM, Chavin W (1972) Effects of Depigmentary Agents and Related Compounds Upon in vitro Tyrosinase Activity. In: Riley V (ed.) Pigmentation, Its Genesis and Biological Control, p. 593. Appleton-Century-Crofts, New York

    Google Scholar 

  63. Chio SS, Hyde JS, Sealy RC (1980) Temperature Dependent Paramagnetism in Melanin Polymers. Arch Biochem Biophys 199: 133

    CAS  Google Scholar 

  64. Cole RS (1970) Light-Induced Cross-Linking of DNA in the Presence of Furocoumarin. Biochim Biophys Acta 217: 30

    CAS  Google Scholar 

  65. Commoner B, Townsend J, Pake GE (1954) Free Radicals in Biological Materials. Nature 174: 689

    CAS  Google Scholar 

  66. Cope FW, Sever RJ, Polis BD (1963) Reversible Free Radical Generation in the Melanin Granules of the Eye by Visible Light. Arch Biochem Biophys 100: 171

    CAS  Google Scholar 

  67. Costantini C, Crescenzi O, Prota G (1991) Mechanism of the Rearrangement of Dopachrome to 5,6-Dihydroxyindole. Tetrahedron Lett 31: 3849

    Google Scholar 

  68. Costa C, Allegri G, DeAntoni A (1975) Studies on Melanogenesis of Tryptophan in Harding-Passey Mouse Melanoma. Acta Vitaminol Enzymol 29: 223

    CAS  Google Scholar 

  69. Courrier R, Cehovic G (1960) Action of Purified Melanophorotropic Hormone (α-MSH) on Thyroid Function in the Rabbit. Compt Rend Acad Sci 251: 832

    CAS  Google Scholar 

  70. Crippa R, Cristofoletti V, Romeo N (1978) A Band Model for Melanin Deduced from Optical Absorption and Photoconductivity Experiments. Biochim Biophys Acta 538: 164

    CAS  Google Scholar 

  71. Crippa R, Horok V, Prota G, Svoronos P, Wolfram L (1989) Chemistry of Melanins. In: Brossi A (ed.) The Alkaloids, Vol. 36, p. 253. Academic Press, New York

    Google Scholar 

  72. Cross CC, Halliwell B, Borrish ET, Pryor WA, Ames BN, Saul RL, McCord JM, Harman D (1987) Oxygen Radicals and Human Disease. Ann Intern Med 107: 526

    CAS  Google Scholar 

  73. a) Das SK, Majumdar P, Chakraborty R, Majumdar TK, Halder B (1985) Studies in Vitiligo, 1. Epidemiological Profile in Calcutta (India). Gene Epidemiol 2: 71; b) Das SK, Majumdar PP, Majumdar TK, Halder B (1985) Studies in Vitiligo, II. Familial Aggregation and Genetics. Gene Epidemiol 2: 255

    CAS  Google Scholar 

  74. Delacretaz J (1965) Effect of Testosterone on Tyrosinase Activity on an Experimental Melanoma S-91 of Mice. Ann Dermatol Syph 92: 25

    CAS  Google Scholar 

  75. de Mol NJ, Beijersbergen van Henegouwen GMJ, Gerritsma KW (1979) Photochemical Decomposition of Catecholamines-II. The Extent of Aminochrome Formation from Adrenaline, Isoprenaline and Noradrenaline Induced by Ultraviolet Light. Photochem Photobiol 29: 7479

    Google Scholar 

  76. d’Ischia M, Palumbo A, Prota G (1985) 5,6-Dihydroxyindole-2-carboxylic Acid by Treatment of Sepiomelanin with Sodium Borohydride. Tetrahedron Lett 26: 2801

    CAS  Google Scholar 

  77. a) d’Ischia M, Napolitano A, Prota G (1987) Sulphydril Compounds in Melanogenesis, Part I: Reaction of Cysteine and Glutathion with 5,6-Dihydroxyindoles. Tetrahedron 43: 5351; b) d’Ischia M, Napolitano A, Prota G (1987) Sulphydril Compounds in Melanogenesis, Part II: Reaction of Cysteine and Glutathion with Dopachrome. Tetrahedron 43: 5357

    CAS  Google Scholar 

  78. d’Ischia M, Prota G (1987) Photooxidation of 5,6-Dihydroxy-1-methyl-indole. Tetrahedron 43: 431

    CAS  Google Scholar 

  79. d’Ischia M, Napolitano A, Tsiakas K, Prota G (1990) New Intermediates in the Oxidative Polymerization of 5,6-Dihydroxyindole to Melanin Promoted by Peroxidase/H2O2 System. Tetrahedron 46: 5789 and refs. therein

    CAS  Google Scholar 

  80. Drochmans P (1961) Study by Electron Microscope of the Mechanism of Melanin Pigmentation; the Distribution of Melanin Granules in the Malpighian Cells. Pathol Biol 9: 947

    CAS  Google Scholar 

  81. Dworzanski JP (1983) J Anal Appl Pytolysis 5: 69; Chem Abstr 99: 35447x (1983)

    CAS  Google Scholar 

  82. Dyster-Aas K, Krakau CET (1964) Increased Permeability of the Blood-Aqueous Humor Barrier in the Rabbit’s Eye Provoked by Melanocyte-Stimulating Peptides. Endocrinology 74: 255

    CAS  Google Scholar 

  83. Ebrey TG, Cone RA (1967) Melanin, a Possible Pigment for the Photostable Electrical Responses of the Eye. Nature 213: 360

    CAS  Google Scholar 

  84. El Mofty AM (1948) A Preliminary Clinical Report on the Treatment of Leucoderma with Ammi majus Linn. J Egypt Med Assoc 31: 651

    Google Scholar 

  85. Erway L, Hurley L, Fraser A (1966) Neurological Defect: Manganese in Phenocopy and Prevention of a Genetic Abnormality of Inner Ear. Science 152: 1766

    CAS  Google Scholar 

  86. Feigelson P, Brady FO (1974) In: Hayaishi O (ed.) Molecular Mechanism of Oxygen Activation, p. 87. Academic Press, New York

    Google Scholar 

  87. Felix CC, Hyde JS, Sarna T, Sealy RC (1978) Interaction of Melanin with Metal Ions. Electron Spin Resonance Evidence for Chelate Complexes of Metal Ions with Free Radicals. J Am Chem Soc 100: 3922

    CAS  Google Scholar 

  88. Fitzpatrick TB, Becker Jr SW, Lerner AB, Montgomery H (1950) Tyrosinase in Human Skin: Demonstration of Its Presence and Its Role in Human Melanin Formation. Science 112: 223

    CAS  Google Scholar 

  89. Fitzpatrick TB (1952) Human Melanogenesis. Arch Dermatol Syph 65: 379

    CAS  Google Scholar 

  90. Fitzpatrick TB, Szabo G (1959) The Melanocytes: Cytology and Cytochemistry. J Invest Dermat 32: 197

    CAS  Google Scholar 

  91. Fitzpatrick TB, Miyamoto M, Ishikawa K (1967) The Evolution of Concepts of Melanin Biology. Arch Dermatol 96: 305

    CAS  Google Scholar 

  92. Fitzpatrick TB, Mihm MC (1971) In: Fitzpatrick TB, Eisen HS, Wolff K, Freedberg M, Austen KF (eds.) Dermatology in General Medicine, p. 1596. McGraw Hill, New York

    Google Scholar 

  93. Flesch P (1949) Inhibitory Action of Extracts of Mammalian Skin on Pigment Formation. Proc Soc Exp Biol NY 70: 136

    CAS  Google Scholar 

  94. Foster M(1959) Physiological Genetic Aspects of Mammalian Melanogenesis. Ann NY Acad Sci 100: 743

    Google Scholar 

  95. Fox DL, Kuchnow KP (1965) Reversible Light-Screening Pigment of Elasmobranch Eyes: Chemical Identity with Melanin. Science 150: 612

    CAS  Google Scholar 

  96. Fox DL (1976) In: Animal Biochromes and Structural Color, 2nd edn. University of California Press, Berkeley

    Google Scholar 

  97. Frenk E (1975) Pigment Cell Biology and Its Relation to Disorders of Melanin Pigmentation (Review). Dermatologica 159: 185

    Google Scholar 

  98. Friedman S, Kaufman S (1965) 3,4-Dihydroxyphenylethylamine β-Hydroxylase. Physical Properties, Copper Content, and Role of Copper in the Catalytic Activity. J Biol Chem 240: 4763

    CAS  Google Scholar 

  99. Fukuzawa T, Bagnara JT (1989) Control of Melanoblast Differentiation in Amphiba by α-Melanocyte Stimulating Hormone, a Serum Melanization Factor, and a Melanization Inhibiting Factor. Pigment Cell Res 2: 171

    CAS  Google Scholar 

  100. a) Galvao DS, Caldas MJ (1990) Theoretical Investigation of Model Polymers for Eumelanins, I: Finite and Infinite Polymers. J Chem Phys 92: 2630; b) Galvao DS, Caldas MJ (1990) Theoretical Investigation of Model Polymers for Eumelanins, II: Isolated Defects. J Chem Phys 93: 2848

    CAS  Google Scholar 

  101. Gan EV, Haverman HF, Menon IA (1976) Electron Transfer Properties of Melanin. Arch Biochem Biophys 173: 666

    CAS  Google Scholar 

  102. Gilchrest BA, Blog FB, Szabo G (1979) Effects of Aging and Chronic Sun Exposure on Melanocytes in Human Skin. J Invest Dermatol 73: 141

    CAS  Google Scholar 

  103. Hadley E, Quevedo W (1967) The Role of Epidermal Melanocytes in Adaptive Color Changes in Amphibians. In: Montagna W, Hu F (eds.) Advances in Biology of Skin, Vol. VIII. Pergmon Press, Oxford

    Google Scholar 

  104. Hall TC, McCracken BH, Thorn GW (1953) Skin Pigmentation in Relation to Adrenal Cortical Function. J Clin Endocrinol Metabol 13: 243

    CAS  Google Scholar 

  105. Hamilton JB (1939) Significance of Sex Hormones in Tanning of the Skin of Women. Proc Soc Exptl Biol Med 40: 502

    CAS  Google Scholar 

  106. Hamilton GA, Workman RJ, Woo L (1964) Oxidation by Molecular Oxygen. I. Reactions of a Possible Model System for Mixed-Function Oxidases. J Am Chem Soc 86: 3390

    CAS  Google Scholar 

  107. Hamilton GA (1964) Oxidation by Molecular Oxygen. II. The Oxygen Atom Transfer Mechanism for Mixed-Function Oxidases and the Model for Mixed-Function Oxidases. J Am Chem Soc 86: 3391

    CAS  Google Scholar 

  108. Hawley MD, Tatawawadi SV, Piekarski S, Adams RN (1967) Electrochemical Studies of the Oxidation Pathways of Catecholamines. J Am Chem Soc 89: 447

    CAS  Google Scholar 

  109. Hayaishi O (1964) Proc 6th Intern Congr Biochem, Plenary Sessions, New York 33: 31

    Google Scholar 

  110. Hearing VJ, Ekel TM, Montague PM, Nicholson JM (1980) Mammalian Tyrosinase. Stoichiometry and Measurement of Reaction Products. Biochim Biophys Acta 611: 251

    CAS  Google Scholar 

  111. Hempel K (1966) Investigation on the Structure of Melanin in Malignant Melanoma with 3H-and 14C-Dopa Labelled at Different Positions. In: Della Prota G, Muhlbock O (eds.) Structure and Control of Melanocytes, p. 162. Springer, Berlin Heidelberg New York

    Google Scholar 

  112. Hochstein P, Cohen G (1963) The Cytotoxicity of Melanin Precursors. Ann NY Acad Sci 100: 876

    CAS  Google Scholar 

  113. Holstein TJ, Stowell CP, Quevedo Jr WC, Zarearo RM, Bienieki TC (1973) Peroxidase, “Protyronase” and the Multiple Forms of Tyrosinase in Mice. Yale J Biol Med 46: 560

    CAS  Google Scholar 

  114. Horok V, Gillette JR (1971) A Study of the Oxidation-Reduction State of Synthetic 3,4-Dihydroxy-DL-phenylalanin Melanin. Molec Pharmacol 7: 429

    Google Scholar 

  115. Horok V: Unpublished experimental observation

    Google Scholar 

  116. Hunter JAA, Mottaz JH, Zelickson AS (1970) Melanogenesis: Ultrastructural Histochemical Observations on Ultraviolet Irradiated Human Melanocytes. J Invest Dermatol 54: 213

    CAS  Google Scholar 

  117. Imokawa G, Yada Y, Hori Y (1987) In: Jimbow K (ed.) The Structure and Function of Melanin, Vol. 4, p. 60. Fuji-Shoin Co. Ltd., Sapporo, Japan

    Google Scholar 

  118. Ippen H (1961) The Pineal Body Hormone Melatonin and the Central Pigment Regulation. Deut Med Wochenschr 86: 307

    CAS  Google Scholar 

  119. Ito S, Prota G (1977) A Facile One-Step Synthesis of Cysteinyldopa Using Mushroom Tyrosinase. Experientia 33: 1118

    CAS  Google Scholar 

  120. Ito S, Palumbo A, Prota G (1985) Tyrosinase-Catalyzed Conjugation of Dopa with Glutathion. Experientia 41: 960

    CAS  Google Scholar 

  121. Ito S (1986) Reexamination of the Structure of Eumelanin. Biochim Biophys Acta 883: 155

    CAS  Google Scholar 

  122. Ito S, Imai Y, Kato T, Fujita K (1987) In: Jimbow K (ed.) Structure and Function of Melanin, p. 44. Fuji-Shoin Co. Ltd., Sapporo, Japan

    Google Scholar 

  123. Jimbow K, Szabo G, Fitzpatrick TB (1974) Ultrastructural Investigation of Autophagocytosis of Melanosomes and Programmed Death of Melanocytes in White Leghorn Feathers: A Study of Morphogenetic Events Leading to Hypomelanosis. Dev Biol 36: 8

    CAS  Google Scholar 

  124. Jimbow K, Fitzpatrick TB, Szabo G, Hori Y (1975) Congenital Circumscribed Hypomelanosis: A Characterization Based on Electronmicroscopic Study of Tuberous Sclerosis, Nevus depigmentosus, and Piebaldism. J Invest Dermatol 64: 50

    CAS  Google Scholar 

  125. Jimbow K, Quevedo WC, Fitzpatrick TB, Szabo G (1976) Some Aspects of Melanin Biology (Review): 1950–1975. J Invest Dermatol 67: 72

    CAS  Google Scholar 

  126. Kalyanaraman B, Felix CC, Sealy RC (1985) Semiquinone Anion Radicals of Catecholamines, Catechol, Estrogens, and Their Metal Ion Complexes. Environ Health Perspect 64: 185

    CAS  Google Scholar 

  127. Kean EA (1964) A Procedure Which Demonstrates Substrate Inhibition of Tyrosinase. Biochem Biophys Acta 92: 602

    CAS  Google Scholar 

  128. Kertesz D (1954) The Phenol Oxidizing Enzyme System of Human Melanomas: Substrate Specificity and Relationship to Copper. J Nat Cancer Inst 14: 1081

    CAS  Google Scholar 

  129. Khansari DN, Murgo AJ, Faith RE (1990) Effects of Stress on the Immune System (Review). Immunol Today 11: 170

    CAS  Google Scholar 

  130. Kirby GW, Ogunkoya L (1965) Structure of Melanin Derived from (±)-3,4-Dihydroxy-[14C, 3H]-phenylalanin by Oxidation with Tyrosinase. Chem Commun 21: 546

    Google Scholar 

  131. Kissinger PT, Hineman WR (1984) In: Laboratory Techniques in Electroanalytical Chemistry, p. 611. Dekker, New York

    Google Scholar 

  132. Kono R, Yamaoka H, McGinness J (1979) Anomalous Absorption and Dispersion of Sound Wave in Diethylamine Melanin. J App Phys 50: 1242

    Google Scholar 

  133. Kosto B, Pickford GE, Foster M (1959) Further Studies of the Hormonal Induction of Melanogenesis in Killifish, Fundulus heteroclitus. Endocrinol 65: 869

    CAS  Google Scholar 

  134. Korner A, Powelek J (1980) Dopachrome Conversion: A Possible Control Point in Melanin Biosynthesis. J Invest Dermatol 75: 192

    CAS  Google Scholar 

  135. Korytowski W, Kalyanaraman B, Menon IA, Sarna T, Sealy RC (1986) Reaction of Superoxide Anions with Melanins: Electron Spin Resonance and Spin Trapping Studies. Biochim Biophys Acta 882: 145

    CAS  Google Scholar 

  136. Krivoy WA, Guillemin R (1961) On a Possible Role of β-Melanocyte-Stimulating Hormone (β-MSH) in the Central Nervous System of the Mammalians; an Effect of β-MSH in the Spinal Cord of the Cat. Endocrinol 68: 170

    Google Scholar 

  137. Kurbanov KH, Berezov TT (1976) Tryptophan Metabolism in Vitiligo (Russian). Vopr Med Khim 22: 683

    CAS  Google Scholar 

  138. Lambert C, Chacon JN, Chedekel MR, Land EJ, Riley PA, Thompson A, Truscott G (1989) A Pulse Radiolysis Investigation of the Oxidation of Indolic Melanin Precursors: Evidence for Indolequinones and Subsequent Intermediates. Biochim Biophys Acta 993: 12

    CAS  Google Scholar 

  139. Lancy ME (1984) Phonon-Electron Coupling as a Possible Transducing Mechanism in Bioelectronic Process Involving Neuromelanin. J Theor Biol 111: 201

    Google Scholar 

  140. Lapina VA, Dontsov AE, Ostrovskii MA (1984) a) Chem Abstr (1985) 102: 2110j; b) Chem Abstr (1984) 101: 187528x

    Google Scholar 

  141. Larsson B, Tjalve H (1978) Studies on the Melanin Affinity of Metal Ions. Acta Physiol Scand 104: 479

    CAS  Google Scholar 

  142. Larsson B, Oskarsson A, Tjalve H (1978) On the Binding of the Bisquaternary Ammonium Compound Paraquat to Melanin and Cartilage in vivo. Biochem Pharmacol 27: 1721

    CAS  Google Scholar 

  143. Larsson B, Tjalve H (1979) Studies on the Mechanism of Drug-Binding to Melanin. Biochem Pharmacol 28: 1181

    CAS  Google Scholar 

  144. Lee TH, Lerner AB (1959) Melanocyte-Stimulating Hormones from Pituitary Glands. In: Gordon M (ed.) Pigment Cell Biology, p. 435. Academic Press, New York

    Google Scholar 

  145. Leonard LJ, Townsend D, King RA (1988) Dopachrome Oxidoreductase and Metal Ions in Dopachrome Conversion in the Eumelanin Pathway. Biochemistry 27: 6156

    CAS  Google Scholar 

  146. LePoole IC, Das P, Van den Wijngaard R, Bos J, Westerhof W (1993) Review of the Etiopathomechanism of Vitiligo: A Convergence Theory. Exp Dermatol 2: 145

    CAS  Google Scholar 

  147. Lerner AB, Fitzpatrick TB (1950) Biochemistry of Melanin Formation. Physiol Rev 30: 91

    CAS  Google Scholar 

  148. Lerner AB, Denton CR, Fitzpatrick TB (1953) Clinical and Experimental Studies with 8-Methoxypsoralen in Vitiligo. J Invest Dermatol 20: 299

    CAS  Google Scholar 

  149. Lerner AB, Lerner MR (1958) Congenital and Hereditary Disturbances of Pigmentation. Bibliotheca paediat 66: 308

    Google Scholar 

  150. Lerner AB (1959) Vitiligo. J Invest Dermatol 32: 285

    CAS  Google Scholar 

  151. Lerner AB, Wright MR (1960) In vitro Frog Skin Assay for Agents That Darken and Lighten Melanocytes. Methods of Biochem Anal 8: 295

    CAS  Google Scholar 

  152. Lerner AB, McGuire JS (1961) Effect of Alpha-and Beta-Melanocyte Stimulating Hormones on the Skin Color of Man. Nature 189: 176

    CAS  Google Scholar 

  153. Lerner AB, McGuire JS (1964) Melanocyte-Stimulating Hormone and Adrenocorticotropic Hormone. Their Relation to Pigmentation. New Engl J Med 270: 535

    Google Scholar 

  154. Lerner AB (1971) Neural Control of Pigment Cells. In: Kawamura T, Fitzpatrick TB, Seiji M (eds.) Biology of Normal and Abnormal Melanocytes, p. 3. Tokyo University Press, Tokyo

    Google Scholar 

  155. Lerner AB (1971) On the Etiology of Vitiligo and Gray Hair. Am J Med 51: 141

    CAS  Google Scholar 

  156. Long JM, Krivoy WA, Guillemin R (1961) On a Possible Role of β-Melanocyte-Stimulating Hormone (β-MSH) in the Central Nervous System of Mammalians; Enzymatic Inactivation in vitro of β-MSH by Brain Tissue. Endocrinol 68: 176

    Google Scholar 

  157. Lorinez AL (1954) In: Rothman S (ed.) Pigmentation in Physiology and Biochemistry of the Skin, p. 515. University of Chicago Press, Chicago

    Google Scholar 

  158. Lukiewicz S (1972) The Biological Role of Melanin. 1. New Concepts and Methodical Approaches. Fol Histochem Cytochem 10: 93

    CAS  Google Scholar 

  159. Malmstrom BG, Lars R (1968) Copper Containing Oxidases. In: Singer TP (ed.) Biological Oxidation, p. 415. Academic Press, New York, London

    Google Scholar 

  160. Marsden CD (1969) Brain Melanin. In: Wolman M (ed.) Pigments in Pathology, p. 395. Academic Press, New York

    Google Scholar 

  161. Marwan MM, Jiang JW, de Lauro Castrucci AM, Hadley ME (1990) Psoralen Stimulate Mouse Melanocyte and Melanoma Tyrosinase Activity in the Absence of Ultraviolet Light. Pigment Cell Res 3: 214

    CAS  Google Scholar 

  162. Mason HS (1955) Comparative Biochemistry of the Phenolase Complex. Adv Enzymol 16: 105

    CAS  Google Scholar 

  163. Mason HS, Fowlks WL, Peterson E (1955) Oxygen Transfer and Electron Transport by the Phenolase Complex. J Am Chem Soc 77: 2914

    CAS  Google Scholar 

  164. Mason HS (1957) Mechanisms of Oxygen Metabolism. Adv Enzymol 19: 79

    CAS  Google Scholar 

  165. Mason HS (1967) The Structure of Melanin. In: Montagna W, Hu F (eds.) Advances in Biology of Skin, Vol. VIII, p. 293. Pergamon Press, Oxford

    Google Scholar 

  166. Mayausky JS, McCreery RL (1983) Spectroelectrochemical Examination of Charge Transfer Between Chlorpromazine Cation Radical and Catecholamines. Ann Chem 55: 308

    CAS  Google Scholar 

  167. McCord JM (1987) Oxygen-Derived Radicals: A Link Between Reperfusion Injury and Inflammation. Fed Proc 46: 2402

    CAS  Google Scholar 

  168. McEwan M, Parsons PG (1987) Inhibition of Melanization in Human Melanoma Cells by a Serotonin Uptake Inhibitor. J Invest Dermatol 89: 82

    CAS  Google Scholar 

  169. McGinness J (1972) A Mechanism for Band Gaps in Melanins. Science 177: 896

    CAS  Google Scholar 

  170. McGinness J, Proctor P (1973) The Importance of the Fact That Melanin is Black. J Theor Biol 39: 677

    CAS  Google Scholar 

  171. McGinness J, Corry P, Proctor P (1974) Amorphous Semiconductor Switching in Melanins. Science 183: 853

    CAS  Google Scholar 

  172. McGinness J (1985) A New View of Pigmented Neurons. J Theor Biol 115: 475

    CAS  Google Scholar 

  173. McGuire J (1966) Melanin Granule Dispersion in Epidermal Melanocytes. J Invest Dermatol 45: 547; and refs therein

    Google Scholar 

  174. Mengeaud V, Ortonne JP (1994) Regulation of Melanogenesis Induced by 5-Methoxypsoralen Without Ultraviolet Light in Murine Melanoma Cells. Pigment Cell Res 7: 245

    CAS  Google Scholar 

  175. Mizutani U, Massalski TB, McGinness JE, Corry PM (1976) Low Temperature Specific Heat Anomalies in Melanins and Tumor Melanosomes. Nature (London) 259: 505

    CAS  Google Scholar 

  176. Mohn MP (1957) Inhibitory Effects of Adrenaline on Skin, Hair Growth, and Pigmentation in Black Rats. Anat Record 127: 337

    Google Scholar 

  177. Montagna W, Porta G, Kenney J (1993) In: Black Skin. Academic Press, New York

    Google Scholar 

  178. Mott NF (1967) Electrons in Disordered Structures. Adv Phys 16: 49

    CAS  Google Scholar 

  179. Mottaz JH, Zelickson AS (1967) Melanin Transfer: A Possible Phagocytic Process. J Invest Dermatol 49: 605

    CAS  Google Scholar 

  180. Musajo L, Rodighiero G (1962) The Skin Photosensitizing Furocoumarins. Experientia 18: 153

    CAS  Google Scholar 

  181. Nagata S (1993) Stress-Induced Immune Changes, and Brain-Immune Interaction (Review) (Japanese). Sangy Ika Daigaku Zasshi 15: 161

    CAS  Google Scholar 

  182. Napolitano A, Crescenzi O, Prota G (1993) Copolymerization of 5,6-Dihydroxyindole and 5,6-Dihydroxyindole-2-carboxylic Acid in Melanogenesis. Isolation of a Cross-Coupling Product. Tetrahedron Lett 34: 885

    CAS  Google Scholar 

  183. Nathanson L (1967) Biological Aspects of Human Malignant Melanoma. Cancer 20: 650

    CAS  Google Scholar 

  184. Naughton GK (1983) Detection of Antibodies to Melanocytes in Vitiligo by Specific Immunoprecipitation. J Invest Dermatol 81: 540

    CAS  Google Scholar 

  185. Nelson RM, Mason HS (1970) Tyrosinase (Mushroom). In: Tabor H, Tabor CW (eds.) Methods in Enzymology XVII A, p. 626. Academic Press, New York, London

    Google Scholar 

  186. Nicolaus RA (1968) Melanins. Hermann, Paris

    Google Scholar 

  187. Nordlund JJ, Ortonee JP (1992) Vitiligo and Depigmentation. Curr Prob Dermatol 4: 3

    Google Scholar 

  188. Oikawa A, Nakayasu M (1973) Yale J Biol Med 46: 500;Chem Abstr 81: 74292r (1974)

    CAS  Google Scholar 

  189. Okun MR, Edelstein LM, Hamada G, Bulmental G, Donnellan B, Burnett J (1972) Oxidation of Tyrosine and Dopa to Melanin by Mammalian Peroxidase: The Possible Role of Peroxidase in Melanin Synthesis and Catecholamine Synthesis in vivo. In: Riley V (ed.) Pigmentation, Its Genesis and Biological Control, p. 571. Appleton-Century-Crofts, New York

    Google Scholar 

  190. Ortonee JP, Mosher DB, Fitzpatrick TB (1983) Approach to the Problem of Leucoderma. In: Ortonee JP, Mosher DB, Fitzpatrick TB (eds.) Vitiligo and Other Hypomelanosis of Hair and Skin, p. 37. Plenum, New York

    Google Scholar 

  191. Ortonee JP, Bose S (1993) Vitiligo: Where Do We Stand? Pigment Cell Res 6: 61

    Google Scholar 

  192. Palumbo A, d’Ischia M, Misuraca G, Prota G (1987) Effect of Metal Ions on the Rearrangement of Dopachrome. Biochim Biophys Acta 925: 203

    CAS  Google Scholar 

  193. Palumbo A, d’Ischia M, Prota G (1987) Tyrosinase Promoted Oxidation of 5,6-Dihydroxyindole-2-carboxylic Acid to Melanin. Isolation and Characterization of Oligomer Intermediates. Tetrahedron 43: 4203

    CAS  Google Scholar 

  194. Palumbo A, d’Ischia M, Misuraca M, Prota G (1992) Skin Pigmentation by Hydroquinone: A Chemical and Biochemical Insight. Pigment Cell Res 2: 299

    CAS  Google Scholar 

  195. Palumbo A, d’Ischia M, Misuraca G, De Martino L, Prota G (1994) A New Dopachrome Rearranging Enzyme from the Ejected Ink of the Cuttlefish Sepia officinalis. Biochem J 299: 839

    CAS  Google Scholar 

  196. Parker GH (1948) Animal Color Changes and Their Neurohumours. Cambridge University Press, London

    Google Scholar 

  197. Parrish TA, Fitzpatrick TB, Shea C, Pathak MA (1976) Photochemotherapy of Vitiligo: Use of Orally Administrated Psoralens and a High-Intensity Long-Wave Ultraviolet Light System. Arch Dermatol 112: 1531

    CAS  Google Scholar 

  198. Pathak MA, Allen B, Ingram DJE, Fellman JH (1961) Photosensitization and the Effect of Ultraviolet Radiation on the Production of Unpaired Electron in Presence of Furocoumarins (Psoralen). Biochem Biophys Acta 54: 506

    CAS  Google Scholar 

  199. Pathak MA, Riley FC, Fitzpatrick TB (1962) Melanogenesis in Human Skin Following Exposure to Long-Wave Ultraviolet and Visible Light. J Invest Dermatol 39: 435

    CAS  Google Scholar 

  200. Pathak MA, Fitzpatrick TB (1974) In: Fitzpatrick TB, Pathak MA, Harber LC, Seiji M, Kukita A (eds.) Sunlight and Man, p. 725. University of Tokyo, Tokyo

    Google Scholar 

  201. Patil DG, Chedekel MR (1984) Synthesis and Analysis of Pheomelanin Degradation Products. J Org Chem 49: 997; and refs. therein

    CAS  Google Scholar 

  202. Pawelek J, Korner A, Bergstrom A, Bologna J (1980) New Regulators of Melanin Biosynthesis and the Autodestruction of Melanoma Cells. Nature 286: 617; and refs. therein

    CAS  Google Scholar 

  203. Pawelek JM (1990) Dopachrome Conversion Factor Functions as an Isomerase. Biochim Biophys Res Commun 166: 1328

    CAS  Google Scholar 

  204. Pawelek J (1991) After Dopachrome? Pigment Cell Res 4: 53

    CAS  Google Scholar 

  205. Peranio C, Lamar Jr C, Pitot HC (1966) Studies on the Mechanism of Carbohydrate Repression in Rat Liver (Review). Adv Enzym Regul 4: 199

    Google Scholar 

  206. Piattelli M, Fattorusso E, Magno S, Nicolaus RA (1963) The Structure of Melanins and Melanogenesis, III: The Structure of Sepiomelanin. Tetrahedron 19: 2061; and refs. therein

    CAS  Google Scholar 

  207. Pittner RA, Fears R, Brindley DN (1985) Effects of cAMP, Glucocorticoids and Insulin on the Activities of Phosphatidate Phosphohydrolase, Tyrosine Aminotransferase and Glycerol Kinase in Isolated Rat Hepatocytes in Relation to the Control of Triglycerol Synthesis and Gluconeogenesis. Biochem J 225: 455

    CAS  Google Scholar 

  208. Price JE, Tarin D, Fidler IJ (1988) Influence of Organ Microenvironment on Pigmentation of a Metastatic Murine Melanoma. Cancer Res 48: 2258

    CAS  Google Scholar 

  209. Proctor P, McGinness J, Corry P (1974) A Hypothesis on the Preferential Destruction of Melanized Tissues. J Theor Biol 48: 19

    CAS  Google Scholar 

  210. Prota G (1988) In: Bagnata H (ed.) Advances in Pigment Cell Research, p. 101. Academic Press, New York

    Google Scholar 

  211. Prota G, d’Ischia M, Napolitano A (1988) The Regulatory Role of Sulphydryl Compounds in Melanogenesis. Pigment Cell Res 1S: 48

    Google Scholar 

  212. Prota G (1992) Melanins and Melanogenesis. Academic Press, San Diego

    Google Scholar 

  213. Prota G (1995) The Chemistry of Melanins and Melanogenesis In: Herz W, Falk H, Kirby GW (eds.) Fortschr Chem Organ Naturstoffe, Vol. 64, p. 93. Springer, Wien New York

    Google Scholar 

  214. Pullman A, Pullman B (1961) The Band Structure of Melanins. Biochim Biophys Acta 54: 384

    CAS  Google Scholar 

  215. Quevedo Jr WC, Szabo G, Birks J, Sinesi SJ (1965) Melanocyte Populations in UV-Radiated Human Skin. J Invest Dermatol 45: 295

    Google Scholar 

  216. Quevedo WC, Fitzpatrick TB, Pathak MA, Jimbow K (1974) Light and Skin Colour. In: Pathak MA, Herber LC, Seiji M, Kukita A, Fitzpatrick TB (eds.) Sunlight and Man, p. 165. Tokyo University Press, Tokyo

    Google Scholar 

  217. Ramaiah A (1994) Vitiligo. J Ind Chem Soc 71: 355

    CAS  Google Scholar 

  218. Raper HS (1928) The Aerobic Oxidases. Physiol Rev 8: 245

    CAS  Google Scholar 

  219. Raper HS (1938) Some Problems of Tyrosine Melabolism. J Chem Soc: p. 125

    Google Scholar 

  220. Remers WA (1972) Properties and Reactions of Indoles. In: Houlihan WI (ed.) Indoles, Part I, p. 152. Wiley, New York

    Google Scholar 

  221. Repine JE, Pfenninger OW, Talmage DW, Berger EM, Pettijohn DE (1981) Dimethyl Sulfoxide Prevents DNA Nicking Mediated by Ionizing Radiation or Iron/Hydrogen Peroxide-Generated Hydroxyl Radicals. Proc Natl Acad Sci USA 78: 1001

    CAS  Google Scholar 

  222. Riley PA (1970) Mechanism of Pigment Cell Toxicity Produced by Hydroxyanisol. J Pathol 101: 163

    CAS  Google Scholar 

  223. Robb DA (1984) Tyrosinase. In: Loutie R (ed.) Copper Proteins, Vol. 2, p. 207. Florida CRC Press, Boca Raton

    Google Scholar 

  224. Robson NC, Swan GA (1966) Studies on the Structure of Some Synthetic Melanins. In: Della Prota G, Muhlbock O (eds.) Structure and Control of the Melanocytes, p. 155. Springer, Berlin Heidelberg New York

    Google Scholar 

  225. Rudowska I (1965) Studies on the Mechanism of Psoralens in the Treatment of Vitiligo (Polish). Prezeglad Dermatologiczny 52: 391

    CAS  Google Scholar 

  226. Rodriguez-Lopez JN, Tudela J, Varon R, Garcia-Canovas F (1991) Kinetic Study on the Effect of pH on the Melanin Biosynthesis Pathway. Biochim Biophys Acta 1076: 379

    CAS  Google Scholar 

  227. Rorsman H, Albertson E, Edholm LE, Hansson C, Ogren L, Rosengren E (1988) Thiols in the Melanocyte. Pigment Cell Res 1S: 54

    Google Scholar 

  228. Rosel MA, Mosca L, DeMarco C (1992) Melanin Production from Enkephalins by Tyrosinase. Biochem Biophys Res Commun 184: 1190

    Google Scholar 

  229. Ross GT, Odell WD (1963) The Effects of Temperature on the Response to Melanocytes-Stimulating Hormone. Ann NY Acad Sci 100: 696

    CAS  Google Scholar 

  230. Roy S, Chakraborty AK, Chakraborty DP (1981) Melanin Formation and Breakdown of Indole Under Udenfriend Conditions. J Ind Chem Soc 58: 992

    CAS  Google Scholar 

  231. Roychowdhury Jr A, Chakraborty DP (1957) Psoralen Therapy in Leucoderma. Cal Med J 54: 139

    Google Scholar 

  232. Roychowdhury SK, Chakraborty DP (1968) Some Urinary Indole Profile of Vitiliginous Patients. Clin Chim Acta 22: 298

    Google Scholar 

  233. Sarna T, Froncisz W, Hyde JS (1980) Cu2+ Probe of Metal-Ion Binding Sites in Melanin Using Electron Paramagnetic Resonance Spectroscopy. Natural Melanin II. Arch Biochem Biophys 202: 304; and refs. therein

    CAS  Google Scholar 

  234. Sarna T, Duleba A, Korytowski W, Swartz H (1980) Interaction of Melanin with Oxygen. Arch Biochem Biophys 200: 140

    CAS  Google Scholar 

  235. Sarna T, Menon IA, Sealy RC (1984) Photoinduced Oxygen Consumption in Melanin Systems-II. Action Spectra and Quantum Yields for Phaeomelanins. Photochem Photobiol 39: 805

    CAS  Google Scholar 

  236. Sarna T, Korytowski W, Sealy RC (1985) Nitroxides as Redox Probe of Melanins: Dark-Induced and Photo-Induced Changes in Redox Equilibria. Arch Biochem Biophys 239: 266

    Google Scholar 

  237. Sarna T (1992) Properties and Function of the Ocular Melanin: A Photobiophysical View. J Photochem Photobiol B12: 215

    Google Scholar 

  238. Schally AV, Kastin AJ, Redding TW, Bowers CY, Yaijma H, Kubo K (1967) Thyroid Stimulating and Pigmentary Effects of Synthetic Peptides Related to α-MSH and ACTH. Metabolism 16: 824

    CAS  Google Scholar 

  239. Sealy RC, Felix CC, Hyde JS, Swartz HM (1980) Structure and Reactivity of Melanins: Influence of Free Radicals and Metal Ions. In: Pryor WA (ed.) Free Radicals in Biology, Vol. 4, p. 209. Academic Press, New York

    Google Scholar 

  240. Sealy RC, Sarna T, Wanner EJ, Reszka K (1984) Photosensitization of Melanin: An Electron Spin Resonance Study of Sensitized Radical Production and Oxygen Consumption. Photochem Photobiol 40: 453

    CAS  Google Scholar 

  241. Sehgal VN (1975) A Comparative Clinical Evolution of Trimethylpsoralen, Psoralen, and 8-Methoxypsoralen in Treating Vitiligo. Int J Dermatol 14: 205

    CAS  Google Scholar 

  242. Seiji M, Fitzpatrick TB, Birbeck MS (1961) The Melanosome: A Distinctive Subcellular Particle of Mammalian Melanocytes and the Site of Melanogenesis. J Invest Dermatol 36: 243

    CAS  Google Scholar 

  243. Seiji M, Fitzpatrick TB (1961) The Reciprocal Relationship Between Melanization and Tyrosinase Activity in Melanosomes (Melanin Granules). J Biochem 49: 700

    CAS  Google Scholar 

  244. Seiji M, Fitzpatrick TB, Simpson RT, Birbeck MSC (1963) Chemical Composition and Terminology of Specialized Organelles (Melanosomes and Melanin Granules) in Mammalian Melanocytes. Nature 197: 1082

    CAS  Google Scholar 

  245. Seiji M, Iwashita S (1966) Intracellular Localization of Tyrosinase and Site of Melanin Formation in Melanocyte. J Invest Dermatol 45: 305

    Google Scholar 

  246. Seiji M, Sasaki M, Tomita Y (1978) Nature of Tyrosinase Inactivation in Melanosomes. Tohoku J Exp Med 125: 233

    CAS  Google Scholar 

  247. Shibata T, Prota G, Mishima Y (1993) Non-Melanosomal Regulatory Factors in Melanogenesis. J Invest Dermatol 100: 274S

    CAS  Google Scholar 

  248. Sinha Roy SP, Chakraborty DP (1976) Psoralen, a Powerful Germination Inhibitor. Phytochemistry 15: 1205

    Google Scholar 

  249. Slominski A, Moellmann G, Kuklinska E, Bomirski A, Pawelek J (1988) Positive Regulation of Melanin Pigmentation by Two Key Substrates of the Melanogenic Pathway, L-Tyrosine and L-Dopa. J Cell Sci 89: 287

    CAS  Google Scholar 

  250. Slominski A (1989) L-Tyrosine Induces Synthesis of Melanogenesis-Related Proteins. Life Sci 45: 1799

    CAS  Google Scholar 

  251. Slominski A, Costantino R (1991) L-Tyrosine Induces Tyrosinase Expression via a Posttranscriptional Mechanism. Experientia 47: 721

    CAS  Google Scholar 

  252. Slominski A, Costantino R (1991) Molecular Mechanism of Tyrosinase Regulation by L-Dopa in Hamster Melanoma Cells. Life Sci 48: 2075

    CAS  Google Scholar 

  253. Snell RS, Bischitz PG (1960) The Effect of Large Doses of Estrogen and Progesterone on Melanin Pigmentation. J Invest Dermatol 35: 73

    CAS  Google Scholar 

  254. Snell RS (1961) The Influence of Sex Hormones on Melanin Pigmentation of the Skin. Biochem J 78: 17

    Google Scholar 

  255. Snell RS (1962) Effect of Progesterone on the Activity of Melanocytes in the Skin. Z Zellforsch Mikroskop Anat 57: 818

    CAS  Google Scholar 

  256. Snell RS (1965) Effect of Melatonin on Mammalian Epidermal Melanocytes. J Invest Dermatol 44: 273

    CAS  Google Scholar 

  257. Staricco RJ, Pinkus H (1957) Quantitative and Qualitative Data on the Pigment Cells of Adult Human Epidermis. J Invest Dermatol 28: 33

    CAS  Google Scholar 

  258. Sugumaran M, Semenst V (1990) Formation of a Stable Quinone Methide During Tyrosinase-Catalyzed Oxidation of Alpha-Methyldopa Methyl Ester and Its Implication in Melanin Biosynthesis. Bioorg Chem 18: 144

    CAS  Google Scholar 

  259. Sugumaran M (1992) Letter to the Editor. Pigment Cell Res 5: 203

    CAS  Google Scholar 

  260. Swan GA, Waggott A (1970) Studies Related to the Chemistry of Melanins. Part X: Quantitative Assessment of Different Types of Units Present in Dopa-Melanin. J Chem Soc (C) (London): p. 1409

    Google Scholar 

  261. Swan G (1973) Current Knowledge of Melanin Structure. In: McGovern VJ, Russell P (eds.) Pigment Cell, Vol. 1, p. 151. Karger, Basel

    Google Scholar 

  262. Swan GA (1974) Structure, Chemistry and Biosynthesis of the Melanins. In: Herz W, Grisebach H, Kirby GW (eds.) Fortschr Chem Organ Naturstoffe, Vol. 31, p. 521. Springer, Wien New York

    Google Scholar 

  263. Szabo G (1967) Tyrosinase in the Epidermal Melanocytes of White Human Skin. Arch Dermatol 76: 324

    Google Scholar 

  264. Takenouchi K (1963) Thiamine and Riboflavine Metabolism in Skin Disease. Toda Printing Company, Chiba City, Japan

    Google Scholar 

  265. Takenouchi K, Aso K (1964) The Relation Between Melanin Formation and Ascorbic Acid. J Vitamin (Kyoto) 10: 123

    CAS  Google Scholar 

  266. Tenconi LT, Acocella G (1966) Study on the Chemotherapy of Experimental Lead Poisoning. 1. Effects of Lead Poisoning on the Tryptophan to Nicotinic Acid Metabolism in the Rat. Acta Vitaminologica 20: 189

    CAS  Google Scholar 

  267. Thomas M (1955) Melanins. In: Peach K, Trecey MV (eds.) Modern Methods of Plant Analysis. Vol. IV, p. 661. Springer, Berlin Göttingen Heidelberg

    Google Scholar 

  268. Thomson RH (1974) The Pigments of Raddish Hair and Feathers. Angew Chem Int Ed Engl 13: 305

    CAS  Google Scholar 

  269. Thomson RH (1962) Melanins. In: Florkin M, Mason HS (eds.) Comparative Biochemistry, Vol. VIII, Part A, p. 727. Academic Press, New York London

    Google Scholar 

  270. Toda K, Hory Y, Fitzpatrick TB (1969) The Site of Tyrosinase Activity Within the Melanosome (Abstr). J Invest Dermatol 52: 380

    Google Scholar 

  271. Tomita Y, Hariu A, Mizuno C, Seiji M (1980) Inactivation of Tyrosinase by Dopa. J Invest Dermatol 75: 379

    CAS  Google Scholar 

  272. Tomita Y, Fukushima M, Tagami H (1987) In: Jimbow K (ed.) Structure and Function of Melanin. Vol. 4, p. 14. Fuji Shoin Co. Ltd., Sapporo, Japan

    Google Scholar 

  273. Tompsett D (1939) Memoirs on Typical British Marine Plants and Animals, Vol. XXXII. University Press, Liverpool

    Google Scholar 

  274. Toshima S, Moore GE, Sandberg AA (1968) Ultrastructure of Human Melanoma in Cell Culture: Electron Microscopic Studies. Cancer 21: 202

    CAS  Google Scholar 

  275. Udenfriend S, Clark CT, Axelrod J, Brodie BB (1954) Ascorbic Acid in Aromatic Hydroxylation. 1. A Model System for Aromatic Hydroxylation. J Biol Chem 208: 731

    CAS  Google Scholar 

  276. Ullrich V, Staudinger HJ (1966) In: Bloch K, Hayaishi O (eds.) Biological and Chemical Aspects of Oxygenases, p. 235. Maruzen, Tokyo

    Google Scholar 

  277. Ullrich V, Duppel W (1975) Iron and Copper Containing Monooxigenases. In: Boyer PD (ed.) The Enzymes, Vol. XII, p. 253. Academic Press, New York London

    Google Scholar 

  278. Venneste WH, Zuberbuhler A (1974) In: Hayaishi O (ed.) Molecular Mechanisms of Oxygen Activation, p. 371. Academic Press, New York; and refs. therein

    Google Scholar 

  279. Voorhees JJ, Duell EG, Bass LJ, Harrell ER (1973) Role of Cyclic AMP in the Control of Epidermal Cell Growth and Differentiation, Chalones: Concepts and Current Researches. Natal Cancer Inst Monogr 38: 47; and refs. therein

    CAS  Google Scholar 

  280. Walaas E (1963) The Chemical Transformation of the Chatecholamines Induced by UV Irradiation. Photochem Photobiol 2: 9

    CAS  Google Scholar 

  281. Wheeler MH, Bell AA (1988) Melanins and Their Importance in Pathogenic Fungi. Curr Top Med Mycol 7: 338

    Google Scholar 

  282. Whitney WD (1905) Atharva Veda Samhita (Translation and Notes). Harvard Oriental Series, Vol. 7. Harvard University Press, Lanman, Mass

    Google Scholar 

  283. White R, Hu F (1977) Characteristics of Tyrosinase in B 16 Melanoma. J Invest Dermatol 68: 272

    CAS  Google Scholar 

  284. Wolfram LJ, Berthiaume M (1985) 6th Eur Workshop Melanin Pigm

    Google Scholar 

  285. Woods M, Du Buy H, Burk D (1950) Evidence for the Mitochondrial Nature and Function of Melanin Granules. Zoologica 35: 30

    Google Scholar 

  286. Wurtman RJ, Axelrod J (1966) Effect of Chlorpromazine and Other Drugs on the Disposition of Circulating Melatonin. New Eng J Med: p. 274

    Google Scholar 

  287. Yasunobu KT, Peterson EW, Mason HS (1959) The Oxidation of Tyrosine-Containing Peptides by Tyrosinase. J Biol Chem 234: 3291

    CAS  Google Scholar 

  288. Young TE, Oriswold JR, Hulbert MH (1974) Melanin. 1: Kinetics of Oxidative Cyclization of Dopa to Dopachrome. J Org Chem 39: 1980

    CAS  Google Scholar 

  289. Young TE, Babbitt BW, Wolfe LA (1980) Melanin. 2. Electrochemical Study of the Oxidation of α-Methyldopa and 5,6-Dihydroxy-2-methylindole. J Org Chem 45: 2899

    CAS  Google Scholar 

  290. Young TE, Babbitt BW (1983) Electrochemical Study of the Oxidation of α-Methyldopamine, α-Methylnoradrenaline, and Dopamine. J Org Chem 48: 562

    CAS  Google Scholar 

  291. Zeise L, Chedekel MR (1992) Melanin Standard Method: Titrimetric Analysis. Pigment Cell Res 5: 230

    CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Natural Products, 8, J. N. Roy Lane, Kolkata, 700006, India

    Shyamali Roy

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  1. Shyamali Roy
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  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz

  2. Institut für Chemie, Johannes-Kepler-Universität, Linz, Austria

    H. Falk

  3. Chemistry Department, The University of Glasgow, Glasgow, Scotland

    G. W. Kirby

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Roy, S. (2007). Melanin, Melanogenesis, and Vitiligo. In: Herz, W., Falk, H., Kirby, G.W. (eds) Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 88. Springer, Vienna. https://doi.org/10.1007/978-3-211-49389-2_3

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