Toxicological Aspects of Melanin and Melanogenesis

The Pigmentary System: Physiology and Pathophysiology: Second Edition

Volumn , Issue , 2007, Pages 354-394

  Land, Edward J ^a   Ramsden, Christopher A ^a   Riley, Patrick A ^b  

^a KEELE UNIVERSITY   (United Kingdom)

^b Totteridge Institute for Advanced Studies   (United Kingdom)

Author keywords

Cysteinyldopa; Dopaquinone; Melanocyte depletion; Melanogenesis; Oxidative stress

Indexed keywords

EID: 84889624828     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470987100.ch18     Document Type: Chapter

References (423)

1. Abdel-Malek, Z., V. B. Swope, N. Amornsiripanitch, and J. J. Nordlund. In vitro modulation of proliferation and melanization of S91 melanoma cells by prostaglandins. Cancer Res. 47:3141-3146, 1987.
2. Abdel-Malek, Z., V. B. Swope, J. Pallas, K. Krug, and J. J. Nordlund. Mitogenic, melanogenic and cAMP responses of cultured neonatal human melanocytes to commonly used mitogens. J. Cell. Physiol. 150:416-425, 1992.
3. Abe, H., N. Ohya, K. F. Yamamoto, T. Shibuya, S. Arichi, and S. Odashima. Effects of glycyrrhizin and glycyrrhetinic acid on growth and melanogenesis in cultured B16 melanoma cells. Eur. J. Cancer Clin. Oncol. 23:1549-1555, 1987.
4. Agarwal, R., E. E. Medrano, I. U. Khan, J. J. Nordlund, and H. Mukhtar. Metabolism of benzo(A)pyrene by human melanocytes in culture. Carcinogenesis 12:1963-1966, 1991.
5. Albert, A. Selective Toxicity: The Physicochemical Basis of Therapy, 7th edn. London: Chapman and Hall, 1985, pp. 469-475.
6. Albert, D. M., C. A. Puliafito, A. B. Fulton, N. L. Robinson, Z. N. Zakov, T. P. Dryja, A. B. Smith, E. Egan, and S. S. Leffingwell. Increased incidence of choroidal malignant melanoma occurring in a single population of chemical workers. Am. J. Ophthalmol. 89:323-337, 1980.
7. Anders, A., H. Gröger, F. Anders, C. Zechel, and A. Smith. Discrimination of initiating and promoting carcinogens in fish. Ann. Rech. Vet. 22:273-294, 1991.
8. Ando, H., M. Oka, M. Ichihashi, and Y. Mishima. Protein kinase C and linoleic acid-induced inhibition of melanogenesis. Pigment Cell Res. 3:200-206, 1990.
9. Ando, S., O. Ando, Y. Suemoto, and Y. Mishima. Tyrosinase gene transcription and its control by melanogenic inhibitors. J. Invest. Dermatol. 100:150S-155S, 1993.
10. Appelgren, L.-E., U. Bondesson, E. Fredriksson, C. Ingvast Larsson, and D. S. Jansson. Analysis of hair samples for clenbuterol: A possibility to detect illegal use in calves. In: Proceedings of the 6th International EAVPT Congress, Edinburgh, 1994, P. Lees (ed.). Oxford: Blackwell Scientific Publications, 1994 a, p. 272.
11. Appelgren, L.-E., C. Ingvast Larsson, D. S. Jansson, and B. S. Larsson. Pigment affinity of clenbuterol. Distribution studies of labelled clen-buterol in mice using autoradiography. In: Proceedings of the 6th International EAVPT Congress, Edinburgh, 1994, P. Lees (ed.). Oxford: Blackwell Scientific Publications, 1994 b, p. 276.
12. Arnold, J., P. Anthonioz, and J. P. Marchand. Depigmenting action of corticosteroids. Experimental study on guinea pigs. Dermatologica 151:274-280, 1975.
13. Aubert, C., and C. Bohuon. Depigmentation of the golden hamster by oral 9,10-dimethyl-1,2-benzanthracene administration. C. R. Acad. Sci. 271:281-284, 1970.
14. Austin, D. F., and P. Reynolds. Occupation and malignant melanoma of the skin. Recent results. Cancer Res. 102:98-107, 1986.
15. Aw, T. C., and E. Boyland. Depigmentation of hair in mice due to intradermal injections of a tumour promoter, 12-O-tetradeca-noylphorbol-13-acetate (TPA). ĨRCS Medical Science: Library Compendium 6:213, 1978.
16. Aw, T. C., and E. Boyland. Depigmentation of hair in mice by chemicals. ĨRCS Medical Science: Library Compendium 9:29-30, 1981.
17. Aw, T. C., R. G. Bird, and E. Boyland. Histology of chemically induced depigmentation of hair in mice. ĨRCS Medical Science: Library Compendium 10:403-404, 1982.
18. Axelrod, J., and A. B. Lerner. O-methylation in the conversion of tyrosine to melanin. Biochim. Biophys. Acta 71:650-655, 1963.
19. Bachem, A. Ophthalmic ultraviolet action spectra. Am. J. Ophthalmol. 41:969-975, 1956.
20. Barbeau, A., L. Dallaire, N. T. Buu, J. Poirier, and E. Rucinska. Comparative behavioral biochemical and pigmentary effects of MPTP, MPP+ and paraquat in Rana pipiens. Life Sci. 37:1529-1538, 1985.
21. Barden, H., and S. Levin. Histochemical observations on rodent brain melanin. Brain Res. Bull. 10:847-851, 1983.
22. Barishak, Y. R., A. M. Beemer, M. N. Egyed, A. Shlosberg, and A. Eilat. Histology of the iris in geese and ducks photosensitized by ingestion of ammi majus seeds. Acta Ophthalmol. 53:585-590, 1975.
23. Barsa, J. A., J. C. Newton, and J. C. Saunders. Lenticular and corneal opacities during phenothiazine therapy. J. Am. Med. Assoc. 193:10-12, 1965.
24. Barthel, E. Erhöhte Mortalität an Osophaguskrebs, Magenkrebs und Hautmelanom bei Pestizid-exponierten Schädlingsbekämpfern in der DDR. Arch. Geschwulstforsch. 55:481-488, 1985.
25. Baumgartner, A. M., P. F. Jones, W. A. Baumgartner, and C. T. Black. Radioimmunoassay of hair for determining opiate-abuse histories. J. Nucl. Med. 20:748-752, 1979.
26. Beierwaltes, W. H., L. M. Lieberman, V. M. Varma, and R. E. Counsell. Visualizing human malignant melanoma and metastases. Use of chloroquine analog tagged with iodine 125. J. Am. Med. Assoc. 206:97-102, 1968.
27. Benedetto, J.-P., J.-P. Ortonne, and C. Voulot. Role of thiol compounds in mammalian melanin pigmentation: part I. J. Invest. Dermatol. 77:402-405, 1981.
28. Benedetto, J. P., J. P. Ortonne, C. Voulot, C. Khatchadourian, G. Prota, and J. Thivolet. Role of thiol compounds in mammalian melanin pigmentation. II. Glutathione and related enzymatic activities. J. Invest. Dermatol. 79:422-424, 1982.
29. Ben-Shachar, D., and M. B. H. Youdim. Iron, melanin and dopamine interaction: relevance to Parkinson's disease. Prog. Neuro-Psychopharmacol. Biol. Psychiatr. 17:139-150, 1993.
30. Bergman, K. Autoradiographic distribution of 14C-labeled 3H-imidazo(4,5-f)quinoline-2-amines in mice. Cancer Res. 45:1351-1356, 1985.
31. Berkelhammer, J., R. W. Oxenhandler, R. R. J. Hook, and J. M. Hennessey. Development of a new melanoma model in C57Bl/6 mice. Cancer Res. 42:3157-3163, 1982.
32. Bernstein, H. N., and J. Ginsberg. The pathology of chloroquine retinopathy. Arch. Ophthalmol. 71:238-245, 1964.
33. Bhatnagar, V., S. Anjaiah, N. Puri, B. N. Arudhra Darshanam, and A. Ramaiah. pH of melanosomes of B16 murine melanoma is acidic: its physiological importance in the regulation of melanin biosynthesis. Arch. Biochem. Biophys. 307:183-192, 1993.
34. Bleehen, S. S., M. A. Pathak, Y. Hori, and T. B. Fitzpatrick. Depigmentation of skin with 4-isopropylcatechol, mercaptoamines and other compounds. J. Invest. Dermatol. 50:103-117, 1968.
35. Blois, M. S. Preliminary note. Melanoma detection with radio-iodoquine. J. Nucl. Med. 9:492-493, 1968.
36. Blois, M. S. J., and R. F. Kallman. The incorporation of C14 from 3,4-dihydroxyphenylalanine-2'-C14 into the melanin of mouse melanomas. Cancer Res. 24:863-868, 1964.
37. Bolt, A. G., and I. S. Forrest. Interaction between human melanopro-tein and chlorpromazine derivatives II. Spectrophotometric studies. Life Sci. 6:1285-1292, 1967.
38. Borg, K., and H. Tjälve. Effect of thiram and dithiocarbamate pesticides on the gastrointestinal absorption and distribution of nickel in mice. Toxicol. Lett. 42:87-98, 1988.
39. Borovansky, J., P. Mirejovsky, and P. A. Riley. Possible relationship between abnormal melanosome structure and cytotoxic phenomena in malignant melanoma. Neo-plasma 38:393-400, 1991.
40. Boyland, E., J. W Clegg, P. C. Koller, E. Rhoden, and O. H. Warwick. The effect of chloroethylamines on tumours, with special reference to bronchogenic carcinoma. Br. J. Cancer 2:17-29, 1948.
41. Brandt, I., J.-À. Gustafsson, and J. Rafter. Distribution of the carcinogenic tryptophan pyrolysis product Trp-P-1 in control, 9-hydroxyellipticine and beta-nap hthoflavone pretreated mice. Carcinogenesis 4:1291-1296, 1983.
42. Brandt, I., B. Kowalski, J.-À. Gustafsson, and J. Rafter. Tissue localization of the carcinogenic glutamic acid pyrolysis product GLU-P-1 in control and beta-naphthoflavone-treated mice and rats. Carcinogenesis 10:1529-1533, 1989.
43. Brooks, D. W, and C. R. Dawson. Aspects of tyrosinase chemistry. In: The Biochemistry of Copper, J. Peisach, P. Aisen, and W. E. Blumberg (eds). New York: Academic Press, 1966, pp. 343-357.
44. 125I]-5-iodo-2-thiouracil in cultured hamster, rabbit, and human melanoma cells. Cancer Res. 43:1316-1320, 1983.
45. Brun, R. Contribution a l'étude de la depigmentation experimentale. Bull. Inst. Nat. Genevois 61:3-97, 1961.
46. Burchill, S. A., and A. J. Thody. DOPAminergic inhibition of tyrosinase activity in hair follicular melanocytes of the mouse. J. Endocrinol. 111:233-237, 1986.
47. Burnett, J. B. The tyrosinases of mouse melanoma: isolation and molecular properties. J. Biol. Chem. 246:3079-3091, 1971.
48. Burns, R. P. Delayed onset of chloroquine retinopathy. N. Engl. J. Med. 275:693-696, 1966.
49. Bus, J. S., S. Z. Cagen, M. Olgaard, and J. E. Gibson. A mechanism of paraquat toxicity in mice and rats. Toxicol. Appl. Pharmacol. 35:501-513, 1976.
50. Carlsson, A. Biochemical aspects of abnormal movements induced by L-dopa. In: L-Dopa and Parkinsonism, A. Barbeau, and F. H. McDowell (eds). Philadelphia: F. A. Davis Co., 1970, pp. 205-213.
51. Carlsson, J., S. Sjöberg, and B. S. Larsson. Present status of boron neutron capture therapy. Acta Oncol. 31:803-813, 1992.
52. Carr, J. G. Production of mutations in mice by 1:2:5:6-dibenzanthracene. Br. J. Cancer 1:152-156, 1947.
53. Carsberg, C. J., H. M. Warenius, and P. S. Friedmann. Ultraviolet radiation-induced melanogenesis in human melanocytes. Effects of modulating protein kinase C. J. Cell Sci. 107:2591-2597, 1994.
54. Chakraborty, A. K., and D. P. Chakraborty. The effect of tryptophan on dopa-oxidation by melanosomal tyrosinase. Int. J. Biochem. 25:1277-1280, 1993.
55. Chavin, W, and W. Schlesinger. Some potent melanin depigmentary agents in the black goldfish. Naturwissenschaften 53:413-414, 1966.
56. Chedekel, M. R., E. J. Land, A. Thompson, and T. G. Truscott. Early steps in the free radical polymerization of 3,4-dihydroxyphenylalanine (dopa) to melanin. J. Chem. Soc. Chem. Commun., 1170-1172, 1984.
57. Chen, Y. M., and W. Chavin. Melanogenesis in human melanomas. Cancer Res. 35:606-612, 1975.
58. Chian, L. T. Y., and G. F. Wilgram. Tyrosinase inhibition; its role in suntanning and albinism. Science 155:198-200, 1967.
59. Chiba, K., A. Trevor, and N. Castagnoli, Jr. Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 120:574-578, 1984.
60. Chiueh, C. C., S. P. Markey, R. S. Burns, J. Johannessen, D. M. Jacobowitz, and I. J. Kopin. N-methyl-4-phenyl-1,2,3,6-tetrahy-dropyridine, a parkinsonian syndrome causing agent in man and monkey, produces different effects in guinea pig and rat. Pharmacologist 25:131, 1983.
61. Christensen, E., J. E. Möller, and A. Faurbye. Neuropathological investigation of 28 brains from patients with dyskinesia. Acta Psy-chiatr. Scand. 46:14-23, 1970.
62. Clews, J., C. J. Cooksey, P. J. Garratt, E. J. Land, C. A. Ramsden, and P. A. Riley. Oxidative cyclisation of N, N-dialkylcatechol amines to hetrocyclic betaines via o-quinones: synthetic, pulse radiolytic and enzyme studies. J. Chem. Soc., Perkin Trans. I:4306-4315, 2000.
63. Coderre, J. A., J. D. Glass, R. G. Fairchild, U. Roy, S. Cohen, and I. Fand. Selective targeting of boronophenylalanine to melanoma in BALB/c mice for neutron capture therapy. Cancer Res. 47:6377-6383, 1987.
64. Cohen, M. B., R. E. Saxton, R. R. Lake, R. Cagle, L. S. Graham, A. Nizze, L. S. Yamada, M. Gan, G. Bronca, K. Greenwell, and D. L. Morton. Detection of malignant melanoma with iodine-123-iodoamphetamine. J. Nucl. Med. 29:1200-1206, 1988.
65. Coleman, D. L. Effect of genic substitution on the incorporation of tyrosine into the melanin of mouse skin. Arch. Biochem. Biophys. 96:562-568, 1962.
66. Connor, M. J., and L. A. Wheeler. Depletion of cutaneous glutathione by ultraviolet radiation. Photochem. Photobiol. 46:239-245, 1987.
67. Cooksey, C. J., E. J. Land, P. A. Riley, T. Sarna, and T. G. Truscott. On the interaction of anisyl-3,4-semiquinone with oxygen. Free Rad. Res. Commun. 4:131-138, 1987.
68. Cooksey, C. J., K. Jimbow, E. J. Land, and P. A. Riley. Reactivity of orthoquinones involved in tyrosinase-dependent cytotoxicity: differences between alkylthio-and alkoxy-substituents. Melanoma Res. 2:283-293, 1992.
69. Cooksey, C. J., E. J. Land, C. A. Ramsden, and P. A. Riley. Tyrosinase-mediated cytotoxicity of 4-substituted phenols: quantitative structure-thiol-reactivity relationships of the derived o-quinones. Anti-Cancer Drug Des. 10:119-129, 1995.
70. Cooksey, C. J., E. J. Land, F. A. P. Rushton, C. A. Ramsden, and P. A. Riley. Tyrosinase-mediated cytotoxicity of 4-substituted phenols: the use of QSAR to forecast reactivities of thiols towards the derived orthoquinones. Quant. Struct.-Act. Relat. 15:498-503, 1996.
71. Cooksey, C. J., P. J. Garratt, E. J. Land, S. Pavel, C. A. Ramsden, P. A. Riley, and N. P. M. Smit. Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase. J. Biol. Chem. 272: 26226-26235, 1997.
72. Coote, N., and L. U. Abeysiri. Skin depigmentation associated with intravenous anaesthetic agents. Anaesthesia 34:336-338, 1979.
73. Cotzias, G. C., P. S. Papavasiliou, and S. T. Miller. Manganese in melanin. Nature 201:1228-1229, 1964.
74. Dale, A. J. D., E. M. Parkhill, and D. D. Layton. Studies on chloroquine retinopathy in rabbits. J. Am. Med. Assoc. 193:241-243, 1965.
75. D'Amato, R. J., Z. P. Lipman, and S. H. Snyder. Selectivity of the parkinsonian neurotoxin MPTP: Toxic metabolite MPP+ binds to neuromelanin. Science 231:987-989, 1986.
76. D'Amato, R. J., D. F. Benham, and S. H. Snyder. Characterization of the binding of N-methyl-4-phenylpyridine, the toxic metabolite of the parkinsonian neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, to neuromelanin. J. Neurochem. 48:653-658, 1987.
77. Danielsson, B. R. G., A. Oskarsson, and L. Dencker. Placental transfer and fetal distribution of lead in mice after treatment with dithio-carbamates. Arch. Toxicol. 55:27-33, 1984.
78. De Léobardy, J., and A. Labesse. On the treatment of Addison's disease with cysteine. Presse Med. 42:599-600, 1934.
79. Dencker, L., and N. G. Lindquist. Distribution of labeled chloroquine in the inner ear. Arch. Otolaryngol. 101:185-188, 1975.
80. Dencker, L., N. G. Lindquist, and S. Ullberg. Mechanism of drug-induced chronic otic lesions. Role of drug accumulation on the melanin of the inner ear. Experientia 29:1362-1363, 1973.
81. Dencker, L., B. Larsson, K. Olander, S. Ullberg, and M. Yokota. False precursors of melanin as selective melanoma seekers. Br. J. Cancer 39:449-452, 1979.
82. Dencker, L., B. Larsson, K. Olander, S. Ullberg, and M. Yokota. Incorporation of thiouracil and some related compounds into growing melanin. Acta Pharmacol. Toxicol. 49:141-149, 1981.
83. Dencker, L., B. S. Larsson, K. Olander, and S. Ullberg. A new melanoma seeker for possible clinical use: selective accumulation of radiolabeled thiouracil. Br. J. Cancer 45:95-104, 1982.
84. Dencker, L., B. S. Larsson, R. d'Argy, S. Ullberg, and H. Tjälve. Macro-and micro-autoradiography. Pure Appl. Chem. 63:1271-1277, 1991.
85. Denton, C. R., A. B. Lerner, and T. B. Fitzpatrick. Inhibition of melanin formation by chemical agents. J. Ĩnvest. Dermatol. 18:119-134, 1952.
86. Devi, C. C., C. Tripathi, and A. Ramaiah. pH-dependent interconvertible allosteric forms of murine melanoma tyrosinase: physiological implications. Eur. J. Biochem. 166:705-711, 1987.
87. Devi, C. C., R. K. Tripathi, and A. Ramaiah. pH-dependent interconvertible forms of mushroom tyrosinase with different kinetic properties. Pigment Cell Res. 2:8-13, 1989.
88. Dewar, A. J., C. M. Yates, G. Barron, A. Gordon, H. Wilson, and J. Baker. The effects of chronic chlorpromazine administration on the albino rat retina. Toxicol. Appl. Pharmacol. 43:501-506, 1978.
89. Dewar, W. A., and H. M. Mann. Chloroquine in lupus erythematosus. Lancet 1:780, 1954.
90. Dieke, S. H. Pigmentation and hair growth in black rats as modified by chronic administration of thiourea, phenyl thiourea and α-naphthylthiourea. Endocrinology 40:123-136, 1947.
91. Dietler, C., and K. Lerch. Reaction inactivation of tyrosinase. In: Oxidases and Related Redox Systems, T. E. Kind, M. Morrison, and H. S. Mason (eds). New York: Pergamon Press, 1982, pp. 305-317.
92. D'Ischia, M., A. Napolitano, and G. Prota. Psoralens sensitize glutathione photooxidation in vitro. Biochim. Biophys. Acta 993: 143-147, 1989.
93. Drew, J. F. Concerning the side effects of antimalarial drugs used in the extended treatment of rheumatic disease. Med. J. Aust. 2: 618-620, 1962.
94. Durkacz, B. W., J. Lunec, H. Grindley, S. Griffin, O. Horner, and A. Simm. Murine melanoma cell differentiation and melanogenesis induced by poly(ADP-ribose) polymerase inhibitors. Exp. Cell Res. 202:287-291, 1992.
95. Dürsch, I., H. H. D. Meyer, and H. Karg. Accumulation of the β-agonist clenbuterol by pigmented tissues in rat eye and hair of veal calves. J. Anim. Sci. 73:2050-2053, 1995.
96. Edler, K. Ocular changes associated with chlorpromazine therapy; A preliminary report. Acta Ophthalmol. 44:405-409, 1966.
97. Egyed, M. N., L. Singer, A. Eilat, and A. Shlosberg. Eye lesions in ducklings fed ammi majus seeds. Zbl. Vet.-Med. A 22:764-768, 1975.
98. Englesson, S., B. Larsson, N. G. Lindquist, L. Lyttkens, and J. Stahle. Accumulation of 14C-lidocaine in the inner ear. Acta Otolaryngol. (Stockh.) 82:297-300, 1976.
99. Ephraim, A. I. On sudden or rapid whitening of the hair. Arch. Dermatol. 79:228-235, 1959.
100. Evans, R. D., A. W. Kopf, R. A. Lew, D. S. Rigel, R. S. Bart, R. J. Friedman, and J. K. Rivers. Risk factors for the development of malignant melanoma. Review of case-control studies. J. Dermatol. Surg. Oncol. 14:393-408, 1988.
101. Evans, W. C., and H. S. Raper. The accumulation of L-3,4-dihydroxy-phenylalanine in the tyrosine-tyrosinase reaction. Biochem. J. 31: 2162-2170, 1937.
102. Fairchild, R. G., S. Packer, D. Greenberg, P. Som, A. B. Brill, I. Fand, and W. P. McNally. Thiouracil distribution in mice carrying transplantable melanoma. Cancer Res. 42:5126-5132, 1982.
103. Fairchild, R. G., J. A. Coderre, S. Packer, D. Greenberg, and B. H. Laster. Therapeutic effects of S-35-thiouracil in BALB/c mice carrying Harding-Passey melanoma. Int. J. Radiat. Oncol. Biol. Phys. 17:337-343, 1989.
104. Farishian, R. A., and J. R. Whittaker. Phenylalanine lowers melanin synthesis in mammalian melanocytes by reducing tyrosine uptake: implications for pigment reduction in phenylketonuria. J. Ĩnvest. Dermatol. 74:85-89, 1980.
105. Farooqui, J. Z., E. Robb, S. T. Boyce, G. D. Warden, and J. J. Nordlund. The isolation of a unique melanogenic inhibitor from human skin xenografts: initial in vitro and in vivo characterization. J. Invest. Dermatol. 104:739-743, 1995.
106. Fechner, G. A., J. J. Jacobs, and P. G. Parsons. Inhibition of melano-genesis in human melanoma cells by novel analogues of the partial histamine (H2) agonist nordimaprit. Biochem. Pharmacol. 46:47-54, 1993.
107. Felix, C. C., J. S. Hyde, T. Sarna, and R. C. Sealy. Interactions of melanin with metal ions. Electron spin resonance evidence for chelate complexes of metal ions with free radicals. J. Am. Chem. Soc. 100:3922-3926, 1978.
108. Ferrini, U., A. M. Mileo, and V. J. Hearing. Microheterogeneity of melanosome bound tyrosinase from the Harding-Passey murine melanoma. Ĩnt. J. Biochem. 19:227-234, 1987.
109. Findlay, J. D., and D. M. Jenkinson. Sweat gland function in the Ayrshire calf. Res. Vet. Sci. 5:109-115, 1964.
110. Fisher, P. B., D. R. Prignoli, H. Hermo, I. B. Weinstein, and S. Pestka. Effects of combined treatment with interferon and mezerein on melanogenesis and growth in human melanoma cells. J. Ĩnterferon Res. 5:11-22, 1985.
111. Fitzpatrick, T. B., M. Seiji, and A. D. McGugan. Melanin pigmentation. N. Engl. J. Med. 265:328-331, 1961.
112. 123I-5-iodo-2-thiouracil, a possible radiopharmaceutical for noninvasive detection of ocular melanoma, in melanotic and amelanotic melanomas in hamsters. Nucl. Med. Commun. 6:657-663, 1985.
113. 123I)-5-iodo-2-thiouracil. Ophthalmologica 193:248-254, 1986 a.
114. Franken, N. A. P., A. van Langevelde, E. K. J. Pauwels, J. G. Journée-de Korver, C. N. M. Bakker, and J. A. Oosterhuis. Radioiodine-labelled 5-iodo-2-thiouracil: a potential radiopharmaceutical for establishing the viability of ocular melanoma after radiation therapy. Nucl. Med. Commun. 7:797-809, 1986 b.
115. Frenk, E. Irreversible depigmentation of skin following acute contact eczema caused by adhesive plaster. Hautarzt 31:639-643, 1980.
116. Frenk, E., M. A. Pathak, G. Szabo, and T. B. Fitzpatrick. Selective action of mercaptoamines on melanocytes in mammalian skin. Arch. Dermatol. 97:465-477, 1968.
117. Friedmann, P. S., and B. A. Gilchrest. Ultraviolet radiation directly induces pigment production by cultured human melanocytes. J. Cell. Physiol. 133:88-94, 1987.
118. 2+ probe of metal-ion binding sites in melanin using electron paramagnetic resonance spectroscopy. Arch. Biochem. Biophys. 202:289-303, 1980.
119. Gabel, D. Tumor-seeking compounds for boron neutron capture therapy: synthesis and biodistribution. In: Clinical Aspects of Neutron Capture Therapy, R. G. Fairchild, V. P. Bond, and A. D. Woodhead (eds). New York: Plenum Press, 1989, pp. 233-241.
120. Gan, E. V., H. F. Haberman, and I. A. Menon. Electron transfer properties of melanin. Arch. Biochem. Biophys. 173:666-672, 1976.
121. Goar, E. L., and M. C. Fletcher. Toxic chorioretinopathy following the use of NP 207. Am. J. Ophthalmol. 44:603-608, 1957.
122. Goerttler, K., H. Loehrke, J. Schweizer, and B. Hesse. Two-stage tumorigenesis of dermal melanocytes in the back skin of the Syrian golden hamster using systemic initiation with 7,12-dimethylbenz(a)anthracene and topical promotion with 12-o-tetradecanoylphorbol-13-acetate. Cancer Res. 40:155-161, 1980.
123. Goodman, L. S., A. G. Gilman, T. W. Rall, and T. Murad. Goodman & Gilman's The Pharmacological Basis of Therapeutics, 7th edn. New York: MacMillan Publishing Co., 1985.
124. Greiner, A., and K. Berry. Skin pigmentation and corneal and lens opacities with prolonged chlorpromazine therapy. Can. Med. Assoc. J. 90:663-665, 1964.
125. Gupta, A. K., R. S. Stern, N. A. Swanson, and T. F. Anderson. Cutaneous melanomas in patients treated with psoralens plus ultraviolet A. A case report and the experience of the PUVA Follow-Up Study. J. Am. Acad. Dermatol. 19:67-76, 1988.
126. Gupta, S. K., R. C. Murthy, and S. V. Chandra. Neuromelanin in manganese-exposed primates. Toxicol. Lett. 6:17-20, 1980.
127. Hallman, H., L. Olson, and G. Jonsson. Neurotoxicity of the meperidine analogue N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine on brain catecholamine neurons in the mouse. Eur. J. Pharmacol. 97:133-136, 1984.
128. Halprin, K. M., and A. Ohkawara. Glutathione and human pigmentation. Arch. Dermatol. 94:355-357, 1966.
129. Hart, C. W., and R. F. Naunton. The ototoxicity of chloroquine phosphate. Arch. Otolaryngol. (Chicago) 80:407-412, 1964.
130. Hartvig, P., N. G. Lindquist, S. M. Aquilonius, R. d'Argy, K. Bergström, U. Bondesson, S. À. Eckernäs, P. Gullberg, B. S. Larsson, B. Lindberg, H. Lundqvist, B. Lydén, B. Långström, P. Malmborg, K. Någren, and C.-G. Stålnacke. Distribution of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in experimental animals studied by positron emission tomography and whole body autoradiography. Life Sci. 38:89-97, 1986.
131. Hashiguchi, H., and H. Takahashi. Inhibition of two copper-containing enzymes, tyrosinase and DOPAmine beta-hydroxylase, by l-mimosine. Mol. Pharmacol. 13:362-367, 1977.
132. Hearing, V. J., and M. Jiménez. Mammalian tyrosinase-the critical regulatory control point in melanocyte pigmentation. Int. J. Biochem. 19:1141-1147, 1987.
133. Hearing, V. J., and M. Jiménez. Analysis of mammalian pigmentation at the molecular level. Pigment Cell Res. 2:75-85, 1989.
134. Hearing, V. J., T. M. Ekel, and P. M. Montague. Mammalian tyrosinase: isozymic forms of the enzyme. Int. J. Biochem. 13:99-103, 1981.
135. Heikkila, R. E., A. Hess, and R. C. Duvoisin. Dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine in mice. Science 224:1451-1453, 1984.
136. Heldaas, S. S., A. A. Andersen, and S. Langford. Incidence of cancer among vinyl chloride and polyvinyl chloride workers: further evidence for an association with malignant melanoma. Br. J. Ind. Med. 44:278-280, 1987.
137. Hochstein, P., and G. Cohen. The cytotoxicity of melanin precursors. Ann. N. Y Acad. Sci. 100:876-881, 1963.
138. Homewood, C. A., D. C. Warhurst, W. Peters, and V. C. Baggaley. Lysosomes, pH and the antimalarial action of chloroquine. Nature 235:50-52, 1972.
139. Honig, B., W. L. Morison, and D. Karp. Photochemotherapy beyond psoriasis. J. Am. Acad. Dermatol. 31(5 Pt 1):775-790, 1994.
140. Honigsmann, H., K. Wolff, T. B. Fitzpatrick, and M. A. Pathak. Oral photochemotherapy with psoralens and UVA (PUVA): principles and practice. In: Dermatology in General Medicine, T. B. Fitzpatrick, A. Z. Eisen, and K. Wolff (eds). New York: McGraw-Hill, 1987, pp. 1533-1588.
141. Hu, D. N., H. E. Savage, and J. E. Roberts. Uveal melanocytes, ocular pigment epithelium and Muller cells in culture: in vitro toxicology. Int. J. Toxicol. 21: 465-472, 2002.
142. Hutton, I. M., and M. Pentland. Uptake of melanin precursors in mouse melanoma. Clin. Oncol. 2:17-23, 1976.
143. Imokawa, G. Analysis of carbohydrate properties essential for melanogenesis in tyrosinases of cultured malignant melanoma cells by differential carbohydrate processing inhibition. J. Invest. Dermatol. 95:39-49, 1990.
144. Imokawa, G. Analysis of initial melanogenesis including tyrosinase transfer and melanosome differentiation through interrupted melanization by glutathione. J. Invest. Dermatol. 93:100-107, 1989.
145. Imokawa, G., and Y. Mishima. Functional analysis of tyrosinase isozymes of cultured malignant melanoma cells during the recovery period following interrupted melanogenesis induced by glycosylation inhibitors. J. Invest. Dermatol. 83:196-201, 1984.
146. Imokawa, G., and Y. Mishima. Analysis of tyrosinases as asparagine-linked oligosaccharides by concanavalin A lectin chromatography: appearance of a new segment of tyrosinases in melanoma cells following interrupted melanogenesis induced by glycosylation inhibitors. J. Invest. Dermatol. 85:165-168, 1985.
147. Imokawa, G., and Y. Mishima. Importance of glycoproteins in the initiation of melanogenesis: an electron microscopic study of B16 melanoma cells after release from inhibition of glycosylation. J. Invest. Dermatol. 87:319-325, 1986.
148. Inoue, S., S. Ito, K. Wakamatsu, K. Jimbow, and K. Fujita. Mechanism of growth inhibition of melanoma cells by 4-S-cysteaminylphenol and its analogues. Biochem. Pharmacol. 39:1077-1083, 1990.
149. Ishiyama, I., T. Nagai, and S. Toshida. Detection of basic drugs (methamphetamine, antidepressants and nicotine) from human hair. J. Forens. Sci. 28:380-385, 1983.
150. Israel, J., J. Connelly, S. McTigue, R. Brummett, and J. Brown. Lido-caine in the treatment of tinnitus aurium. Arch. Otolaryngol. 108:471-473, 1982.
151. Ito, S. Reexamination of the structure of eumelanin. Biochim. Biophys. Acta 883:155-161, 1986.
152. Jara, J. R., P. Aroca, F. Solano, J. H. Martínez-Liarte, and J. A. Lozano. The role of sulfhydryl compounds in mammalian melano-genesis: the effect of cysteine and glutathione upon tyrosinase and the intermediates of the pathway. Biochim. Biophys. Acta 967:296-303, 1988.
153. Jara, J. R., F. Solano, J. C. Garcia-Borron, P. Aroca, and J. A. Lozano. Regulation of distal mammalian melanogenesis. II. The role of metal cations. Biochim. Biophys. Acta 1035:276-285, 1990.
154. Jara, J. R., J. H. Martinez-Liarte, and F. Solano. Inhibition by analogues of L-tyrosine transport by B16/F10 melanoma cells. Melanoma Res. 1:15-21, 1991.
155. Jarrett, A., and G. Szabo. Pathological varieties of vitiligo and response to treatment with meladinine. Br. J. Dermatol. 68:313-326, 1956.
156. Jasim, S., and H. Tjälve. Effect of sodium pyridinethione on the uptake and distribution of nickel, cadmium and zinc in pregnant and non-pregnant mice. Toxicology 38:327-350, 1986.
157. Jelinek, J. E. Sudden whitening of the hair. Bull. N. Y. Acad. Med. 48:1003-1013, 1972.
158. Jervis, G. A. Phenylpyruvic oligophrenia: introductory study of 50 cases of mental deficiency associated with excretion of phenylpyru-vic acid. Archs. Neurol. Psychiatr. 38:944-951, 1937.
159. Jimbow, K., T. Miura, S. Ito, and K. Ishikawa. Phenolic melanin precursors provide a rational approach to the design of antitumor agents for melanoma. Pigment Cell Res. 2:34-39, 1989.
160. Johannessen, J. N., C. C. Chiueh, R. S. Burns, and S. P. Markey. Differences in the metabolism of MPTP in the rodent and primate parallel differences in sensitivity to its neurotoxic effects. Life Sci. 36:219-224, 1985.
161. Johnsson, L.-G., and J. E. Hawkins, Jr. Symposium on basic ear research II: Strial atrophy in clinical and experimental deafness. Laryngoscope 82:1105-1125, 1972.
162. Jordan, A. M., T. H. Khan, H. M. I. Osborn, A. Photiou, and P. A. Riley. Melanocyte-directed enzyme pro-drug therapy (MDEPT): development of a targeted treatment for malignant melanoma. Bioorg. Med. Chem. 7:1775-1780, 1999.
163. Jordan, A. M., T. H. Khan, H. Malkin, H. M. I. Osborn, A. Photiou, and P. A Riley. Melanocyte-directed enzyme pro-drug therapy (MDEPT): development of second-generation prodrugs for targeted treatment of malignant melanoma. Bioorg. Med. Chem. 9: 1549-1558, 2001.
164. Kable, E. P. W., and P. G. Parsons. Potency, selectivity, and cell cycle dependence of catechols in human tumour cells in vitro. Biochem. Pharmacol. 9:1711-1715, 1988.
165. Kahn, V., and A. Andrawis. Inhibition of mushroom tyrosinase by tropolone. Phytochemistry 24:905-908, 1985.
166. Kameyama, K., M. Jimenez, J. Muller, Y. Ishida, and V. J. Hearing. Regulation of mammalian melanogenesis by tyrosinase inhibition. Differentiation 42:28-36, 1989.
167. Kameyama, K., C. Sakai, S. Kuge, S. Nishiyama, Y. Tomita, S. Ito, K. Wakamatsu, and V. J. Hearing. The expression of tyrosinase, tyrosinase-related proteins 1 and 2 (TRP1 and TRP2), the silver protein, and a melanogenic inhibitor in human melanoma cells of differing melanogenic activities. Pigment Cell Res. 8:97-104, 1995.
168. Kapyaho, K., and J. Janne. Stimulation of melanotic expression in murine melanoma cells exposed to polyamine antimetabolites. Biochem. Biophys. Res. Commun. 113:18-23, 1983.
169. Kapyaho, K., R. Sinervirta, and J. Janne. Effects of inhibitors of polyamine biosynthesis on the growth and melanogenesis of murine melanoma cells. Cancer Res. 45:1444-1448, 1985.
170. Karg, E., E. Rosengren, and H. Rorsman. Hydrogen peroxide as a mediator of DOPAC-induced effects on melanoma cells. J. Invest. Dermatol. 96:224-227, 1991.
171. Keilin, D., and T. Mann. Polyphenol oxydase. Purification, nature and properties. Proc. R. Soc. London, Ser. B. Biol. Sci. 125:187-204, 1938.
172. Kemali, M., and G. Gioffré. Anatomical localization of neuromelanin in the brains of the frog and tadpole. Ultrastructural comparison of neuromelanin with other melanins. J. Anat. 142:73-83, 1985.
173. Kiguchi, K., F. R. Collart, C. Henning-Chubb, and E. Huberman. Induction of cell differentiation in melanoma cells by inhibitors of IMP dehydrogenase: altered patterns of IMP dehydrogenase expression and activity. Cell Growth Differ. 1:259-270, 1990.
174. Kinross-Wright, V. Clinical trial of a new phenothiazine compound: NP-207. Psychiatr. Res. Rep. 4:89-94, 1956.
175. Koh, H. K., B. E. Kliger, and R. A. Lew. Sunlight and cutaneous malignant melanoma: evidence for and against causation. Photochem. Photobiol. 51:765-779, 1990.
176. Komiyama, K., S. Takamatsu, Y. Takahashi, M. Shinose, M. Hayashi, H. Tanaka, Y. Iwai, S. Omura, and G. Imokawa. New inhibitors of melanogenesis, OH-3984 K1 and K2. I. Taxonomy, fermentation, isolation and biological characteristics. J. Antibiot. 46:1520-1525, 1993.
177. Korytowski, W., and T. Sarna. Bleaching of melanin pigments. Role of copper ions and hydrogen peroxide in autooxidation and photooxidation of synthetic DOPA-melanin. J. Biol. Chem. 265: 12410-12416, 1990.
178. +). Biochem. Biophys. Res. Commun. 144:692-698, 1987.
179. Korytowski, W., C. C. Felix, and B. Kalyanaraman. Oxygen activation during the interaction between MPTP metabolites and synthetic neuromelanin. An ESR-spin trapping, optical, and oxidase electrode study. Biochem. Biophys. Res. Commun. 154:781-788, 1988.
180. Korytowski, W., T. Sarna, and M. Zareba. Antioxidant action of neuromelanin: the mechanism of inhibitory effect on lipid peroxidation. Arch. Biochem. Biophys. 319:142-148, 1995.
181. Krüger, R. C. The inhibition of tyrosinase. Arch. Biochem. Biophys. 57:52-60, 1955.
182. Kubowitz, F. Spaltung und Resynthese der Polyphenoxydase und des Hämocyanins. Biochem. Z. 299:32-57, 1938.
183. Kull, F. C., R. Bonorden, and R. L. Mayer. Inhibition of melanin formation in vivo by 4-chlororesorcinol. Proc. Soc. Exp. Biol. Med. 87:538-540, 1954.
184. Kwon, B. S., M. Wakulchik, A. K. Haq, R. Halaban, and D. Kestler. Sequence analysis of mouse tyrosinase cDNA and the effect of melanotropin on its gene expression. Biochem. Biophys. Res. Commun. 153:1301-1309, 1988.
185. Labarre P., J. Papon, M. F. Moreau, N. Moins, A. Veyre, and J. C. Mandelmont. Evaluation in mice of some iodinated melanoma imaging agents using cryosectioning and multiwire proportional counting. Eur. J. Nucl. Med. 26: 494-498, 1999.
186. Land, E. J., and P. A. Riley. Spontaneous redox reactions of dopaquinone and the balance between the eumelanic and phaeo-melanic pathways. Pigment Cell Res. 13: 272-277, 2000.
187. Land, E. J, C. J. Cooksey, and P. A. Riley. Reaction kinetics of 4-methoxyorthobenzoquinone in relation to its mechanism of cytotoxicity: a pulse radiolysis study. Biochem. Pharmacol. 39:1133-1135, 1990.
188. Land, E. J., C. A. Ramsden, and P. A. Riley. Tyrosinase autoactivation and the chemistry of ortho-quinone amines. Acc. Chem. Res. 36: 300-308, 2003 a.
189. Land, E. J., C. A. Ramsden, P. A. Riley, and G. Yoganathan. Mechanistic studies of catechol generation from secondary quinone amines relevant to indole formation and tyrosinase activation. Pigment Cell Res. 16: 397-406, 2003 b.
190. Land, E. J., S. Ito, K. Wakamatsu, and P. A. Riley. Rate constants for the first two chemical steps of eumelanogenesis. Pigment Cell Res. 16: 487-493, 2003 c.
191. Land E. J., C. A. Ramsden, and P. A. Riley. Quinone chemistry and melanogenesis. In: Methods in Enzymology, vol. 378, H. Sies, and L. Packer (eds). San Diego: Elsevier Science, 2004, pp. 88-109.
192. Lang, R. Mammalian spot test with moxnidazole, a 5-nitroimidazole. Experientia 34:500-501, 1978.
193. Langston, J. W., P. Ballard, J. W. Tetrud, and I. Irwin. Chronic parkinsonism in humans due to a product of mepiridine-analog synthesis. Science 219:979-980, 1983.
194. +): identification of a metabolite of MPTP, a toxin selective to the substantia nigra. Neurosci. Lett. 48:87-92, 1984.
195. Larsson, B. Mechanisms of accumulation of foreign substances in melanin: Binding to preformed melanin and incorporation into growing melanin. Acta Univ. Upsaliensis 43:1-52, 1979.
196. Larsson, B. S. Melanin-affinic thioureas as selective melanoma seekers. Melanoma Res. 1:85-90, 1991.
197. Larsson, B. Accumulation of drugs on the melanin in the inner ear. In: Melanin: Ĩts Role in Human Photoprotection, L. Zeise, M. R. Chedekel, and T. B. Fitzpatrick (eds). Overland Park, KS: Valden-mar Publishing Co., 1995, pp. 215-219.
198. Larsson, B. S., and U. Mårs. Selective binding of 8-methoxypsoralen to melanin in vivo and in vitro. Pigment Cell Res. 6:321-322, 1993.
199. Larsson, B. S., and U. Mårs. Reduction of the oxidative capacity of melanins due to interaction with chemicals. Melanoma Res. 4 (Suppl. 2):14, 1994.
200. Larsson, B., and H. Tjälve. Studies on the melanin affinity of metal ions. Acta Physiol. Scand. 104:479-484, 1978.
201. Larsson, B., and H. Tjälve. Studies on the mechanism of drug-binding to melanin. Biochem. Pharmacol. 28:1181-1187, 1979.
202. Larsson, B., A. Oskarsson, and H. Tjälve. Binding of paraquat and diquat on melanin. Exp. Eye Res. 25:353-359, 1977.
203. Larsson, B., M. Nilsson, and H. Tjälve. The tissue-disposition of gen-tamicin in rats. Acta Pharmacol. Toxicol. 48:269-278, 1981.
204. 125I-labelled thiouracil and propylthiouracil in murine melanotic melanomas. Br. J. Cancer 46:538-550, 1982.
205. Larsson, B., L. Lyttkens, and S.-A. Wästerström. Tocainide and tinnitus: clinical effect and site of action. ORL 46:24-33, 1984.
206. Larsson, B. S., L. Dencker, K. Olander, and A. Roberto. Accumulation of radiolabelled thioamides in malignant melanomas. In: Pigment Cell, J. Bagnara, S. N. Klaus, E. Paul, and M. Schartl (eds). Tokyo: University of Tokyo Press, 1985, pp. 611-615.
207. Larsson, P., B. S. Larsson, and H. Tjälve. Binding of aflatoxin B1 to melanin. Food Chem. Toxicol. 26:579-586, 1988 a.
208. Larsson, B. S., U. Bondesson, and A. Roberto. Biological monitoring of industrial chemicals with melanin affinity. Pigment Cell Res. 1:281, 1988 b.
209. Larsson, B. S., H. Tjälve, P. Larsson, A. Roberto, I. Brandt, and K. Bergman. Retention of carcinogens in pigmented tissues due to melanin affinity (Abstract, 2nd Meeting of the ESPCR, Uppsala, Sweden, 1989). ESPCR Pigment Cell Bull. Special Issue 43, 1989 a.
210. Larsson, B. S., B. Larsson, and A. Roberto. Boron neutron capture therapy for malignant melanoma: an experimental approach. Pigment Cell Res. 2:356-360, 1989 b.
211. Larsson, B. S., H. Tjälve, A. Roberto, and U. Mårs. Chemical carcinogenesis and malignant melanoma. Pharmacol. Toxicol. 73 (Suppl. II):39, 1993.
212. Laskin, J. D., and L. A. Piccinini. Tyrosinase isozyme heterogeneity in differentiating B16/C3 melanoma. J. Biol. Chem. 261: 16226-16235, 1986.
213. Lauharanta, J., K. Kapyaho, and L. Kanerva. Changes in threedimensional structure of cultured S91 mouse melanoma cells associated with growth inhibition and induction of melanogenesis by retinoids. Arch. Dermatol. Res. 277:147-150, 1985.
214. Lea, A. J. Effect of hydroquinone monobenzyl ether on melanin formation in vitro. Nature 167:906, 1951.
215. Leblanc, B., S. Jezequel, T. Davies, G. Hanton, and C. Tarada. Binding of drugs to eye melanin is not predictive of ocular toxicity. Regul. Toxicol. Pharmacol., 28:124-132, 1998.
216. Lerch, K. Copper monooxygenases: tyrosinase and dopamine beta-hydroxylase. In: Metal Ions in Biological Systems, vol. 13, H. Sigel (ed.). New York: Marcel Dekker, 1981, pp. 143-186.
217. Lerch, K. Protein and active-site structure of tyrosinase. In: Advances in Pigment Cell Research, J. T. Bagnara (ed.). New York: Alan R. Liss, 1988, pp. 85-98.
218. Lerner, A. B., T. B. Fitzpatrick, E. Calkins, and W. H. Summerson. Mammalian tyrosinase: the relationship of copper to enzymatic activity. J. Biol. Chem. 187:793-802, 1950.
219. Levin, N., L. Queen, and A. Chalom. Detection of melanomas. Arch. Dermatol. 119:295-299, 1983.
220. Lindquist, N. G. Accumulation of drugs on melanin. Acta Radiol. Diagn. 325:1-92, 1973.
221. Lindquist, N. G., and S. Ullberg. The melanin affinity of chloroquine and chlorpromazine studied by whole body autoradiography. Acta Pharmacol. Toxicol. 31(Suppl. 2): 1-32, 1972.
222. Lindquist, N. G., A. Lydén-Sokolowski, and B. S. Larsson. Accumulation of a parkinsonism-inducing neurotoxin in melanin-bearing neurons: autoradiographic studies on 3H-MPTP. Acta Pharmacol. Toxicol. 59:161-164, 1986.
223. Lindquist, N. G., B. S. Larsson, and A. Lydén-Sokolowski. Neuromelanin and its possible protective and destructive properties. Pigment Cell Res. 1:133-136, 1987.
224. 14C]diquat in frogs and mice: accumulation in neuromelanin. Neurosci. Lett. 93:1-6, 1988.
225. Link, E. M. Biochemical targeting in melanoma. Lancet 340:949-950, 1992.
226. 211At-methylene blue in preparation for clinical trials. Melanoma Res. 4:32, 1994.
227. 211At-methylene blue for targeted radiotherapy of human melanoma xenografts: treatment of micrometastases. Cancer Res. 50:2963-2967, 1990.
228. 211At-methylene blue for targeted radiotherapy of human melanoma xenografts: treatment of cutaneous tumors and lymph node metastases. Cancer Res. 52:4385-4390, 1992.
229. 211At-methylene blue for pigmented melanoma in an animal model system. Cancer Res. 49:4332-4337, 1989.
230. 106Rh application: 16 years' experience. Arch. Ophthalmol. 101:713-717, 1983.
231. Loomis, W. F. Skin-pigment regulation of vitamin D biosynthesis in man. Science 157:501-503, 1967.
232. Lorincz, A. L. Studies on the inhibition of melanin formation. J. Invest. Dermatol. 15:425-431, 1950.
233. Lydén, A., B. S. Larsson, and N. G. Lindquist. Melanin affinity of manganese. Acta Pharmacol. Toxicol. 55:133-138, 1984.
234. Lydén, A., U. Bondesson, B. S. Larsson, and N. G. Lindquist. Melanin affinity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine, an inducer of chronic parkinsonism in humans. Acta Pharmacol. Toxicol. 53:429-432, 1983.
235. Lydén-Sokolowski, A. Melanin binding of MPTP and related substances and manganese. Possible connection with parkinsonism. Acta Univ. Upsaliensis 63:1-52, 1990.
236. Lydén-Sokolowski, A., B. S. Larsson, and N. G. Lindquist. Disposition of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in mice before and after monoamine oxidase and catecholamine reuptake inhibition. Pharmacol. Toxicol. 63:75-80, 1988.
237. Lydén-Sokolowski, A., B. S. Larsson, and N. G. Lindquist. Distribution of 1-(3H)methyl-4-phenyl-1,2,3,6-tetrahydropyridine (3H-MPTP) in the frog: uptake in neuromelanin. Pharmacol. Toxicol. 65:252-258, 1989.
238. Lyon, M. F. Attempts to test the inactive-X theory of dosage compensation in mammals. Genet. Res. 4:93-102, 1963.
239. Lyttkens, L., B. Larsson, and S.-A. Wästerström. Local anaesthetics and tinnitus: proposed peripheral mechanism of action of lidocaine. ORL 46:17-23, 1984.
240. Lyttkens, L., B. Larsson, J. Stahle, and S. Englesson. Accumulation of substances with melanin affinity to the internal ear. Adv. Otorhinolaryngol. 25:17-25, 1979.
241. MacKie, R. M., and T. Aitchison. Severe sunburn and subsequent risk of primary cutaneous malignant melanoma in Scotland. Br. J. Cancer 46:955-960, 1982.
242. Magnani, C., D. Coggon, C. Osmond, and E. D. Acheson. Occupation and five cancers: a case-control study using death certificates. Br. J. Ind. Med. 44:769-776, 1987.
243. Mann, D. M. A., and P. O. Yates. Possible role of neuromelanin in the pathogenesis of Parkinson's disease. Mech. Ageing Dev. 21:193-203, 1983.
244. Marigo, M., F. Tagliaro, C. Poiesi, S. Lafisca, and C. Neri. Determination of morphine in the hair of heroin addicts by high performance liquid chromatography with fluorimetric detection. J. Anal. Toxicol. 10:158-161, 1986.
245. Markey, S. P., N. J. Johannessen, C. C. Chiueh, R. S. Burns, and M. A. Herkenham. Intraneuronal generation of a pyridinium metabolite may cause drug-induced parkinsonism. Nature 311:464-467, 1984.
246. Mårs, U., and B. S. Larsson. New thioureas and related substances intended for melanoma targeting. Pigment Cell Res. 8:194-201, 1995.
247. Mårs, U., and B. S. Larsson. Thiourea as a melanoma targeting agent. Melanoma Res. 6:113-120, 1996.
248. Marsden, C. D. Brain melanin. In: Pigments in Pathology, M. Wollman (ed.). New York: Academic Press, 1969, pp. 395-420.
249. Martinez, J. H., F. Solano, A. Arocas, J. C. García-Borrón, J. L. Iborra, and J. A. Lozano. The existence of apotyrosinase in the cytosol of Harding-Passey mouse melanoma melanocytes and characteristics of enzyme reconstitution by Cu(II). Biochim. Biophys. Acta 923:413-420, 1987.
250. Martínez-Liarte, J. H., F. Solano, J. C. García-Borrón, J. R. Jara, and J. A. Lozano. α-MSH and other melanogenic activators mediate opposite effects on tyrosinase and dopachrome tautomerase in B16/F10 mouse melanoma cells. J. Ĩnvest. Dermatol. 99:435-439, 1992.
251. Mascagna, D., G. Ghanem, R. Morandini, M. d'Ischia, G. Misuraca, F. Lejeune, and G. Prota. Synthesis and cytotoxic properties of new N-substituted 4-aminophenol derivatives with a potential as antimelanoma agents. Melanoma Res. 2:25-32, 1992.
252. Mason, H. S. Comparative biochemistry of the phenolase complex. In: Advances in Enzymology, vol. 16, F. F. Nord (ed.). New York: Interscience, 1955, pp. 105-184.
253. Mason, H. S. Structures and functions of the phenolase complex. Nature 177:79-81, 1956.
254. Mason, H. S., W. L. Fowlks, and E. Peterson. Oxygen transfer and electron transport by the phenolase complex. J. Am. Chem. Soc. 77:2914-2915, 1955.
255. Mathias, C. G., H. I. Maibach, and M. A. Conant. Perioral leukoderma simulating vitiligo from use of a toothpaste containing cinnamic aldehyde. Arch. Dermatol. 116:1172-1173, 1980.
256. Mayer, T. C. Pigment cell migration in piebald mice. Dev. Biol. 15:521-535, 1967.
257. Meier, D. A., W. H. Beierwaltes, and R. E. Counsell. Radioactivity from labelled precursors of melanin in mice and hamsters with melanomas. Cancer Res. 27:1354-1359, 1967.
258. Meier-Ruge, W. Experimental investigations of the morphogenesis of chloroquine retinopathy. Arch. Ophthalmol. (Chicago) 73: 540-544, 1965.
259. Mena, I., O. Marin, S. Fuenzalida, and G. C. Cotzias. Chronic manganese poisoning. Clinical picture and manganese turnover. Neurology 17:128-136, 1967.
260. Menon, I. A., S. Persad, H. F. Haberman, C. J. Kurian, and P. K. Basu. A qualitative study of the melanins from blue and brown human eyes. Exp. Eye Res. 34:531-537, 1982.
261. Meyer zum Gottesberge-Orsulakova, A. Pigment und Ionentransport im Vestibularorgan. Laryngo-Rhino-Otologie 64:364-367, 1985.
262. 211At-methylene blue in targeted radiotherapy of disseminated melanoma: microscopic analysis of tumor vs. normal tissue damage. Pigment Cell Res. 6:314, 1993.
263. Mintz, B. Gene control of mammalian pigmentary differentiation: I. Clonal origin of melanocytes. Proc. Natl. Acad. Sci. USA 58:344-351, 1967.
264. 10B-chlorpromazine compound. In: Pigment Cell, vol. 1, V. Riley (ed.). Basel: S. Karger, 1973, pp. 215-221.
265. Mishima, Y., S. Hatta, Y. Ohyama, and M. Inazu. Induction of melanogenesis suppression: cellular pharmacology and mode of differential action. Pigment Cell Res. 1:367-374, 1988.
266. 10B molecule-melanoma cell interaction from in vitro to first clinical trial. Pigment Cell Res. 2:226-234, 1989.
267. Mishima, Y., M. Ichihashi, C. Honda, M. Shiono, T. Nakagawa, H. Obara, J. Shirakawa, J. Hiratsuka, K. Kanda, T. Kobayashi, T. Nozaki, O. Aizawa, T. Sato, H. Karashima, K. Yoshino, and H. Fukuda. Advances in the control of human cutaneous primary and metastatic melanoma by thermal neutron capture therapy. In: Progress in Neutron Capture Therapy for Cancer, B. J. Allen, D. E. Moore, and B. V. Harrington (eds). New York: Plenum Press, 1992, pp. 577-583.
268. 123I-N-(2-diethylaminoethyl)-2-iodobenzamide: a potential imaging agent for cutaneous melanoma staging. Eur. J. Nucl. Med. 29:1478-1484, 2002.
269. Morita, H., T. Kayashita, H. Kobata, A. Gonda, K. Takeya, and H. Itokawa. Pseudostellarins D-F, new tyrosinase inhibitory cyclic peptides from Pseudostellaria heterophylla. Tetrahedron 50:9975-9982, 1994 a.
270. Morita, H., H. Kobata, K. Takeya, and H. Itokawa. Pseudostellarin G, a new tyrosinase inhibitory cyclic octapeptide from Pseudostel-laria heterophylla. Tetrahedron Lett. 35:3563-3564, 1994 b.
271. Morrison, R., K. Mason, and S. Frost-Mason. A cladistic analysis of the evolutionary relationships of the members of the tyrosinase gene family using sequence data. Pigment Cell Res. 7:388-393, 1994.
272. Müsebeck, K. Zum Wirkungsmechanismus der Streptomycin-vergiftung des Ohres. Arch. Klin. Exp. Ohren-, Nasen-Kehlkopfheilk. 182:583-587, 1963.
273. Naish, S., and P. A. Riley. Studies on the kinetics of oxidation of 4-hydroxyanisole by tyrosinase. Biochem. Pharmacol. 38:1103-1107, 1989.
274. Naish, S., C. J. Cooksey, and P. A. Riley. Initial mushroom tyrosinase-catalysed oxidation product of 4-hydroxyanisole is 4-methoxy-ortho-benzoquinone. Pigment Cell Res. 1:379-381, 1988 a.
275. Naish, S., J. L. Holden, C. J. Cooksey, and P. A. Riley. Major primary cytotoxic product of 4-hydroxyanisole oxidation by mushroom tyrosinase is 4-methoxy ortho benzoquinone. Pigment Cell Res. 1:382-385, 1988 b.
276. Naish-Byfield, S., and P. A. Riley. Oxidation of monohydric phenol substrates by tyrosinase. An oximetric study. Biochem. J. 288:63-67, 1992.
277. Naish-Byfield, S., C. J. Cooksey, A. M. Latter, C. I. Johnson, and P. A. Riley. In vitro assessment of the structure-activity relationship of tyrosinase-dependent cytotoxicity of a series of substituted phenols. Melanoma Res. 1:273-287, 1991.
278. Naish-Byfield, S., C. J. Cooksey, and P. A. Riley. Oxidation of mono-hydric phenol substrates by tyrosinase: effect of dithiothreitol on kinetics. Biochem. J. 304:155-162, 1994.
279. Nakamura, F. Electrophysiological and cytochemical study on ototoxicity of di hydro streptomycin. Ann. Otol. Rhinol. Laryngol. 66:1080-1112, 1957.
280. Napolitano, A., M. d'Ischia, G. Prota, M. Havens, and K. Tramposch. 2-Aryl-1,3-thiazolidines as masked sulfhydryl agents for inhibition of melanogenesis. Biochim. Biophys. Acta 1073:416-422, 1991.
281. Napolitano, A., P. Di Donato, G. Prota, and E. J. Land. Transient quinonimines and 1,4-benzothiazines of phaeomelanogenesis: new pulse radiolytic and spectrophotometric evidence. Free Rad. Biol. Med. 27: 521-528, 1999.
282. Nazzaro-Porro, M., and S. Passi. Identification of tyrosinase inhibitors in cultures of Pityrosporum. J. Ĩnvest. Dermatol. 71:205-208, 1978.
283. Nelson, J. H., and C. R. Dawson. Tyrosinase. Adv. Enzymol. Relat. Areas Mol. Biol. 4:99-152, 1955.
284. Nilsson Tammela, M., and H. Tjälve. Whole-body autoradiography of (3H)dihydrostreptomycin in guinea pigs and rats. The labelling of the inner ear in relation to other tissues. Acta Otolaryngol. (Stockh.) 101:247-256, 1986.
285. Oka, M., K. Ogita, N. Saito, and Y. Mishima. Selective increase of the alpha subspecies of protein kinase C and inhibition of melano-genesis induced by retinoic acid in melanoma cells. J. Invest. Dermatol. 100:204S-208S, 1993.
286. Olander, K. Foreign melanin precursors for the detection of melanotic melanoma. Acta Univ. Upsaliensis 146:1-44, 1988.
287. Olander, K., B. S. Larsson, and L. Dencker. Thioamides as false melanin precursors: studies in murine melanomas. Acta Pharmacol. Toxicol. 52:135-142, 1983.
288. 131I)thiouracil in tumors of patients with disseminated malignant melanoma: a pilot study. Melanoma Res. 1:391-395, 1991.
289. Oliver, E. A., L. Schwartz, and L. H. Warren. Occupational leukoderma. Arch. Dermatol. 42:993-1004, 1940.
290. Orlow, S. J., A. K. Chakraborty, R. E. Boissy, and J. M. Pawelek. Inhibition of induced melanogenesis in Cloudman melanoma cells by four phenotypic modifiers. Exp. Cell Res. 191:209-218, 1990.
291. Orlow, S. J., B. K. Zhou, A. K. Chakraborty, M. Drucker, S. Pifko-Hirst, and J. M. Pawelek. High-molecular-weight forms of tyrosinase and the tyrosinase-related proteins: evidence for a melanogenic complex. J. Invest. Dermatol. 103:196-201, 1994.
292. Ortonne, J. P. Retinoic acid and pigment cells: a review of in-vitro and in-vivo studies. Br. J. Dermatol. 127:43-47, 1992.
293. Ortonne, J.-P., D. B. Mosher, and T. B. Fitzpatrick. Topics in Dermatology: Vitiligo and Other Hypomelanoses of Hair and Skin. New York: Plenum Publishing Corporation, 1983.
294. Osman, A. M., P. W. Jansen, L. A. Smets, and C. Benckhuijsen. Glucocorticoid receptors and cell cycle progression in human melanoma cell lines. J. Cell. Physiol. 125:306-312, 1985.
295. Palumbo A., M. d'Ischia, G. Misuraca, and G. Prota. Effect of metal ions on the rearrangement of dopachrome. Biochim. Biophys. Acta 925: 203-209, 1987.
296. Palumbo, A., M. d'Ischia, G. Misuraca, A. Iannone, and G. Prota. Selective uptake of 2-thiouracil into melanin-producing systems depends on chemical binding to enzymically generated dopaquinone. Biochim. Biophys. Acta 1036:221-227, 1990.
297. Palumbo, A., A. Napolitano, L. DeMartino, W. D. Vieira, and V. J. Hearing. Specific incorporation of 2-thiouracil into biological melanins. Biochim. Biophys. Acta 1200:271-276, 1994.
298. Pankovich, J. M., and K. Jimbow. Tyrosine transport in a human melanoma cell line as a basis for selective transport of cytotoxic analogues. Biochem. J. 280:721-725, 1991.
299. Pannatier, A., P. Jenner, B. Testa, and C. Etter. The skin as a drug-metabolizing organ. Drug Metab. Rev. 8:319-343, 1978.
300. Passi, S., and M. Nazzaro-Porro. Molecular basis of substrate and inhibitory specificity of tyrosinase: phenolic compounds. Br. J. Dermatol. 104:659-665, 1981.
301. Passi, S., M. Picardo, and M. Nazzaro-Porro. Comparative cytotoxicity of phenols in vitro. Biochem. J. 245:537-542, 1987.
302. 1θ2 and O2 -4) by psoralens and ultraviolet radiation (320-400nm). Biochim. Biophys. Acta 798:115-126, 1984.
303. Pathak, M. A., E. Frenk, G. Szabo, and T. B. Fitzpatrick. Cutaneous depigmentation. Clin. Res. 14:272, 1966.
304. Pavel, S., H. Elzinga, F. A. J. Muskiet, J. M. Smit, N. H. Mulder, and H. Schraffordt Koops. Eumelanin-related indolic compounds in the urine of treated melanoma patients. J. Clin. Chem. Clin. Biochem. 24:176-173, 1986.
305. Peck, S. M., and H. Sobotka. Effect of monobenzyl hydroquinone on oxidase systems in vivo and in vitro. J. Invest. Dermatol. 4:325-329, 1941.
306. Pell, S., M. T. O'Berg, and B. W. Karrh. Cancer epidemiologic surveillance in the DuPont Company. J. Occup. Med. 20:725-740, 1978.
307. Persad, S., I. A. Menon, P. K. Basu, and H. F. Haberman. Binding of imipramine, 8-methoxypsoralen and epinephrine to human blue and brown eye melanins. J. Toxicol. Cutan. Ocul. Toxicol. 5:125-132, 1986.
308. Picardo, M., S. Passi, M. Nazzaro-Porro, A. S. Breathnach, C. Zompetta, A. Faggioni, and P. Riley. Mechanism of antitumoral activity of catechols in culture. Biochem. Pharmacol. 36:417-425, 1987.
309. Potts, A. M. The concentration of phenothiazines in the eye of experimental animals. Invest. Ophthalmol. Vis. Sci. 1:522-530, 1962 a.
310. Potts, A. M. Uveal pigment and phenothiazine compounds. Trans. Am. Ophthalmol. Soc. 60:517-552, 1962 b.
311. Potts, A. M. Reaction of uveal pigment with polycyclic compounds. Invest. Ophthalmol. Vis. Sci. 3:405-416, 1964 a.
312. Potts, A. M. Further studies concerning the accumulation of polycyclic compounds on uveal melanin. Invest. Ophthalmol. Vis. Sci. 3:399-404, 1964 b.
313. Poulsen, J. Hair loss, depigmentation of hair, ichthyosis, and blepharoconjunctivitis produced by dixyrazine. Acta Derm. Venereol. 61:85-88, 1981.
314. Prota, G. Melanins and Melanogenesis. San Diego: Academic Press, 1992.
315. Prota, G. Recent advances in the chemistry of melanogenesis in mammals. J. Invest. Dermatol. 75:122-127, 1980.
316. Raghavan, P. R., P. A. Zane, and S. L. Tripp. Calculation of drug-melanin binding energy using molecular modeling. Experientia 46:77-80, 1990.
317. Rampen, F. H. J., and E. Fleuren. Melanoma of the skin is not caused by ultraviolet radiation but by a chemical xenobiotic. Med. Hypotheses 22:341-346, 1987.
318. +. Biochem. Biophys. Res. Commun. 134:743-748, 1986.
319. Rich, P. R., N. K. Wiegand, H. Blum, A. L. Moore, and W. D. Bonner. Studies on the mechanism of inhibition of redox enzymes by substituted hydroxamic acids. Biochim. Biophys. Acta 525:325-337, 1978.
320. Richardson, M. A., and T. J. Craig. The coexistence of parkinsonismlike symptoms and tardive dyskinesia. Am. J. Psychiatr. 139: 341-343, 1982.
321. Richter, C. P., and K. H. Clisby. Graying of hair produced by ingestion of phenylthiocarbamide. Proc. Soc. Exp. Biol. Med. 48: 684-687, 1941.
322. Riley, P. A. Hydroxyanisole depigmentation: in vitro studies. J. Pathol. 97:193-206, 1969 a.
323. Riley, P. A. Hydroxyanisole depigmentation: in vivo studies. J. Pathol. 97:185-191, 1969 b.
324. Riley, P. A. Mechanism of pigment cell toxicity produced by hydroxy-anisole. J. Pathol. 101:163-169, 1970.
325. Riley, P. A. Dendritic cell populations of the epidermis. In: The Physiology and Pathophysiology of the Skin, A. Jarrett (ed.). London: Academic Press, 1975, pp. 1101-1130.
326. Riley, P. A. 4-Hydroxyanisole: Recent Advances in Antimelanoma Treatment. Oxford: IRL Press, 1984.
327. Riley, P.A. Radicals and melanomas. Phil. Trans. R. Soc. London B Biol. Sci. 311:679-689, 1985.
328. Riley, P. A. Biochemical markers of differentiated function in melanocytes. In: Cutaneous Melanoma, V. Veronesi, N. Cascinelli, and M. Santanini (eds). London: Academic Press, 1987, pp. 139-144.
329. Riley, P. A. Melanogenesis: a realistic target for antimelanoma therapy? Eur. J. Cancer 27:1172-1177, 1991.
330. Riley, P. A. Materia melanica: further dark thoughts. Pigment Cell Res. 5:101-106, 1992.
331. Riley, P. A. Mechanistic aspects of the control of tyrosinase activity. Pigment Cell Res. 6:182-185, 1993.
332. Riley, P. A. Photopigmentation. In: Photobiology in Medicine, G. Jori, R. H. Pottier, M. A. J. Rodgers, and T. G. Truscott (eds). New York: Plenum Press, 1994, pp. 99-112.
333. Riley, P. A. The evolution of melanogenesis. In: Melanin: Ĩts Role in Human Photoprotection, L. Zeise, M. R. Chedekel, and T. B. Fitzpatrick (eds). Overland Park, KS: Valdenmar Publishing, 1995, pp. 1-10.
334. Riley, P. A. Melanogenesis and melanoma. Pigment Cell Res. 16: 548-552, 2003.
335. Riley, P. A., C. J. Cooksey, C. I. Johnson, E. J. Land, A. M. Latter, and C. A. Ramsden. Melanogenesis-targeted anti-melanoma prodrug development: effect of side-chain variations on the cytotoxicity of tyrosinase-generated orthoquinones in a model screening system. Eur. J. Cancer 33:135-143, 1997.
336. Roberto, A., and B. S. Larsson. The incorporation of boronated substances into melanin in vitro-an experimental model for melanotic melanoma. Strahlenther. Onkol. 165:165-167, 1989.
337. Roberto, A., B. S. Larsson, and H. Tjälve. Uptake of 7,12-dimethyl-benz(a)anthracene and benzo(a)pyrene in melanin-containing tissues. Pharmacol. Toxicol. 79:92-99, 1996.
338. Robins, A. H. Biological Aspects of Human Pigmentation. Cambridge: Cambridge University Press, 1991.
339. Rodier, J. Manganese poisoning in Moroccan miners. Br. J. Ĩnd. Med. 12:21-35, 1955.
340. Romero, C., E. Aberdam, C. Larnier, and J. P. Ortonne. Retinoic acid as modulator of UVB-induced melanocyte differentiation. Involvement of the melanogenic enzymes expression. J. Cell Sci. 107:1095-1103, 1994.
341. Roskoski, R., Jr., and S. R. Jaskunas. Chloroquine and primaquine inhibition of rat liver cell-free polynucleotide-dependent polypeptide synthesis. Biochem. Pharmacol. 21:391-399, 1972.
342. Rubin, M. The antimalarials and the tranquilizers. Dis. Nerv. Syst. 29:67-76, 1968.
343. Rüedi, L. Über die Funktion der Stria vascularis. Pract. Otorhino-laryngol. (Basel) 13:341-352, 1951.
344. Russell, L. B. The mouse spot test as a predictor of heritable genetic change and other end-points. In: Chemical Mutagens: Principles and Methods for their Detection, F. J. De Serres (ed.). New York: Plenum Press, 1983, pp. 95-110.
345. Salazar, M., K. Shimada, and P. N. Patil. Iris pigmentation and atropine mydriasis. J. Pharmacol. Exp. Ther. 197:79-88, 1976.
346. Salazar-Bookaman, M. M., I. Wainer, and P. N. Patil. Relevance of drug-melanin interactions to ocular pharmacology and toxicology. J. Ocul. Pharmacol. 10: 217-239, 1994.
347. Sarna, T. Properties and function of the ocular melanin-a photobiophysical view. J. Photochem. Photobiol. B 12:215-258, 1992.
348. Sarna, T., and H. M. Swartz. Identification and characterization of melanin in tissues and body fluids. Folia Histochem. Cytochem. 16:275-286, 1978.
349. 2+ probe of metal-ion binding sites in melanin using electron paramagnetic resonance spectroscopy. II. Natural melanin. Arch. Biochem. Biophys. 202:304-313, 1980.
350. Sarna, T., W. Korytowski, M. Pasenkiewicz-Gierula, and E. Gudowska. Ion-exchange studies in melanins. In: Proceedings of the 11th International Pigment Cell Conference, Sendai, 1980, M. Seiji (ed.). Tokyo: University of Tokyo Press, 1981, pp. 23-29.
351. Sattler, S., and H. Schutt. Johanniskraut: Ein Rezept der Natur gegen Depressionen. Therapiewoche 44:811-815, 1994.
352. Savin, C. The blood vessels and pigmentary cells of the inner ear. Ann. Otol. Rhinol. Laryngol. 74:611-622, 1965.
353. Scatchard, G., J. S. Coleman, and A. C. Shen. Physical chemistry of protein solutions. VII. The binding of some small anions to serum albumin. J. Am. Chem. Soc. 79:12-20, 1957.
354. Schallreuter, K. U., and J. M. Wood. Thioredoxin reductase in control of the pigmentary system. In: Clinics in Dermatology: Disorders of Pigmentation, R. Mackie (ed.). Philadelphia: J. B. Lippincott, 1989, pp. 92-105.
355. Schmidt, W. R., and L. W. Jarcho. Persistent dyskinesias following phenothiazine therapy. Arch. Neurol. 14:369-377, 1966.
356. Schoental, R. Irreversible depigmentation of hair by N-methyl-N-nitrosourethane. Experientia 27:552-553, 1971.
357. Schoental, R., A. Z. Joffe, and B. Yagen. Irreversible depigmentation of hair by T-2 toxin (a metabolite of Fusarium sporothichoides) and by calcium pantothenate. Experientia 34:763, 1978.
358. Schuknecht, H. F. Pathology of the Ear. Cambridge, MA: Harvard University Press, 1974.
359. Searle, C. E. Depigmentation and coat colour variegation in mice treated with 8-hydroxyquinoline. Experientia 26:944-945, 1970.
360. Searle, C. E. The selective depigmenting action of 8-hydroxyquinoline on hair growth in the mouse. Br. J. Dermatol. 86:472-480, 1972.
361. Searle, C. E., and P. A. Riley. Chemically-induced depigmentation of skin and hair. In: Haar und Haarkrankheiten, C. E. Orfanos (ed.). Stuttgart: Springer-Verlag, 1979, pp. 911-929 [English translation (1991): Hair and Hair Diseases C. E. Orfanos (ed.)].
362. Selye, H. Ischemic depigmentation. Experientia 23:524, 1967.
363. Shaw, H. M., C. M. Balch, S. J. Soong, G. W. Milton, and W. H. McCarthy. Prognostic histopathological factors in malignant melanoma. Pathology 17:271-274, 1985.
364. Shelley, W. B., and S. Ohman. Epinephrine induction of white hair in ACT rats. J. Ĩnvest. Dermatol. 53:155-158, 1969.
365. Siddall, J. R. Ocular toxic changes associated with chlorpromazine and thioridazine. Can. J. Ophthalmol. 1:190-198, 1966.
366. Smit, N. P. M., S. Pavel, A. Kammeyer, and W. Westerhof. Determination of catechol-O-methyl transferase activity in relation to melanin metabolism using high-performance liquid chromatography with fluorometric detection. Anal. Biochem. 190:286-291, 1990.
367. Smit, N., C. Tilgmann, T. Karhunen, R. Slingerland, I. Ulmanen, W. Westerhof, and S. Pavel. O-methylation of L-dopa in melanin metabolism and the presence of catechol-O-methyltransferase in melanocytes. Pigment Cell Res. 7:403-408, 1994.
368. Smit, N. P. M., S. Pavel, and P. A. Riley. Mechanisms of control of the cytotoxicity of orthoquinone intermediates of melanogenesis. In: Role of Catechol Quinone Species in Cellular Toxicity, C. R. Creveling (ed.). Johnson City, TN: F. P. Graham Publishing, 2000, pp.191-245.
369. Solano, F., J. H. Martinez-Liarte, C. Jimenez-Cervantes, J. C. García-Borrón, and J. A. Lozano. DOPAchrome tautomerase is a zinc-containing enzyme. Biochem. Biophys. Res. Commun. 204: 1243-1250, 1994.
370. Solomon, E. I., and M. D. Lowery. Electronic structure contributions to function in bioorganic chemistry. Science 259:1575-1581, 1993.
371. Spillane, J. D. Brunette to blonde: depigmentation of human hair during oral treatment with mephenesin. Br. Med. J. 1:997-1000, 1963.
372. Stenson, S. M., I. M. Siegel, and R. E. Carr. Infantile cystinosis: ocular findings and pigment dilution of eye and skin. Ophthal. Paediatr. Genet. 3:169-180, 1983.
373. Stepien, K. B., and T. Wilczok. Studies of the mechanism of chloro-quine binding to synthetic dopa-melanin. Biochem. Pharmacol. 31:3359-3365, 1982.
374. Stern, R. S. Risks of cancer associated with long-term exposure to PUVA in humans: current status-1991. Blood Cells 18:91-97, 1992.
375. Stewart, T. W., D. W. Miles, and E. R. Earnshaw. Pigmentation and retinopathy due to chloroquine. Acta. Derm. Venereol. 48:47-52, 1968.
376. Strong, L. C. Genetic analysis of the induction of tumors by methyl-cholanthrene. XI. Germinal mutations and other sudden biological changes following the subcutaneous injection of methylcholan-threne. Proc. Natl. Acad. Sci. USA 31:290-293, 1945.
377. Strong, L. C. The induction of melanotic tumours and pigmented hair changes in mice by methylcholanthrene. Ann. N. Y. Acad. Sci. Spec. Publ. 4:358-368, 1948.
378. Sunkara, P. S., C. C. Chang, N. J. Prakash, and P. J. Lachmann. Effect of inhibition of polyamine biosynthesis by DL-alpha-difluo-romethylornithine on the growth and melanogenesis of B16 melanoma in vitro and in vivo. Cancer Res. 45:4067-4070, 1985.
379. Swartz, H. M., T. Sarna, and L. Zecca. Modulation by neuromelanin of the availability and reactivity of metal ions. Ann. Neurol. 32:S69-S75, 1992.
380. Swope, V. B., Z. A. Abdel-Malek, D. N. Sauder, and J. J. Nordlund. A new role for epidermal cell-derived thymocyte activating factor (ETAF)/IL-1 as an antagonist for distinct epidermal cell function. J. Immunol. 142:1943-1949, 1989.
381. Swope, V. B., Z. A. Abdel-Malek, L. Kassem, and J. J. Nordlund. Interleukins 1a and 6 and tumor necrosis factor-β are paracrine inhibitors of human melanocyte proliferation and melanogenesis. J. Invest. Dermatol. 96:180-185, 1991.
382. Tammela, M. Tissue localization of some organic and inorganic cations. Binding to melanin and cartilage. Acta Univ. Upsaliensis 111:1-42, 1985.
383. Terao, M., L. Tabe, E. Garattini, D. Sartori, M. Studer, and B. Mintz. Isolation and characterization of variant cDNAs encoding mouse tyrosinase. Biochem. Biophys. Res. Commun. 159:848-853, 1989.
384. Terao, M., K. Tomita, T. Oki, L. Tabe, M. Gianni, and E. Garattini. Inhibition of melanogenesis by BMY-28565, a novel compound depressing tyrosinase activity in B16 melanoma cells. Biochem. Pharmacol. 43:183-189, 1992.
385. Testorf, M. F., R. Kronstrand, S. P. Svensson, B. Lundstrom, and J. Ahlner. Characterization of [3H]flunitrazepam binding to melanin. Anal. Biochem. 298: 259-264, 2001.
386. Thomas, T. L., and P. Decoufle. Mortality among workers employed in the pharmaceutical industry. A preliminary investigation. J. Occup. Med. 21:619-623, 1979.
387. Thompson, A., E. J. Land, M. R. Chedekel, K. V. Subbarao, and T.G. Truscott. A pulse radiolysis study of the oxidation of the melanin precursors 3,4-dihydroxyphenylalanine (dopa) and the cysteinyl-dopas. Biochim. Biophys. Acta 843: 49-57, 1985.
388. 14C-spermidine to melanin in vivo and in vitro. Acta Physiol. Scand. 112:209-214, 1981.
389. Tjälve, H., M. Nilsson, and B. Larsson. Thallium-201: autoradiography in pigmented mice and melanin-binding in vitro. Acta Pharmacol. Toxicol. 51:147-153, 1982.
390. Tjälve, H., C. Mejàre, and K. Borg-Neczak. Uptake and transport of manganese in primary and secondary olfactory neurons in pike. Pharmacol. Toxicol. 77:23-31, 1995.
391. Tjarks, W. 1989. Borhaltige Thioharnstoffe in der Neutronenein-fangtherapie. PhD Thesis. University of Bremen, Bremen.
392. Ucar, K. The effects of histamine H2 receptor antagonists on melano-genesis and cellular proliferation in melanoma cells in culture. Biochem. Biophys. Res. Commun. 177:545-550, 1991.
393. Uematsu, T., R. Sato, O. Fujimori, and M. Nakashima. Human scalp hair as evidence of individual dosage history of haloperidol. A possible linkage of haloperidol excretion into hair with hair pigment. Arch. Dermatol. Res. 282:120-125, 1990.
394. Ullberg, S., B. Larsson, and H. Tjälve. Autoradiography. In: Biologic Applications of Radiotracers, H. J. Glenn (ed.). Boca Raton, FL: CRC Press, 1982, pp. 55-108.
395. Van Langevelde, A., C. N. M. Bakker, H. J. Broxterman, J. G. Journée-de Korver, F. M. Kaspersen, J. A. Oosterhuis, and E. K. J. Pauwels. Potential radiopharmaceuticals for the detection of ocular melanoma, Part I, 5-iodo-2-thiouracil derivatives. Eur. J. Nucl. Med. 8:45-51, 1983.
396. Van Woert, M. H. Oxidation of reduced nicotinamide adenine dinucleotide by melanin. Life Sci. 6:2605-2612, 1967.
397. Viala, A., E. Deturmeny, C. Aubert, M. Estadieu, A. Durand, J. P. Cano, and J. Delmont. Determination of chloroquine and mono-desethylchloroquine in hair. J. Forens. Sci. 28:922-928, 1983.
398. Waardenburg, P. J. A new syndrome combining developmental anomalies of the eyelids, eyebrows and nose root with pigmentary defects of the iris and head hair and with congenital deafness. Am. J. Hum. Genet. 3:195-253, 1951.
399. Walter, J. F., W. H. Kelsey, and J. Voorlees. Psoralen plus black light inhibits epidermal DNA synthesis. Arch. Dermatol. 107:861-865, 1973.
400. Wästerström, S.-A. Accumulation of drugs on inner ear melanin: therapeutic and ototoxic mechanisms. Scand. Audiol. Suppl. 23: 1-40, 1984.
401. Wästerström, S.-A., G. Bredberg, N. G. Lindquist, L. Lyttkens, and H. Rask-Andersen. Ototoxicity of kanamycin in albino and pigmented guinea pigs. I. A morphological and electrophysiological study. Otolaryngol. Clin. North Am. 7:11-18, 1986.
402. Wätjen, F., O. Buchardt, and E. Langvad. Affinity therapeutics. 1. Selective incorporation of 2-thiouracil derivatives in murine melanomas. Cytostatic activity of 2-thiouracil arotinoids, 2-thiouracil retinoids, arotinoids and retinoids. J. Med. Chem. 25:956-960, 1982.
403. Watts, K. P., R. G. Fairchild, D. N. Slatkin, D. Greenberg, S. Packer, H. L. Atkins, and S. J. Hannon. Melanin content of hamster tissues, human tissues and various melanomas. Cancer Res. 41:467-472, 1981.
404. Westerhof, W., S. Pavel, A. Kammeyer, F. D. Beusenberg, and R. Cormane. Melanin-related metabolites as markers of the skin pigmentary system. J. Invest. Dermatol. 89:78-81, 1987.
405. Wetterholm, D. H., and F. C. Winter. Histopathology of chloroquine retinal toxicity. Arch. Ophthalmol. (Chicago) 71:82-87, 1964.
406. Whittaker, J. R. Anomalous differentiation of melanin granules caused by thiouracil. Exp. Cell Res. 44:351-361, 1966.
407. Whittaker, J. R. Biosynthesis of a thiouracil phaeomelanin in embryonic pigment cells exposed to thiouracil. J. Biol. Chem. 246: 6217-6226, 1971.
408. Wick, M. M. L-Dopa methyl ester as a new antitumor agent. Nature 269:512-513, 1977.
409. Wilcox, D. E., A. G. Porras, T. Hwang, K. Lerch, M. E. Winkler, and E. I. Solomon. Substrate analogue binding to the coupled binuclear copper active site in tyrosinase. J. Am. Chem. Soc. 107:4015-4027, 1985.
410. Wilczek, A., and Y. Mishima. Inhibitory effects of melanin monomers, dihydroxyindole-2-carboxylic acid (DHICA) and dihydroxyindole (DHI) on mammalian tyrosinase, with a special reference to the role of DHICA/DHI ratio in melanogenesis. Pigment Cell Res. 8:105-112, 1995.
411. Wilde, C. E. The role of phenylalanine in the differentiation of neural crest cells. Ann. N. Y. Acad. Sci. 60:1015-1025, 1955.
412. Winkler, M. E., K. Lerch, and E. I. Solomon. Competitive inhibitor binding to the binuclear copper active site in tyrosinase. J. Am. Chem. Soc. 103:7001-7003, 1981.
413. Wittbjer, A., G. Odh, A. M. Rosengren, E. Rosengren, and H. Rorsman. Isolation of soluble tyrosinase from human melanoma cells. Acta Derm. Venereol. (Stockh.) Suppl. 70:291-294, 1990.
414. Wood, B. J. B., and L. L. Ingraham. Labelled tyrosinase from labelled substrate. Nature 205:291-292, 1965.
415. Wood, J. M., and K. U. Schallreuter. Studies on the reactions between human tyrosinase, superoxide anion, hydrogen peroxide and thiols. Biochim. Biophys. Acta 1074:378-385, 1991.
416. Wood, J. M., K. U. Schallreuter Wood, N. J. Lindsey, S. Callaghan, and M. L. G. Gardner. A specific tetrahydrobiopterin binding domain on tyrosinase controls melanogenesis. Biochem. Biophys. Res. Commun. 206:480-485, 1995.
417. Wu, E. Y., K. Chiba, A. J. Trevor, and N. Castagnoli, Jr. Interactions of the 1-methyl-4-phenyl-2,3-dihydropyridinium species with synthetic dopamine-melanin. Life Sci. 39:1695-1700, 1986.
418. Wulf, H. C., and J. Hart. Accumulation of 8-methoxypsoralen in the rat retina. Acta Ophthalmol. 56:284-290, 1978.
419. Yamada, K., B. S. Larsson, A. Roberto, L. Dencker, and S. Ullberg. Selective incorporation of thiouracil into murine metastatic melanomas. J. Invest. Dermatol. 90:873-876, 1988.
420. Yamamoto, H., S. Takeuchi, T. Kudo, C. Sato, and T. Takeuchi. Melanin production in cultured albino melanocytes transfected with mouse tyrosinase cDNA. Jpn. J. Genet. 64:121-135, 1989.
421. Zane, P. A., S. D. Brindle, D. O. Gause, A. J. O'Buck, P. R.Raghavan, and S. L. Tripp. Physicochemical factors associated with binding and retention of compounds in ocular melanin of rats: correlations using data from whole-body autoradiography and molecular modeling for multiple linear regression analyses. Pharma-ceut. Res. 7:935-941, 1990.
422. Zareba, M., A. Bober, W. Korytowski, L. Zecca, and T. Sarna. The effect of a synthetic neuromelanin on yield of free hydroxyl radicals generated in model systems. Biochim. Biophys. Acta 1271:343-348, 1995.
423. Zecca, L., and H. M. Swartz. Total and paramagnetic metals in human substantia nigra and its neuromelanin. J. Neural Transm. Park. Dis. Dement. Sect. 5:203-213, 1993.