Mechanism of selective incorporation of the melanoma seeker 2-thiouracil into growing melanin

Journal of Medicinal Chemistry

Volumn 39, Issue 26, 1996, Pages 5192-5201

  Napolitano, Alessandra ^a   Palumbo, Anna ^b   D'Ischia, Marco ^a   Prota, Giuseppe ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b Zoological Station   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DOPA; INDOLE DERIVATIVE; MELANIN; MONOPHENOL MONOOXYGENASE; PYRROLE DERIVATIVE; QUINONE DERIVATIVE; THIOURACIL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; FEMALE; MELANOGENESIS; MELANOMA; MOUSE; NONHUMAN; OXIDATION; POLYMERIZATION;

ANIMALS; BIOPOLYMERS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; MAGNETIC RESONANCE SPECTROSCOPY; MELANINS; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; THIOURACIL; TYROSINE;

EID: 0030447491     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9605243     Document Type: Article

References (46)

1. (a) Prota, G.; d'Ischia, M.; Mascagna, D. Melanogenesis as a Targeting Strategy against Metastatic Melanoma: a Reassessment. Melanoma Res. 1994, 4, 351-358.
2. (b) Mishima, Y.; Meyskens, F. L. J. New Methods of Treatment of Melanoma. In Cutaneous Melanoma Biology and Management; Cascinelli, N., Santinami, M., Veronesi, U., Eds.; Masson: Milan, 1990; pp 248-256.
3. (a) Riley, P. Melanogenesis: a Realistic Target for Antimelanoma Therapy?Eur. J. Cancer 1991, 27, 1172-1177.
4. (b) Wick, M. The relevance of Pigment Biology to Melanoma. In Cutaneous Melanoma: Current Status of Knowledge and Future Perspectives; Veronesi, U., Cascinelli, N., Santinami, M., Eds.; Academic Press: London, 1987; pp 15-20.
5. (c) Jimbow, K.; Iwashina, T.; Alena, F.; Yamada, K.; Pankovich, J.; Umemura, T. Exploitation of Pigment Biosynthesis Pathway as a Selective Chemotherapeutic Approach for Malignant Melanoma. J. Invest. Dermatol. 1993, 100, 231S-238S.
6. Prota, G. Melanins and Melanogenesis; Academic Press: San Diego, CA, 1992.
7. (a) Prota, G. Regulatory Mechanism of Melanogenesis: Beyond the Tyrosinase Concept. J. Invest. Dermatol. 1993, 100, 156S-161S.
8. (b) Hearing, V. J.; King, R. A. Determination of Skin Color: Melanocytes and Melanization. In Pigmentation and Pigmentary Disorders; Levine, N., Ed.; CRC Press: Boca Raton, FL, 1993.
9. (a) Larsson, B. J. Melanin-affinic Thioureas as Selective Melanoma Seekers. Melanoma Res. 1991, 1, 85-90.
10. (b) Mars, U.; Larsson, B. S. New Thioureas and Related Substances Intended for Melanoma Targeting. Pigment Cell Res. 1995, 8, 194-201.
11. Lindquist, N. G. Accumulation of Drugs on Melanin. Acta Radiol. 1973, 325, 1-92.
12. (a) Dencker, L.; Larsson, B.; Olander, K.; Ullberg, S.; Yokota, M. False Precursors of Melanin as Selective Melanoma Seekers. Br. J. Cancer 1979, 39, 449-452.
13. (b) Dencker, L.; Larsson, B.; Olander, K.; Ullberg, S. A New Melanoma Seeker for Possible Clinical Use: Selective Accumulation of Radiolabelled Thiouracil. Br. J. Cancer 1982, 45, 95-104.
14. (c) Fairchild, R. G.; Packer, S.; Greenberg, D.; Som, P.; Brill, A. B.; Fand, I.; McNally, W. P. Thiouracil Distribution in Mice Carrying Transplantable Melanoma. Cancer Res. 1982, 42, 5126-5132.
15. Yamada, K.; Larsson, B. S.; Roberto, A.; Dencker, L.; Ullberg, S. Selective Incorporation of Thiouracil into Murine Metastatic Melanomas. J. Invest. Dermatol. 1988, 90, 873-876.
16. 125I)-5-Iodo-2-thiouracil in Cultured Hamster, Rabbit and Human Melanoma Cells. Cancer Res. 1983, 43, 1316-1320.
17. (b) Larsson, B. S.; Dencker, L.; Olander, K.; Roberto, A. Accumulation of Radiolabelled Thioamides in Malignant Melanomas. In Pigment Cell; Bagnara, J., Klaus, S. N., Paul, E., Schartl, M., Eds.; University of Tokyo Press: Tokyo, 1985; pp 611-615.
18. 125I-labelled Thiouracil and Propylthiouracil in Murine Melanotic Melanomas. Br. J. Cancer 1982, 46, 538-550.
19. (b) van Langevelde, A.; Bakker, C. N. M.; Boxterman, H. J.; Journee-de Korver, J. G.; Kaspersen, F. M.; Osterhuis, J. A.; Pauwels, E. K. J. Potential Radiopharmaceuticals for the Detection of Ocular Melanoma. Part I. 5-Iodo-2-thiouracil Derivatives. Eur. J. Nucl. Med. 1983, 8, 45-51.
20. (c) Coderre, J. A.; Packer, S.; Fairchild, R. G.; Greenberg, D.; Laster, B.; Micca, P.; Fand, I. Iodothiouracil as a Melanoma Localizing Agent. J. Nucl. Med. 1986, 27, 1157-1164.
21. 123I)-5-Iodo-2-thiouracil. Ophtalmologica 1986, 193, 248-254.
22. 131I-Thiouracil in Tumours of Patients with Disseminated Malignant Melanoma. A Pilot Study. Melanoma Res. 1991, 1, 391-395.
23. Larsson, B. S.; Larsson, B.; Roberto, A. Boron Neutron Capture Therapy for Malignant Melanoma: An Experimental Approach. Pigment Cell Res. 1989, 2, 356-360.
24. (a) Whittaker, J. R. Anomalous Differentiation of Melanin Granules Caused by Thiouracil. Exp. Cell Res. 1966, 44, 351-361.
25. (b) Whittaker, J. R. Biosynthesis of a Thiouracil Pheomelanin in Embryonic Pigment Cells Exposed to Thiouracil. J. Biol. Chem. 1971, 246, 6217-6226.
26. Olander, K.; Larsson, B.; Dencker, L. Thioamides as False Melanin Precursors: Studies in Murine Melanomas. Acta Pharmacol. Toxicol. 1983, 52, 135-142.
27. Palumbo, A.; d'Ischia, M.; Misuraca, G.; Iannone, A.; Prota, G. Selective Uptake of 2-Thiouracil into Melanin Producing Systems Depends on Chemical Binding to Enzymically Generated Dopaquinone. Biochim. Biophys. Acta 1990, 1036, 221-227.
28. Palumbo, A.; Napolitano, A.; De Martino, L.; Vieria, W.; Hearing, V. J. Specific Incorporation of 2-Thiouracil into Biological Melanins. Biochim. Biophys. Acta 1994, 1200, 271-276.
29. Napolitano, A.; Pezzella, A.; Vincensi, M. R.; Prota, G. Oxidative Degradation of Melanins to Pyrrole Acids: a Model Study. Tetrahedron 1995, 51, 5913-5920.
30. Ito, S.; Wakamatsu, K.; Ozeki, H. Spectrophotometric Assay of Eumelanin in Tissue Samples. Anal. Biochem. 1993, 215, 273-277.
31. 35
32. 6) δ (ppm) 97.50 (d, C-7), 100.50 (d, C-3), 104.82 (d, C-4), 120.63 (s, C-9), 122.87 (d, C-2), 130.64 (s, C-8), 140.71 (s, C-5), 142.82 (s, C-6).
33. Pezzella, A.; Napolitano, A.; d'Ischia, M.; Prota, G. Oxidative Polymerisation of 5,6-Dihydroxyindole-2-carboxylic Acid to Melanin: A New Insight. Tetrahedron 1996, 52, 7913-7920.
34. Prota, G. Fortschr. Chem. Org. Naturst. 1995, 64, 94-148.
35. 2 System. Tetrahedron 1990, 46, 5789-5796.
36. Hatta, S.; Mishima, Y. Melanin Monomers within Coated Vesicles and Premelanosomes in Melanin Synthesizing Cells. J. Invest. Dermatol. 1988, 75, 181-184.
37. d'Ischia, M.; Napolitano, A.; Prota, G. Sulphydryl Compounds in Melanogenesis. Part II. Reaction of Cysteine and Glutathione with Dopachrome. Tetrahedron 1987, 43, 5357-5362.
38. d'Ischia, M.; Napolitano, A.; Prota, G. Sulphydryl Compounds in Melanogenesis. Part I. Reaction of Cysteine and Glutathione with 5,6-Diydroxyindoles. Tetrahedron 1987, 43, 5351-5356.
39. Ito, S.; Prota, G. A Facile One-step Synthesis of Cysteinyldopas using Mushroom Tyrosinase. Experientia 1977, 33, 1118-1119.
40. Chavdarian, C. G.; Castagnoli, N., Jr. Synthesis, Redox Characteristics, and in Vitro Norepinephrine Uptake Inihibiting Properties of 2-(2-Mercapto-4,5-dihydroxy-phenyl)ethylamine (6-Mercaptodopamine). J. Med. Chem. 1979, 22, 1317-1322.
41. Napolitano, A.; Pezzella, A.; d'Ischia, M.; Prota, G. The First Characterisation of a Transient 5,6-Indolequinone. Tetrahedron Lett. 1996, 37, 4241-4242.
42. Tsukamoto, K.; Palumbo, A.; d'Ischia, M.; Hearing, V. J.; Prota, G. 5,6-Dihydroxyindole-2-carboxylic Acid is Incorporated in Mammalian Melanin. Biochem. J. 1992, 286, 491-495.
43. Benigni, J. D.; Minnis, R. L. The Syntheses of 5,6-Dihydroxyindole and Some of its Derivatives. J. Heterocycl. Chem. 1965, 2, 387-392.
44. Palumbo, A.; d'Ischia, M.; Misuraca, G.; Prota, G. Effect of Metal Ions on the Rearrangement of Dopachrome. Biochim. Biophys. Acta 1987, 925, 203-209.
45. Napolitano, A.; Pezzella, A.; d'Ischia, M.; Prota, G. New Pyrrole Acids by Oxidative Degradation of Eumelanins with Hydrogen Peroxide. Further Hints to the Mechanism of Pigment Breakdown. Tetrahedron 1996, 52, 8775-8780.
46. Ito, S.; Fujita, K. Microanalysis of Eumelanin and Pheomelanin in Hair and Melanomas by Chemical Degradation and Liquid Chromatography. Anal. Biochem. 1985, 144, 527-536.