The hypopigmentary action of KI-063 (a new tyrosinase inhibitor) combined with terrein

Journal of Pharmacy and Pharmacology

Volumn 60, Issue 3, 2008, Pages 343-348

  Kim, Dong Seok ^a   Lee, Sangku ^b   Lee, Hyun Kyung ^c   Park, Seo Hyoung ^c   Ryoo, In Ja ^b   Yoo, Ick Dong ^b   Kwon, Sun Bang ^d   Kwang, Jin Baek ^a   Na, Jung Im ^c   Park, Kyoung Chan ^c,e  

^a Chung Ang University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^c Seoul National University   (South Korea)

^d Welskin Co Ltd   (South Korea)

^e Seoul National University Bundang Hospital   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; KI 063; MONOPHENOL MONOOXYGENASE; TERREIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CYTOTOXICITY; DRUG MECHANISM; ENZYME SYNTHESIS; HYPOPIGMENTATION; MELANOGENESIS; MOUSE; NONHUMAN;

AGARICALES; ANIMALS; CAFFEIC ACIDS; CELL LINE; CELL SURVIVAL; CYCLOPENTANES; DOSE-RESPONSE RELATIONSHIP, DRUG; DOWN-REGULATION; DRUG SYNERGISM; ENZYME INHIBITORS; HYPOPIGMENTATION; MELANINS; MELANOCYTES; MICE; MICROPHTHALMIA-ASSOCIATED TRANSCRIPTION FACTOR; MONOPHENOL MONOOXYGENASE;

EID: 39449111353     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.60.3.0009     Document Type: Article

References (36)

1. Ando, H., Kondoh, H., Ichihashi, M., Hearing, V. J. (2007) Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase. J. Invest. Dermatol. 127: 751-761
2. Bertolotto, C., Busca, R., Abbe, P., Bille, K., Aberdam, E., Ortonne, J. P., Ballotti, R. (1998) Different cis-acting elements are involved in the regulation of TRP1 and TRP2 promoter activities by cyclic AMP: pivotal role of M boxes (GTCATGTGCT) and of microphthalmia. Mol. Cell Biol. 18: 694-702
3. Busca, R., Ballotti, R. (2000) Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res 13: 60-69
4. Busca, R., Bertolotto, C., Ortonne, J. P., Ballotti, R. (1996) Inhibition of the phosphatidylinositol 3-kinase/p70(S6)-kinase pathway induces B16 melanoma cell differentiation. J. Biol. Chem. 271: 31824-31830
5. Chang, T. S. (2007) Two potent suicide substrates of mushroom tyrosinase: 7, 8, 4′-trihydroxyisoflavone and 5, 7, 8, 4′- tetrahydroxyisoflavone. J. Agric. Food Chem. 55: 2010-2015
6. Dooley, T. P., Gadwood, R. C., Kilgore, K., Thomasco, L. M. (1994) Development of an in vitro primary screen for skin depigmentation and antimelanoma agents. Skin Pharmacol 7: 188-200
7. Englaro, W., Bertolotto, C., Busca, R., Brunet, A., Pages, G., Ortonne, J. P., Ballotti, R. (1998) Inhibition of the mitogen-activated protein kinase pathway triggers B16 melanoma cell differentiation. J. Biol. Chem. 273: 9966-9970
8. Espin, J. C., Varon, R., Tudela, J., Garcia-Canovas, F. (1997) Kinetic study of the oxidation of 4-hydroxyanisole catalyzed by tyrosinase. Biochem. Molec. Biol. Int. 41: 1265-1276
9. Fenoll, L. G., Garcia-Ruiz, P. A., Varon, R., Garcia-Canovas, F. (2003) Kinetic study of the oxidation of quercetin by mushroom tyrosinase. J. Agric. Food Chem. 51: 7781-7787
10. Garcia Canovas, F., Tudela, J., Martinez Madrid, C., Varon, R., Garcia Carmona, F., Lozano, J. A. (1987) Kinetic study on the suicide inactivation of tyrosinase induced by catechol. Biochim. Biophys. Acta 912: 417-423
11. Haghbeen, K., Saboury, A. A., Karbassi, F. (2004) Substrate share in the suicide inactivation of mushroom tyrosinase. Biochim. Biophys. Acta 1675: 139-146
12. Hearing, V. J., Jimenez, M. (1989) Analysis of mammalian pigmentation at the molecular level. Pigment Cell Res 2: 75-85
13. Hearing, V. J., Tsukamoto, K. (1991) Enzymatic control of pigmentation in mammals. FASEB J. 5: 2902-2909
14. Hemesath, T. J., Price, E. R., Takemoto, C., Badalian, T., Fisher, D. E. (1998) MAP kinase links the transcription factor Microphthalmia to c-Kit signalling in melanocytes. Nature 391: 298-301
15. Hughes, A. E., Newton, V. E., Liu, X. Z., Read, A. P. (1994) A gene for Waardenburg syndrome type 2 maps close to the human homologue of the microphthalmia gene at chromosome 3p12-p14.1. Nat. Genet. 7: 509-512
16. Khemis, A., Kaiafa, A., Queille-Roussel, C., Duteil, L., Ortonne, J. P. (2007) Evaluation of efficacy and safety of rucinol serum in patients with melasma: a randomized controlled trial. Br. J. Dermatol. 156: 997-1004
17. Kim, Y. J., Uyama, H. (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell. Mol. Life Sci. 62: 1707-1723
18. Kim, D. S., Kim, S. Y., Chung, J. H., Kim, K. H., Eun, H. C., Park, K. C. (2002) Delayed ERK activation by ceramide reduces melanin synthesis in human melanocytes. Cell Signal. 14: 779-785
19. Kim, D. S., Hwang, E. S., Lee, J. E., Kim, S. Y., Kwon, S. B., Park, K. C. (2003) Sphingosine-1-phosphate decreases melanin synthesis via sustained ERK activation and subsequent MITF degradation. J. Cell. Sci. 116: 1699-1706
20. Kim, D. S., Kim, S. Y., Park, S. H., Choi, Y. G., Kwon, S. B., Kim, M. K., Na, J. I., Youn, S. W., Park, K. C. (2005) Inhibitory effects of 4-n-butylresorcinol on tyrosinase activity and melanin synthesis. Biol. Pharm. Bull. 28: 2216-2219
21. Lee, S., Kim, W. G., Kim, E., Ryoo, I. J., Lee, H. K., Kim, J. N., Jung, S. H., Yoo, I. D. (2005) Synthesis and melanin biosynthesis inhibitory activity of (+/-)-terrein produced by Penicillium sp. 20135. Bioorg. Med. Chem. Lett. 15: 471-473
22. Lin, J. Y., Fisher, D. E. (2007) Melanocyte biology and skin pigmentation. Nature 445: 843-850
23. Park, S. H., Kim, D. S., Kim, W. G., Ryoo, I. J., Lee, D. H., Huh, C. H., Youn, S. W., Yoo, I. D., Park, K. C. (2004) Terrein: a new melanogenesis inhibitor and its mechanism. Cell. Mol. Life Sci. 61: 2878-2885
24. Shimizu, K., Kondo, R., Sakai, K. (2000) Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: structure-activity investigations. Planta Med. 66: 11-15
25. Slominski, A., Tobin, D. J., Shibahara, S., Wortsman, J. (2004) Melanin pigmentation in mammalian skin and its hormonal regulation. Physiol. Rev. 84: 1155-1228
26. Solano, F., Briganti, S., Picardo, M., Ghanem, G. (2006) Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res. 19: 550-571
27. Song, S., Lee, H., Jin, Y., Ha, Y. M., Bae, S., Chung, H. Y., Suh, H. (2007) Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase. Bioorg. Med. Chem. Lett. 17: 461-464
28. Tachibana, M. (1997) Evidence to suggest that expression of MITF induces melanocyte differentiation and haploinsufficiency of MITF causes Waardenburg syndrome type 2A. Pigment Cell Res. 10: 25-33
29. Tachibana, M. (2000) MITF: a stream flowing for pigment cells. Pigment Cell Res. 13: 230-240
30. Tasaka, K., Kamei, C., Nakano, S., Takeuchi, Y., Yamato, M. (1998) Effects of certain resorcinol derivatives on the tyrosinase activity and the growth of melanoma cells. Methods Find Exp. Clin. Pharmacol. 20: 99-109
31. Tassabehji, M., Newton, V. E., Read, A. P. (1994) Waardenburg syndrome type 2 caused by mutations in the human microphthalmia (MITF) gene. Nat. Genet. 8: 251-255
32. Tsuboi, T., Kondoh, H., Hiratsuka, J., Mishima, Y. (1998) Enhanced melanogenesis induced by tyrosinase gene-transfer increases boron-uptake and killing effect of boron neutron capture therapy for amelanotic melanoma. Pigment Cell Res. 11: 275-282
33. Tudela, J., Garcia Canovas, F., Varon, R., Jimenez, M., Garcia-Carmona, F., Lozano, J. A. (1988) Kinetic study in the transient phase of the suicide inactivation of frog epidermis tyrosinase. Biophys. Chem. 30: 303-310
34. Wu, M., Hemesath, T. J., Takemoto, C. M., Horstmann, M. A., Wells, A. G., Price, E. R., Fisher, D. Z., Fisher, D. E. (2000) c-Kit triggers dual phosphorylations, which couple activation and degradation of the essential melanocyte factor Mi. Genes Dev. 14: 301-312
35. Xu, W., Gong, L., Haddad, M. M., Bischof, O., Campisi, J., Yeh, E. T., Medrano, E. E. (2000) Regulation of microphthalmia-associated transcription factor MITF protein levels by association with the ubiquitin-conjugating enzyme hUBC9. Exp. Cell Res. 255: 135-143
36. Yasumoto, K., Yokoyama, K., Takahashi, K., Tomita, Y., Shibahara, S. (1997) Functional analysis of microphthalmia-associated transcription factor in pigment cell-specific transcription of the human tyrosinase family genes. J. Biol. Chem. 272: 503-509