Identification of quinolines that inhibit melanogenesis by altering tyrosinase family trafficking

Molecular Pharmacology

Volumn 74, Issue 6, 2008, Pages 1576-1586

  Ni Komatsu, Li ^a   Tong, ChunXiang ^a   Chen, Guangming ^b   Brindzei, Nelya ^a   Orlow, Seth J ^a  

^a NEW YORK UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b PTC THERAPEUTICS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMODIAQUINE; ARBUTIN; CHLOROQUINE; CINCHOCAINE; CINCHONIDINE; COSMETIC; LYSOSOME ASSOCIATED MEMBRANE PROTEIN 1; MEFLOQUINE; MELANIN; MEPACRINE; MONOPHENOL MONOOXYGENASE; PRIMAQUINE DIPHOSPHATE; QUINIDINE; QUININE; QUININE ETHYLCARBONATE; QUININE SALICYLATE; QUINOLINE DERIVATIVE; TYROSINASE RELATED PROTEIN 1; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLOGICAL MODEL; CONTROLLED STUDY; DEPIGMENTATION; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; HYPERPIGMENTATION; MELANOCYTE; MELANOGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN TRANSPORT; SKIN PIGMENTATION; STRUCTURE ACTIVITY RELATION;

AFRICAN AMERICANS; ANIMALS; ASIAN CONTINENTAL ANCESTRY GROUP; CELL SURVIVAL; CELLS, CULTURED; DEPRESSION, CHEMICAL; HUMANS; MELANINS; MELANOCYTES; MEMBRANE GLYCOPROTEINS; MICE; MONOPHENOL MONOOXYGENASE; OXIDOREDUCTASES; PROTEIN TRANSPORT; QUINOLINES; SKIN PIGMENTATION; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE CULTURE TECHNIQUES;

EID: 57349133846     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.108.050633     Document Type: Article

References (40)

1. Abramowitz J and Chavin W (1980) Acute effects of two melanocytolytic agents, hydroquinone and beta-mercaptoethanolamine, upon tyrosinase activity and cyclic nucleotide levels in murine melanomas. Chem Biol Interact 32:195-208.
2. Bancroft JD and Stevens A (1982) Theory and practices of histological techniques, Churchill Livingstone, New York.
3. Boissy RE, Zhao Y, and Gahl WA (1998) Altered protein localization in melanocytes from Hermansky-Pudlak syndrome: Support for the role of the HPS gene product in intracellular trafficking. Lab Invest 78:1037-1048.
4. Chen K, Manga P, and Orlow SJ (2002) Pink-eyed dilution protein controls the processing of tyrosinase. Mol Biol Cell 13:1953-1964.
5. Curto EV, Kwong C, Hermersdörfer H, Glatt H, Santis C, Virador V, Hearing VJ Jr, and Dooley TP (1999) Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem Pharmacol 57:663-672.
6. Dell'Angelica EC (2003) Melanosome biogenesis: shedding light on the origin of an obscure organelle. Trends Cell Biol 13:503-506.
7. Dupré A, Ortonne JP, Viraben R, and Arfeux F (1985) Chloroquine-induced hypopigmentation of hair and freckles. Association with congenital renal failure. Arch Dermatol 121:1164-1166.
8. Goding CR (2007) Melanocytes: the new black. Int J Biochem Cell Biol 39:275-279.
9. Goodman LS and Gilman A (1996) Drugs used in the chemotherapy of protozoal infections, in The Pharmacological Basis of Therapeutics, 9th ed., pp 978-998, McGraw-Hill Company.
10. Hall AM, Krishnamoorthy L, and Orlow SJ (2003) Accumulation of tyrosinase in the endolysosomal compartment is induced by U18666A. Pigment Cell Res 16:149-158.
11. Hall AM and Orlow SJ (2005) Degradation of tyrosinase induced by phenylthiourea occurs following Golgi maturation. Pigment Cell Res 18:122-129.
12. Hearing VJ (2005) Biogenesis of pigment granules: a sensitive way to regulate melanocyte function. J Dermatol Sci 37:3-14.
13. Jimbow K, Quevedo WC Jr, Fitzpatrick TB, and Szabo G (1976) Some aspects of melanin biology: 1950-1975. J Invest Dermatol 67:72-89.
14. Jiménez M, Tsukamoto K, and Hearing VJ (1991) Tyrosinases from two different loci are expressed by normal and by transformed melanocytes. J Biol Chem 266:1147-1156.
15. Körner A and Pawelek J (1982) Mammalian tyrosinase catalyzes three reactions in the biosynthesis of melanin. Science 217:1163-1165.
16. Mahler R, Sissons W, and Watters K (1986) Pigmentation induced by quinidine therapy. Arch Dermatol 122:1062-1064.
17. Matsuda S, Shibayama H, Hisama M, Ohtsuki M, and Iwaki M (2008) Inhibitory effects of a novel ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate on melanogenesis. Chem Pharm Bull 56:292-297.
18. Ni X, Canuel M, and Morales CR (2006) The sorting and trafficking of lysosomal proteins. Histol Histopathol 21:899-913.
19. Ni-Komatsu L and Orlow SJ (2007) Identification of novel pigmentation modulators by chemical genetic screening. J Invest Dermatol 127:1585-1592.
20. Ni-Komatsu L and Orlow SJ (2008) Chemical genetic screening identifies tricylic compounds that decrease cellular melanin content. J Invest Dermatol 128:1236-1247.
21. Orlow SJ (1995) Melanosomes are specialized members of the lysosomal lineage of organelles. J Invest Dermatol 105:3-7.
22. Parvez S, Kang M, Chung HS, Cho C, Hong MC, Shin MK, and Bae H (2006) Survey and mechanism of skin depigmenting and lightening agents. Phytother Res 20: 921-934.
23. Raposo G, Tenza D, Murphy DM, Berson JF, and Marks MS (2001) Distinct protein sorting and localization to premelanosomes, melanosomes, and lysosomes in pigmented melanocytic cells. J Cell Biol 152:809-824.
24. Raposo G and Marks MS (2002) The dark side of lysosome-related organelles: specialization of the endocytic pathway for melanosome biogenesis. Traffic 3:237-248.
25. Richmond B, Huizing M, Knapp J, Koshoffer A, Zhao Y, Gahl WA, and Boissy RE (2005) Melanocytes derived from patients with Hermansky-Pudlak syndrome types 1, 2, and 3 have distinct defects in cargo trafficking. J Invest Dermatol 124:420-427.
26. Rosenthal MH, Kreider JW, and Shiman R (1973) Quantitative assay of melanin in melanoma cells in culture and in tumors. Anal Biochem 56:91-99.
27. Schraermeyer U, Peters S, Thumann G, Kociok N, and Heimann K (1999) Melanin granules of retinal pigment epithelium are connected with the lysosomal degradation pathway. Exp Eye Res 68:237-245.
28. Shen B, Rosenberg B, and Orlow SJ (2001) Intracellular distribution and late Endosomal effects of the ocular albinism type 1 gene product: consequences of disease-causing mutations and implications for melanosome biogenesis. Traffic 2:202-211.
29. Solano F, Briganti S, Picardo M, and Ghanem G (2006) Hypopigmentation agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res 19:550-571.
30. Takeyama R, Takekoshi S, Nagata H, Osamura RY, and Kawana S (2004) Quercetin-induced melanogenesis in a reconstituted three-dimensional human epidermal model. J Mol Histol 35:157-165.
31. Theos AC, Tenza D, Martina JA, Hurbain I, Peden AA, Sviderskaya EV, Stewart A, Robinson MS, Bennett DC, Cutler DF, et al. (2005) Functions of adaptor protein (AP)-3 and AP-1 in tyrosinase sorting from endosomes to melanosomes. Mol Biol Cell 16:5356-5372.
32. Toyofuku K, Wada I, Valencia JC, Kushimoto T, Ferrans VJ, and Hearing VJ (2001) Oculocutaneous albinism types 1 and 3 are ER retention diseases: mutation of tyrosinase or Tyrp1 can affect the processing of both mutant and wild-type proteins. FASEB J 15:2149-2161.
33. Toyofuku K, Valencia JC, Kushimoto T, Costin GE, Virador VM, Vieira WD, Ferrans VJ, and Hearing VJ (2002) The etiology of oculocutaneous albinism (OCA) type II: the pink protein modulates the processing and transport of tyrosinase. Pigment Cell Res 15:217-224.
34. Tripathi RK, Hearing VJ, Urabe K, Aroca P, and Spritz RA (1992) Mutational mapping of the catalytic activities of human tyrosinase. J Biol Chem 267:23707-23712.
35. Ujvari A, Aron R, Eisenhaure T, Cheng E, Parag HA, Smicun Y, Halaban R, and Hebert DN (2001) Translation rate of human tyrosinase determines its N-linked glycosylation level. J Biol Chem 276:5924-5931.
36. Van Den Bossche K, Naeyaert JM, and Lambert J (2006) The quest for the mechanism of melanin transfer. Traffic 7:769-778.
37. Wei ML (2006) Hermansky-Pudlak syndrome: a disease of protein trafficking and organelle function. Pigment Cell Res 19:19-42.
38. Yamaguchi Y, Brenner M, and Hearing VJ (2007) The regulation of skin pigmentation. J Biol Chem 282:27557-27561.
39. Yoon TJ, Lei TC, Yamaguchi Y, Batzer J, Wolber R, and Hearing VJ (2003) Reconstituted 3-dimensional human skin of various ethnic origins as an in vitro model for studies of pigmentation. Anal Biochem 318:260-269.
40. Yoshida Y, Hachiya A, Sriwiriyanont P, Ohuchi A, Kitahara T, Takema Y, Visscher MO, and Boissy RE (2007) Functional analysis of keratinocytes in skin color using a human skin substitute model composed of cells derived from different skin pigmentation types. FASEB J 21:2829-2839.