Short-sequence oligopeptides with inhibitory activity against mushroom and human tyrosinase

Journal of Investigative Dermatology

Volumn 129, Issue 9, 2009, Pages 2242-2249

  Abu Ubeid, Anan ^a   Zhao, Longmei ^a   Wang, Ying ^a   Hantash, Basil M ^a  

^a Elixir Institute of Regenerative Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGINYLALANYLASPARTYLSERYLARGINYLALANYLASPARTYLCYSTEINE; HYDROQUINONE; LEVODOPA; LYSYLPHENYLALANYLGLUTAMYLLYSYLLYSYLPHENYLALANYLGLUTAMYLLYSINE; LYSYLPHENYLALANYLGLUTAMYLPHENYLALANYLLYSYLPHENYLALANYLGLUTAMYL PHENYLALANINE; MELANIN; MONOPHENOL MONOOXYGENASE; OLIGOPEPTIDE; PEPTIDE LIBRARY; PROLYLLEUCYLGLYCINE; THROMBIN RECEPTOR ACTIVATING PEPTIDE 6; TYROSINE; TYROSYLARGINYLSERYLARGINYLLYSYLTYROSYLSERYLSERYLTRYPTOPHYLTYROSINE; UNCLASSIFIED DRUG; VALYLLEUCYLLEUCYLLYSINE;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CELL PROLIFERATION; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HYPERPIGMENTATION; IC 50; MELANOCYTE; MELANOGENESIS; MUSHROOM; PRIORITY JOURNAL;

EID: 70349734600     PISSN: 0022202X     EISSN: 15231747     Source Type: Journal    
DOI: 10.1038/jid.2009.124     Document Type: Article

References (41)

1. Briganti S, Camera E, Picardo M (2003) Chemical and instrumental approaches to treat hyperpigmentation. Pigment Cell Res 16:101-110
2. Burk D, Lineweaver H, Horner CK (1934) The specific influence of acidity on the mechanism of nitrogen fixation by azotobacter. J Bacteriol 27:325-340
3. Cabanes J, Chazarra S, Garcia-Carmona F (1994) Kojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase. J Pharm Pharmacol 46:982-985
4. Cheng KT, Hsu FL, Chen SH, Hsieh PK, Huang HS, Lee CK et al. (2007) New constituent from Podocarpus macrophyllus var. macrophyllus shows anti-tyrosinase effect and regulates tyrosinase-related proteins and mRNA in human epidermal melanocytes. Chem Pharm Bull (Tokyo) 55:757-761
5. Curto EV, Kwong C, Hermersdörfer H, Glatt H, Santis C, Virador V et al. (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. DeCaprio AP (1999) The toxicology of hydroquinone - relevance to occupational and environmental exposure. Crit Rev Toxicol 29:283-330
7. Ennes SBP, Paschoalick RC, De Avelar Alchorne MM (2000) A double-blind, comparative, placebo-controlled study of the efficacy and tolerability of 4 hydroquinone as a depigmenting agent in melasma. J Dermatolog Treat 11:173-179
8. Finlay AY (1997) Quality of life measurement in dermatology: a practical guide. Br J Dermatol 136:305-314
9. Hearing VJ, Ekel TM (1976) Mammalian tyrosinase. A comparison of tyrosine hydroxylation and melanin formation. Biochem J 157:549-557
10. Hermanns JF, Pierard-Franchimont C, Piérard GE (2000) Skin colour assessment in safety testing of cosmetics. An overview. Int J Cosmet Sci 22:67-71
11. Ishikawa M, Kawase I, Ishii F (2007) Combination of amino acids reduces pigmentation in B16F0 melanoma cells. Biol Pharm Bull 30:677-681
12. Jimbow K, Obata H, Pathak MA, Fitzpatrick TB (1974) Mechanism of depigmentation by hydroquinone. J Invest Dermatol 62:436-449
13. Johnston GA, Sviland L, McLelland J (1998) Melasma of the arms associated with hormone replacement therapy. Br J Dermatol 139:932
14. Kadekaro AL, Kanto H, Kavanagh R, Abdel-Malek ZA (2003) Significance of the melanocortin 1 receptor in regulating human melanocyte pigmentation, proliferation, and survival. Ann N Y Acad Sci 994:359-365
15. Katayama K, Armendariz-Borunda J, Raghow R, Kang AH, Seyer JM (1993) A pentapeptide from type I procollagen promotes extracellular matrix production. J Biol Chem 268:9941-9944
16. Kojima S, Yamaguchi H, Morita K, Ueno Y (1995) Inhibitory effect of sodium 5,6-benzylidene ascorbate (SBA) on the elevation of melanin biosynthesis induced by ultraviolet-A (UV-A) light in cultured B-16 melanoma cells. Biol Pharm Bull 18:1076-1080
17. Lacz NL, Vafaie J, Kihiczak NI, Schwartz RA (2004) Postinflammatory hyperpigmentation: a common but troubling condition. Int J Dermatol 43:362-365
18. Lindquist NG (1973) Accumulation of drugs on melanin. Acta Radiol Diagn (Stockh) 325:1-92
19. Lupo MP, Cole AL (2007) Cosmeceutical peptides. Dermatol Ther 20:343-349
20. Lynde CB, Kraft JN, Lynde CW (2006) Topical treatments for melasma and postinflammatory hyperpigmentation. Skin Therapy Lett 11:1-6
21. Maeda K, Fukuda M (1996) Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 276:765-769
22. Naeyaert JM, Eller M, Gordon PR, Park HY, Gilchrest BA (1991) Pigment content of cultured human melanocytes does not correlate with tyrosinase message level. Br J Dermatol 125:297-303
23. Nagata H, Takekoshi S, Takeyama R, Homma T, Yoshiyuki Osamura R (2004) Quercetin enhances melanogenesis by increasing the activity and synthesis of tyrosinase in human melanoma cells and in normal human melanocytes. Pigment Cell Res 17:66-73
24. Olivares C, Jimenez-Cervantes C, Lozano JA, Solano F, García-Borrón JC (2001) The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase. Biochem J 354(Part 1):131-139
25. Palumbo A, d?Ischia M, Misuraca G, Prota G (1991) Mechanism of inhibition of melanogenesis by hydroquinone. Biochim Biophys Acta 1073:85-90
26. Parvez S, Kang M, Chung HS, Cho C, Hong MC, Shin MK et al. (2006) Survey and mechanism of skin depigmenting and lightening agents. Phytother Res 20:921-934
27. Passi S, Nazzaro-Porro M (1981) Molecular basis of substrate and inhibitory specificity of tyrosinase: phenolic compounds. Br J Dermatol 104:659-665
28. Pathak MA, Fitzpatrick TB, Kraus EW (1986) Usefulness of retinoic acid in the treatment of melasma. J Am Acad Dermatol 15(4 Part 2):894-899
29. Penney KB, Smith CJ, Allen JC (1984) Depigmenting action of hydroquinone depends on disruption of fundamental cell processes. J Invest Dermatol 82:308-310
30. Petit L, Pierard GE (2003) Skin-lightening products revisited. Int J Cosmet Sci 25:169-181
31. Piao LZ, Park HR, Park YK, Lee SK, Park JH, Park MK (2002) Mushroom tyrosinase inhibition activity of some chromones. Chem Pharm Bull (Tokyo) 50:309-311
32. Pomerantz SH (1966) The tyrosine hydroxylase activity of mammalian tyrosinase. J Biol Chem 241:161-168
33. Pomerantz SH, Warner MC (1967) 3,4-Dihydroxy-L-phenylalanine as the tyrosinase cofactor. Occurrence in melanoma and binding constant. J Biol Chem 242:5308-5314
34. Rendon M, Berneburg M, Arellano I, Picardo M (2006) Treatment of melasma. J Am Acad Dermatol 54(5 Suppl 2):S272-81
35. Robinson LR, Fitzgerald NC, Doughty DG, Dawes NC, Berge CA, Bissett DL (2005) Topical palmitoyl pentapeptide provides improvement in photo-aged human facial skin. Int J Cosmet Sci 27:155-160
36. Sanchez-Ferrer A, Rodriguez-Lopez JN, Garćia-Cánovas F, Garćia-Carmona F (1995) Tyrosinase: a comprehensive review of its mechanism. Biochim Biophys Acta 1247:1-11
37. Schallreuter KU, Kothari S, Chavan B, Spencer JD (2008) Regulation of melanogenesis-controversies and new concepts. Exp Dermatol 17:395-404
38. Schallreuter KU, Wood JW (1990) A possible mechanism of action for azelaic acid in the human epidermis. Arch Dermatol Res 282:168-171
39. Schurink M, van Berkel WJ, Wichers HJ, Boeriu CG (2007) Novel peptides with tyrosinase inhibitory activity. Peptides 28:485-495
40. 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
41. Sugimoto K, Nishimura T, Nomura K, Sugimoto K, Kuriki T (2003) Syntheses of arbutin-alpha-glycosides and a comparison of their inhibitory effects with those of alpha-arbutin and arbutin on human tyrosinase. Chem Pharm Bull (Tokyo) 51:798-801