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Volumn 87, Issue 2, 2015, Pages 218-230

Phage display - Mediated discovery of novel tyrosinase-targeting tetrapeptide inhibitors reveals the significance of N-terminal preference of cysteine residues and their functional sulfur atom

Author keywords

[No Author keywords available]

Indexed keywords

ARBUTIN; CYSTEINE; CYSTEINYLARGINYLVALYLISOLEUCINE; ENZYME INHIBITOR; FUNCTIONAL GROUP; FUNGAL ENZYME; KOJIC ACID; MONOPHENOL MONOOXYGENASE; SULFUR; TETRAPEPTIDE; TYROSINASE INHIBITOR; UNCLASSIFIED DRUG; OLIGOPEPTIDE; PEPTIDE LIBRARY; PROTEIN BINDING;

EID: 84919724824     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.114.094185     Document Type: Article
Times cited : (26)

References (62)
  • 1
    • 70349734600 scopus 로고    scopus 로고
    • Short-sequence oligopeptides with inhibitory activity against mushroom and human tyrosinase
    • Abu Ubeid A, Zhao L, Wang Y, and Hantash BM (2009) Short-sequence oligopeptides with inhibitory activity against mushroom and human tyrosinase. J Invest Dermatol 129:2242-2249.
    • (2009) J Invest Dermatol , vol.129 , pp. 2242-2249
    • Abu Ubeid, A.1    Zhao, L.2    Wang, Y.3    Hantash, B.M.4
  • 3
    • 0013855652 scopus 로고
    • Topical use of hydroquinone as a depigmenting agent
    • Arndt KA and Fitzpatrick TB (1965) Topical use of hydroquinone as a depigmenting agent. JAMA 194:965-967.
    • (1965) JAMA , vol.194 , pp. 965-967
    • Arndt, K.A.1    Fitzpatrick, T.B.2
  • 4
    • 0035533744 scopus 로고    scopus 로고
    • Partial characterization of a peptide from honey that inhibits mushroom polyphenol oxidase
    • Ates SPS and Cokmus C (2001) Partial characterization of a peptide from honey that inhibits mushroom polyphenol oxidase. J Food Biochem 25:127-137.
    • (2001) J Food Biochem , vol.25 , pp. 127-137
    • Ates, S.P.S.1    Cokmus, C.2
  • 5
    • 33750716904 scopus 로고    scopus 로고
    • Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria
    • Blaut M, Braune A, Wunderlich S, Sauer P, Schneider H, and Glatt H (2006) Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria. Food Chem Toxicol 44:1940-1947.
    • (2006) Food Chem Toxicol , vol.44 , pp. 1940-1947
    • Blaut, M.1    Braune, A.2    Wunderlich, S.3    Sauer, P.4    Schneider, H.5    Glatt, H.6
  • 7
    • 79953124263 scopus 로고    scopus 로고
    • Screening of marine algae for potential tyrosinase inhibitor: Those inhibitors reduced tyrosinase activity and melanin synthesis in Zebrafish
    • Cha SH, Ko SC, Kim D, and Jeon YJ (2011) Screening of marine algae for potential tyrosinase inhibitor: those inhibitors reduced tyrosinase activity and melanin synthesis in zebrafish. J Dermatol 38:354-363.
    • (2011) J Dermatol , vol.38 , pp. 354-363
    • Cha, S.H.1    Ko, S.C.2    Kim, D.3    Jeon, Y.J.4
  • 9
    • 67649668609 scopus 로고    scopus 로고
    • An updated review of tyrosinase inhibitors
    • Chang TS (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440-2475.
    • (2009) Int J Mol Sci , vol.10 , pp. 2440-2475
    • Chang, T.S.1
  • 13
    • 0033559796 scopus 로고    scopus 로고
    • Inhibitors of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors
    • Curto EV, Kwong C, Hermersdorfer 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.
    • (1999) Biochem Pharmacol , vol.57 , pp. 663-672
    • Curto, E.V.1    Kwong, C.2    Hermersdorfer, H.3    Glatt, H.4    Santis, C.5    Virador, V.6    Hearing, V.J.7    Dooley, T.P.8
  • 14
    • 0028915972 scopus 로고
    • Primary structure of a potent endogenous dopa-containing inhibitor of phenol oxidase from Musca domestica
    • Daquinag AC, Nakamura S, Takao T, Shimonishi Y, and Tsukamoto T (1995) Primary structure of a potent endogenous dopa-containing inhibitor of phenol oxidase from Musca domestica. Proc Natl Acad Sci USA 92:2964-2968.
    • (1995) Proc Natl Acad Sci USA , vol.92 , pp. 2964-2968
    • Daquinag, A.C.1    Nakamura, S.2    Takao, T.3    Shimonishi, Y.4    Tsukamoto, T.5
  • 15
    • 0033573844 scopus 로고    scopus 로고
    • A novel endogenous inhibitor of phenoloxidase from Musca domestica has a cystine motif commonly found in snail and spider toxins
    • Daquinag AC, Sato T, Koda H, Takao T, Fukuda M, Shimonishi Y, and Tsukamoto T (1999) A novel endogenous inhibitor of phenoloxidase from Musca domestica has a cystine motif commonly found in snail and spider toxins. Biochemistry 38:2179-2188.
    • (1999) Biochemistry , vol.38 , pp. 2179-2188
    • Daquinag, A.C.1    Sato, T.2    Koda, H.3    Takao, T.4    Fukuda, M.5    Shimonishi, Y.6    Tsukamoto, T.7
  • 16
    • 77956907512 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a novel series of bis-salicylaldehydes as mushroom tyrosinase inhibitors
    • Delogu G, Podda G, Corda M, Fadda MB, Fais A, and Era B (2010) Synthesis and biological evaluation of a novel series of bis-salicylaldehydes as mushroom tyrosinase inhibitors. Bioorg Med Chem Lett 20:6138-6140.
    • (2010) Bioorg Med Chem Lett , vol.20 , pp. 6138-6140
    • Delogu, G.1    Podda, G.2    Corda, M.3    Fadda, M.B.4    Fais, A.5    Era, B.6
  • 18
    • 0013912614 scopus 로고
    • Hydroquinone and psoralens in the therapy of hypermelanosis and vitiligo
    • Fitzpatrick TB, Arndt KA, el-Mofty AM, and Pathak MA (1966) Hydroquinone and psoralens in the therapy of hypermelanosis and vitiligo. Arch Dermatol 93:589-600.
    • (1966) Arch Dermatol , vol.93 , pp. 589-600
    • Fitzpatrick, T.B.1    Arndt, K.A.2    El-Mofty, A.M.3    Pathak, M.A.4
  • 19
    • 0032818870 scopus 로고    scopus 로고
    • Changes in thyroid function during development of thyroid hyperplasia induced by kojic acid in F344 rats
    • Fujimoto N, Onodera H, Mitsumori K, Tamura T, Maruyama S, and Ito A (1999) Changes in thyroid function during development of thyroid hyperplasia induced by kojic acid in F344 rats. Carcinogenesis 20:1567-1571.
    • (1999) Carcinogenesis , vol.20 , pp. 1567-1571
    • Fujimoto, N.1    Onodera, H.2    Mitsumori, K.3    Tamura, T.4    Maruyama, S.5    Ito, A.6
  • 21
    • 2442505878 scopus 로고    scopus 로고
    • Inhibition of polyphenol oxidases activity by various dipeptides
    • Girelli AM, Mattei E, Messina A, and Tarola AM (2004) Inhibition of polyphenol oxidases activity by various dipeptides. J Agric Food Chem 52:2741-2745.
    • (2004) J Agric Food Chem , vol.52 , pp. 2741-2745
    • Girelli, A.M.1    Mattei, E.2    Messina, A.3    Tarola, A.M.4
  • 22
    • 84887418491 scopus 로고    scopus 로고
    • Synthesis of novel compounds as new potent tyrosinase inhibitors
    • Hamidian H (2013) Synthesis of novel compounds as new potent tyrosinase inhibitors. Biomed Res Int 2013:207181.
    • (2013) Biomed Res Int , vol.2013 , pp. 207181
    • Hamidian, H.1
  • 23
    • 84875214535 scopus 로고    scopus 로고
    • Synthesis of novel azo compounds containing 5(4H)-oxazolone ring as potent tyrosinase inhibitors
    • Hamidian H, Tagizadeh R, Fozooni S, Abbasalipour V, Taheri A, and Namjou M (2013) Synthesis of novel azo compounds containing 5(4H)-oxazolone ring as potent tyrosinase inhibitors. Bioorg Med Chem 21:2088-2092.
    • (2013) Bioorg Med Chem , vol.21 , pp. 2088-2092
    • Hamidian, H.1    Tagizadeh, R.2    Fozooni, S.3    Abbasalipour, V.4    Taheri, A.5    Namjou, M.6
  • 24
    • 42049121962 scopus 로고    scopus 로고
    • The role of melanin as protector against free radicals in skin and its role as free radical indicator in hair
    • Herrling T, Jung K, and Fuchs J (2008) The role of melanin as protector against free radicals in skin and its role as free radical indicator in hair. Spectrochim Acta A Mol Biomol Spectrosc 69:1429-1435.
    • (2008) Spectrochim Acta A Mol Biomol Spectrosc , vol.69 , pp. 1429-1435
    • Herrling, T.1    Jung, K.2    Fuchs, J.3
  • 26
    • 0026094111 scopus 로고
    • N-acetyl-4-S-cysteaminylphenol as a new type of depigmenting agent for the melanoderma of patients with melasma
    • Jimbow K (1991) N-acetyl-4-S-cysteaminylphenol as a new type of depigmenting agent for the melanoderma of patients with melasma. Arch Dermatol 127:1528-1534.
    • (1991) Arch Dermatol , vol.127 , pp. 1528-1534
    • Jimbow, K.1
  • 27
    • 67649336932 scopus 로고    scopus 로고
    • Synthesis of glabridin derivatives as tyrosinase inhibitors
    • Jirawattanapong W, Saifah E, and Patarapanich C (2009) Synthesis of glabridin derivatives as tyrosinase inhibitors. Arch Pharm Res 32:647-654.
    • (2009) Arch Pharm Res , vol.32 , pp. 647-654
    • Jirawattanapong, W.1    Saifah, E.2    Patarapanich, C.3
  • 28
    • 33846933805 scopus 로고    scopus 로고
    • Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors
    • Jun N, Hong G, and Jun K (2007) Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorg Med Chem 15:2396-2402.
    • (2007) Bioorg Med Chem , vol.15 , pp. 2396-2402
    • Jun, N.1    Hong, G.2    Jun, K.3
  • 31
    • 0023613953 scopus 로고
    • Rapid and efficient site-specific mutagenesis without phenotypic selection
    • Rough Sets and Current Trends in Computing, Springer
    • Kunkel TA, Roberts JD, and Zakour RA (1987) Rapid and efficient site-specific mutagenesis without phenotypic selection. Methods Enzymol 154:367-382.
    • (1987) Methods Enzymol , vol.154 , pp. 367-382
    • Kunkel, T.A.1    Roberts, J.D.2    Zakour, R.A.3
  • 33
    • 84896381896 scopus 로고    scopus 로고
    • Isolation, characterization, and molecular modeling of a rheumatoid factor from a Hepatitis C virus infected patient with Sjogren's syndrome
    • Lee YC, Tsai KC, Leu SJ, Wang TJ, Liu CY, and Yang YY (2013) Isolation, characterization, and molecular modeling of a rheumatoid factor from a Hepatitis C virus infected patient with Sjogren's syndrome. ScientificWorldJournal 2013:516516.
    • (2013) ScientificWorldJournal , vol.2013 , pp. 516516
    • Lee, Y.C.1    Tsai, K.C.2    Leu, S.J.3    Wang, T.J.4    Liu, C.Y.5    Yang, Y.Y.6
  • 35
    • 84862829358 scopus 로고    scopus 로고
    • Dioscin: A synergistic tyrosinase inhibitor from the roots of Smilax China
    • Liang C, Lim JH, Kim SH, and Kim DS (2012) Dioscin: a synergistic tyrosinase inhibitor from the roots of Smilax china. Food Chem 134:1146-1148.
    • (2012) Food Chem , vol.134 , pp. 1146-1148
    • Liang, C.1    Lim, J.H.2    Kim, S.H.3    Kim, D.S.4
  • 36
    • 33646827679 scopus 로고    scopus 로고
    • Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis
    • Morgan Kaufmann
    • Matoba Y, Kumagai T, Yamamoto A, Yoshitsu H, and Sugiyama M (2006) Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J Biol Chem 281:8981-8990.
    • (2006) J Biol Chem , vol.281 , pp. 8981-8990
    • Matoba, Y.1    Kumagai, T.2    Yamamoto, A.3    Yoshitsu, H.4    Sugiyama, M.5
  • 37
    • 36249015521 scopus 로고    scopus 로고
    • Hydroquinone: An evaluation of the human risks from its carcinogenic and mutagenic properties
    • McGregor D (2007) Hydroquinone: an evaluation of the human risks from its carcinogenic and mutagenic properties. Crit Rev Toxicol 37:887-914.
    • (2007) Crit Rev Toxicol , vol.37 , pp. 887-914
    • McGregor, D.1
  • 38
    • 1342310634 scopus 로고    scopus 로고
    • Radiative relaxation quantum yields for synthetic eumelanin
    • Meredith P and Riesz J (2004) Radiative relaxation quantum yields for synthetic eumelanin. Photochem Photobiol 79:211-216.
    • (2004) Photochem Photobiol , vol.79 , pp. 211-216
    • Meredith, P.1    Riesz, J.2
  • 39
    • 0024223140 scopus 로고
    • Induction of melanogenesis suppression: Cellular pharmacology and mode of differential action
    • Mishima Y, Hatta S, Ohyama Y, and Inazu M (1988) Induction of melanogenesis suppression: cellular pharmacology and mode of differential action. Pigment Cell Res 1:367-374.
    • (1988) Pigment Cell Res , vol.1 , pp. 367-374
    • Mishima, Y.1    Hatta, S.2    Ohyama, Y.3    Inazu, M.4
  • 40
    • 0028029239 scopus 로고
    • Pseudostellarins D - F, new tyrosinase inhibitory cyclic peptides from Pseudostellaria heterophylla
    • Morita H, Kayashita T, Kobata H, Gonda A, Takeya K, and Itokawa H (1994) Pseudostellarins D - F, new tyrosinase inhibitory cyclic peptides from Pseudostellaria heterophylla. Tetrahedron 50:9975-9982.
    • (1994) Tetrahedron , vol.50 , pp. 9975-9982
    • Morita, H.1    Kayashita, T.2    Kobata, H.3    Gonda, A.4    Takeya, K.5    Itokawa, H.6
  • 42
    • 34247486130 scopus 로고    scopus 로고
    • Kojic acid-tripeptide amide as a new tyrosinase inhibitor
    • Noh JM, Kwak SY, Kim DH, and Lee YS (2007) Kojic acid-tripeptide amide as a new tyrosinase inhibitor. Biopolymers 88:300-307.
    • (2007) Biopolymers , vol.88 , pp. 300-307
    • Noh, J.M.1    Kwak, S.Y.2    Kim, D.H.3    Lee, Y.S.4
  • 43
    • 0034852594 scopus 로고    scopus 로고
    • Activity and inhibition of polyphenol oxidase in extracts of bran and other milling fractions from a variety of wheat cultivars
    • Okot-Kotber, Liavoga A, Yong KJ, and Bagorogoza K (2001) Activity and inhibition of polyphenol oxidase in extracts of bran and other milling fractions from a variety of wheat cultivars. Cereal Chem 78:514-520.
    • (2001) Cereal Chem , vol.78 , pp. 514-520
    • Okot-Kotber1    Liavoga, A.2    Yong, K.J.3    Bagorogoza, K.4
  • 44
    • 0000243909 scopus 로고
    • Inhibition of polyphenol oxidaseactivity and browning by honey
    • Haller AAAI Press
    • Oszmianski JLC (1990) Inhibition of polyphenol oxidaseactivity and browning by honey. J Agric Food Chem 38:1982-1985.
    • (1990) J Agric Food Chem , vol.38 , pp. 1982-1985
    • Oszmianski, J.L.C.1
  • 46
    • 1842678419 scopus 로고    scopus 로고
    • Identification of benzene metabolites in dermal fibroblasts as nonphenolic: Regulation of cell viability, apoptosis, lipid peroxidation and expression of matrix metalloproteinase 1 and elastin by benzene metabolites
    • Philips N, Burchill D, O'Donoghue D, Keller T, and Gonzalez S (2004) Identification of benzene metabolites in dermal fibroblasts as nonphenolic: regulation of cell viability, apoptosis, lipid peroxidation and expression of matrix metalloproteinase 1 and elastin by benzene metabolites. Skin Pharmacol Physiol 17:147-152.
    • (2004) Skin Pharmacol Physiol , vol.17 , pp. 147-152
    • Philips, N.1    Burchill, D.2    O'Donoghue, D.3    Keller, T.4    Gonzalez, S.5
  • 47
    • 70350660969 scopus 로고    scopus 로고
    • Tyrosinase inhibition of Potentilla bifurca
    • in Chinese
    • Piao X, Tian Y, Mi X, and Cui J (2009). Tyrosinase inhibition of Potentilla bifurca. Zhongguo Zhong Yao Za Zhi 34:1952-1954 (in Chinese).
    • (2009) Zhongguo Zhong Yao Za Zhi , vol.34 , pp. 1952-1954
    • Piao, X.1    Tian, Y.2    Mi, X.3    Cui, J.4
  • 48
    • 0024322032 scopus 로고
    • Use of a cream based on 20% azelaic acid in the treatment of melasma
    • in Italian
    • Rigoni C, Toffolo P, Serri R, and Caputo R (1989). Use of a cream based on 20% azelaic acid in the treatment of melasma. G Ital Dermatol Venereol 124:I-VI (in Italian).
    • (1989) G Ital Dermatol Venereol , vol.124 , pp. I-VI
    • Rigoni, C.1    Toffolo, P.2    Serri, R.3    Caputo, R.4
  • 49
    • 84879227872 scopus 로고    scopus 로고
    • Tyrosinase inhibitor and radical scavenger fractions and isolated compounds from aerial parts of Peucedanum knappii Bornm
    • Sarkhail P, Sarkheil P, Khalighi-Sigaroodi F, Shafiee A, and Ostad N (2013) Tyrosinase inhibitor and radical scavenger fractions and isolated compounds from aerial parts of Peucedanum knappii Bornm. Nat Prod Res 27:896-899.
    • (2013) Nat Prod Res , vol.27 , pp. 896-899
    • Sarkhail, P.1    Sarkheil, P.2    Khalighi-Sigaroodi, F.3    Shafiee, A.4    Ostad, N.5
  • 51
    • 0034997903 scopus 로고    scopus 로고
    • Synthesis of N-substituted N-nitrosohydroxylamines as inhibitors of mushroom tyrosinase
    • Shiino M, Watanabe Y, and Umezawa K (2001) Synthesis of N-substituted N-nitrosohydroxylamines as inhibitors of mushroom tyrosinase. Bioorg Med Chem 9:1233-1240.
    • (2001) Bioorg Med Chem , vol.9 , pp. 1233-1240
    • Shiino, M.1    Watanabe, Y.2    Umezawa, K.3
  • 52
    • 4644237315 scopus 로고    scopus 로고
    • Melanin pigmentation in mammalian skin and its hormonal regulation
    • Slominski A, Tobin DJ, Shibahara S, and Wortsman J (2004) Melanin pigmentation in mammalian skin and its hormonal regulation. Physiol Rev 84:1155-1228.
    • (2004) Physiol Rev , vol.84 , pp. 1155-1228
    • Slominski, A.1    Tobin, D.J.2    Shibahara, S.3    Wortsman, J.4
  • 56
    • 84869008985 scopus 로고    scopus 로고
    • A novel bioactive chalcone of Morus australis inhibits tyrosinase activity and melanin biosynthesis in B16 melanoma cells
    • Takahashi M, Takara K, Toyozato T, and Wada K (2012) A novel bioactive chalcone of Morus australis inhibits tyrosinase activity and melanin biosynthesis in B16 melanoma cells. J Oleo Sci 61:585-592.
    • (2012) J Oleo Sci , vol.61 , pp. 585-592
    • Takahashi, M.1    Takara, K.2    Toyozato, T.3    Wada, K.4
  • 57
    • 0038172505 scopus 로고    scopus 로고
    • Hepatocellular tumor induction in heterozygous p53-deficient CBA mice by a 26-week dietary administration of kojic acid
    • Takizawa T, Mitsumori K, Tamura T, Nasu M, Ueda M, Imai T, and Hirose M (2003) Hepatocellular tumor induction in heterozygous p53-deficient CBA mice by a 26-week dietary administration of kojic acid. Toxicol Sci 73:287-293.
    • (2003) Toxicol Sci , vol.73 , pp. 287-293
    • Takizawa, T.1    Mitsumori, K.2    Tamura, T.3    Nasu, M.4    Ueda, M.5    Imai, T.6    Hirose, M.7
  • 58
    • 84255186269 scopus 로고    scopus 로고
    • Solid-phase synthesis of mimosine tetrapeptides and their inhibitory activities on neuraminidase and tyrosinase
    • Upadhyay A, Chompoo J, Taira N, Fukuta M, Gima S, and Tawata S (2011) Solid-phase synthesis of mimosine tetrapeptides and their inhibitory activities on neuraminidase and tyrosinase. J Agric Food Chem 59:12858-12863.
    • (2011) J Agric Food Chem , vol.59 , pp. 12858-12863
    • Upadhyay, A.1    Chompoo, J.2    Taira, N.3    Fukuta, M.4    Gima, S.5    Tawata, S.6
  • 60
    • 73549117206 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors
    • Yi W, Cao R, Peng W, Wen H, Yan Q, Zhou B, Ma L, and Song H (2010) Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors. Eur J Med Chem 45:639-646.
    • (2010) Eur J Med Chem , vol.45 , pp. 639-646
    • Yi, W.1    Cao, R.2    Peng, W.3    Wen, H.4    Yan, Q.5    Zhou, B.6    Ma, L.7    Song, H.8
  • 61
    • 84863984322 scopus 로고    scopus 로고
    • Tyrosinase inhibition constituents from the roots of Morus australis
    • Zheng ZP, Tan HY, and Wang M (2012) Tyrosinase inhibition constituents from the roots of Morus australis. Fitoterapia 83:1008-1013.
    • (2012) Fitoterapia , vol.83 , pp. 1008-1013
    • Zheng, Z.P.1    Tan, H.Y.2    Wang, M.3
  • 62
    • 84887223351 scopus 로고    scopus 로고
    • Synthesis, characterization and biological evaluation of paeonol thiosemicarbazone analogues as mushroom tyrosinase inhibitors
    • Zhu TH, Cao SW, and Yu YY (2013) Synthesis, characterization and biological evaluation of paeonol thiosemicarbazone analogues as mushroom tyrosinase inhibitors. Int J Biol Macromol 62:589-595.
    • (2013) Int J Biol Macromol , vol.62 , pp. 589-595
    • Zhu, T.H.1    Cao, S.W.2    Yu, Y.Y.3


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