Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors

Biochimie

Volumn 94, Issue 2, 2012, Pages 533-540

  Ha, Young Mi ^a   Park, Yun Jung ^a   Lee, Ji Yeon ^a   Park, Daeui ^a   Choi, Yeon Ja ^a   Lee, Eun Kyeong ^a,b   Kim, Ji Min ^a   Kim, Jin Ah ^a   Park, Ji Young ^a   Lee, Hye Jin ^a   Moon, Hyung Ryong ^a   Chung, Hae Young ^a  

^a Pusan National University   (South Korea)

^b Dongnam Institute of Radiological and Medical Science   (South Korea)

Author keywords

2 (Substituted phenyl)thiazolidine 4 carboxylic acid derivatives; Docking analysis; Hyperpigmentation; Melanin biosynthesis; Tyrosinase inhibitor

Indexed keywords

(2,4) 2 (2 HYDROXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (2,4 DIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (3 ETHOXY 4 HYDROXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (3 HYDROXY 4 METHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (3,4 DIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (4 HYDROXY 3 METHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (4 HYDROXY 3,5 DIMETHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (4 HYDROXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; (2,4) 2 (4 METHOXYPHENYL)THIAZOLIDINE 4 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; DOPA; MELANIN; PHENYLTHIOUREA; PROTEIN KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CELL ASSAY; CELL VIABILITY; CONTROLLED STUDY; DRUG BINDING; DRUG DESIGN; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DOCKING; MOUSE; NONHUMAN;

AGARICALES; ALPHA-MSH; ANIMALS; CELL SURVIVAL; ENZYME INHIBITORS; KINETICS; LEVODOPA; MELANINS; MELANOMA, EXPERIMENTAL; MICE; MODELS, MOLECULAR; MONOPHENOL MONOOXYGENASE; PHENYLTHIOUREA; PROTEIN STRUCTURE, TERTIARY; THIAZOLIDINES; TUMOR CELLS, CULTURED; TYROSINE;

BASIDIOMYCOTA;

EID: 84855853000     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2011.09.002     Document Type: Article

References (36)

1. H. Choi, S. Ahn, B.G. Lee, I. Chang, and J.S. Hwang Inhibition of skin pigmentation by an extract of Lepidium apetalum and its possible implication in IL-6 mediated signaling Pigment Cell. Res. 18 2005 439 446 (Pubitemid 41691459)
2. S. Im, J. Kim, W.Y. On, and W.H. Kang Increased expression of alpha-melanocyte-stimulating hormone in the lesional skin of melasma Br. J. Dermatol. 46 2002 165 167 (Pubitemid 34158436)
3. K. Jones, J. Hughes, M. Hong, Q. Jia, and S. Orndorff Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase Pigment Cell. Res. 15 2002 335 340
4. C.J. Cooksey, P.J. Garratt, E.J. Land, S. Pavel, C.A. Ramsden, P.A. Riley, and N.P. Smit Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase J. Biol. Chem. 272 1997 26226 26235 (Pubitemid 27458833)
5. J.T. Lim Treatment of melasma using kojic acid in a gel containing hydroquinone and glycolic acid Dermatol. Surg. 25 1999 282 284 (Pubitemid 29191314)
6. K. Maeda, and M. Fukuda Arbutin: mechanism of its depigmenting action in human melanocyte culture J. Pharmacol. Exp. Ther. 276 1996 765 769 (Pubitemid 126660519)
7. K. Ohguchi, T. Tanaka, I. Iliya, T. Ito, M. Iinuma, K. Matsumoto, Y. Akao, and Y. Nozawa Gnetol as a potent tyrosinase inhibitor from genus Gnetum Biosci. Biotechnol. Biochem. 67 2003 663 665 (Pubitemid 39251971)
8. J.S. Roh, J.Y. Han, J.H. Kim, and J.K. Hwang Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesis Biol. Pharm. Bull. 27 2004 1976 1978 (Pubitemid 41701574)
9. J.K. No, M.S. Kim, Y.J. Kim, S.J. Bae, J.S. Choi, and H.Y. Chung Inhibition of tyrosinase by protocatechuic aldehyde Am. J. Chin. Med. 32 2004 1 7
10. K. Ohguchi, T. Tanaka, T. Kido, K. Baba, M. Iinuma, K. Matsumoto, Y. Akao, and Y. Nozawa Effects of hydroxystilbene derivatives on tyrosinase activity Biochem. Biophys. Res. Commun. 307 2003 861 863 (Pubitemid 36871652)
11. H. Takiwaki, S. Shirai, H. Kohno, H. Soh, and S. Arase The degrees of UVB-induced erythema and pigmentation correlate linearly and are reduced in a parallel manner by topical anti-inflammatory agents J. Invest. Dermatol. 103 1994 642 646 (Pubitemid 24350128)
12. N.H. Shin, S.Y. Ryu, H.S. Lee, K.R. Min, and Y.S. Kim Inhibitory effects of hydroxystilbenes on cyclooxygenase from sheep seminal vesicles Planta Med. 64 1998 283 284
13. S. Nimmanpisut, P. Chudapongse, and K. Ratanabanangkoon Effects of 2,4,3′,5′-tetrahydroxystilbene on oxidative phosphorylation by rat liver mitochondria Biochem. Pharmacol. 25 1976 1245 1248
14. S.H. Song, H.J. Lee, Y.G. Jin, Y.M. Ha, S.J. Bae, H.Y. Chung, and H.S. Suh Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase Bioorg. Med. Chem. Lett. 17 2007 461 464 (Pubitemid 46073741)
15. Y.M. Kim, J. Yun, C.K. Lee, H. Lee, K.R. Min, and Y. Kim Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action J. Biol. Chem. 277 2002 16340 16344 (Pubitemid 34967923)
16. Y.M. Ha, S.W. Chung, S. Song, H. Lee, H. Suh, and H.Y. Chung 4-(6-Hydroxy-2-naphthyl)-1,3-bezendiol: a potent, new tyrosinase inhibitor Biol. Pharm. Bull. 30 2007 1711 1715 (Pubitemid 47407692)
17. S. Okombi, D. Rival, S. Bonnet, A.M. Mariotte, E. Perrier, and A. Boumendjel Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes J. Med. Chem. 49 2006 329 333 (Pubitemid 43077345)
18. A. Andrawis, and V. Kahn Effect of methimazole on the activity of mushroom tyrosinase Biochem. J. 235 1986 91 96 (Pubitemid 16041977)
19. I. Kubo, K.I. Nihei, and K. Shimizu Oxidation products of quercetin catalyzed by mushroom tyrosinase Bioorg. Med. Chem. 12 2004 5343 5347 (Pubitemid 39243954)
20. R. Matsuura, H. Ukeda, and M. Sawamura Tyrosinase inhibitory activity of citrus essential oils J. Agric. Food Chem. 54 2006 2309 2313
21. Y.J. Kim, J.K. No, J.H. Lee, and H.Y. Chung 4,4′-Dihydroxybiphenyl as a new potent tyrosinase inhibitor Biol. Pharm. Bull. 28 2005 323 327 (Pubitemid 40880017)
22. J.K. No, M.S. Kim, Y.J. Kim, S.J. Bae, J.S. Choi, and H.Y. Chung Inhibition of tyrosinase by protocatechuic aldehyde Am. J. Chin. Med. 32 2004 97 103 (Pubitemid 38967859)
23. Y. Kim, J. No, J. Lee, M. Kim, and H. Chung Antimelanogenic activity of 3,4-dihydroxyacetophenone: inhibition of tyrosinase and MITF Biosci. Biotechnol. Biochem. 70 2006 532 534 (Pubitemid 43289440)
24. Y. Matsuo, H. Kuwayama, H. Itoh, A. Seki, S. Fukuda, T. Kawasaki, T. Hotta, Y. Ohsaka, and K. Komatsu Gastric anti-ulcer and cytoprotective properties of 2-(3,4-dimethoxyphenyl)-5-methyl-thiazolidine-4-one in rat experimental ulcers Arzneimittelforschung 36 1986 1236 1240 (Pubitemid 16035240)
25. H. Tada, O. Shiho, K. Kuroshima, M. Koyama, and K. Tsukamoto An improved colorimetric assay for interleukin 2 J. Immunol. Methods 93 1986 157 165 (Pubitemid 17190370)
26. J.K. No, D.Y. Soung, Y.J. Kim, K.H. Shim, Y.S. Jun, S.H. Rhee, T. Yokozawa, and H.Y. Chung Inhibition of tyrosinase by green tea components Life Sci. 65 1999 PL241 246
27. D.S. Kim, S.Y. Kim, J.H. Chung, K.H.H. Kim, C. Eun, and K.C. Park Delayed ERK activation by ceramide reduces melanin synthesis in human melanocytes Cell Signal. 14 2002 779 785
28. M.L. Bilodeau, J.D. Greulich, R.L. Hullinger, C. Bertolotto, R. Ballotti, and O.M. Andrisani BMP-2 stimulates tyrosinase gene expression and melanogenesis in differentiated melanocytes Pigment Cell Res. 14 2001 328 336 (Pubitemid 32956358)
29. K. Arnold, L. Bordoli, J. Kopp, and T. Schwede The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling Bioinformatics 22 2006 195 201 (Pubitemid 43205406)
30. R. Rodriguez, G. Chinea, N. Lopez, T. Pons, and G. Vriend Homology modeling, model and software evaluation: three related resources Bioinformatics 14 1998 523 528 (Pubitemid 28416766)
31. D.T. Moustakas, P.T. Lang, S. Pegg, E. Pettersen, I.D. Kuntz, N. Brooijmans, and R.C. Rizzo Development and validation of a modular, extensible docking program: DOCK 5 J. Comput. Aided Mol. Des. 20 2006 601 619 (Pubitemid 46023925)
32. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function J. Comput. Chem. 19 1998 1639 1662 (Pubitemid 128590223)
33. V.J. Hearing, and K. Tsukamoto Enzymatic control of pigmentation in mammals FASEB J. 5 1991 2902 2909 (Pubitemid 21905830)
34. S.M. Son, K.D. Moon, and C.Y. Lee Kinetic study of oxalic acid inhibition on enzymatic browning J. Agric. Food Chem. 48 2000 2071 2074 (Pubitemid 30431190)
35. G. Battaini, E. Monzani, L. Casella, L. Santagostini, and R. Pagliarin Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid J. Biol. Inorg. Chem. 5 2000 262 268 (Pubitemid 30249409)
36. R.L. Dunbrack Jr. Rotamer libraries in the 21st century Curr. Opin. Struct. Biol. 12 2002 431 440