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Analytical Chemistry

A novel synthetic compound, (Z)-5-(3-hydroxy-4-methoxybenzylidene)-2-iminothiazolidin-4-one (MHY773) inhibits mushroom tyrosinase

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Pages 759-767 | Received 17 Oct 2017, Accepted 06 Feb 2018, Published online: 09 Mar 2018

References

  • Spritz RA, Hearing VJ Jr., Hirschhorn K. Genetic disorders of pigmentation. In advanced human genetics. Springer: US; 1994.10.1007/978-1-4757-9062-7
  • Wong G, Pawelek J. Melanocyte-stimulating hormone promotes activation of pre-existing tyrosinase molecules in Cloudman S91 melanoma cells. Nature. 1975;255:644–646.10.1038/255644a0
  • Halaban R, Pomerantz SH, Marshall S, et al. Tyrosinase activity and abundance in cloudman melanoma cells. Arch. Biochem Biophys. 1984;230:383–387.10.1016/0003-9861(84)90121-8
  • Hunt G, Todd C, Cresswell JE, et al. Alpha-melanocyte stimulating hormone and its analogue Nle4DPhe7 alpha-MSH affect morphology, tyrosinase activity and melanogenesis in cultured human melanocytes. J Cell Sci. 1994;107:205–211.
  • Friedman M. Food browning and its prevention: an overview. J Agric Food Chem. 1996;44:631–653.10.1021/jf950394r
  • Matsuura R, Ukeda H, Sawamura M. Tyrosinase inhibitory activity of citrus essential oils. J Agric Food Chem. 2006;54:2309–2313.10.1021/jf051682i
  • Kim YJ, Uyama H. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci. 2005;62:1707–1723.10.1007/s00018-005-5054-y
  • Parvez S, Kang M, Chung HS, et al. Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother Res. 2007;21:805–816.10.1002/(ISSN)1099-1573
  • Solano F, Briganti S, Picardo M, et al. Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res. 2006;19:550–571.10.1111/pcr.2006.19.issue-6
  • Chang TS. An updated review of tyrosinase inhibitors. Int J Mol Sci. 2009;10:2440–2475.10.3390/ijms10062440
  • Seo SY, Sharma VK, Sharma N. Mushroom tyrosinase: recent prospects. J Agric Food Chem. 2003;51:2837–2853.10.1021/jf020826f
  • Khan MT. Novel tyrosinase inhibitors from natural resources - their computational studies. Curr Med Chem. 2012;19:2262–2272.10.2174/092986712800229041
  • Halder RM, Richards GM. Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004;9:1–3.
  • Burnett CL, Bergfeld WF, Belsito DV, et al. Final report of the safety assessment of kojic acid as used in cosmetics. Int J Toxicol. 2010;29:244S–273S.10.1177/1091581810385956
  • Draelos ZD. Skin lightening preparations and the hydroquinone controversy. Dermatol Ther. 2007;20:308–313.10.1111/dth.2007.20.issue-5
  • Kim HR, Lee HJ, Choi YJ, et al. Benzylidene-linked thiohydantoin derivatives as inhibitors of tyrosinase and melanogenesis: importance of the β-phenyl-α, β-unsaturated carbonyl functionality. Med Chem Commun. 2014;5:1410–1417.10.1039/C4MD00171K
  • Son S, Kim H, Yun HY, et al. (E)-2-Cyano-3-(substituted phenyl)acrylamide analogs as potent inhibitors of tyrosinase: A linear β-phenyl-α,β-unsaturated carbonyl scaffold. Bioorg Med Chem. 2015;23:7728–7734.10.1016/j.bmc.2015.11.015
  • No JK, Soung DY, Kim YJ, et al. Inhibition of tyrosinase by green tea components. Life Sci. 1999;65:241–246.
  • Kang KH, Lee B, Son S, et al. (Z)-2-(Benzo[d]thiazol-2-ylamino)-5-(substituted benzylidene)thiazol-4(5H)-one derivatives as novel tyrosinase inhibitors. Biol Pharm Bull. 2015;38:1227–1233.10.1248/bpb.b15-00300
  • Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc. 1934;56:658–666.10.1021/ja01318a036
  • Dixon M. The determination of enzyme inhibitor constants. Biochem J. 1953;55:170–171.10.1042/bj0550170
  • Cornish-Bowden AC. A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors. Biochem J. 1974;137:143–144.10.1042/bj1370143
  • Ismaya WT, Rozeboom HJ, Weijn A, et al. Crystal structure of Agaricus bisporus mushroom tyrosinase: identity of the tetramer subunits and interaction with tropolone. Biochemistry. 2011;50:5477–5486.10.1021/bi200395t
  • Huey R, Morris GM, Olson AJ, et al. A semiempirical free energy force field with charge-based desolvation. J Comput Chem. 2007;28:1145–1152.10.1002/(ISSN)1096-987X
  • Wolber G, Langer T. LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J Chem Inf Model. 2005;45:160–169.10.1021/ci049885e
  • Bilodeau ML, Greulich JD, Hullinger RL, et al. BMP-2 stimulates tyrosinase gene expression and melanogenesis in differentiated melanocytes. Pigment Cell Res. 2001;14:328–336.10.1034/j.1600-0749.2001.140504.x
  • Wendt F, Näther C, Tuczek F. Tyrosinase and catechol oxidase activity of copper (I) complexes supported by imidazole-based ligands: structure-reactivity correlations. J Biol Inorg Chem. 2016;21:777–792.10.1007/s00775-016-1370-y

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