Recent advances in the design and discovery of synthetic tyrosinase inhibitors
Tóm tắt
Từ khóa
Tài liệu tham khảo
Sánchez-Ferrer, 1995, Tyrosinase: a comprehensive review of its mechanism, Biochim. Biophys. Acta, 1247, 1, 10.1016/0167-4838(94)00204-T
Parvez, 2007, Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries, Phytother Res., 21, 805, 10.1002/ptr.2184
Zolghadri, 2019, A comprehensive review on tyrosinase inhibitors, J. Enzym. Inhib. Med. Chem., 34, 279, 10.1080/14756366.2018.1545767
Sugumaran, 1991, Molecular mechanisms for mammalian melanogenesis - comparison with insect cuticular sclerotization, FEBS Lett., 295, 233, 10.1016/0014-5793(91)81431-7
Barrett, 1984, Wound-healing phenoloxidase in larval cuticle of calpodes-ethlius (lepidoptera, hesperiidae), Can. J. Zool., 62, 834, 10.1139/z84-122
Kramer, 1987, Tyrosine metabolism for insect cuticle tanning, Arch. Insect Biochem. Physiol., 6, 279, 10.1002/arch.940060406
Sugumaran, 2016, Critical analysis of the melanogenic pathway in insects and higher animals, Int. J. Mol. Sci., 17, 1753, 10.3390/ijms17101753
Yuan, 2020, Tyrosinase inhibitors as potential antibacterial agents, Eur. J. Med. Chem., 187, 111892, 10.1016/j.ejmech.2019.111892
Casadevall, 2017, Melanin, radiation, and energy transduction in fungi, Microbiol. Spectr., 5, 10.1128/microbiolspec.FUNK-0037-2016
Chung-Yi, 2015, An updated organic classification of tyrosinase inhibitors on melanin biosynthesis, Curr. Org. Chem., 19, 4, 10.2174/1385272819666141107224806
Oetting, 2000, The tyrosinase gene and oculocutaneous albinism type 1 (OCA1): a model for understanding the molecular biology of melanin formation, Pigm. Cell Res., 13, 320, 10.1034/j.1600-0749.2000.130503.x
Friedman, 1996, Food browning and its prevention: an overview, J. Agric. Food Chem., 44, 631, 10.1021/jf950394r
McEvily, 1991, Sulfite alternative prevents shrimp melanosis, Food Technol., 45, 80
2019
Fujimoto, 1999, Changes in thyroid function during development of thyroid hyperplasia induced by kojic acid in F344 rats, Carcinogenesis, 20, 1567, 10.1093/carcin/20.8.1567
McGregor, 2007, Hydroquinone: an evaluation of the human risks from its carcinogenic and mutagenic properties, Crit. Rev. Toxicol., 37, 887, 10.1080/10408440701638970
De Luca, 2020, Discovery of a new potent inhibitor of mushroom tyrosinase (Agaricus bisporus) containing 4-(4-hydroxyphenyl)piperazin-1-yl moiety, Biorg. Med. Chem., 28, 115497, 10.1016/j.bmc.2020.115497
Matoba, 2006, Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis, J. Biol. Chem., 281, 8981, 10.1074/jbc.M509785200
Ismaya, 2011, Crystal structure of Agaricus bisporus mushroom tyrosinase: identity of the tetramer subunits and interaction with tropolone, Biochemistry, 50, 5477, 10.1021/bi200395t
Strothkamp, 1976, Quaternary structure of mushroom tyrosinase, Biochem. Biophys. Res. Commun., 70, 519, 10.1016/0006-291X(76)91077-9
Ando, 2007, Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase, J. Invest. Dermatol., 127, 751, 10.1038/sj.jid.5700683
Mendes, 2014, Design and discovery of mushroom tyrosinase inhibitors and their therapeutic applications, Expet Opin. Drug Discov., 9, 533, 10.1517/17460441.2014.907789
Roulier, 2020, Advances in the design of genuine human tyrosinase inhibitors for targeting melanogenesis and related pigmentations, J. Med. Chem., 63, 13428, 10.1021/acs.jmedchem.0c00994
Singh, 2016, Structural modeling of human tyrosinase protein using computational methods, J. Biotechnol. Res., 2, 15
Yap, 2020, Chicken egg white-advancing from food to skin health therapy: optimization of hydrolysis condition and identification of tyrosinase inhibitor peptides, Foods, 9, 10.3390/foods9091312
Della Longa, 1996, The dinuclear copper site structure of Agaricus bisporus tyrosinase in solution probed by X-ray absorption spectroscopy, J. Biol. Chem., 271, 21025, 10.1074/jbc.271.35.21025
Sanjust, 2003, 3-hydroxykynurenine as a substrate/activator for mushroom tyrosinase, Arch. Biochem. Biophys., 412, 272, 10.1016/S0003-9861(03)00053-5
Beltramini, 1990, The reaction of CN- with the binuclear copper site of Neurospora tyrosinase: its relevance for a comparison between tyrosinase and hemocyanin active sites, Biochim. Biophys. Acta, 1040, 365, 10.1016/0167-4838(90)90134-2
Cramer, 2006, Theoretical models on the Cu2O2 torture track: mechanistic implications for oxytyrosinase and small-molecule analogues, J. Phys. Chem., 110, 1991, 10.1021/jp056791e
Espín, 1999, Slow-binding inhibition of mushroom (Agaricus bisporus) tyrosinase isoforms by tropolone, J. Agric. Food Chem., 47, 2638, 10.1021/jf981055b
Chang, 2009, An updated review of tyrosinase inhibitors, Int. J. Mol. Sci., 10, 2440, 10.3390/ijms10062440
Fenoll, 2001, Analysis and interpretation of the action mechanism of mushroom tyrosinase on monophenols and diphenols generating highly unstable o-quinones, Biochim. Biophys. Acta, 1548, 1, 10.1016/S0167-4838(01)00207-2
Burton, 1994, Biocatalysis with polyphenol oxidase - a Review, Catal. Today, 22, 459, 10.1016/0920-5861(94)80118-5
Wilcox, 1985, Substrate-analog binding to the coupled binuclear copper active-site in tyrosinase, J. Am. Chem. Soc., 107, 4015, 10.1021/ja00299a043
Naish-Byfield, 1992, Oxidation of monohydric phenol substrates by tyrosinase, An oximetric study, Biochem J, 288, 63
Kameyama, 1995, The expression of tyrosinase, tyrosinase-related proteins 1 and 2 (TRP1 and TRP2), the silver protein, and a melanogenic inhibitor in human melanoma cells of differing melanogenic activities, Pigm. Cell Res., 8, 97, 10.1111/j.1600-0749.1995.tb00648.x
MD, 1983, 1
D'Alba, 2018, Melanosomes: biogenesis, properties, and evolution of an ancient organelle, Physiol. Rev., 99, 1, 10.1152/physrev.00059.2017
Tsatmali, 2002, Melanocyte function and its control by melanocortin peptides, J. Histochem. Cytochem., 50, 125, 10.1177/002215540205000201
Thakur, 2009, Chapter 4 - structural and biochemical changes in aging skin and their impact on skin permeability barrier, 55
Barozzi, 2015, Audiovestibular disorders as autoimmune reaction in patients with melanoma, Med. Hypotheses, 85, 10.1016/j.mehy.2015.06.009
Pillaiyar, 2017, Downregulation of melanogenesis: drug discovery and therapeutic options, Drug Discov. Today, 22, 282, 10.1016/j.drudis.2016.09.016
Hearing, 1987, Mammalian tyrosinase—the critical regulatory control point in melanocyte pigmentation, Int. J. Biochem., 19, 1141, 10.1016/0020-711X(87)90095-4
Pillaiyar, 2018, Inhibitors of melanogenesis: an updated review, J. Med. Chem., 61, 7395, 10.1021/acs.jmedchem.7b00967
Pillaiyar, 2015, Inhibitors of melanogenesis: a patent review (2009 - 2014), Expert Opin. Ther. Pat., 25, 775, 10.1517/13543776.2015.1039985
Ullah, 2016, Tyrosinase inhibitors: a patent review (2011-2015), Expert Opin. Ther. Pat., 26, 347, 10.1517/13543776.2016.1146253
Lai, 2018, Structure and function of human tyrosinase and tyrosinase-related proteins, Chemistry, 24, 47, 10.1002/chem.201704410
Sánchez-Ferrer, 1995, Tyrosinase: a comprehensive review of its mechanism, Biochim. Biophys. Acta, 1247, 1, 10.1016/0167-4838(94)00204-T
Kobayashi, 1994, Tyrosinase related protein 1 (TRP1) functions as a DHICA oxidase in melanin biosynthesis, EMBO (Eur. Mol. Biol. Organ.) J., 13, 5818, 10.1002/j.1460-2075.1994.tb06925.x
Boissy, 1998, Human tyrosinase related protein-1 (TRP-1) does not function as a DHICA oxidase activity in contrast to murine TRP-1, Exp. Dermatol., 7, 198, 10.1111/j.1600-0625.1998.tb00324.x
Lai, 2017, Structure of human tyrosinase related protein 1 reveals a binuclear zinc active site important for melanogenesis, Angew Chem. Int. Ed. Engl., 56, 9812, 10.1002/anie.201704616
Kovacs, 2016, The role of Wnt/β-catenin signaling pathway in melanoma epithelial-to-mesenchymal-like switching: evidences from patients-derived cell lines, Oncotarget, 7, 43295, 10.18632/oncotarget.9232
Park, 2009, Cellular mechanisms regulating human melanogenesis, Cell. Mol. Life Sci., 66, 1493, 10.1007/s00018-009-8703-8
Wang, 2017, Precise role of dermal fibroblasts on melanocyte pigmentation, J. Dermatol. Sci., 88, 159, 10.1016/j.jdermsci.2017.06.018
Tsang, 2012, Inhibition of the p38 and PKA signaling pathways is associated with the anti-melanogenic activity of Qian-wang-hong-Bai-san, a Chinese herbal formula, in B16 cells, J. Ethnopharmacol., 141, 622, 10.1016/j.jep.2011.08.043
Newton, 2007, Human melanocytes expressing MC1R variant alleles show impaired activation of multiple signaling pathways, Peptides, 28, 2387, 10.1016/j.peptides.2007.10.003
Tachibana, 2001, Cochlear melanocytes and MITF signaling, JIDSP, 6, 95
Levy, 2006, MITF: master regulator of melanocyte development and melanoma oncogene, Trends Mol. Med., 12, 406, 10.1016/j.molmed.2006.07.008
Ye, 2010, Involvement of p38 MAPK signaling pathway in the anti-melanogenic effect of San-Bai-tang, a Chinese herbal formula, in B16 cells, J. Ethnopharmacol., 132, 533, 10.1016/j.jep.2010.09.007
Qu, 2020, Catalysis-based specific detection and inhibition of tyrosinase and their application, J Pharm Anal, 10, 414, 10.1016/j.jpha.2020.07.004
Liu, 2020
Niu, 2017, Upregulation of melanogenesis and tyrosinase activity: potential agents for vitiligo, Molecules, 22
Pillaiyar, 2017, Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors, J. Enzym. Inhib. Med. Chem., 32, 403, 10.1080/14756366.2016.1256882
Zucca, 2014, Neuromelanin of the human substantia nigra: an update, Neurotox. Res., 25, 13, 10.1007/s12640-013-9435-y
Pan, 2011, The association between Parkinson's disease and melanoma, Int. J. Canc., 128, 2251, 10.1002/ijc.25912
Ikemoto, 1998, Does tyrosinase exist in neuromelanin-pigmented neurons in the human substantia nigra?, Neurosci. Lett., 253, 198, 10.1016/S0304-3940(98)00649-1
Hasegawa, 2010, Tyrosinase-expressing neuronal cell line as in vitro model of Parkinson's disease, Int. J. Mol. Sci., 11, 1082, 10.3390/ijms11031082
Olsen, 2006, Malignant melanoma and other types of cancer preceding Parkinson disease, Epidemiology, 17, 10.1097/01.ede.0000229445.90471.5e
Bertoni, 2010, Increased melanoma risk in Parkinson disease: a prospective clinicopathological study, Arch. Neurol., 67, 347, 10.1001/archneurol.2010.1
Gao, 2009, Family history of melanoma and Parkinson disease risk, Neurology, 73, 1286, 10.1212/WNL.0b013e3181bd13a1
Ostendorf, 2020, Common germline variants of the human APOE gene modulate melanoma progression and survival, Nat. Med., 26, 1048, 10.1038/s41591-020-0879-3
2021
Fu, 1997, Tyrosine and phenylalanine restriction induces G0/G1 cell cycle arrest in murine melanoma in vitro and in vivo, Nutr. Canc., 29, 104, 10.1080/01635589709514610
Yamaguchi, 2008, Melanin mediated apoptosis of epidermal cells damaged by ultraviolet radiation: factors influencing the incidence of skin cancer, Arch. Dermatol. Res., 300, S43, 10.1007/s00403-007-0807-0
Videira, 2013, Mechanisms regulating melanogenesis, An. Bras. Dermatol., 88, 76, 10.1590/S0365-05962013000100009
Slominski, 2012, Sensing the environment: regulation of local and global homeostasis by the skin's neuroendocrine system, Adv. Anat. Embryol. Cell Biol., 212, 1, 10.1007/978-3-642-19683-6_1
Jawaid, 2009, Tyrosinase activated melanoma prodrugs, Anticancer Agents Med. Chem., 9, 717, 10.2174/187152009789056886
Kang, 2003, Depigmenting activity and low cytotoxicity of alkoxy benzoates or alkoxy cinnamte in cultured melanocytes, Chem. Pharm. Bull. (Tokyo), 51, 1085, 10.1248/cpb.51.1085
Jin, 1999, Aloesin and arbutin inhibit tyrosinase activity in a synergistic manner via a different action mechanism, Arch Pharm. Res. (Seoul), 22, 232, 10.1007/BF02976355
Curto, 1999, Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors, Biochem. Pharmacol., 57, 663, 10.1016/S0006-2952(98)00340-2
Sarkar, 2013, Cosmeceuticals for hyperpigmentation: what is available?, 6, 4
Jacobus Berlitz, 2019, Azelaic acid-loaded nanoemulsion with hyaluronic acid - a new strategy to treat hyperpigmentary skin disorders, Drug Dev. Ind. Pharm., 45, 642, 10.1080/03639045.2019.1569032
Na, 2019, Resveratrol as a multifunctional topical hypopigmenting agent, Int. J. Mol. Sci., 20, 10.3390/ijms20040956
Honisch, 2020, Isolation of a tyrosinase inhibitor from unripe grapes juice: a spectrophotometric study, Food Chem., 305, 125506, 10.1016/j.foodchem.2019.125506
Liu, 2021, Valonea tannin: tyrosinase inhibition activity, structural elucidation and insights into the inhibition mechanism, Molecules, 26, 2747, 10.3390/molecules26092747
Arroo, 2020, Flavones as tyrosinase inhibitors: kinetic studies in vitro and in silico, Phytochem. Anal., 31, 314, 10.1002/pca.2897
Yu, 2021, Clinical efficacy and safety of nano-microneedle-assisted phenylethyl resorcinol for the treatment of infraorbital dark circles, J. Cosmet. Dermatol., 20, 884, 10.1111/jocd.13641
Schmaus, 2006, 4-(1-Phenylethyl) 1,3-benzenediol: a new highly potent lightning agent, J. Cosmet. Sci., 57, 197
Jiang, 2018, Investigation of the pro-apoptotic effects of arbutin and its acetylated derivative on murine melanoma cells, Int. J. Mol. Med., 41, 1048
Ishioka, 2019, Resorcinol alkyl glucosides as potent tyrosinase inhibitors, Bioorg. Med. Chem. Lett, 29, 313, 10.1016/j.bmcl.2018.11.029
Iwadate, 2015, Rhododendrol glycosides as stereospecific tyrosinase inhibitors, Bioorg. Med. Chem., 23, 6650, 10.1016/j.bmc.2015.09.014
Park, 2014, Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis, Arch. Dermatol. Res., 306, 475, 10.1007/s00403-014-1440-3
Liu, 2015, Synthesis and biological evaluation of resveratrol derivatives as melanogenesis inhibitors, Molecules, 20, 16933, 10.3390/molecules200916933
Tanaka, 2019, Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton, Carbohydr. Res., 472, 42, 10.1016/j.carres.2018.11.006
Tsang, 2016, Inhibition of pancreatic oxidative damage by stilbene derivative dihydro-resveratrol: implication for treatment of acute pancreatitis, Sci. Rep., 6, 22859, 10.1038/srep22859
Ashraf, 2015, Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors, J. Enzym. Inhib. Med. Chem., 30, 874, 10.3109/14756366.2014.979346
Li, 2018, Identification by shape-based virtual screening and evaluation of new tyrosinase inhibitors, PeerJ, 6
Iraji, 2020, Synthesis, biological evaluation and molecular docking analysis of vaniline-benzylidenehydrazine hybrids as potent tyrosinase inhibitors, BMC Chem., 14, 28, 10.1186/s13065-020-00679-1
Pintus, 2017, New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins: anti-melanogenesis and antioxidant activities, and computational molecular modeling studies, Bioorg. Med. Chem., 25, 1687, 10.1016/j.bmc.2017.01.037
Suthar, 2017, Design, synthesis and biological evaluation of oxindole-based chalcones as small-molecule inhibitors of melanogenic tyrosinase, Chem. Pharm. Bull. (Tokyo), 65, 833, 10.1248/cpb.c17-00301
Jung, 2019, In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives, Comput. Struct. Biotechnol. J., 17, 1255, 10.1016/j.csbj.2019.07.017
Radhakrishnan, 2015, Inhibitory kinetics of novel 2,3-dihydro-1H-inden-1-one chalcone-like derivatives on mushroom tyrosinase, Bioorg. Med. Chem. Lett, 25, 5495, 10.1016/j.bmcl.2015.10.071
Radhakrishnan, 2015, Development of hydroxylated naphthylchalcones as polyphenol oxidase inhibitors: synthesis, biochemistry and molecular docking studies, Bioorg. Chem., 63, 116, 10.1016/j.bioorg.2015.10.003
Radhakrishnan, 2015, Integrated kinetic studies and computational analysis on naphthyl chalcones as mushroom tyrosinase inhibitors, Bioorg. Med. Chem. Lett, 25, 4085, 10.1016/j.bmcl.2015.08.033
Radhakrishnan, 2016, Evaluation of novel chalcone oximes as inhibitors of tyrosinase and melanin formation in B16 cells, Arch. Pharm. (Weinheim), 349, 20, 10.1002/ardp.201500298
Radhakrishnan, 2015, Azachalcones: a new class of potent polyphenol oxidase inhibitors, Bioorg. Med. Chem. Lett, 25, 1753, 10.1016/j.bmcl.2015.02.060
Kim, 2018, A potent tyrosinase inhibitor, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with anti-melanogenesis properties in α-MSHand IBMX-induced B16F10 melanoma cells, Molecules, 23
Jung, 2020, (E)-1-(furan-2-yl)-(substituted phenyl)prop-2-en-1-one derivatives as tyrosinase inhibitors and melanogenesis inhibition: an in vitro and in silico study, Molecules, 25, 10.3390/molecules25225460
Ashraf, 2020, Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies, J. Biomol. Struct. Dyn., 1
Kim, 2016, Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone, Biochem. Biophys. Res. Commun., 480, 648, 10.1016/j.bbrc.2016.10.110
Zheng, 2016, One-pot green synthesis of 1,3,5-triarylpentane-1,5-dione and triarylmethane derivatives as a new class of tyrosinase inhibitors, Bioorg. Med. Chem. Lett, 26, 795, 10.1016/j.bmcl.2015.12.092
Yu, 2019, Study on synthesis and biological evaluation of 3-aryl substituted xanthone derivatives as novel and potent tyrosinase inhibitors, Chem. Pharm. Bull. (Tokyo), 67, 1232, 10.1248/cpb.c19-00572
Bukhari, 2014, Biological activity and molecular docking studies of curcumin-related α,β-unsaturated carbonyl-based synthetic compounds as anticancer agents and mushroom tyrosinase inhibitors, J. Agric. Food Chem., 62, 5538, 10.1021/jf501145b
Son, 2015, (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., 23, 7728, 10.1016/j.bmc.2015.11.015
Lee, 2019, Inhibitory effects of N-(acryloyl)benzamide derivatives on tyrosinase and melanogenesis, Bioorg. Med. Chem., 27, 3929, 10.1016/j.bmc.2019.07.034
Dettori, 2020, Synthesis and studies of the inhibitory effect of hydroxylated phenylpropanoids and biphenols derivatives on tyrosinase and laccase enzymes, Molecules, 25, 10.3390/molecules25112709
Zhao, 2019, Synthesis and anti-tyrosinase mechanism of the substituted vanillyl cinnamate analogues, Bioorg. Chem., 93, 103316, 10.1016/j.bioorg.2019.103316
Cui, 2017, Inhibition kinetics and molecular simulation of p-substituted cinnamic acid derivatives on tyrosinase, Int. J. Biol. Macromol., 95, 1289, 10.1016/j.ijbiomac.2016.11.027
Ghafary, 2019, Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors, Int. J. Biol. Macromol., 135, 978, 10.1016/j.ijbiomac.2019.05.201
Ha, 2018, Dimeric cinnamoylamide analogues for regulation of tyrosinase activity in melanoma cells: a role of diamide-link chain length, Bioorg. Med. Chem., 26, 6015, 10.1016/j.bmc.2018.10.036
Sheng, 2018, Design, synthesis and evaluation of cinnamic acid ester derivatives as mushroom tyrosinase inhibitors, Medchemcomm, 9, 853, 10.1039/C8MD00099A
Nazir, 2020, Hydroxyl substituted benzoic acid/cinnamic acid derivatives: tyrosinase inhibitory kinetics, anti-melanogenic activity and molecular docking studies, Bioorg. Med. Chem. Lett, 30, 126722, 10.1016/j.bmcl.2019.126722
Abbas, 2017, Development of highly potent melanogenesis inhibitor by in vitro, in vivo and computational studies, Drug Des. Dev. Ther., 11, 2029, 10.2147/DDDT.S137550
Rafiq, 2019, Synthesis, computational studies, tyrosinase inhibitory kinetics and antimelanogenic activity of hydroxy substituted 2-[(4-acetylphenyl)amino]-2-oxoethyl derivatives, J. Enzym. Inhib. Med. Chem., 34, 1, 10.1080/14756366.2019.1654468
Ashraf, 2015, Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase, Bioorg. Med. Chem., 23, 5870, 10.1016/j.bmc.2015.06.068
Ashraf, 2017, Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies, PloS One, 12, 10.1371/journal.pone.0178069
Ullah, 2019, Synthesis of cinnamic amide derivatives and their anti-melanogenic effect in α-MSH-stimulated B16F10 melanoma cells, Eur. J. Med. Chem., 161, 78, 10.1016/j.ejmech.2018.10.025
Ullah, 2019, Antioxidant, anti-tyrosinase and anti-melanogenic effects of (E)-2,3-diphenylacrylic acid derivatives, Bioorg. Med. Chem., 27, 2192, 10.1016/j.bmc.2019.04.020
Ullah, 2018, Design, synthesis and anti-melanogenic effect of cinnamamide derivatives, Bioorg. Med. Chem., 26, 5672, 10.1016/j.bmc.2018.10.014
Ullah, 2019, Tyrosinase inhibition and anti-melanin generation effect of cinnamamide analogues, Bioorg. Chem., 87, 43, 10.1016/j.bioorg.2019.03.001
Kim, 2018, The tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold, Bioorg. Med. Chem., 26, 3882, 10.1016/j.bmc.2018.05.047
Oliveira, 2020, Coumaric acid analogues inhibit growth and melanin biosynthesis in Cryptococcus neoformans and potentialize amphotericin B antifungal activity, Eur. J. Pharmaceut. Sci., 153, 105473, 10.1016/j.ejps.2020.105473
Carcelli, 2020, Hydroxyphenyl thiosemicarbazones as inhibitors of mushroom tyrosinase and antibrowning agents, Food Chem., 303, 125310, 10.1016/j.foodchem.2019.125310
Okajima, 2019, Azepine derivative T4FAT, a new copper chelator, inhibits tyrosinase, Biochem. Biophys. Res. Commun., 509, 209, 10.1016/j.bbrc.2018.12.105
You, 2015, Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: from potent activators to highly efficient inhibitors, Eur. J. Med. Chem., 93, 255, 10.1016/j.ejmech.2015.02.013
Hałdys, 2020, Halogenated aromatic thiosemicarbazones as potent inhibitors of tyrosinase and melanogenesis, Bioorg. Chem., 94, 103419, 10.1016/j.bioorg.2019.103419
Hosseinpoor, 2020, A series of benzylidenes linked to hydrazine-1-carbothioamide as tyrosinase inhibitors: synthesis, biological evaluation and structure-activity relationship, Chem. Biodivers., 17, 10.1002/cbdv.202000285
Cabezudo, 2020, Effect directed synthesis of a new tyrosinase inhibitor with anti-browning activity, Food Chem., 341, 128232, 10.1016/j.foodchem.2020.128232
Song, 2020, Design, synthesis, biological evaluation and inhibition mechanism of 3-/4-alkoxy phenylethylidenethiosemicarbazides as new, potent and safe tyrosinase inhibitors, Chem. Pharm. Bull. (Tokyo), 68, 369, 10.1248/cpb.c19-00949
Soares, 2017, Thiosemicarbazones as inhibitors of tyrosinase enzyme, Bioorg. Med. Chem. Lett, 27, 3546, 10.1016/j.bmcl.2017.05.057
Song, 2017, Study on the design, synthesis and structure-activity relationships of new thiosemicarbazone compounds as tyrosinase inhibitors, Eur. J. Med. Chem., 139, 815, 10.1016/j.ejmech.2017.08.033
You, 2015, Rational design, synthesis and structure-activity relationships of 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues as novel tyrosinase inhibitors, Bioorg. Med. Chem., 23, 924, 10.1016/j.bmc.2015.01.024
Dong, 2017, Molecular docking and QSAR analyses of aromatic heterocycle thiosemicarbazone analogues for finding novel tyrosinase inhibitors, Bioorg. Chem., 75, 106, 10.1016/j.bioorg.2017.07.002
Liu, 2017, Novel inhibitors of tyrosinase produced by the 4-substitution of TCT (П), Int. J. Biol. Macromol., 103, 1096, 10.1016/j.ijbiomac.2017.05.036
Xie, 2016, Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: insights from fluorescence, (1)H NMR titration and molecular docking studies, Food Chem., 190, 709, 10.1016/j.foodchem.2015.05.124
Xu, 2017, Novel inhibitors of tyrosinase produced by the 4-substitution of TCT, Food Chem., 221, 1530, 10.1016/j.foodchem.2016.10.140
Choi, 2015, Analogues of ethionamide, a drug used for multidrug-resistant tuberculosis, exhibit potent inhibition of tyrosinase, Eur. J. Med. Chem., 106, 157, 10.1016/j.ejmech.2015.10.033
Choi, 2015, Repositioning of thiourea-containing drugs as tyrosinase inhibitors, Int. J. Mol. Sci., 16, 28534, 10.3390/ijms161226114
Liu, 2016, Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors, Bioorg. Med. Chem., 24, 1866, 10.1016/j.bmc.2016.03.013
Larik, 2017, Design, synthesis, kinetic mechanism and molecular docking studies of novel 1-pentanoyl-3-arylthioureas as inhibitors of mushroom tyrosinase and free radical scavengers, Eur. J. Med. Chem., 141, 273, 10.1016/j.ejmech.2017.09.059
Mustafa, 2019, Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers, Bioorg. Chem., 90, 103063, 10.1016/j.bioorg.2019.103063
Ashooriha, 2020, Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors, Eur. J. Med. Chem., 201, 112480, 10.1016/j.ejmech.2020.112480
Singh, 2020, Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity, J. Enzym. Inhib. Med. Chem., 35, 1562, 10.1080/14756366.2020.1801669
Brasil, 2017, Inhibition of tyrosinase by 4H-chromene analogs: synthesis, kinetic studies, and computational analysis, Chem. Biol. Drug Des., 90, 804, 10.1111/cbdd.13001
Xie, 2017, Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase, Bioorg. Med. Chem. Lett, 27, 530, 10.1016/j.bmcl.2016.12.027
Chen, 2019, Anti-melanogenesis of novel kojic acid derivatives in B16F10 cells and zebrafish, Int. J. Biol. Macromol., 123, 723, 10.1016/j.ijbiomac.2018.11.031
Xie, 2015, Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4-triazole as potent tyrosinase inhibitors, Chem. Biol. Drug Des., 86, 1087, 10.1111/cbdd.12577
Shao, 2018, Novel hydroxypyridinone derivatives containing an oxime ether moiety: synthesis, inhibition on mushroom tyrosinase and application in anti-browning of fresh-cut apples, Food Chem., 242, 174, 10.1016/j.foodchem.2017.09.054
Zhao, 2016, Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors, Bioorg. Med. Chem. Lett, 26, 3103, 10.1016/j.bmcl.2016.05.006
Rezaei, 2018, Evaluation of thiazolidinone derivatives as a new class of mushroom tyrosinase inhibitors, Int. J. Biol. Macromol., 108, 205, 10.1016/j.ijbiomac.2017.11.147
Mutahir, 2017, Organocatalyzed and mechanochemical solvent-free synthesis of novel and functionalized bis-biphenyl substituted thiazolidinones as potent tyrosinase inhibitors: SAR and molecular modeling studies, Eur. J. Med. Chem., 134, 406, 10.1016/j.ejmech.2017.04.021
Tang, 2016, Molecular docking studies and biological evaluation of 1,3,4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors, Bioorg. Chem., 69, 29, 10.1016/j.bioorg.2016.09.007
Piechowska, 2019, Discovery of tropinone-thiazole derivatives as potent caspase 3/7 activators, and noncompetitive tyrosinase inhibitors with high antiproliferative activity: rational design, one-pot tricomponent synthesis, and lipophilicity determination, Eur. J. Med. Chem., 175, 162, 10.1016/j.ejmech.2019.05.006
Kim, 2017, Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives, Drug Des. Dev. Ther., 11, 827, 10.2147/DDDT.S131538
Kang, 2015, (Z)-2-(Benzo[d]thiazol-2-ylamino)-5-(substituted benzylidene)thiazol-4(5H)-one derivatives as novel tyrosinase inhibitors, Biol. Pharm. Bull., 38, 1227, 10.1248/bpb.b15-00300
Choi, 2014, MHY884, a newly synthesized tyrosinase inhibitor, suppresses UVB-induced activation of NF-κB signaling pathway through the downregulation of oxidative stress, Bioorg. Med. Chem. Lett, 24, 1344, 10.1016/j.bmcl.2014.01.040
Bang, 2018, Evaluation of the novel synthetic tyrosinase inhibitor (z)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (mhy1498) in vitro and in silico, Molecules, 23
Hamidian, 2015, Synthesis of novel compounds containing morpholine and 5(4H)-oxazolone rings as potent tyrosinase inhibitors, Bioorg. Med. Chem., 23, 7089, 10.1016/j.bmc.2015.09.015
Channar, 2017, Synthesis, computational studies and enzyme inhibitory kinetics of substituted methyl[2-(4-dimethylamino-benzylidene)-hydrazono)-4-oxo-thiazolidin-5-ylidene]acetates as mushroom tyrosinase inhibitors, Bioorg. Med. Chem., 25, 5929, 10.1016/j.bmc.2017.09.009
Oyama, 2016, Discovery of a new type of scaffold for the creation of novel tyrosinase inhibitors, Bioorg. Med. Chem., 24, 4509, 10.1016/j.bmc.2016.07.060
Oyama, 2017, Structural insight into the active site of mushroom tyrosinase using phenylbenzoic acid derivatives, Bioorg. Med. Chem. Lett, 27, 2868, 10.1016/j.bmcl.2017.04.074
Karimian, 2020
Wang, 2016, 2-(4-Fluorophenyl)-quinazolin-4(3H)-one as a novel tyrosinase inhibitor: synthesis, inhibitory activity, and mechanism, Bioorg. Med. Chem., 24, 4620, 10.1016/j.bmc.2016.07.068
Chortani, 2019, Synthesis, biological evaluation and molecular docking analysis of novel benzopyrimidinone derivatives as potential anti-tyrosinase agents, Bioorg. Chem., 92, 103270, 10.1016/j.bioorg.2019.103270
Dige, 2019, Ultrasound mediated efficient synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as potent tyrosinase inhibitors: mechanistic approach through chemoinformatics and molecular docking studies, Bioorg. Chem., 92, 103201, 10.1016/j.bioorg.2019.103201
Ranjbar, 2020, 1,2,3-Triazole-linked 5-benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free-radical scavengers, Arch. Pharm. (Weinheim), 353, 10.1002/ardp.202000058
Chen, 2014, Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors, Bioorg. Med. Chem., 22, 3279, 10.1016/j.bmc.2014.04.060
Rafiq, 2016, Synthesis, structural elucidation and bioevaluation of 4-amino-1,2,4-triazole-3-thione's Schiff base derivatives, Arch Pharm. Res. (Seoul), 39, 161, 10.1007/s12272-015-0688-2
Yu, 2015, Synthesis of triazole schiff's base derivatives and their inhibitory kinetics on tyrosinase activity, PloS One, 10
Gheibi, 2015, Characterization of inhibitory effects of the potential therapeutic inhibitors, benzoic acid and pyridine derivatives, on the monophenolase and diphenolase activities of tyrosinase, Iran J Basic Med Sci, 18, 122
Ferro, 2016, Searching for indole derivatives as potential mushroom tyrosinase inhibitors, J. Enzym. Inhib. Med. Chem., 31, 398
Ferro, 2017, Chemical exploration of 4-(4-fluorobenzyl)piperidine fragment for the development of new tyrosinase inhibitors, Eur. J. Med. Chem., 125, 992, 10.1016/j.ejmech.2016.10.030
Vittorio, 2020, 4-fluorobenzylpiperazine-containing derivatives as efficient inhibitors of mushroom tyrosinase, ChemMedChem, 15, 1757, 10.1002/cmdc.202000125
Ferro, 2018, Targeting tyrosinase: development and structural insights of novel inhibitors bearing arylpiperidine and arylpiperazine fragments, J. Med. Chem., 61, 3908, 10.1021/acs.jmedchem.7b01745
Ielo, 2019, Exploiting the 1-(4-fluorobenzyl)piperazine fragment for the development of novel tyrosinase inhibitors as anti-melanogenic agents: design, synthesis, structural insights and biological profile, Eur. J. Med. Chem., 178, 380, 10.1016/j.ejmech.2019.06.019
Wolińska, 2019, Phosphonic and phosphinic acid derivatives as novel tyrosinase inhibitors: kinetic studies and molecular docking, Chem. Biodivers., 16, 10.1002/cbdv.201900167
Gardelly, 2016, Synthesis of novel diazaphosphinanes coumarin derivatives with promoted cytotoxic and anti-tyrosinase activities, Bioorg. Med. Chem. Lett, 26, 2450, 10.1016/j.bmcl.2016.03.108
Choi, 2016, Ensemble-based virtual screening led to the discovery of new classes of potent tyrosinase inhibitors, J. Chem. Inf. Model., 56, 354, 10.1021/acs.jcim.5b00484
Vittorio, 2020, A combination of pharmacophore and docking-based virtual screening to discover new tyrosinase inhibitors, Mol. Inform., 39, 10.1002/minf.201900054
Mahdavi, 2018, Synthesis of new benzimidazole-1,2,3-triazole hybrids as tyrosinase inhibitors, Chem. Biodivers., 15, 10.1002/cbdv.201800120
Ghani, 2019, Carbazole and hydrazone derivatives as new competitive inhibitors of tyrosinase: experimental clues to binuclear copper active site binding, Bioorg. Chem., 83, 235, 10.1016/j.bioorg.2018.10.026
Mirmortazavi, 2019, Evaluation of novel pyrimidine derivatives as a new class of mushroom tyrosinase inhibitor, Drug Des. Dev. Ther., 13, 2169, 10.2147/DDDT.S209324
Vanjare, 2020
Saeed, 2017, Synthesis, molecular docking studies of coumarinyl-pyrazolinyl substituted thiazoles as non-competitive inhibitors of mushroom tyrosinase, Bioorg. Chem., 74, 187, 10.1016/j.bioorg.2017.08.002
Qamar, 2019, Novel 1,3-oxazine-tetrazole hybrids as mushroom tyrosinase inhibitors and free radical scavengers: synthesis, kinetic mechanism, and molecular docking studies, Chem. Biol. Drug Des., 93, 123, 10.1111/cbdd.13352
Cordes, 2013, Expression in non-melanogenic systems and purification of soluble variants of human tyrosinase, Biol. Chem., 394, 685, 10.1515/hsz-2012-0300
Mann, 2018, Structure-activity relationships of thiazolyl resorcinols, potent and selective inhibitors of human tyrosinase, Int. J. Mol. Sci., 19, 10.3390/ijms19030690
Mann, 2018, Inhibition of human tyrosinase requires molecular motifs distinctively different from mushroom tyrosinase, J. Invest. Dermatol., 138, 1601, 10.1016/j.jid.2018.01.019
Arrowitz, 2019, Effective tyrosinase inhibition by thiamidol results in significant improvement of mild to moderate melasma, J. Invest. Dermatol., 139, 1691, 10.1016/j.jid.2019.02.013
Wu, 2016, Near-infrared fluorescent probe with new recognition moiety for specific detection of tyrosinase activity: design, synthesis, and application in living cells and zebrafish, Angew Chem. Int. Ed. Engl., 55, 14728, 10.1002/anie.201609895
Chang, 2012, Natural melanogenesis inhibitors acting through the down-regulation of tyrosinase activity, Materials, 5, 1661, 10.3390/ma5091661
Wang, 2006, Tyrosinase maturation through the mammalian secretory pathway: bringing color to life, Pigm. Cell Res., 19, 3, 10.1111/j.1600-0749.2005.00288.x
Lu, 2020, Emergence of allosteric drug-resistance mutations: new challenges for allosteric drug discovery, Drug Discov. Today, 25, 177, 10.1016/j.drudis.2019.10.006