Tyrosinase inhibitors: a patent review (2011-2015)

References

• Bourquelot E, Bertrand G. Le bleuissement et le noircissement des champignons. C R Soc Biol. 1895;47:582–584.
   Google Scholar
• Ramsden CA, Riley PA. Mechanistic studies of tyrosinase suicide inactivation. Arkivoc. 2010;1:260–274.
   Google Scholar
• Faccio G, Kruus K, Saloheimo M, et al. Bacterial tyrosinases and their applications. Pro Biochem. 2012;47(12):1749–1760.
   Web of Science ®Google Scholar
• Chang T. Tyrosinase and tyrosinase inhibitors. J Biocatal Biotransformation. 2012;1:2.
   Google Scholar
• Nikitina V, Vetchinkina E, Ponomareva E, et al. Phenol oxidase activity in bacteria of the genus Azospirillum. Microbiology. 2010;79(3):327–333.
   Web of Science ®Google Scholar
• Piñero S, Rivera J, Romero D, et al. Tyrosinase from Rhizobium etli is involved in nodulation efficiency and symbiosis-associated stress resistance. J Mol Microbiol Biotechnol. 2007;13(1–3):35–44.
   PubMed Web of Science ®Google Scholar
• Michalik J, Emilianowicz-Czerska W, Switalski L, et al. Monophenol monooxygenase and lincomysin biosynthesis in Streptomyces lincolnensis. Antimicrob Agents Chemother. 1975;8(5):526–531.
   PubMed Web of Science ®Google Scholar
• Taft A, Chen C, Li J, et al.. Molecular cloning of two prophenoloxidase genes from the mosquito Aedes aegypti. Insect Mol Biol. 2001;10(1):97–103.
   PubMed Web of Science ®Google Scholar
• Halaouli S, Asther M, Sigoillot JC, et al. Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J Appl Microbiol. 2006;100(2):219–232.
   PubMed Web of Science ®Google Scholar
• Fawcett DW. The cell. Melanin pigment. Washington: W B Saunders; 1981.
   Google Scholar
• Hearing VJ, Jiménez M. Mammalian tyrosinase—the critical regulatory control point in melanocyte pigmentation. Int J Biochem. 1987;19(12):1141–1147.
   PubMedGoogle Scholar
• Chang T-S. Natural melanogenesis inhibitors acting through the down-regulation of tyrosinase activity. Materials. 2012;5(9):1661–1685.
   Web of Science ®Google Scholar
• Lee SY, Baek N, Nam T-G. Natural, semisynthetic and synthetic tyrosinase inhibitors. J Enzym Inhib Med Chem. 2016;31(1):1–13.
   PubMed Web of Science ®Google Scholar
• Parvez S, Kang M, Chung HS, et al. Survey and mechanism of skin depigmenting and lightening agents. Phytother Res. 2006;20(11):921–934.
   PubMed Web of Science ®Google Scholar
• Ando H, Kondoh H, Ichihashi M, et al. Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase. J Invest Dermatol. 2007;127(4):751–761.
   PubMed Web of Science ®Google Scholar
• Park H, Kosmadaki M, Yaar M, et al. Cellular mechanisms regulating human melanogenesis. Cell Mol Life Sci. 2009;66(9):1493–1506.
   PubMed Web of Science ®Google Scholar
• Wen H, Lin C, Que L, et al. Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors. Eur J Med Chem. 2008;43(1):166–173.
   PubMed Web of Science ®Google Scholar
• Okombi S, Rival D, Bonnet S, et al. Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase. Bioorg Med Chem Lett. 2006;16(8):2252–2255.
   PubMed Web of Science ®Google Scholar
• Busca R, Ballotti R. Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res. 2000;13(2):60–69.
   PubMedGoogle Scholar
• 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(1):205–211.
   PubMedGoogle Scholar
• Takeda K, Yasumoto K-I, Takada R, et al. Induction of melanocyte-specific microphthalmia-associated transcription factor by Wnt-3a. J Biol Chem. 2000;275(19):14013–14016.
   PubMed Web of Science ®Google Scholar
• Bellei B, Pitisci A, Izzo E, et al. Inhibition of melanogenesis by the pyridinyl imidazole class of compounds: Possible involvement of the Wnt/beta-catenin signaling pathway. PloS ONE. 2012;7(3).
   Web of Science ®Google Scholar
• Bellei B, Flori E, Izzo E, et al. GSK3β inhibition promotes melanogenesis in mouse B16 melanoma cells and normal human melanocytes. Cell Signal. 2008;20(10):1750–1761.
   PubMed Web of Science ®Google Scholar
• Kim DS, Park SH, Kwon SB, et al. Sphingosylphosphorylcholine‐induced ERK activation inhibits melanin synthesis in human melanocytes. Pigment Cell Res. 2006;19(2):146–153.
   PubMedGoogle Scholar
• Xu W, Gong L, Haddad MM, et al. Regulation of microphthalmia-associated transcription factor MITF protein levels by association with the ubiquitin-conjugating enzyme hUBC9. Exp Cell Res. 2000;255(2):135–143.
   PubMed Web of Science ®Google Scholar
• Kim D-S, Hwang E-S, Lee J-E, et al. Sphingosine-1-phosphate decreases melanin synthesis via sustained ERK activation and subsequent MITF degradation. J Cell Sci. 2003;116(9):1699–1706.
   PubMed Web of Science ®Google Scholar
• Hemesath TJ, Price ER, Takemoto C, et al. MAP kinase links the transcription factor Microphthalmia to c-Kit signalling in melanocytes. Nature. 1998;391(6664):298–301.
   PubMed Web of Science ®Google Scholar
• Wu M, Hemesath TJ, Takemoto CM, et al. c-Kit triggers dual phosphorylations, which couple activation and degradation of the essential melanocyte factor Mi. Genes Dev. 2000;14(3):301–312.
   PubMed Web of Science ®Google Scholar
• Geng J, Yu S-B, Wan X, et al. Protective action of bacterial melanin against DNA damage in full UV spectrums by a sensitive plasmid-based noncellular system. J Biochem Biophys Methods. 2008;70(6):1151–1155.
   PubMedGoogle Scholar
• Garcia-Rivera J, Casadevall A. Melanization of Cryptococcus neoformans reduces its susceptibility to the antimicrobial effects of silver nitrate. Med Mycol. 2001;39(4):353–357.
   PubMed Web of Science ®Google Scholar
• Geng J, Yuan P, Shao C, et al. Bacterial melanin interacts with double-stranded DNA with high affinity and may inhibit cell metabolism in vivo. Arch Microbiol. 2010;192(5):321–329.
   PubMed Web of Science ®Google Scholar
• Videira I, Moura DFL, Magina S. Mechanisms regulating melanogenesis. An Bras Dermatol. 2013;88(1):76–83.
   PubMed Web of Science ®Google Scholar
• Kwon HJ, Cho YS Pharmaceutical composition for preventing or treating autophagy-related diseases, angiogenic diseases or melanin-related diseases. US20130251654A1. 2013.
   Google Scholar
• Hu H, Yim S, Santhanam U, et al. Tyrosinase inhibitors. US20150164758Al. 2014.
   Google Scholar
• Torihara M, Tamai Y, Shiono M, et al. Skin depigmental agent. US4959393. 1990.
   Google Scholar
• Hu L Resorcinol derivatives. US6132740. 2000.
   Google Scholar
• Shore LJ, Rocha SA, McKinney MD. Skin lightening agents, compositions and methods. US20080131382. 2007.
   Google Scholar
• Miura Y, Kinoshita Y, Yamamoto Y, et al. Tyrosinase activity inhibitor. US5399785. 1995.
   Google Scholar
• Hinman AW, Davis D, Kheifets V Resorcinol compounds for dermatological use. US20140256830A1. 2014.
   Google Scholar
• Nandy SK, Liu J, Nesterov AM, et al. Series of skin whitening (lightening) compounds. US8362305B2. 2013.
   Google Scholar
• Nandy SK, Liu J, Nesterov AM, et al. Series of skin whitening (lightening) compounds. US20140363388A1. 2014.
   Google Scholar
• Torihara M, Tamai Y, Shiono M, et al. Skin depigmental agent. EP0341664. 1992.
   Google Scholar
• Boiteau J-G, Pascal J-C 4-(heterocycloalkyl) benzene-1, 3-diol compounds as tyrosinase inhibitors, process for the preparation thereof and use thereof in human medicine and also in cosmetics. EP2529735A1. 2013.
   Google Scholar
• Boiteau J-G, Luzy A-P 4-(azacycloalkyl)-benzene-1, 3-diol derivatives as tyrosinase inhibitors and their synthesis and use thereof. US20120323012A1. 2012.
   Google Scholar
• Chung HY, Moon HR, Park MH, et al. Novel compound having skin-whitening, anti-oxidizing and ppar activities and medical use therefor. US8889881B2. 2012.
   Google Scholar
• Chung HY, Park MH, Ha YM, et al. Compound having skin-whitening, anti-oxidizing and PPAR activities and medical use therefor. US20150017111A1. 2014.
   Google Scholar
• Boiteau JG, Barbuis CM, Bouquet K 4-heteroarylimidazole-2-thione tyrosinase inhibitors and pharmaceutical/cosmetic applications thereof. US7989483B2. 2011.
   Google Scholar
• Boiteau J-G, Barbuis CM, Talano S 4-phenylimidazole-2-thione tyrosinase inhibitors and pharmaceutical/cosmetic applications thereof. US8119674B2. 2012.
   Google Scholar
• Joo YH, Baek HS, Lee CS, et al. Novel benzoic acid amide compound. US20140234241A1. 2012.
   Google Scholar
• Okombi S, Rival D, Boumendjel A, et al., et al. Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions. US20130272983A1. 2013.
   Google Scholar
• Kaur S, Kirchner FJ, Zaleski E Topical application of 1-hydroxyl 3, 5-bis (4’hydroxyl styryl) benzene. WO2014004177A2. 2013.
   Google Scholar
• Vanni A, Gastaldi D, Giunta G. Kinetic investigations on the double enzymic activity of the tyrosinase mushroom. Annali Di Chimica. 1990;80(1–2):35–60.
   Google Scholar
• No JK, Kim YJ, Shim KH, et al. Inhibition of tyrosinase by green tea components. Life Sciences. 1999;65(21):PL241–PL46.
   PubMed Web of Science ®Google Scholar
• Chung HY, Moon HR, Park MH, et al. Novel compound having skin-whitening, anti-oxidizing and ppar activities and medical use therefor. US20140023603A1. 2014.
   Google Scholar
• Chiang H-M, Kuo Y-H, Wen K-C Method for anti-skin aging using caffeamide derivative. US20150010484A1. 2013.
   Google Scholar
• Poigny S, Belaubre F Heterocyclic resorcinol derivatives, preparation of same and cosmetic uses thereof. WO2013073763A1. 2014.
   Google Scholar
• Schlesinger MJ, Adams SP Antiviral peptides. US5026686A. 1991.
   Google Scholar
• Stewart JM, Young JD. Solid phase peptide synthesis. Rockford: Pierce Chemical Company; 1984.
   Google Scholar
• Jung DH, Moh SH, Lee JH, et al. Peptide derivatives and cosmetic composition comprising the same. US8435548B2. 2013.
   Google Scholar
• Kramer K, Lopez A, Stefanato C, et al. Exogenous ochronosis. J Am Acad Dermatol. 2000;42:869–871.
   PubMed Web of Science ®Google Scholar
• Westerhof W, Kooyers TJ. Hydroquinone and its analogues in dermatology—a potential health risk. J Cosmet Dermatol. 2005;4:55–59.
   PubMedGoogle Scholar
• Serrine SL, Terrence JM, Jeffrey IE, et al. Carcinogenicity of a nephrotoxic metabolite of the “Nongenotoxic” carcinogen hydroquinone. Chem Res Toxicol. 2001;14(1):25–33.
   PubMed Web of Science ®Google Scholar
• Vaneeta MS, Amit GP. Melasma: A comprehensive update : Part II. J Am Acad Dermatol. 2011;65(4):699–714.
   PubMed Web of Science ®Google Scholar
• Garcia A, Fulton JE Jr. The combination of glycolic acid and hydroquinone or kojic acid for the treatment of melasma and related conditions. Dermatol Surg. 1996;22:443–447.
   PubMed Web of Science ®Google Scholar
• Draelos ZD. Skin lightening preparations and the hydroqui-none controversy. Dermatol Ther. 2007;20:308–313.
   PubMed Web of Science ®Google Scholar
• Hantash BM Oligopeptide tyrosinase inhibitors and uses thereof. WO2009003034A1. 2014.
   Google Scholar
• Hantash BM Peptide tyrosinase inhibitors and uses thereof. US8026208B2. 2011.
   Google Scholar
• Hantash BM. Peptide tyrosinase inhibitors and uses thereof. WO2012154959A1. 2012.
   Google Scholar
• Hantash BM Oligopeptide tyrosinase inhibitors and uses thereof. US8193154B2. 2012.
   Google Scholar
• Collin-Djangone C, Simmonet J-T Double-stranded RNA oligonucleotides which inhibit tyrosinase expression. US8822428B2. 2014.
   Google Scholar
• Vielhaber G, Oertling H, Titze N, et al. Cyclohexyl carbamate compounds as skin and/or hair lightening actives. US20130129646A1. 2013.
   Google Scholar
• Deliencourt-Godefroy G, Lopes L Family of aryl, heteroaryl, o-aryl and o-heteroaryl carbasugars. CA2835755A1. 2012.
   Google Scholar
• Peter DW, Stanek JD, Gupta SK. Chirally correct retinal cyclodextrin hemiacetals for treating skin disorder. US8569269B1. 2013.
   Google Scholar
• Peter DW, Stanek JD, Orozco CL, et al.. Retinal cyclodextrin acetals and hemiacetals for treating skin complexion disorder. US8871748B2. 2014.
   Google Scholar
• Bajor JS, Bosko CA, Drennan DJ, et al. Skin care compositions comprising substituted monoamines. WO2012013418A3. 2012.
   Google Scholar
• Rosa JG, Harichian B, Drennan DJ, et al. Skin care compositions comprising substituted diamines. US8476251B2. 2013.
   Google Scholar
• Rosa JG, Harichian B, Bajor JS, et al. Substituted 3-(phenoxymethyl) benzyl amines and personal care compositions. US8425885B2. 2013.
   Google Scholar
• Acham NC, Unilever PLC. Novel compounds with skin lightening properties. EP2746253A1. 2014.
   Google Scholar
• Tsai WC, Chen CY, Chiu MY, et al. Compound with carboxyl acid group and amide group and application thereof. EP2295403A1. 2011.
   Google Scholar
• Scheurich RP Dihydroxyfumaric acid derivatives and the use thereof for skin lightening. US20130266526A1. 2011.
   Google Scholar
• Chen C-H, Chien M-Y, Hou W-C, et al. Method for scavenging free radicals and inhibiting tyrosinase and melanin. US20110039898A1. 2011.
   Google Scholar
• Yokoyama K, Kimura M, Tamai M, et al. Melanin production inhibitor. US8846012B2. 2014.
   Google Scholar
• Oba T, Kikuchi M, Hachiya A Tyrosinase retardant. CN103371924A. 2013.
   Google Scholar
• Oba T, Kikuchi M, Hachiya A Tyrosinase inhibitor. US20140112878A1. 2014.
   Google Scholar
• Lee M-C Skin-whitening composition containing tyrosinase inhibitor. US20120321577A1. 2012.
   Google Scholar
• Lee M-C Skin-whitening essence composition containing tyrosinase inhibitor. US20130164233A1. 2013.
   Google Scholar
• Hye RK, Hye JL, Yeon JC, 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(9):410–1417.
   Google Scholar
• Sujin S, Haewon K, Hwi YY, 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(24):7728–7734.
   PubMed Web of Science ®Google Scholar