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Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors. 2020

Morteza Ashooriha, and Mehdi Khoshneviszadeh, and Mahsima Khoshneviszadeh, and Alireza Rafiei, and Mostafa Kardan, and Rezvan Yazdian-Robati, and Saeed Emami
Department of Medicinal Chemistry, Student Research Committee, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.

As part of our effort to develop potential tyrosinase inhibitors, we have conjugated the well-known tyrosinase inhibitor kojic acid (KA) with several phenolic natural products such as umbelliferone, sesamol, thymol, carvacrol, eugenol, isoeugenol, vanillin, isovanillin, and apocynin that some reports have shown their activity on tyrosinase enzyme. The designed compounds were synthesized using click reaction and 1,2,3-triazole formation. All compound showed potent anti-tyrosinase activity significantly higher than KA. The best activities were observed with apocynin and 4-coumarinol analogs (10c and 16c) displaying IC50 values of 0.03 and 0.02 μM, respectively. The potency of 16c was >460-times more than that of KA. Cell-based assays against B16F10 and HFF cells revealed that the representative compounds can efficiently suppress the melanogenesis without significant toxicity on cells.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008543 Melanins Insoluble polymers of TYROSINE derivatives found in and causing darkness in skin (SKIN PIGMENTATION), hair, and feathers providing protection against SUNBURN induced by SUNLIGHT. CAROTENES contribute yellow and red coloration. Allomelanins,Melanin,Phaeomelanins
D011485 Protein Binding The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments. Plasma Protein Binding Capacity,Binding, Protein
D011753 Pyrones Keto-pyrans.
D003300 Copper A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55. Copper-63,Copper 63
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000363 Agaricales An extensive order of basidiomycetous fungi whose fruiting bodies are commonly called mushrooms. Agaricaceae,Mushrooms,Agaricale,Mushroom
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001688 Biological Products Complex pharmaceutical substances, preparations, or matter derived from organisms usually obtained by biological methods or assay. Biologic,Biologic Drug,Biologic Product,Biological,Biological Drug,Biological Medicine,Biological Product,Biologics,Biopharmaceutical,Natural Product,Natural Products,Biologic Drugs,Biologic Medicines,Biologic Pharmaceuticals,Biologic Products,Biological Drugs,Biological Medicines,Biologicals,Biopharmaceuticals,Products, Biological,Drug, Biologic,Drug, Biological,Drugs, Biologic,Drugs, Biological,Medicine, Biological,Medicines, Biologic,Medicines, Biological,Pharmaceuticals, Biologic,Product, Biologic,Product, Biological,Product, Natural

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