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Synthesis, Biological Evaluation, and Molecular Docking Analysis of Novel 1, 3, 4-Thiadiazole -Based Kojic Acid Derivatives As Tyrosinase Inhibitors Publisher



Talebi M1 ; Majidi K1 ; Bassam K1 ; Abdi M1 ; Daneshvar M2 ; Moayedi SS2 ; Pourhesabi S1 ; Attarroshan M3 ; Boumi S1 ; Kabiri M2 ; Hosseini FS1 ; Khoshneviszadeh M2, 3 ; Amanlou M1, 4
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
  3. 3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Experimental Medicine Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Molecular Structure Published:2022


Abstract

Kojic acid is a natural tyrosinase inhibitor that has been clinically used to cure hyperpigmentation in humans. However, kojic acid as a hydrophilic small-molecule has deficient inhibitory activity and stability. In this current work, a new series of kojic acid derivatives, 4a–h bearing 2-amino-5-mercapto-1,3,4-thiadiazole, were synthesized using TBTU as the catalyst, and their chemical structures were characterized by spectroscopic methods. The inhibitory activities of synthesized compounds against Mushroom tyrosinase were evaluated in vitro, and some derivatives showed potent anti-tyrosinase activity. In particular, compounds 4g (IC50=10.71 ± 2.47 µM) and 4h (IC50=18.62 ± 3.05 µM) were comparable with the reference compound, kojic acid (IC50=23.14 µM). The Docking study was in good agreement with experimental results and indicated that compound 4g interacted entirely with the active site of tyrosinase with proper binding energy and mode. © 2022
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