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Anti-Melanogenesis and Anti-Tyrosinase Properties of Aryl-Substituted Acetamides of Phenoxy Methyl Triazole Conjugated With Thiosemicarbazide: Design, Synthesis and Biological Evaluations Publisher Pubmed



Hosseinpoor H1 ; Moghadam Farid S2 ; Iraji A3, 4 ; Askari S5 ; Edraki N3 ; Hosseini S7 ; Jamshidzadeh A6 ; Larijani B2 ; Attarroshan M3 ; Pirhadi S3 ; Mahdavi M2 ; Khoshneviszadeh M1, 3
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, 71345, Iran
  2. 2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, 71348, Iran
  4. 4. Central Research laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
  5. 5. Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran, Iran
  6. 6. Department of Pharmacology and Toxicology, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
  7. 7. Phytochemistry Research Center, Shahid Beheshti University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2021


Abstract

A series of aryl phenoxy methyl triazole conjugated with thiosemicarbazides were designed, synthesized, and evaluated for their tyrosinase inhibitory activities in the presence of L-dopa and L-tyrosine as substrates. All the compounds showed tyrosinase inhibition in the sub-micromolar concentration. Among the derivatives, compound 9j bearing benzyl displayed exceptionally high potency against tyrosinase with IC50 value of 0.11 μM and 0.17 μM in the presence of L-tyrosine and L-dopa as substrates which is significantly lower than that of kojic acid as the positive control with an IC50 value of 9.28 μM for L-tyrosine and 9.30 μM for L-dopa. According to Lineweaver–Burk plot, 9j demonstrated an uncompetitive type of inhibition in the kinetic assay. Also, in vitro antioxidant activities determined by DPPH assay recorded an IC50 value of 68.43 μM for 9i. The melanin content of 9j was determined on B16F10 melanoma human cells which demonstrated a significant reduction of the melanin content. Moreover, the binding energies corresponding to the same ligand as well as computer-aided drug-likeness and pharmacokinetic studies were also carried out. Compound 9j also possessed metal chelation potential correlated to its high anti-TYR activity. © 2021 Elsevier Inc.
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