1. Academic Validation
  2. Thiazolopyrimidine derivatives as novel class of small molecule tyrosinase inhibitor

Thiazolopyrimidine derivatives as novel class of small molecule tyrosinase inhibitor

  • BMC Chem. 2023 Nov 19;17(1):156. doi: 10.1186/s13065-023-01077-z.
Nastaran Ghasemi 1 Shahram Moradi 1 Aida Iraji 2 3 Mohammad Mahdavi 4
Affiliations

Affiliations

  • 1 Faculty of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran.
  • 2 Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran. iraji@sums.ac.ir.
  • 3 Research Center for Traditional Medicine and History of Medicine, Department of Persian Medicine, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran. iraji@sums.ac.ir.
  • 4 Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran. momahdavi@sina.tums.ac.ir.
Abstract

Tyrosinase, the rate-limiting Enzyme of melanogenesis, plays a crucial role in hyperpigmentation. As a result, in this study, a novel class of thiazolopyrimidine derivatives was developed and synthesized as Tyrosinase Inhibitor. The structure of derivatives was characterized using various spectroscopy techniques, including FTIR, Mass, 1H-NMR, and 13C-NMR. Next, the inhibitory activities of all derivatives were examined against Tyrosinase, and, 6a as the most potent compound, exhibited an IC50 value of 28.50 µM. Furthermore, the kinetic study of 6a was performed to better understand the inhibitory mechanism and its type of inhibition. The UV/Vis spectra analysis was also executed to provide valuable evidence supporting the inhibitory mechanism of compound 6a in the context of Tyrosinase inhibition. Also, molecular docking and dynamic molecular study of 6a were executed to study its interactions within the enzyme's binding site.

Keywords

Molecular dynamic simulation; Synthesis; Thiazolopyrimidine; Tyrosinase.

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