(1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies

Shamsuri, Syamimi Sulfiza and Abdullah, Erna Normaya and Ismail, Hakimah and Iqbal, Anwar and Mat Piah, Mohd Bijarimi and Abdul Aziz, Yang Farina and Hamzah, Ahmad Sazali and Ahmad, Mohammad Norazmi (2023) (1E)-1-(2-pyrazinyl)ethanone thiosemicarbazone (PT) as a tyrosinase inhibitor with anti-browning activity: Spectroscopy, DFT and molecular docking studies. Journal of Molecular Structure, 1291. ISSN 0022-2860

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Abstract

In this study, (1E)-1-(2-Pyrazinyl)ethanone thiosemicarbazone (PT) was synthesized and characterized using Fourier-transform infrared (FTIR), ultraviolet-visible (UV–Vis), proton nuclear magnetic resonance (1HNMR ) and carbon-13 nuclear magnetic resonance (13CNMR ) spectroscopy. The vibrational frequencies were analysed using the Vibrational Energy Distribution Analysis (VEDA) program. The chemical properties of PT, including electron density distribution and intramolecular interactions, were characterized using in-silico methods based on Mulliken atomic charges, molecular electrostatic potential (MEP), quantum theory of atoms in molecules and reduced density gradient noncovalent interaction approaches. PT exhibits a significant inhibitory effect on enzymatic browning (6 and 24 h) and tyrosinase enzymes (IC50 = 7.75 μM). Kinetic analysis shows that PT is a mixed-type inhibitor, with respective Km and Vmax values of 0.632 mM and 0.0044 μM/s, and that it forms a reversible enzyme-inhibitor interaction. The PT-tyrosinase interaction was experimentally evaluated based on 1D, second derivatives of 1D, 2D and 3D IR spectroscopy. Furthermore, analysis of absorption, distribution, metabolism, excretions and toxicity properties revealed good physicochemical properties of PT according to the drug scores and Lipinski’s Rule of Five. Lastly, the mechanisms of PT against tyrosinase were visualized and supported by means of a molecular docking approach.

Item Type:	Article (Journal)
Uncontrolled Keywords:	Tyrosinase inhibitors; Enzymatic browning' 2D-IR; QTAIM; DFT; ADMETOX
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science Kulliyyah of Science > Department of Chemistry
Depositing User:	Dr Mohammad Norazmi Ahmad
Date Deposited:	18 Jul 2023 10:21
Last Modified:	18 Jul 2023 10:21
URI:	http://irep.iium.edu.my/id/eprint/105415

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