2-acetylthiophene thiosemicarbazone as mushroom tyrosinase inhibitor: insights from kinetic, RDG, molecular docking, and DFT studies

Ahmad, Mohammad Norazmi and Jori Roslan, Muhammad Qusyairi and Abdullah, Erna Normaya (2019) 2-acetylthiophene thiosemicarbazone as mushroom tyrosinase inhibitor: insights from kinetic, RDG, molecular docking, and DFT studies. In: International Conference in Organic Synthesis 2019 (ICOS2019), 9th-10th December 2019, Avillion Admiral Cove, Port Dickson, Negeri Sembilan. (Unpublished)

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Abstract

The pressing need for better drugs against skin pigmentation motivates the search for inhibitors of tyrosinase enzyme, the main causative agent.Tyrosinase (EC 1.14.18.1), which is a copper-containing enzyme, plays a vital role in preventing skinpigmentation due to melanin biosynthesis. In this study, we have synthesized 2-acetylthiophene thiosemicarbazone (2-ATT) and determine their inhibitory study against tyrosinase enzyme. Kinetic studies revealed that, 2-ATT demonstrated a competitive inhibition with Km and Vmax value of 0.056 µM/min and 1.33 min, respectively. In the light of these study, we performed in silico study involving Reduced Density Gradient (RDG), Molecular Electrostatic Potential (MEP), molecular docking and ONIOM (QM/MM) for the 2-ATT with the tyrosinase enzyme. RDG used to find the weak non-covalent interaction (Van der Wall interaction) and strong repulsion (steric effect) of the 2-ATT. MEP and molecular docking were done to identify and investigate the key structural features of 2-ATT that are important for their activity and the interaction that contribute to tyrosinase inhibition respectively. The ONIOM calculations revealed that the binding capacity of control was (5.4 kcal/mol) higher than that of 2-ATT (5.0 kcal/mol), which could explain their difference in their inhibitory behaviour.

Item Type:	Conference or Workshop Item (Invited Papers)
Additional Information:	7148/77461
Uncontrolled Keywords:	2-acetylthiophene thiosemicarbazone (2-ATT): Reduced Density Gradient (RDG); Molecular Electrostatic Potential (MEP), Density Functional Theory (DFT)
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:	30 Dec 2019 16:06
Last Modified:	30 Dec 2019 16:06
URI:	http://irep.iium.edu.my/id/eprint/77461

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