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Anti-Cholinesterase Activity of Chalcone Derivatives: Synthesis, In Vitro Assay and Molecular Docking Study

Author(s):

Florentinus D.O. Riswanto, Mira S.A. Rawa, Vikneswaran Murugaiyah, Nurul H. Salin, Enade P. Istyastono, Maywan Hariono and Habibah A. Wahab*   Pages 1 - 11 ( 11 )

Abstract:


Background: Chalcones, originated from natural product, have been broadly studied their biological activity against various proteins which at the molecular level, are responsible for the progress of the diseases in cancer (e.g. kinases), inflammation (oxidoreductases), atherosclerosis (cathepsins receptor), and diabetes (e.g. α-glucosidase).

Objective: Here we synthesize 10 chalcone derivatives to be evaluated their in vitro enzymatic inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).

Method: The synthesis was carried out using Claissen-Schimdt condensation and the in vitro assay was conducted using Ellman Method. Results: Compounds 2b and 4b demonstrated the best IC50 of 9.3 µM and 68.7 µM respectively, towards AChE and BChE inhibition. Molecular docking studies predicted that this activity might be due to the interaction of the chalcones with important amino acid residues in the binding site of AChE such as SER200 and in that of BChE such as TRP82, SER198, TRP430, TYR440, LEU286 and VAL288.

Conclusion: Chalcone can be used as the scaffold for cholinesterase inhibitor, in particularly either fluorine or nitro group to be augmented at the para-position of Ring B, whereas the hydrophobic chain is necessary at the meta-position of Ring B.

Keywords:

Acetylcholinesterase, Butyrylcholinesterase, Chalcone, Docking, In Vitro Assay

Affiliation:

Department of Pharmaceutical Analysis and Medicinal Chemistry, Faculty of Pharmacy, Sanata Dharma University, Yogyakarta, Department of Pharmaceutical Technology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Pulau Pinang, Department of Pharmaceutical Technology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Pulau Pinang, Malaysian Institute of Pharmaceuticals and Nutraceuticals, National Institute of Biotechnology Malaysia, Pulau Pinang, Department of Pharmaceutical Analysis and Medicinal Chemistry, Faculty of Pharmacy, Sanata Dharma University, Yogyakarta, Department of Pharmaceutical Analysis and Medicinal Chemistry, Faculty of Pharmacy, Sanata Dharma University, Yogyakarta, Department of Pharmaceutical Technology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Pulau Pinang



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