Exploring the structural, photophysical and optoelectronic properties of a diaryl heptanoid curcumin derivative and identification as a SARS-CoV-2 inhibitor

Vikaraman P Archana; Sanja J Armaković; Stevan Armaković; Ismail Celik; J B Bhagyasree; K V Dinesh Babu; Mithun Rudrapal; Indira S Divya; Renjith Raveendran Pillai

doi:10.1016/j.molstruc.2023.135110

Exploring the structural, photophysical and optoelectronic properties of a diaryl heptanoid curcumin derivative and identification as a SARS-CoV-2 inhibitor

J Mol Struct. 2023 Jun 5:1281:135110. doi: 10.1016/j.molstruc.2023.135110. Epub 2023 Feb 9.

Authors

Vikaraman P Archana^{1

2}, Sanja J Armaković^{3

4}, Stevan Armaković^{5

4}, Ismail Celik⁶, J B Bhagyasree¹, K V Dinesh Babu², Mithun Rudrapal⁷, Indira S Divya⁸, Renjith Raveendran Pillai^{9

4}

Affiliations

¹ Department of Polymer Chemistry, Government College, Attingal, University of Kerala, Thiruvananthapuram, Kerala, India.
² Department of Chemistry, Government College for Women, University of Kerala, Vazhuthacaud, Thiruvananthapuram, Kerala, India.
³ University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg D. Obradovića 3, 21000 Novi Sad, Serbia.
⁴ Association for the International Development of Academic and Scientific Collaboration (AIDASCO), Novi Sad, Serbia.
⁵ University of Novi Sad, Faculty of Sciences, Department of Physics, Trg D. Obradovića 4, 21000 Novi Sad, Serbia.
⁶ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, Kayseri 38280, Turkey.
⁷ Department of Pharmaceutical Sciences, School of Biotechnology & Pharmaceutical Sciences, Vignan's Foundation for Science, Technology and Research (Deemed to be University), Vadlamudi, Guntur-522213, India.
⁸ Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, India.
⁹ Department of Physics, University College, University of Kerala, Thiruvananthapuram, Kerala, India.

Abstract

Developing modifiable natural products those having antiviral activities against SARS-CoV-2 is a key research area which is popular in current scenario of COVID pandemic. A diaryl heptanoid curcumin and its derivatives are already presenting promising candidates for anti-viral drug development. We have synthesized single crystals of a dimethylamino derivative of natural curcumin and structural characterization was done by single crystal XRD analysis. Using steady-state absorption and emission spectra and guided by complimentary ab initio calculations, we unraveled the solvent effects on the photophysical properties of the dimethyl amino curcumin derivative. Chemical reactivity of the compound has investigated using frontier molecular orbitals and molecular electrostatic potential surface. High stability of the curcumin derivative in water environment has evaluated by Radial Distributions Functions (RDF) calculated via Molecular Dynamics (MD) simulations. The inhibitory activity of the title compound was evaluated by in silico methods and the stability of the protein-ligand complexes were studied using Molecular Dynamics simulations and MM-PBSA analysis. With this detailed study, we hope to motivate scientific community to develop new curcumin derivatives against SARS-CoV-2 virus.

Keywords: Curcumin; DFT; Molecular Docking; Molecular dynamics; UV–visible; XRD.