Antibacterial Potential of Trihydroxycyclohexa-2,4-Diene-1- Carboxylic Acid: Insight from DFT, Molecular Docking, and Molecular Dynamic Simulation

Owen, Aniekan E. and Ahmad, Iqrar and Emori, Wilfred and Agwamba, Ernest C. and Cheng, Chun-Ru and Benjamin, Innocent and Patel, Harun and Ahuekwe, Eze Frank and Ojong, Mmefone A. and Ubah, Chioma B. and Manicum, Amanda-Lee E. and Louis, Hitler (2024) Antibacterial Potential of Trihydroxycyclohexa-2,4-Diene-1- Carboxylic Acid: Insight from DFT, Molecular Docking, and Molecular Dynamic Simulation. Polycyclic Aromatic Compounds, 44 (3). pp. 2128-2151.

PDF Download (256kB)

Abstract

In this study, (z)-5-((3-(2,3-dihydroxyphenyl) acryloyl) oxy)- 1,3,4-trihydroxycyclohexa- 2,4-diene-1-carboxylic acid (chlorogenic acid) was isolated and characterized using UVVisible, 1H NMR and 13C NMR, FT-IR, along with detailed investigation using density functional theory (DFT), in-silico molecular docking, and molecular dynamics (MD) simulation. Results from DFT calculation indicates that the titled compound is very stable with energy gap of 3.7–7.8 for variable functionals, and similarly, the structural parameters show very close agreement with X-ray data for bond lengths and angles. The FT-IR spectrum results revealed stretching vibration O–H (3366 cm−1), C=O (1689 cm−1), C–H (1636, 1606, 1522, and 1442 cm−1), C–O (1192 and 1122 cm−1). The drug-likeness analyses and ADME studies showed drug-likeness ability and good oral behavior of the investigated compound as it obeys Lipinski, Ghose, Veber and Egan rules. Hepatotoxic and immunotoxic activities were indicated for the toxicity/toxicological endpoints of the studied compound. The molecular docking indicates a binding affinity of −8.30 and 9.5 kcal/mol for the titled compound, which is higher than the standard drug. From the molecular dynamic simulation results, chlorogenic-2H14 (complex B) revealed variations in RMSD values of less than 3Å, indicating that the protein structure underwent minor conformational changes throughout the simulation. Chlorogenicprotein complexes had average RGyr values of 3.704 − 4.907Å, which indicates compaction during the simulation. Therefore, it can be said that the titled compound has potential to be effective as an agent for cholera management, and the results obtained can be platform further in-vitro, vivo and clinical trials.

Item Type:	Article
Uncontrolled Keywords:	DFT  ADMET  molecular docking  molecular dynamic simulation
Subjects:	Q Science > QH Natural history Q Science > QH Natural history > QH301 Biology Q Science > QR Microbiology
Divisions:	Faculty of Medicine, Health and Life Sciences > School of Biological Sciences
Depositing User:	ORIGBOEYEGHA
Date Deposited:	15 Jul 2024 13:55
Last Modified:	15 Jul 2024 13:55
URI:	http://eprints.covenantuniversity.edu.ng/id/eprint/18202

Actions (login required)

View Item