Antioxidant and anti-inflammatory potentials of 2-(acetoxymethyl)-3-(methoxycarbonyl) biphenylene: Insights from in vitro and molecular docking studies

Abstract

The quest for natural therapies is in continuum due to the need for medications with better efficacy and safety. This study investigated the antioxidant and anti-inflammatory potentials of 2-(acetoxymethyl)-3-(methoxycarbonyl) biphenylene (AC) using in vitro biochemical and molecular docking analyses. From the results, 2,2-Diphenyl-1-picrylhydrazyl and nitric oxide radicals were scavenged by half at AC concentrations of 13.28 and 2.37 mg/mL, respectively, while AC expressed moderate ferric reducing antioxidant power and total antioxidant capacity at effective concentrations of 1.46 and 0.38 mg/mL relative to ascorbic acid, a standard antioxidant. Similarly, AC and diclofenac inhibited heat-induced albumin denaturation by 50% at concentrations of 0.75 and 0.17 mg/mL, respectively. Molecular docking revealed that cyclooxygenase-2 (COX-2) exhibited moderate binding affinity for AC (-6.8 Kcal/mol) relative to the standard anti-inflammatory drug (-7.9 Kcal/mol). Visualization of the output ligands showed that the enzyme’s interaction with arachidonic acid (the substrate) involved amino acid residues, most of which also participated in binding with diclofenac. In contrast, the interaction between COX-2 and AC involved predominantly non-catalytic amino acid residues and was driven by van der Waals forces, π-donor hydrogen bonds, alkyl, and π-alkyl hydrophobic interactions. Thus, findings from this research reveal AC’s potential as a viable novel antioxidant and anti-inflammatory agent.