MOLECULAR DOCKING STUDY OF A NOVEL 1,3,4-OXADIAZOLE DERIVATIVE TARGETING INSECT ACETYLCHOLINESTERASE (AChE)
Abstract
A novel 1,3,4-oxadiazole derivative, 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, was synthesized by alkylation of the corresponding 5-(4-dimethylaminophenyl)-1,3,4-oxadiazole-2-thione according to the previously developed synthetic procedure. The chemical structure of the obtained compound was confirmed using IR, 1H and 13C NMR spectroscopy. The insecticidal potential of the synthesized compound was evaluated in vitro using insect cell lines derived from Helicoverpa zea, Trichoplusia ni, and Lymantria dispar. Cell viability was determined by the MTT assay following exposure to the test compound at different concentrations. The investigated derivative demonstrated pronounced inhibitory activity against all three insect cell lines, with biological efficacy approaching that of the commercial insecticide Imidacloprid, indicating its potential as a promising lead compound for agricultural pest control. To investigate the possible molecular mechanism of action, in silico molecular docking studies were performed against insect acetylcholinesterase (AChE, PDB ID: 6XYS). Molecular docking analysis revealed that the ligand was stably accommodated within the active site of acetylcholinesterase through interactions with key amino acid residues, including Trp472, Asp482, Glu485, Ile82, Ile161, and Asp160, involving hydrogen bonding as well as р-anion, р-alkyl, and р-у interactions (fig. 1). The predicted binding pattern supports the experimentally observed insecticidal activity and suggests that inhibition of acetylcholinesterase may represent one of the principal mechanisms underlying the biological effect of this novel 1,3,4-oxadiazole derivative.
Publication Details
This article is licensed under a Creative Commons Attribution 4.0 International License.