{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,28]],"date-time":"2026-10-28T04:25:06Z","timestamp":1793161506911,"version":"4.5.0"},"reference-count":79,"publisher":"Public Library of Science (PLoS)","issue":"11","license":[{"start":{"date-parts":[[2022,11,9]],"date-time":"2022-11-09T00:00:00Z","timestamp":1667952000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001321","name":"National Research Foundation","doi-asserted-by":"publisher","award":["64763"],"award-info":[{"award-number":["64763"]}],"id":[{"id":"10.13039\/501100001321","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001322","name":"South African Medical Research Council","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["www.plosone.org"],"crossmark-restriction":false},"short-container-title":["PLoS ONE"],"abstract":"<jats:p>Current studies on<jats:italic>Anopheles<\/jats:italic>anticholinesterase insecticides are focusing on identifying agents with high selectivity towards<jats:italic>Anopheles<\/jats:italic>over mammalian targets. Acetylcholinesterase (AChE) from electric eel is often used as the bioequivalent enzyme to study ligands designed for activity and inhibition in human. In this study, previously identified derivatives of a potent AChE, donepezil, that have exhibited low activity on electric eel AChE were assessed for potential AChE-based larvicidal effects on four African malaria vectors;<jats:italic>An<\/jats:italic>.<jats:italic>funestus<\/jats:italic>,<jats:italic>An<\/jats:italic>.<jats:italic>arabiensis<\/jats:italic>,<jats:italic>An<\/jats:italic>.<jats:italic>gambiae<\/jats:italic>and<jats:italic>An<\/jats:italic>.<jats:italic>coluzzii<\/jats:italic>. This led to the identification of four larvicidal agents with a lead molecule, 1-benzyl-<jats:italic>N<\/jats:italic>-(thiazol-2-yl) piperidine-4-carboxamide<jats:bold>2<\/jats:bold>showing selectivity for<jats:italic>An<\/jats:italic>.<jats:italic>arabiensis<\/jats:italic>as a larvicidal AChE agent. Differential activities of this molecule on<jats:italic>An<\/jats:italic>.<jats:italic>arabiensis<\/jats:italic>and electric eel AChE targets were studied through molecular modelling. Homology modelling was used to generate a three-dimensional structure of the<jats:italic>An<\/jats:italic>.<jats:italic>arabiensis<\/jats:italic>AChE for this binding assay. The conformation of this molecule and corresponding interactions with the AChE catalytic site was markedly different between the two targets. Assessment of the differences between the AChE binding sites from electric eel, human and<jats:italic>Anopheles<\/jats:italic>revealed that the electric eel and human AChE proteins were very similar. In contrast,<jats:italic>Anopheles<\/jats:italic>AChE had a smaller cysteine residue in place of bulky phenylalanine group at the entrance to the catalytic site, and a smaller aspartic acid residue at the base of the active site gorge, in place of the bulky tyrosine residues. Results from this study suggest that this difference affects the ligand orientation and corresponding interactions at the catalytic site. The lead molecule<jats:bold>2<\/jats:bold>also formed more favourable interactions with<jats:italic>An<\/jats:italic>.<jats:italic>arabiensis<\/jats:italic>AChE model than other<jats:italic>Anopheles<\/jats:italic>AChE targets, possibly explaining the observed selectivity among other assessed<jats:italic>Anopheles<\/jats:italic>species. This study suggests that 1-benzyl-<jats:italic>N<\/jats:italic>-(thiazol-2-yl) piperidine-4-carboxamide<jats:bold>2<\/jats:bold>may be a lead compound for designing novel insecticides against<jats:italic>Anopheles<\/jats:italic>vectors with reduced toxic potential on humans.<\/jats:p>","DOI":"10.1371\/journal.pone.0277363","type":"journal-article","created":{"date-parts":[[2022,11,9]],"date-time":"2022-11-09T18:59:47Z","timestamp":1668020387000},"page":"e0277363","update-policy":"https:\/\/doi.org\/10.1371\/journal.pone.corrections_policy","source":"Crossref","is-referenced-by-count":10,"title":["The in silico and in vitro analysis of donepezil derivatives for Anopheles acetylcholinesterase inhibition"],"prefix":"10.1371","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8585-0888","authenticated-orcid":true,"given":"Thankhoe A.","family":"Rants\u2019o","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4551-6014","authenticated-orcid":true,"given":"Divan G.","family":"van Greunen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"C. 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