Please check our research article published in Molecules (IF 4.412), a collaborative effort of BioSIM with the Faculty of Pharmacy of the University of Porto, and with the Centers of Physics and Chemistry of the University of Minho.
Amino alcohols from eugenol as potential semisynthetic insecticides: Chemical, biological, and computational insights
Pereira R.B., Pinto N.F.S., Fernandes M.J.G., Vieira T.F., Rodrigues A.R.O., Pereira D.M., Sousa S.F., Castanheira E.M.S., Gil Fortes A., and Goncalves M.S.T.
Molecules 26 (21) (2021)
A series of β-amino alcohols were prepared by the reaction of eugenol epoxide with aliphatic and aromatic amine nucleophiles. The synthesized compounds were fully characterized and evaluated as potential insecticides through the assessment of their biological activity against Sf9 insect cells, compared with a commercial synthetic pesticide (chlorpyrifos, CHPY). Three derivatives bearing a terminal benzene ring, either substituted or unsubstituted, were identified as the most potent molecules, two of them displaying higher toxicity to insect cells than CHPY. In addition, the most promising molecules were able to increase the activity of serine proteases (caspases) pivotal to apoptosis and were more toxic to insect cells than human cells. Structure-based inverted virtual screening and molecular dynamics simulations demonstrate that these molecules likely target acetylcholinesterase and/or the insect odorant-binding proteins and are able to form stable complexes with these proteins. Encapsulation assays in liposomes of DMPG and DPPC/DMPG (1:1) were performed for the most active compound, and high encapsulation efficiencies were obtained. A thermosensitive formulation was achieved with the compound release being more efficient at higher temperatures.