Author(s): Fernandes, Maria José Gomes ; Pereira, Renato B. ; Rodrigues, Ana Rita Oliveira ; Vieira, Tatiana F. ; Fortes, A. Gil ; Pereira, David M. ; Sousa, Sérgio F. ; Gonçalves, M. Sameiro T. ; Castanheira, Elisabete M. S.
Date: 2022
Persistent ID: https://hdl.handle.net/1822/80251
Origin: RepositóriUM - Universidade do Minho
Subject(s): eugenol derivatives; nanoencapsulation; liposomal formulations; inverted virtual screening; protein targets; insecticides
A recently synthesized new eugenol derivative, ethyl 4-(2-methoxy-4-(oxiran-2-ylmethyl)phenoxy)butanoate, with a high insecticidal activity against Sf9 (Spodoptera frugiperda) insect cells, was encapsulated in the liposomal formulations of egg-phosphatidylcholine/cholesterol (Egg-PC:Ch) 70:30 and 100% dioleoylphosphatidylglycerol (DOPG), aiming at the future application as insecticides. Compound-loaded DOPG liposomes have sizes of 274 ± 12 nm, while Egg-PC:Ch liposomes exhibit smaller hydrodynamic diameters (69.5 ± 7 nm), high encapsulation efficiency (88.8% ± 2.7%), higher stability, and a more efficient compound release, thus, they were chosen for assays in Sf9 insect cells. The compound elicited a loss of cell viability up to 80% after 72 h of incubation. Relevantly, nanoencapsulation maintained the toxicity of the compound toward insect cells while lowering the toxicity toward human cells, thus showing the selectivity of the system. Structure-based inverted virtual screening was used to predict the most likely targets and molecular dynamics simulations and free energy calculations were used to demonstrate that this molecule can form a stable complex with insect odorant binding proteins and/or acetylcholinesterase. The results are promising for the future application of compound-loaded nanoliposome formulations as crop insecticides.
