Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Encapsulation Studies and In Silico Identification of Protein Targets Associated to the Insecticide Activity of Eugenol Derivatives

Version 1 : Received: 3 August 2022 / Approved: 5 August 2022 / Online: 5 August 2022 (14:43:22 CEST)

How to cite: Fernandes, M.J.G.; Pereira, R.B.; Rodrigues, A.R.O.; Vieira, T.F.; Fortes, A.G.; Pereira, D.M.; Sousa, S.F.; Castanheira, E.M.S.; Gonçalves, M.S. Encapsulation Studies and In Silico Identification of Protein Targets Associated to the Insecticide Activity of Eugenol Derivatives. Preprints 2022, 2022080126 (doi: 10.20944/preprints202208.0126.v1). Fernandes, M.J.G.; Pereira, R.B.; Rodrigues, A.R.O.; Vieira, T.F.; Fortes, A.G.; Pereira, D.M.; Sousa, S.F.; Castanheira, E.M.S.; Gonçalves, M.S. Encapsulation Studies and In Silico Identification of Protein Targets Associated to the Insecticide Activity of Eugenol Derivatives. Preprints 2022, 2022080126 (doi: 10.20944/preprints202208.0126.v1).

Abstract

The eugenol derivative, ethyl 4-(2-methoxy-4-(oxiran-2-ylmethyl)phenoxy)butanoate 1, with promising insecticidal capability was encapsulated in liposomal formulations of egg-phosphatidylcholine/cholesterol (Egg-PC:Ch) 70:30 and of 100% dioleoylphosphatidylglycerol (DOPG). Compound-loaded Egg-PC:Ch liposomes exhibit small hydrodynamic diameters (below 100 nm), high encapsulation efficiency (88.8% ± 2.7%), higher stability and a more efficient compound release, being chosen for assays in Sf9 insect cells. Compound 1 elicited a loss of cell viability up to 80% after 72h of incubation. Relevantly, encapsulation maintained the toxicity of compound 1 towards insect cells, while it lowered toxicity towards 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.

Keywords

Eugenol; Essential oils; Nanoencapsulation; Biopesticides; Insecticides; Odorant binding proteins; Inverted virtual screening

Subject

CHEMISTRY, Applied Chemistry

Comments (0)

We encourage comments and feedback from a broad range of readers. See criteria for comments and our diversity statement.

Leave a public comment
Send a private comment to the author(s)
Views 0
Downloads 0
Comments 0
Metrics 0


×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.

We use cookies on our website to ensure you get the best experience.
Read more about our cookies here.