Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights

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 <i>Sf9</i>...

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Autores principales: Renato B. Pereira, Nuno F. S. Pinto, Maria José G. Fernandes, Tatiana F. Vieira, Ana Rita O. Rodrigues, David M. Pereira, Sérgio F. Sousa, Elisabete M. S. Castanheira, A. Gil Fortes, M. Sameiro T. Gonçalves
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Publicado: MDPI AG 2021
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spelling oai:doaj.org-article:5d61ad86226742e4aeb744f3dd9358c22021-11-11T18:35:18ZAmino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights10.3390/molecules262166161420-3049https://doaj.org/article/5d61ad86226742e4aeb744f3dd9358c22021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6616https://doaj.org/toc/1420-3049A 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 <i>Sf9</i> 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.Renato B. PereiraNuno F. S. PintoMaria José G. FernandesTatiana F. VieiraAna Rita O. RodriguesDavid M. PereiraSérgio F. SousaElisabete M. S. CastanheiraA. Gil FortesM. Sameiro T. GonçalvesMDPI AGarticleeugenol derivativesamino alcoholssemisynthetic insecticidesbiopesticidesbioinsecticidesphenylpropanoidsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6616, p 6616 (2021)
institution DOAJ
collection DOAJ
language EN
topic eugenol derivatives
amino alcohols
semisynthetic insecticides
biopesticides
bioinsecticides
phenylpropanoids
Organic chemistry
QD241-441
spellingShingle eugenol derivatives
amino alcohols
semisynthetic insecticides
biopesticides
bioinsecticides
phenylpropanoids
Organic chemistry
QD241-441
Renato B. Pereira
Nuno F. S. Pinto
Maria José G. Fernandes
Tatiana F. Vieira
Ana Rita O. Rodrigues
David M. Pereira
Sérgio F. Sousa
Elisabete M. S. Castanheira
A. Gil Fortes
M. Sameiro T. Gonçalves
Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights
description 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 <i>Sf9</i> 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.
format article
author Renato B. Pereira
Nuno F. S. Pinto
Maria José G. Fernandes
Tatiana F. Vieira
Ana Rita O. Rodrigues
David M. Pereira
Sérgio F. Sousa
Elisabete M. S. Castanheira
A. Gil Fortes
M. Sameiro T. Gonçalves
author_facet Renato B. Pereira
Nuno F. S. Pinto
Maria José G. Fernandes
Tatiana F. Vieira
Ana Rita O. Rodrigues
David M. Pereira
Sérgio F. Sousa
Elisabete M. S. Castanheira
A. Gil Fortes
M. Sameiro T. Gonçalves
author_sort Renato B. Pereira
title Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights
title_short Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights
title_full Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights
title_fullStr Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights
title_full_unstemmed Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights
title_sort amino alcohols from eugenol as potential semisynthetic insecticides: chemical, biological, and computational insights
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/5d61ad86226742e4aeb744f3dd9358c2
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