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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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) |
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eugenol derivatives amino alcohols semisynthetic insecticides biopesticides bioinsecticides phenylpropanoids Organic chemistry QD241-441 |
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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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