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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MDPI AG
2021-10-01
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| Online Access: | https://www.mdpi.com/1420-3049/26/21/6616 |
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| 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 |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T05:55:50Z |
| format | Article |
| id | doaj.art-5d61ad86226742e4aeb744f3dd9358c2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:55:50Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5d61ad86226742e4aeb744f3dd9358c22023-11-22T21:23:58ZengMDPI AGMolecules1420-30492021-10-012621661610.3390/molecules26216616Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational InsightsRenato B. Pereira0Nuno F. S. Pinto1Maria José G. Fernandes2Tatiana F. Vieira3Ana Rita O. Rodrigues4David M. Pereira5Sérgio F. Sousa6Elisabete M. S. Castanheira7A. Gil Fortes8M. Sameiro T. Gonçalves9REQUIMTE/LAQV, Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, R. Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalCentre of Chemistry, Department of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, PortugalCentre of Chemistry, Department of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, PortugalAssociate Laboratory i4HB—Institute for Health and Bioeconomy, Faculty of Medicine, University of Porto, 4200-319 Porto, PortugalCentre of Physics of Minho and Porto Universities (CF-UM-UP), University of Minho, Campus of Gualtar, 4710-057 Braga, PortugalREQUIMTE/LAQV, Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, R. Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalAssociate Laboratory i4HB—Institute for Health and Bioeconomy, Faculty of Medicine, University of Porto, 4200-319 Porto, PortugalCentre of Physics of Minho and Porto Universities (CF-UM-UP), University of Minho, Campus of Gualtar, 4710-057 Braga, PortugalCentre of Chemistry, Department of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, PortugalCentre of Chemistry, Department of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, PortugalA 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.https://www.mdpi.com/1420-3049/26/21/6616eugenol derivativesamino alcoholssemisynthetic insecticidesbiopesticidesbioinsecticidesphenylpropanoids |
| spellingShingle | 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 Molecules eugenol derivatives amino alcohols semisynthetic insecticides biopesticides bioinsecticides phenylpropanoids |
| title | 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_short | 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 |
| topic | eugenol derivatives amino alcohols semisynthetic insecticides biopesticides bioinsecticides phenylpropanoids |
| url | https://www.mdpi.com/1420-3049/26/21/6616 |
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