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 Sf9 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.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2021 |
|---|---|
| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
|---|---|
| Enthalten in: |
Molecules (Basel, Switzerland) - 26(2021), 21 vom: 31. Okt. |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Pereira, Renato B [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
3T8H1794QW |
|---|
| Anmerkungen: |
Date Completed 03.12.2021 Date Revised 14.12.2021 published: Electronic Citation Status MEDLINE |
|---|
| doi: |
10.3390/molecules26216616 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM333088484 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM333088484 | ||
| 003 | DE-627 | ||
| 005 | 20231225220923.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231225s2021 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.3390/molecules26216616 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1110.xml |
| 035 | |a (DE-627)NLM333088484 | ||
| 035 | |a (NLM)34771025 | ||
| 035 | |a (PII)6616 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Pereira, Renato B |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides |b Chemical, Biological, and Computational Insights |
| 264 | 1 | |c 2021 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 03.12.2021 | ||
| 500 | |a Date Revised 14.12.2021 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a 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 Sf9 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Spodoptera frugiperda | |
| 650 | 4 | |a amino alcohols | |
| 650 | 4 | |a bioinsecticides | |
| 650 | 4 | |a biopesticides | |
| 650 | 4 | |a eugenol derivatives | |
| 650 | 4 | |a phenylpropanoids | |
| 650 | 4 | |a semisynthetic insecticides | |
| 650 | 7 | |a Amino Alcohols |2 NLM | |
| 650 | 7 | |a Insecticides |2 NLM | |
| 650 | 7 | |a Eugenol |2 NLM | |
| 650 | 7 | |a 3T8H1794QW |2 NLM | |
| 700 | 1 | |a Pinto, Nuno F S |e verfasserin |4 aut | |
| 700 | 1 | |a Fernandes, Maria José G |e verfasserin |4 aut | |
| 700 | 1 | |a Vieira, Tatiana F |e verfasserin |4 aut | |
| 700 | 1 | |a Rodrigues, Ana Rita O |e verfasserin |4 aut | |
| 700 | 1 | |a Pereira, David M |e verfasserin |4 aut | |
| 700 | 1 | |a Sousa, Sérgio F |e verfasserin |4 aut | |
| 700 | 1 | |a Castanheira, Elisabete M S |e verfasserin |4 aut | |
| 700 | 1 | |a Fortes, A Gil |e verfasserin |4 aut | |
| 700 | 1 | |a Gonçalves, M Sameiro T |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Molecules (Basel, Switzerland) |d 2004 |g 26(2021), 21 vom: 31. Okt. |w (DE-627)NLM172073448 |x 1420-3049 |7 nnns |
| 773 | 1 | 8 | |g volume:26 |g year:2021 |g number:21 |g day:31 |g month:10 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.3390/molecules26216616 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 26 |j 2021 |e 21 |b 31 |c 10 | ||