Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis, Computational and Nanoencapsulation Studies on Eugenol-Derived Insecticides

Catarina Coelho
,
Renato Pereira
,
Tatiana Vieira
ORCID logo ,
Cláudia Teixeira
ORCID logo ,
Maria Fernandes
,
Ana Rodrigues
ORCID logo ,
David Pereira
* ORCID logo ,
Sérgio Sousa
,
António Fortes
,
Elisabete Castanheira
ORCID logo ,
Maria Gonçalves
* ORCID logo
Version 1 : Received: 27 March 2022 / Approved: 28 March 2022 / Online: 28 March 2022 (06:12:52 CEST)

How to cite: Coelho, C.; Pereira, R.; Vieira, T.; Teixeira, C.; Fernandes, M.; Rodrigues, A.; Pereira, D.; Sousa, S.; Fortes, A.; Castanheira, E.; Gonçalves, M. Synthesis, Computational and Nanoencapsulation Studies on Eugenol-Derived Insecticides. Preprints 2022, 2022030354. https://doi.org/10.20944/preprints202203.0354.v1 Coelho, C.; Pereira, R.; Vieira, T.; Teixeira, C.; Fernandes, M.; Rodrigues, A.; Pereira, D.; Sousa, S.; Fortes, A.; Castanheira, E.; Gonçalves, M. Synthesis, Computational and Nanoencapsulation Studies on Eugenol-Derived Insecticides. Preprints 2022, 2022030354. https://doi.org/10.20944/preprints202203.0354.v1

Abstract

A new set of alkoxy alcohols were synthesised by reaction of eugenol oxirane with aliphatic and aromatic alcohols. These eugenol derivatives were evaluated against their effect upon the viability of the insect cell line Sf9 (Spodoptera frugiperda).The most promising compounds, 4-(3-(tert-butoxy)-2-hydroxypropyl)-2-methoxyphenol and 4-(2-((4-fluorobenzyl)oxy)-3-hydroxypropyl)-2-methoxyphenol were submitted to in silico assays to predict possible targets. Thought an Inverted Virtual Screening approach, 23 common pesticide targets were screened and the top 2 targets predicted were further evaluated through molecular dynamics simulations and free energy calculations. In addition, these to eugenol derivatives were subjected to encapsulation and release assays using liposome-based nanosystems of egg phosphatidylcholine/cholesterol (7:3), with encapsulation efficiencies higher than 90% and release profiles well described by both Korsmeyer-Peppas and Weibull models.

Keywords

insecticides; semi-synthetic pesticides; eugenol derivatives; alkoxy alcohols; essential oils; nanoencapsulation biopesticides

Subject

Chemistry and Materials Science, Medicinal Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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