Synthesis, computational and nanoencapsulation studies on eugenol-derived insecticides

• Type: Article in International Scientific Journal
• Date: 2022

Authors

Coelho, CMM (Author) Other; Pereira, RB (Author) Other; Vieira, TF (Author) Other; Teixeira, CM (Author) Other; Fernandes, MJG (Author) Other; Rodrigues, ARO (Author) Other; David M Pereira (Author) FFUP; Sousa, SF (Author) Other; Fortes, AG (Author) Other; Castanheira, EMS (Author) Other; Goncalves, MST (Author) Other

Journal

Title: New Journal of Chemistry

ISSN: 1144-0546

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 0 Citations

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Other information

Authenticus ID: P-00W-BRQ

DOI: 10.1039/d2nj01893d

Abstract (EN): A new set of alkoxy alcohols were synthesised by the reaction of eugenol oxirane with aliphatic and aromatic alcohols. These eugenol derivatives were evaluated against their effect upon the viability of an 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. Using an inverted virtual screening approach, 23 common pesticide targets were screened and the top 2 targets predicted were further analyzed using molecular dynamics simulations and free energy calculations. In addition, these eugenol derivatives were subjected to encapsulation and release assays using liposome-based nanosystems of egg phosphatidylcholine : cholesterol (7 : 3), with encapsulation efficiencies of higher than 90% and release profiles well described by both Korsmeyer-Peppas and Weibull models.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 13