Synthesis, computational and nanoencapsulation studies on eugenol-derived insecticides

• Autor(a) principal: Coelho, Catarina M. M.
• Data de Publicação: 2022
• Outros Autores: Pereira, Renato B., Vieira, Tatiana F., Teixeira, Cláudia M., Fernandes, Maria José Gomes, Rodrigues, Ana Rita O., Pereira, David M., Sousa, Sérgio F., Fortes, A. Gil, Castanheira, Elisabete M. S., Gonçalves, M. Sameiro T.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: https://hdl.handle.net/1822/86859
• topic: Eugenol derivatives; Nanoencapsulation; Insecticides; Insecticides formulations; Science & Technology

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. Throught an Inverted Virtual Screening approach, 23 common pesticide targets were screened and the top 2 targets predicted were further analyzed through 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 higher than 90% and release profiles well described by both Korsmeyer-Peppas and Weibull models.