nteraction of isolinderanolide E obtained from Nectandra oppositifolia with biomembrane model

Autor(es)

Rosa, Matheus Elias ^[1] ; Alves Conserva, Geanne A. ^[2] ; Lago, Joao Henrique G. ^[2] ; Caseli, Luciano ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Paulo, Dept Chem, Diadema, SP - Brazil

^[2] Fed Univ ABC, Ctr Nat & Human Sci, Santo Andre, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES; v. 1863, n. 10 OCT 2021.
• Citações Web of Science: 0

Resumo

A long-tail lactone, named isolinderanolide E, was obtained from Nectandra oppositifolia and incorporated in Langmuir monolayers of dipalmitoyl-phosphoethanolamine (DPPE) as a model of microbial membranes. The compound was dissolved in chloroform and mixed with DPPE to provide mixed solutions spread on the air-water interface. After solvent evaporation, mixed monolayers were formed, and surface pressure-area isotherms, dilatational rheology, Brewster angle microscopy (BAM), and infrared spectroscopy were employed to characterize the prodrug-membrane interactions. Isolinderanolide E expanded DPPE monolayers, denoting repulsive interactions. At 30 mN/m, the monolayer presented higher viscoelastic and in-plane elasticity parameters and an increased ratio of all-trans/gauche conformers of the alkyl chains, confirming molecular order. Morphology of the monolayer was analyzed by BAM, which revealed a more homogeneous distribution of Isolinderanolide E along the DPPE monolayer than the prodrug directly spread at the interface, which tends to aggregate. A molecular model proposing the molecular orientation of the amphiphilic drug is presented and explained by the distortion of the alkyl chains as well as by viscoelastic changes. In conclusion, the prodrug changes the thermodynamic, rheological, morphological, and structural properties of the DPPE monolayer, which may be essential to understand, at the molecular level, the action of bioactives in selected membrane models. (AU)

• Processo FAPESP: 19/03239-0 - Interfaces nanoestruturadas para a investigação de substâncias bioativas em modelos de membrana celular e para a construção de dispositivos optoeletrônicos enzimáticos
• Beneficiário: Luciano Caseli
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 16/20633-6 - Metabolitos bioativos de Nectandra oppositifolia Nees & Mart. (Lauraceae): caracterização molecular, avaliação do potencial antiparasitário in vitro e in vivo e determinação dos mecanismos de ação
• Beneficiário: Geanne Alexsandra Alves Conserva
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 18/22214-6 - Rumo à convergência de tecnologias: de sensores e biossensores à visualização de informação e aprendizado de máquina para análise de dados em diagnóstico clínico
• Beneficiário: Osvaldo Novais de Oliveira Junior
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 19/04407-4 - Estudo da atividade superficial de lactonas alquiladas e sua interação em modelos de membrana celular
• Beneficiário: Matheus Elias Rosa
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica