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Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy

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Author(s):
Rosa, Matheus Elias ; Brito, Ivanildo A. ; Lago, Joao Henrique G. ; Caseli, Luciano
Total Authors: 4
Document type: Journal article
Source: RESULTS IN SURFACES AND INTERFACES; v. 17, p. 11-pg., 2024-09-25.
Abstract

This study explores how the unsaturation patterns of three acetogenins from Porcelia macrocarpa (2S,3R,4R)-3hydroxy-4-methyl-2-(eicos-11 '-yn-19 '-enyl)-butanolide (1), (2S,3R,4R)-3-hydroxy-4-methyl-2-(eicos-11 '-ynyl)butanolide (2), and (2S,3R,4R)-3-hydroxy-4-methyl-2-eicosyl-butanolide (3)-affect their interactions with lipid interfaces, using Langmuir monolayers of dipalmitoyl-phosphoethanolamine (DPPE) as a model for protozoal membranes. The hypothesis posits that unsaturated acetogenins (1 and 2) will exhibit distinct behaviors compared to the saturated acetogenin (3) due to structural differences. Experiments incorporated each acetogenin into DPPE monolayers, employing techniques like tensiometry, dilatational rheology, infrared spectroscopy, and Brewster angle microscopy (BAM) to assess interactions and changes in film properties. Results showed that unsaturated acetogenin 1, active against Leishmania infantum and Trypanosoma cruzi, destabilized the film and induced rapid molecular reorganization, while acetogenin 2, inactive against these parasites, uniquely increased the viscous contribution to viscoelasticity. Saturated acetogenin 3 did not integrate into the film. All acetogenins enhanced fluidity, reducing elasticity and viscosity, with BAM revealing phase separation only in acetogenin 2. Infrared spectroscopy underscored the impact of drug-lipid interactions, leading to the conclusion that unsaturated acetogenins 1 and 2 have a more significant influence on thermodynamic and structural properties than acetogenin 3, offering insights into their potential therapeutic mechanisms. (AU)

FAPESP's process: 22/03736-7 - Nanostructured interfaces for the investigation of bioactive substances in cell membrane models and for the construction of optoelectronic devices
Grantee:Luciano Caseli
Support Opportunities: Regular Research Grants
FAPESP's process: 18/22214-6 - Towards a convergence of technologies: from sensing and biosensing to information visualization and machine learning for data analysis in clinical diagnosis
Grantee:Osvaldo Novais de Oliveira Junior
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 21/15084-1 - Interaction of natural acetogenins with biological activity in membrane models at the air-water interface
Grantee:Matheus Elias Rosa
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)