Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy
This study explores how the unsaturation patterns of three acetogenins from Porcelia macrocarpa (2S,3R,4R)-3-hydroxy-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 t...
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Elsevier
2024-10-01
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| Series: | Results in Surfaces and Interfaces |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666845924001260 |
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| author | Matheus Elias Rosa Ivanildo A. Brito João Henrique G. Lago Luciano Caseli |
| author_facet | Matheus Elias Rosa Ivanildo A. Brito João Henrique G. Lago Luciano Caseli |
| author_sort | Matheus Elias Rosa |
| collection | DOAJ |
| description | This study explores how the unsaturation patterns of three acetogenins from Porcelia macrocarpa (2S,3R,4R)-3-hydroxy-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. |
| format | Article |
| id | doaj-art-c5f6e56d5f824f3781b679948f1de912 |
| institution | Kabale University |
| issn | 2666-8459 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Surfaces and Interfaces |
| spelling | doaj-art-c5f6e56d5f824f3781b679948f1de9122024-12-02T05:06:57ZengElsevierResults in Surfaces and Interfaces2666-84592024-10-0117100306Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopyMatheus Elias Rosa0Ivanildo A. Brito1João Henrique G. Lago2Luciano Caseli3Laboratory of Hybrid Material, Chemistry Department, Federal University of São Paulo (UNIFESP), Diadema, SP, BrazilLaboratory of Chemical Biology, Center for Natural and Human Sciences, Federal University of ABC (UFABC), Santo Andre, SP, BrazilLaboratory of Chemical Biology, Center for Natural and Human Sciences, Federal University of ABC (UFABC), Santo Andre, SP, BrazilLaboratory of Hybrid Material, Chemistry Department, Federal University of São Paulo (UNIFESP), Diadema, SP, Brazil; Corresponding author.This study explores how the unsaturation patterns of three acetogenins from Porcelia macrocarpa (2S,3R,4R)-3-hydroxy-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.http://www.sciencedirect.com/science/article/pii/S2666845924001260TensiometryLangmuir monolayersCell membranes modelsAir-water interface |
| spellingShingle | Matheus Elias Rosa Ivanildo A. Brito João Henrique G. Lago Luciano Caseli Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy Results in Surfaces and Interfaces Tensiometry Langmuir monolayers Cell membranes models Air-water interface |
| title | Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy |
| title_full | Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy |
| title_fullStr | Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy |
| title_full_unstemmed | Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy |
| title_short | Exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions: Insights from surface chemistry, rheology, and spectroscopy |
| title_sort | exploring the influence of acetylenic acetogenin unsaturation patterns on lipid interface interactions insights from surface chemistry rheology and spectroscopy |
| topic | Tensiometry Langmuir monolayers Cell membranes models Air-water interface |
| url | http://www.sciencedirect.com/science/article/pii/S2666845924001260 |
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