Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes

Detalhes bibliográficos
Autor(a) principal: Rosa, Matheus Elias
Data de Publicação: 2022
Outros Autores: Conserva, Geanne A. Alves, Passero, Luiz Felipe D. [UNESP], Lago, João Henrique G., Caseli, Luciano
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.bioorg.2022.105814
http://hdl.handle.net/11449/239922
Resumo: The present work evaluated the antiprotozoal activity of isolinderanolide E, isolated from the Brazilian plant Nectandra oppositifolia, against promastigote forms of Leishmania (Leishmania) amazonensis. The compound exhibited an EC50 value of 20.3 μM, similar to the positive control miltefosine (IC50 of 19.4 μM), and reduced toxicity to macrophages (CC50 > 200 μM). Based on these results, Langmuir monolayers of two unsaturated lipids: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), were employed as a model of mammalian and parasite membranes, respectively, to study the interaction of isolinderanolide E at a molecular level. The films were characterized with tensiometry (surface pressure-area isotherms and surface pressure-time curves), infrared spectroscopy, and Brewster angle microscopy (BAM). This compound changed the profile of the isotherms leading to fluid DOPC and DOPE monolayers, which were not able to attain rigid states even with compression. Infrared spectroscopy showed that the bioactive compound decreases the trans/gauche ratio conformers related to the molecular conformational disorder. BAM showed the formation of specific aggregates upon drug incorporation. In conclusion, isolinderanolide E changes the thermodynamic, mechanical, structural, and morphological characteristics of the monolayer of these unsaturated lipids, which may be essential to understand the action at the molecular level bioactives in biointerfaces.
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spelling Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranesAir-water interfaceDOPCDOPEIsolinderanolide ELeishmania (L.) amazonensisMonolayersThe present work evaluated the antiprotozoal activity of isolinderanolide E, isolated from the Brazilian plant Nectandra oppositifolia, against promastigote forms of Leishmania (Leishmania) amazonensis. The compound exhibited an EC50 value of 20.3 μM, similar to the positive control miltefosine (IC50 of 19.4 μM), and reduced toxicity to macrophages (CC50 > 200 μM). Based on these results, Langmuir monolayers of two unsaturated lipids: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), were employed as a model of mammalian and parasite membranes, respectively, to study the interaction of isolinderanolide E at a molecular level. The films were characterized with tensiometry (surface pressure-area isotherms and surface pressure-time curves), infrared spectroscopy, and Brewster angle microscopy (BAM). This compound changed the profile of the isotherms leading to fluid DOPC and DOPE monolayers, which were not able to attain rigid states even with compression. Infrared spectroscopy showed that the bioactive compound decreases the trans/gauche ratio conformers related to the molecular conformational disorder. BAM showed the formation of specific aggregates upon drug incorporation. In conclusion, isolinderanolide E changes the thermodynamic, mechanical, structural, and morphological characteristics of the monolayer of these unsaturated lipids, which may be essential to understand the action at the molecular level bioactives in biointerfaces.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Laboratory of Hybrid Materials Chemistry Department Federal University of São Paulo (UNIFESP), SPLaboratory of Chemical Biology Center for Natural and Human Sciences Federal University of ABC (UFABC), SPInstitute of Biosciences São Paulo State University (UNESP), SPInstitute for Advanced Studies of Ocean São Paulo State University (UNESP), SPInstitute of Biosciences São Paulo State University (UNESP), SPInstitute for Advanced Studies of Ocean São Paulo State University (UNESP), SPCAPES: 001FAPESP: 2016/20633-6FAPESP: 2018/22214-6FAPESP: 2018/24077-6FAPESP: 2019/03239-0FAPESP: 2019/04407-4FAPESP: 2021/02789-7CNPq: 301354/2019-7Universidade de São Paulo (USP)Universidade Federal do ABC (UFABC)Universidade Estadual Paulista (UNESP)Rosa, Matheus EliasConserva, Geanne A. AlvesPassero, Luiz Felipe D. [UNESP]Lago, João Henrique G.Caseli, Luciano2023-03-01T19:53:20Z2023-03-01T19:53:20Z2022-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.bioorg.2022.105814Bioorganic Chemistry, v. 124.1090-21200045-2068http://hdl.handle.net/11449/23992210.1016/j.bioorg.2022.1058142-s2.0-85128651164Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengBioorganic Chemistryinfo:eu-repo/semantics/openAccess2023-03-01T19:53:20Zoai:repositorio.unesp.br:11449/239922Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T17:22:39.266747Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
title Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
spellingShingle Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
Rosa, Matheus Elias
Air-water interface
DOPC
DOPE
Isolinderanolide E
Leishmania (L.) amazonensis
Monolayers
title_short Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
title_full Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
title_fullStr Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
title_full_unstemmed Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
title_sort Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes
author Rosa, Matheus Elias
author_facet Rosa, Matheus Elias
Conserva, Geanne A. Alves
Passero, Luiz Felipe D. [UNESP]
Lago, João Henrique G.
Caseli, Luciano
author_role author
author2 Conserva, Geanne A. Alves
Passero, Luiz Felipe D. [UNESP]
Lago, João Henrique G.
Caseli, Luciano
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidade de São Paulo (USP)
Universidade Federal do ABC (UFABC)
Universidade Estadual Paulista (UNESP)
dc.contributor.author.fl_str_mv Rosa, Matheus Elias
Conserva, Geanne A. Alves
Passero, Luiz Felipe D. [UNESP]
Lago, João Henrique G.
Caseli, Luciano
dc.subject.por.fl_str_mv Air-water interface
DOPC
DOPE
Isolinderanolide E
Leishmania (L.) amazonensis
Monolayers
topic Air-water interface
DOPC
DOPE
Isolinderanolide E
Leishmania (L.) amazonensis
Monolayers
description The present work evaluated the antiprotozoal activity of isolinderanolide E, isolated from the Brazilian plant Nectandra oppositifolia, against promastigote forms of Leishmania (Leishmania) amazonensis. The compound exhibited an EC50 value of 20.3 μM, similar to the positive control miltefosine (IC50 of 19.4 μM), and reduced toxicity to macrophages (CC50 > 200 μM). Based on these results, Langmuir monolayers of two unsaturated lipids: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), were employed as a model of mammalian and parasite membranes, respectively, to study the interaction of isolinderanolide E at a molecular level. The films were characterized with tensiometry (surface pressure-area isotherms and surface pressure-time curves), infrared spectroscopy, and Brewster angle microscopy (BAM). This compound changed the profile of the isotherms leading to fluid DOPC and DOPE monolayers, which were not able to attain rigid states even with compression. Infrared spectroscopy showed that the bioactive compound decreases the trans/gauche ratio conformers related to the molecular conformational disorder. BAM showed the formation of specific aggregates upon drug incorporation. In conclusion, isolinderanolide E changes the thermodynamic, mechanical, structural, and morphological characteristics of the monolayer of these unsaturated lipids, which may be essential to understand the action at the molecular level bioactives in biointerfaces.
publishDate 2022
dc.date.none.fl_str_mv 2022-07-01
2023-03-01T19:53:20Z
2023-03-01T19:53:20Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1016/j.bioorg.2022.105814
Bioorganic Chemistry, v. 124.
1090-2120
0045-2068
http://hdl.handle.net/11449/239922
10.1016/j.bioorg.2022.105814
2-s2.0-85128651164
url http://dx.doi.org/10.1016/j.bioorg.2022.105814
http://hdl.handle.net/11449/239922
identifier_str_mv Bioorganic Chemistry, v. 124.
1090-2120
0045-2068
10.1016/j.bioorg.2022.105814
2-s2.0-85128651164
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Bioorganic Chemistry
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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