From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers

Detalhes bibliográficos
Autor(a) principal: Tapia, M. J.
Data de Publicação: 2014
Outros Autores: Monteserín, M., Burrows, H. D., Almeida, J. A. S., Pais, A. A. C. C., Pina, J., Seixas de Melo, J. S., Jarmelo, S., Estelrich, J.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/28727
https://doi.org/10.1039/c4sm02145b
Resumo: The combination of various experimental techniques with theoretical simulations has allowed elucidation of the mode of incorporation of fluorene based derivatives into phospholipid bilayers. Molecular dynamics (MD) simulations on a fully hydrated 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine (DMPC) bilayer, with benzene (B), biphenyl (BP), fluorene (F) and tri-(9,9-di-n-octylfluorenyl-2,7-diyl), TF, have provided insights into the topography of these molecules when they are present in the phospholipid bilayer, and suggest marked differences between the behavior of the small molecules and the oligomer. Further information on the interaction of neutral fluorenes within the phospholipid bilayer was obtained by an infrared (IR) spectroscopic study of films of DMPC and of the phospholipid with PFO deuterated specifically on its alkyl chains (DMPC–PFO-d34). This was complemented by measurements of the effect of F, TF and two neutral polymers: polyfluorene poly(9,9-di-n-octylfluorenyl-2,7-diyl), PFO, and poly(9,9-di-n-dodecylfluorenyl-2,7-diyl), PFD, on the phospholipid phase transition temperature using differential scanning calorimetry (DSC). Changes in liposome size upon addition of F and PFO were followed by dynamic light scattering. In addition, the spectroscopic properties of F, TF, PFO and PFD solubilised in DMPC liposomes (absorption, steady-state and time-resolved fluorescence) were compared with those of the same probes in typical organic solvents (chloroform, cyclohexane and ethanol). Combining the insight from MD simulations with the results at the molecular level from the various experimental techniques suggests that while the small molecules have a tendency to be located in the phospholipid head group region, the polymers are incorporated within the lipid bilayers, with the backbone predominantly orthogonal to the phospholipid alkyl chains and with interdigitation of them and the PFO alkyl chains.
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spelling From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayersThe combination of various experimental techniques with theoretical simulations has allowed elucidation of the mode of incorporation of fluorene based derivatives into phospholipid bilayers. Molecular dynamics (MD) simulations on a fully hydrated 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine (DMPC) bilayer, with benzene (B), biphenyl (BP), fluorene (F) and tri-(9,9-di-n-octylfluorenyl-2,7-diyl), TF, have provided insights into the topography of these molecules when they are present in the phospholipid bilayer, and suggest marked differences between the behavior of the small molecules and the oligomer. Further information on the interaction of neutral fluorenes within the phospholipid bilayer was obtained by an infrared (IR) spectroscopic study of films of DMPC and of the phospholipid with PFO deuterated specifically on its alkyl chains (DMPC–PFO-d34). This was complemented by measurements of the effect of F, TF and two neutral polymers: polyfluorene poly(9,9-di-n-octylfluorenyl-2,7-diyl), PFO, and poly(9,9-di-n-dodecylfluorenyl-2,7-diyl), PFD, on the phospholipid phase transition temperature using differential scanning calorimetry (DSC). Changes in liposome size upon addition of F and PFO were followed by dynamic light scattering. In addition, the spectroscopic properties of F, TF, PFO and PFD solubilised in DMPC liposomes (absorption, steady-state and time-resolved fluorescence) were compared with those of the same probes in typical organic solvents (chloroform, cyclohexane and ethanol). Combining the insight from MD simulations with the results at the molecular level from the various experimental techniques suggests that while the small molecules have a tendency to be located in the phospholipid head group region, the polymers are incorporated within the lipid bilayers, with the backbone predominantly orthogonal to the phospholipid alkyl chains and with interdigitation of them and the PFO alkyl chains.Royal Society of Chemistry2014-11-05info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/28727http://hdl.handle.net/10316/28727https://doi.org/10.1039/c4sm02145beng1744-6848Tapia, M. J.Monteserín, M.Burrows, H. D.Almeida, J. A. S.Pais, A. A. C. C.Pina, J.Seixas de Melo, J. S.Jarmelo, S.Estelrich, J.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2021-11-03T10:06:43Zoai:estudogeral.uc.pt:10316/28727Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:50.851750Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
title From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
spellingShingle From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
Tapia, M. J.
title_short From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
title_full From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
title_fullStr From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
title_full_unstemmed From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
title_sort From molecular modelling to photophysics of neutral oligo- and polyfluorenes incorporated into phospholipid bilayers
author Tapia, M. J.
author_facet Tapia, M. J.
Monteserín, M.
Burrows, H. D.
Almeida, J. A. S.
Pais, A. A. C. C.
Pina, J.
Seixas de Melo, J. S.
Jarmelo, S.
Estelrich, J.
author_role author
author2 Monteserín, M.
Burrows, H. D.
Almeida, J. A. S.
Pais, A. A. C. C.
Pina, J.
Seixas de Melo, J. S.
Jarmelo, S.
Estelrich, J.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Tapia, M. J.
Monteserín, M.
Burrows, H. D.
Almeida, J. A. S.
Pais, A. A. C. C.
Pina, J.
Seixas de Melo, J. S.
Jarmelo, S.
Estelrich, J.
description The combination of various experimental techniques with theoretical simulations has allowed elucidation of the mode of incorporation of fluorene based derivatives into phospholipid bilayers. Molecular dynamics (MD) simulations on a fully hydrated 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine (DMPC) bilayer, with benzene (B), biphenyl (BP), fluorene (F) and tri-(9,9-di-n-octylfluorenyl-2,7-diyl), TF, have provided insights into the topography of these molecules when they are present in the phospholipid bilayer, and suggest marked differences between the behavior of the small molecules and the oligomer. Further information on the interaction of neutral fluorenes within the phospholipid bilayer was obtained by an infrared (IR) spectroscopic study of films of DMPC and of the phospholipid with PFO deuterated specifically on its alkyl chains (DMPC–PFO-d34). This was complemented by measurements of the effect of F, TF and two neutral polymers: polyfluorene poly(9,9-di-n-octylfluorenyl-2,7-diyl), PFO, and poly(9,9-di-n-dodecylfluorenyl-2,7-diyl), PFD, on the phospholipid phase transition temperature using differential scanning calorimetry (DSC). Changes in liposome size upon addition of F and PFO were followed by dynamic light scattering. In addition, the spectroscopic properties of F, TF, PFO and PFD solubilised in DMPC liposomes (absorption, steady-state and time-resolved fluorescence) were compared with those of the same probes in typical organic solvents (chloroform, cyclohexane and ethanol). Combining the insight from MD simulations with the results at the molecular level from the various experimental techniques suggests that while the small molecules have a tendency to be located in the phospholipid head group region, the polymers are incorporated within the lipid bilayers, with the backbone predominantly orthogonal to the phospholipid alkyl chains and with interdigitation of them and the PFO alkyl chains.
publishDate 2014
dc.date.none.fl_str_mv 2014-11-05
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10316/28727
http://hdl.handle.net/10316/28727
https://doi.org/10.1039/c4sm02145b
url http://hdl.handle.net/10316/28727
https://doi.org/10.1039/c4sm02145b
dc.language.iso.fl_str_mv eng
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dc.relation.none.fl_str_mv 1744-6848
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dc.publisher.none.fl_str_mv Royal Society of Chemistry
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