Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation

Autores
Wood, Irene; Martini, María Florencia; Pickholz, Mónica Andrea
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, we report a Molecular Dynamics (MD) simulations study of relevant biological molecules as serotonin (neutral and protonated) and its precursors, tryptophan and 5-hydroxy-tryptophan, in a fully hydrated bilayer of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-choline (POPC). The simulations were carried out at the fluid lamellar phase of POPC at constant pressure and temperature conditions. Two guest molecules of each type were initially placed at the water phase. We have analyzed, the main localization, preferential orientation and specific interactions of the guest molecules within the bilayer. During the simulation run, the four molecules were preferentially found at the water-lipid interphase. We found that the interactions that stabilized the systems are essentially hydrogen bonds, salt bridges and cation-π. None of the guest molecules have access to the hydrophobic region of the bilayer. Besides, zwitterionic molecules have access to the water phase, while protonated serotonin is anchored in the interphase. Even taking into account that these simulations were done using a model membrane, our results suggest that the studied molecules could not cross the blood brain barrier by diffusion. These results are in good agreement with works that show that serotonin and Trp do not cross the BBB by simple diffusion.
Fil: Wood, Irene. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina
Fil: Martini, María Florencia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Pickholz, Mónica Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Lipid Membranes
Serotonine
Trypthopan
Interaction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/2026
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/2026
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulationWood, IreneMartini, María FlorenciaPickholz, Mónica AndreaLipid MembranesSerotonineTrypthopanInteractionhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1In this work, we report a Molecular Dynamics (MD) simulations study of relevant biological molecules as serotonin (neutral and protonated) and its precursors, tryptophan and 5-hydroxy-tryptophan, in a fully hydrated bilayer of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-choline (POPC). The simulations were carried out at the fluid lamellar phase of POPC at constant pressure and temperature conditions. Two guest molecules of each type were initially placed at the water phase. We have analyzed, the main localization, preferential orientation and specific interactions of the guest molecules within the bilayer. During the simulation run, the four molecules were preferentially found at the water-lipid interphase. We found that the interactions that stabilized the systems are essentially hydrogen bonds, salt bridges and cation-π. None of the guest molecules have access to the hydrophobic region of the bilayer. Besides, zwitterionic molecules have access to the water phase, while protonated serotonin is anchored in the interphase. Even taking into account that these simulations were done using a model membrane, our results suggest that the studied molecules could not cross the blood brain barrier by diffusion. These results are in good agreement with works that show that serotonin and Trp do not cross the BBB by simple diffusion.Fil: Wood, Irene. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; ArgentinaFil: Martini, María Florencia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Pickholz, Mónica Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science2013-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2026Wood, Irene; Martini, María Florencia; Pickholz, Mónica Andrea; Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation; Elsevier Science; Journal Of Molecular Structure; 1045; 6-2013; 124-1300022-2860enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2013.04.011info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:28:36Zoai:ri.conicet.gov.ar:11336/2026instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:28:37.117CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
title Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
spellingShingle Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
Wood, Irene
Lipid Membranes
Serotonine
Trypthopan
Interaction
title_short Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
title_full Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
title_fullStr Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
title_full_unstemmed Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
title_sort Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation
dc.creator.none.fl_str_mv Wood, Irene
Martini, María Florencia
Pickholz, Mónica Andrea
author Wood, Irene
author_facet Wood, Irene
Martini, María Florencia
Pickholz, Mónica Andrea
author_role author
author2 Martini, María Florencia
Pickholz, Mónica Andrea
author2_role author
author
dc.subject.none.fl_str_mv Lipid Membranes
Serotonine
Trypthopan
Interaction
topic Lipid Membranes
Serotonine
Trypthopan
Interaction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work, we report a Molecular Dynamics (MD) simulations study of relevant biological molecules as serotonin (neutral and protonated) and its precursors, tryptophan and 5-hydroxy-tryptophan, in a fully hydrated bilayer of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-choline (POPC). The simulations were carried out at the fluid lamellar phase of POPC at constant pressure and temperature conditions. Two guest molecules of each type were initially placed at the water phase. We have analyzed, the main localization, preferential orientation and specific interactions of the guest molecules within the bilayer. During the simulation run, the four molecules were preferentially found at the water-lipid interphase. We found that the interactions that stabilized the systems are essentially hydrogen bonds, salt bridges and cation-π. None of the guest molecules have access to the hydrophobic region of the bilayer. Besides, zwitterionic molecules have access to the water phase, while protonated serotonin is anchored in the interphase. Even taking into account that these simulations were done using a model membrane, our results suggest that the studied molecules could not cross the blood brain barrier by diffusion. These results are in good agreement with works that show that serotonin and Trp do not cross the BBB by simple diffusion.
Fil: Wood, Irene. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina
Fil: Martini, María Florencia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Pickholz, Mónica Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Tecnologia Farmaceutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description In this work, we report a Molecular Dynamics (MD) simulations study of relevant biological molecules as serotonin (neutral and protonated) and its precursors, tryptophan and 5-hydroxy-tryptophan, in a fully hydrated bilayer of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-choline (POPC). The simulations were carried out at the fluid lamellar phase of POPC at constant pressure and temperature conditions. Two guest molecules of each type were initially placed at the water phase. We have analyzed, the main localization, preferential orientation and specific interactions of the guest molecules within the bilayer. During the simulation run, the four molecules were preferentially found at the water-lipid interphase. We found that the interactions that stabilized the systems are essentially hydrogen bonds, salt bridges and cation-π. None of the guest molecules have access to the hydrophobic region of the bilayer. Besides, zwitterionic molecules have access to the water phase, while protonated serotonin is anchored in the interphase. Even taking into account that these simulations were done using a model membrane, our results suggest that the studied molecules could not cross the blood brain barrier by diffusion. These results are in good agreement with works that show that serotonin and Trp do not cross the BBB by simple diffusion.
publishDate 2013
dc.date.none.fl_str_mv 2013-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/2026
Wood, Irene; Martini, María Florencia; Pickholz, Mónica Andrea; Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation; Elsevier Science; Journal Of Molecular Structure; 1045; 6-2013; 124-130
0022-2860
url http://hdl.handle.net/11336/2026
identifier_str_mv Wood, Irene; Martini, María Florencia; Pickholz, Mónica Andrea; Similarities and differences of serotonin and its precursors in their interactions with model membranes studied by molecular dynamics simulation; Elsevier Science; Journal Of Molecular Structure; 1045; 6-2013; 124-130
0022-2860
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2013.04.011
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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