Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer

Autores
Miguel, Virginia; Defonsi Lestard, Maria Eliana; Tuttolomondo, María Victoria; Díaz, Sonia B.; Ben Altabef, Aida; Puiatti, Marcelo; Pierini, Adriana Beatriz
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We present molecular dynamics (MD) simulation studies of the interaction of a chemo preventive and protective agent, S-methyl methanethiosulfonate (MMTS), with a model bilayer of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC). We analyzed and compared its diffusion mechanisms with the related molecule dimethyl sulfoxide (DMSO). We obtained spatially resolved free energy profiles of MMTS partition into a DPPC bilayer in the liquid-crystalline phase through Potential of Mean Force (PMF) calculations using an umbrella sampling technique. These profiles showed a minimum for MMTS close to the carbonyl region of DPPC. The location of MMTS molecules in the DPPC bilayer observed in the MD were confirmed by previous SERS studies.1 We decomposed PMF profiles into entropic and enthalpic contributions. These results showed that the driving force for the partitioning of MMTS into the upper region of DPPC is driven by a favorable entropy change while partitioning into the acyl chains is driven by enthalpy. On the other hand, the partition of DMSO into the membrane is not favored, and is driven by entropy instead of enthalpy. Free diffusion MD simulations using all atom and coarse grained (CG) models of DPPC in presence of MMTS were used to analyze the effect of DPPC-MMTS interaction. Density profiles showed that MMTS locates preferentially in the carbonyl region, as expected according to the PMF profile and the experimental evidence. MMTS presented two differential effects over the packing of DPPC hydrocarbonate chains at low or at high molar ratios. An ordering effect was observed when a CG MMTS model was used. Finally, free diffusion MD and PMF decomposition for DMSO were used for comparison.
Fil: Miguel, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; Argentina
Fil: Defonsi Lestard, Maria Eliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Tuttolomondo, María Victoria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Díaz, Sonia B.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Ben Altabef, Aida. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Puiatti, Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; Argentina
Materia
Molecular Dynamics
Dppc
S-Methyl Methanethiosulfonate
Pmf
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:11336/7409
Acceder
id CONICETDig_0682c47494f7816b025daec4cbda9c6c
oai_identifier_str oai:ri.conicet.gov.ar:11336/7409
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC BilayerMiguel, VirginiaDefonsi Lestard, Maria ElianaTuttolomondo, María VictoriaDíaz, Sonia B.Ben Altabef, AidaPuiatti, MarceloPierini, Adriana BeatrizMolecular DynamicsDppcS-Methyl MethanethiosulfonatePmfhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We present molecular dynamics (MD) simulation studies of the interaction of a chemo preventive and protective agent, S-methyl methanethiosulfonate (MMTS), with a model bilayer of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC). We analyzed and compared its diffusion mechanisms with the related molecule dimethyl sulfoxide (DMSO). We obtained spatially resolved free energy profiles of MMTS partition into a DPPC bilayer in the liquid-crystalline phase through Potential of Mean Force (PMF) calculations using an umbrella sampling technique. These profiles showed a minimum for MMTS close to the carbonyl region of DPPC. The location of MMTS molecules in the DPPC bilayer observed in the MD were confirmed by previous SERS studies.1 We decomposed PMF profiles into entropic and enthalpic contributions. These results showed that the driving force for the partitioning of MMTS into the upper region of DPPC is driven by a favorable entropy change while partitioning into the acyl chains is driven by enthalpy. On the other hand, the partition of DMSO into the membrane is not favored, and is driven by entropy instead of enthalpy. Free diffusion MD simulations using all atom and coarse grained (CG) models of DPPC in presence of MMTS were used to analyze the effect of DPPC-MMTS interaction. Density profiles showed that MMTS locates preferentially in the carbonyl region, as expected according to the PMF profile and the experimental evidence. MMTS presented two differential effects over the packing of DPPC hydrocarbonate chains at low or at high molar ratios. An ordering effect was observed when a CG MMTS model was used. Finally, free diffusion MD and PMF decomposition for DMSO were used for comparison.Fil: Miguel, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; ArgentinaFil: Defonsi Lestard, Maria Eliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; ArgentinaFil: Tuttolomondo, María Victoria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; ArgentinaFil: Díaz, Sonia B.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; ArgentinaFil: Ben Altabef, Aida. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; ArgentinaFil: Puiatti, Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; ArgentinaFil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; ArgentinaElsevier2015-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documentapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/7409Miguel, Virginia; Defonsi Lestard, Maria Eliana; Tuttolomondo, María Victoria; Díaz, Sonia B.; Ben Altabef, Aida; et al.; Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer; Elsevier; Biochimica Et Biophysica Acta - Biomembranes; 1858; 1; 10-2015; 38-460005-2736enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0005273615003363info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bbamem.2015.10.008info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:10Zoai:ri.conicet.gov.ar:11336/7409instacron: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:34982025-09-29 10:21:11.074CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
title Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
spellingShingle Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
Miguel, Virginia
Molecular Dynamics
Dppc
S-Methyl Methanethiosulfonate
Pmf
title_short Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
title_full Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
title_fullStr Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
title_full_unstemmed Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
title_sort Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer
dc.creator.none.fl_str_mv Miguel, Virginia
Defonsi Lestard, Maria Eliana
Tuttolomondo, María Victoria
Díaz, Sonia B.
Ben Altabef, Aida
Puiatti, Marcelo
Pierini, Adriana Beatriz
author Miguel, Virginia
author_facet Miguel, Virginia
Defonsi Lestard, Maria Eliana
Tuttolomondo, María Victoria
Díaz, Sonia B.
Ben Altabef, Aida
Puiatti, Marcelo
Pierini, Adriana Beatriz
author_role author
author2 Defonsi Lestard, Maria Eliana
Tuttolomondo, María Victoria
Díaz, Sonia B.
Ben Altabef, Aida
Puiatti, Marcelo
Pierini, Adriana Beatriz
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Molecular Dynamics
Dppc
S-Methyl Methanethiosulfonate
Pmf
topic Molecular Dynamics
Dppc
S-Methyl Methanethiosulfonate
Pmf
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We present molecular dynamics (MD) simulation studies of the interaction of a chemo preventive and protective agent, S-methyl methanethiosulfonate (MMTS), with a model bilayer of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC). We analyzed and compared its diffusion mechanisms with the related molecule dimethyl sulfoxide (DMSO). We obtained spatially resolved free energy profiles of MMTS partition into a DPPC bilayer in the liquid-crystalline phase through Potential of Mean Force (PMF) calculations using an umbrella sampling technique. These profiles showed a minimum for MMTS close to the carbonyl region of DPPC. The location of MMTS molecules in the DPPC bilayer observed in the MD were confirmed by previous SERS studies.1 We decomposed PMF profiles into entropic and enthalpic contributions. These results showed that the driving force for the partitioning of MMTS into the upper region of DPPC is driven by a favorable entropy change while partitioning into the acyl chains is driven by enthalpy. On the other hand, the partition of DMSO into the membrane is not favored, and is driven by entropy instead of enthalpy. Free diffusion MD simulations using all atom and coarse grained (CG) models of DPPC in presence of MMTS were used to analyze the effect of DPPC-MMTS interaction. Density profiles showed that MMTS locates preferentially in the carbonyl region, as expected according to the PMF profile and the experimental evidence. MMTS presented two differential effects over the packing of DPPC hydrocarbonate chains at low or at high molar ratios. An ordering effect was observed when a CG MMTS model was used. Finally, free diffusion MD and PMF decomposition for DMSO were used for comparison.
Fil: Miguel, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; Argentina
Fil: Defonsi Lestard, Maria Eliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Tuttolomondo, María Victoria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Díaz, Sonia B.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Ben Altabef, Aida. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina
Fil: Puiatti, Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto de Investigaciones En Físicoquímica de Córdoba; Argentina
description We present molecular dynamics (MD) simulation studies of the interaction of a chemo preventive and protective agent, S-methyl methanethiosulfonate (MMTS), with a model bilayer of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC). We analyzed and compared its diffusion mechanisms with the related molecule dimethyl sulfoxide (DMSO). We obtained spatially resolved free energy profiles of MMTS partition into a DPPC bilayer in the liquid-crystalline phase through Potential of Mean Force (PMF) calculations using an umbrella sampling technique. These profiles showed a minimum for MMTS close to the carbonyl region of DPPC. The location of MMTS molecules in the DPPC bilayer observed in the MD were confirmed by previous SERS studies.1 We decomposed PMF profiles into entropic and enthalpic contributions. These results showed that the driving force for the partitioning of MMTS into the upper region of DPPC is driven by a favorable entropy change while partitioning into the acyl chains is driven by enthalpy. On the other hand, the partition of DMSO into the membrane is not favored, and is driven by entropy instead of enthalpy. Free diffusion MD simulations using all atom and coarse grained (CG) models of DPPC in presence of MMTS were used to analyze the effect of DPPC-MMTS interaction. Density profiles showed that MMTS locates preferentially in the carbonyl region, as expected according to the PMF profile and the experimental evidence. MMTS presented two differential effects over the packing of DPPC hydrocarbonate chains at low or at high molar ratios. An ordering effect was observed when a CG MMTS model was used. Finally, free diffusion MD and PMF decomposition for DMSO were used for comparison.
publishDate 2015
dc.date.none.fl_str_mv 2015-10
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/11336/7409
Miguel, Virginia; Defonsi Lestard, Maria Eliana; Tuttolomondo, María Victoria; Díaz, Sonia B.; Ben Altabef, Aida; et al.; Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer; Elsevier; Biochimica Et Biophysica Acta - Biomembranes; 1858; 1; 10-2015; 38-46
0005-2736
url http://hdl.handle.net/11336/7409
identifier_str_mv Miguel, Virginia; Defonsi Lestard, Maria Eliana; Tuttolomondo, María Victoria; Díaz, Sonia B.; Ben Altabef, Aida; et al.; Molecular View of the Interaction of S-Methyl Methanethiosulfonate with DPPC Bilayer; Elsevier; Biochimica Et Biophysica Acta - Biomembranes; 1858; 1; 10-2015; 38-46
0005-2736
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0005273615003363
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bbamem.2015.10.008
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
application/vnd.openxmlformats-officedocument.wordprocessingml.document
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 13.070432

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