Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides

Amphiphilic amino acid derived compounds are very interesting for the design of building blocks able to self-assemble into highly ordered nanostructures, in a hierarchical and controlled fashion. With this aim, the modular synthesis and the full characterization of simple Gemini Amphiphilic Pseudope...

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Detalles Bibliográficos
Autores: Rubio, Jenifer, Alfonso, Ignacio, Burguete, M. Isabel, Luis, Santiago V.
Tipo de recurso: artículo
Fecha de publicación:2011
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/53507
Acceso en línea:http://hdl.handle.net/10261/53507
Access Level:acceso abierto
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spelling Stimulus responsive self-assembly of Gemini Amphiphilic PseudopeptidesRubio, JeniferAlfonso, IgnacioBurguete, M. IsabelLuis, Santiago V.Amphiphilic amino acid derived compounds are very interesting for the design of building blocks able to self-assemble into highly ordered nanostructures, in a hierarchical and controlled fashion. With this aim, the modular synthesis and the full characterization of simple Gemini Amphiphilic Pseudopeptides (GAPs) have been carried out. These compounds were designed to establish intermolecular interactions in a hierarchical way to finally render supramolecular assemblies into well-ordered nanostructures, such as fibers, tubes, tapes or spherical vesicles. Different structural variables have been implemented, such as the amino acid side chain, the length of the central spacer and the nature of the hydrophobic tails. Besides, the effect of the environment was systematically checked, by performing the studies in solvents of different polarities (chloroform, methanol or aqueous methanol) and at different pHs (neutral, basic and acidic). The non-covalent self-assembling abilities and the structural features of the GAPs have been studied in the solid (SEM, TEM and FT-IR) and in the solution states (NMR, UV, CD, FT-IR and fluorescence spectroscopy). Moreover, the connection between the solution and the solid states has been established by monitoring the slow evaporation of the solvent by ATR FT-IR. This study has allowed the establishment of a relationship between the chemical structures of the GAPs and their abilities to form nanostructures. In some optimal cases (especially for the valine derivatives with medium-length spacers and two decyloxybenzyl hydrophobic tails), they behaved as stimulus responsive self-assembling nano-structures, which form amorphous materials from non-polar solvents, nano-fibers from polar environments at neutral or basic pH and vesicles when become protonated at acidic pH values. A reasonable structural model to explain the experimental observations can be proposed through the combination of the results from the different techniques.This work was supported by the Spanish Ministry of Science and Innovation (CTQ2009-14366-C02) and UJI-Bancaixa (P1-1B- 2009-59). J.R. thanks MICINN for personal financial support(FPU fellowship). The support of the SCIC of the UJI for the different instrumental techniques is acknowledged.Peer reviewedRoyal Society of Chemistry (UK)201220122011info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/53507reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1039/C1SM06435Einfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/535072026-05-22T06:33:51Z
dc.title.none.fl_str_mv Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
title Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
spellingShingle Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
Rubio, Jenifer
title_short Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
title_full Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
title_fullStr Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
title_full_unstemmed Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
title_sort Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides
dc.creator.none.fl_str_mv Rubio, Jenifer
Alfonso, Ignacio
Burguete, M. Isabel
Luis, Santiago V.
author Rubio, Jenifer
author_facet Rubio, Jenifer
Alfonso, Ignacio
Burguete, M. Isabel
Luis, Santiago V.
author_role author
author2 Alfonso, Ignacio
Burguete, M. Isabel
Luis, Santiago V.
author2_role author
author
author
description Amphiphilic amino acid derived compounds are very interesting for the design of building blocks able to self-assemble into highly ordered nanostructures, in a hierarchical and controlled fashion. With this aim, the modular synthesis and the full characterization of simple Gemini Amphiphilic Pseudopeptides (GAPs) have been carried out. These compounds were designed to establish intermolecular interactions in a hierarchical way to finally render supramolecular assemblies into well-ordered nanostructures, such as fibers, tubes, tapes or spherical vesicles. Different structural variables have been implemented, such as the amino acid side chain, the length of the central spacer and the nature of the hydrophobic tails. Besides, the effect of the environment was systematically checked, by performing the studies in solvents of different polarities (chloroform, methanol or aqueous methanol) and at different pHs (neutral, basic and acidic). The non-covalent self-assembling abilities and the structural features of the GAPs have been studied in the solid (SEM, TEM and FT-IR) and in the solution states (NMR, UV, CD, FT-IR and fluorescence spectroscopy). Moreover, the connection between the solution and the solid states has been established by monitoring the slow evaporation of the solvent by ATR FT-IR. This study has allowed the establishment of a relationship between the chemical structures of the GAPs and their abilities to form nanostructures. In some optimal cases (especially for the valine derivatives with medium-length spacers and two decyloxybenzyl hydrophobic tails), they behaved as stimulus responsive self-assembling nano-structures, which form amorphous materials from non-polar solvents, nano-fibers from polar environments at neutral or basic pH and vesicles when become protonated at acidic pH values. A reasonable structural model to explain the experimental observations can be proposed through the combination of the results from the different techniques.
publishDate 2011
dc.date.none.fl_str_mv 2011
2012
2012
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
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dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/53507
url http://hdl.handle.net/10261/53507
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1039/C1SM06435E
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Royal Society of Chemistry (UK)
publisher.none.fl_str_mv Royal Society of Chemistry (UK)
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
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repository.mail.fl_str_mv
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