Synthesis and characterization of a β-CD-alginate conjugate

Autores
Gomez, Cesar Gerardo; Chambat, Gérard; Hayraud, Alain; Villar, Marcelo Armando; Auzély Velty, Rachel
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Selective chemical modification of both β-cyclodextrin (β-CD) and sodium alginate (alg) was performed in order to produce an alginate derivative possessing pendant β-CD cavities along the chain. The latter was then fully characterized in terms of chemical integrity and purity, complexation properties and ability to form hydrogels. Thus, a sodium alginate derivative modified with adipic dihydrazide (alg-ADH) and a β-cyclodextrin derivative possessing an aldehyde function on the primary face were synthesized, and both were selectively coupled by a reductive amination-type reaction. Comparison of the complexation properties of the grafted and natural β-CDs by isothermal titration calorimetry using sodium adamantane acetate as a model guest gave similar enthalpy values suggesting similar mechanisms of binding. However, the association constant for the grafted CD is slightly lower as a result of a less favorable change in the binding entropy. Investigation of the gelation ability in the presence of calcium ions led to the following order: alg > alg-ADH > alg-CD. The decrease of gelation efficiency for the modified alginate samples reflected the reduction of ionic interchain bonds as a result of the unavailability or non-accessibility of G units on the alginate backbone, due to the chemical modification and steric effect of the CD molecule for alg-CD.
Fil: Gomez, Cesar Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Chambat, Gérard. Universite Joseph Fourier; Francia
Fil: Hayraud, Alain. Universite Joseph Fourier; Francia
Fil: Villar, Marcelo Armando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Auzély Velty, Rachel. Universite Joseph Fourier; Francia
Materia
Alginate
Cyclodextrin
Hydrogel
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/79067
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/79067
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and characterization of a β-CD-alginate conjugateGomez, Cesar GerardoChambat, GérardHayraud, AlainVillar, Marcelo ArmandoAuzély Velty, RachelAlginateCyclodextrinHydrogelhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Selective chemical modification of both β-cyclodextrin (β-CD) and sodium alginate (alg) was performed in order to produce an alginate derivative possessing pendant β-CD cavities along the chain. The latter was then fully characterized in terms of chemical integrity and purity, complexation properties and ability to form hydrogels. Thus, a sodium alginate derivative modified with adipic dihydrazide (alg-ADH) and a β-cyclodextrin derivative possessing an aldehyde function on the primary face were synthesized, and both were selectively coupled by a reductive amination-type reaction. Comparison of the complexation properties of the grafted and natural β-CDs by isothermal titration calorimetry using sodium adamantane acetate as a model guest gave similar enthalpy values suggesting similar mechanisms of binding. However, the association constant for the grafted CD is slightly lower as a result of a less favorable change in the binding entropy. Investigation of the gelation ability in the presence of calcium ions led to the following order: alg > alg-ADH > alg-CD. The decrease of gelation efficiency for the modified alginate samples reflected the reduction of ionic interchain bonds as a result of the unavailability or non-accessibility of G units on the alginate backbone, due to the chemical modification and steric effect of the CD molecule for alg-CD.Fil: Gomez, Cesar Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Chambat, Gérard. Universite Joseph Fourier; FranciaFil: Hayraud, Alain. Universite Joseph Fourier; FranciaFil: Villar, Marcelo Armando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Auzély Velty, Rachel. Universite Joseph Fourier; FranciaElsevier2006-12-07info: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/11336/79067Gomez, Cesar Gerardo; Chambat, Gérard; Hayraud, Alain; Villar, Marcelo Armando; Auzély Velty, Rachel; Synthesis and characterization of a β-CD-alginate conjugate; Elsevier; Polymer; 47; 26; 7-12-2006; 8509-85160032-3861CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0032386106011736info:eu-repo/semantics/altIdentifier/doi/10.1016/j.polymer.2006.10.011info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T10:29:15Zoai:ri.conicet.gov.ar:11336/79067instacron: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:34982025-11-05 10:29:15.326CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and characterization of a β-CD-alginate conjugate
title Synthesis and characterization of a β-CD-alginate conjugate
spellingShingle Synthesis and characterization of a β-CD-alginate conjugate
Gomez, Cesar Gerardo
Alginate
Cyclodextrin
Hydrogel
title_short Synthesis and characterization of a β-CD-alginate conjugate
title_full Synthesis and characterization of a β-CD-alginate conjugate
title_fullStr Synthesis and characterization of a β-CD-alginate conjugate
title_full_unstemmed Synthesis and characterization of a β-CD-alginate conjugate
title_sort Synthesis and characterization of a β-CD-alginate conjugate
dc.creator.none.fl_str_mv Gomez, Cesar Gerardo
Chambat, Gérard
Hayraud, Alain
Villar, Marcelo Armando
Auzély Velty, Rachel
author Gomez, Cesar Gerardo
author_facet Gomez, Cesar Gerardo
Chambat, Gérard
Hayraud, Alain
Villar, Marcelo Armando
Auzély Velty, Rachel
author_role author
author2 Chambat, Gérard
Hayraud, Alain
Villar, Marcelo Armando
Auzély Velty, Rachel
author2_role author
author
author
author
dc.subject.none.fl_str_mv Alginate
Cyclodextrin
Hydrogel
topic Alginate
Cyclodextrin
Hydrogel
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Selective chemical modification of both β-cyclodextrin (β-CD) and sodium alginate (alg) was performed in order to produce an alginate derivative possessing pendant β-CD cavities along the chain. The latter was then fully characterized in terms of chemical integrity and purity, complexation properties and ability to form hydrogels. Thus, a sodium alginate derivative modified with adipic dihydrazide (alg-ADH) and a β-cyclodextrin derivative possessing an aldehyde function on the primary face were synthesized, and both were selectively coupled by a reductive amination-type reaction. Comparison of the complexation properties of the grafted and natural β-CDs by isothermal titration calorimetry using sodium adamantane acetate as a model guest gave similar enthalpy values suggesting similar mechanisms of binding. However, the association constant for the grafted CD is slightly lower as a result of a less favorable change in the binding entropy. Investigation of the gelation ability in the presence of calcium ions led to the following order: alg > alg-ADH > alg-CD. The decrease of gelation efficiency for the modified alginate samples reflected the reduction of ionic interchain bonds as a result of the unavailability or non-accessibility of G units on the alginate backbone, due to the chemical modification and steric effect of the CD molecule for alg-CD.
Fil: Gomez, Cesar Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Chambat, Gérard. Universite Joseph Fourier; Francia
Fil: Hayraud, Alain. Universite Joseph Fourier; Francia
Fil: Villar, Marcelo Armando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Auzély Velty, Rachel. Universite Joseph Fourier; Francia
description Selective chemical modification of both β-cyclodextrin (β-CD) and sodium alginate (alg) was performed in order to produce an alginate derivative possessing pendant β-CD cavities along the chain. The latter was then fully characterized in terms of chemical integrity and purity, complexation properties and ability to form hydrogels. Thus, a sodium alginate derivative modified with adipic dihydrazide (alg-ADH) and a β-cyclodextrin derivative possessing an aldehyde function on the primary face were synthesized, and both were selectively coupled by a reductive amination-type reaction. Comparison of the complexation properties of the grafted and natural β-CDs by isothermal titration calorimetry using sodium adamantane acetate as a model guest gave similar enthalpy values suggesting similar mechanisms of binding. However, the association constant for the grafted CD is slightly lower as a result of a less favorable change in the binding entropy. Investigation of the gelation ability in the presence of calcium ions led to the following order: alg > alg-ADH > alg-CD. The decrease of gelation efficiency for the modified alginate samples reflected the reduction of ionic interchain bonds as a result of the unavailability or non-accessibility of G units on the alginate backbone, due to the chemical modification and steric effect of the CD molecule for alg-CD.
publishDate 2006
dc.date.none.fl_str_mv 2006-12-07
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/11336/79067
Gomez, Cesar Gerardo; Chambat, Gérard; Hayraud, Alain; Villar, Marcelo Armando; Auzély Velty, Rachel; Synthesis and characterization of a β-CD-alginate conjugate; Elsevier; Polymer; 47; 26; 7-12-2006; 8509-8516
0032-3861
CONICET Digital
CONICET
url http://hdl.handle.net/11336/79067
identifier_str_mv Gomez, Cesar Gerardo; Chambat, Gérard; Hayraud, Alain; Villar, Marcelo Armando; Auzély Velty, Rachel; Synthesis and characterization of a β-CD-alginate conjugate; Elsevier; Polymer; 47; 26; 7-12-2006; 8509-8516
0032-3861
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0032386106011736
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.polymer.2006.10.011
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
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 13.087074

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