Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups

Autores
Wolfel Sánchez, Alexis; Wang, Huiyi; Osorio Blanco, Ernesto Rafael; Bergueiro, Julian; Romero, Marcelo Ricardo; Alvarez Igarzabal, Cecilia Ines; Calderón, Marcelo
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Advancements in nanogel (NG) applications require precise control over their size, structure, and functionalization. However, synthesis methods have limitations that hinder the incorporation of some functional groups and hamper the architectural control over NGs. In this work, we developed a facile post-synthesis reaction strategy to modify the structure and functionalization of thermoresponsive NGs. Specifically, we studied the incorporation of a cleavable crosslinker, (+)-N,N′-diallyltartardiamide (DAT), in the synthesis of poly(N-isopropylacrylamide) (p-NIPAm), poly(N-isopropylmethacrylamide) (p-NIPMAm), and p-NIPAm-co-NIPMAm-based NGs. The efficient cleavage of DAT-crosslinks by sodium periodate enables control over the crosslinking degree and architecture of the NGs. This cleavage reaction also introduces alpha-oxoaldehydes (glyoxylic groups), which can be used for subsequent bio-conjugation under mild conditions. The incorporation of DAT-crosslinks in the NG architecture is governed by the reactivity of monomers and crosslinkers, as well as the initiation method used. Consequently, the structural changes caused by the cleavage of DAT-crosslinks depend on the composition and synthesis parameters, providing a valuable tool for fine-tuning drug delivery nanodevices in a post-synthetic step. As proof of concept, we demonstrated that the cleavage of DAT-crosslinks increased the loading efficiency of bovine serum albumin, a macromolecular drug surrogate. Additionally, we used the obtained alpha-oxoaldehydes to covalently link doxorubicin (DOXO) through hydrazone bonds, introducing pH-selective drug release.
Fil: Wolfel Sánchez, Alexis. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Wang, Huiyi. Universidad del Pais Vasco. Polymat.; España
Fil: Osorio Blanco, Ernesto Rafael. Universidad del Pais Vasco. Polymat.; España
Fil: Bergueiro, Julian. Universidad de Santiago de Compostela. Facultad de Química; España
Fil: Romero, Marcelo Ricardo. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Alvarez Igarzabal, Cecilia Ines. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Calderón, Marcelo. Universidad del Pais Vasco. Polymat.; España
Materia
NANOGEL
THERMORESPONSIVE
CROSS-LINKING
DRUG DELIVERY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/226767

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network_name_str CONICET Digital (CONICET)
spelling Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groupsWolfel Sánchez, AlexisWang, HuiyiOsorio Blanco, Ernesto RafaelBergueiro, JulianRomero, Marcelo RicardoAlvarez Igarzabal, Cecilia InesCalderón, MarceloNANOGELTHERMORESPONSIVECROSS-LINKINGDRUG DELIVERYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Advancements in nanogel (NG) applications require precise control over their size, structure, and functionalization. However, synthesis methods have limitations that hinder the incorporation of some functional groups and hamper the architectural control over NGs. In this work, we developed a facile post-synthesis reaction strategy to modify the structure and functionalization of thermoresponsive NGs. Specifically, we studied the incorporation of a cleavable crosslinker, (+)-N,N′-diallyltartardiamide (DAT), in the synthesis of poly(N-isopropylacrylamide) (p-NIPAm), poly(N-isopropylmethacrylamide) (p-NIPMAm), and p-NIPAm-co-NIPMAm-based NGs. The efficient cleavage of DAT-crosslinks by sodium periodate enables control over the crosslinking degree and architecture of the NGs. This cleavage reaction also introduces alpha-oxoaldehydes (glyoxylic groups), which can be used for subsequent bio-conjugation under mild conditions. The incorporation of DAT-crosslinks in the NG architecture is governed by the reactivity of monomers and crosslinkers, as well as the initiation method used. Consequently, the structural changes caused by the cleavage of DAT-crosslinks depend on the composition and synthesis parameters, providing a valuable tool for fine-tuning drug delivery nanodevices in a post-synthetic step. As proof of concept, we demonstrated that the cleavage of DAT-crosslinks increased the loading efficiency of bovine serum albumin, a macromolecular drug surrogate. Additionally, we used the obtained alpha-oxoaldehydes to covalently link doxorubicin (DOXO) through hydrazone bonds, introducing pH-selective drug release.Fil: Wolfel Sánchez, Alexis. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; ArgentinaFil: Wang, Huiyi. Universidad del Pais Vasco. Polymat.; EspañaFil: Osorio Blanco, Ernesto Rafael. Universidad del Pais Vasco. Polymat.; EspañaFil: Bergueiro, Julian. Universidad de Santiago de Compostela. Facultad de Química; EspañaFil: Romero, Marcelo Ricardo. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Alvarez Igarzabal, Cecilia Ines. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; ArgentinaFil: Calderón, Marcelo. Universidad del Pais Vasco. Polymat.; EspañaRoyal Society of Chemistry2023-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documentapplication/pdfhttp://hdl.handle.net/11336/226767Wolfel Sánchez, Alexis; Wang, Huiyi; Osorio Blanco, Ernesto Rafael; Bergueiro, Julian; Romero, Marcelo Ricardo; et al.; Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups; Royal Society of Chemistry; Polymer Chemistry; 14; 25; 6-2023; 2998-30071759-99541759-9962CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=D3PY00347Ginfo:eu-repo/semantics/altIdentifier/doi/10.1039/D3PY00347Ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:03:33Zoai:ri.conicet.gov.ar:11336/226767instacron: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 10:03:33.643CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
title Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
spellingShingle Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
Wolfel Sánchez, Alexis
NANOGEL
THERMORESPONSIVE
CROSS-LINKING
DRUG DELIVERY
title_short Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
title_full Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
title_fullStr Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
title_full_unstemmed Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
title_sort Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups
dc.creator.none.fl_str_mv Wolfel Sánchez, Alexis
Wang, Huiyi
Osorio Blanco, Ernesto Rafael
Bergueiro, Julian
Romero, Marcelo Ricardo
Alvarez Igarzabal, Cecilia Ines
Calderón, Marcelo
author Wolfel Sánchez, Alexis
author_facet Wolfel Sánchez, Alexis
Wang, Huiyi
Osorio Blanco, Ernesto Rafael
Bergueiro, Julian
Romero, Marcelo Ricardo
Alvarez Igarzabal, Cecilia Ines
Calderón, Marcelo
author_role author
author2 Wang, Huiyi
Osorio Blanco, Ernesto Rafael
Bergueiro, Julian
Romero, Marcelo Ricardo
Alvarez Igarzabal, Cecilia Ines
Calderón, Marcelo
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv NANOGEL
THERMORESPONSIVE
CROSS-LINKING
DRUG DELIVERY
topic NANOGEL
THERMORESPONSIVE
CROSS-LINKING
DRUG DELIVERY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Advancements in nanogel (NG) applications require precise control over their size, structure, and functionalization. However, synthesis methods have limitations that hinder the incorporation of some functional groups and hamper the architectural control over NGs. In this work, we developed a facile post-synthesis reaction strategy to modify the structure and functionalization of thermoresponsive NGs. Specifically, we studied the incorporation of a cleavable crosslinker, (+)-N,N′-diallyltartardiamide (DAT), in the synthesis of poly(N-isopropylacrylamide) (p-NIPAm), poly(N-isopropylmethacrylamide) (p-NIPMAm), and p-NIPAm-co-NIPMAm-based NGs. The efficient cleavage of DAT-crosslinks by sodium periodate enables control over the crosslinking degree and architecture of the NGs. This cleavage reaction also introduces alpha-oxoaldehydes (glyoxylic groups), which can be used for subsequent bio-conjugation under mild conditions. The incorporation of DAT-crosslinks in the NG architecture is governed by the reactivity of monomers and crosslinkers, as well as the initiation method used. Consequently, the structural changes caused by the cleavage of DAT-crosslinks depend on the composition and synthesis parameters, providing a valuable tool for fine-tuning drug delivery nanodevices in a post-synthetic step. As proof of concept, we demonstrated that the cleavage of DAT-crosslinks increased the loading efficiency of bovine serum albumin, a macromolecular drug surrogate. Additionally, we used the obtained alpha-oxoaldehydes to covalently link doxorubicin (DOXO) through hydrazone bonds, introducing pH-selective drug release.
Fil: Wolfel Sánchez, Alexis. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Wang, Huiyi. Universidad del Pais Vasco. Polymat.; España
Fil: Osorio Blanco, Ernesto Rafael. Universidad del Pais Vasco. Polymat.; España
Fil: Bergueiro, Julian. Universidad de Santiago de Compostela. Facultad de Química; España
Fil: Romero, Marcelo Ricardo. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Alvarez Igarzabal, Cecilia Ines. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Calderón, Marcelo. Universidad del Pais Vasco. Polymat.; España
description Advancements in nanogel (NG) applications require precise control over their size, structure, and functionalization. However, synthesis methods have limitations that hinder the incorporation of some functional groups and hamper the architectural control over NGs. In this work, we developed a facile post-synthesis reaction strategy to modify the structure and functionalization of thermoresponsive NGs. Specifically, we studied the incorporation of a cleavable crosslinker, (+)-N,N′-diallyltartardiamide (DAT), in the synthesis of poly(N-isopropylacrylamide) (p-NIPAm), poly(N-isopropylmethacrylamide) (p-NIPMAm), and p-NIPAm-co-NIPMAm-based NGs. The efficient cleavage of DAT-crosslinks by sodium periodate enables control over the crosslinking degree and architecture of the NGs. This cleavage reaction also introduces alpha-oxoaldehydes (glyoxylic groups), which can be used for subsequent bio-conjugation under mild conditions. The incorporation of DAT-crosslinks in the NG architecture is governed by the reactivity of monomers and crosslinkers, as well as the initiation method used. Consequently, the structural changes caused by the cleavage of DAT-crosslinks depend on the composition and synthesis parameters, providing a valuable tool for fine-tuning drug delivery nanodevices in a post-synthetic step. As proof of concept, we demonstrated that the cleavage of DAT-crosslinks increased the loading efficiency of bovine serum albumin, a macromolecular drug surrogate. Additionally, we used the obtained alpha-oxoaldehydes to covalently link doxorubicin (DOXO) through hydrazone bonds, introducing pH-selective drug release.
publishDate 2023
dc.date.none.fl_str_mv 2023-06
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/11336/226767
Wolfel Sánchez, Alexis; Wang, Huiyi; Osorio Blanco, Ernesto Rafael; Bergueiro, Julian; Romero, Marcelo Ricardo; et al.; Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups; Royal Society of Chemistry; Polymer Chemistry; 14; 25; 6-2023; 2998-3007
1759-9954
1759-9962
CONICET Digital
CONICET
url http://hdl.handle.net/11336/226767
identifier_str_mv Wolfel Sánchez, Alexis; Wang, Huiyi; Osorio Blanco, Ernesto Rafael; Bergueiro, Julian; Romero, Marcelo Ricardo; et al.; Structural control and functionalization of thermoresponsive nanogels: turning cross-linking points into anchoring groups; Royal Society of Chemistry; Polymer Chemistry; 14; 25; 6-2023; 2998-3007
1759-9954
1759-9962
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
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info:eu-repo/semantics/altIdentifier/doi/10.1039/D3PY00347G
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
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dc.format.none.fl_str_mv application/pdf
application/vnd.openxmlformats-officedocument.wordprocessingml.document
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
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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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