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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/226767
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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 |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=D3PY00347G 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 |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc/2.5/ar/ |
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 |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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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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1844613853233545216 |
score |
13.070432 |