Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties
- Autores
- García Cambón, Tomás Agustín; Samaniego Lopez, Cecilia; Hanheiser, Natalie; Bhatia, Sumati; Achazi, Katharina; Rivas, Maria Veronica; Spagnuolo, Carla Cecilia
- Año de publicación
- 2023
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Boronated polymers are in the focus of dynamic functional materials due to the versatility of the B-O interactions and accessibility of precursors. Polysaccharides are highly biocompatible, and therefore, an attractive platform for anchoring boronic acid groups for further bioconjugation of cis-diol containing molecules. We report for the first time the introduction of benzoxaborole by amidation of the amino groups of chitosan improving solubility and introducing cis-diol recognition at physiological pH. The chemical structures and physical properties of the novel chitosan-benzoxaborole (CS-Bx) as well as two phenylboronic derivatives synthesized for comparison, were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), dynamic light scattering (DLS), rheology and optical spectroscopic methods. The novel benzoxaborole grafted chitosan was perfectly solubilized in an aqueous buffer at physiological pH, extending the possibilities of boronated materials derived from polysaccharides. The dynamic covalent interaction between boronated chitosan and model affinity ligands, was studied by means of spectroscopy methods. A glycopolymer derived from poly(isobutylene-alt-anhydride) was also synthesized to study the formation of dynamic assemblies with benzoxaborole-grafted chitosan. A first approximation to apply fluorescence microscale thermophoresis for the interactions of the modified polysaccharide is also discussed. Additionally, the activity of CSBx against bacterial adhesion was studied.
Fil: García Cambón, Tomás Agustín. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Samaniego Lopez, Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Hanheiser, Natalie. Freie Universität Berlin; Alemania
Fil: Bhatia, Sumati. Freie Universität Berlin; Alemania
Fil: Achazi, Katharina. Freie Universität Berlin; Alemania
Fil: Rivas, Maria Veronica. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Oficina de Coordinacion Administrativa Ciudad Universitaria. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia - Nodo Constituyentes | Comision Nacional de Energia Atomica. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia - Nodo Constituyentes.; Argentina
Fil: Spagnuolo, Carla Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina - Materia
-
BENZOXABOROLE
BORONIC ACID
CHITOSAN
COVALENT DYNAMIC INTERACTION - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/228431
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Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial propertiesGarcía Cambón, Tomás AgustínSamaniego Lopez, CeciliaHanheiser, NatalieBhatia, SumatiAchazi, KatharinaRivas, Maria VeronicaSpagnuolo, Carla CeciliaBENZOXABOROLEBORONIC ACIDCHITOSANCOVALENT DYNAMIC INTERACTIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Boronated polymers are in the focus of dynamic functional materials due to the versatility of the B-O interactions and accessibility of precursors. Polysaccharides are highly biocompatible, and therefore, an attractive platform for anchoring boronic acid groups for further bioconjugation of cis-diol containing molecules. We report for the first time the introduction of benzoxaborole by amidation of the amino groups of chitosan improving solubility and introducing cis-diol recognition at physiological pH. The chemical structures and physical properties of the novel chitosan-benzoxaborole (CS-Bx) as well as two phenylboronic derivatives synthesized for comparison, were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), dynamic light scattering (DLS), rheology and optical spectroscopic methods. The novel benzoxaborole grafted chitosan was perfectly solubilized in an aqueous buffer at physiological pH, extending the possibilities of boronated materials derived from polysaccharides. The dynamic covalent interaction between boronated chitosan and model affinity ligands, was studied by means of spectroscopy methods. A glycopolymer derived from poly(isobutylene-alt-anhydride) was also synthesized to study the formation of dynamic assemblies with benzoxaborole-grafted chitosan. A first approximation to apply fluorescence microscale thermophoresis for the interactions of the modified polysaccharide is also discussed. Additionally, the activity of CSBx against bacterial adhesion was studied.Fil: García Cambón, Tomás Agustín. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Samaniego Lopez, Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Hanheiser, Natalie. Freie Universität Berlin; AlemaniaFil: Bhatia, Sumati. Freie Universität Berlin; AlemaniaFil: Achazi, Katharina. Freie Universität Berlin; AlemaniaFil: Rivas, Maria Veronica. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Oficina de Coordinacion Administrativa Ciudad Universitaria. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia - Nodo Constituyentes | Comision Nacional de Energia Atomica. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia - Nodo Constituyentes.; ArgentinaFil: Spagnuolo, Carla Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaElsevier2023-04info: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/11336/228431García Cambón, Tomás Agustín; Samaniego Lopez, Cecilia; Hanheiser, Natalie; Bhatia, Sumati; Achazi, Katharina; et al.; Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties; Elsevier; Carbohydrate Polymers; 316; 4-2023; 1-350144-8617CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0144861723003909info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carbpol.2023.120925info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:45:35Zoai:ri.conicet.gov.ar:11336/228431instacron: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 10:45:35.556CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
title |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
spellingShingle |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties García Cambón, Tomás Agustín BENZOXABOROLE BORONIC ACID CHITOSAN COVALENT DYNAMIC INTERACTION |
title_short |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
title_full |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
title_fullStr |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
title_full_unstemmed |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
title_sort |
Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties |
dc.creator.none.fl_str_mv |
García Cambón, Tomás Agustín Samaniego Lopez, Cecilia Hanheiser, Natalie Bhatia, Sumati Achazi, Katharina Rivas, Maria Veronica Spagnuolo, Carla Cecilia |
author |
García Cambón, Tomás Agustín |
author_facet |
García Cambón, Tomás Agustín Samaniego Lopez, Cecilia Hanheiser, Natalie Bhatia, Sumati Achazi, Katharina Rivas, Maria Veronica Spagnuolo, Carla Cecilia |
author_role |
author |
author2 |
Samaniego Lopez, Cecilia Hanheiser, Natalie Bhatia, Sumati Achazi, Katharina Rivas, Maria Veronica Spagnuolo, Carla Cecilia |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
BENZOXABOROLE BORONIC ACID CHITOSAN COVALENT DYNAMIC INTERACTION |
topic |
BENZOXABOROLE BORONIC ACID CHITOSAN COVALENT DYNAMIC INTERACTION |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Boronated polymers are in the focus of dynamic functional materials due to the versatility of the B-O interactions and accessibility of precursors. Polysaccharides are highly biocompatible, and therefore, an attractive platform for anchoring boronic acid groups for further bioconjugation of cis-diol containing molecules. We report for the first time the introduction of benzoxaborole by amidation of the amino groups of chitosan improving solubility and introducing cis-diol recognition at physiological pH. The chemical structures and physical properties of the novel chitosan-benzoxaborole (CS-Bx) as well as two phenylboronic derivatives synthesized for comparison, were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), dynamic light scattering (DLS), rheology and optical spectroscopic methods. The novel benzoxaborole grafted chitosan was perfectly solubilized in an aqueous buffer at physiological pH, extending the possibilities of boronated materials derived from polysaccharides. The dynamic covalent interaction between boronated chitosan and model affinity ligands, was studied by means of spectroscopy methods. A glycopolymer derived from poly(isobutylene-alt-anhydride) was also synthesized to study the formation of dynamic assemblies with benzoxaborole-grafted chitosan. A first approximation to apply fluorescence microscale thermophoresis for the interactions of the modified polysaccharide is also discussed. Additionally, the activity of CSBx against bacterial adhesion was studied. Fil: García Cambón, Tomás Agustín. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina Fil: Samaniego Lopez, Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina Fil: Hanheiser, Natalie. Freie Universität Berlin; Alemania Fil: Bhatia, Sumati. Freie Universität Berlin; Alemania Fil: Achazi, Katharina. Freie Universität Berlin; Alemania Fil: Rivas, Maria Veronica. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Oficina de Coordinacion Administrativa Ciudad Universitaria. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia - Nodo Constituyentes | Comision Nacional de Energia Atomica. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia. Unidad Ejecutora Instituto de Nanociencia y Nanotecnologia - Nodo Constituyentes.; Argentina Fil: Spagnuolo, Carla Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina |
description |
Boronated polymers are in the focus of dynamic functional materials due to the versatility of the B-O interactions and accessibility of precursors. Polysaccharides are highly biocompatible, and therefore, an attractive platform for anchoring boronic acid groups for further bioconjugation of cis-diol containing molecules. We report for the first time the introduction of benzoxaborole by amidation of the amino groups of chitosan improving solubility and introducing cis-diol recognition at physiological pH. The chemical structures and physical properties of the novel chitosan-benzoxaborole (CS-Bx) as well as two phenylboronic derivatives synthesized for comparison, were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), dynamic light scattering (DLS), rheology and optical spectroscopic methods. The novel benzoxaborole grafted chitosan was perfectly solubilized in an aqueous buffer at physiological pH, extending the possibilities of boronated materials derived from polysaccharides. The dynamic covalent interaction between boronated chitosan and model affinity ligands, was studied by means of spectroscopy methods. A glycopolymer derived from poly(isobutylene-alt-anhydride) was also synthesized to study the formation of dynamic assemblies with benzoxaborole-grafted chitosan. A first approximation to apply fluorescence microscale thermophoresis for the interactions of the modified polysaccharide is also discussed. Additionally, the activity of CSBx against bacterial adhesion was studied. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-04 |
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/11336/228431 García Cambón, Tomás Agustín; Samaniego Lopez, Cecilia; Hanheiser, Natalie; Bhatia, Sumati; Achazi, Katharina; et al.; Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties; Elsevier; Carbohydrate Polymers; 316; 4-2023; 1-35 0144-8617 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/228431 |
identifier_str_mv |
García Cambón, Tomás Agustín; Samaniego Lopez, Cecilia; Hanheiser, Natalie; Bhatia, Sumati; Achazi, Katharina; et al.; Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties; Elsevier; Carbohydrate Polymers; 316; 4-2023; 1-35 0144-8617 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/S0144861723003909 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carbpol.2023.120925 |
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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1844614495804063744 |
score |
13.070432 |