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Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties

Tomás A. García Cambón, Cecilia Samaniego Lopez, Natalie Hanheiser, Sumati Bhatia Orcid Logo, Katharina Achazi, M. Verónica Rivas, Carla C. Spagnuolo

Carbohydrate Polymers, Volume: 316, Start page: 120925

Swansea University Author: Sumati Bhatia Orcid Logo

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DOI (Published version): 10.1016/j.carbpol.2023.120925

Abstract

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...

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Published in: Carbohydrate Polymers
ISSN: 0144-8617
Published: Elsevier BV 2023
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URI: https://cronfa.swan.ac.uk/Record/cronfa64892
first_indexed 2023-11-08T12:08:32Z
last_indexed 2024-11-25T14:14:56Z
id cronfa64892
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spelling 2023-12-21T15:12:55.1727954 v2 64892 2023-11-01 Benzoxaborole-grafted high molecular weight chitosan from prawn: Synthesis, characterization, target recognition and antibacterial properties a6b1181ebdbe42bd03b24cbdb559d082 0000-0002-5123-4937 Sumati Bhatia Sumati Bhatia true false 2023-11-01 EAAS 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. Journal Article Carbohydrate Polymers 316 120925 Elsevier BV 0144-8617 15 9 2023 2023-09-15 10.1016/j.carbpol.2023.120925 http://dx.doi.org/10.1016/j.carbpol.2023.120925 COLLEGE NANME Engineering and Applied Sciences School COLLEGE CODE EAAS Swansea University 2023-12-21T15:12:55.1727954 2023-11-01T10:49:35.5873594 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Tomás A. García Cambón 1 Cecilia Samaniego Lopez 2 Natalie Hanheiser 3 Sumati Bhatia 0000-0002-5123-4937 4 Katharina Achazi 5 M. Verónica Rivas 6 Carla C. Spagnuolo 7
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
Sumati Bhatia
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
author_id_str_mv a6b1181ebdbe42bd03b24cbdb559d082
author_id_fullname_str_mv a6b1181ebdbe42bd03b24cbdb559d082_***_Sumati Bhatia
author Sumati Bhatia
author2 Tomás A. García Cambón
Cecilia Samaniego Lopez
Natalie Hanheiser
Sumati Bhatia
Katharina Achazi
M. Verónica Rivas
Carla C. Spagnuolo
format Journal article
container_title Carbohydrate Polymers
container_volume 316
container_start_page 120925
publishDate 2023
institution Swansea University
issn 0144-8617
doi_str_mv 10.1016/j.carbpol.2023.120925
publisher Elsevier BV
college_str Faculty of Science and Engineering
hierarchytype
hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
url http://dx.doi.org/10.1016/j.carbpol.2023.120925
document_store_str 0
active_str 0
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.
published_date 2023-09-15T14:28:51Z
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score 11.048042

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