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A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition

Polysaccharide conjugates are important renewable materials. If properly designed, they may for example be able to carry drugs, be proactive (e.g., with amino acid substituents) and can carry a charge. These aspects can be particularly useful for biomedical applications. Herein, we report a simple a...

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Detalles Bibliográficos
Autores principales: Chen, Junyi, Ma, Xutao, Edgar, Kevin J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8228737/
https://www.ncbi.nlm.nih.gov/pubmed/34201140
http://dx.doi.org/10.3390/polym13121905
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author Chen, Junyi
Ma, Xutao
Edgar, Kevin J.
author_facet Chen, Junyi
Ma, Xutao
Edgar, Kevin J.
author_sort Chen, Junyi
collection PubMed
description Polysaccharide conjugates are important renewable materials. If properly designed, they may for example be able to carry drugs, be proactive (e.g., with amino acid substituents) and can carry a charge. These aspects can be particularly useful for biomedical applications. Herein, we report a simple approach to preparing polysaccharide conjugates. Thiol-Michael additions can be mild, modular, and efficient, making them useful tools for post-modification and the tailoring of polysaccharide architecture. In this study, hydroxypropyl cellulose (HPC) and dextran (Dex) were modified by methacrylation. The resulting polysaccharide, bearing α,β-unsaturated esters with tunable DS (methacrylate), was reacted with various thiols, including 2-thioethylamine, cysteine, and thiol functional quaternary ammonium salt through thiol-Michael addition, affording functionalized conjugates. This click-like synthetic approach provided several advantages including a fast reaction rate, high conversion, and the use of water as a solvent. Among these polysaccharide conjugates, the ones bearing quaternary ammonium salts exhibited competitive antimicrobial performance, as supported by a minimum inhibitory concentration (MIC) study and tracked by SEM characterization. Overall, this methodology provides a versatile route to polysaccharide conjugates with diverse functionalities, enabling applications such as antimicrobial activity, gene or drug delivery, and biomimicry.
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spelling pubmed-82287372021-06-26 A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition Chen, Junyi Ma, Xutao Edgar, Kevin J. Polymers (Basel) Article Polysaccharide conjugates are important renewable materials. If properly designed, they may for example be able to carry drugs, be proactive (e.g., with amino acid substituents) and can carry a charge. These aspects can be particularly useful for biomedical applications. Herein, we report a simple approach to preparing polysaccharide conjugates. Thiol-Michael additions can be mild, modular, and efficient, making them useful tools for post-modification and the tailoring of polysaccharide architecture. In this study, hydroxypropyl cellulose (HPC) and dextran (Dex) were modified by methacrylation. The resulting polysaccharide, bearing α,β-unsaturated esters with tunable DS (methacrylate), was reacted with various thiols, including 2-thioethylamine, cysteine, and thiol functional quaternary ammonium salt through thiol-Michael addition, affording functionalized conjugates. This click-like synthetic approach provided several advantages including a fast reaction rate, high conversion, and the use of water as a solvent. Among these polysaccharide conjugates, the ones bearing quaternary ammonium salts exhibited competitive antimicrobial performance, as supported by a minimum inhibitory concentration (MIC) study and tracked by SEM characterization. Overall, this methodology provides a versatile route to polysaccharide conjugates with diverse functionalities, enabling applications such as antimicrobial activity, gene or drug delivery, and biomimicry. MDPI 2021-06-08 /pmc/articles/PMC8228737/ /pubmed/34201140 http://dx.doi.org/10.3390/polym13121905 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chen, Junyi
Ma, Xutao
Edgar, Kevin J.
A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
title A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
title_full A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
title_fullStr A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
title_full_unstemmed A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
title_short A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
title_sort versatile method for preparing polysaccharide conjugates via thiol-michael addition
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8228737/
https://www.ncbi.nlm.nih.gov/pubmed/34201140
http://dx.doi.org/10.3390/polym13121905
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