A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition
| dc.contributor.author | Chen, Junyi | en |
| dc.contributor.author | Ma, Xutao | en |
| dc.contributor.author | Edgar, Kevin J. | en |
| dc.contributor.department | Sustainable Biomaterials | en |
| dc.date.accessioned | 2021-06-10T19:36:48Z | en |
| dc.date.available | 2021-06-10T19:36:48Z | en |
| dc.date.issued | 2021-06-08 | en |
| dc.date.updated | 2021-06-10T13:47:33Z | en |
| dc.description.abstract | 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. | en |
| dc.description.version | Published version | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.citation | Chen, J.; Ma, X.; Edgar, K.J. A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition. Polymers 2021, 13, 1905. | en |
| dc.identifier.doi | https://doi.org/10.3390/polym13121905 | en |
| dc.identifier.uri | http://hdl.handle.net/10919/103768 | en |
| dc.language.iso | en | en |
| dc.publisher | MDPI | en |
| dc.rights | Creative Commons Attribution 4.0 International | en |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | en |
| dc.subject | polysaccharide chemical modification | en |
| dc.subject | thiol-Michael addition | en |
| dc.subject | cationic polysaccharide | en |
| dc.title | A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition | en |
| dc.title.serial | Polymers | en |
| dc.type | Article - Refereed | en |
| dc.type.dcmitype | Text | en |
| dc.type.dcmitype | StillImage | en |