Issue 47, 2023

Dual functional quaternary chitosans with thermoresponsive behavior: structure–activity relationships in antibacterial activity and biocompatibility

Abstract

Cationically modified chitosan derivatives exhibit a range of appealing characteristics, with a particular emphasis on their antimicrobial potential across a broad spectrum of biomedical applications. This study aimed to delve deeper into quaternary chitosan (QC) derivatives. Through the synthesis of both homogeneously and heterogeneously dual-quaternized chitosan (DQC), utilizing AETMAC ([2-(acryloyloxy)ethyl]-trimethylammonium chloride) and GTMAC (glycidyl trimethylammonium chloride), a permanent charge was established, spanning a wide pH range. We assessed structural differences, the type of quaternary functional group, molecular weight (Mw), and charge density. Intriguingly, an upper critical solution temperature (UCST) behavior was observed in AETMAC-functionalized QC. To our knowledge, it is a novel discovery in cationically functionalized chitosan. These materials demonstrated excellent antimicrobial efficacy against model test organisms E. coli and P. syringae. Furthermore, we detected concentration-dependent cytotoxicity in NIH-3T3 fibroblasts. Striking a balance between antimicrobial activity and cytotoxicity becomes a crucial factor in application feasibility. AETMAC-functionalized chitosan emerges as the top performer in terms of overall antibacterial effectiveness, possibly owing to factors like molecular weight, charge characteristics, and variations in the quaternary linker. Quaternary chitosan derivatives, with their excellent antibacterial attributes, hold significant promise as antibacterial or sanitizing agents, as well as across a broad spectrum of biomedical and environmental contexts.

Graphical abstract: Dual functional quaternary chitosans with thermoresponsive behavior: structure–activity relationships in antibacterial activity and biocompatibility

Supplementary files

Article information

Article type
Paper
Submitted
05 Sep 2023
Accepted
07 Nov 2023
First published
13 Nov 2023
This article is Open Access
Creative Commons BY license

J. Mater. Chem. B, 2023,11, 11300-11309

Dual functional quaternary chitosans with thermoresponsive behavior: structure–activity relationships in antibacterial activity and biocompatibility

S. Borandeh, I. Laurén, A. Teotia, J. Niskanen and J. Seppälä, J. Mater. Chem. B, 2023, 11, 11300 DOI: 10.1039/D3TB02066E

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