Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand.
Program in Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Phayathai Road, Pathumwan, Bangkok 10330, Thailand.
Carbohydr Polym. 2022 Feb 1;277:118882. doi: 10.1016/j.carbpol.2021.118882. Epub 2021 Nov 10.
Hydrophobized chitosan derivatives, hexyl chitosan (HCS), dodecyl chitosan (DCS), and phthaloyl chitosan (PhCS) of approximately 30 and 50% degree of substitution (%DS) reacted with glycidyltrimethylammonium chloride (GTMAC) to incorporate hydrophilic positively charged groups of N-[(2-hydroxyl-3-trimethylammonium)propyl] and yielded amphiphilic quaternized chitosan derivatives. They can assemble into spherical nanoparticles with a hydrodynamic diameter of ~100-300 nm and positive ζ-potential values (+15 to +56). Their anti-biofilm efficacy was evaluated against the dental caries pathogen, Streptococcus mutans. Among all derivatives, the one having 30%DS of hexyl group and prepared by reacting with 1 mol equivalent of GTMAC (HCS-GTMAC) showed the best performance in terms of its aqueous solubility, the lowest minimum inhibitory concentration (138 μg/mL) and the minimum bactericidal concentration (275 μg/mL) which are superior to the unmodified chitosan. Its equivalent anti-biofilm efficacy to that of chlorhexidine suggests that it can be a greener antibacterial agent for oral care formulations.
疏水性壳聚糖衍生物，己基壳聚糖（HCS）、十二烷基壳聚糖（DCS）和邻苯二甲酰壳聚糖（PhCS）的取代度约为 30%和 50%（%DS），与缩水甘油三甲基氯化铵（GTMAC）反应，引入亲水性带正电荷的 N-[[2-羟基-3-三甲基铵]丙基]基团，得到两亲性季铵化壳聚糖衍生物。它们可以自组装成水动力直径约为 100-300nm 的球形纳米颗粒，并带有正 ζ-电位值（+15 至+56）。它们的抗生物膜功效针对龋齿病原体变形链球菌进行了评估。在所有衍生物中，用 1 摩尔当量的 GTMAC 反应制备的 30%DS 的己基取代基的 HCS-GTMAC 表现出最佳的水溶性、最低的最小抑菌浓度（138μg/mL）和最低杀菌浓度（275μg/mL），优于未改性壳聚糖。它的抗生物膜功效与洗必泰相当，这表明它可能成为口腔护理制剂中更环保的抗菌剂。
