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O-Carboxymethyl chitosan-based pH-responsive amphiphilic chitosan derivatives: characterization, aggregation behavior, and application
Carbohydrate Polymers ( IF 10.7 ) Pub Date : 2020-03-04 , DOI: 10.1016/j.carbpol.2020.116112
Qun Liu , Yan Li , Xiaodeng Yang , Shu Xing , Congde Qiao , Shoujuan Wang , Chunlin Xu , Tianduo Li

Chitosan has attracted much attention in drug delivery, however, carboxymethyl chitosan (CMC)-based self-aggregated nanocarriers are seldom reported. In this paper, two kinds of CMC-based pH-responsive amphiphilic chitosan derivatives, N-2-hydroxylpropyl-3-butyl ether-O-carboxymethyl chitosan (HBCC) and N-2-hydroxylpropyl-3-(2-ethylhexyl glycidyl ether)-O-carboxymethyl chitosan (H2ECC), have been synthesized by the homogeneous reaction. The molecular structures were characterized by FTIR, 1H NMR and 13C NMR. The optimum reaction condition was obtained based on the data of 1H NMR spectrum: reaction time of 4 h, reaction temperature of 80 °C and nepoxyn-NH2 of 3/1, respectively. The XRD patterns showed the crystallinity of HBCC and H2ECC decreased due to the introduction of hydrophobic segments. The thermostability of HBCC and H2ECC was improved for the formation of heat-resistant stereo-complexed structures. The intermolecular hydrophobic interaction hindered the intermolecular mobility by increasing glass transition temperature of ca. 10 °C. Both HBCC and H2ECC have very low critical aggregation concentrations (HBCC: 0.66∼1.56 g/L, H2ECC: 0.57∼1.07 g/L) and moderate aggregate particle size, which is advantageous for utilization as a drug carrier. The curcumin loaded HBCC and H2ECC aggregates showed nontoxicity, meanwhile, HBCC and H2ECC showed good antibacterial activity against Staphylococcus Aureus and Escherichia Coli. As a result of these two favorable properties, HBCC and H2ECC could be used as curcumin nanocarriers as well as antibacterial agents.



中文翻译:

基于O-羧甲基壳聚糖的pH响应两亲性壳聚糖衍生物:表征,聚集行为和应用

壳聚糖在药物递送中引起了很多关注,但是,很少有基于羧甲基壳聚糖(CMC)的自聚集纳米载体的报道。本文研究了两种基于CMC的pH响应两亲性壳聚糖衍生物,即N -2-羟丙基-3-丁基醚-O-羧甲基壳聚糖(HBCC)和N -2-羟丙基-3-(2-乙基己基缩水甘油醚) )-O-羧甲基壳聚糖(H2ECC)已通过均相反应合成。分子结构通过FTIR,1 H NMR和13 C NMR表征。根据1 H NMR谱图数据,确定了最佳反应条件:反应时间4 h,反应温度80°C和ñËpØXÿñ--ñH2分别为3/1。X射线衍射图谱表明HBCC和H2ECC的结晶度由于引入了疏水链段而降低。改善了HBCC和H2ECC的热稳定性,以形成耐热的立体复合结构。分子间的疏水性相互作用通过提高玻璃化转变温度约200℃而阻碍了分子间的迁移。10°C。HBCC和H2ECC的临界聚集浓度都非常低(HBCC:0.66至1.56 g / L,H2ECC:0.57至1.07 g / L),聚集颗粒大小适中,有利于用作药物载体。姜黄素负载的HBCC和H2ECC聚集体显示无毒,同时HBCC和H2ECC对金黄色葡萄球菌和大肠杆菌具有良好的抗菌活性。由于这两个有利的特性,

更新日期:2020-03-04
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