Modular synthesis of amphiphilic chitosan derivatives based on copper-free click reaction for drug delivery

被引:10
作者
Tao, Yu [1 ]
Qu, Ding [1 ,2 ]
Tian, Chunli [1 ]
Huang, Yingshuang [1 ]
Xue, Lingjing [1 ]
Ju, Caoyun [1 ]
Hao, Meixi [1 ]
Zhang, Can [1 ]
机构
[1] China Pharmaceut Univ, Ctr Adv Pharmaceut & Biomat, Jiangsu Key Lab Drug Discovery Metab Dis, State Key Lab Nat Med, Nanjing 210009, Peoples R China
[2] Nanjing Univ Chinese Med, Affiliated Hosp Integrated Tradit Chinese & Weste, Nanjing 210028, Peoples R China
基金
中国国家自然科学基金;
关键词
Modular synthesis; Amphiphilic chitosan derivatives; SPAAC click reaction; Paclitaxel; Drug carrier; IN-VITRO EVALUATION; CARBOXYMETHYL CHITOSAN; SULFATED CHITOSAN; NANOPARTICLES; CHEMISTRY; MICELLES; FILMS;
D O I
10.1016/j.ijpharm.2021.120798
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Amphiphilic chitosan derivatives have attracted wide attention as drug carriers due to their physicochemical properties. However, obtaining a desired amphiphilic chitosan derivative by tuning the various functional groups was complex and time-consuming. Therefore, a facile and common synthesis strategy would be promising. In this study, a modular strategy based on strain-promoted azide-alkyne cycloaddition (SPAAC) click reaction was designed and applied in synthesizing deoxycholic acid- or octanoic acid-modified N-azido propionyl-N,O-sulfate chitosan through tuning the hydrophobic groups. Additionally, chitosan derivatives with the same substitute groups were prepared via amide coupling as controls. We demonstrated that these derivates via the two strategies showed no obvious difference in physicochemical properties, drug loading ability and biosafety, indicating the feasibility of modular strategy. Notably, the modular strategy exhibited advantages including high reactivity, flexibility and reproducibility. We believe that this modular strategy could provide varied chitosan derivatives in an easy and high-efficiency way for improving multifunctional drug carriers.
引用
收藏
页数:10
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