期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 41, 页码 18172-18178出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202006687
关键词
amphiphilic block copolymers; carbamate linkers; encapsulation stability; functionalized PEG; self-assembly
资金
- National Natural Science Foundation of China (NNSFC) Project [51690150, 51690154, 21674103, U19A2094]
- International S&T Cooperation Program of China (ISTCP) of MOST [2016YFE0129700]
Commercial PEG-amine is of unreliable quality, and conventional PEG functionalization relies on esterification and etherification steps, suffering from incomplete conversion, harsh reaction conditions, and functional-group incompatibility. To solve these challenges, we propose an efficient strategy for PEG functionalization with carbamate linkages. By fine-tuning terminal amine basicity, stable and high-fidelity PEG-amine with carbamate linkage was obtained, as seen from the clean MALDI-TOF MS pattern. The carbamate strategy was further applied to the synthesis of high-fidelity multi-functionalized PEG with varying reactive groups. Compared to with an ester linkage, amphiphilic PEG-PS block copolymers bearing carbamate junction linkage exhibits preferential self-assembly tendency into vesicles. Moreover, nanoparticles of the latter demonstrate higher drug loading efficiency, encapsulation stability against enzymatic hydrolysis, and improved in vivo retention at the tumor region.
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