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Cell‐Membrane‐Targeted Drug Delivery System Based on Choline‐Phosphate‐Functionalized β‐Cyclodextrin
Author(s) -
Feng Ying,
Xin Qiangwei,
Zhang Wanlin,
Wang Zuxin,
Gao Shan,
Chen Xin,
Chen Xingyu,
Li Jianshu
Publication year - 2020
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.202000069
Subject(s) - chemistry , cyclodextrin , drug delivery , cytotoxicity , membrane , internalization , phosphate , choline , targeted drug delivery , cell membrane , beta cyclodextrins , combinatorial chemistry , stereochemistry , biophysics , nuclear chemistry , biochemistry , cell , organic chemistry , in vitro , biology
In this study, a novel cyclodextrin derivative, i.e., zwitterionic choline phosphate (CP)‐functionalized β‐cyclodextrin (CP‐β‐CD) is successfully synthesized by click chemistry reaction. CP‐β‐CD has excellent cell‐membrane‐targeted ability because of the CP group can bind to phosphate choline (PC) in the cell membrane and promote the cellular uptake. Due to the introduction of CP group on β‐CD, it disrupts the hydrogen network between natural β‐CD molecules. Meanwhile, the water solubility of CP‐β‐CD is improved dramatically to 816 mg mL −1 , which is 440 times as that of unmodified β‐CD. Apatinib, a small molecular inhibitor, is used as a model of hydrophobic drug and loaded into CP‐β‐CD to study the solubilization effect and the anti‐angiogenisis activity. In addition, the cytotoxicity of CP‐β‐CD is also studied, and it is demonstrated that CP‐β‐CD is nontoxic. These results indicate that the apatinib can be transported into cell interior and play an excellent anti‐angiogenisis activity after being loaded into CP‐β‐CD drug delivery system. This work suggests that the water soluble CP‐β‐CD with excellent cell internalization efficiency has a potential application prospect in the field of drug delivery.