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β -环糊精聚轮烷的合成及其细胞摄取行为的研究Synthesis and Cellular Uptake Behaviour of
β -Cyclodextrin Polyrotaxane- 高分子学报 2017年第2期 页码：306-314
- 作者机构：
南京大学化学化工学院 南京 210023
- 作者简介：
武伟, E-mail: wuwei@nju.edu.cn Wu Wei, E-mail: wuwei@nju.edu.cn
- 基金信息：国家自然科学基金(21474045);国家自然科学基金(51690153);国家自然科学基金(51422303)
DOI：10.11777/j.issn1000-3304.2017.16268
中图分类号：纸质出版日期：2017-2-20，
收稿日期：2016-9-3，
修回日期：2016-10-26，
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张亚军, 张正奎, 陈伟芝, 李成, 武伟, 蒋锡群.
β -环糊精聚轮烷的合成及其细胞摄取行为的研究[J]. 高分子学报, 2017,(2):306-314.Ya-jun Zhang, Zheng-kui Zhang, Wei-zhi Chen, Cheng Li, Wei Wu, Xi-qun Jiang. Synthesis and Cellular Uptake Behaviour of
β -Cyclodextrin Polyrotaxane[J]. Acta Polymerica Sinica, 2017,(2):306-314.张亚军, 张正奎, 陈伟芝, 李成, 武伟, 蒋锡群.
β -环糊精聚轮烷的合成及其细胞摄取行为的研究[J]. 高分子学报, 2017,(2):306-314. DOI： 10.11777/j.issn1000-3304.2017.16268.Ya-jun Zhang, Zheng-kui Zhang, Wei-zhi Chen, Cheng Li, Wei Wu, Xi-qun Jiang. Synthesis and Cellular Uptake Behaviour of
β -Cyclodextrin Polyrotaxane[J]. Acta Polymerica Sinica, 2017,(2):306-314. DOI： 10.11777/j.issn1000-3304.2017.16268.
摘要
以聚丙二醇-双[3
4
5-三（炔丙氧基）苯甲酰胺]为轴，以小体积的2-叠氮乙醇为封端剂通过水相炔-叠氮点击化学反应（CuAAC）生成的多个三氮唑进行封端，合成了新型的
β
-环糊精聚轮烷.利用核磁氢谱和旋转坐标系欧沃豪斯增益谱对所合成的
β
-环糊精聚轮烷进行了结构表征.进一步通过聚轮烷上的羟基，在聚轮烷上依次共价连接了水溶性聚合物聚乙二醇和荧光分子FITC
对聚轮烷进行了亲水化改性和荧光标记，研究了改性后的聚轮烷的细胞毒性和细胞摄取行为，结果表明，改性后的聚轮烷具有良好的细胞相容性，并可通过胞吞的方式被细胞摄取.
Abstract
A novel synthetic strategy of
β
-cyclodextrin (
β
-CD) polyrotaxane (PR) was developed using poly (propylene glycol) (PPG) terminated by 3
4
5-tris (prop-2-yn-1-yloxy)-benzamide groups as the axle and 2-azidoethanol as the end-capping reagent. Being different from the traditional synthetic strategy of CD PR
where bulky end-capping reagents were generally used
this strategy used small-sized 2-azidoethanol as the end-capping reagent to produce 3 triazole rings at each end by Cu (I)-catalyzed alkyne-azide 1
3-dipolar cycloaddition (CuAAC). The triazole rings thus produced blocked the CD rings on the PPG axle. The small size of the end-capping reagent could effectively reduce the steric hindrance of the end-capping reaction. Furthermore
the end-capping reaction CuAAC was conducted in water
preventing the polypseudorotaxane (PPR) from dissociation that generally occurred in organic solvents due to the absence of hydrophobic interaction. The synthesized
β
-CD PR was characterized structurally by
1
H-NMR and 2D rotating-frame Overhauser effect spectroscopy (2D ROESY).
1
H-NMR spectrum of the synthesized
β
-CD PR showed broad and unresolved proton signals
revealing that the supramolecular architecture of the
β
-CD PR was stable in DMSO and the rotaxanation significantly reduced the conformational flexibility of
β
-CD and PPG axle
causing the broadened signals. On the basis of the integral intensity of the
1
H-NMR signals
it was calculated that about 3
β
-CD rings were locked on one PPG axle. In the 2D ROESY spectrum of
β
-CD PR
a strong cross-peak appeared
owing to the nonbonding interaction between the methyl protons (
δ
=1.08) of the PPG axle and the C (3) H (
δ
=3.59) and C (5) H (
δ
=3.47) protons of the
β
-CD units
confirming that the CD rings were really threaded onto the PPG axle and successfully locked by the end-capping groups. Using the abundant hydroxyl groups in PR
we performed the PEGylation and fluorescence labeling of the
β
-CD PR and studied the cytotoxicity and cellular uptake of the modified PR
the results indicated that the modified
β
-CD PR had no detectable cytotoxicity and could be internalized by cells through an endocytosis process.
关键词
β-环糊精聚轮烷合成方法细胞毒性细胞摄取
Keywords
β-Cyclodextrin polyrotaxaneSynthetic strategyCytotoxicityCellular uptake
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