Synthesis and Cellular Uptake Behaviour of <italic style="font-style: italic">β</italic>-Cyclodextrin Polyrotaxane

Ya-jun Zhang; Zheng-kui Zhang; Wei-zhi Chen; Cheng Li; Wei Wu; Xi-qun Jiang

doi:10.11777/j.issn1000-3304.2017.16268

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Synthesis and Cellular Uptake Behaviour of β-Cyclodextrin Polyrotaxane

Research Article | 更新时间：2021-05-18

- Synthesis and Cellular Uptake Behaviour of β-Cyclodextrin Polyrotaxane
- Acta Polymerica Sinica Issue 2, Pages: 306-314(2017)
- 作者机构：
  
  南京大学化学化工学院南京 210023
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2017.16268
  CLC：
- Published：20 February 2017，
  
  Received：3 September 2016，
  
  Revised：26 October 2016，
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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 (2):306-314(2017)
DOI：

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 (2):306-314(2017) DOI： 10.11777/j.issn1000-3304.2017.16268.

摘要

以聚丙二醇-双[3

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

-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

-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

-cyclodextrin (

-CD) polyrotaxane (PR) was developed using poly (propylene glycol) (PPG) terminated by 3

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

-CD PR was characterized structurally by

H-NMR and 2D rotating-frame Overhauser effect spectroscopy (2D ROESY).

H-NMR spectrum of the synthesized

-CD PR showed broad and unresolved proton signals

revealing that the supramolecular architecture of the

-CD PR was stable in DMSO and the rotaxanation significantly reduced the conformational flexibility of

-CD and PPG axle

causing the broadened signals. On the basis of the integral intensity of the

H-NMR signals

it was calculated that about 3

-CD rings were locked on one PPG axle. In the 2D ROESY spectrum of

-CD PR

a strong cross-peak appeared

owing to the nonbonding interaction between the methyl protons (

=1.08) of the PPG axle and the C (3) H (

=3.59) and C (5) H (

=3.47) protons of the

-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

-CD PR and studied the cytotoxicity and cellular uptake of the modified PR

the results indicated that the modified

-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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⁰

Synthesis and Cellular Uptake Behaviour of β-Cyclodextrin Polyrotaxane

DOI：10.11777/j.issn1000-3304.2017.16268

摘要

Abstract

关键词

Keywords

references