Synthesis and Characterization of a Dual-sensitive Copolymer Containing Curcumins and Zwitterionic Sulfobetaines as Drug Delivery Carrier

Lu Ai-jing; Hou Yu; Wu Zheng-zhong; Chen Yuan-wei; Luo Xiang-lin

doi:10.11777/j.issn1000-3304.2016.16047

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Synthesis and Characterization of a Dual-sensitive Copolymer Containing Curcumins and Zwitterionic Sulfobetaines as Drug Delivery Carrier

Research Article | 更新时间：2021-03-19

- Synthesis and Characterization of a Dual-sensitive Copolymer Containing Curcumins and Zwitterionic Sulfobetaines as Drug Delivery Carrier
- Acta Polymerica Sinica Issue 10, Pages: 1400-1408(2016)
- 作者机构：
  
  1.四川大学高分子科学与工程学院成都 610065
  2.高分子材料工程国家重点实验室(四川大学) 成都 610065
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2016.16047
  CLC：
- Published：2016-10，
  
  Received：3 February 2016，
  
  Revised：3 February 2016，
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Lu Ai-jing, Hou Yu, Wu Zheng-zhong, Chen Yuan-wei, Luo Xiang-lin. Synthesis and Characterization of a Dual-sensitive Copolymer Containing Curcumins and Zwitterionic Sulfobetaines as Drug Delivery Carrier. [J]. Acta Polymerica Sinica (10):1400-1408(2016)
DOI：

Lu Ai-jing, Hou Yu, Wu Zheng-zhong, Chen Yuan-wei, Luo Xiang-lin. Synthesis and Characterization of a Dual-sensitive Copolymer Containing Curcumins and Zwitterionic Sulfobetaines as Drug Delivery Carrier. [J]. Acta Polymerica Sinica (10):1400-1408(2016) DOI： 10.11777/j.issn1000-3304.2016.16047.

摘要

合成了聚姜黄素-二硫键-聚甲基丙烯酸二乙胺基乙酯-聚磺酸甜菜碱（Cur-DA-ss-PDEA-PS，或简写为Cur-ss-PDEA-PS），采用核磁、红外对聚合物结构进行了表征，用示差扫描量热法测试了聚合物热性能.用溶剂挥发法制备聚合物胶束，形成了聚磺酸甜菜碱为亲水壳层、聚姜黄素为疏水核、二硫键作为还原敏感基团和聚甲基丙烯酸二乙氨基乙酯为pH敏感基团的胶束.用荧光分光光度计测定了临界胶束浓度，动态光散射以及扫描电镜对胶束结构及性质进行了表征.结果显示，胶束稳定性良好，粒径分布较窄，且具有pH敏感性和还原敏感性.胶束载药量及包封率测试结果显示，相比于聚己内酯为内核的聚合物胶束，聚姜黄素的引入提高了胶束对药物的封装效果.

Abstract

A copolymer poly(curcumin)-ss-

-poly(2-(diethylamino)ethylmethacrylate)-poly{

-[2-(methacryloyloxy)ethyl]-

-diethyl-

-(3-sulfopropyl)-ammonium} (Cur-DA-ssPDEA-PS) was synthesized with the combination of atom radical transfer polymerization (ATRP) and conjugation and by sulfonation.Molecular structure of the copolymer was confirmed by

H-NMR and FTIR.Thermophysical properties of the copolymer were determined by DSC.Cur-DA-ssPDEA-PS micelles were formed by solvent evaporation using poly(zwitterionic sulfobetaines) as hydrophilic shell

poly(curcumin) as hydrophobic core

and DEA as pH sensitive content and disulfide as redox responsive linkage.Critical micelle concentration (CMC) of the copolymer in water was estimated using pyrene as a hydrophobic fluorescence probe.Dynamic light scattering (DLS) measurement was performed to determine the micellar size and distribution.Micelle morphology was observed by scanning electron microscopy (SEM).CMC obtained was about 10

-3

mg/mL

revealing that the micelles were stable.The micelle diameters were all below 200 nm with a narrow size distribution.There existed a buffer platform in pH titration curve and the micelle sizes changed when pH varying from 7.4 to 5.0.pH responsivity of the micelles was confirmed by these results.When treated by 10 mmol/L glutathione (GSH)

the micelles were damaged and aggregated

indicating a reduced micelle responsivity.The higher drug loading than PCL-ss-PDEA-PS indicated improvement of hydrophobic drug encapsulation by introduction of curcumins.

关键词

pH/还原敏感的高分子胶束药物载体磺酸甜菜碱姜黄素

Keywords

pH/Redox dual-sensitive copolymerMicellesDrug delivery carrierSulfobetainesCurcumin

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Department of Polymeric Materials, School of Materials Science and Engineering, Tongji University

Department of Orthopedics, Shanghai Tenth People's Hospital, Tongji University School of Medicine

State Key Laboratory of Polymer Material and Engineering, Sichuan University, Sichuan University

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Pharmaceutical College of Henan University, Henan University

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