Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB<sub>2</sub>-type Host-guest-conjugated Amphiphilic Molecule

Yao Hao; Wang Jing-xia; Song Xin; Zhang Hai-tao; Fan Xiao-dong; Tian Wei

doi:10.11777/j.issn1000-3304.2017.16202

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Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB₂-type Host-guest-conjugated Amphiphilic Molecule

Research Article | 更新时间：2021-03-12

- Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB₂-type Host-guest-conjugated Amphiphilic Molecule
- Acta Polymerica Sinica Issue 1, Pages: 63-70(2017)
- 作者机构：
  
  陕西省高分子科学与技术重点实验室西北工业大学理学院西安 710072
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2017.16202
  CLC：
- Published：2017-1，
  
  Received：16 June 2016，
  
  Revised：22 July 2016，
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Yao Hao, Wang Jing-xia, Song Xin, Zhang Hai-tao, Fan Xiao-dong, Tian Wei. Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB₂-type Host-guest-conjugated Amphiphilic Molecule. [J]. Acta Polymerica Sinica (1):63-70(2017)
DOI：

Yao Hao, Wang Jing-xia, Song Xin, Zhang Hai-tao, Fan Xiao-dong, Tian Wei. Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB₂-type Host-guest-conjugated Amphiphilic Molecule. [J]. Acta Polymerica Sinica (1):63-70(2017) DOI： 10.11777/j.issn1000-3304.2017.16202.

摘要

合成了一种同时含有单偶氮苯基团和双β-环糊精单元的AB

型两亲分子（Azo-CD

），并通过核磁共振谱和基质辅助激光解吸电离飞行时间质谱对其结构进行了表征和确认.动态光散射和透射电子显微镜测试结果表明，在水溶液中，Azo-CD

在无任何外界刺激的条件下可自发地形成球形自组装体，而当施加超声振动后逐渐转变为超分子超支化聚合物自组装体；该自组装体被进一步施加紫外光辐射后可解离成尺寸较小的支化聚集体，而其在可见光辐射下又可以可逆地变回原来的超支化自组装形貌.利用紫外分光光度计测试Azo-CD

自组装体对抗癌药物阿霉素（DOX）的释放曲线发现，通过超声和光的双重调控作用可实现Azo-CD

自组装体对DOX的程序化控制释放.利用一维

H-NMR谱和二维NOESY谱进一步阐明了Azo-CD

自组装体形貌转变过程与其程序化控释结果的相关关系.

Abstract

An AB

-type host-guest-conjugated amphiphilic molecule (Azo-CD

) composed of one azobenzene (Azo) and two

-cyclodextrin (

-CD) units was first synthesized through the click reaction of Azo-(N

)

intermediate containing two azide groups and mono-6-deoxy-6-alkyne

-CD (

-CD-C≡CH) with one alkynyl group. The molecular structure of Azo-CD

was confirmed by

H and

C nuclear magnetic resonances and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The morphology transitions of Azo-CD

self-assemblies were then investigated by transmission electron microscopy (TEM) and dynamic light scattering (DLS). Both TEM and DLS results indicated that Azo-CD

self-assembled into spherical aggregates without external stimuli

and then transformed to bigger supermolecular hyperbranched polymer self-assemblies (SHPS) induced by ultrasound in aqueous solution. These SHPS could be further dissociated into small branched aggregates under UV light irradiation

whereas reverted to supermolecular hyperbranched self-assemblies again by visible light irradiation. By utilizing the above ultrasound and photo-dually tuned self-assembly morphology transition features

a three-stage programmed drug delivery behavior was observed through the cumulative release curves of doxorubicin (DOX)-loaded self-assemblies. Furthermore

the correlativity between self-assembly morphology transitions and programmed drug release was proved by

H-NMR in D

O and two dimensional nuclear overhauser effect spectroscopy. These results indicated that Azo-CD

first self-assembled into spherical self-assemblies due to the hydrophilic-hydrophobic interaction

accompanied by a slow release of DOX. And then

the ultrasound stimulus broke the hydrophilic-hydrophobic balance and enhanced the host-guest interaction between

-CD and Azo

further leading to the formation of SHPS with a fast release of DOX. Furthermore

UV light irradiation induced the cis-trans isomerism of Azo and the dissociation of Azo/

-CD

resulting in the dissociation of SHPS into small branched aggregates with a much faster release. While visible light irradiation enhanced the host-guest interaction and made small branched aggregates revert to supermolecular hyperbranched self-assemblies.

关键词

主客体型两亲分子超分子自组装超分子超支化聚合物超声响应性光响应性程序化控释

Keywords

Host-guest-conjugated amphiphilic moleculeSupermolecular self-assemblySupermolecular hyperbranched polymerUltrasound-responsivenessPhoto-responsivenessProgrammed drug delivery

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Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB2-type Host-guest-conjugated Amphiphilic Molecule

DOI：10.11777/j.issn1000-3304.2017.16202

摘要

Abstract

关键词

Keywords

references

Ultrasound-and Photo-dually Controlled Supermolecular Self-assembly and Programmed Drug Delivery Based on an AB₂-type Host-guest-conjugated Amphiphilic Molecule