Issue 32, 2021

Construction of a pH-sensitive self-assembly in aqueous solutions based on a dansyl-modified β-cyclodextrin

Abstract

Here we present a pH-responsive self-assembly based on a β-cyclodextrin (β-CD) derivative bearing a dansyl terminus (βCD-C6–Dns). Vesicular structures were formed over the entire studied pH range (8.5–0.7); however, the molecular configuration and packing within the vesicles were different at different pH values. Intramolecular host–guest complexation occurred mainly between the dansyl group and β-CD at pH values where the dansyl group was not protonated. The alkyl chain also acted as a competitive guest to form host–guest inclusions as confirmed by 2D 1H NMR measurements. The pH-responsive βCD-C6–Dns vesicles have potential application prospects in pH-controlled drug release based on the low cytotoxicity of βCD-C6–Dns.

Graphical abstract: Construction of a pH-sensitive self-assembly in aqueous solutions based on a dansyl-modified β-cyclodextrin

Supplementary files

Article information

Article type
Paper
Submitted
21 May 2021
Accepted
05 Jul 2021
First published
05 Jul 2021

Soft Matter, 2021,17, 7516-7523

Construction of a pH-sensitive self-assembly in aqueous solutions based on a dansyl-modified β-cyclodextrin

B. Jiang, Y. Liu, L. Zhao, L. Zhao, C. Wang, C. Liu and B. Xu, Soft Matter, 2021, 17, 7516 DOI: 10.1039/D1SM00751C

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