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

Jiang, Bing; Liu, Yu; Zhao, Linlin; Zhao, Li; Wang, Ce; Liu, Changyao; Xu, Baocai · Soft Matter · 2021

basic_science · Level V

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Abstract

Here we present a pH-responsive self-assembly based on a β-cyclodextrin (β-CD) derivative bearing a dansyl terminus (βCD-C<sub>6</sub>-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 <sup>1</sup>H NMR measurements. The pH-responsive βCD-C<sub>6</sub>-Dns vesicles have potential application prospects in pH-controlled drug release based on the low cytotoxicity of βCD-C<sub>6</sub>-Dns.

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