Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB 2 -type host-guest-conjugated amphiphilic molecules for controlled drug delivery

• Published in: Beilstein journal of organic chemistry Vol. 15; pp. 1925 - 1932
• Main Authors: Bai, Yang, Liu, Cai-Ping, Chen, Di, Zhuo, Long-Hai, Bu, Huai-Tian, Tian, Wei
• Format: Journal Article
• Language: English
• Published: Germany 13.08.2019
• Subjects: controlled drug delivery; stimuli-responsive; β-cyclodextrin; host–guest interaction; supramolecular self-assemblies
• ISSN: 1860-5397; 1860-5397
• DOI: 10.3762/bjoc.15.188

Although stimuli-responsive supramolecular self-assemblies have been constructed, the controlled drug delivery induced by morphology transitions of these supramolecular self-assemblies on the basis of host-guest-conjugated monomers (HGCMs) are few reported. In this paper, the self-assembly behaviors of AB -type HGCMs, e.g., β-cyclodextrin-benzimidazole (β-CD-BM ), were investigated at neutral and acidic pH conditions, respectively. Specifically, β-CD-BM first self-assembled into fan-shaped supramolecular self-assemblies with a hydrodynamic diameter of 163 nm at neutral pH, whereas they were further dissociated into spherical supramolecular self-assemblies with a size of 52 nm under acidic conditions. This morphology transition process was utilized to conduct a two-stage DOX delivery under neutral and acidic pH. Basic cell experiments demonstrated that the drug-loaded β-CD-BM -based supramolecular self-assemblies with varied morphology could inhibit cancer cell proliferation, indicating their potential application in the field of drug delivery.