Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB2-type host–guest-conjugated amphiphilic molecules for controlled drug delivery

• Published in: Beilstein journal of organic chemistry Vol. 15; no. 1; pp. 1925 - 1932
• Main Authors: Bai, Yang, Cai-ping, Liu, Chen, Di, Long-hai, Zhuo, Huai-tian, Bu, Tian, Wei
• Format: Journal Article
• Language: English
• Published: Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 01.01.2019; Beilstein-Institut
• Subjects: Benzimidazoles; Cell proliferation; Chemistry; controlled drug delivery; Cytology; Cytotoxicity; Drug delivery; Full Research Paper; host–guest interaction; Laboratories; Microscopy; Monomers; Morphology; pH effects; Self-assembly; stimuli-responsive; supramolecular self-assemblies; β-Cyclodextrin; China
• ISSN: 2195-951X; 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 AB2-type HGCMs, e.g., β-cyclodextrin-benzimidazole2 (β-CD-BM2), were investigated at neutral and acidic pH conditions, respectively. Specifically, β-CD-BM2 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-BM2-based supramolecular self-assemblies with varied morphology could inhibit cancer cell proliferation, indicating their potential application in the field of drug delivery.