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

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(2)-type HGCMs, e.g., β-cyclodextrin-benzimidazole(2) (β-CD-BM(2)), were investigated at neutral and acidic pH conditions, respectively. Specifically, β-CD-BM(2) 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(2)-based supramolecular self-assemblies with varied morphology could inhibit cancer cell proliferation, indicating their potential application in the field of drug delivery.