Anticancer pH-Responsive Supramolecular Vesicles Fabricated Using Water-Soluble Pillar[5]arene and Curcumin Derivative

A pH-responsive curcuminoid delivery system based on supramolecular vesicles was fabricated via a novel host–guest inclusion complex between water-soluble pillar[5]arene (WP5) and hydrophobic bisdemethoxycurcumin (BDMC). This WP5 and BDMC (WP5 ⊃ BDMC) inclusion complex was studied using 1H NMR, UV–vis, and fluorescence spectroscopy. This resulting inclusion complex could self-assemble into well-defined supramolecular vesicles by host–guest interactions and presented a significant pH-responsive behavior, which was investigated using dynamic laser scattering, transmission electron microscopy, and UV–vis spectroscopy. The suitable preservation time for WP5 ⊃ BDMC and the construction ratio between host/guest molecules were both of great significance for the aggregated morphology of supramolecular vesicles. Furthermore, the BDMC complexes showed good anticancer ability in vitro, as they could inhibit HepG2 cell proliferation and migration. Therefore, the curcuminoid vesicles could provide a promising platform for drug delivery or food packaging utilization.