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

Abstract

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 had a binding constant of (8.49 ± 2.20) × 104 L·mol-1 with 1:1 binding stoichiometry, and it was studied using 1H NMR, UV–vis, and fluorescence spectroscopy. This resulting inclusion complex could self-assemble into well-defined supramolecular vesicles 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.

Note:
Funding Information: This work was supported by the National Natural Science Foundation of China (Nos. 21703200 and 21773203), the Chey Institute for Advanced Studies International Scholar Exchange Fellowship for the academic year of 2021-2022, and China Scholarship Council program.

Conflict of Interests: The authors declare no competing financial interest.

Keywords: Curcumin, host-guest interaction, vesicle, pillar[5]arene, bioactivity