Multistimuli Responsive Supramolecular Vesicles Based on the Recognition of p-Sulfonatocalixarene and its Controllable Release of Doxorubicin

We report the novel construction of nanosupramolecular binary vesicles based on host-guest complex formation between p-sulfonatocalix[4]arene and asymmetric viologen, which was identified by UV-vis and fluorescence spectroscopy, dynamic laser scattering, transmission electron microscopy, scanning electron microscopy, and surface tension experiments. The critical aggregation concentration of asymmetric viologen decreases pronouncedly by a factor of ca. 1000 owing to the complexation of p-sulfonatocalix[4]arene. Furthermore, we have demonstrated that the resulting vesicles can respond to multiple external stimuli, including temperature, host-guest inclusion, and redox. Methods of warming and inclusion of cyclodextrins were then employed to disrupt the vesicle architecture to release hydrophilic doxorubicin from the interior of the vesicle. Finally, cell experiments were performed to evaluate the cellular toxicity of the supramolecular binary vesicle and the anticancer efficiency of doxorubicin-loaded vesicle.