Redox-Responsive Amphiphilic Macromolecular [2]Pseudorotaxane Constructed from a Water-Soluble Pillar[5]arene and a Paraquat-Containing Homopolymer Xiaodong Chi Guocan Yu Xiaofan Ji Yang Li Guping Tang Feihe Huang 10.1021/acsmacrolett.5b00525.s001 https://acs.figshare.com/articles/journal_contribution/Redox_Responsive_Amphiphilic_Macromolecular_2_Pseudorotaxane_Constructed_from_a_Water_Soluble_Pillar_5_arene_and_a_Paraquat_Containing_Homopolymer/2132047 Here we report a redox-responsive host–guest complex between a new water-soluble pillar[5]­arene (<b>WP5</b>) and a paraquat derivative. Compared with the neutral form of the paraquat derivative that binds <b>WP5</b> weakly, its dication form binds <b>WP5</b> much more strongly. Furthermore, we utilize this new water-soluble redox-responsive molecular recognition motif to construct the first pillararene-based amphiphilic macromolecular [2]­pseudorotaxane, which self-assembles into redox-responsive polymeric vesicles in water. Such pillararene-based supramolecular vesicles were further used to construct a drug delivery system to encapsulate and controlled release DOX·HCl, an anticancer drug. The uptake of these DOX·HCl-loaded supramolecular vesicles by cancer cells was studied with confocal laser scanning microscopy. Meanwhile, DOX·HCl-loaded supramolecular vesicles showed anticancer activity in vitro comparable to free DOX·HCl under the examined conditions. 2015-09-15 00:00:00 supramolecular DOX confocal laser scanning microscopy vesicle paraquat anticancer drug delivery system WP 5