Redox-Responsive Amphiphilic Macromolecular [2]Pseudorotaxane
Constructed from a Water-Soluble Pillar[5]arene and a Paraquat-Containing
Homopolymer
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Abstract
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