Reversible Stabilization of Vesicles: Redox‐Responsive Polymer Nanocontainers for Intracellular Delivery

Abstract

We present the self-assembly of redox-responsive polymer nanocontainers comprising a cyclodextrin vesicle core and a thin reductively cleavable polymer shell anchored via host-guest recognition on the vesicle surface. The nanocontainers are of uniform size, show high stability, and selectively respond to a mild reductive trigger as revealed by dynamic light scattering, transmission electron microscopy, atomic force microscopy, a quantitative thiol assay, and fluorescence spectroscopy. Live cell imaging experiments demonstrate a specific redox-responsive release and cytoplasmic delivery of encapsulated hydrophilic payloads, such as the pH-probe pyranine, and the fungal toxin phalloidin. Our results show the high potential of these stimulus-responsive nanocontainers for cell biological applications requiring a controlled delivery.

Preparation of quadruple responsive polymeric micelles combining temperature‐, pH‐, redox‐, and UV‐responsive behaviors and its application in controlled release system

“…22 In addition to lightsensitive polymeric systems, thermo-responsive polymers and molecular-responsive polymers have also been widely reported, that is, polymers that undergo self-assembly or sharp-changing of the assembly upon temperature or pH change, bubbling of CO 2 , and adding of reductant. [23][24][25][26][27][28][29][30][31][32][33][34] Although significantly progress has been made in the past decades, artificial stimuli responsive systems are far less sophisticated than natural polymers, that is, proteins that can respond to multi stimuli and changes assembly structures accordingly. Thus, multi-responsive systems that respond to two or more Additional Supporting Information may be found in the online version of this article.…”

Polymer Nanocontainers for Intracellular Delivery

“…To overcome this problem, De Vries et al. developed a redox‐responsive polymer‐shelled nanocontainer with cyclodextrin vesicles acting as a non‐sacrificial template (Figure ) . The amphiphilic cyclodextrins self‐assembled into vesicles, the adamantane‐terminated poly(acrylic acid) formed the polymer shell through host–guest interactions, and cross‐linking by reduction‐cleavable cysteamine formed the stable polymer nanocontainer.…”

“…In the case of PSV OEtO , the FITC‐phalloidin remains trapped. Reproduced with permission . Copyright 2017, Wiley‐VCH.…”

Macrocyclic Amphiphiles for Drug Delivery

“…[29] CDs are the most widely used macrocycles as pharmaceutical additives, affording inclusion for a lot of hydrophobic drugs ( Figure 1). [30] Reasonably, amphiphilic CDs could serve as nanocarriers [31] for these drugs [32] with pharmaceutical performance improved. [33] Because of the good biocompatibility of amphiphilic CDs, they are the most widely studied macrocyclic amphiphiles in drug delivery up to now.…”