Cationic Vesicles Based on Amphiphilic Pillar[5]arene Capped with Ferrocenium: A Redox‐Responsive System for Drug/siRNA Co‐Delivery

Abstract

A novel ferrocenium capped amphiphilic pillar[5]arene (FCAP) was synthesized and self‐assembled to cationic vesicles in aqueous solution. The cationic vesicles, displaying low cytotoxicity and significant redox‐responsive behavior due to the redox equilibrium between ferrocenium cations and ferrocenyl groups, allow building an ideal glutathione (GSH)‐responsive drug/siRNA co‐delivery system for rapid drug release and gene transfection in cancer cells in which higher GSH concentration exists. This is the first report of redox‐responsive vesicles assembled from pillararenes for drug/siRNA co‐delivery; besides enhancing the bioavailability of drugs for cancer cells and reducing the adverse side effects for normal cells, these systems can also overcome the drug resistance of cancer cells. This work presents a good example of rational design for an effective stimuli‐responsive drug/siRNA co‐delivery system.

Fullerene/photosensitizer nanovesicles as highly efficient and clearable phototheranostics with enhanced tumor accumulation for cancer therapy

“…S5 exhibited characteristic vibration of amide bond at 3370 cm -1 , 1645 cm -1 , and 1400 cm -1 , indicating the successful preparation of amphiphilic molecule, TFC 70 /Ce6-OEG2, in which TFC 70 -OEG2 acts as hydrophilic part and Ce6as hydrophobic part. The amphiphilic properties enable TFC 70 /Ce6-OEG2 self-assemble into vesicular structures through balance between two competing interactions during the dialysis process in water [57][58][59]. SEM image(Fig.…”

Self-Crosslinking and Surface-Engineered Polymer Vesicles

“…Vesicles are generally unilamellar or multilamellar membrane‐enclosed sacs with interior aqueous lumens, and can be prepared through the self‐assembly from a wide range of amphiphiles, including phospholipids, synthetic surfactants, and amphiphilic copolymers . Vesicles have attracted much attention due to their great potentials in nanoscience and biomedical application . Nevertheless, there are still at least two problems facing these vesicle applications.…”

Turn-On Supramolecular Host-Guest Nanosystems as Theranostics for Cancer

“…Pei and co-workers 75 designed the novel ferrocenium capped amphiphilic pillar [5]arene (FCAP) and showed that it serves as a GSH-responsive system for drug and siRNA codelivery in aqueous solution ( Figure 10B). The anti-cancer agent doxorubicin hydrochloride (DOX) was selected as a model drug for assessing the release properties of this nanocarrier.…”

“…(B) Illustration of the formation of cationic vesicles and their redox-responsive drug and siRNA release. Reprinted with permission from Chang et al75 Copyright 2014 Wiley-VCH Verlag GmbH & Co. KGaA.…”