Self-assembled nanoparticles based on supramolecular-organic frameworks and temoporfin for an enhanced photodynamic therapy in vitro and in vivo.

Water-soluble three-dimensional supramolecular-organic frameworks (SOFs) and temoporfin (mTHPC) are discovered to form uniform self-assembled nanoparticles. These nanoparticles demonstrate an improved 1O2 generation efficiency due to the reduced aggregation-caused quenching effect. SOFs and self-assembled nanoparticles are biocompatible. Self-assembled nanoparticles display an improved photo cytotoxicity toward four types of human cancer cells. The tumor model in mice shows that self-assembled nanoparticles could efficiently suppress tumor growth in vivo.

A supramolecular assembly mediated by host-guest interactions for improved chemo-photodynamic combination therapy.

We report a supramolecular nanomedicine (SNM-3) based on a camptothecin-tetraphenyl porphyrin conjugate, camptothecin-polyethylene glycol conjugate, and acyclic cucurbit[n]uril. The supramolecular nanomedicine is tunable by varying the composition of the three components to optimize the nanoscale morphology and therapeutic efficacy. The optimized supramolecular nanomedicine possesses great stability and enhanced intracellular singlet oxygen generation efficiency. Cytotoxicity assay demonstrates that SNM-3 improves the efficacy of chemo-photodynamic combination therapy against three cancer cell lines.

Transformative Supramolecular Vesicles Based on Acid-Degradable Acyclic Cucurbit[n]uril and a Prodrug for Promoted Tumoral-Cell Uptake.

Smart supramolecular vesicles constructed by host-guest interactions between "acid-degradable" acyclic cucurbit[n]uril (CB[n]) and a doxorubicin prodrug are reported. "Acid-degradable" acyclic CB[n] is a high-affinity host for several common antitumor drugs, and its degradation leads to a more dramatic decrease in binding affinity than that observed for "acid-sensitive" hosts. Supramolecular complexation between acid-degradable acyclic CB[n] and a doxorubicin prodrug resulted in the formation of negatively charged supramolecular vesicles. The prodrug strategy allowed doxorubicin to be conjugated to vesicles in a stable manner with a high drug-loading ratio of 20 %. The resulting supramolecular vesicles were responsive to tumor acidity (pH 6.5). Induced by mildly acidic conditions (pH 6.5-5.5), acid-degradable acyclic CB[n] could be degraded, and this led to a vesicle-to-micelle transition to form positively charged micelles. This transition resulted in a pH-dependent change in size and surface charge, which improved tumoral-cell uptake for doxorubicin.

Step-Growth Cyclo-Oligomerization for the Preparation of Di- and Tetrafunctionalized Pillar[5]arenes.

The preparation of complex functionalized pillar[ n]arenes (PA[ n]s) is challenging by one-pot cocyclization or selective deprotection method. We developed a step-growth cyclo-oligomerization method to synthesize functionalized PA[5]s. Dimers, trimers, and tetramers were synthesized and characterized. With this new method, we were able to prepare three di- and tetrafunctionalized PA[5]s. By using a multistep synthetic strategy, the chance to form constitutional isomers and other by-products was reduced. Therefore, complex tetrafunctionalized PA[5]s were prepared with improved yield.

A new synthetic method for non-symmetric pillar[5]arenes with simple isolation and improved yield.

The conventional method to synthesize non-symmetric pillar[n]arenes (PA[n]s) generally results in a low yield and requires laborious isolation. We developed a new synthetic method to prepare non-symmetric PA[5]s with various substitutions. Monomers were synthesized starting from commercially available chemicals. The desired products could be easily isolated with an improved yield.