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Drug delivery systems that can be employed to load anticancer drugs and release them triggered by a specific stimulus, such as glutathione, are of great importance in cancer therapy. In this study, supramolecular porphysome nanovesicles that were self-assembled by amphiphilic porphyrin derivatives were successfully constructed, mainly driven by the π-π stacking, hydrogen bonding, and hydrophobic interactions, and were used as carriers of anticancer drugs. The nanovesicles are monodispersed in shape and uniform in size. The drug loading and in vitro drug release investigations indicate that these nanovesicles are able to encapsulate doxorubicin (DOX) to achieve DOX-loaded nanovesicles, and the nanovesicles could particularly release the loaded drug triggered by a high concentration of glutathione (GSH). More importantly, the drug release in cancer cells could be monitored by fluorescent recovery of the porphyrin derivative. Cytotoxicity experiments show that the DOX-loaded nanovesicles possess comparable therapeutic effect to cancer cells as free DOX. This study presents a new strategy in the fabrication of versatile anticancer drug nanocarriers with stimuli-responsive properties. Thus, the porphysome nanovesicles demonstrated here might offer an opportunity to bridge the gap between intelligent drug delivery systems and imaging-guided drug release.

A cyanostilbene-based amphiphile (CS) was synthesized, which could self-assemble into non-emissive bilayer vesicles and ultra-thin ribbons. Cucurbit[7]uril (CB[7]) could form an inclusion complex with CS with a significant hypochrome effect, giving a strong blue emission from non-emissive species. CS underwent photoisomerization induced by light irradiation, which allowed the membrane contraction into smaller vesicles.

A series of new platinum-acetylide complexes 4a-4c and 6a-6c were synthesized and characterized. The gelation properties of these compounds were investigated by the "stable-to-inversion-of-test-tube" method. Unlike compounds 4a-4c, amides 6b and 6c can gelate a variety of nonpolar alkyl solvents; this result indicates that the hydrogen bonds between amide groups play an important role in the formation of metallic organogels. Interestingly, compared to the typical morphologies of known organogels or metallic organogels, compounds 6b and 6c exhibited highly ordered honeycomb patterns on a large-scale (determined by SEM analysis). To investigate the driving forces for the self-assembly process, concentration-dependent (1)H NMR spectroscopy and a competitive experiment between hydrogen bonds were used to confirm that intermolecular hydrogen bonding play an essential role during the formation of supramolecular aggregates.

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