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In the present work, we have explored the use of amphiphilic bis-imidazolium based macrocycles and an open chain analog for the successful synthesis of gold nanoparticles (AuNPs). The macrocyclic ligands incorporate hydrophobic chains of different lengths, and the newly synthesized ligands were further used for the synthesis of AuNPs in a biphasic system. The successfully synthesized AuNPs were thoroughly characterized. The sizes of the AuNPs were ca. 8 nm, using macrocyclic ligands bearing two 10 carbon atoms alkyl chains, ca. 5 nm in the case of macrocyclic ligands with two 18 carbon atoms alkyl chains, and ca. 7 nm for the open chain ligand with two 18 carbon atoms alkyl chains. Their possible application as vehicles to load and release anionic drugs (such as sodium ibuprofenate) was also assessed and compared with previously described open chain analogs. In this case, it was observed that the AuNPs had high efficiency in extracting sodium ibuprofenate from an aqueous solution. The application as a drug delivery vehicle was confirmed by in vitro release experiments at different pH values. [ABSTRACT FROM AUTHOR]

A bis-imidazolium-based amphiphilic molecule was used to form novel supramolecular gels in ethanol–water mixtures. The proportion of solvents, the concentration of gellant and the temperature are factors that strongly influence the gelling process. The physical gels that are formed comprise entangled fibers of around 100 nm in diameter, able to incorporate anionic drugs, whose morphology varies depending on the drug they incorporate. These hydrogels are soft and therefore optimum for skin application. They show good stability when compared to previously reported gels. Suitable drug release and skin permeation profiles were obtained, and, moreover, they seem to promote the retention of the drug inside the skin. Finally, effective in vivo anti-inflammatory activity was observed, especially with the indomethacin-incorporated gel, which indicates that these supramolecular hydrogels are a good option for the delivery of poor water soluble drugs for the treatment of acute inflammation or other skin diseases. [ABSTRACT FROM AUTHOR]