1,8-Naphthalimide-based imidazolium salts differing for the alkyl chain length and the nature of the anion were synthesized and characterized to obtain fluorescent probes for bioimaging applications. First, their self-assembly behavior and gelling ability were investigated in water and water/dimethyl sulfoxide binary mixtures. Only salts having longer alkyl chains were able to give supramolecular hydrogels, whose properties were investigated by using a combined approach of fluorescence, resonance light scattering, and rheology measurements. Morphological information was obtained by scanning electron microscopy. In addition, conductive properties of organic salts in solution and gel state were analyzed. Imidazolium salts were successfully tested for their possible application as bioimaging and cytotoxic agents toward three cancer cell lines and a nontumoral epithelial cell line. Characterization of their behavior was performed by MTT and cell-based assays. Finally, the biological activity of hydrogels was also investigated. Collectively, our findings showed that naphthalimide-based imidazolium salts are promising theranostic agents and they were able to preserve their biological properties also in the gel phase.
Keywords: bioimaging; fluorescence; imidazolium salts; naphthalimide; supramolecular hydrogels.