Synthesis and applications of amphiphilic styryl-pyrene-BODIPYs

Among the known dyes, BODIPYs have attracted great attention for their chemical-physical properties and the possible fine tuning by relatively accessible changes in the dye skeleton, therefore the current interest in this field is still constantly growing. Nevertheless, there are not many examples of water-soluble BODIPY dyes. Here we report the synthesis, photochemical characterization and, possible applications of amphiphilic styryl BODIPY derivatives decorated with a pyrene moiety and sulfonic groups (Fig. 1). Taking advantage of the lipophilic pyrene moiety linked to the amphiphilic dye, a nanotheranostic platform can be obtained via - interactions with carbon-based nanomaterials (e.g., graphene, carbon nanotubes, etc.). The sulphonic alkyl chains anchored on the phenolic group provide unique biological features and improve the biocompatibility of dye and affect the cell internalization pathways. The new synthetized BODIPY derivatives were characterized by NMR analyses, UV-vis, steady-state, and time-resolved fluorescence emission spectroscopies. Their biological response in terms of cytotoxicity and intracellular fate, alone or in combination with graphene derivatives, was evaluated on HEPG2 cells.