Design and Characterization of Dual-Modal Fluorinated BODIPY Probes
Abstract
Multimodal imaging can improve the detection of molecular and pathophysiological changes by combining complementary readouts within a single probe. Here we report the synthesis and characterization of a fluorinated BODIPY dye (F54-BODIPY) designed as dual fluorescence/19F-MRI imaging agent. The molecular design replaces the native BF2 unit with multibranched perfluoro-tert-butoxy chains appended at the boron atom via BO hexyloxy linkages, providing 54 magnetically equivalent 19F nuclei per molecule. Additionally, 2,6-dimethylphenyl groups are introduced at 2,6-positions of F54-BODIPY, and (E)-4-methylstyryl residues at the 3,5-positions extend emission into the far-red region of visible spectrum. This probe was structurally characterized by NMR spectroscopy, and its photophysical properties were evaluated by UV-Vis absorption, fluorescence spectroscopy, and fluorescence quantum yield (Φf) measurements. Subsequently F54-BODIPY was encapsulated in poly(lactic-co-glycolic acid) (PLGA) nanoparticles (NPs) for dispersion in aqueous media. Co-encapsulation of a second fluorinated phase, namely perfluoro-15-crown-5 ether (PFCE), significantly modified fluorescence properties and introduced a second 19F-NMR signal, yielding a bimodal nanosystem with dual 19F-NMR signals and red fluorescence emission for combined fluorescence/19F-MRI bioimaging.
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