Organic building blocks are the centerpieces of "one-for-all" nanoparticle development. Herein, we report the synthesis of a novel aza-BODIPY-lipid building block and its self-assembly into a liposomal nanoparticle (BODIPYsome). We observed optically stable NIR J-aggregation within the BODIPYsome that is likely attributed to J-dimerization. BODIPYsomes with cholesterol showed enhanced colloidal stability while maintaining a high extinction coefficient (128 mm cm ) and high fluorescence quenching (99.70±0.09 %), which enables photoacoustic (PA) properties from its intact structure and recovered NIR fluorescence properties when it is disrupted in cancer cells. Finally, its capabilities for optical imaging (PA/fluorescence) were observed in an orthotopic prostate tumor mouse model 24 h after intravenous administration. Overall, the BODIPYsome opens the door for engineering new building blocks in the design of optically stable biophotonic imaging agents.
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