Stable J‐aggregation of an aza‐BODIPY‐lipid in a liposome for optical cancer imaging

Cheng MHY, Harmatys KM, Charron DM, Chen J & Zheng G
Angewandte Chemie, 2019
DOI: 10.1002/ange.201907754

Organic building blocks are the centerpieces of “one‐for‐all” nanoparticle development, wherein their self‐assembly into a nanostructure can induce novel nanoscale properties and advance design of nanoparticles for cancer imaging. 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‐1 cm‐1) 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.