Near-infrared vinyl-containing aza-BODIPY nanoparticles as photosensitizer for phototherapy

Novel vinyl-containing pyrroles were developed by the reaction of vinyl-containing ketones with 3-phenyl-2H-azirine in the presence of LDA. Utilizing these pyrroles, asymmetric vinyl-containing azaBDPs 1-8 were prepared, avoiding to the use of Knoevenagel condensation. Solid-state structure of 7 was confirmed by X-ray crystallographic analysis, and the furan, the vinyl group and the pyrrole segment in 7 are almost coplanar, owing to the conjugation. AzaBDPs 1-8 absorb and emit beyond 685 nm, and have low fluorescence quantum yields. AzaBDPs 1-8 were found to merely possess the O-1(2) production capacity. The formed azaBDP nanoparticles (7-NPs) by facile encapsulation of F127 exhibit the excellent photothermal stabilities. Noteworthily, 7-NPs show the outstanding photothermal conversion efficiency (eta = 55%) in aza-BODIPY system, and can effectively kill cancer cells through the photothermal conversion, which is highly desirable for an effective and potential tumor phototherapeutic reagent.

Automated summary

A novel vinyl-containing pyrrole compound was developed through the reaction of vinyl-containing ketones with 3-phenyl-2H-azirine in the presence of LDA. This compound was then used to prepare asymmetric vinyl-containing azaBDPs 1-8, avoiding the use of Knoevenagel condensation. Among them, the formed azaBDP nanoparticles (7-NPs) exhibited excellent photothermal stabilities and a high photothermal conversion efficiency (eta = 55%) in the aza-BODIPY system, effectively killing cancer cells through photothermal conversion, showing potential as a tumor phototherapeutic agent.