Structural, Photophysical, and Photobiological Studies on BODIPY-Anthracene Dyads

Abstract

We report the structural, photophysical, and photobiological properties of a promising BODIPY-anthracene dyad (BAD) that was previously shown to i nduce a therapeutic effect against MDA-MB-468 cells. The BODIPY was synthesized and its crystal structure was elucidated. We further investigate the potential of this molecule as a versatile photosensitizer for photodynamic therapy against AY27 and F98 cancer cell models. Both necrosis and apoptosis were found to play a role in cell death and G1 phase arrestation was observed following PDT. From time-resolved spectroscopic analysis of absorbance and luminescence, it was found that the singlet oxygen quantum yield of the most promising BODIPY anthracene dyad is high (>70%) and originates from a triplet state. Interestingly, despite the efficient PDT effect, long-lived triplet states or singlet oxygen formation were not observed when water (or D2O) was used as the solvent but were readily observed in solvents such as MeOH and EtOH.