In this study, we demonstrate a novel H₂O₂ activatable photosensitizer (compound ) which contains a diiodo distyryl boron dipyrromethene (BODIPY) core and an arylboronate group that quenches the excited state of the BODIPY dye by photoinduced electron transfer (PET). The BODIPY-based photosensitizer is highly soluble and remains nonaggregated in dimethyl sulfoxide (DMSO) as shown by the intense and sharp Q-band absorption (707 nm). As expected, compound exhibits negligible fluorescence emission and singlet oxygen generation efficiency. However, upon interaction with H₂O₂, both the fluorescence emission and singlet oxygen production of the photosensitizer can be restored in phosphate buffered saline (PBS) solution and PBS buffer solution containing 20% DMSO as a result of the cleavage of the arylboronate group. Due to the higher concentration of H₂O₂ in cancer cells, compound even with low concentration is particularly sensitive to human cervical carcinoma (HeLa) cells (IC = 0.95 μM) but hardly damage human embryonic lung fibroblast (HELF) cells. The results above suggest that this novel BODIPY derivative is a promising candidate for fluorescence imaging-guided photodynamic cancer therapy.
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| http://dx.doi.org/10.3390/molecules24010032 | DOI Listing |
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