Abstract
In this study, we demonstrate a novel H2O2 activatable photosensitizer (compound 7) 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 7 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 7 even with low concentration is particularly sensitive to human cervical carcinoma (HeLa) cells (IC50 = 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.
Highlights
Photodynamic therapy (PDT) has received great attention for their advantages such as minimal invasiveness, high selectivity and low immunogenicity [1,2]
When exposed to the near-infrared light, it would generate singlet oxygen to kill the cancer cells. These ideal features of tumor microenvironment-activated ability, effective therapeutic effect and near infrared (NIR) fluorescence imaging make this kind of PS a promising anticancer agent for selective photodynamic therapy
We introduce iodine atoms incorporated into the 2 and 6 positions of the boron dipyrromethene (BODIPY) core, which can facilitate intersystem crossing to promote the generation of singlet oxygen [38]
Summary
Zhi-Wei Wang † , Dan Su † , Xiao-Qiang Li, Jing-Jing Cao, De-Chao Yang and Jian-Yong Liu *. State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical. Received: 26 November 2018; Accepted: 18 December 2018; Published: 21 December 2018
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