A H2O2-Responsive Boron Dipyrromethene-Based Photosensitizer for Imaging-Guided Photodynamic Therapy

Zhi-Wei Wang; Dan Su; Xiao-Qiang Li; Jing-Jing Cao; De-Chao Yang; Jian-Yong Liu

doi:10.3390/molecules24010032

Molecules (Dec 2018)

A H2O2-Responsive Boron Dipyrromethene-Based Photosensitizer for Imaging-Guided Photodynamic Therapy

Zhi-Wei Wang,
Dan Su,
Xiao-Qiang Li,
Jing-Jing Cao,
De-Chao Yang,
Jian-Yong Liu

Affiliations

Zhi-Wei Wang: State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Dan Su: State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Xiao-Qiang Li: State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Jing-Jing Cao: State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China
De-Chao Yang: State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Jian-Yong Liu: State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China

DOI: https://doi.org/10.3390/molecules24010032
Journal volume & issue: Vol. 24, no. 1
p. 32

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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