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Fluorescent In Situ Targeting Probes for Rapid Imaging of Ovarian‐Cancer‐Specific γ‐Glutamyltranspeptidase
Author(s) -
Wang Feiyi,
Zhu Ying,
Zhou Li,
Pan Liang,
Cui Zhifen,
Fei Qiang,
Luo Sihang,
Pan Dun,
Huang Qing,
Wang Rui,
Zhao Chunchang,
Tian He,
Fan Chunhai
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502899
Subject(s) - chemistry , bodipy , fluorescence , moiety , in situ , enzyme , ovarian cancer , cancer cell , biophysics , biochemistry , stereochemistry , cancer , biology , physics , organic chemistry , quantum mechanics , genetics
γ‐Glutamyltranspeptidase (GGT) is a tumor biomarker that selectively catalyzes the cleavage of glutamate overexpressed on the plasma membrane of tumor cells. Here, we developed two novel fluorescent in situ targeting (FIST) probes that specifically target GGT in tumor cells, which comprise 1) a GGT‐specific substrate unit (GSH), and 2) a boron–dipyrromethene (BODIPY) moiety for fluorescent signalling. In the presence of GGT, sulfur‐substituted BODIPY was converted to amino‐substituted BODIPY, resulting in dramatic fluorescence variations. By exploiting this enzyme‐triggered photophysical property, we employed these FIST probes to monitor the GGT activity in living cells, which showed remarkable differentiation between ovarian cancer cells and normal cells. These probes represent two first‐generation chemodosimeters featuring enzyme‐mediated rapid, irreversible aromatic hydrocarbon transfer between the sulfur and nitrogen atoms accompanied by switching of photophysical properties.