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Detecting Cysteine in Bioimaging with a Near-Infrared Probe Based on a Novel Fluorescence Quenching Mechanism |
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| Authors: | Yuanfang Tao Xin Ji Dr Jian Zhang Yue Jin Nannan Wang Prof Yubing Si Prof Weili Zhao |
| Affiliation: | 1. Key Laboratory for Special Functional Materials of Ministry of Education, School of Materials Science and Engineering, Henan University, Jinming Campus, Kaifeng, 475004 P. R. China
These authors contributed equally to this work.;2. School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai, 201203 P. R. China These authors contributed equally to this work.;3. Key Laboratory for Special Functional Materials of Ministry of Education, School of Materials Science and Engineering, Henan University, Jinming Campus, Kaifeng, 475004 P. R. China;4. College of Chemistry, Zhengzhou University, Zhengzhou, 450006 P. R. China |
| Abstract: | Near-infrared (NIR) fluorescent probes are very significant for detecting cysteine in biological systems. Herein, we report a highly selective and sensitive NIR turn-on fluorescent probe (BDP-NIR) based on BODIPY with large Stokes shift (105 nm) for detecting Cys. We clarified the sensing mechanism based on the different thiol-induced SNAr substitution/rearrangement reaction of the probe with cysteine and homocysteine/glutathione, which leads to the corresponding amino- and thiol-BODIPY dyes with distinct photophysical properties. Moreover, a novel mechanism of fluorescence quenching was demonstrated by density functional theory calculation. The reason for the fluorescence quenching of the probe might be intersystem crossing (from singlet to triplet excited state). Moreover, BDP-NIR had a high linear dynamic range of 0–500 μM, which was promising for detecting cysteine quantificationally. Significantly, BDP-NIR was capable of sensing endogenous cysteine in living cells and in vivo. |
| Keywords: | bioimaging BODIPY cysteine near-infrared fluorescence |