Detecting Cysteine in Bioimaging with a Near-Infrared Probe Based on a Novel Fluorescence Quenching Mechanism

被引:17
|
作者
Tao, Yuanfang [1 ]
Ji, Xin [2 ]
Zhang, Jian [1 ]
Jin, Yue [1 ]
Wang, Nannan [1 ]
Si, Yubing [3 ]
Zhao, Weili [1 ,2 ]
机构
[1] Henan Univ, Sch Mat Sci & Engn, Minist Educ, Key Lab Special Funct Mat, Jinming Campus, Kaifeng 475004, Peoples R China
[2] Fudan Univ, Sch Pharm, Inst Integrat Med, Shanghai 201203, Peoples R China
[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450006, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
bioimaging; BODIPY; cysteine; near-infrared fluorescence; HIGHLY SELECTIVE DETECTION; TURN-ON PROBE; DUAL-EMISSION CHANNELS; RECENT PROGRESS; IN-VIVO; COLORIMETRIC CHEMOSENSORS; LIVING CELLS; BODIPY DYES; GLUTATHIONE; DISCRIMINATION;
D O I
10.1002/cbic.202000313
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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 mu M, which was promising for detecting cysteine quantificationally. Significantly, BDP-NIR was capable of sensing endogenous cysteine in living cells andin vivo.
引用
收藏
页码:3131 / 3136
页数:6
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