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Sensors and actuators. B, Chemical v.259, 2018년, pp.219 - 225   SCI SCIE SCOPUS
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Construction of a fluorine substituted chromenylium-cyanine near-infrared fluorophore for ratiometric sensing

Zhu, Xiaoyan (Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, College of Biology, Collaborative Innovation Center for Chemistry and Molecular Medicine, Hunan University, Changsha 410082, PR China ) ; Yuan, Lin (Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, College of Biology, Collaborative Innovation Center for Chemistry and Molecular Medicine, Hunan University, Changsha 410082, PR China ) ; Hu, Xiaoxiao (College of Life Sciences, Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Bio-Sensing and Chemometric, College of Chemistry and Chemical Engineering, Aptamer Engineering Center of Hunan Province, Hunan University, Changsha 410082, PR China, PR China ) ; Zhang, Lili (Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engin ) ; Liang, Yuxin ; He, Shengyuan ; Zhang, Xiao-Bing ; Tan, Weihong ;
  • 초록  

    Abstract Near-infrared (NIR) fluorescent probes have been considered as powerful tools for exploring bioactive species and biological processes in living systems by virtue of the substantial merits of the NIR window (such as minimal photo-toxicity, deep tissue penetration, and low background interference). However, the development of effective NIR fluorescent probes for biological application is still facing great challenges due to some weakness (for example, pH sensitivity, poor chemical and photo-stability) of mainly current NIR fluorophores. Herein, we synthesized a novel fluorine atom substituted NIR chromenylium-cyanine fluorophore, termed CCF-OH , with an optically tunable hydroxyl group. Compound CCF-OH possess several optical advantages, including high chemical stability, high photo-stability, and high fluorescence quantum yield (Φ = 0.47). Significantly, a low pK a value (6.3) of CCF-OH was obtained, making its fluorescence signal steady around the pH ranging from 6.8 to 8.1. To demonstrate the practicability of CCF-OH , a mitochondria-targeted near-infrared fluorescent probe, N-Cys , was developed by masking the hydroxyl group of CCF-OH with an acrylate group as the recognition unit for cysteine (Cys). N-Cys responded to Cys with an obvious ratiometric signal. Furthermore, N-Cys has also been successfully applied for ratiometric NIR imaging of Cys in living cells, suggesting the great potential of the new NIR fluorophore, CCF-OH , for practical applications in living systems. Highlights A novel fluorine atom substituted NIR chromenylium-cyanine fluorophore (termed CCF-OH ) was proposed. CCF-OH exhibited high fluorescence quantum yield, high chemical and photo-stability, and stable fluorescence signal around the pH range from 6.8 to 8.1. To demonstrate the practicability of CCF-OH , a mitochondria-targeted near-infrared fluorescent probe, N-Cys , was developed by using CCF-OH as the fluorescent reporter. Probe N-Cys displayed excellent selectivity, high sensitivity, and ratiometric response to Cys. Probe N-Cys has also been successfully applied for ratiometric NIR imaging of Cys in living cells, suggesting the great potential of the new NIR fluorophore, CCF-OH , for practical applications in living systems. Graphical abstract [DISPLAY OMISSION]


  • 주제어

    Near-infrared .   Ratiometric .   Fluorescent probe .   Mitochondria-targeted .   Cysteine .   Imaging.  

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