Near-Infrared Fluorescent Probe with High Quantum Yield and Its Application in the Selective Detection of Glutathione in Living Cells and Tissues.
Glutathione (GSH), cysteine (Cys), and homocysteine (Hcy) are small-molecular biothiols that play key roles in various biological systems. Among these biothiols, GSH is the most abundant intracellular thiol. Until now, a small number of the near-infrared (NIR) fluorescent probes have been designed for the detection of GSH. Unfortunately, most of these NIR probes are based on cyanine dyes, which generally suffer low fluorescence quantum yield (Φ < 0.25), which are not suitable for bioimaging. In addition, some probes are difficult to effectively distinguish GSH from Cys and Hcy. In this work, an NIR fluorescent probe with high fluorescence quantum yield is developed by introducing a rigid coplanar structure such as rhodamine dyes, and the NIR probe (CyR) with spirolactam structure is first synthesized and used to recognize GSH. The characteristics of this NIR probe are as follows: (1) probe CyR exhibits high fluorescence quantum yield (Φ = 0.43) after the addition of GSH and high sensitivity toward GSH with 75-fold fluorescence enhancement. (2) The probe is highly selective, which will not interfere with the other biological thiols (Cys, Hcy) and amino acids. (3) A possible reaction mechanism of the NIR probe CyR and GSH (Cys, Hcy) can be proposed and proved by1H NMR,13C NMR, and MS (mass spectra). (4) The NIR probe displays selective detection of GSH in biological samples such as living cells and tissues.
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan, Hunan 411105, PR China.
Jun-Ying
JY
Xie
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan, Hunan 411105, PR China.|State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, Hunan 410082, PR China.
Chun-Yan
CY
Li
College of Chemical Engineering, Xiangtan University , Xiangtan, Hunan 411105, PR China.
Yong-Fei
YF
Li
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan, Hunan 411105, PR China.
Junjie
J
Fei
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan, Hunan 411105, PR China.
Fen
F
Xu
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan, Hunan 411105, PR China.
Juan
J
Ou-Yang
Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan, Hunan 411105, PR China.
Juan
J
Liu
D000818:Animals; D002470:Cell Survival; D005456:Fluorescent Dyes / Q000032:analysis* / Q000737:chemistry; D005978:Glutathione / Q000032:analysis*; D006367:HeLa Cells; D006801:Humans; D007259:Infrared Rays; D008099:Liver / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory; D051381:Rats
D005456:Fluorescent Dyes; D005978:Glutathione