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A NIR rhodamine fluorescent chemodosimeter specific for Glutathione: Knoevenagel Condensation, detection of intracellular Glutathione and living cell imaging

Abstract

A new Near-infrared probe for detecting Glutathione based on conjugate addition and intramolecular amino induced spirolactam opening, named RhAN was designed and synthesized. Firstly, rhodamine was reacted with 2-(1,3,3-Trimethylindolin-2-ylidene) acetaldehyde by Knoevenagel Condensation, and the conjugate chain was extended, obtained M2. Then M2 was connected with hydrazide to get M3. Finally, target molecule RhAN was synthesized through the combine of M3 and acryloyl chloride. In the presence of GSH, RhAN exhibits high selectivity which is specific identify GSH over Cys and Hcy, the color change from yellow to green together with the fluorescence appeared among 5 s, and had no interference while the other biological thiols and amino acids exist. The absorbance and emission wavelengh of the probe RhAN are achieved 717 nm (molar extinction coefficient is 4.36X104 M-1 cm-1) and 739 nm (quantum yield is 0.26) at near-infrared region. Its absorbance and emission intensity enhance more than 117-fold and 90-fold upon addition of GSH, respectively. In addition, it also has high sensitivity with low detection limit of 1.0 μM, and works excellently within a wide pH range of 2–10. Moreover, RhAN has been employed for endogenous and exogenous imaging in MFC-7 cell for GSH. Whatever MFC-7 cells were incubated with RhAN and added GSH or blank RhAN, it both display significant fluorescence in red channel, which indicated that the probe not only could detect exogenous GSH, but it also could permeated into the cells and reacted with the intracellular GSH. It is excellent to design fluorescence sensor RhAN as a quick and effective method for detecting excess GSH in living cell, for maintaining the balance of amino acids in the body and ensure normal life activities.

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Publication details

The article was received on 12 Dec 2017, accepted on 13 Feb 2018 and first published on 13 Feb 2018


Article type: Paper
DOI: 10.1039/C7TB03199H
Citation: J. Mater. Chem. B, 2018, Accepted Manuscript
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    A NIR rhodamine fluorescent chemodosimeter specific for Glutathione: Knoevenagel Condensation, detection of intracellular Glutathione and living cell imaging

    L. L. Tong and Y. Qian, J. Mater. Chem. B, 2018, Accepted Manuscript , DOI: 10.1039/C7TB03199H

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