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A NIR facile cell-compatible fluorescent sensor for glutathione based on Michael addition induced cascade spirolactam opening and its application in hepatocellular carcinoma

Abstract

A NIR fluorescence probe with long emission wavelength at 746 nm and high quantum yield for 0.36 to selectively detect GSH over Hcy and Cys in living systems was designed and synthesized. 2-(1,3,3-Trimethylindolin-2-ylidene) acetaldehyde was connected to rhodamine by Knoevenagel Condensation in order to elongated the emission to near infrared region. Then it was connected with ethylenediamine to get important intermediate. Finally, target molecule named RhNM was synthesized through conjugated N-[4-(carbonyl) phenyl]. RhNM shows excellent discrimination of GSH from Hcy/Cys along with obvious color changes. The fluorescence band has a rapid increase at 746 nm enhanced 106-fold after adding GSH, the quantum was calculated for 0.36. The titration experiments of GSH brought good linear relationship of intensity, then detection limit was calculate for 70 nM. The proposed mechanism of identifying GSH based on Michael addition through reactions involving the carbon-carbon double bond and intramolecular amino induced spirolactam opening. Meanwhile, the probe RhNM can work in a wide range of pH for 4-10. The probe RhNM was used for endogenous and exogenous imaging in HepG2 cells for glutathione. There was an outstanding intracellular red fluorescence occurred upon the addition of GSH incubated with HepG2 cells. The results show that it has been successfully applied for determination of GSH in diluted serum and bio-imaging of GSH in living cells with low cell toxicity. All the results indicated that the probe can be used as an ultra-sensitive, near-infrared fluorescent chemical sensor for selectively detect GSH in living cell. It has great potential in the live tissues and even in animal imaging.

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Publication details

The article was received on 03 Sep 2018, accepted on 11 Oct 2018 and first published on 13 Oct 2018


Article type: Paper
DOI: 10.1039/C8TB02309C
Citation: J. Mater. Chem. B, 2018, Accepted Manuscript
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    A NIR facile cell-compatible fluorescent sensor for glutathione based on Michael addition induced cascade spirolactam opening and its application in hepatocellular carcinoma

    X. yang and Y. Qian, J. Mater. Chem. B, 2018, Accepted Manuscript , DOI: 10.1039/C8TB02309C

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