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Issue 11, 2016
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A near-infrared fluorescent probe based on chloroacetate modified naphthofluorescein for selectively detecting cysteine/homocysteine and its application in living cells

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Abstract

We have prepared a near-infrared (NIR) turn-on fluorescent probe (NFC) based on chloroacetate modified naphthofluorescein for specific detection of cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids (AAs) with the detection limits of 0.30 μM and 0.42 μM, respectively. The fluorescence intensity of the naphthofluorescein (NF) chromophore is modulated by an internal charge transfer (ICT) process. The probe NFC is readily available and weakly fluorescent, but of observably enhanced fluorescence after reacting with Cys or Hcy. We assumed and then demonstrated that the fluorescence off–on process involves a conjugate nucleophilic substitution/cyclization sequence. Furthermore, the probe has been successfully applied for detecting the total content of Cys and Hcy in human plasma and imaging in living cells with low toxicity.

Graphical abstract: A near-infrared fluorescent probe based on chloroacetate modified naphthofluorescein for selectively detecting cysteine/homocysteine and its application in living cells

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Publication details

The article was received on 21 Jun 2016, accepted on 18 Sep 2016 and first published on 19 Sep 2016


Article type: Paper
DOI: 10.1039/C6PP00219F
Citation: Photochem. Photobiol. Sci., 2016,15, 1393-1399
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    A near-infrared fluorescent probe based on chloroacetate modified naphthofluorescein for selectively detecting cysteine/homocysteine and its application in living cells

    J. Wang, C. Zhou, W. Liu, J. Zhang, X. Zhu, X. Liu, Q. Wang and H. Zhang, Photochem. Photobiol. Sci., 2016, 15, 1393
    DOI: 10.1039/C6PP00219F

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