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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

A Near-Infrared Fluorescent Probe Based on Chloroacetate Modified Naphthofluorescein for Selectively Detecting cysteine/homocysteine and Its Application in Living Cells

Jianxi Wang, Cheng Zhou, Wei Liu, Jianjian Zhang, Xinyue Zhu, Xiaoyan Liu, Qin Wang, Haixia Zhang

Photochem Photobiol Sci. 2016 Nov 2;15(11):1393-1399.

PMID: 27714261

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP61419021	Naphthofluorescein		61419-02-1	Price

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