Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (4): 397-405.DOI: 10.11944/j.issn.1000-0518.2016.04.160053

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A Turn-On Fluorescent Probe for Cysteine Based on Benzopyran

YANG Tingting,GUO Zhiqian,SHAO Andong,ZHAO Ping(),ZHU Weihong   

  1. Institute of Fine Chemicals,East China University of Science & Technology,Shanghai 200237,China
  • Received:2016-02-01 Accepted:2016-03-02 Online:2016-04-01 Published:2016-04-01
  • Contact: ZHAO Ping
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.61306022)

Abstract:

A benzopyran-based turn-on near-infrared probe (E)-2-(benzopyran)ethenyl-5-(diethylamino)phenyl acrylate(DCM-AC) has been successfully synthesized. Acrylate bond is specifically designed for the response units of amino acid. The results show that the spectral response of DCM-AC towards cysteine is highly sensitivity and selectivity. With increasing the concentration(1.0~8.0 μmol/L) of cysteine, a significant color change can be observed and the fluorescent intensity of DCM-AC at 710 nm increases gradually, showing a good linear relationship with concentration. The limit of detection of DCM-AC for cysteine is determined as 2.8×10-7 mol/L. DCM-AC exhibits a highly selective probe for cysteine over homocysteine and glutathione, with no interference of other substances. The recognition mechanism of the DCM-AC to cysteine is verified by mass spectrum,1H NMR titration and absorption spectra, indicating that cysteine thiol groups attack at acrylate double bond of DCM-AC by addition reaction, and finally removed as the cyclic lactam compound.

Key words: cysteine, fluorescent probe, benzopyran, selectivity