Near-infrared Cyanine-based Fluorescent Probe for Cysteine with High Selectivity

doi:10.7517/j.issn.1674-0475.2018.03.004

Abstract

Abstract: We developed a turn-on cyanine-based near-infrared (NIR) probe which can selectively detect cysteine. In this probe Cy-CF₃, 4-(trifluoromethyl)thiophenol moiety is employed as both the recognition unit and fluorescence quenching group. With the titration of cysteine, a large blue shift (160 nm) is observed in the absorption spectra of Cy-CF₃, accompanying with significant color changes. The probe Cy-CF₃ shows obviously fluorescent enhancement at 780 nm in emission spectra. Over all, the probe Cy-CF₃ exhibits high selectivity for cysteine over glutathione and other potential interferences. The reaction mechanism of Cy-CF₃ with cysteine is verified by mass spectra, ¹HNMR spectra and absorption spectra, indicating that 4-(trifluoromethyl)thiophenol in the probe Cy-CF₃ could be replaced by cysteine, and then the PET process from 4-(trifluoromethyl)thiophenol to cyanine is blocked. The cell experiments also demonstrate that this probe could be successfully applied for the detection of cysteine in living cells.

Key words: near-infrared, cysteine, fluorescent probe, cyanine

MA Yaguang, ZHANG Yutao, MA Yiyu, GUO Zhiqian, ZHU Weihong. Near-infrared Cyanine-based Fluorescent Probe for Cysteine with High Selectivity[J]. Imaging Science and Photochemistry, 2018, 36(3): 236-244.

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