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A fluorescent probe for discrimination of cysteine/homocysteine, glutathione and hydrogen polysulfides

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Abstract

Biothiols of cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and hydrogen polysulfides (H2Sn, n > 1) play vital roles in physiological and pathological processes. In this manuscript, a fluorescent probe (compound 1) for simultaneous detection and discrimination of Cys/Hcy, GSH and H2Sn was developed, employing fluorophore of 1-(benzo[d]thiazol-2-yl)naphthalen-2-oxy linked with 7-nitrobenzo-2-oxa-1,3-diazole (NBD) as a response unit and a quencher. Compound 1 exhibited different ratiometric colorimetric responses toward GSH at 430 nm and 375 nm from Cys/Hcy at 480 nm and 375 nm, while it displayed a different colorimetric response at 561 nm toward H2Sn. Meanwhile it could act as a naked-eye probe toward GSH, Cys/Hcy and H2Sn with corresponding solution color of light yellow, orange and purple, respectively. Upon excitation at 370 nm, compound 1 responded to all these biothiols with 'turn-on' blue fluorescence, whereas upon excitation at 470 nm, it could respond to Cys/Hcy with 'turn-on' green fluorescence. Data of mass spectra, lifetimes and 1H NMR spectra interpreted the aromatic nucleophilic substitutions of compound 1 by GSH, Cys/Hcy and H2Sn to produce fluorophore1-(benzo[d]thiazol-2-yl)naphthalen-2-ol (compound 2) and corresponding NBD derivatives which could be discriminated through their absorption and fluorescence signals as well as solution colors. Furthermore, compound 1 was applied to image Cys/Hcy and H2Sn/GSH in 786-O cells.

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Acknowledgements

The authors thank the National Natural Science Foundation of China (21702047, 81700578), Scientific and Technological Project of the Henan Province of China (192102110053), and Henan International Joint Laboratory of Laser Technology in Agricultural Sciences for Financial Support.

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Authors and Affiliations

  1. College of Sciences, Henan Agricultural University, Zhengzhou, 450002, People’s Republic of China

    Puhui Xie, Yanru Zhu, Guangqin Gao & Song Jiang

  2. Department of Nephrology, Henan Provincial Key Laboratory of Kidney Disease and Immunology, Henan Provincial People’s Hospital (Zhengzhou University People’s Hospital), Zhengzhou, 450003, Henan, People’s Republic of China

    Yanliang Wang

  3. Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, People’s Republic of China

    Fengqi Guo

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  1. Puhui Xie
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  2. Yanru Zhu
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Xie, P., Zhu, Y., Wang, Y. et al. A fluorescent probe for discrimination of cysteine/homocysteine, glutathione and hydrogen polysulfides. Res Chem Intermed 47, 1123–1138 (2021). https://doi.org/10.1007/s11164-020-04320-7

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  • DOI: https://doi.org/10.1007/s11164-020-04320-7

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