A fluorescent probe for discrimination of cysteine/homocysteine, glutathione and hydrogen polysulfides
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A fluorescent probe for discrimination of cysteine/ homocysteine, glutathione and hydrogen polysulfides Puhui Xie1 · Yanru Zhu1 · Yanliang Wang2 · Guangqin Gao1 · Song Jiang1 · Fengqi Guo3 Received: 28 August 2020 / Accepted: 31 October 2020 © Springer Nature B.V. 2020
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 H 2Sn was developed, employing fluorophore of 1-(benzo[d]thiazol-2-yl)naphthalen-2-oxy linked with 7-nitrobenzo2-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 H 2Sn 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 H 2Sn/ GSH in 786-O cells. Keywords Fluorescent probe · Biothiols · Discrimination · Ratiometric colorimetric responses · Aromatic nucleophilic substitutions
Electronic supplementary material The online version of this article (doi:https://doi.org/10.1007/ s11164-020-04320-7) contains supplementary material, which is available to authorized users. * Puhui Xie [email protected] * Fengqi Guo [email protected] Extended author information available on the last page of the article
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Introduction Reactive sulfur species (RSS) are essential in many respects of biological redox homeostasis, cell signaling and the regulation of metabolism. Important RSS include cysteine (Cys), homocysteine (Hcy), glutathione (GSH), hydrogen sulfide (H2S), and hydrogen polysulfides (H2Sn, n > 1) et al. [1–3], endogenously distributed in living cells. Among these RSS, H2S has been recognized as the third critical gaseous molecule besides carbon monoxide (CO) and nitrogen (II) oxide (NO) in biological systems. Explorations in recent years have demonstrated that both the endogenously produced H2S and the exogenously administrated H2S would cause protective effects during the course of many pathologies [4–6]. H2Sn (n > 1) have recently aroused a lot of interest, because they were found to act
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