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      A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells

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          Abstract

          Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play a key role in an extensive range of physiological processes and biological functions. Therefore, the selective and sensitive detection of intracellular thiols is important for revealing cellular function. In this study, ethyl 2-(4-(acryloyloxy)-3-formylphenyl)-4-methylthiazole-5-carboxylate ( NL-AC) was designed and synthesized as a colorimetric and ratiometric fluorescent probe that can be utilized to rapidly, sensitively and selectively detect biothiols in physiological media. The fluorescence intensity of this probe using the three target biothiols at a concentration of 20 equiv. of the probe increased by approximately 6~10-fold in comparison to that without the biothiols in aqueous solution. The limits of detection (LOD) for Cys, Hcy and GSH were 0.156, 0.185, and 1.838 μM, respectively. In addition, both 1H-NMR and MS analyses suggested the mechanism of fluorescence sensing to be excited-state intramolecular proton transfer (ESIPT). The novel colorimetric and ratiometric probe is structurally simple and offers detection within 20 min. Furthermore, this probe can be successfully applied in bioimaging. The results indicate high application potential in analytical chemistry and diagnostics.

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          Glutathione: overview of its protective roles, measurement, and biosynthesis.

          This review is the introduction to a special issue concerning, glutathione (GSH), the most abundant low molecular weight thiol compound synthesized in cells. GSH plays critical roles in protecting cells from oxidative damage and the toxicity of xenobiotic electrophiles, and maintaining redox homeostasis. Here, the functions and GSH and the sources of oxidants and electrophiles, the elimination of oxidants by reduction and electrophiles by conjugation with GSH are briefly described. Methods of assessing GSH status in the cells are also described. GSH synthesis and its regulation are addressed along with therapeutic approaches for manipulating GSH content that have been proposed. The purpose here is to provide a brief overview of some of the important aspects of glutathione metabolism as part of this special issue that will provide a more comprehensive review of the state of knowledge regarding this essential molecule.
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            Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives.

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              Design strategies of fluorescent probes for selective detection among biothiols.

              Simple thiol derivatives, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play key roles in biological processes, and the fluorescent probes to detect such thiols in vivo selectively with high sensitivity and fast response times are critical for understanding their numerous functions. However, the similar structures and reactivities of these thiols pose considerable challenges to the development of such probes. This review focuses on various strategies for the design of fluorescent probes for the selective detection of biothiols. We classify the fluorescent probes for discrimination among biothiols according to reaction types between the probes and thiols such as cyclization with aldehydes, conjugate addition-cyclization with acrylates, native chemical ligation, and aromatic substitution-rearrangement.
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                Author and article information

                Contributors
                rimaohua@ahau.edu.cn
                risongna@163.com
                Journal
                Sci Rep
                Sci Rep
                Scientific Reports
                Nature Publishing Group UK (London )
                2045-2322
                29 June 2017
                29 June 2017
                2017
                : 7
                : 4377
                Affiliations
                [1 ]ISNI 0000 0004 1760 4804, GRID grid.411389.6, Department of Science of Pesticides, , School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West Road, ; Hefei, 230036 China
                [2 ]GRID grid.108266.b, Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, , College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, ; Zhengzhou, 450002 China
                [3 ]ISNI 0000 0001 2188 0957, GRID grid.410445.0, Department of Molecular Biosciences and Bioengineering, , University of Hawaii at Manoa, 1955 East-West Road, ; Honolulu, HI 96822 USA
                [4 ]ISNI 0000 0004 1760 4804, GRID grid.411389.6, State Key Laboratory of Tea Plant Biology and Utilization, , School of Life Sciences, Anhui Agriculture University, No. 130 Changjiang West Road, ; Hefei, 230036 China
                Article
                3901
                10.1038/s41598-017-03901-8
                5491497
                28663561
                11f03f47-3a34-4060-959a-7aabb6e72dbe
                © The Author(s) 2017

                Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

                History
                : 13 January 2017
                : 3 May 2017
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