A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells
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...
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| Format: | Article |
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Nature Portfolio
2017-06-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-017-03901-8 |
| _version_ | 1818857939240222720 |
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| author | Yi Wang Meiqing Zhu Erkang Jiang Rimao Hua Risong Na Qing X. Li |
| author_facet | Yi Wang Meiqing Zhu Erkang Jiang Rimao Hua Risong Na Qing X. Li |
| author_sort | Yi Wang |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-19T08:48:21Z |
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| id | doaj.art-abb1f17e5688446aa81dd9f306acf07c |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-12-19T08:48:21Z |
| publishDate | 2017-06-01 |
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| spelling | doaj.art-abb1f17e5688446aa81dd9f306acf07c2022-12-21T20:28:46ZengNature PortfolioScientific Reports2045-23222017-06-01711910.1038/s41598-017-03901-8A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living CellsYi Wang0Meiqing Zhu1Erkang Jiang2Rimao Hua3Risong Na4Qing X. Li5Department of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West RoadDepartment of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West RoadState Key Laboratory of Tea Plant Biology and Utilization, School of Life Sciences, Anhui Agriculture University, No. 130 Changjiang West RoadDepartment of Science of Pesticides, School of Resources and Environment, Anhui Agricultural University, No. 130 Changjiang West RoadCollaborative 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. 95Department of Molecular Biosciences and Bioengineering, University of Hawaii at Manoa, 1955 East-West RoadAbstract 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.https://doi.org/10.1038/s41598-017-03901-8 |
| spellingShingle | Yi Wang Meiqing Zhu Erkang Jiang Rimao Hua Risong Na Qing X. Li A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells Scientific Reports |
| title | A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells |
| title_full | A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells |
| title_fullStr | A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells |
| title_full_unstemmed | A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells |
| title_short | A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells |
| title_sort | simple and rapid turn on esipt fluorescent probe for colorimetric and ratiometric detection of biothiols in living cells |
| url | https://doi.org/10.1038/s41598-017-03901-8 |
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