A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide
Hydrogen sulfide (H<sub>2</sub>S) as small molecular signal messenger plays key functions in numerous biological processes. The imaging detection of intracellular hydrogen sulfide is of great significance. In this work, a ratiometric fluorescent probe <b>BH</b> based on an as...
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| Format: | Article |
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7499 |
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| author | Huan Xiang Tianqing Ye Yanbo Li Yanfei Lin Dan Liu Hongwei Zhou Jianbo Wang Lei Li |
| author_facet | Huan Xiang Tianqing Ye Yanbo Li Yanfei Lin Dan Liu Hongwei Zhou Jianbo Wang Lei Li |
| author_sort | Huan Xiang |
| collection | DOAJ |
| description | Hydrogen sulfide (H<sub>2</sub>S) as small molecular signal messenger plays key functions in numerous biological processes. The imaging detection of intracellular hydrogen sulfide is of great significance. In this work, a ratiometric fluorescent probe <b>BH</b> based on an asymmetric BODIPY dye for detection of H<sub>2</sub>S was designed and synthesized. After the interaction with hydrogen sulfide, probe display colorimetric and ratiometric fluorescence response, with its maximum emission fluorescence wavelength red-shifted from 542 nm to 594 nm, which is attributed to the sequential nucleophilic reaction of H<sub>2</sub>S leading to enhanced molecular conjugation after ring formation of the BODIPY skeleton. A special response mechanism has been fully investigated by NMR titration and MS, so that the probe has excellent detection selectivity. Furthermore, probe <b>BH</b> has low cytotoxicity and fluorescence imaging experiments indicate that it can be used to monitor hydrogen sulfide in living cells. |
| first_indexed | 2024-03-09T18:48:15Z |
| format | Article |
| id | doaj.art-b556878c41b8460fb2170a2cccc9370d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:48:15Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b556878c41b8460fb2170a2cccc9370d2023-11-24T06:05:13ZengMDPI AGMolecules1420-30492022-11-012721749910.3390/molecules27217499A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen SulfideHuan Xiang0Tianqing Ye1Yanbo Li2Yanfei Lin3Dan Liu4Hongwei Zhou5Jianbo Wang6Lei Li7Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaJiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, ChinaHydrogen sulfide (H<sub>2</sub>S) as small molecular signal messenger plays key functions in numerous biological processes. The imaging detection of intracellular hydrogen sulfide is of great significance. In this work, a ratiometric fluorescent probe <b>BH</b> based on an asymmetric BODIPY dye for detection of H<sub>2</sub>S was designed and synthesized. After the interaction with hydrogen sulfide, probe display colorimetric and ratiometric fluorescence response, with its maximum emission fluorescence wavelength red-shifted from 542 nm to 594 nm, which is attributed to the sequential nucleophilic reaction of H<sub>2</sub>S leading to enhanced molecular conjugation after ring formation of the BODIPY skeleton. A special response mechanism has been fully investigated by NMR titration and MS, so that the probe has excellent detection selectivity. Furthermore, probe <b>BH</b> has low cytotoxicity and fluorescence imaging experiments indicate that it can be used to monitor hydrogen sulfide in living cells.https://www.mdpi.com/1420-3049/27/21/7499hydrogen sulfideBODIPYratiometric fluorescent probenucleophilic reactioncolorimetric |
| spellingShingle | Huan Xiang Tianqing Ye Yanbo Li Yanfei Lin Dan Liu Hongwei Zhou Jianbo Wang Lei Li A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide Molecules hydrogen sulfide BODIPY ratiometric fluorescent probe nucleophilic reaction colorimetric |
| title | A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide |
| title_full | A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide |
| title_fullStr | A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide |
| title_full_unstemmed | A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide |
| title_short | A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide |
| title_sort | new ratiometric fluorescent probe based on bodipy for highly selective detection of hydrogen sulfide |
| topic | hydrogen sulfide BODIPY ratiometric fluorescent probe nucleophilic reaction colorimetric |
| url | https://www.mdpi.com/1420-3049/27/21/7499 |
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