A mitochondria-targeted ratiometric fluorescent probe to monitor endogenously generated sulfur dioxide derivatives in living cells |
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| Affiliation: | 1. Department of Chemistry & Med Chem Program, National University of Singapore, 117543, Singapore;2. Singapore Peking Oxford Research Enterprise (SPORE), Environmental Research Institute (NERI), 5A Engineering Drive 1, #02-01, 117411, Singapore;3. Singapore Bioimaging Consortium, Agency for Science, Technology and Research (A*STAR), 138667, Singapore;4. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, PR China;1. Department of Chemistry (Centre of Advanced Study), Faculty of Science, Banaras Hindu University, Varanasi, Uttar Pradesh 221005, India;2. Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR–National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, India;3. Department of Zoology (Centre of Advanced Study), Faculty of Science, Banaras Hindu University, Varanasi 221005, India;1. Institute of Veterinary Drug, Jiangxi Agricultural University/Jiangxi Provincial Key Laboratory for Animal Health, Nanchang 330045, China;2. School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China;1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an 710069, PR China;2. College of Life Sciences, Northwest University, Xi’an 710069, PR China;1. School of Environmental and Chemical Engineering, North China Electric Power University, Beijing 102206, People’s Republic of China;2. Institute of Intelligent Machines, Chinese Academy of Sciences, Hefei, Anhui 230031, People’s Republic of China;3. State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People’s Republic of China;4. Department of Materials Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, People’s Republic of China;1. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry & Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China;2. College of Fisheries, Huazhong Agricultural University, Wuhan 430070, China;1. College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121013, China;2. College of Laboratory Medicine, Dalian Medical University, Dalian 116044, China;3. School of International Education, Beijing University of Chemical Technology, Beijing 100029, China |
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| Abstract: | Sulfur dioxide (SO2) can be endogenously produced by enzymes in mitochondria during oxidation of H2S or sulphur-containing amino acids, and plays important roles in several physiological processes. However, the design and synthesis of fluorescent probes which can detect mitochondrial SO2 and its derivatives in living cells still remain unresolved. Herein, we report the preparation of a lipophilic cationic dye 1 (Mito-Ratio-SO2), which targets the mitochondria in living cells and is sensitive to the presence of SO2 derivatives. The ratiometric probe Mito-Ratio-SO2 displays a 170 nm blue-shift in emission with two well-resolved emission bands upon addition of sulfite. Mechanistic studies indicate that three probe-SO2 adducts coexist after reaction, as supported by liquid chromatography and density function theory investigations. Importantly, the ratiometric probe is highly selective for sulfite over other bio-species including H2S. Fluorescence co-localization studies indicate that the probe localizes solely in the mitochondria of HeLa cells. Last but not least, fluorescent imaging of HeLa cells successfully demonstrates the detection of intrinsically generated intracellular SO2 derivatives in living cells. |
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| Keywords: | Ratiometric fluorescent probe Endogenous sulfur dioxide Intramolecular charge transfer Mitochondria Living cell imaging |
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