Molecular engineering of ultra-sensitive fluorescent probe with large Stokes shift for imaging of basal HOCl in tumor cells and tissues |
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| Institution: | 1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China;2. Lab of Biosystem and Microanalysis, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China;1. State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, PR China;2. College of Environmental and Engineering, Nanchang Hangkong University, Nanchang 330063, PR China;1. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, National Demonstration Center for Experimental Chemistry Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710127, PR China;2. School of Automation, Xi’an University of Posts and Telecommunications, Xi’an 710121, PR China;1. Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, College of Biology, Collaborative Innovation Center for Chemistry and Molecular Medicine, Hunan University, Changsha 410082, PR China;2. College of Materials and Chemical Engineering, Hunan City University, Yiyang 413000, PR China;3. College of Life Sciences, Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Bio-Sensing and Chemometric, College of Chemistry and Chemical Engineering, Aptamer Engineering Center of Hunan Province, Hunan University, Changsha 410082, PR China, PR China |
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| Abstract: | Fluorescent probes have been widely employed in biological imaging and sensing. However, it is always a challenge to design probes with high sensitivity. In this work, based on rhodamine skeleton, we developed a general strategy to construct sensitivity-enhanced fluorescent probe with the help of theoretical calculation for the first time. As a proof of concept, we synthesized a series of HOCl probes. Experiment results showed that with the C-9 of pyronin moiety of rhodamine stabilized by an electron donor group, probe DQF-S exhibited an importantly enhanced sensitivity (LOD: 0.2 nmol/L) towards HOCl together with fast response time (<10 s). Moreover, due to the breaking symmetrical electron distribution by another electron donor group, the novel rhodamine probe DQF-S displayed a far red to near-infrared emission (>650 nm) and large Stokes shift. Bioimaging studies indicated that DQF-S can not only effectively detect basal HOCl in various types of cells, but also be successfully applied to image tumor tissue in vivo. These results demonstrate the potential of our design as a useful strategy to develop excellent fluorescent probes for bioimaging. |
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| Keywords: | Fluorescent probes High sensitivity Hypochlorous acid (HOCl) Large Stokes shift Fluorescence imaging |
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