Unusual Hypochlorous Acid (HClO) Recognition Mechanism Based on Chlorine–Oxygen Bond (Cl?O) Formation |
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| Authors: | Jianlong Ma Chaoxian Yan Yijing Li Huixiao Duo Qiang Li Xiaofeng Lu Prof Yong Guo |
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| Affiliation: | 1. Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
University of Chinese Academy of Sciences, Beijing, 100049 P. R. China;2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 P. R. China;3. Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 P. R. China;4. Key Laboratory of Heavy Ion Radiation Biology and Medicine of, Chinese Academy of Sciences, Institute of Modern Physics, Lanzhou, 730000 P. R. China |
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| Abstract: | One of the most important endogenous reactive oxygen species, hypochlorous acid (HClO), is involved in numerous pathological and physiological processes. Herein, a near-infrared fluorescence probe (CyHR) was designed and synthesized for ultrafast (within 0.2 s), sensitive (limit of detection=39.44 nm ), and selective response to HClO. The reaction mechanism was systematically analyzed by MS, 1H NMR spectroscopy, HPLC-MS techniques, and theoretical calculations. The results indicated that HClO can be recognized by CyHR, which is based on chlorine–oxygen (Cl?O) bond formation. To the best of our knowledge, this study is the first to find Cl?O bonds among organic aromatic compounds, given that Cl?O bonds are common among inorganics. Through biological experiments, CyHR was successfully applied to image exogenous and endogenous HClO in macrophage cells (RAW 264.7). Thus, CyHR is a promising tool for HClO-related physiological and pathological studies and may provide a means for designing HClO-specific fluorescence probes. |
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| Keywords: | chlorine–oxygen bond fluorescence probes hypochlorous acid near-infrared fluorescence bioimaging |
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