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Hantzsch ester modified asymmetric BODIPY probe with ultra-high sensitivity for ultra-fast detection of endogenous hypochlorite in living cells
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  • Tianli Zhu,
  • Mengting Zhao,
  • Rongcheng Wang,
  • Chenjun Dong,
  • Xuemei Dong,
  • Jie Sun,
  • Lixin Sun,
  • Chunchang Zhao
Tianli Zhu
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Mengting Zhao
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Rongcheng Wang
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Chenjun Dong
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Xuemei Dong
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Jie Sun
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Lixin Sun
East China University of Science and Technology School of Chemistry and Molecular Engineering
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Chunchang Zhao
East China University of Science and Technology School of Chemistry and Molecular Engineering

Corresponding Author:zhaocchang@ecust.edu.cn

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Abstract

Hypochlorite (ClO-) is an important reactive oxygen species produced by the immune system to fight off invading pathogens, but its over-expression can interfere with normal physiological process and induce serious diseases. Although a variety of molecular probes have been reported for detecting ClO-, the development of advanced fluorescent tools with faster response and higher sensitivity to precisely monitor ClO- remains a challenge. In this work, two Hantzsch ester (a derivative of 1,4-dihydropyridine) derived fluorescent probes MeDHP-BCl and MeDHP-PhBCl were constructed based on asymmetric BODIPY-matrix. These probes exhibit significant fluo-rescence turn-on in the ultra-sensitive (detection limit < 1 nM) and ultra-fast response (≤ 5 s) to ClO-, the reaction has determined to be a highly selective N-Chlorination of Hantzsch ester which cannot be activated by various common bioactive species, including nitric ox-ide (NO) that could oxidize Hantzsch ester under aerobic physiological conditions in most reports. MeDHP-PhBCl possess a relatively longer fluorescence emission wavelength and higher quantum yield after activation, while more notably, MeDHP-BCl displayed lower cytotoxicity and more remarkable fluorescence increasement in the response to ClO-, enabling selective and precise visualization of endogenous ClO- over-expression in living RAW264.7 cells.
22 Jul 20231st Revision Received
24 Jul 2023Submission Checks Completed
24 Jul 2023Assigned to Editor
24 Jul 2023Review(s) Completed, Editorial Evaluation Pending
27 Jul 2023Editorial Decision: Accept