N-Heterocyclic Carbene Boranes as Reactive Oxygen Species-Responsive Materials: Application to the Two-Photon Imaging of Hypochlorous Acid in Living Cells and Tissues

Yen Leng Pak, Sang Jun Park, Di Wu, Bo Hyun Cheon, Hwan Myung Kim, Jean Bouffard, Juyoung Yoon

Research output: Contribution to journalArticlepeer-review

109 Scopus citations

Abstract

N-Heterocyclic carbene (NHC) boranes undergo oxidative hydrolysis to give imidazolium salts with excellent kinetic selectivity for HOCl over other reactive oxygen species (ROS), including peroxides and peroxynitrite. Selectivity for HOCl results from the electrophilic oxidation mechanism of NHC boranes, which stands in contrast to the nucleophilic oxidation mechanism of arylboronic acids with ROS. The change in polarity that accompanies the conversion of NHC boranes to imidazolium salts can control the formation of emissive excimers, forming the basis for the design of the first fluorescence probe for ROS based on the oxidation of B−H bonds. Two-photon microscope (TPM) ratiometric imaging of HOCl in living cells and tissues is demonstrated.

Original languageEnglish
Pages (from-to)1567-1571
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number6
DOIs
StatePublished - 5 Feb 2018

Keywords

  • boron
  • fluorescence probes
  • N-heterocyclic carbenes
  • reactive oxygen species
  • two-photon microscopy

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