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 PakSang Jun ParkDi WuBoHyun CheonHwan Myung KimJean BouffardJuyoung YoonPublished in: Angewandte Chemie (International ed. in English) (2018)
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.
Keyphrases
- living cells
- reactive oxygen species
- fluorescent probe
- ionic liquid
- single molecule
- high resolution
- hydrogen peroxide
- gene expression
- electron transfer
- computed tomography
- nitric oxide
- oxidative stress
- visible light
- contrast enhanced
- photodynamic therapy
- energy transfer
- mass spectrometry
- structural basis
- light emitting