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

doi:10.1002/anie.201711188

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

Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

122 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 language	English
Pages (from-to)	1567-1571
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	6
DOIs	https://doi.org/10.1002/anie.201711188
State	Published - 5 Feb 2018

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (2012R1A3A2048814 to J.Y.; 2016R1E1A1A02920873 to H.M.K.; and 2015R1D1A1A01059383 to J.B.). We thank Dr. Sung Hong Kim of the Korean Basic Science Institute (Daegu) for EI-MS, and Dr. Su Jin Kim of the Korean Basic Science Institute (Seoul) for ESI-MS analyses.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

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

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10.1002/anie.201711188

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

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.",

keywords = "boron, fluorescence probes, N-heterocyclic carbenes, reactive oxygen species, two-photon microscopy",

author = "Pak, {Yen Leng} and Park, {Sang Jun} and Di Wu and Cheon, {Bo Hyun} and Kim, {Hwan Myung} and Jean Bouffard and Juyoung Yoon",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (2012R1A3A2048814 to J.Y.; 2016R1E1A1A02920873 to H.M.K.; and 2015R1D1A1A01059383 to J.B.). We thank Dr. Sung Hong Kim of the Korean Basic Science Institute (Daegu) for EI-MS, and Dr. Su Jin Kim of the Korean Basic Science Institute (Seoul) for ESI-MS analyses. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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N-Heterocyclic Carbene Boranes as Reactive Oxygen Species-Responsive Materials: Application to the Two-Photon Imaging of Hypochlorous Acid in Living Cells and Tissues. / Pak, Yen Leng; Park, Sang Jun; Wu, Di et al.
In: Angewandte Chemie - International Edition, Vol. 57, No. 6, 05.02.2018, p. 1567-1571.

Research output: Contribution to journal › Article › peer-review

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AU - Bouffard, Jean

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

Abstract

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