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

被引：142

作者：

Pak, Yen Leng ^{[1
]}

Park, Sang Jun ^{[2
]}

Wu, Di ^{[1
]}

Cheon, BoHyun ^{[1
]}

Kim, Hwan Myung ^{[2
]}

Bouffard, Jean ^{[1
]}

Yoon, Juyoung ^{[1
]}

机构：

[1] Ewha Womans Univ, Dept Chem & Nano Sci, BK Plus 21, Seoul 03760, South Korea

[2] Ajou Univ, Dept Chem & Energy Syst Res, Suwon 443749, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

boron; fluorescence probes; N-heterocyclic carbenes; reactive oxygen species; two-photon microscopy; HYDROGEN-PEROXIDE; FLUORESCENT-PROBES; BORONATE OXIDATION; LUMINESCENT PROBES; IN-VITRO; PEROXYNITRITE; REDUCTIONS; MYELOPEROXIDASE; HYDROPEROXIDES; LIMITATIONS;

D O I：

10.1002/anie.201711188

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1567 / 1571

页数：5

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