N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues,Angewandte Chemie International Edition

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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
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-01-09 , DOI: 10.1002/anie.201711188
Yen Leng Pak ₁ , Sang Jun Park ₂ , Di Wu ₁ , BoHyun Cheon ₁ , Hwan Myung Kim ₂ , Jean Bouffard ₁ , Juyoung Yoon ₁

Affiliation

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.

中文翻译：

N-杂环碳硼烷作为活性氧的响应材料：在活细胞和组织中次氯酸的双光子成像中的应用

N-杂环卡宾（NHC）硼烷经过氧化水解，生成的咪唑鎓盐对HOCl的动力学选择性优于其他活性氧（ROS），包括过氧化物和过氧亚硝酸盐。HOCl的选择性是由NHC硼烷的亲电氧化机理引起的，这与芳基硼酸与ROS的亲核氧化机理相反。NHC硼烷转化为咪唑鎓盐时伴随的极性变化可以控制发射态受激准分子的形成，从而为基于B-H键氧化的ROS荧光探针的设计奠定了基础。证明了活细胞和组织中HOCl的双光子显微镜（TPM）比例成像。

更新日期：2018-01-09

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