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Tandem Payne/Dakin Reaction: A New Strategy for Hydrogen Peroxide Detection and Molecular Imaging
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-07-10 , DOI: 10.1002/anie.201805162
Sen Ye 1 , Jun Jacob Hu 1 , Dan Yang 1
Affiliation  

Hydrogen peroxide (H2O2) has been recognized as one of the most significant ROS (reactive oxygen species) in human health and disease. Because of the intrinsic attributes of H2O2—such as its low reactivity under physiological pH—it is exceedingly challenging to develop small‐molecule fluorescent probes with high selectivity and sensitivity for visualization of H2O2 in an intricate biological milieu. To address this gap, a rationally designed tandem Payne/Dakin reaction is reported that is specific to molecular recognition of H2O2. New H2O2 probes based on this unique chemical strategy can be easily synthesized by a general coupling reaction, and the practical applicability of those probes has been confirmed by the visualization of endogenously produced H2O2 in living cells. In particular, starvation‐induced H2O2 production in mouse macrophages has been detected by the novel probe in both confocal imaging and flow cytometry. This tandem Payne/Dakin reaction provides a basis for developing more sophisticated molecular tools to interrogate H2O2 functions in biological phenomena.

中文翻译:

串联Payne / Dakin反应:过氧化氢检测和分子成像的新策略

过氧化氢(H 2 O 2)被公认为是人类健康和疾病中最重要的ROS(活性氧)之一。由于H 2 O 2的固有属性(例如在生理pH下的低反应性),开发具有高选择性和灵敏度的小分子荧光探针以在复杂的生物环境中可视化H 2 O 2极具挑战性。为了解决这个空白,据报道合理设计的串联Payne / Dakin反应对H 2 O 2的分子识别是特定的。新H 2 O 2可以通过一般的偶联反应轻松合成基于这种独特化学策略的探针,并且通过可视化活细胞中内源产生的H 2 O 2证实了这些探针的实际适用性。特别是,在共聚焦成像和流式细胞术中,这种新型探针已检测到饥饿诱导的小鼠巨噬细胞中H 2 O 2的产生。这种串联的Payne / Dakin反应为开发更复杂的分子工具以探究生物现象中的H 2 O 2功能提供了基础。
更新日期:2018-07-10
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