Morningside Laboratory for Chemical Biology and Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China.
Angew Chem Int Ed Engl. 2018 Aug 6;57(32):10173-10177. doi: 10.1002/anie.201805162. Epub 2018 Jul 10.
Hydrogen peroxide (H O ) has been recognized as one of the most significant ROS (reactive oxygen species) in human health and disease. Because of the intrinsic attributes of H O -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 H O 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 H O . New H O 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 H O in living cells. In particular, starvation-induced H O 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 H O functions in biological phenomena.
过氧化氢（H2O2）已被认为是人类健康和疾病中最重要的活性氧（ROS）之一。由于 H2O2 在生理 pH 下的固有低反应性，因此开发具有高选择性和灵敏度的小分子荧光探针来可视化复杂生物环境中的 H2O2 极具挑战性。为了解决这一差距，报道了一种合理设计的串联 Payne/Dakin 反应，该反应特异性地识别 H2O2 的分子。基于这种独特的化学策略的新型 H2O2 探针可以通过一般偶联反应轻松合成，并且通过在活细胞中可视化内源性产生的 H2O2 来证实这些探针的实际适用性。特别是，通过新型探针在共聚焦成像和流式细胞术中检测到了饥饿诱导的小鼠巨噬细胞中的 H2O2 产生。这种串联 Payne/Dakin 反应为开发更复杂的分子工具来研究生物现象中的 H2O2 功能提供了基础。
