The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides.
The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides.
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DOI：
10.1002/anie.201506887
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发表时间：
2015-11-16
期刊：
影响因子：
--
通讯作者：
Xian M
中科院分区：
文献类型：
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作者：
Chen W;Rosser EW;Matsunaga T;Pacheco A;Akaike T;Xian M
内源性多硫化氢（H2Sn, n > 1）已被认为是硫相关氧化还原生物学的重要调节因子。H2Sn对肿瘤抑制因子、离子通道和转录因子的激活作用强于H2S。虽然H2Sn引起了越来越多的关注，但它们的确切作用机制仍然知之甚少。该领域的一个主要障碍是缺乏可靠和方便的H2Sn检测方法。在这项工作中，我们报道了h2sn在温和条件下介导的苯二噻吩酮的形成。该反应利用了H2Sn作为亲核试剂和亲电试剂的独特双反应性。它为更好地理解H2Sn的化学生物学打开了一扇门。在此基础上合成了3个荧光探针（PSP-1~3）并进行了评价。在所制备的探针中，PSP-3对H2Sn具有良好的关闭荧光响应和高特异性。它成功地应用于细胞内H2Sn的可视化。
Endogenous hydrogen polysulfides (H2Sn, n > 1) have been recognized as important regulators in sulfur-related redox biology. H2Sn can activate tumor suppressors, ion channels, and transcription factors with higher potency than H2S. While H2Sn are drawing increasing attention, their exact mechanisms of actions are still poorly understood. A major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. In this work we report a H2Sn-mediated benzodithiolone formation under mild conditions. This reaction takes advantage of the unique dual-reactivity of H2Sn as both a nucleophile and an electrophile. It opens a door for better understanding H2Sn's chemical biology. Based on this reaction, three fluorescent probes (PSP-1~3) were synthesized and evaluated. Among the probes prepared, PSP-3 showed a desirable off-on fluorescence response to H2Sn and high specificity. It was successfully applied in visualizing intracellular H2Sn.