Chemiluminescent Probes for Activity-Based Sensing of Formaldehyde Released from Folate Degradation in Living Mice.
Chemiluminescent Probes for Activity-Based Sensing of Formaldehyde Released from Folate Degradation in Living Mice.
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DOI：
10.1002/anie.201802143
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发表时间：
2018-06-18
期刊：
影响因子：
--
通讯作者：
Chang CJ
中科院分区：
文献类型：
--
作者：
Bruemmer KJ;Green O;Su TA;Shabat D;Chang CJ
甲醛(FA)是一种常见的环境毒素，也是一种在体内通过广泛的代谢和表观遗传过程自然产生的毒素，推动了新技术的发展，以监测生命系统中的这种活性羰基物种(RCS)。在这里，我们报告了一对第一代化学发光探针，用于选择性检测甲醛。用通用的2-氮杂环己烷反应甲醛触发器笼化含有不同吸电子基团的苯氧基二氧杂环己烷支架，提供了化学发光甲醛探针540和700(CFAP540和CFAP700)，分别用于可见和近红外检测活细胞和小鼠中的甲醛。特别是，CFAP700能够可视化内源性叶酸代谢产生的FA释放，为使用CFAP和相关化学工具探测FA的生理和病理以及开发可用于从体外生化到细胞再到动物模型的更广泛的化学发光活性传感(ABS)探针提供了一个起点。通信第一代基于活性的化学发光传感探针用于体内甲醛成像。甲醛选择性触发器被用来囚禁苯酚-二氧杂环己烷支架，该支架在依赖氮杂环己烷去势后会发出光子。这些试剂被用来对活细胞和小鼠体内的甲醛通量进行成像，从而能够唯一地识别体内代谢叶酸循环产生的内源性甲醛。
Formaldehyde (FA) is a common environmental toxin that is also produced naturally in the body through a wide range of metabolic and epigenetic processes, motivating the development of new technologies to monitor this reactive carbonyl species (RCS) in living systems. Here, we report a pair of first-generation chemiluminescent probes for selective formaldehyde detection. Caging phenoxy-dioxetane scaffolds bearing different electron-withdrawing groups with a general 2-aza-Cope reactive formaldehyde trigger provides Chemiluminescent Formaldehyde Probes 540 and 700 (CFAP540 and CFAP700) for visible and near-IR detection of FA in living cells and mice, respectively. In particular, CFAP700 is capable of visualizing FA release derived from endogenous folate metabolism, providing a starting point for the use of CFAPs and related chemical tools to probe FA physiology and pathology, as well as for the development of a broader palette of chemiluminescent activity-based sensing (ABS) probes that can be employed from in vitro biochemical to cell to animal models. COMMUNICATION A first-generation set of chemiluminescent activity-based sensing probes for in vivo imaging of formaldehyde is reported. A formaldehyde-selective trigger is used to cage a phenol-dioxetane scaffold that emits a photon after aza-Cope-dependent uncaging. These reagents were utilized to image formaldehyde fluxes in living cells and mice, enabling the unique identification of endogenous formaldehyde production from metabolic folate cycles in vivo.
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