Self-Immolative Thiocarbamates Provide Access to Triggered H2S Donors and Analyte Replacement Fluorescent Probes.
Self-Immolative Thiocarbamates Provide Access to Triggered H2S Donors and Analyte Replacement Fluorescent Probes.
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DOI：
10.1021/jacs.6b03780
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发表时间：
2016-06-15
影响因子：
15
通讯作者：
Pluth MD
中科院分区：
文献类型：
--
作者：
Steiger AK;Pardue S;Kevil CG;Pluth MD
硫化氢 (H2S) 是一种重要的生物信号分子，用于 H2S 传递和检测的化学工具已成为重要的研究方法。这些领域的主要挑战包括开发响应刺激而触发释放 H2S 的供体以及开发不会不可逆消耗 H2S 的探针。在这里，我们报告了一种基于硫代氨基甲酸苄酯自焚释放硫化羰的新的硫化氢贡献策略，硫化羰被碳酸酐酶快速转化为硫化氢。我们利用这种化学反应来开发易于修改的供体，这些供体可以被触发释放 H2S。我们还证明，这种方法可以与常见的 H2S 传感基序结合生成支架，该支架在与 H2S 反应时产生荧光响应，并释放笼中的 H2S，从而解决基于反应的探针中分析物稳态的挑战。
Hydrogen sulfide (H2S) is an important biological signaling molecule, and chemical tools for H2S delivery and detection have emerged as important investigative methods. Key challenges in these fields include developing donors that are triggered to release H2S in response to stimuli and developing probes that do not irreversibly consume H2S. Here we report a new strategy for H2S donation based on self-immolation of benzyl thiocarbamates to release carbonyl sulfide, which is rapidly converted to H2S by carbonic anhydrase. We leverage this chemistry to develop easily modifiable donors that can be triggered to release H2S. We also demonstrate that this approach can be coupled with common H2S-sensing motifs to generate scaffolds which, upon reaction with H2S, generate a fluorescence response and also release caged H2S, thus addressing challenges of analyte homeostasis in reaction-based probes.