Department of Chemistry and Biochemistry, Institute of Molecular Biology, and Materials Science Institute, University of Oregon, Eugene, OR, 97403, USA.
Angew Chem Int Ed Engl. 2018 Oct 1;57(40):13101-13105. doi: 10.1002/anie.201806854. Epub 2018 Sep 4.
Hydrogen sulfide (H S) is a biologically active molecule that exhibits protective effects in a variety of physiological and pathological processes. Although several H S-related biological effects have been discovered by using H S donors, knowing how much H S has been released from donors under different conditions remains challenging. Now, a series of γ-ketothiocarbamate (γ-KetoTCM) compounds that provide the first examples of colorimetric H S donors and enable direct quantification of H S release, were reported. These compounds are activated through a pH-dependent deprotonation/β-elimination sequence to release carbonyl sulfide (COS), which is quickly converted into H S by carbonic anhydrase. The p-nitroaniline released upon donor activation provides an optical readout that correlates directly to COS/H S release, thus enabling colorimetric measurement of H S donation.
硫化氢 (H₂S) 是一种具有生物活性的分子，在多种生理和病理过程中表现出保护作用。尽管已经使用 H₂S 供体发现了几种 H₂S 相关的生物学效应，但要了解在不同条件下从供体中释放了多少 H₂S 仍然具有挑战性。现在，报道了一系列γ-酮硫代氨基甲酸盐 (γ-KetoTCM) 化合物，它们为显色 H₂S 供体提供了首例，并能够直接定量 H₂S 的释放。这些化合物通过 pH 依赖性去质子化/β-消除序列被激活，释放出碳酰硫化物 (COS)，后者很快被碳酸酐酶转化为 H₂S。供体激活时释放的对硝基苯胺提供了光学读出，与 COS/H₂S 释放直接相关，从而能够进行显色测量 H₂S 的供体。
