Colorimetric Carbonyl Sulfide (COS)/Hydrogen Sulfide (H2S) Donation from gamma-Ketothiocarbamate Donor Motifs

摘要

Hydrogen sulfide (H2S) is a biologically active molecule that exhibits protective effects in a variety of physiological and pathological processes. Although several H2S-related biological effects have been discovered by using H2S donors, knowing how much H2S has been released from donors under different conditions remains challenging. Now, a series of -ketothiocarbamate (gamma-KetoTCM) compounds that provide the first examples of colorimetric H2S donors and enable direct quantification of H2S release, were reported. These compounds are activated through a pH-dependent deprotonation/beta-elimination sequence to release carbonyl sulfide (COS), which is quickly converted into H2S by carbonic anhydrase. The p-nitroaniline released upon donor activation provides an optical readout that correlates directly to COS/H2S release, thus enabling colorimetric measurement of H2S donation.