Colorimetric Carbonyl Sulfide (COS)/Hydrogen Sulfide (H2 S) Donation from γ-Ketothiocarbamate Donor Motifs

Angew Chem Int Ed Engl. 2018 Oct 1;57(40):13101-13105. doi: 10.1002/anie.201806854. Epub 2018 Sep 4.

Abstract

Hydrogen sulfide (H2 S) is a biologically active molecule that exhibits protective effects in a variety of physiological and pathological processes. Although several H2 S-related biological effects have been discovered by using H2 S donors, knowing how much H2 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 H2 S donors and enable direct quantification of H2 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 H2 S by carbonic anhydrase. The p-nitroaniline released upon donor activation provides an optical readout that correlates directly to COS/H2 S release, thus enabling colorimetric measurement of H2 S donation.

Keywords: anti-inflammation; carbonyl sulfide; colorimetry; hydrogen sulfide; γ-ketothiocarbamate.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aniline Compounds / chemistry
  • Animals
  • Carbamates / chemistry*
  • Carbamates / toxicity
  • Carbonic Anhydrases / metabolism
  • Cell Survival / drug effects
  • Colorimetry*
  • HeLa Cells
  • Humans
  • Hydrogen Sulfide / chemistry*
  • Hydrogen Sulfide / metabolism
  • Mice
  • Microscopy, Fluorescence
  • Oxygen / chemistry
  • RAW 264.7 Cells
  • Sulfur Oxides / chemistry*
  • Sulfur Oxides / metabolism

Substances

  • Aniline Compounds
  • Carbamates
  • Sulfur Oxides
  • nitroaniline
  • carbonyl sulfide
  • Carbonic Anhydrases
  • Oxygen
  • Hydrogen Sulfide