Design, Synthesis, and Cardioprotective Effects of N-Mercapto-Based Hydrogen Sulfide Donors

J Med Chem. 2015 Sep 24;58(18):7501-11. doi: 10.1021/acs.jmedchem.5b01033. Epub 2015 Sep 4.

Abstract

Hydrogen sulfide (H2S) is a signaling molecule which plays regulatory roles in many physiological and/or pathological processes. Therefore, regulation of H2S levels could have great potential therapeutic value. In this work, we report the design, synthesis, and evaluation of a class of N-mercapto (N-SH)-based H2S donors. Thirty-three donors were synthesized and tested. Our results indicated that controllable H2S release from these donors could be achieved upon structural modifications. Selected donors (NSHD-1, NSHD-2, and NSHD-6) were tested in cellular models of oxidative damage and showed significant cytoprotective effects. Moreover, NSHD-1 and NSHD-2 were also found to exhibit potent protective effects in a murine model of myocardial ischemia reperfusion (MI/R) injury.

Publication types

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

MeSH terms

  • Animals
  • Benzamides / chemical synthesis
  • Benzamides / chemistry
  • Benzamides / pharmacology
  • Cardiotonic Agents / chemical synthesis
  • Cardiotonic Agents / chemistry*
  • Cardiotonic Agents / pharmacology
  • Cell Line
  • Drug Design
  • Heart Ventricles / cytology
  • Hydrogen Peroxide / pharmacology
  • Hydrogen Sulfide / metabolism*
  • L-Lactate Dehydrogenase / metabolism
  • Male
  • Membrane Potential, Mitochondrial / drug effects
  • Mice, Inbred C57BL
  • Myoblasts, Cardiac / cytology
  • Myoblasts, Cardiac / drug effects
  • Myocardial Reperfusion Injury / drug therapy
  • Oxidative Stress
  • Rats
  • Structure-Activity Relationship
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Compounds / pharmacology

Substances

  • Benzamides
  • Cardiotonic Agents
  • Sulfhydryl Compounds
  • Hydrogen Peroxide
  • L-Lactate Dehydrogenase
  • Hydrogen Sulfide