Insights into soluble guanylyl cyclase activation derived from improved heme-mimetics

J Med Chem. 2013 Nov 14;56(21):8948-8952. doi: 10.1021/jm400539d. Epub 2013 Oct 24.

Abstract

Recently, the structure of BAY 58-2667 bound to the Nostoc sp. H-NOX domain was published. On the basis of this structural information, we designed BAY 58-2667 derivatives and tested their effects on soluble guanylyl cyclase (sGC) activity. Derivative 20 activated sGC 4.8-fold more than BAY 58-2667. Co-crystallization of 20 with the Ns H-NOX domain revealed that the increased conformational distortion at the C-terminal region of αF helix containing 110-114 residues contributes to the higher activation triggered by 20.

Publication types

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

MeSH terms

  • Benzoates / chemical synthesis
  • Benzoates / chemistry
  • Benzoates / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design
  • Enzyme Activation
  • Guanylate Cyclase / metabolism*
  • Heme / chemistry
  • Heme / metabolism*
  • Models, Molecular
  • Molecular Conformation / drug effects
  • Nitric Oxide / metabolism
  • Nostoc / enzymology
  • Receptors, Cytoplasmic and Nuclear / agonists
  • Receptors, Cytoplasmic and Nuclear / metabolism*
  • Soluble Guanylyl Cyclase
  • Structure-Activity Relationship

Substances

  • Benzoates
  • Receptors, Cytoplasmic and Nuclear
  • Nitric Oxide
  • BAY 58-2667
  • Heme
  • Guanylate Cyclase
  • Soluble Guanylyl Cyclase

Associated data

  • PDB/4JQH