NO-independent regulatory site of direct sGC stimulators like YC-1 and BAY 41-2272

BMC Pharmacol. 2001:1:13. doi: 10.1186/1471-2210-1-13. Epub 2001 Dec 28.

Abstract

Background: The most important receptor for nitric oxide is the soluble guanylate cyclase (sGC), a heme containing heterodimer. Recently, a pyrazolopyridine derivative BAY 41-2272, structurally related to YC-1, was identified stimulating soluble guanylate cyclase in an NO-independent manner, which results in vasodilatation and antiplatelet activity. The study described here addresses the identification of the NO-independent site on soluble guanylate cyclase.

Results: We developed a photoaffinity label (3H-meta-PAL) for the direct and NO-independent soluble guanylate cyclase (sGC) stimulator BAY 41-2272 by introducing an azido-group into the tritium labeled compound. The synthesized photoaffinitylabel directly stimulates the purified sGC and shows in combination with NO a synergistic effect on sGC activity. Irradiation with UV light of 3H-meta-PAL together with the highly purified sGC leads to a covalent binding to the alpha1-subunit of the enzyme. This binding is blocked by unlabeled meta-PAL, YC-1 and BAY 41-2272. For further identification of the NO-independent regulatory site the 3H-meta-PAL labeled sGC was fragmented by CNBr digest. The 3H-meta-PAL binds to a CNBr fragment, consisting of the amino acids 236-290 of the alpha1-subunit. Determination of radioactivity of the single PTH-cycles from the sequencing of this CNBr fragment detected the cysteines 238 and 243 as binding residues of the 3H-meta-PAL.

Conclusions: Our data demonstrate that the region surrounding the cysteines 238 and 243 in the alpha1-subunit of the sGC could play an important role in regulation of sGC activity and could be the target of this new type of sGC stimulators.

MeSH terms

  • Animals
  • Cells, Cultured
  • Enzyme Activation
  • Enzyme Activators / pharmacology*
  • Guanylate Cyclase / genetics
  • Guanylate Cyclase / metabolism*
  • Indazoles / pharmacology*
  • Insecta / cytology
  • Nitric Oxide / metabolism*
  • Photoaffinity Labels
  • Pyrazoles / pharmacology*
  • Pyridines / pharmacology*
  • Recombinant Proteins / drug effects
  • Recombinant Proteins / metabolism

Substances

  • 3-(4-Amino-5-cyclopropylpyrimidine-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo(3,4-b)pyridine
  • Enzyme Activators
  • Indazoles
  • Photoaffinity Labels
  • Pyrazoles
  • Pyridines
  • Recombinant Proteins
  • 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole
  • Nitric Oxide
  • Guanylate Cyclase