Molecular modeling of adenosine receptors. I. The ligand binding site on the A1 receptor

Drug Des Discov. 1992;9(1):49-67.

Abstract

The amino acid sequence of the canine adenosine A1 receptor and the atomic coordinates of a structurally related protein, bacteriorhodopsin, were combined to generate a three-dimensional model for the adenosine A1 receptor. This model consists of seven amphipathic alpha-helices, forming a pore that has a rather distinct partition between hydrophobic and hydrophilic regions. Subsequently, a highly potent and selective ligand, N6-cyclopentyladenosine, was docked into this cavity. A binding site is proposed that takes into account the conformational characteristics of the ligand, obtained from indirect modeling studies by the 'active analog approach'. Moreover, it involves two histidine residues that were shown to be important for ligand coordination from chemical modification studies. Finally, the deduced binding site was used to model other potent ligands that could all be accommodated consistent with earlier biochemical and pharmacological findings.

MeSH terms

  • Adenosine / analogs & derivatives
  • Adenosine / chemistry
  • Amino Acid Sequence
  • Animals
  • Bacteriorhodopsins / chemistry
  • Dogs
  • GTP-Binding Proteins / chemistry
  • Histidine / chemistry
  • Ligands
  • Models, Chemical*
  • Models, Molecular*
  • Molecular Sequence Data
  • Protein Binding
  • Receptors, Purinergic / chemistry*
  • Xanthines / pharmacology

Substances

  • Ligands
  • Receptors, Purinergic
  • Xanthines
  • N(6)-cyclopentyladenosine
  • Histidine
  • Bacteriorhodopsins
  • 1,3-dipropyl-8-cyclopentylxanthine
  • GTP-Binding Proteins
  • Adenosine