Molecular modeling of adenosine receptors. The ligand binding site on the rat adenosine A2A receptor

Eur J Pharmacol. 1994 Jun 15;268(1):95-104. doi: 10.1016/0922-4106(94)90124-4.

Abstract

The amino acid sequence of the rat adenosine A2A receptor and the atomic coordinates of bacteriorhodopsin were combined to generate a three-dimensional model for the adenosine A2A receptor. This model consists of seven amphipathic alpha-helices, forming a pore that is rather hydrophilic compared to the hydrophobic outside of the protein. Subsequently, a highly potent and selective ligand for this receptor, 2-(cyclohexylmethylidinehydrazino)adenosine (SHA 174), was docked into this cavity. A binding site is proposed that takes into account the conformational characteristics of the ligand. Moreover, it involves two histidine residues that were shown to be important for ligand coordination from chemical modification studies. Subsequently, the deduced binding site was used to model other potent ligands, including 8-(3-chlorostyryl)caffeine, a new A2-selective antagonist, that could all be accommodated consistent with earlier biochemical and pharmacological findings. Finally, some thoughts on how adenosine receptor activation might proceed are put forward, based on structural analogies with the enzyme family of serine proteases.

MeSH terms

  • Adenosine / metabolism
  • Amino Acid Sequence
  • Animals
  • Bacteriorhodopsins / metabolism
  • Binding Sites
  • Computer Simulation
  • Ligands
  • Models, Molecular
  • Molecular Sequence Data
  • Protein Conformation
  • Purinergic P1 Receptor Agonists
  • Rats
  • Receptors, Purinergic P1 / chemistry*
  • Receptors, Purinergic P1 / metabolism
  • Thermodynamics

Substances

  • Ligands
  • Purinergic P1 Receptor Agonists
  • Receptors, Purinergic P1
  • Bacteriorhodopsins
  • Adenosine