A prospective cross-screening study on G-protein-coupled receptors: lessons learned in virtual compound library design

J Med Chem. 2012 Jun 14;55(11):5311-25. doi: 10.1021/jm300280e. Epub 2012 May 23.

Abstract

We present the systematic prospective evaluation of a protein-based and a ligand-based virtual screening platform against a set of three G-protein-coupled receptors (GPCRs): the β-2 adrenoreceptor (ADRB2), the adenosine A(2A) receptor (AA2AR), and the sphingosine 1-phosphate receptor (S1PR1). Novel bioactive compounds were identified using a consensus scoring procedure combining ligand-based (frequent substructure ranking) and structure-based (Snooker) tools, and all 900 selected compounds were screened against all three receptors. A striking number of ligands showed affinity/activity for GPCRs other than the intended target, which could be partly attributed to the fuzziness and overlap of protein-based pharmacophore models. Surprisingly, the phosphodiesterase 5 (PDE5) inhibitor sildenafil was found to possess submicromolar affinity for AA2AR. Overall, this is one of the first published prospective chemogenomics studies that demonstrate the identification of novel cross-pharmacology between unrelated protein targets. The lessons learned from this study can be used to guide future virtual ligand design efforts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine A2 Receptor Agonists / chemistry
  • Adenosine A2 Receptor Antagonists / chemistry
  • Adrenergic beta-2 Receptor Agonists / chemistry
  • Adrenergic beta-2 Receptor Antagonists / chemistry
  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Databases, Factual*
  • Drug Design*
  • Drug Partial Agonism
  • HEK293 Cells
  • High-Throughput Screening Assays
  • Humans
  • Ligands
  • Models, Molecular*
  • Molecular Structure
  • Phosphodiesterase 5 Inhibitors / chemistry
  • Piperazines / chemistry
  • Piperazines / metabolism
  • Purines / chemistry
  • Purines / metabolism
  • Quantitative Structure-Activity Relationship*
  • Radioligand Assay
  • Receptors, Adenosine A2 / chemistry*
  • Receptors, Adenosine A2 / metabolism
  • Receptors, Adrenergic, beta-2 / chemistry*
  • Receptors, Adrenergic, beta-2 / metabolism
  • Receptors, Lysosphingolipid / agonists
  • Receptors, Lysosphingolipid / chemistry*
  • Receptors, Lysosphingolipid / metabolism
  • Sildenafil Citrate
  • Stochastic Processes
  • Sulfones / chemistry
  • Sulfones / metabolism

Substances

  • Adenosine A2 Receptor Agonists
  • Adenosine A2 Receptor Antagonists
  • Adrenergic beta-2 Receptor Agonists
  • Adrenergic beta-2 Receptor Antagonists
  • Ligands
  • Phosphodiesterase 5 Inhibitors
  • Piperazines
  • Purines
  • Receptors, Adenosine A2
  • Receptors, Adrenergic, beta-2
  • Receptors, Lysosphingolipid
  • Sulfones
  • Sildenafil Citrate