7TM X-ray structures for class C GPCRs as new drug-discovery tools. 1. mGluR5

Bioorg Med Chem Lett. 2016 Jan 15;26(2):484-494. doi: 10.1016/j.bmcl.2015.11.087. Epub 2015 Nov 25.

Abstract

We illustrate, with a focus on mGluR5, how the recently published, first X-ray structures of mGluR 7TM domains, specifically those of mGluR1 and mGluR5 complexed with negative allosteric modulators (NAMs), will begin to influence ligand- (e.g., drug- or sweetener-) discovery efforts involving class C GPCRs. With an extensive docking study allowing full ligand flexibility and full side chain flexibility of all residues in the ligand-binding cavity, we have predicted and analyzed the binding modes of a variety of structurally diverse mGluR5 NAM ligands, showing how the X-ray structures serve to effectively rationalize each ligand's binding characteristics. We demonstrated that the features that are inherent in our earlier overlay model are preserved in the protein structure-based docking models. We identified structurally diverse compounds, which potentially act as mGluR NAMs, and revealed binding-site differences by performing high-throughput docking using a database of approximately six million structures of commercially available compounds and the mGluR1 and mGluR5 X-ray structures. By comparing the 7TM domains of the mGluR5 and mGluR1 X-rays structures, we identified selectivity factors within group I of the mGluRs. Similarly, using homology models that we built for mGluR2 and mGluR4, we have identified the factors leading to the selectivity between group I and groups II and III for ligands occupying the deepest portion of the mGluR5 binding cavity. Finally, we have proposed a structure-based explanation of the pharmacological switching within a set of positive allosteric modulators (PAMs) and their corresponding, very close NAM analogs.

Keywords: Computer-aided drug discovery; Docking; Mavoglurant; Metabotropic glutamate receptors (mGluRs); Negative allosteric modulators (NAMs); Positive allosteric modulators (PAMs); Structure-based drug design; X-ray structure.

MeSH terms

  • Benzamides / chemistry
  • Binding Sites
  • Crystallography, X-Ray*
  • Drug Discovery / methods*
  • Indoles / chemistry
  • Ligands
  • Models, Molecular
  • Molecular Docking Simulation
  • Molecular Structure
  • Protein Domains
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Pyridines / chemistry
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Receptor, Metabotropic Glutamate 5 / agonists
  • Receptor, Metabotropic Glutamate 5 / antagonists & inhibitors
  • Receptor, Metabotropic Glutamate 5 / chemistry*
  • Thiazoles / chemistry
  • Triazines / chemistry
  • Triazoles / chemistry

Substances

  • 3-chloro-4-fluoro-5-(6-(1H-pyrazol-1-yl)pyrimidin-4-yl)benzonitrile
  • 3-chloro-5-(6-(5-fluoropyridin-2-yl)pyrimidin-4-yl)benzonitrile
  • 4-fluoro-N-(4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl)-N-methylbenzamide
  • Benzamides
  • Indoles
  • Ligands
  • Pyrazoles
  • Pyridines
  • Pyrimidines
  • Receptor, Metabotropic Glutamate 5
  • Thiazoles
  • Triazines
  • Triazoles
  • ZM 241385
  • 6-methyl-2-(phenylethynyl)pyridine
  • mavoglurant