Development of Potent and Selective Antagonists for the UTP-Activated P2Y4 Receptor

J Med Chem. 2017 Apr 13;60(7):3020-3038. doi: 10.1021/acs.jmedchem.7b00030. Epub 2017 Mar 30.

Abstract

P2Y4 is a Gq protein-coupled receptor activated by uridine-5'-triphosphate (UTP), which is widely expressed in the body, e.g., in intestine, heart, and brain. No selective P2Y4 receptor antagonist has been described so far. Therefore, we developed and optimized P2Y4 receptor antagonists based on an anthraquinone scaffold. Potency was assessed by a fluorescence-based assay measuring inhibition of UTP-induced intracellular calcium release in 1321N1 astrocytoma cells stably transfected with the human P2Y4 receptor. The most potent compound of the present series, sodium 1-amino-4-[4-(2,4-dimethylphenylthio)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (PSB-16133, 61) exhibited an IC50 value of 233 nM, selectivity versus other P2Y receptor subtypes, and is thought to act as an allosteric antagonist. A receptor homology model was built and docking studies were performed to analyze ligand-receptor interactions. Compound 64 (PSB-1699, sodium 1-amino-4-[4-(3-pyridin-3-ylmethylthio)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate) represents the most selective P2Y4 receptor antagonist known to date. Compounds 61 and 64 are therefore anticipated to become useful tools for studying this scarcely investigated receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry*
  • Anthraquinones / pharmacology*
  • Drug Discovery
  • Humans
  • Molecular Docking Simulation
  • Purinergic P2 Receptor Antagonists / chemistry*
  • Purinergic P2 Receptor Antagonists / pharmacology*
  • Receptors, Purinergic P2 / chemistry
  • Receptors, Purinergic P2 / metabolism*
  • Structure-Activity Relationship
  • Uridine Triphosphate / metabolism*

Substances

  • Anthraquinones
  • Purinergic P2 Receptor Antagonists
  • Receptors, Purinergic P2
  • purinoceptor P2Y4
  • Uridine Triphosphate