Synthesis of bivalent beta2-adrenergic and adenosine A1 receptor ligands

J Med Chem. 2008 Oct 9;51(19):6128-37. doi: 10.1021/jm800613s. Epub 2008 Sep 11.

Abstract

Research in the area of simutaneously targeting more than one G protein-coupled receptor (GPCR) has increased in recent times. By exploiting the cross talk between the beta2-adrenergic (beta2AR) and adenosine A1 receptors (A1AR) on adenylate cyclase activity, we synthesized a series of bivalent agonists for both GPCRs to generate responses from more than one receptor. We have demonstrated a relationship between the various beta2-adrenergic and A1 adenosine bivalent parameters of linker and bifunctionality by using data that are drawn from in vitro assays. The hexyl-linked 12e (K(i), 311 nM) and butyl-linked 12c ( K(i), 863 nM) bivalent compounds displayed reasonable binding affinities for the beta2AR when compared with the control (-)isoproterenol (K(i), 136 nM), and both compounds also exhibited a persuasive bifunctional trend for both receptors at various drug concentrations. The bivalent compound 12e was also found to have significant EC50 potency (6 nM) at the beta2AR in DDT cells.

MeSH terms

  • Adenosine A1 Receptor Agonists*
  • Adrenergic beta-2 Receptor Agonists*
  • Animals
  • Binding Sites
  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Carbamates / pharmacology*
  • Cricetinae
  • Crystallography, X-Ray
  • Cyclic AMP / analysis
  • Cyclic AMP / metabolism
  • Dose-Response Relationship, Drug
  • Formamides / chemical synthesis*
  • Formamides / chemistry
  • Formamides / pharmacology*
  • Isoproterenol / pharmacology
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Adenosine A1 Receptor Agonists
  • Adrenergic beta-2 Receptor Agonists
  • Carbamates
  • Formamides
  • Ligands
  • Cyclic AMP
  • Isoproterenol