Allosteric Optical Control of a Class B G-Protein-Coupled Receptor

Angew Chem Int Ed Engl. 2016 May 4;55(19):5865-8. doi: 10.1002/anie.201600957. Epub 2016 Apr 5.

Abstract

Allosteric regulation promises to open up new therapeutic avenues by increasing drug specificity at G-protein-coupled receptors (GPCRs). However, drug discovery efforts are at present hampered by an inability to precisely control the allosteric site. Herein, we describe the design, synthesis, and testing of PhotoETP, a light-activated positive allosteric modulator of the glucagon-like peptide-1 receptor (GLP-1R), a class B GPCR involved in the maintenance of glucose homeostasis in humans. PhotoETP potentiates Ca(2+) , cAMP, and insulin responses to glucagon-like peptide-1 and its metabolites following illumination of cells with blue light. PhotoETP thus provides a blueprint for the production of small-molecule class B GPCR allosteric photoswitches, and may represent a useful tool for understanding positive cooperativity at the GLP-1R.

Keywords: GLP-1 receptor; allosteric regulation; beta cells; photopharmacology; type 2 diabetes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allosteric Regulation / radiation effects
  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology*
  • Animals
  • Azo Compounds / chemistry
  • CHO Cells
  • Calcium / metabolism
  • Cell Survival / drug effects
  • Cell Survival / radiation effects
  • Cricetinae
  • Cricetulus
  • Cyclic AMP / metabolism
  • Glucagon-Like Peptide-1 Receptor / genetics
  • Glucagon-Like Peptide-1 Receptor / metabolism*
  • Humans
  • Insulin / metabolism
  • Isomerism
  • Light
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Ultraviolet Rays

Substances

  • 4-(3-(benzyloxy)phenyl)-2-(ethylsulfinyl)-6-(trifluoromethyl)pyrimidine
  • Aniline Compounds
  • Azo Compounds
  • Glucagon-Like Peptide-1 Receptor
  • Insulin
  • PhotoETP
  • Pyrimidines
  • Cyclic AMP
  • azobenzene
  • Calcium