A Binding Site on IL-17A for Inhibitory Macrocycles Revealed by Hydrogen/Deuterium Exchange Mass Spectrometry

J Med Chem. 2016 Mar 10;59(5):2255-60. doi: 10.1021/acs.jmedchem.5b01693. Epub 2016 Feb 18.

Abstract

Computational assessment of the IL-17A structure identified two distinct binding pockets, the β-hairpin pocket and the α-helix pocket. The β-hairpin pocket was hypothesized to be the site of binding for peptide macrocycles. Support for this hypothesis was obtained using HDX-MS which revealed protection to exchange only within the β-hairpin pocket. This data represents the first direct structural evidence of a small molecule binding site on IL-17A that functions to disrupt the interaction with its receptor.

MeSH terms

  • Binding Sites / drug effects
  • Deuterium Exchange Measurement*
  • Dose-Response Relationship, Drug
  • Humans
  • Interleukin-17 / antagonists & inhibitors*
  • Interleukin-17 / metabolism
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry
  • Macrocyclic Compounds / pharmacology*
  • Mass Spectrometry*
  • Models, Molecular
  • Molecular Conformation
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology*
  • Structure-Activity Relationship

Substances

  • IL17A protein, human
  • Interleukin-17
  • Macrocyclic Compounds
  • Peptides, Cyclic