Targeting lysine specific demethylase 4A (KDM4A) tandem TUDOR domain - A fragment based approach

Bioorg Med Chem Lett. 2018 Jun 1;28(10):1708-1713. doi: 10.1016/j.bmcl.2018.04.050. Epub 2018 Apr 19.

Abstract

The tandem TUDOR domains present in the non-catalytic C-terminal half of the KDM4A, 4B and 4C enzymes play important roles in regulating their chromatin localizations and substrate specificities. They achieve this regulatory role by binding to different tri-methylated lysine residues on histone H3 (H3-K4me3, H3-K23me3) and histone H4 (H4-K20me3) depending upon the specific chromatin environment. In this work, we have used a 2D-NMR based fragment screening approach to identify a novel fragment (1a), which binds to the KDM4A-TUDOR domain and shows modest competition with H3-K4me3 binding in biochemical as well as in vitro cell based assays. A co-crystal structure of KDM4A TUDOR domain in complex with 1a shows that the fragment binds stereo-specifically to the methyl lysine binding pocket forming a network of strong hydrogen bonds and hydrophobic interactions. We anticipate that the fragment 1a can be further developed into a novel allosteric inhibitor of the KDM4 family of enzymes through targeting their C-terminal tandem TUDOR domain.

Keywords: 2D-NMR based fragment screening; Fragment based drug discovery; KDM4A tandem TUDOR domain.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Dose-Response Relationship, Drug
  • Humans
  • Hydrogen Bonding
  • Hydrophobic and Hydrophilic Interactions
  • Jumonji Domain-Containing Histone Demethylases / chemistry*
  • Jumonji Domain-Containing Histone Demethylases / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Structure-Activity Relationship
  • Tudor Domain

Substances

  • Jumonji Domain-Containing Histone Demethylases
  • KDM4A protein, human