KDM4B as a target for prostate cancer: structural analysis and selective inhibition by a novel inhibitor

J Med Chem. 2014 Jul 24;57(14):5975-85. doi: 10.1021/jm500249n. Epub 2014 Jul 9.

Abstract

The KDM4/JMJD2 Jumonji C-containing histone lysine demethylases (KDM4A-KDM4D), which selectively remove the methyl group(s) from tri/dimethylated lysine 9/36 of H3, modulate transcriptional activation and genome stability. The overexpression of KDM4A/KDM4B in prostate cancer and their association with androgen receptor suggest that KDM4A/KDM4B are potential progression factors for prostate cancer. Here, we report the crystal structure of the KDM4B·pyridine 2,4-dicarboxylic acid·H3K9me3 ternary complex, revealing the core active-site region and a selective K9/K36 site. A selective KDM4A/KDM4B inhibitor, 4, that occupies three subsites in the binding pocket is identified by virtual screening. Pharmacological and genetic inhibition of KDM4A/KDM4B significantly blocks the viability of cultured prostate cancer cells, which is accompanied by increased H3K9me3 staining and transcriptional silencing of growth-related genes. Significantly, a substantial portion of differentially expressed genes are AR-responsive, consistent with the roles of KDM4s as critical AR activators. Our results point to KDM4 as a useful therapeutic target and identify a new inhibitor scaffold.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Jumonji Domain-Containing Histone Demethylases / antagonists & inhibitors*
  • Jumonji Domain-Containing Histone Demethylases / chemistry*
  • Jumonji Domain-Containing Histone Demethylases / metabolism
  • Kinetics
  • Male
  • Models, Molecular
  • Molecular Targeted Therapy*
  • Prostatic Neoplasms / drug therapy*
  • Prostatic Neoplasms / enzymology
  • Prostatic Neoplasms / metabolism*
  • Stilbenes / chemistry
  • Stilbenes / pharmacology*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • 1,5-bis(2-(3,4-dichlorophenyl)ethenyl)-2,4-dinitrobenzene
  • Enzyme Inhibitors
  • Stilbenes
  • Jumonji Domain-Containing Histone Demethylases
  • KDM4B protein, human