Target-based approach to inhibitors of histone arginine methyltransferases

J Med Chem. 2007 May 17;50(10):2319-25. doi: 10.1021/jm061250e. Epub 2007 Apr 14.

Abstract

Lysine and arginine methyltransferases participate in the post-translational modification of histones and regulate key cellular functions. So far only one arginine methyltransferase inhibitor discovered by random screening was available. We present the first target-based approach to protein arginine methyltransferase (PRMT) inhibitors. Homology models of human and Aspergillus nidulans PRMT1 were generated from available X-ray structures of rat PRMTs. The NCI diversity set was filtered by a target-based virtual screening to identify PRMT inhibitors. Employing a fungal PRMT for screening and a human enzyme for validation, we have identified seven inhibitors of PRMTs in vitro. Hit validation was achieved for two new inhibitors by antibody mediated detection of histone hypomethylation as well as Western blotting in cancer cells. Functional activity was proven by an observed block of estrogen receptor activation. Thus, valuable chemical tools and potential drug candidates could be identified.

MeSH terms

  • Animals
  • Aspergillus nidulans
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology
  • Binding Sites
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Dapsone / analogs & derivatives
  • Dapsone / chemistry
  • Dapsone / pharmacology
  • Databases, Factual
  • Estrogen Receptor alpha / antagonists & inhibitors
  • Fungal Proteins / antagonists & inhibitors
  • Fungal Proteins / chemistry
  • Histones / metabolism*
  • Humans
  • Methylation
  • Models, Molecular
  • Naphthalenes / chemistry
  • Naphthalenes / pharmacology
  • Protein-Arginine N-Methyltransferases / antagonists & inhibitors*
  • Protein-Arginine N-Methyltransferases / chemistry*
  • Rats
  • Repressor Proteins / antagonists & inhibitors*
  • Repressor Proteins / chemistry*
  • Structure-Activity Relationship
  • Transcription, Genetic / drug effects

Substances

  • Benzimidazoles
  • Estrogen Receptor alpha
  • Fungal Proteins
  • Histones
  • Naphthalenes
  • Repressor Proteins
  • Dapsone
  • PRMT1 protein, human
  • Protein-Arginine N-Methyltransferases