Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1

Bioorg Med Chem. 2011 Jun 15;19(12):3717-31. doi: 10.1016/j.bmc.2011.02.032. Epub 2011 Feb 27.

Abstract

Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation / drug effects
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Dapsone / chemical synthesis*
  • Dapsone / chemistry
  • Dapsone / pharmacology
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Gene Expression Regulation, Neoplastic / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • Intracellular Signaling Peptides and Proteins
  • Methyltransferases / antagonists & inhibitors*
  • Models, Molecular
  • Molecular Structure
  • Protein-Arginine N-Methyltransferases
  • Receptors, Androgen / genetics
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology

Substances

  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Intracellular Signaling Peptides and Proteins
  • Receptors, Androgen
  • Sulfonamides
  • Dapsone
  • Methyltransferases
  • PRMT2 protein, human
  • Protein-Arginine N-Methyltransferases