Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylases for cancer treatment

J Med Chem. 2007 Dec 27;50(26):6685-91. doi: 10.1021/jm070864w. Epub 2007 Nov 27.

Abstract

Mycophenolic acid (MPA), an inhibitor of IMP-dehydrogenase (IMPDH), is used worldwide in transplantation. Recently, numerous studies showed its importance in cancer treatment. Consequently, MPA entered clinical trials in advanced multiple myeloma patients. Suberoylanilide hydroxamic acid (SAHA), a potent differentiation agent acting through inhibition of histone deacetylases (HDACs), was recently approved for treatment of cutaneous T cell lymphoma. We report herein the synthesis of dual inhibitors of IMPDH and HDACs. We found that mycophenolic hydroxamic acid (9, MAHA) inhibits both IMPDH (Ki=30 nM) and HDAC (IC50=5.0 microM). A modification of SAHA with groups known to interact with IMPDH afforded a SAHA analogue 14, which inhibits IMPDH (Ki=1.7 microM) and HDAC (IC50=0.06 microM). Both MAHA (IC50=4.8 microM) and SAHA analogue 14 (IC50=7.7 microM) were more potent than parent compounds as antiproliferation agents. They were also significantly more potent as differentiation inducers.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Differentiation
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Histone Deacetylase Inhibitors*
  • Histone Deacetylases / chemistry
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology
  • IMP Dehydrogenase / antagonists & inhibitors*
  • IMP Dehydrogenase / chemistry
  • K562 Cells
  • Mycophenolic Acid / analogs & derivatives*
  • Mycophenolic Acid / chemical synthesis*
  • Mycophenolic Acid / chemistry
  • Mycophenolic Acid / pharmacology
  • Structure-Activity Relationship
  • Vorinostat

Substances

  • Antineoplastic Agents
  • Histone Deacetylase Inhibitors
  • Hydroxamic Acids
  • Vorinostat
  • IMP Dehydrogenase
  • Histone Deacetylases
  • Mycophenolic Acid