Pyridinylquinazolines selectively inhibit human methionine aminopeptidase-1 in cells

J Med Chem. 2013 May 23;56(10):3996-4016. doi: 10.1021/jm400227z. Epub 2013 May 1.

Abstract

Methionine aminopeptidases (MetAPs), which remove the initiator methionine from nascent peptides, are essential in all organisms. While MetAP2 has been demonstrated to be a therapeutic target for inhibiting angiogenesis in mammals, MetAP1 seems to be vital for cell proliferation. Our earlier efforts identified two structural classes of human MetAP1 (HsMetAP1)-selective inhibitors (1-4), but all of them failed to inhibit cellular HsMetAP1. Using Mn(II) or Zn(II) to activate HsMetAP1, we found that 1-4 could only effectively inhibit purified HsMetAP1 in the presence of physiologically unachievable concentrations of Co(II). In an effort to seek Co(II)-independent inhibitors, a novel structural class containing a 2-(pyridin-2-yl)quinazoline core has been discovered. Many compounds in this class potently and selectively inhibited HsMetAP1 without Co(II). Subsequently, we demonstrated that 11j, an auxiliary metal-dependent inhibitor, effectively inhibited HsMetAP1 in primary cells. This is the first report that an HsMetAP1-selective inhibitor is effective against its target in cells.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aminopeptidases / antagonists & inhibitors*
  • Aminopeptidases / biosynthesis
  • Animals
  • Cell Proliferation / drug effects
  • Chelating Agents / pharmacology
  • Chromatography, Thin Layer
  • Cobalt / pharmacology
  • Crystallography, X-Ray
  • Down-Regulation / drug effects
  • Enzyme Activation / drug effects
  • HeLa Cells
  • Human Umbilical Vein Endothelial Cells / drug effects
  • Humans
  • Indicators and Reagents
  • Manganese / pharmacology
  • Metals / chemistry
  • Methionine / metabolism
  • Mice
  • Models, Molecular
  • Protease Inhibitors / pharmacology*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • RNA, Small Interfering / chemistry
  • RNA, Small Interfering / pharmacology
  • Thymidine / metabolism
  • Transfection
  • Zinc / pharmacology

Substances

  • Chelating Agents
  • Indicators and Reagents
  • Metals
  • Protease Inhibitors
  • Pyridines
  • Quinazolines
  • RNA, Small Interfering
  • Cobalt
  • Manganese
  • Methionine
  • Aminopeptidases
  • METAP1D protein, human
  • Zinc
  • Thymidine

Associated data

  • PDB/4IU6