Fumarranol, a rearranged fumagillin analogue that inhibits angiogenesis in vivo

J Med Chem. 2006 Sep 21;49(19):5645-8. doi: 10.1021/jm060559v.

Abstract

The fumagillin family of natural products inhibits angiogenesis through the irreversible inhibition of the type 2 methionine aminopeptidase (MetAP2). Herein is reported a novel fumagillin analogue named fumarranol. It is shown that, like fumagillin, fumarranol selectively inhibits MetAP2 and endothelial cell proliferation. It is also active in a mouse model of angiogenesis in vivo. Unlike TNP-470, fumarranol does not covalently bind to MetAP2. Fumarranol may serve as a lead for a new class of angiogenesis inhibitors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminopeptidases / antagonists & inhibitors
  • Angiogenesis Inhibitors / chemical synthesis*
  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / pharmacology
  • Animals
  • Cattle
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Collagen
  • Crystallography, X-Ray
  • Cyclohexanes
  • Drug Combinations
  • Endothelial Cells / cytology
  • Endothelial Cells / drug effects
  • Endothelium, Vascular / cytology
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / pharmacology
  • Glycoproteins / antagonists & inhibitors
  • Laminin
  • Methionyl Aminopeptidases
  • Mice
  • Molecular Structure
  • Proteoglycans
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology
  • Structure-Activity Relationship

Substances

  • Angiogenesis Inhibitors
  • Cyclohexanes
  • Drug Combinations
  • Fatty Acids, Unsaturated
  • Glycoproteins
  • Laminin
  • Proteoglycans
  • Sesquiterpenes
  • fumarranol
  • matrigel
  • fumagillin
  • Collagen
  • Aminopeptidases
  • METAP2 protein, human
  • Methionyl Aminopeptidases