Structural basis for binding and selectivity of antimalarial and anticancer ethylenediamine inhibitors to protein farnesyltransferase

Chem Biol. 2009 Feb 27;16(2):181-92. doi: 10.1016/j.chembiol.2009.01.014.

Abstract

Protein farnesyltransferase (FTase) catalyzes an essential posttranslational lipid modification of more than 60 proteins involved in intracellular signal transduction networks. FTase inhibitors have emerged as a significant target for development of anticancer therapeutics and, more recently, for the treatment of parasitic diseases caused by protozoan pathogens, including malaria (Plasmodium falciparum). We present the X-ray crystallographic structures of complexes of mammalian FTase with five inhibitors based on an ethylenediamine scaffold, two of which exhibit over 1000-fold selective inhibition of P. falciparum FTase. These structures reveal the dominant determinants in both the inhibitor and enzyme that control binding and selectivity. Comparison to a homology model constructed for the P. falciparum FTase suggests opportunities for further improving selectivity of a new generation of antimalarial inhibitors.

Publication types

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

MeSH terms

  • Animals
  • Antimalarials / chemistry*
  • Antimalarials / metabolism
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / metabolism
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Ethylenediamines / chemistry
  • Farnesyltranstransferase / antagonists & inhibitors*
  • Farnesyltranstransferase / chemistry*
  • Farnesyltranstransferase / metabolism
  • Humans
  • Plasmodium falciparum / enzymology
  • Protein Binding
  • Protein Conformation
  • Protozoan Proteins / antagonists & inhibitors
  • Protozoan Proteins / chemistry
  • Protozoan Proteins / metabolism
  • Rats
  • Structural Homology, Protein
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Antimalarials
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Ethylenediamines
  • Protozoan Proteins
  • ethylenediamine
  • Farnesyltranstransferase