Pipecolic acid derivatives as small-molecule inhibitors of the Legionella MIP protein

J Med Chem. 2011 Jan 13;54(1):277-83. doi: 10.1021/jm101156y. Epub 2010 Dec 13.

Abstract

The macrophage infectivity potentiator (MIP) protein is a major virulence factor of Legionella pneumophila, the causative agent of Legionnaires' disease. MIP belongs to the FK506-binding proteins (FKBP) and is necessary for optimal intracellular survival and lung tissue dissemination of L. pneumophila. We aimed to identify new small-molecule inhibitors of MIP by starting from known FKBP12 ligands. Computational analysis, synthesis, and biological testing of pipecolic acid derivatives revealed a promising scaffold for new MIP inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / chemistry
  • Binding Sites
  • Cell Line
  • Colony Count, Microbial
  • Guinea Pigs
  • Legionella pneumophila / drug effects*
  • Legionella pneumophila / enzymology
  • Legionnaires' Disease / drug therapy
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Peptidylprolyl Isomerase / antagonists & inhibitors*
  • Peptidylprolyl Isomerase / chemistry
  • Pipecolic Acids / chemical synthesis*
  • Pipecolic Acids / chemistry
  • Pipecolic Acids / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tacrolimus Binding Protein 1A / chemistry

Substances

  • Bacterial Proteins
  • Pipecolic Acids
  • Tacrolimus Binding Protein 1A
  • Mip protein, Legionella pneumophila
  • Peptidylprolyl Isomerase