Bis(indole) alkaloids as sortase A inhibitors from the sponge Spongosorites sp

Bioorg Med Chem Lett. 2005 Nov 15;15(22):4927-31. doi: 10.1016/j.bmcl.2005.08.021.

Abstract

A new bis(indole) alkaloid (9) of the hamacanthin class along with the previously reported compounds of the related structural classes, topsentin class (1-4) and hamacanthin class (5-8), was isolated from the marine sponge Spongosorites sp. and their inhibitory activities toward sortase A (SrtA) that play key roles in cell-wall protein anchoring and virulence in Staphylococcus aureus were evaluated. Our studies have identified a series of SrtA inhibitors, providing the basis for further development of potent inhibitors. The preliminary structure-activity relationship, to elucidate the essential structural requirements, has been described. The fibronectin-binding activity data highlight the potential of these compounds for the treatment of S. aureus infections via inhibition of SrtA activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Aminoacyltransferases / antagonists & inhibitors*
  • Aminoacyltransferases / metabolism
  • Animals
  • Bacterial Adhesion / drug effects
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / metabolism
  • Cysteine Endopeptidases
  • Fibronectins / metabolism
  • Indoles / chemistry*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera / chemistry*
  • Protein Binding
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / enzymology

Substances

  • Alkaloids
  • Bacterial Proteins
  • Fibronectins
  • Indoles
  • indole
  • Aminoacyltransferases
  • sortase A
  • Cysteine Endopeptidases