Highly cytotoxic and neurotoxic acetogenins of the Annonaceae: new putative biological targets of squamocin detected by activity-based protein profiling

Bioorg Med Chem Lett. 2008 Nov 1;18(21):5741-4. doi: 10.1016/j.bmcl.2008.09.091. Epub 2008 Sep 30.

Abstract

Acetogenins of the Annonaceae are strong inhibitors of mitochondrial complex I but discrepancies in the structure/activity relationships pled the search for other targets within the whole cell proteome. Combining hemisynthetic work, Cu-catalyzed Huisgen cycloaddition and proteomic techniques we have identified new putative protein targets of squamocin ruling out the previously accepted 'complex I dogma'. These results give new insights into the mechanism of action of these potent neurotoxic molecules.

MeSH terms

  • Acetogenins / pharmacology*
  • Annonaceae / chemistry*
  • Electrophoresis, Polyacrylamide Gel
  • Furans / pharmacology*
  • Kinetics
  • Lactones / pharmacology*
  • Microscopy, Confocal
  • Mitochondria / drug effects
  • Neurons / drug effects*
  • Proteins / isolation & purification
  • Proteins / metabolism*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Acetogenins
  • Furans
  • Lactones
  • Proteins
  • squamocin