Foxo3a Inhibitors of Microbial Origin, JBIR-141 and JBIR-142

Org Lett. 2015 Nov 6;17(21):5476-9. doi: 10.1021/acs.orglett.5b02842. Epub 2015 Oct 23.

Abstract

JBIR-141 (1) and JBIR-142 (2) were discovered as potent Foxo3a inhibitors that consist of three quite unique substructures, a 1-((dimethylamino)ethyl)-5-methyl-4,5-dihydrooxazole-4-carboxylic acid that is originated from Ala-Thr amino acid residues, a 3-acetoxy-4-amino-7-(hydroxy(nitroso)amino)-2,2-dimethylheptanoic acid, and an α-acyl tetramic acid fused with a 2-methylpropan-1-ol moiety. Their structures involving absolute configurations were determined by spectroscopic data, chemical degradation, anisotropy methods, and LC-MS analyses of diastereomeric derivatives. Compounds 1 and 2 exhibited specific inhibition against Foxo3a transcriptional activity with IC50 values of 23.1 and 166.2 nM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Forkhead Box Protein O3
  • Forkhead Transcription Factors / antagonists & inhibitors*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxadiazoles / chemistry
  • Oxadiazoles / isolation & purification*
  • Oxadiazoles / pharmacology*
  • Porifera
  • Streptomyces / chemistry

Substances

  • FOXO3 protein, human
  • Forkhead Box Protein O3
  • Forkhead Transcription Factors
  • JBIR-141
  • JBIR-142
  • Oxadiazoles