Dual inhibitors of the pro-survival proteins Bcl-2 and Mcl-1 derived from natural compound meiogynin A

Eur J Med Chem. 2018 Mar 25:148:26-38. doi: 10.1016/j.ejmech.2018.01.100. Epub 2018 Feb 5.

Abstract

Thirty analogues of natural meiogynin A, a pan-Bcl-2 inhibitor, were prepared in order to elaborate cytotoxic compounds on specific cancer cells overexpressing one or more proteins of the Bcl-2 family. The interaction of all the new analogues with Bcl-xL, Mcl-1 and Bcl-2 proteins was first evaluated by fluorescence polarization assay (FPA) and showed that modulation of the lateral chain has a dramatic impact as subtle changes significantly modify the activity on the target proteins. The acetoxymethyl prodrugs of the two most active compounds were then elaborated to determine their cytotoxicity on B cell lines. A strong cytotoxic effect on BL2, RS4;11 and H929 cells was observed with a triazole prodrug that induces apoptosis.

Keywords: Apoptosis; Bcl-2 proteins; Cancer; Natural compound; Protein-protein interactions.

MeSH terms

  • Apoptosis / drug effects
  • Apoptosis Regulatory Proteins / antagonists & inhibitors
  • B-Lymphocytes / drug effects
  • Cell Line, Tumor
  • Fluorescence Polarization Immunoassay
  • Humans
  • Myeloid Cell Leukemia Sequence 1 Protein / antagonists & inhibitors*
  • Prodrugs / chemistry
  • Prodrugs / pharmacology
  • Proto-Oncogene Proteins c-bcl-2 / antagonists & inhibitors*
  • Sesquiterpenes / chemistry*
  • Structure-Activity Relationship
  • bcl-X Protein

Substances

  • Apoptosis Regulatory Proteins
  • BCL2 protein, human
  • MCL1 protein, human
  • Myeloid Cell Leukemia Sequence 1 Protein
  • Prodrugs
  • Proto-Oncogene Proteins c-bcl-2
  • Sesquiterpenes
  • bcl-X Protein
  • meiogynin A