Design, synthesis and evaluation of 6-aryl-indenoisoquinolone derivatives dual targeting ERα and VEGFR-2 as anti-breast cancer agents

Eur J Med Chem. 2016 Aug 8:118:328-39. doi: 10.1016/j.ejmech.2016.04.029. Epub 2016 Apr 13.

Abstract

The estrogen receptors have played important roles in breast cancer development and progression. Selective estrogen receptor modulators, such as Tamoxifen, have showed great benefits in the treatment and prevention of breast cancer. But the disadvantages of induction of endometrial cancer and drug resistance have limited their use. Multiple ligand which act at multiple biomolecular targets may exert favorable advantages of improved efficacy with lower incidence of side effects. In this work, we described the synthesis and evaluation of a series of 6-aryl-indenoisoquinolone derivatives as dual ERα and VEGFR-2 inhibitors. These compounds presented good ERα binding affinity and ERα antagonistic activity, as well as potent VEGFR-2 inhibitory potency. They also possessed excellent anti-proliferative activities against MCF-7, MDA-MB-231, Ishikawa and HUVEC cell lines. Further investigation of selective compound 21c showed that it was able to inhibit the activation of VEGFR-2 and the signaling transduction of Raf-1/MAPK/ERK pathway in MCF-7 cells.

Keywords: Breast cancer; Dual inhibitor; Estrogen receptor; VEGFR-2.

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis
  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / metabolism
  • Angiogenesis Inhibitors / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Chemistry Techniques, Synthetic
  • Drug Design*
  • Estrogen Receptor alpha / chemistry
  • Estrogen Receptor alpha / metabolism*
  • Gene Expression Regulation, Neoplastic / drug effects
  • Humans
  • MCF-7 Cells
  • Models, Molecular
  • Molecular Targeted Therapy*
  • Protein Conformation
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry
  • Quinolones / metabolism
  • Quinolones / pharmacology*
  • RNA, Messenger / genetics
  • RNA, Messenger / metabolism
  • Receptors, Progesterone / genetics
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*
  • Vascular Endothelial Growth Factor Receptor-2 / metabolism

Substances

  • Angiogenesis Inhibitors
  • Antineoplastic Agents
  • Estrogen Receptor alpha
  • Quinolones
  • RNA, Messenger
  • Receptors, Progesterone
  • Vascular Endothelial Growth Factor Receptor-2