New scaffolds for the design of selective estrogen receptor modulators

Org Biomol Chem. 2008 Oct 7;6(19):3486-96. doi: 10.1039/b806918b. Epub 2008 Aug 4.

Abstract

In the present work we report the synthesis of four new ER ligands which can be used as scaffolds for the introduction of the basic side chains necessary for antiestrogenic activity. Affinities and agonist/antagonist characterization of the ligands for both ERalpha and ERbeta have been determined in a competitive radioligand assay, and in an in vitro coactivator recruitment functional assay, respectively. Molecular modelling techniques have been used in order to rationalize the experimental results. Compound is reported as a novel ERbeta-agonist/ERalpha-antagonist. Two compounds show an interesting antitumour profile towards two pancreatic cancer cell lines and have been selected for in vivo assays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design*
  • Estradiol / metabolism
  • Estrogen Receptor alpha / agonists
  • Estrogen Receptor alpha / antagonists & inhibitors
  • Estrogen Receptor alpha / chemistry
  • Estrogen Receptor alpha / metabolism
  • Estrogen Receptor beta / agonists
  • Estrogen Receptor beta / antagonists & inhibitors
  • Estrogen Receptor beta / chemistry
  • Estrogen Receptor beta / metabolism
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Selective Estrogen Receptor Modulators / chemical synthesis*
  • Selective Estrogen Receptor Modulators / chemistry
  • Selective Estrogen Receptor Modulators / metabolism
  • Selective Estrogen Receptor Modulators / pharmacology
  • Substrate Specificity

Substances

  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Selective Estrogen Receptor Modulators
  • Estradiol