Synthesis and biological properties of a 1-(6-aziridinylhexyl)-2-phenylindole, a potential fluorescence label for estrogen receptors

Arch Pharm (Weinheim). 1990 Aug;323(8):459-63. doi: 10.1002/ardp.19903230804.

Abstract

2-Phenylindole derivative 8, linked to aziridine by a hexamethylene spacer group, was synthesized and tested. It binds to the estrogen receptor with an RBA-value of 4.0 (estradiol = 100). In vitro, it shows a selective cytostatic activity in hormone-dependent MCF-7 breast cancer cells (41% T/C at 10(-6) M). In vivo, it exerts a strong estrogenic effect. The binding to the estrogen receptor is largely reversible.

MeSH terms

  • Animals
  • Aziridines / chemical synthesis*
  • Aziridines / pharmacology
  • Breast Neoplasms / pathology
  • Chemical Phenomena
  • Chemistry
  • Female
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / pharmacology
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Mice
  • Receptors, Estrogen / drug effects*
  • Tumor Cells, Cultured / drug effects
  • Tumor Cells, Cultured / pathology

Substances

  • Aziridines
  • Fluorescent Dyes
  • Indoles
  • Receptors, Estrogen
  • 1-(6-aziridinylhexyl)-2-(4-hydroxyphenyl)indol-5-ol