Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor

Steroids. 1993 Jan;58(1):35-9. doi: 10.1016/0039-128x(93)90015-f.

Abstract

A series of amino acid and peptide derivatives of estradiol have been synthesized by coupling 17 beta-aminoestra-1,3,5(10)-trien-3-ol, 17-hydrazonoestra-1,3,5(10)-trien-3-ol with amino acids or peptides, using tetrahydrothiazole-2-thione, N-hydroxy-1,4-epoxycyclohex-5-ene-2,3-dicarbonylimide, benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate, and p-nitrophenol as reagents. N-protected peptidyl steroids were deprotected by traditional methods. The relative binding affinities of the deprotected derivatives to the estrogen receptor were determined by competitive radioligand binding assay.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Amino Acids / metabolism
  • Animals
  • Binding, Competitive
  • Estradiol / analogs & derivatives*
  • Estradiol / chemistry
  • Estradiol / metabolism
  • Female
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptides / metabolism
  • Rats
  • Receptors, Estrogen / metabolism*
  • Uterus / metabolism

Substances

  • Amino Acids
  • Indicators and Reagents
  • Peptides
  • Receptors, Estrogen
  • Estradiol