Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor.
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.
Ye
Y H
YH
Department of Chemistry, Peking University, Beijing, China.
Huang
Y S
YS
Wang
Z Q
ZQ
Chen
S M
SM
Tian
Y
Y
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D001667:Binding, Competitive; D004958:Estradiol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D005260:Female; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D051381:Rats; D011960:Receptors, Estrogen / Q000378:metabolism*; D014599:Uterus / Q000378:metabolism
D000596:Amino Acids; D007202:Indicators and Reagents; D010455:Peptides; D011960:Receptors, Estrogen; D004958:Estradiol