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

Article abstract of DOI:10.1016/0039-128X(93)90015-F

A series of amino acid and peptide derivatives of estradiol have been synthesized by coupling 17β-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.Keywords: 17β-aminoestradiol derivatives; 17-hydrazonoestrone derivatives; amino acids; peptides; binding affinity; estrogen receptor; steroids