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A facile and improved synthesis of 17α‐{2‐(E)‐[ 1 2 5 I]‐iodovinyl}‐19‐nortestosterone, a no‐carrier‐added ligand for progesterone receptor analyses
Author(s) -
Damodaran Kalyani M.,
Epperly Michael W.,
Pillai K. M. R.,
Bloomer William D.
Publication year - 1994
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580340104
Subject(s) - chemistry , progesterone receptor , ligand (biochemistry) , receptor , combinatorial chemistry , stereochemistry , medicine , biochemistry , estrogen receptor , cancer , breast cancer
Strategies for human breast cancer therapy using 125 I‐labeled steroid hormones are clinically attractive in light of the estrogen dependence of and progestogen receptor involvement in many cancers and the favorable microdosimetry resulting from 125 I decay. We have synthesized the no‐carrier‐added progesterone receptor ligand 17α‐{2‐(E)‐[ 125 I]‐iodovinyl}‐19‐nortestosterone (E‐ 125 IVNNT) by a simple and high yielding method, and determined its uptake and specific progesterone receptor binding in vitro using T47D human breast carcinoma cells. The ligand was prepared by [ 125 I]‐iododestannylation of 17α‐[2‐(E)‐tri‐n‐butylstannylvinyl]‐19‐nortestosterone (E‐TBSVNNT) by using the rare iodinating agent [ 125 I]‐sodium iodide/ferric sulfate in mixed dichloromethane‐water solvent. Cell binding assays demonstrated that E‐ 125 IVNNT binding to T47D breast carcinoma was specific and saturable with an affinity for the progesterone receptor 10‐fold greater than that of 3 H‐R5020.