Radiohalodestannylation: synthesis of 125I-labeled 17 alpha-E-iodovinylestradiol.
17 alpha-E-Iodovinylestradiol and its iodine-125-labeled analog were prepared by halodestannylation. The synthesis of the unlabeled compound was achieved from estrone in two steps with an overall yield of 30%. The tributylstannylvinylestradiol intermediate reacted with sodium [125I]iodide (specific activity = 2200 Ci/mmol) in the presence of hydrogen peroxide and acetic acid to give the 17 alpha-E-[125I]iodovinylestradiol in 40-60% yield after isolation by reversed phase column chromatography. The radiochemical purity was greater than 98% and no other u.v. active components could be detected by HPLC. The ease of preparation and isolation of this radioligand suggests that radiohalodestannylation may be the method of choice for this and structurally similar compounds.
D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007457:Iodine Radioisotopes; D007553:Isotope Labeling; D011960:Receptors, Estrogen / Q000032:analysis
D007457:Iodine Radioisotopes; D011960:Receptors, Estrogen; D004958:Estradiol; C034555:17 alpha-iodovinylestradiol