title: Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol and.
abstract: The synthesis of two novel radiolabelled estrogen derivatives, [125I](E)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol (E[125I]IVDE) and [125I](Z)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol (Z[125I]IVDE), was carried out aiming to study the influence of the introduction of a C6-C7 double bond on the biological properties of the estradiol molecule. 3-Methoxyestra-1,3,5(10),6-tetraen-17-one was synthesised starting from a suitably protected estrone and subsequently converted into the 17alpha-ethynyl derivative. The radioiodinated derivatives were stereoselectively formed by radioiododestannylation of the corresponding tributylstannyl precursors. The biodistribution of the novel [125I]iodovinylestradiol derivatives was evaluated in immature female mice. Biological data indicated that the Z-isomer, owing to its higher in vivo uptake by the target tissue, has the preferable configuration for further development of similar compounds for estrogen receptor detection.
authors.affiliation: Instituto Tecnológico e Nuclear, Estrada Nacional No. 10, Sacavém, Portugal. thies@cm.kyushu-u.ac.jp
authors.forename: M C
authors.initials: MC
authors.lastname: Melo e Silva
authors.forename: L
authors.initials: L
authors.lastname: Patrćio
authors.forename: L
authors.initials: L
authors.lastname: Gano
authors.forename: M L
authors.initials: ML
authors.lastname: Sá e Melo
authors.forename: E
authors.initials: E
authors.lastname: Inohae
authors.forename: S
authors.initials: S
authors.lastname: Mataka
authors.forename: T
authors.initials: T
authors.lastname: Thiemann
mesh_terms: D000818:Animals; D001943:Breast Neoplasms / Q000000981:diagnostic imaging / Q000378:metabolism; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000493:pharmacokinetics*; D045166:Estradiol Congeners / Q000138:chemical synthesis* / Q000493:pharmacokinetics*; D005260:Female; D006801:Humans; D007457:Iodine Radioisotopes; D051379:Mice; D011877:Radionuclide Imaging; D011960:Receptors, Estrogen / Q000378:metabolism; D013237:Stereoisomerism; D014018:Tissue Distribution; D014599:Uterus / Q000378:metabolism
chemical_list: D045166:Estradiol Congeners; D007457:Iodine Radioisotopes; D011960:Receptors, Estrogen; D004958:Estradiol; C042987:17-iodovinylestradiol-3-methyl ether