Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [125I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol

M. Cristina Melo e Silva; Luciana Patrício; Lurdes Gano; M. Luísa Sá e Melo; Eiko Inohae; Shuntaro Mataka; Thies Thiemann

doi:10.1016/S0969-8043(99)00258-4

Synthesis and biological evaluation of two new radiolabelled estrogens: [¹²⁵I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [¹²⁵I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol

M. Cristina Melo e Silva
, Luciana Patrício
, Lurdes Gano
, M. Luísa Sá e Melo
, Eiko Inohae
, Shuntaro Mataka
, Thies Thiemann

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

The synthesis of two novel radiolabelled estrogen derivatives, [¹²⁵I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol (E[¹²⁵I]IVDE) and [¹²⁵I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-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 17α-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. Copyright (C) 2001 Elsevier Science Ltd.

Original language	English
Pages (from-to)	227-239
Number of pages	13
Journal	Applied Radiation and Isotopes
Volume	54
Issue number	2
DOIs	https://doi.org/10.1016/S0969-8043(99)00258-4
Publication status	Published - Feb 2001
Externally published	Yes

ASJC Scopus subject areas

Radiation

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Melo e Silva, M. C., Patrício, L., Gano, L., Sá e Melo, M. L., Inohae, E., Mataka, S., & Thiemann, T. (2001). Synthesis and biological evaluation of two new radiolabelled estrogens: [¹²⁵I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [¹²⁵I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol. Applied Radiation and Isotopes, 54(2), 227-239. https://doi.org/10.1016/S0969-8043(99)00258-4

Synthesis and biological evaluation of two new radiolabelled estrogens: [¹²⁵I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [¹²⁵I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol. / Melo e Silva, M. Cristina; Patrício, Luciana; Gano, Lurdes et al.
In: Applied Radiation and Isotopes, Vol. 54, No. 2, 02.2001, p. 227-239.

Research output: Contribution to journal › Article › peer-review

Melo e Silva, MC, Patrício, L, Gano, L, Sá e Melo, ML, Inohae, E, Mataka, S & Thiemann, T 2001, 'Synthesis and biological evaluation of two new radiolabelled estrogens: [¹²⁵I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [¹²⁵I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol', Applied Radiation and Isotopes, vol. 54, no. 2, pp. 227-239. https://doi.org/10.1016/S0969-8043(99)00258-4

Melo e Silva MC, Patrício L, Gano L, Sá e Melo ML, Inohae E, Mataka S et al. Synthesis and biological evaluation of two new radiolabelled estrogens: [¹²⁵I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [¹²⁵I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol. Applied Radiation and Isotopes. 2001 Feb;54(2):227-239. doi: 10.1016/S0969-8043(99)00258-4

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title = "Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol and [125I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol",

abstract = "The synthesis of two novel radiolabelled estrogen derivatives, [125I](E)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-ol (E[125I]IVDE) and [125I](Z)-3-methoxy-17α-iodovinylestra-1,3,5(10),6-tetraen-17β-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 17α-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. Copyright (C) 2001 Elsevier Science Ltd.",

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