(2R*, 3S*)-1- [18fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([18F]fluoronorhexestrol), A positron-emitting estrogen that shows highly-selective, receptor-mediated uptake by target tissues in vivo

Scott W. Landvatter; Dale O. Kiesewetter; Michael R. Kilbourn; John A. Katzenellenbogen; Michael J. Welch

doi:10.1016/0024-3205(83)90678-1

(2R^, 3S^)-1- [¹⁸fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([¹⁸F]fluoronorhexestrol), A positron-emitting estrogen that shows highly-selective, receptor-mediated uptake by target tissues in vivo

Scott W. Landvatter
, Dale O. Kiesewetter
, Michael R. Kilbourn
, John A. Katzenellenbogen
, Michael J. Welch

Chemistry

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

Abstract

The positron-emitting, non-steroidal estrogen (2R^*, 3S^*)-1-[¹⁸F]fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([¹⁸F]-fluoronor-hexestrol), has been prepared by fluoride ion displacement on a labile trifluoromethanesulfonate (triflate) derivative of a suitably protected precursor, followed by removal of the aryl triflate groups with lithium aluminum hydride and purification by HPLC. In immature female rats, this compound is taken up selectively by the uterus and is retained for prolonged periods, due to its binding to the estrogen receptor. This compound and related ¹⁸F-labeled estrogens thus appear to be promising agents for imaging estrogen receptor-positive breast tumors in humans.

Original language	English (US)
Pages (from-to)	1933-1938
Number of pages	6
Journal	Life Sciences
Volume	33
Issue number	19
DOIs	https://doi.org/10.1016/0024-3205(83)90678-1
State	Published - Nov 7 1983

ASJC Scopus subject areas

General Biochemistry, Genetics and Molecular Biology
Pharmacology, Toxicology and Pharmaceutics(all)

Online availability

10.1016/0024-3205(83)90678-1

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Cite this

Landvatter, S. W., Kiesewetter, D. O., Kilbourn, M. R., Katzenellenbogen, J. A., & Welch, M. J. (1983). (2R^*, 3S^*)-1- [¹⁸fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([¹⁸F]fluoronorhexestrol), A positron-emitting estrogen that shows highly-selective, receptor-mediated uptake by target tissues in vivo. Life Sciences, 33(19), 1933-1938. https://doi.org/10.1016/0024-3205(83)90678-1

(2R^*, 3S^*)-1- [¹⁸fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([¹⁸F]fluoronorhexestrol), A positron-emitting estrogen that shows highly-selective, receptor-mediated uptake by target tissues in vivo. / Landvatter, Scott W.; Kiesewetter, Dale O.; Kilbourn, Michael R. et al.
In: Life Sciences, Vol. 33, No. 19, 07.11.1983, p. 1933-1938.

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

Landvatter, SW, Kiesewetter, DO, Kilbourn, MR, Katzenellenbogen, JA & Welch, MJ 1983, '(2R^*, 3S^*)-1- [¹⁸fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([¹⁸F]fluoronorhexestrol), A positron-emitting estrogen that shows highly-selective, receptor-mediated uptake by target tissues in vivo', Life Sciences, vol. 33, no. 19, pp. 1933-1938. https://doi.org/10.1016/0024-3205(83)90678-1

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title = "(2R*, 3S*)-1- [18fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([18F]fluoronorhexestrol), A positron-emitting estrogen that shows highly-selective, receptor-mediated uptake by target tissues in vivo",

abstract = "The positron-emitting, non-steroidal estrogen (2R*, 3S*)-1-[18F]fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([18F]-fluoronor-hexestrol), has been prepared by fluoride ion displacement on a labile trifluoromethanesulfonate (triflate) derivative of a suitably protected precursor, followed by removal of the aryl triflate groups with lithium aluminum hydride and purification by HPLC. In immature female rats, this compound is taken up selectively by the uterus and is retained for prolonged periods, due to its binding to the estrogen receptor. This compound and related 18F-labeled estrogens thus appear to be promising agents for imaging estrogen receptor-positive breast tumors in humans.",

author = "Landvatter, \{Scott W.\} and Kiesewetter, \{Dale O.\} and Kilbourn, \{Michael R.\} and Katzenellenbogen, \{John A.\} and Welch, \{Michael J.\}",

note = "This work was supported by grants from the National Institutes of Health (PHS 5ROI CA 25836 and PHS 3POI HL 13851) and the U.S. Department of Energy (DE ACO2-81EVI0650). The authors thank Carla J. Mathias and Kathryn E. Carlson for their assistance with the animal experiments.",

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AU - Welch, Michael J.

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N2 - The positron-emitting, non-steroidal estrogen (2R*, 3S*)-1-[18F]fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([18F]-fluoronor-hexestrol), has been prepared by fluoride ion displacement on a labile trifluoromethanesulfonate (triflate) derivative of a suitably protected precursor, followed by removal of the aryl triflate groups with lithium aluminum hydride and purification by HPLC. In immature female rats, this compound is taken up selectively by the uterus and is retained for prolonged periods, due to its binding to the estrogen receptor. This compound and related 18F-labeled estrogens thus appear to be promising agents for imaging estrogen receptor-positive breast tumors in humans.

AB - The positron-emitting, non-steroidal estrogen (2R*, 3S*)-1-[18F]fluoro-2, 3-bis (4-hydroxyphenyl) pentane ([18F]-fluoronor-hexestrol), has been prepared by fluoride ion displacement on a labile trifluoromethanesulfonate (triflate) derivative of a suitably protected precursor, followed by removal of the aryl triflate groups with lithium aluminum hydride and purification by HPLC. In immature female rats, this compound is taken up selectively by the uterus and is retained for prolonged periods, due to its binding to the estrogen receptor. This compound and related 18F-labeled estrogens thus appear to be promising agents for imaging estrogen receptor-positive breast tumors in humans.

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