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Title: 21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography

Abstract

We have synthesized 21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone (FENP), a high affinity ligand for the progesterone receptor, labeled with the positron-emitting radionuclide fluorine-18 (t1/2 = 110 min). The synthesis proceeds in two steps from 21-hydroxy-16 alpha-ethyl-19-norprogesterone and involves (/sup 18/F)fluoride ion displacement of the 21-trifluoromethanesulfonate (21-triflate). This material is purified by HPLC and is obtained in 4-30% overall yield (decay corrected) within 40 min after the end of bombardment to produce (/sup 18/F)fluoride ion. The effective specific activity, determined by competitive radioreceptor binding assays, is 700-1400 Ci/mmol. In vivo, (/sup 18/F)FENP demonstrates highly selective, receptor-mediated uptake by the uterus of estrogen-primed rats; the uterus to blood and uterus to muscle ratios were respectively 26 and 16 at 1 h and 71 and 41 at 3 h after injection. The high target tissue selectivity of this uptake suggests that this compound may be useful for the in vivo imaging of progestin target tissues and receptor-rich tumors (such as human breast tumors) by positron emission tomography.

Authors:
; ; ; ;
Publication Date:
Research Org.:
Univ. of Illinois, Urbana (USA)
OSTI Identifier:
7125966
Resource Type:
Journal Article
Journal Name:
J. Med. Chem.; (United States)
Additional Journal Information:
Journal Volume: 31:7
Country of Publication:
United States
Language:
English
Subject:
62 RADIOLOGY AND NUCLEAR MEDICINE; FLUORINE 18; UPTAKE; PROGESTERONE; RECEPTORS; RADIOPHARMACEUTICALS; CHEMICAL PREPARATION; ESTROGENS; LIQUID COLUMN CHROMATOGRAPHY; MAMMARY GLANDS; POSITRON COMPUTED TOMOGRAPHY; RADIORECEPTOR ASSAY; RATS; UTERUS; ANIMALS; BETA DECAY RADIOISOTOPES; BETA-PLUS DECAY RADIOISOTOPES; BODY; CHROMATOGRAPHY; COMPUTERIZED TOMOGRAPHY; DIAGNOSTIC TECHNIQUES; DRUGS; EMISSION COMPUTED TOMOGRAPHY; FEMALE GENITALS; FLUORINE ISOTOPES; GLANDS; HORMONES; HOURS LIVING RADIOISOTOPES; ISOTOPE APPLICATIONS; ISOTOPES; KETONES; LABELLED COMPOUNDS; LIGHT NUCLEI; MAMMALS; MEMBRANE PROTEINS; NUCLEI; ODD-ODD NUCLEI; ORGANIC COMPOUNDS; ORGANS; PREGNANES; PROTEINS; RADIOISOTOPES; RODENTS; SEPARATION PROCESSES; STEROID HORMONES; STEROIDS; SYNTHESIS; TOMOGRAPHY; TRACER TECHNIQUES; VERTEBRATES; 550601* - Medicine- Unsealed Radionuclides in Diagnostics

Citation Formats

Pomper, M G, Katzenellenbogen, J A, Welch, M J, Brodack, J W, and Mathias, C J. 21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography. United States: N. p., 1988. Web. doi:10.1021/jm00402a019.
Pomper, M G, Katzenellenbogen, J A, Welch, M J, Brodack, J W, & Mathias, C J. 21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography. United States. https://doi.org/10.1021/jm00402a019
Pomper, M G, Katzenellenbogen, J A, Welch, M J, Brodack, J W, and Mathias, C J. 1988. "21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography". United States. https://doi.org/10.1021/jm00402a019.
@article{osti_7125966,
title = {21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography},
author = {Pomper, M G and Katzenellenbogen, J A and Welch, M J and Brodack, J W and Mathias, C J},
abstractNote = {We have synthesized 21-(/sup 18/F)fluoro-16 alpha-ethyl-19-norprogesterone (FENP), a high affinity ligand for the progesterone receptor, labeled with the positron-emitting radionuclide fluorine-18 (t1/2 = 110 min). The synthesis proceeds in two steps from 21-hydroxy-16 alpha-ethyl-19-norprogesterone and involves (/sup 18/F)fluoride ion displacement of the 21-trifluoromethanesulfonate (21-triflate). This material is purified by HPLC and is obtained in 4-30% overall yield (decay corrected) within 40 min after the end of bombardment to produce (/sup 18/F)fluoride ion. The effective specific activity, determined by competitive radioreceptor binding assays, is 700-1400 Ci/mmol. In vivo, (/sup 18/F)FENP demonstrates highly selective, receptor-mediated uptake by the uterus of estrogen-primed rats; the uterus to blood and uterus to muscle ratios were respectively 26 and 16 at 1 h and 71 and 41 at 3 h after injection. The high target tissue selectivity of this uptake suggests that this compound may be useful for the in vivo imaging of progestin target tissues and receptor-rich tumors (such as human breast tumors) by positron emission tomography.},
doi = {10.1021/jm00402a019},
url = {https://www.osti.gov/biblio/7125966}, journal = {J. Med. Chem.; (United States)},
number = ,
volume = 31:7,
place = {United States},
year = {Fri Jul 01 00:00:00 EDT 1988},
month = {Fri Jul 01 00:00:00 EDT 1988}
}