PMID: 9434339Jan 22, 1998Paper

The metabolism of 16-fluoroestradiols in vivo: chemical strategies for restricting the oxidative biotransformations of an estrogen-receptor imaging agent

Steroids
A C StalfordB K Park

Abstract

16 alpha-Fluoro-17 beta-, 16 alpha-fluoro-17 alpha-, and 16 beta-fluoro-17 beta-[6,7-3H]estradiol were prepared from [6,7-3H]estrone via fluorination of 3,17-bis(tert-butyldimethylsilyloxy)-[6,7-3H]estratetraene with N-fluoropyridinium triflate and reduction of 16 alpha/beta-fluoro[6,7-3H]estrone with NaBH4. The three isomers were separated by silica-phase high-performance liquid chromatography. They were administered intravenously (4 mumol/kg to anaesthetized male rats. Their biliary metabolites (90-97% of dose over 6 h) were characterized by high performance liquid chromatography-mass spectrometry and compared with those of [6,7-3H]17 beta-estradiol. The four estrogens and their hydroxylated and methoxylated metabolites were excreted as glucuronides. C-16 fluorination blocked C-16 hydroxylated and also the dehydrogenation of the C-17 hydroxyl group. The 16 alpha-17 beta isomer was extensively glucuronylated at C(O)3 but also underwent aromatic hydroxylation and methoxylation before conjugation. Its C-17 epimer was subject to much greater aromatic hydroxylation but the catecholestrogen was O-methylated to a greater relative extent. The 16 beta-17 beta derivative underwent alicyclic as well as substantial aromatic hydroxylation...Continue Reading

References

Apr 1, 1992·International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology·H F VanBrocklinJ A Katzenellenbogen
Aug 14, 1990·Journal of Steroid Biochemistry·T OhkuboT Nambara
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Jun 1, 1993·Steroids·C H Cummins
Dec 1, 1993·The Journal of Steroid Biochemistry and Molecular Biology·S M AbelB K Park

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Citations

Mar 27, 2001·Annual Review of Pharmacology and Toxicology·B K ParkP M O'Neill
Apr 27, 2013·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Michel PaquetteRoger Lecomte
Nov 27, 2007·Journal of Enzyme Inhibition and Medicinal Chemistry·Poonam Shah, Andrew D Westwell
Feb 6, 2018·Journal of Medicinal Chemistry·Nicholas A Meanwell

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