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20-[¹⁸F]Fluoromibolerone, a Positron-Emitting Radiotracer for Androgen Receptors: Synthesis and Tissue Distribution Studies

Department of Chemistry, University of Illinois, Urbana, Illinois
Division of Radiation Sciences Research, Mallinckrodt Institute of Radiology, Washington University Medical School, St. Louis, Missouri

Correspondence: For reprints contact: John A. Katzenellenbogen, PhD, Department of Chemistry, University of Illinois, Box 37, 1209 W. California St., Urbana, IL 61801.

ABSTRACT

To develop an androgen receptor-based, positron-emitting imaging agent for prostate tumors, we have prepared 20-fluoromibolerone (F-Mib) and evaluated its tissue distribution. This compound was synthesized in eight steps from 7-methyl-19-nortestosterone, with fluorine introduced in the penultimate step by fluoride ion displacement on a spirocyclic sulfate. Fluoromibolerone was obtained in 9%–19% radiochemical yield (decay corrected), at 1.5 hr after bombardment, with an effective specific activity of 217–283 Ci/mmol. The relative binding affinity of F-Mib is 53 (versus R1881 = 100 or mibolerone = 118). In tissue distribution studies in diethylstilbestrol-treated male rats, ¹⁸F-Mib demonstrates high target/tissue uptake efficiency and selectivity: the prostate uptake at 0.5 hr and 4 hr is 1.0%–1.3% injected dose/gram tissue (ID/g) and 0.5%–0.6% ID/g, respectively; the prostate-to-blood and the prostate-to-muscle (non-target) ratios are both ca. 4 at 0.5 hr, and increase to ca. 12 by 4 hr after injection. The observed distribution of ¹⁸F-Mib suggests that it may be useful for in vivo imaging of prostatic tumors in man by positron emission tomography.

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				E. E. Parent, C. S. Dence, T. L. Sharp, M. J. Welch, and J. A. Katzenellenbogen 7{alpha}-18F-Fluoromethyl-Dihydrotestosterone and 7{alpha}-18F-Fluoromethyl-Nortestosterone: Ligands to Determine the Role of Sex Hormone-Binding Globulin for Steroidal Radiopharmaceuticals J. Nucl. Med., June 1, 2008; 49(6): 987 - 994. [Abstract] [Full Text] [PDF]