Synthesis of 11.beta.-[18F]Fluoro-5.alpha.-dihydrotestosterone and 11.beta.-[18F]Fluoro-19-nor-5.alpha.-dihydrotestosterone: Preparation via Halofluorination-Reduction, Receptor Binding, and Tissue DistributionClick to copy article linkArticle link copied!
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(9)
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(18)
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(1)
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(1)
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(2)
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(8)
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(2)
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(2)
, 126783. https://doi.org/10.1016/j.bmcl.2019.126783
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(1)
, 53-62. https://doi.org/10.1007/s12149-016-1130-7
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(367)
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(4)
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- Mohammed A. Khayum, Janine Doorduin, Andor W. J. M. Glaudemans, Rudi A. J. O. Dierckx, Erik F. J. de Vries. PET and SPECT Imaging of Steroid Hormone Receptors. 2014, 377-408. https://doi.org/10.1007/978-3-642-42014-6_14
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(7)
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(11)
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(3)
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(4)
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18
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(2)
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(Suppl 1)
, 106S-121S. https://doi.org/10.2967/jnumed.108.057281
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- Ephraim E. Parent, Carmen S. Dence, Terry L. Sharp, Michael J. Welch, John A. Katzenellenbogen. 7α-
18
F-Fluoromethyl-Dihydrotestosterone and 7α-
18
F-Fluoromethyl-Nortestosterone: Ligands to Determine the Role of Sex Hormone–Binding Globulin for Steroidal Radiopharmaceuticals. Journal of Nuclear Medicine 2008, 49
(6)
, 987-994. https://doi.org/10.2967/jnumed.107.048926
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(2)
, 103-121. https://doi.org/10.1016/j.ctrv.2007.10.001
- Sudha Garg, Aniruddha Doke, Kimberly W. Black, Pradeep K. Garg. In vivo biodistribution of an androgen receptor avid PET imaging agent 7-α-fluoro-17 α-methyl-5-α-dihydrotestosterone ([18F]FMDHT) in rats pretreated with cetrorelix, a GnRH antagonist. European Journal of Nuclear Medicine and Molecular Imaging 2008, 35
(2)
, 379-385. https://doi.org/10.1007/s00259-007-0610-3
- Robert Jeraj, M. Elizabeth Meyerand. Molecular and Functional Imaging in Radiation Oncology. 2008, 62-94. https://doi.org/10.1007/978-0-387-36744-6_4
- Aviv Hagooly, Raffaella Rossin, Michael J. Welch. Small Molecule Receptors as Imaging Targets. 2008, 93-129. https://doi.org/10.1007/978-3-540-77496-9_5
- Frédéric Dollé, Dirk Roeda, Bertrand Kuhnast, Marie‐Claire Lasne. Fluorine‐18 Chemistry for Molecular Imaging with Positron Emission Tomography. 2008, 3-65. https://doi.org/10.1016/B978-0-444-53086-8.00001-1
- Ephraim E. Parent, Carl Jenks, Terry Sharp, Michael J. Welch, John A. Katzenellenbogen. Synthesis and biological evaluation of a nonsteroidal bromine-76-labeled androgen receptor ligand 3-[76Br]bromo-hydroxyflutamide. Nuclear Medicine and Biology 2006, 33
(6)
, 705-713. https://doi.org/10.1016/j.nucmedbio.2006.05.009
- Ephraim E. Parent, Carmen S. Dence, Terry L. Sharp, Michael J. Welch, John A. Katzenellenbogen. Synthesis and biological evaluation of a fluorine-18-labeled nonsteroidal androgen receptor antagonist, N-(3-[18F]fluoro-4-nitronaphthyl)-cis-5-norbornene-endo-2,3-dicarboxylic imide. Nuclear Medicine and Biology 2006, 33
(5)
, 615-624. https://doi.org/10.1016/j.nucmedbio.2006.04.003
- Elie Stéphan. SYNTHESIS OF MODIFIED STEROIDS IN THE ANDROSTANE AND ANDROSTENE SERIES. Organic Preparations and Procedures International 2006, 38
(3)
, 217-305. https://doi.org/10.1080/00304940609355990
- Jun Yang, Casey E. Bohl, Vipin A. Nair, Suni M. Mustafa, Seoung Soo Hong, Duane D. Miller, James T. Dalton. Preclinical Pharmacology of a Nonsteroidal Ligand for Androgen Receptor-Mediated Imaging of Prostate Cancer. The Journal of Pharmacology and Experimental Therapeutics 2006, 317
(1)
, 402-408. https://doi.org/10.1124/jpet.105.094334
- Yaniv Barda, Nasi Cohen, Vered Lev, Nurit Ben-Aroya, Yitzhak Koch, Eyal Mishani, Mati Fridkin, Chaim Gilon. Backbone metal cyclization: Novel 99mTc labeled GnRH analog as potential SPECT molecular imaging agent in cancer. Nuclear Medicine and Biology 2004, 31
(7)
, 921-933. https://doi.org/10.1016/j.nucmedbio.2004.05.003
- Bieke Van Den Bossche, Christophe Van de Wiele. Receptor Imaging in Oncology by Means of Nuclear Medicine: Current Status. Journal of Clinical Oncology 2004, 22
(17)
, 3593-3607. https://doi.org/10.1200/JCO.2004.10.216
- Emmanuelle Briard, Victor W. Pike. Substitution‐reduction: an alternative process for the [
18
F]
N
‐(2‐fluoroethylation) of anilines. Journal of Labelled Compounds and Radiopharmaceuticals 2004, 47
(4)
, 217-232. https://doi.org/10.1002/jlcr.816
- Michael J. Morris, Howard I. Scher. Optimizing targeted therapy and developing novel outcome measures for patients with advanced prostate cancer at Memorial Sloan-Kettering Cancer Center. Critical Reviews in Oncology/Hematology 2003, 46 , 21-31. https://doi.org/10.1016/S1040-8428(03)00061-1
- Hélène Pellissier, Maurice Santelli. THE BIRCH REDUCTION OF STEROIDS. A REVIEW. Organic Preparations and Procedures International 2002, 34
(6)
, 609-642. https://doi.org/10.1080/00304940209355785
- Noor‐Ul Hasan Khan, Byung Chul Lee, Sang‐Yoon Lee, Yearn Seong Choe, Chul‐Ho Jun, Dae Yoon Chi. Hydroacylation of 4‐[
18
F]fluorobenzaldehyde: a novel method for the preparation of 4′‐[
18
F]phenylketones. Journal of Labelled Compounds and Radiopharmaceuticals 2002, 45
(12)
, 1045-1053. https://doi.org/10.1002/jlcr.623
- Marie-Claire Lasne, Cécile Perrio, Jacques Rouden, Louisa Barré, Dirck Roeda, Frédéric Dolle, Christian Crouzel. Chemistry of β +-Emitting Compounds Based on Fluorine-18. 2002, 201-258. https://doi.org/10.1007/3-540-46009-8_7
- John A Katzenellenbogen. Steroids labeled with 18F for imaging tumors by positron emission tomography. Journal of Fluorine Chemistry 2001, 109
(1)
, 49-54. https://doi.org/10.1016/S0022-1139(01)00379-7
- James R. Hanson. Steroids: reactions and partial synthesis. Natural Product Reports 1997, 14
(4)
, 373. https://doi.org/10.1039/np9971400373
- Michael J. Welch, Joanna B. Downer, John A. Katzenellenbogen. Steroid Hormone Receptors as Targets for Diagnostic Imaging. 1996, 137-156. https://doi.org/10.1007/978-94-009-1768-2_9
- Yearn Seong Choe, Thomas A. Bonasera, Dae Yoon Chi, Michael J. Welch, John A. Katzenellenbogen. 6α-[18F]Fluoroprogesterone: Synthesis via halofluorination-oxidation, receptor binding and tissue distribution. Nuclear Medicine and Biology 1995, 22
(5)
, 635-642. https://doi.org/10.1016/0969-8051(94)00142-7
- Yearn Seong Choe, John A. Katzenellenbogen. Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging. Steroids 1995, 60
(5)
, 414-422. https://doi.org/10.1016/0039-128X(95)00009-F
- Harold F. Hodson, David J. Madge, David A. Widdowson. Regiospecific synthesis of 4-fluoro-Δ
4
,3-keto steroids using caesium fluoroxysulfate. J. Chem. Soc., Perkin Trans. 1 1995, 35
(23)
, 2965-2970. https://doi.org/10.1039/P19950002965
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