Synthesis of [11C]bexarotene by cu-mediated [ 11C]carbon dioxide fixation and preliminary PET imaging

ACS Medicinal Chemistry Letters

Volumn 5, Issue 6, 2014, Pages 668-672

  Rotstein, Benjamin H ^a,b   Hooker, Jacob M ^a,b   Woo, Jiyeon ^a   Collier, Thomas Lee ^a,b,c   Brady, Thomas J ^a,b   Liang, Steven H ^a,b   Vasdev, Neil ^a,b  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

^c Advion BioSciences Inc   (United States)

Author keywords

Alzheimer's disease; Bexarotene; carbon dioxide fixation; carbon 11; positron emission tomography; retinoid X receptor; targretin

Indexed keywords

BEXAROTENE C 11; CARBON DIOXIDE C 11; COPPER DERIVATIVE; DRUG ADDITIVE; RADIOPHARMACEUTICAL AGENT; RETINOID X RECEPTOR; SOLVENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; ATMOSPHERIC PRESSURE; BRAIN FUNCTION; BRAIN REGION; CARBON DIOXIDE FIXATION; CONCENTRATION (PARAMETERS); CROSS COUPLING REACTION; DOSE TIME EFFECT RELATION; DRUG CLEARANCE; DRUG ISOLATION; DRUG PURITY; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; ISOTOPE LABELING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; POSITRON EMISSION TOMOGRAPHY; PRECURSOR; PRIORITY JOURNAL; RADIOCHEMISTRY;

EID: 84902524489     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml500065q     Document Type: Article

References (25)

1. Huang, P.; Chandra, V.; Rastinejad, F. Retinoic Acid Actions through Mammalian Nuclear Receptors Chem. Rev. 2014, 114, 233-254
2. Moreno, S.; Farioli-Vecchioli, S.; Cerù, M. P. Immunolocalization of Peroxisome Proliferator-Activated Receptors and Retinoid X Receptors in the Adult Rat CNS Neuroscience 2004, 123, 131-145
3. Goodman, A. B.; Pardee, A. B. Evidence for Defective Retinoid Transport and Function in Late Onset Alzheimer's Disease Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 2901-2905
4. Boehm, M. F.; Zhang, L.; Badea, B. A.; White, S. K.; Mais, D. E.; Berger, E.; Suto, C. M.; Goldman, M. E.; Heyman, R. A. Synthesis and Structure-Activity Relationships of Novel Retinoid X Receptor-Selective Retinoids J. Med. Chem. 1994, 37, 2930-2941
5. Cramer, P. E.; Cirrito, J. R.; Wesson, D. W.; Lee, C. Y. D.; Karlo, J. C.; Zinn, A. E.; Casali, B. T.; Restivo, J. L.; Goebel, W. D.; James, M. J.; Brunden, K. R.; Wilson, D. A.; Landreth, G. E. ApoE-Directed Therapeutics Rapidly Clear β -Amyloid and Reverse Deficits in AD Mouse Models Science 2012, 335, 1503-1506
6. Bachmeier, C.; Beaulieu-Abdelahad, D.; Crawford, F.; Mullan, M.; Paris, D. Stimulation of the Retinoid X Receptor Facilitates Beta-Amyloid Clearance Across the Blood-Brain Barrier J. Mol. Neurosci. 2012, 49, 270-276
7. Fitz, N. F.; Cronican, A. A.; Lefterov, I.; Koldamova, R. Comment on "ApoE-Directed Therapeutics Rapidly Clear β -Amyloid and Reverse Deficits in AD Mouse Models" Science 2013, 340, 924-924
8. Price, A. R.; Xu, G.; Siemienski, Z. B.; Smithson, L. A.; Borchelt, D. R.; Golde, T. E.; Felsenstein, K. M. Comment on "ApoE-Directed Therapeutics Rapidly Clear β -Amyloid and Reverse Deficits in AD Mouse Models" Science 2013, 340, 924-924
9. Tesseur, I.; Lo, A. C.; Roberfroid, A.; Dietvorst, S.; Van Broeck, B.; Borgers, M.; Gijsen, H.; Moechars, D.; Mercken, M.; Kemp, J.; D'Hooge, R.; De Strooper, B. Comment on "ApoE-Directed Therapeutics Rapidly Clear β -Amyloid and Reverse Deficits in AD Mouse Models" Science 2013, 340, 924-924
10. Veeraraghavalu, K.; Zhang, C.; Miller, S.; Hefendehl, J. K.; Rajapaksha, T. W.; Ulrich, J.; Jucker, M.; Holtzman, D. M.; Tanzi, R. E.; Vassar, R.; Sisodia, S. S. Comment on "ApoE-Directed Therapeutics Rapidly Clear β -Amyloid and Reverse Deficits in AD Mouse Models" Science 2013, 340, 924-924
11. Landreth, G. E.; Cramer, P. E.; Lakner, M. M.; Cirrito, J. R.; Wesson, D. W.; Brunden, K. R.; Wilson, D. A. Response to Comments on "ApoE-Directed Therapeutics Rapidly Clear β -Amyloid and Reverse Deficits in AD Mouse Models" Science 2013, 340, 924-924
12. Corbett, A.; Pickett, J.; Burns, A.; Corcoran, J.; Dunnett, S. B.; Edison, P.; Hagan, J. J.; Holmes, C.; Jones, E.; Katona, C. Drug Repositioning for Alzheimer's Disease Nat. Rev. Drug Discovery 2012, 11, 833-846
13. Lowenthal, J.; Hull, S. C.; Pearson, S. D. The Ethics of Early Evidence - Preparing for a Possible Breakthrough in Alzheimer's Disease N. Engl. J. Med. 2012, 367, 488-490
14. Ametamey, S. M.; Honer, M.; Schubiger, P. A. Molecular Imaging with PET Chem. Rev. 2008, 108, 1501-1516
15. 13N Radiolabels for Positron Emission Tomography Angew. Chem., Int. Ed. 2008, 47, 8998-9033
16. 11C]methylation J. Labelled Compd. Radiopharm. 2011, 54, S92
17. 11C]Carbon Monoxide ACS Med. Chem. Lett. 2012, 3, 804-807
18. 2 Fixation: A Renaissance in PET Radiochemistry Chem. Commun. 2013, 49, 5621-5629
19. 11C-Labeled Carboxylic Acids, Esters, and Amides Angew. Chem., Int. Ed. 2012, 51, 2698-2702
20. Sarshar, S. Novel Therapeutic Agents for the Treatment of Cancer, Metabolic Diseases and Skin Disorders. WO2007022437 (A2), February 22, 2007.
21. 2 into Carbamates Angew. Chem., Int. Ed. 2009, 48, 3482-3485
22. 11C- carbonyl ]-Methylcarbamates Org. Biomol. Chem. 2010, 8, 428-432
23. Wilson, A. A.; Jin, L.; Garcia, A.; DaSilva, J. N.; Houle, S. An Admonition When Measuring the Lipophilicity of Radiotracers Using Counting Techniques Appl. Radiat. Isot. 2001, 54, 203-208
24. Cullingford, T. E.; Bhakoo, K.; Peuchen, S.; Dolphin, C. T.; Patel, R.; Clark, J. B. Distribution of mRNAs Encoding the Peroxisome Proliferator- Activated Receptor α, β, and Î and the Retinoid X Receptor α, β, and Î in Rat Central Nervous System J. Neurochem. 1998, 70, 1366-1375
25. Howell, S. R.; Shirley, M. A.; Grese, T. A.; Neel, D. A.; Wells, K. E.; Ulm, E. H. Bexarotene Metabolism in Rat, Dog, and Human, Synthesis of Oxidative Metabolites, and in Vitro Activity at Retinoid Receptors Drug Metab. Dispos. 2001, 29, 990-998