A philosophy for CNS radiotracer design

Accounts of Chemical Research

Volumn 47, Issue 10, 2014, Pages 3127-3134

  Van De Bittner, Genevieve C ^a   Ricq, Emily L ^a,b   Hooker, Jacob M ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRACER;

CENTRAL NERVOUS SYSTEM; HUMAN; POSITRON EMISSION TOMOGRAPHY; SCINTISCANNING;

CENTRAL NERVOUS SYSTEM; HUMANS; POSITRON-EMISSION TOMOGRAPHY; RADIOACTIVE TRACERS;

EID: 84908112282     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500233s     Document Type: Article

References (53)

1. Lockwood, A. H. Invasiveness in Studies of Brain Function by Positron Emission Tomography (PET) J. Cereb. Blood Flow Metab. 1985, 5, 487-489
2. Eriksson, L.; Kanno, I. Blood Sampling Devices and Measurements Med. Prog. Technol. 1991, 17, 249-257
3. Zimmer, L.; Luxen, A. PET Radiotracers for Molecular Imaging in the Brain: Past, Present and Future NeuroImage 2012, 61, 363-370
4. Hargreaves, R. J.; Rabiner, E. A. Translational PET Imaging Research Neurobiol. Dis. 2014, 61, 32-38
5. CNS Radiotracer Table http://www.nimh.nih.gov/research-priorities/therapeutics/cns-radiotracer-table.shtml (accessed Jun 17, 2014).
6. Martins-de-Souza, D.; Carvalho, P. C.; Schmitt, A.; Junqueira, M.; Nogueira, F. C. S.; Turck, C. W.; Domont, G. B. Deciphering the Human Brain Proteome: Characterization of the Anterior Temporal Lobe and Corpus Callosum as Part of the Chromosome 15-Centric Human Proteome Project J. Proteome Res. 2014, 13, 147-157
7. Jones, T.; Rabiner, E. A. PET Research Advisory Company. The Development, Past Achievements, and Future Directions of Brain PET J. Cereb. Blood Flow Metab. 2012, 32, 1426-1454
8. Ho, N. F.; Hooker, J. M.; Sahay, A.; Holt, D. J.; Roffman, J. L. In Vivo Imaging of Adult Human Hippocampal Neurogenesis: Progress, Pitfalls and Promise Mol. Psychiatry 2013, 18, 404-416
9. Wang, C.; Schroeder, F. A.; Hooker, J. M. Visualizing Epigenetics: Current Advances and Advantages in HDAC PET Imaging Techniques Neuroscience 2014, 264, 186-197
10. Schroeder, F. A.; Wang, C.; Van de Bittner, G.; Neelamegam, R.; Takakura, W.; Karunakaran, P.; Wey, H.-Y.; Reis, S.; Gale, J. P.; Zhang, Y.-L.; Holson, E.; Haggarty, S.; Hooker, J. PET Imaging Demonstrates Histone Deacetylase Target Engagement and Clarifies Brain Penetrance of Known and Novel Small Molecule Inhibitors in Rat ACS Chem. Neurosci. 2014, 10.1021/cn500162j
11. Biegon, A.; Kim, S. W.; Alexoff, D. L.; Jayne, M.; Carter, P.; Hubbard, B.; King, P.; Logan, J.; Muench, L.; Pareto, D.; Schlyer, D.; Shea, C.; Telang, F.; Wang, G.-J.; Xu, Y.; Fowler, J. S. Unique Distribution of Aromatase in the Human Brain: In Vivo Studies with PET and [N-Methyl-11C]vorozole Synapse 2010, 64, 801-807
12. Kim, S. W.; Hooker, J. M.; Otto, N.; Win, K.; Muench, L.; Shea, C.; Carter, P.; King, P.; Reid, A. E.; Volkow, N. D.; Fowler, J. S. Whole-Body Pharmacokinetics of HDAC Inhibitor Drugs, Butyric Acid, Valproic Acid and 4-Phenylbutyric Acid Measured with Carbon-11 Labeled Analogs by PET Nucl. Med. Biol. 2013, 40, 912-918
13. Seo, Y. J.; Muench, L.; Reid, A.; Chen, J.; Kang, Y.; Hooker, J. M.; Volkow, N. D.; Fowler, J. S.; Kim, S. W. Radionuclide Labeling and Evaluation of Candidate Radioligands for PET Imaging of Histone Deacetylase in the Brain Bioorg. Med. Chem. Lett. 2013, 23, 6700-6705
14. Wang, C.; Eessalu, T. E.; Barth, V. N.; Mitch, C. H.; Wagner, F. F.; Hong, Y.; Neelamegam, R.; Schroeder, F. A.; Holson, E. B.; Haggarty, S. J.; Hooker, J. M. Design, Synthesis, and Evaluation of Hydroxamic Acid-Based Molecular Probes for in Vivo Imaging of Histone Deacetylase (HDAC) in Brain Am. J. Nucl. Med. Mol. Imaging 2013, 4, 29-38
15. Seo, Y. J.; Kang, Y.; Muench, L.; Reid, A.; Caesar, S.; Jean, L.; Wagner, F.; Holson, E.; Haggarty, S. J.; Weiss, P.; King, P.; Carter, P.; Volkow, N. D.; Fowler, J. S.; Hooker, J. M.; Kim, S. W. Image-Guided Synthesis Reveals Potent Blood-Brain Barrier Permeable Histone Deacetylase Inhibitors ACS Chem. Neurosci. 2014, 5, 588-596
16. Nordberg, A. PET Tracers for Beta-Amyloid and Other Proteinopathies. In PET and SPECT of Neurobiological Systems; Dierckx, R. A. J. O.; Otte, A.; de Vries, E. F. J.; van Waarde, A.; Luiten, P. G. M., Eds.; Springer: Berlin Heidelberg, 2014; pp 199-212.
17. Zhang, L.; Villalobos, A.; Beck, E. M.; Bocan, T.; Chappie, T. A.; Chen, L.; Grimwood, S.; Heck, S. D.; Helal, C. J.; Hou, X.; Humphrey, J. M.; Lu, J.; Skaddan, M. B.; McCarthy, T. J.; Verhoest, P. R.; Wager, T. T.; Zasadny, K. Design and Selection Parameters to Accelerate the Discovery of Novel Central Nervous System Positron Emission Tomography (PET) Ligands and Their Application in the Development of a Novel Phosphodiesterase 2A PET Ligand J. Med. Chem. 2013, 56, 4568-4579
18. Ferré, S.; Casadó, V.; Devi, L. A.; Filizola, M.; Jockers, R.; Lohse, M. J.; Milligan, G.; Pin, J.-P.; Guitart, X. G Protein-Coupled Receptor Oligomerization Revisited: Functional and Pharmacological Perspectives Pharmacol. Rev. 2014, 66, 413-434
19. Sander, C. Y.; Hooker, J. M.; Catana, C.; Normandin, M. D.; Alpert, N. M.; Knudsen, G. M.; Vanduffel, W.; Rosen, B. R.; Mandeville, J. B. Neurovascular Coupling to D2/D3 Dopamine Receptor Occupancy Using Simultaneous PET/functional MRI Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 11169-11174
20. Patel, S.; Gibson, R. In Vivo Site-Directed Radiotracers: A Mini-Review Nucl. Med. Biol. 2008, 35, 805-815
21. Wang, Y.; Zhang, Y.-L.; Hennig, K.; Gale, J. P.; Hong, Y.; Cha, A.; Riley, M.; Wagner, F.; Haggarty, S. J.; Holson, E.; Hooker, J. Class I HDAC Imaging Using [(3)H]CI-994 Autoradiography Epigenetics 2013, 8, 756-764
22. Gage, H. D.; Voytko, M. L.; Ehrenkaufer, R. L.; Tobin, J. R.; Efange, S. M.; Mach, R. H. Reproducibility of Repeated Measures of Cholinergic Terminal Density Using [18F](+)-4-Fluorobenzyltrozamicol and PET in the Rhesus Monkey Brain J. Nucl. Med. 2000, 41, 2069-2076
23. 11C]FLB 457: Reproducibility Studies Synapse 2011, 65, 35-40
24. Wahl, L. M.; Nahmias, C. Statistical Power Analysis for PET Studies in Humans J. Nucl. Med. 1998, 39, 1826-1829
25. Stephenson, K. A.; van Oosten, E. M.; Wilson, A. A.; Meyer, J. H.; Houle, S.; Vasdev, N. Synthesis and Preliminary Evaluation of [(18)F]-Fluoro-(2S)-Exaprolol for Imaging Cerebral Beta-Adrenergic Receptors with PET Neurochem. Int. 2008, 53, 173-179
26. Wang, C.; Wilson, C. M.; Moseley, C. K.; Carlin, S. M.; Hsu, S.; Arabasz, G.; Schroeder, F. A.; Sander, C. Y.; Hooker, J. M. Evaluation of Potential PET Imaging Probes for the Orexin 2 Receptors Nucl. Med. Biol. 2013, 40, 1000-1005
27. Neelamegam, R.; Hellenbrand, T.; Schroeder, F. A.; Wang, C.; Hooker, J. M. Imaging Evaluation of 5HT2C Agonists, [(11)C]WAY-163909 and [(11)C]Vabicaserin, Formed by Pictet-Spengler Cyclization J. Med. Chem. 2014, 57, 1488-1494
28. Horti, A. G.; Gao, Y.; Kuwabara, H.; Dannals, R. F. Development of Radioligands with Optimized Imaging Properties for Quantification of Nicotinic Acetylcholine Receptors by Positron Emission Tomography Life Sci. 2010, 86, 575-584
29. Pike, V. W. PET Radiotracers: Crossing the Blood-Brain Barrier and Surviving Metabolism Trends Pharmacol. Sci. 2009, 30, 431-440
30. Wang, C.; Schroeder, F. A.; Wey, H.-Y.; Borra, R.; Wagner, F.; Reis, S.; Kim, S. W.; Holson, E. B.; Haggarty, S. J.; Hooker, J. M. In Vivo Imaging of Histone Deacetylases (HDACs) in the Central Nervous System and Major Peripheral Organs J. Med. Chem. 2014, 10.1021/jm500872p
31. Hooker, J. M. Modular Strategies for PET Imaging Agents Curr. Opin. Chem. Biol. 2010, 14, 105-111
32. Sutcliffe-Goulden, J. L.; O"Doherty, M. J.; Marsden, P. K.; Hart, I. R.; Marshall, J. F.; Bansal, S. S. Rapid Solid Phase Synthesis and Biodistribution of 18F-Labelled Linear Peptides Eur. J. Nucl. Med. Mol. Imaging 2002, 29, 754-759
33. Gagnon, M. K. J.; Hausner, S. H.; Marik, J.; Abbey, C. K.; Marshall, J. F.; Sutcliffe, J. L. High-Throughput in Vivo Screening of Targeted Molecular Imaging Agents Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 17904-17909
34. Miller, P. W.; Long, N. J.; Vilar, R.; Gee, A. D. Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography Angew. Chem., Int. Ed. 2008, 47, 8998-9033
35. Cole, E. L.; Stewart, M. N.; Littich, R.; Hoareau, R.; Scott, P. J. H. Radiosyntheses Using Fluorine-18: The Art and Science of Late Stage Fluorination Curr. Top. Med. Chem. 2014, 14, 875-900
36. Zhang, M.-R.; Suzuki, K. [18F]Fluoroalkyl Agents: Synthesis, Reactivity and Application for Development of PET Ligands in Molecular Imaging Curr. Top. Med. Chem. 2007, 7, 1817-1828
37. Pretze, M.; Pietzsch, D.; Mamat, C. Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18 Molecules 2013, 18, 8618-8665
38. Lee, E.; Kamlet, A. S.; Powers, D. C.; Neumann, C. N.; Boursalian, G. B.; Furuya, T.; Choi, D. C.; Hooker, J. M.; Ritter, T. A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging Science 2011, 334, 639-642
39. Lee, E.; Hooker, J. M.; Ritter, T. Nickel-Mediated Oxidative Fluorination for PET with Aqueous [18F] Fluoride J. Am. Chem. Soc. 2012, 134, 17456-17458
40. Kamlet, A. S.; Neumann, C. N.; Lee, E.; Carlin, S. M.; Moseley, C. K.; Stephenson, N.; Hooker, J. M.; Ritter, T. Application of Palladium-Mediated 18F-Fluorination to PET Radiotracer Development: Overcoming Hurdles to Translation PLoS One 2013, 8 e59187
41. Huang, X.; Liu, W.; Ren, H.; Neelamegam, R.; Hooker, J. M.; Groves, J. T. Late Stage Benzylic C-H Fluorination with [18F]Fluoride for PET Imaging J. Am. Chem. Soc. 2014, 136, 6842-6845
42. 18F]MDL100907 Enabled by Ni-Mediated Fluorination ACS Chem. Neurosci. 2014, 5, 611-615
43. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings Adv. Drug Delivery Rev. 2001, 46, 3-26
44. Ryu, Y. H.; Liow, J.-S.; Zoghbi, S.; Fujita, M.; Collins, J.; Tipre, D.; Sangare, J.; Hong, J.; Pike, V. W.; Innis, R. B. Disulfiram Inhibits Defluorination of (18)F-FCWAY, Reduces Bone Radioactivity, and Enhances Visualization of Radioligand Binding to Serotonin 5-HT1A Receptors in Human Brain J. Nucl. Med. 2007, 48, 1154-1161
45. Laruelle, M.; Slifstein, M.; Huang, Y. Positron Emission Tomography: Imaging and Quantification of Neurotransporter Availability Methods 2002, 27, 287-299
46. NIMH Psychoactive Drug Screening Program. http://pdsp.med.unc.edu/ (accessed Jun 17, 2014).
47. Hooker, J. M.; Kim, S. W.; Reibel, A. T.; Alexoff, D.; Xu, Y.; Shea, C. Evaluation of [11C]Metergoline as a PET Radiotracer for 5HTR in Nonhuman Primates Bioorg. Med. Chem. 2010, 18, 7739-7745
48. Patel, S.; Hamill, T.; Hostetler, E.; Burns, H. D.; Gibson, R. E. An in Vitro Assay for Predicting Successful Imaging Radiotracers Mol. Imaging Biol. 2003, 5, 65-71
49. Barth, V.; Need, A. Identifying Novel Radiotracers for PET Imaging of the Brain: Application of LC-MS/MS to Tracer Identification ACS Chem. Neurosci. 2014, 10.1021/cn500072r
50. Tournier, N.; Saba, W.; Cisternino, S.; Peyronneau, M.-A.; Damont, A.; Goutal, S.; Dubois, A.; Dollé, F.; Scherrmann, J.-M.; Valette, H.; Kuhnast, B.; Bottlaender, M. Effects of Selected OATP And/or ABC Transporter Inhibitors on the Brain and Whole-Body Distribution of Glyburide AAPS J. 2013, 15, 1082-1090
51. Syvänen, S.; Lindhe, Ö.; Palner, M.; Kornum, B. R.; Rahman, O.; Långström, B.; Knudsen, G. M.; Hammarlund-Udenaes, M. Species Differences in Blood-Brain Barrier Transport of Three Positron Emission Tomography Radioligands with Emphasis on P-Glycoprotein Transport Drug Metab. Dispos. 2009, 37, 635-643
52. Varnäs, K.; Varrone, A.; Farde, L. Modeling of PET Data in CNS Drug Discovery and Development J. Pharmacokinet. Pharmacodyn. 2013, 40, 267-279
53. Kuntner, C. Kinetic Modeling in Preclinical Positron Emission Tomography Z. Med. Phys. 2014, 10.1016/j.zemedi.2014.02.003