Application of Palladium-Mediated 18F-Fluorination to PET Radiotracer Development: Overcoming Hurdles to Translation

PLoS ONE

Volumn 8, Issue 3, 2013, Pages

  Kamlet, Adam S ^a   Neumann, Constanze N ^a   Lee, Eunsung ^a   Carlin, Stephen M ^b   Moseley, Christian K ^b   Stephenson, Nickeisha ^a   Hooker, Jacob M ^b   Ritter, Tobias ^a,b  

^a HARVARD UNIVERSITY   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE PAROXETINE F 18; FLUORINE SEROTONIN 2C AGONIST F 18; PALLADIUM COMPLEX; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BABOON; CHEMICAL BOND; DRUG DISTRIBUTION; DRUG PENETRATION; ELECTROPHILICITY; FLUORINATION; IN VIVO STUDY; ISOTOPE ANALYSIS; ISOTOPE LABELING; NONHUMAN; OXIDATION KINETICS; POSITRON EMISSION TOMOGRAPHY; PREDICTION; PROCESS DEVELOPMENT; PROCESS OPTIMIZATION; RADIOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS;

ANIMALS; FLUORIDES; FLUORINE RADIOISOTOPES; HALOGENATION; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PAPIO; PAROXETINE; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; SEROTONIN 5-HT2 RECEPTOR AGONISTS;

EID: 84874831608     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0059187     Document Type: Article

References (53)

1. Fowler JS, Wolf AP, (1997) Working against Time: Rapid Radiotracer Synthesis and Imaging the Human Brain. Acc Chem Res 30: 181-188.
2. Phelps ME, (2000) Positron emission tomography provides molecular imaging of biological processes. P Natl Acad Sci USA 97: 9226-9233.
3. Miller PW, Long NJ, Vilar R, Gee AD, (2008) Synthesis of C-11, F-18, O-15, and N-13 Radiolabels for Positron Emission Tomography. Angew Chem, Int Ed 47: 8998-9033.
4. Ametamey SM, Honer M, Schubiger PA, (2008) Molecular imaging with PET. Chem Rev 108: 1501-1516.
5. Muller K, Faeh C, Diederich F, (2007) Fluorine in pharmaceuticals: Looking beyond intuition. Science 317: 1881-1886.
6. Purser S, Moore PR, Swallow S, Gouverneur V, (2008) Fluorine in medicinal chemistry. Chem Soc Rev 37: 320-330.
7. Cai LS, Lu SY, Pike VW (2008) Chemistry with [F-18]fluoride ion. Eur J Org Chem: 2853-2873.
8. Furuya T, Kuttruff CA, Ritter T, (2008) Carbon-fluorine bond formation. Curr Opin Drug Discov Devel 11: 803-819.
9. Furuya T, Kamlet AS, Ritter T, (2011) Catalysis for fluorination and trifluoromethylation. Nature 473: 470-477.
10. O'Hagan D, (2008) Understanding organofluorine chemistry. An introduction to the C-F bond. Chem Soc Rev 37: 308-319.
11. Bergman J, Solin O, (1997) Fluorine-18-labeled fluorine gas for synthesis of tracer molecules. Nucl Med Biol 24: 677-683.
12. Emsley J, (1980) Very Strong Hydrogen-Bonding. Chem Soc Rev 9: 91-124.
13. Hummer G, Pratt LR, Garcia AE, (1996) Free energy of ionic hydration. J Phys Chem 100: 1206-1215.
14. Cabarcos OM, Weinheimer CJ, Lisy JM, Xantheas SS, (1999) Microscopic hydration of the fluoride anion. J Chem Phys 110: 5-8.
15. Serdons K, Verbruggen A, Bormans GM, (2009) Developing new molecular imaging probes for PET. Methods 48: 104-111.
16. Serdons K, Terwinghe C, Van Vermaelen P, Laere K, Kung H, et al. (2009) Synthesis and Evaluation of 18F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer's Disease. J Med Chem 52: 1428-1437.
17. Antoni G, Langstrom B (2008) Radiopharmaceuticals: molecular imaging using positron emission tomography. Handb Exp Pharmacol: 177-201.
18. Modern Medicine website. Available: http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/252011/727243/article.pdf. Accessed 2013 Feb 14.
19. Landvatter SW, Garnes KT, Dannals RF (1998) Progress in the synthesis of paroxetine-[18F]. In: Heys JR, Melillo DG, editors. Synthesis and Applications of Isotopically Labelled Compounds 1997. England: John Wiley & Sons Ltd. 99-102.
20. Suehiro M, Wilson AA, Scheffel U, Dannals RF, Ravert HT, et al. (1991) Radiosynthesis and Evaluation of N-(3-F-18 fluoropropyl)paroxetine as a Radiotracer for In Vivo Labeling of Serotonin Uptake Sites by PET. Nucl Med Biol 18: 791-796.
21. Kozikowski AP, Cho SJ, Jensen NH, Allen JA, Svennebring AM, et al. (2010) HTS and Rational Drug Design to Generate a Class of 5-HT2C-Selective Ligands for Possible Use in Schizophrenia. ChemMedChem 5: 1221-1225.
22. O'Neil PM, Smith SR, Weissman NJ, Fidler MC, Sanchez M, et al. (2012) Randomized Placebo-Controlled Clinical Trial of Lorcaserin for Weight Loss in Type 2 Diabetes Mellitus: The BLOOM-DM Study. Obesity 20: 1426-1436.
23. Saulin A, Savli M, Lanzenberger R, (2012) Serotonin and molecular neuroimaging in humans using PET. Amino Acids 42: 2039-2057.
24. Lee E, Kamlet AS, Powers DC, Neumann CN, Boursalian GB, et al. (2011) A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging. Science 334: 639-642.
25. Teare H, Robins EG, Arstad E, Sajinder KL, Gouverneur V (2007) Synthesis and reactivity of [F-18]-N-fluorobenzenesulfonimide. Chem Comm: 2330-2332.
26. Teare H, Robins EG, Kirjavainen A, Forsback S, Sandford G, et al. (2010) Radiosynthesis and Evaluation of (18)F Selectfluor bis(triflate). Angew Chem, Int Ed 49: 6821-6824.
27. Fowler JS, Shiue CY, Wolf AP, Salvadori PA, Macgregor RR, (1982) Synthesis of F-18-labeled acetyl hypofluorite for radiotracer synthesis. J Labelled Compd Radiopharm 19: 1634-1636.
28. Furuya T, Ritter T, (2008) Carbon-fluorine reductive elimination from a high-valent palladium fluoride. J Am Chem Soc 130: 10060-10061.
29. Furuya T, Benitez D, Tkatchouk E, Strom AE, Tang PP, et al. (2010) Mechanism of C-F Reductive Elimination from Palladium(IV) Fluorides. J Am Chem Soc 132: 3793-3807.
30. Furuya T, Kaiser HM, Ritter T, (2008) Palladium-mediated fluorination of arylboronic acids. Angew Chem, Int Ed 47: 5993-5996.
31. Luedtke AT, Goldberg KI, (2007) Reductive elimination of ethane from five-coordinate platinum(IV) alkyl complexes. Inorg Chem 46: 8496-8498.
32. Hughes G, Kimura M, Buchwald SL, (2003) Catalytic enantioselective conjugate reduction of lactones and lactams. J Am Chem Soc 125: 11253-11258.
33. Charette AB, Juteau H, Lebel H, Molinaro C, (1998) Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications. J Am Chem Soc 120: 11943-11952.
34. Cai L, Lu S, Pike VW, (2008) Chemistry with [18F]Fluoride Ion. Eur J Org Chem 2008: 2853-2873.
35. Shao X, Hoareau R, Hockley BG, Tluczek LJM, Henderson BD, et al. (2011) Highlighting the versatility of the tracerlab synthesis modules. Part 1: fully automated production of F-18 labelled radiopharmaceuticals using a Tracerlab FXFN. J Labelled Compd Radiopharm 54: 292-307.
36. European Medicines Agency website. Available: www.ema.europa.eu/docs/en_GB/document_library/Scientific_guideline/2009/09/WC500003587.pdf. Accessed 2013 Feb 14.
37. Owens MJ, Morgan WN, Plott SJ, Nemeroff CB, (1997) Neurotransmitter Receptor and Transporter Binding Profile of Antidepressants and Their Metabolites. J Pharmacol Exp Ther 283: 1305-1322.
38. Jiang ZJ, Reilly J, Everatt B, Briard E, (2011) A rapid vesicle electrokinetic chromatography method for the in vitro prediction of non-specific binding for potential PET ligands. J Pharmaceut Biomed 54: 722-729.
39. Hinz R, Selvaraj S, Murthy NV, Bhagwagar Z, Taylor M, et al. (2008) Effects of citalopram infusion on the serotonin transporter binding of C-11 DASB in healthy controls. J Cerebr Blood F Met 28: 1478-1490.
40. Coenen HH, Wienhard K, Stocklin G, Laufer P, Hebold I, et al. (1988) PET Measurement of D2 and S2 Receptor-Binding of 3-N(2′-F-18 fluoroethyl)spiperone in Baboon Brain. Eur J Nucl Med 14: 80-87.
41. Pinborg LH, Feng L, Haahr ME, Gillings N, Dyssegaard A, et al. (2012) No change in [11C]CUMI-101 binding to 5-HT1A receptors after intravenous citalopram in human. Synapse (New York) 66: 880-884.
42. Centurion D, Sanchez-Lopez A, Ortiz MI, De Vries P, Saxena PR, et al. (2000) Mediation of 5-HT-induced internal carotid vasodilatation in GR127935-and ritanserin-pretreated dogs by 5-HT7 receptors. N-S Arch Pharmacol 362: 169-176.
43. Bergstrom M, Grahnen A, Langstrom B, (2003) Positron emission tomography microdosing: a new concept with application in tracer and early clinical drug development. Eur J Clin Pharmacol 59: 357-366.
44. Wang JL, Maurer L, (2005) Positron emission tomography: Applications in drug discovery and drug development. Curr Top Med Chem 5: 1053-1075.
45. GlaxoSmithKline website. Available: http://www.gsk.ca/english/docs-pdf/Paxil_2011.pdf. Accessed 2013 Feb 14.
46. Monck NJ, Kennett GA, (2008) 5-HT2C ligands: recent progress. Prog Med Chem 46: 281-390.
47. Christianson JP, Ragole T, Amat J, Greenwood BN, Strong PV, et al. (2010) 5-Hydroxytryptamine 2C Receptors in the Basolateral Amygdala Are Involved in the Expression of Anxiety After Uncontrollable Traumatic Stress. Biol Psychiat 67: 339-345.
48. Siuciak JA, Chapin DS, McCarthy SA, Guanowsky V, Brown J, et al. (2007) CP-809,101, a selective 5-HT2C agonist, shows activity in animal models of antipsychotic activity. Neuropharmacology 52: 279-290.
49. Pandey SC, Lumeng L, Li TK, (1996) Serotonin(2C) receptors and serotonin(2C) receptor-mediated phosphoinositide hydrolysis in the brain of alcohol-preferring and alcohol-nonpreferring rats. Alcohol Clin Exp Res 20: 1038-1042.
50. Knight AR, Misra A, Quirk K, Benwell K, Revell D, et al. (2004) Pharmacological characterisation of the agonist radioligand binding site of 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S Arch Pharmacol 370: 114-123.
51. Lopez-Gimenez JF, Mengod G, Palacios JM, Vilaro MT, (2001) Regional distribution and cellular localization of 5-HT2C receptor mRNA in monkey brain: Comparison with H-3 mesulergine binding sites and choline acetyltransferase mRNA. Synapse (New York) 42: 12-26.
52. Pasqualetti M, Ori M, Castagna M, Marazziti D, Cassano GB, et al. (1999) Distribution and cellular localization of the serotonin type 2C receptor messenger RNA in human brain. Neuroscience 92: 601-611.
53. Lee E, Hooker JM, Ritter T, (2012) Nickel-Mediated Oxidative Fluorination for PET with Aqueous F-18 Fluoride. J Am Chem Soc 134: 17456-17458.