Challenges for developing PET tracers: Isotopes, chemistry, and regulatory aspects

PET Clinics

Volumn 5, Issue 2, 2010, Pages 131-153

  Mach, Robert H ^a   Schwarz, Sally W ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Carbon 11; Chemistry; Fluorine 18; PET regulatory

Indexed keywords

CARBON 11; FLUORINE 18; ISOTOPE; NEUROTRANSMITTER RECEPTOR; NITROGEN 13; OXYGEN 15; TRACER;

ARTICLE; BRAIN BLOOD FLOW; BRAIN FUNCTION; BRAIN REGION; CENTRAL NERVOUS SYSTEM; CORPUS STRIATUM; HUMAN; NERVE CELL NETWORK; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOCHEMISTRY; SECOND MESSENGER;

EID: 79954595067     PISSN: 15568598     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cpet.2010.02.002     Document Type: Article

References (80)

1. Luedtke RR, Mach RH. Progress in developing D3 dopamine receptor ligands as potential therapeutic agents for neurological and neuropsychiatric disorders. Curr Pharm Des 2003;9(8):643-71.
2. Ryoo HL, Pierrotti D, Joyce JN. Dopamine D3 receptor is decreased and D2 receptor is elevated in the striatum of Parkinson's disease. Mov Disord 1998;13(5):788-97. (Pubitemid 28429977)
3. Moore RJ, et al. Effect of cocaine self-administration on dopamine D2 receptors in rhesus monkeys. Synapse 1998;30(1):88-96. (Pubitemid 28361187)
4. Nader MA, et al. PET imaging of dopamine D2 receptors during chronic cocaine self-administration in monkeys. Nat Neurosci 2006;9(8):1050-6. (Pubitemid 44264918)
5. Volkow ND, Fowler JS, Wang GJ, et al. Dopamine in drug abuse and addiction: results from imaging studies and treatment implications. Mol Psychiatry 2004;9(6):557-69. (Pubitemid 38850435)
6. Volkow ND, Fowler JS, Wolf AP, et al. Effects of chronic cocaine abuse on postsynaptic dopamine receptors. Am J Psychiatry 1990;147(6):719-24. (Pubitemid 20188509)
7. Staley JK, Mash DC. Adaptive increase in D3 dopamine receptors in the brain reward circuits of human cocaine fatalities. J Neurosci 1996;16(19):6100-6. (Pubitemid 26313985)
8. Hannon J, Hoyer D. Molecular biology of 5-HT receptors. Behav Brain Res 2008;195(1):198-213.
9. Carroll FI. Antagonists at metabotropic glutamate receptor subtype 5: structure activity relationships and therapeutic potential for addiction. Ann N Y Acad Sci 2008;1141:221-32.
10. Hein L. Adrenoceptors and signal transduction in neurons. Cell Tissue Res 2006;326(2):541-51. (Pubitemid 44435825)
11. Harper DB, O'Hagan D. The fluorinated natural products. Nat Prod Rep 1994;11(2):123-33.
12. Filler R, Kobayashi Y, Yagulpolskii LM. Organofluorine compounds in medicinal chemistry and biomedical applications. Studies in Organic Chemistry, vol. 48. Amsterdam (The Netherlands): Elsevier; 1993. p. 394.
13. Hammadi A, Crouzel C. Synthesis of [18F]-(S)-fluoxetine: a selective serotonine uptake inhibitor. J Labelled Comp Radiopharm 1993;33(8):703-10. (Pubitemid 23228630)
14. Das MK, Mukherjee J. Radiosynthesis of [F-18]fluoxetine as a potential radiotracer for serotonin reuptake sites. Appl Radiat Isot 1993;44(5):835-42. (Pubitemid 23113745)
15. Suehiro M, Wilson AA, Scheffel U, et al. Radiosynthesis and evaluation of N-(3-[18F]fluoropropyl)paroxetine as a radiotracer for in vivo labeling of serotonin uptake sites by PET. Nucl Med Biol 1991; 18(7):791-6.
16. Shiue CY, Fowler JS, Wolf AP, et al. Syntheses and specific activity determinations of no-carrier-added (NCA) F-18-labeled butyrophenone neuroleptics-benperidol, haloperidol, spiroperidol, and pipamperone. J Nucl Med 1985;26(2):181-6.
17. Hamacher K, Hamkens W. Remote controlled onestep production of 18F labeled butyrophenone neuroleptics exemplified by the synthesis of n.c.a. [18F] N-methylspiperone. Appl Radiat Isot 1995;46(9): 911-6.
18. Katsifis A, Hamacher K, Schnitter J, et al. Optimization studies concerning the direct nucleophilic fluorination of butyrophenone neuroleptics. Appl Radiat Isot 1993;44(7):1015-20. (Pubitemid 23187991)
19. Crouzel C, Venet M, Irie T, et al. Labeling of a serotoninergic ligand with 18F: [18F] setoperone. J Labelled Comp Radiopharm 1988;25(4): 403-14. (Pubitemid 18095787)
20. Mach RH, Luedtke RR, Unsworth CD, et al. 18F-labeled benzamides for studying the dopamine D2 receptor with positron emission tomography. J Med Chem 1993;36(23):3707-20. (Pubitemid 24004370)
21. Schlyer DJ. PET tracers and radiochemistry. Ann Acad Med Singapore 2004;33(2):146-54. (Pubitemid 38684849)
22. Elsinga PH. Radiopharmaceutical chemistry for positron emission tomography. Methods 2002; 27(3):208-17.
23. Pike V, Eakins M, Allan R, et al. Preparation of carbon-11 labelled acetate and palmitic acid for the study of myocardial metabolism by emissioncomputerised axial tomography. J Radioanal Nucl Chem 1981;64(1):291-7.
24. McCarron JA, Turton DR, Pike VW, et al. Remotely-controlled production of the 5-HT1A receptor radioligand, [carbonyl-11C]WAY-100635, via 11C-carboxylation of an immobilized Grignard reagent. J Labelled Comp Radiopharm 1996; 38(10):941-53. (Pubitemid 26338669)
25. Yasuno F, Suhara T, Ichimiya T, et al. Decreased 5-HT1A receptor binding in amygdala of schizophrenia. Biol Psychiatry 2004;55(5):439-44. (Pubitemid 38338529)
26. Wilson AA, McCormick P, Kapur S, et al. Radiosynthesis and evaluation of [11C]-(1)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol as a potential radiotracer for in vivo imaging of the dopamine D2 high-affinity state with positron emission tomography. J Med Chem 2005;48(12): 4153-60. (Pubitemid 40800622)
27. Rabiner EA, Slifstein M, Nobrega J, et al. In vivo quantification of regional dopamine-D3 receptor binding potential of (+)-PHNO: studies in nonhuman primates and transgenic mice. Synapse 2009;63(9):782-93.
28. Boileau I, Guttman M, Rusjan P, et al. Decreased binding of the D3 dopamine receptor-preferring ligand [11C]-(1)-PHNO in drug-naive Parkinson's disease. Brain 2009;132(Pt 5):1366-75.
29. Lundkvist C, Sandell J, Någren K, et al. Improved syntheses of the PET radioligands, [11C]FLB 457, [11C]MDL 100907 and [11C]-CIT-FE, by the use of [11C]methyl triflate. J Labelled Comp Radiopharm 1998;41(6):545-56. (Pubitemid 28231441)
30. Någren K, Halldin C, Müller L, et al. Comparison of [11C]methyl triflate and [11C]methyl iodide in the synthesis of PET radioligands such as [11C][beta]-CIT and [11C][beta]-CFT. Nucl Med Biol 1995; 22(8):965-70.
31. Någren K, Müller L, Halldin C, et al. Improved synthesis of some commonly used PET radioligands by the use of [11C]methyl triflate. Nucl Med Biol 1995;22(2):235-9.
32. Mathis CA, Bacskai BJ, Kajdasz ST, et al. A lipophilic thioflavin-T derivative for positron emission tomography (PET) imaging of amyloid in brain. Bioorg Med Chem Lett 2002;12(3):295-8. (Pubitemid 34113887)
33. Mathis CA, Wang Y, Holt DP, et al. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem 2003;46(13):2740-54. (Pubitemid 36702542)
34. Wilson AA, Garcia A, Chestakova A, et al. A rapid one-step radiosynthesis of the beta-amyloid imaging radiotracer N-methyl-[11C]2-(4-methylaminophenyl)- 6-hydroxybenzothiazole ([11C]-6-OHBTA- 1). J Labelled Comp Radiopharm 2004; 47(10):679-82. (Pubitemid 39390042)
35. Solbach C, Uebele M, Reischl G, et al. Efficient radiosynthesis of carbon-11 labelled uncharged thioflavin T derivatives using [11C]methyl triflate for [beta]-amyloid imaging in Alzheimer's disease with PET. Appl Radiat Isot 2005;62(4):591-5. (Pubitemid 40215555)
36. Klunk WE, Engler H, Nordberg A, et al. Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. Ann Neurol 2004;55(3):306-19. (Pubitemid 38269583)
37. Haka MS, Kilbourn MR, Watkins GL, et al. Aryltrimethylammonium trifluoromethanesulfonates as precursors to aryl [18F]fluorides: improved synthesis of [18F]GBR-13119. J Labelled Comp Radiopharm 1989;27(7):823-33. (Pubitemid 19159742)
38. KilbournMR. Fluorine-18 labeling of radiopharmaceuticals. Nuclear science series, vol. NAS-NS-3203. Washington,DC: National Academy Press; 1990. 149.
39. Shiue CY, Fowler JS, Wolf AP, et al. No-carrier-added fluorine-18-labeled N-methylspiroperidol: synthesis and biodistribution in mice. J Nucl Med 1986; 27(2):226-34. (Pubitemid 17024867)
40. Wang GJ, Volkow ND, Logan J, et al. Evaluation of age-related changes in serotonin 5-HT2 and dopamine D2 receptor availability in healthy human subjects. Life Sci 1995;56(14):PL249-53.
41. Ding YS, Gatley SJ, Fowler JS, et al. Mapping nicotinic acetylcholine receptors with PET. Synapse 1996;24(4):403-7. (Pubitemid 26418690)
42. Horti A, Ravert HT, London ED, et al. Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: (+/-)-exo-2-(2-[18F]fluoro-5- pyridyl)-7-azabicyclo[2.2.1]heptane. J Labelled Comp Radiopharm 1996;38(4):355-65.
43. Dolle F, Dolci L, Valette H, et al. Synthesis and nicotinic acetylcholine receptor in vivo binding properties of 2-fluoro-3-[2(S)-2-azetidinylmethoxy] pyridine: a new positron emission tomography ligand for nicotinic receptors. J Med Chem 1999;42(12):2251-9. (Pubitemid 29284245)
44. Ding YS, Liang F, Fowler JS, et al. Synthesis of [18F] norchlorofluoroepibatidine and its N-methyl derivative: new PET ligands for mapping nicotinic acetylcholine receptors. J Labelled Comp Radiopharm 1997;39(10):827-32. (Pubitemid 27395629)
45. Block D, Coenen HH, Stöcklin G. The N.C.A. nucleophilic 18F-fluorination of 1,N-disubstituted alkanes as fluoroalkylation agents. J Labelled Comp Radiopharm 1987;24(9):1029-42. (Pubitemid 18035572)
46. Moerlein SM, Perlmutter JS. Binding of 5-(2′-[18F]fluoroethyl) flumazenil to central benzodiazepine receptors measured in living baboon by positron emission tomography. Eur J Pharmacol 1992;218(1):109-15.
47. Mach RH, Elder ST, Morton TE, et al. The use of [18F]4-fluorobenzyl iodide (FBI) in PET radiotracer synthesis: model alkylation studies and its application in the design of dopamine D1 and D2 receptor-based imaging agents. Nucl Med Biol 1993;20(6):777-94. (Pubitemid 23233472)
48. Hatano K, Ido T, Iwata R. The synthesis of o- and p-[18F]fluorobenzyl bromides and their application to the prepatation of labeled neuroleptics. J Labelled Comp Radiopharm 1991;29(4):373-80.
49. Ravert HT, Madar I, Dannals RF. Radiosynthesis of 3- [18F]fluoropropyl and 4-[18F]fluorobenzyl triarylphosphonium ions. J Labelled Comp Radiopharm 2004;47(8):469-76. (Pubitemid 39062538)
50. Marik J, Sutcliffe JL. Click for PET: rapid preparation of [18F]fluoropeptides using CuI catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett 2006;47(37):6681-4. (Pubitemid 44176106)
51. Glaser M, Arstad E. "Click labeling" with 2-[18f] fluoroethylazide for positron emission tomography. Bioconjug Chem 2007;18(3):989-93. (Pubitemid 47010823)
52. 18F]FPyKYNE, a fluoropyridine-based alkyne reagent designed for the fluorine-18 labelling of macromolecules using click chemistry. J Labelled Comp Radiopharm 2008;51(9):336-42.
53. 18F labeling of bioactive peptides. J Labelled Comp Radiopharm 2008;51(14):444-52.
54. 18F]- fluorobenzene for PET. Bioconjug Chem 2009;20(4):817-23.
55. Glaser M, Robins EG. "Click labelling" in PET radiochemistry. J Labelled Comp Radiopharm 2009; 52(10):407-14.
56. 2. Int J Appl Radiat Isot 1984;35(2):117-22. (Pubitemid 14167501)
57. Chirakal R, Firnau G, Garnett ES. High yield synthesis of 6-[18F]fluoro-L-dopa. J Nucl Med 1986;27(3):417-21.
58. Chirakal R, Schrobilgen GJ, Firnau G, et al. Synthesis of 18F labelled fluoro-m-tyrosine, fluoro-m-tyramine and fluoro-3-hydroxyphenylacetic acid. Int J Rad Appl Instrum A 1991;42(2):113-9.
59. Bergman J, Lehikoinen P, Solin O. Specific radioactivity and radiochemical yield in electrophilic fluorination: case study with [18F]CFT. J Labelled Comp Radiopharm 1997;40(S):38-9.
60. Komar G, Seppanen M, Eskola O, et al. 18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer. J Nucl Med 2008;49(12):1944-51.
61. Bergman J, Solin O. Fluorine-18-labeled fluorine gas for synthesis of tracer molecules. Nucl Med Biol 1997;24(7):677-83. (Pubitemid 27431992)
62. Ametamey SM, Honer M, Schubiger PA. Molecular imaging with PET. Chem Rev 2008;108(5): 1501-16. (Pubitemid 351796395)
63. Hansch C, Leo A, Hoekman D. Exploring QSAR: hydrophobic, electronic, and steric constants. In: Heller SR, editor, In: Computer applications in chemistry books, vol. 2. Washington, DC: American Chemical Society; 1995. p. 348.
64. Nagai Y, Obayashi S, Ando K, et al. Progressive changes of pre- and post-synaptic dopaminergic biomarkers in conscious MPTP-treated cynomolgus monkeys measured by positron emission tomography. Synapse 2007;61(10):809-19. (Pubitemid 47328799)
65. Doudet DJ, Miyake H, Finn RT, et al. 6-18F-L-dopa imaging of the dopamine neostriatal system in normal and clinically normal MPTP-treated rhesus monkeys. Exp Brain Res 1989;78(1):69-80. (Pubitemid 20002455)
66. Shively CA, Grant KA, Ehrenkaufer RL, et al. Social stress, depression, and brain dopamine in female cynomolgus monkeys. Ann N Y Acad Sci 1997; 807:574-7. (Pubitemid 27135545)
67. Nader MA, Czoty PW, Gould RW, et al. Review. Positron emission tomography imaging studies of dopamine receptors in primate models of addiction. Philos Trans R Soc Lond, B, Biol Sci 2008; 363(1507):3223-32.
68. Voytko ML, Mach RH, Gage HD, et al. Cholinergic activity of aged rhesus monkeys revealed by positron emission tomography. Synapse 2001;39(1):95-100.
69. VanBrocklin HF. Radiopharmaceuticals for drug development: United States regulatory perspective current radiopharmaceuticals 2008;1(1):2-6.
70. Ido T, Wan CN, Fowler JS, et al. Fluorination with molecular fluorine. A convenient synthesis of 2-deoxy-2-fluoro-D-glucose. J Org Chem 1977; 42(13):2341-2.
71. Proposed rule (21 CFR Part 212): current good manufacturing practice for positron emission tomography drugs. Fed Regist 2005;70(181):55038-62.
72. Draft guidance on current good manufacturing practice for positron emission tomography drug products; Availability. Fed Regist 2005;70(181):55145.
73. Radiopharmaceuticals for positron emission tomography: compounding. The United States Pharmacopeia and National Formulary USP 32 -NF 27. Rockville (MD): The United States Pharmacopeia Convention, Inc; 2009. Chapter 823.
74. Current good manufacturing practice for positron emission tomography drugs. Fed Regist 2009; 74(236):65409-36.
75. Innovation or stagnation: challenge and opportunity on the critical path to new medical products FDA challenges and opportunities report [internet communication]. March 2004. Available at: http://www.fda.gov/ScienceResearch/ SpecialTopics/CriticalPathInitiative/CriticalPathOpportunitiesReports/ucm077262. htm. Accessed October 4, 2009.
76. FDA guidance for industry, investigators and reviewers: exploratory IND studies [internet communication]. January 2006. Available at. http://www.fda.gov/downloads/Drugs/GuidanceCompliance-RegulatoryInformation/ Guidances/UCM078933.pdf. Accessed October 4, 2009.
77. Position paper on non-clinical safety studies to support clinical trials with a single microdose: CPMP/SWP/ 2599/2502/Rev2591. London (UK): Committee for Medicinal Products for Human Use (CHP), European Medicines Agency; 2004. Available at: www.emea. europa.eu/pdfs/human/swp/259902en.pdf. Accessed October 4, 2009.
78. Residual solvents/organic volatile impurities. The United States Pharmacopeia and National Formulary. USP 32-NF 27. Rockville (MD): The United States Pharmacopeia Convention, Inc; 2009. Chapter 467.
79. Mock BH, Winkle W, Vavrek MT. A color spot test for the detection of Kryptofix 2.2.2 in [18F]FDG preparations. Nucl Med Biol 1997;24(2):193-5. (Pubitemid 27146123)
80. Pharmaceutical compounding-sterile preparations. The United States Pharmacopeia and National Formulary. USP 32-NF 27. Rockville (MD): The United States Pharmacopeia Convention, Inc; 2009. Chapter 797.