Aliphatic nucleophilic radiofluorination

Current Radiopharmaceuticals

Volumn 3, Issue 2, 2010, Pages 81-108

  Roeda, Dirk ^a   Dollé, Frédéric ^a  

^a SERVICE HOSPITALIER FRÉDÉRIC JOLIOT   (France)

Author keywords

Aliphatic nucleophilic radiofluorination; Fluorine 18

Indexed keywords

ACETONITRILE; CESIUM; CLEVUDINE; CRYPTAND 2.2.2; DEUTERIUM; DIMETHYL SULFOXIDE; FLUORINE 18; FLUOROACETIC ACID; FLUORODEOXYGLUCOSE F 18; FLUOROURIDINE; HYDROFLUORIC ACID; N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; NUCLEOPHILE;

ARTICLE; CYCLOTRON; EPIMERIZATION; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEOPHILIC ALIPHATIC RADIOFLUORINATION; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; QUANTUM YIELD; RADIOCHEMISTRY; SOLID PHASE EXTRACTION; STEREOCHEMISTRY;

EID: 77954338537     PISSN: 18744710     EISSN: None     Source Type: Journal    
DOI: 10.2174/1874471011003020081     Document Type: Article

References (171)

1. Dollé, D.; Roeda, D.; Kuhnast, B.; Lasne, M-C. Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals, Tressaud, A., Haufe, G., Ed.; Elsevier: Amsterdam- Boston-Heidelberg-London-New York-Oxford-Paris-San Diego- San Francisco-Singapore-Sydney-Tokyo, 2008, pp. 3-65.
2. Burkart, M.D.; Zhang, Z.Y.; Hung, S.C.; Wong, C.H. A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor. J. Amer. Chem. Soc., 1997, 119, 11743-11746.
3. 18F-labeled 2-deoxy-2-fluoro-D-glucose, 2- deoxy-2-fluoro-D-mannose and 14C-2-deoxy-2-fluoro-D-glucose. J. Label. Compds. Radiopharm., 1978, 14, 175-183.
4. Li, Y.F.; Mao, S.; Hager, M.W.; Becnel, K.D.; Schinazi, R.F.; Liotta, D.C. Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents. Bioorg. Med. Chem. Lett., 2007, 17, 3398-3401.
5. 18F]-FMAU). J. Label. Compds. Radiopharm., 2002, 45, 583-590.
6. Straatmann, M.G.; Welch, M.J. Fluorine-18-labeled diethylaminosulfur trifluoride (DAST): an F for OH fluorinating agent. J. Nucl. Med., 1977, 18, 151-158.
7. 18F-sugar. J. Label. Compds. Radiopharm., 1977, 13, 210.
8. Herdewijn, P.; Vanaerschot, A.; Kerremans, L. Synthesis of nucleosides fluorinated in the sugar moiety - The application of diethylaminosulfur trifluoride to the synthesis of fluorinated nucleosides. Nucleosides Nucleotides, 1989, 8, 65-96.
9. 18F]FLT. Appl. Radiat. Isot., 2007, 65, 1350-1358.
10. Herdewijn, P.; Balzarini, J.; De Clercq, E.; Pauwels, R.; Baba, M.; Broder, S.; Vanderhaeghe, H. 3'-Substituted 2',3'-dideoxynucleoside analogs as potential anti-HIV (HTLV-III/LAV) agents. J. Med. Chem., 1987, 30, 1270-1278.
11. 18F-radiolabeling, as a tracer for the noninvasive monitoring of the biodistribution of drug against AIDS. J. Fluor. Chem., 1991, 55, 283-289.
12. 18F. Int. J. Appl. Radiat. Isot., 1968, 19, 27-32.
13. Clark, J.C.; Goulding, R.W.; Roman, M.; Palmer, A.J. Preparation of fluorine-18-labeled compounds using a recirculatory neon target. Radiochem. Radioanal. Lett., 1973, 14, 101-108.
14. 18F-hydrofluoric acid. Int. J. Appl. Radiat. Isot., 1978, 29, 407-408.
15. 18F-fluorinating intermediates. Int. J. Appl. Radiat. Isot., 1978, 29, 175-183.
16. Helus, F.; Maierborst, W.; Sahm, U.; Wiebe, L.I. F-18 Cyclotron production methods. Radiochem. Radioanal. Lett., 1979, 38, 395-410.
17. Clark, J.C.; Oberdorfer, F. Thermal characteristics of the release of fluorine-18 from an iconel-600 gas target. J. Label. Compds. Radiopharm., 1982, 19, 1337-1339.
18. 18F. J. Label. Compds. Radiopharm., 1982, 19, 1620-1622.
19. Dahl, J.R.; Lee, R.; Bigler, R.E.; Schmall, B.; Aber, J.E. A new target system for the preparation of no-carrier-added 18 F-fluorinating compounds. Int. J. Appl. Radiat. Isot., 1983, 34, 693-700.
20. 18F by deuteron irradiation of a neon-hydrogen gas-target. Radiochim. Acta, 1983, 33, 49-56.
21. 18F process. Appl. Radiat. Isot., 1986, 37, 1135-1139.
22. Abrams, D.N.; Mercer, J.R.; Knaus E.E.; Wiebe, L.I. The synthesis of radiolabeled 1-(2'-fluoro-2'-deoxy-D-ribofuranosyl)uracil and 1-(2'-chloro-2'-deoxy-D-ribofuranosyl)uracil. Int. J. Appl. Radiat. Isot., 1985, 36, 233-238.
23. 18F]fluorouridine as a potential tumor proliferation imaging agent. J. Nucl. Med., 2003, 44, 297P.
24. 18F- fluoride in organic solvents: Production and labeling results. J. Label. Compds. Radiopharm., 1982, 19, 1639-1640.
25. Berridge, M.S.; Crouzel, C.; Comar, D. Aromatic fluorination with n.c.a. F-18 fluoride: a comparative study. J. Label. Compds. Radiopharm., 1985, 22, 687-694.
26. 18F]-labeled 3-deoxy-3- fluoro-D-glucose: synthesis and preliminary biodistribution data. J. Nucl. Med., 1978, 19, 1339-1345.
27. 18F]fluoro-2-deoxy-D-glucose. J. Nucl. Med., 1982, 23, 918-922.
28. Kim, D.W.; Jeong, H.J.; Lim, S.T.; Sohn, M.H.; Katzenellenbogen, J.A.; Chi, D.Y. Facile nucleophilic fluorination reactions using tertalcohols as a reaction medium: significantly enhanced reactivity of alkali metal fluorides and improved selectivity. J. Org. Chem., 2008, 73, 957-962.
29. 18F]fluoride ion. Eur. J. Org. Chem., 2008, 2853-2873.
30. 18F] amine fluorocyanoborane for PET imaging studies. Radiosynthesis and in vivo characterization in rats. Appl. Radiat. Isot., 2007, 65, 204-208.
31. 18F- 21- fluoroprogesterone. Int. J. Appl. Radiat. Isot., 1982, 33, 1449-1452.
32. T.; Fukushi, K.; Ido, T.; Nozaki, T.; Kasida, Y. 8F-Fluorination by crown ether metal fluoride II - Non carrier added labeling method. Int. J. Appl. Radiat. Isot., 1984, 35, 517-520.
33. 18F]N-(2-fluoroethylation) of anilines. J. Label. Compds. Radiopharm., 2004, 47, 217-232.
34. 18F-labeled ligand for PET imaging of brain peripheral benzodiazepine receptors. J. Label. Compds. Radiopharm., 2005, 48 (Suppl. 1), S4.
35. 18F-labelled derivatives of indiplon as potential GABA(A) receptor imaging tracers for PET. J. Label. Compds. Radiopharm., 2008, 51, 123-131.
36. 18F-labeled ligand for imaging brain peripheral benzodiazepine receptors with PET. J. Med. Chem., 2009, 52, 688-699.
37. 18F]-fluoroheptadecanoic acid in high yield via aminopolyether supported nucleophilic fluorination. J. Label. Compds. Radiopharm., 1986, 23, 455-466.
38. 18F]-fluoro-2-deoxy-D-glucose using aminopolyether supported nucleophilic substitution. J. Nucl. Med., 1986, 27, 235-238.
39. 18F]fluoride. Appl. Radiat. Isot., 1988, 39, 699-703.
40. Kornguth, M.L.; DeGrado, T.R.; Holden, J.E.; Gatley, S.J. Effects of reaction conditions on rates of incorporation of no-carrier added F-18 fluoride into several organic compounds. J. Label. Compds. Radiopharm., 1988, 25, 369-381.
41. 18F]fluoropropyl thymidine. Nucl. Med. Biol., 2008, 35, 697-705.
42. 18F]-4-[5-(4- methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene sul- fonamide as a PET imaging probe for COX-2 expression. Bioorg. Med. Chem., 2007, 15, 1802-1807.
43. 18F]fluoride from [18O]water using anion exchange resin. Appl. Radiat. Isot., 1990, 41, 531-533.
44. 18F]2-fluoro-2-deoxy-D-glucose. Appl. Radiat. Isot., 1986, 37, 397-401.
45. Tewson, T.J.; Berridge, M.S.; Bolomey, L.; Gould, K.L. Routine production of reactive fluorine-18 fluoride salts from an oxygen- 18-water target. Nucl. Med. Biol., 1988, 15, 499-504.
46. 18F]fluoride production. Appl. Radiat. Isot., 1999, 50, 699-705.
47. 18F]FDG synthesis. Appl. Radiat. Isot., 2006, 64, 298-305.
48. Avila-Rodriguez, M.A.; Wilson, J.S.; McQuarrie, S.A. A quantitative and comparative study of radionuclidic and chemical impurities in water samples irradiated in a niobium target with Havar vs. niobium-sputtered Havar as entrance foils. Appl. Radiat. Isot., 2008, 66, 1775-1780.
49. 18F]FDG synthesis process. Appl. Radiat. Isot., 2009, 67, 248-255.
50. Katsifis, A.; Hamacher, K.; Schnitter, J.; Stöcklin, G. Optimization studies concerning the direct nucleophilic fluorination of butyrophenone neuroleptics. Appl. Radiat. Isot., 1993, 44, 1015-1020.
51. 18F]Fluoride ion: a versatile reagent for radiopharmaceutical syntheses. J. Label. Compds. Radiopharm., 1986, 23, 1174-1176.
52. 18F]fluoride from irradiated 18O-water and subsequent no carrier added nucleophilic fluorination. Appl. Radiat. Isot., 2002, 56, 519-523.
53. Kiesewetter, D.O.; Jagoda, E.M.; Starrett, J.E.; Gribkoff, V.K.; Hewawasam, P.; Srinivas, N.; Salazar, D.; Eckelman, W.C. Radiochemical synthesis and biodistribution of a novel maxi-K potassium channel opener. Nucl. Med. Biol., 2002, 29, 55-59.
54. 18F-labeled MaxiPost (TM). An agent for post-stroke neuroprotection. J. Label. Compds. Radiopharm., 2003, 46, 1161-1171.
55. 18F]-FMXU) for PET. J. Label. Compds. Radiopharm., 2005, 48, 941-950.
56. 18F]-fluoro-arabinonucleosides. J. Fluor. Chem., 2000, 106, 87-91.
57. 18F]-labeled nucleosides. Synth. Commun., 2002, 32, 1757-1764.
58. 18F]fluoro-1-D-arabinofuranosyluracil and its 5- substituted nucleosides. J. Label. Compds. Radiopharm., 2003, 46, 285-289.
59. 18F]FIAU, as potential PET agents for imaging cellular proliferation. Nucl. Med. Biol., 2003; 30, 215-224.
60. Bading, J.R.; Shahinian, A.H.; Vail, A.; Bathija, P.; Koszalka, G.W.; Koda, R.T.; Alauddin, M.M.; Fissekis, J.D.; Conti, P.S. Pharmacokinetics of the thymidine analog 2'-fluoro-5-methyl-1-D-arabinofuranosyluracil (FMAU) in tumor-bearing rats. Nucl. Med. Biol., 2004, 31, 407-418.
61. Shields, A.F.; Grierson, J.R.; Kozawa, S.M.; Zheng, M. Development of labeled thymidine analogs for imaging tumor proliferation. Nucl. Med. Biol., 1996, 23, 17-22.
62. 18F]fluorouridine via a new nosylate precursor. J. Label. Compds. Radiopharm., 2006, 49, 1237-1246.
63. Peng, C.G.; Damha, M.J. Probing DNA polymerase activity with stereoisomeric 2'-fluoro-D-arabinose (2'F-araNTPs) and 2'- fluoro-D-ribose (2'F-rNTPs) nucleoside 5-triphosphates. Can. J. Chem., 2008, 86, 881-891.
64. 18F]fluoropropyl)-2,3-dimethoxybenzamide as an improved dopamine D-2 receptor tracer. Nucl. Med. Biol., 1995, 22, 283-296.
65. 18F]DPA-714, a selective radioligand for imaging the translocator protein (18 kDa) with PET. J. Label. Compds. Radiopharm., 2008, 51, 286-292.
66. 18F]fluoroethyl)-L-tyrosine. Appl. Radiat. Isot., 2002, 57, 853-856.
67. Zeng, F.; Jarkas, N.; Stehouwer, J.S.; Voll, R.J.; Owens, M.J.; Kilts, C.D.; Nemeroff, C.B.; Goodman, M.M. Synthesis, in vitro characterization, and radiolabeling of reboxetine analogs as potential PET radioligands for imaging the norepinephrine transporter. Bioorg. Med. Chem., 2008, 16, 783-793.
68. 18F]LBT-999, a selective radioligand for the visualization of the dopamine transporter with PET. J. Label. Compds. Radiopharm., 2006, 49, 687-698.
69. 18F]LBT-999: a selective radioligand for the visualization of the dopamine transporter with PET. J. Label. Compds. Radiopharm., 2007, 50, 716-723.
70. 18F-FECNT from mesylate precursor. Appl. Radiat. Isot., 2008, 66, 1881-1885.
71. 18F]Fluoroalkyl agents: synthesis, reactivity and application for development of PET ligands in molecular imaging. Curr. Topics Med. Chem., 2007, 7, 1817-1828.
72. 18F]fluoroalkyl pyrimidine nucleosides for molecular imaging of herpes simplex virus type 1 thymidine kinase reporter gene expression. J. Med. Chem., 2008, 51, 5690-5701.
73. 18F]Fluoroalkyl pyrimidine nucleosides: probes for positron emission tomography imaging of herpes simplex virus type 1 thymidine kinase gene expression. Nucl. Med. Biol., 2009, 36, 29-38.
74. 18F]fluoroethyl-1-D-arabinofuranosyl uracil. Nucl. Med. Biol., 2005, 32, 811-819.
75. 18F]FFEAU, and other imaging probes. J. Nucl. Med., 2008, 49, 637-648.
76. 18F]fluoroethyl)-thymidine. Nucl. Med. Biol., 2006, 33, 765-772.
77. 18F]- FPT) for PET. J. Label. Compds. Radiopharm., 2006, 49, 1079-1088.
78. 18F]-FMPPT) for PET. J. Label. Compds. Radiopharm., 2007, 50, 1185-1191.
79. Yu, C.S.; Eisenbarth, J.; Runz, A.; Weber, K.; Zeisler, S.; Oberdorfer, F. Syntheses of 5-(2-radiohaloethyl)- and 5-(2-radiohalovinyl)- 2'-deoxyuridines. Novel types of radiotracer for monitoring cancer gene therapy with PET. J. Label. Compds. Radiopharm., 2003, 46, 421-439.
80. 18F]fluoromethyl)phenyl isothiocyanate and its use in labelling oligonucleotides. Acta Chem. Scand., 1997, 51, 1236-1240.
81. Ghosh, P.; Pal, A.; Shavrin, A.; Bornmann, W.; Gelovani, J.G.; Alauddin, M.M. Synthesis of N3-substituted thymidine analogues for measurement of cellular kinase activity. Med. Chem., 2008, 4, 503-512.
82. Lang, L.X.; Jagoda, E.; Ma, Y.; Sassaman, M.B.; Eckelman, W.C. Synthesis and in vivo biodistribution of F-18 labeled 3-cis-, 3- trans-, 4-cis-, and 4-trans-fluorocyclohexane derivatives of WAY 100635. Bioorg. Med. Chem., 2006, 14, 3737-3748.
83. 18F-radiolabelling and biological evaluations of C-6 alkylated pyrimidine nucleoside analogues. Nucleosides Nucleotides Nucleic Acids, 2004, 23, 1707-1721.
84. van Dort, M.E.; Jung, Y.W.; Sherman, P.S.; Kilbourn, M.R.; Wieland, D.M. Fluorine for hydroxy substitution in biogenic amines: asymmetric synthesis and biological evaluation of fluorine-18- labeled -fluorophenylalkylamines as model systems. J. Med. Chem., 1995, 38, 810-815.
85. 18F-fluoroclorgyline) as a potential PET radiotracer for monoamine oxidase-A. Nucl. Med. Biol., 1999, 26, 619-625.
86. 18F]fluoropropyl amines. J. Label. Compds. Radiopharm., 2004, 47, 953-969.
87. 18F]fluoro- L-ascorbic acid. Appl. Radiat. Isot., 1992, 43, 633-639.
88. 18F]fluoro-2-methyl-2-(methylamino) propanoic acid. J. Med. Chem., 2002, 45, 2240-2249.
89. Tewson, T.J. Synthesis of no-carrier-added fluorine-18 2-fluoro-2- deoxy-D-glucose. J. Nucl. Med., 1983, 24, 718-721.
90. Tewson, T.J. Cyclic sulfur esters as substrates for nucleophilic substitution. A new synthesis of 2-deoxy-2-fluoro-D-glucose. J. Org. Chem., 1983; 48, 3507-3510.
91. Zeitouni, J.; Norsikian, S.; Merlet, D.; Lubineau, A. Synthesis of C- glycosides and C-disaccharides using Mukaiyama aldol reaction in aqueous media. Adv. Synth. Cat. 2006, 348, 1662-1670.
92. Zhang, L.J.; Zhang, W.; Liu, J.; Hu, J.B. C-F Bond cleavage by intramolecular SN2 reaction of alkyl fluorides with O- and N- nucleophiles. J. Org. Chem., 2009, 74, 2850-2853.
93. Lim, J.L.; Zheng, L.; Berridge, M.S.; Tewson, T.J. The use of 3- methoxymethyl-16β-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-18 16 -fluoroestradiol. Nucl. Med. Biol., 1996, 23, 911-915.
94. 18F-labeled difluoroestradiols: preparation and preclinical evaluation as estrogen receptor-binding radiopharmaceuticals. Steroids, 2002, 67, 765-775.
95. 18F]fluorine substitution at the 16 -position of fulvestrant. Nucl. Med. Biol., 2004, 31, 691-698.
96. 18F -labelling of Aring substituted 16 -fluoro-estradiols as potential radiopharmaceuticals for PET imaging. Steroids, 2009, 74, 42-50.
97. Kiesewetter, D.O.; Katzenellenbogen, J.A.; Kilbourn, M.R.; Welch, M.J. Synthesis of 16-fluoroestrogens by unusually facile fluorideion displacement-reactions: prospects for the preparation of fluorine-18 labeled estrogens. J. Org. Chem., 1984, 49, 4900-4905.
98. Kiesewetter, D.O.; Kilbourn, M.R.; Welch, M.J. Preparation of four fluorine-18-labeled oestrogens and their selectives uptakes in target tissues of immature rats. J. Nucl. Med., 1984, 25, 1212-1221.
99. 18F]fluoroethylation approaches from ethylene cyclic sulfate. J. Label. Compds. Radiopharm., 1999, 42 (Suppl. 1), S318-S320.
100. Tewson, T.J.; Welch, M.J. Preparation and preliminary biodistribution of no carrier added fluorine-18 fluoroethanol. J. Nucl. Med., 1980, 21, 559-564.
101. 18F-labelled 2-fluoroethyl-nitrosoureas. Can. J. Chem., 1984, 42, 2107-2112.
102. 18F]fluorophenylalanine. J. Label. Compds. Radiopharm., 1995, 37, 133-134.
103. Gillings, N.M.; Gee, A.D. Aziridines in the synthesis of 11C and 18 F-labelled amino acids. J. Label. Compds. Radiopharm., 1997, 40, 764-765.
104. 18F]fluoroethyl)- carboxamidoadenosine: a promising tracer for investigation of adenosine receptor system by PET technique. J. Label. Compds. Radiopharm., 2000, 43, 807-815.
105. 18F]-fluoride. Tetrahedron Lett., 2009, 50, 544-547.
106. 18F]fluoroprogesterone: a first step towards a potential receptor-ligand for PET. Appl. Radiat. Isot., 1994, 45, 811-813.
107. 18F]FLT). J. Radioanal. Nucl. Chem., 2000, 243, 843-846.
108. 18F]fluoro-thymidine with 2,3'-anhydro-5'-O-(4,4'-dimethoxytrityl)thymidine. J. Label. Compds. Radiopharm., 2000, 43, 1211-1218.
109. 18F]FLT) and the fate of the precursor, 2,3'-anhydro-5'-O-(4,4'- dimethoxytrityl)-thymidine. J. Label. Compds. Radiopharm., 2001, 44 (Suppl. 1), S871-S873.
110. 18F]FLT preparation. J. Radioanal. Nucl. Chem., 2002, 251, 55-58.
111. 18F]fluorothymidine using three precursors. Appl. Radiat. Isot., 2006, 64, 187-193.
112. Tewson, T.; Paulsen, A.; el-Shafie F. Production of F-18 fluorothymidine: substrates and yields. J. Label. Compds. Radiopharm., 2003, 46, S222.
113. 18F]FLT) and simple method for a metabolite analysis in plasma. Radiochim. Acta, 2006, 94, 447-451.
114. Grierson, J.R.; Shields, A.F.; Eary, J.F. Development of a radiosynthesis for 3'-[F-18]fluoro-3'-deoxynucleosides. J. Label. Compds. Radiopharm., 1997, 40, 60-62.
115. 18F]fluorothymidine using (5'-O-dimethoxytrityl-2'-deoxy-3'-O-nosyl-D-threo pentofuranosyl)thymine and its 3-N-BOC-protected analogue as a labeling precursor. Nucl. Med. Biol., 2003, 30, 151-157.
116. Krizmanic, I.; Visnjevac, A.; Luic, M.; Glavas-Obrovac, L.; Zinic, M.; Zinic, B. Synthesis, structure, and biological evaluation of C-2 sulfonamido pyrimidine nucleosides. Tetrahedron, 2003, 59, 4047-4057.
117. 18F]FLT: syntheses and radiofluorination trials. Nucl. Med. Biol., 2008, 35, 413-423.
118. Grierson, J.R.; Shields, A.F. Optimizing labeling substrate structure for 3'-deoxy-3'-[F-18]fluorothymidine: [F-18]FLT. J. Nucl. Med., 1999, 40, 83P.
119. 18F]FLT for imaging of cellular proliferation in vivo. Nucl. Med. Biol., 2000, 27, 143-156.
120. 18F]fluoroacetate. J. Label. Compds. Radiopharm., 1997, 39, 395-399.
121. 18F]fluoroacetate a simple and fast method using a commercial synthesizer. Nucl. Med. Biol., 2006, 33, 153-158.
122. 18F]fluoroacetate and radiopharmacological characterization in rats and tumorxenografted mice. Curr. Radiopharm., 2008, 1, 103-109.
123. 18F]fluoride. Appl. Radiat. Isot., 1986, 37, 305-308.
124. 18F]fluoroacetyl-D-glucosamine), potential diagnostic imaging agent. J. Label. Compds. Radiopharm. 1989, 27, 1317-1324.
125. 18F]fluoroacetate. J. Label. Compds. Radiopharm., 2008, 51, 297-301.
126. 18F-for-19F exchange. J. Label. Compds. Radiopharm., 1990, 28, 1355-1361.
127. 18F on superconjugate system. J. Label. Compds. Radiopharm., 1979, 16, 153-154.
128. 18F]fluoride ion: Nucleophilic fluorination as the detagging process. Angew. Chem. Int. Ed. Engl., 2009, 48, 586-589.
129. Zhang, W. Fluorous linker-facilitated chemical synthesis. Chem. Rev., 2009, 109, 749-795.
130. 18F]fluoro-L- proline, radiotracers for PET-investigation of disordered matrix protein synthesis. J. Label. Compds. Radiopharm., 1999, 42, 1135-1144.
131. 18F]fluoro-L-proline. J. Label. Compds. Radiopharm., 2000, 43, 1047-1058.
132. Grierson, J.R.; Link, J.M.; Mathis, C.A.; Rasey, J.S.; Krohn, K.A. A radiosynthesis of fluorine-18 fluoromisonidazole. J. Nucl. Med., 1989, 30, 343-350.
133. Kämäräinen, E.L.; Kyllönen, T.; Nihtilä, O.; Björk, H.; Solin, O. Preparation of fluorine-18-labelled fluoromisonidazole using two different synthesis methods. J. Label. Compds. Radiopharm., 2004, 47, 37-45.
134. 18F]fluoromisonidazole. Nucl. Med. Biol., 2005, 32, 553-558.
135. 18F]fluoroethylcholine as a radiotracer for cancer imaging. Bioorg. Med. Chem., 2007, 15, 3171-3175.
136. 18F]fluoroethylcholine for prostate cancer imaging. Bioorg. Med. Chem., 2008, 16, 9121-9126.
137. 18F]2-fluoro-2-deoxy-D-glucose. Angew. Chem. Int. Ed. Engl., 2007, 46, 941-944.
138. 18F]-2-fluoro-2-deoxy-D-glucose from resinbound perfluoroalkylsulfonates. Org. Biomol. Chem., 2009, 7, 564-575.
139. 18F]-FCAU), and their biological evaluation as markers for gene expression. Nucl. Med. Biol., 2004, 31, 399-405.
140. 18F]FMAU). Bull. Kor. Chem. Soc., 2007, 28, 2449-2453.
141. 18F]-L-FMAU) for PET. Appl. Radiat. Isot., 2007, 65, 941-6.
142. 18F]FEAU: a novel PET imaging agent for HSV1- tk/sr39tk reporter gene expression. Mol. Imag. Biol., 2008, 10, 82-91.
143. Kilbourn, M.R.; Pavia, M.; Gregor, V. Synthesis of fluorine-18 labeled GABA uptake inhibitors. Appl. Radiat. Isot., 1990, 41, 823-828.
144. 18F]-(S)-fluoxetine: a selective serotonine uptake inhibitor. J. Label. Compds. Radiopharm., 1993, 33, 703-710.
145. 18F-labelled alkylating agent 2,2,2-trifluoroethyl triflate: synthesis and specific activity. J. Label. Compds. Radiopharm., 1995, 36, 537-547.
146. 18F-labeled polyfluorinated ethyl groups. Appl. Radiat. Isot., 1996, 47, 401-407.
147. 18F]trifluoromethyl bromide. J. Label. Compds. Radiopharm., 2003, 46 (Suppl. 1), S219.
148. 18F]fluoro-compounds for PET studies from bromo-compounds. Appl. Radiat. Isot., 2003, 58, 557-566.
149. 18F-fluoro-D-glucose. Appl. Radiat. Isot., 1995, 46, 149-155.
150. 18F]FLT. Nucl. Med. Biol., 2002, 29, 263-273.
151. 18F]fluorothymidine. Nucl. Med. Biol., 2004, 31, 803-809.
152. 18F]-FLT) for positron emission tomography imaging. J. Pharm. Biomed. Anal., 2007, 45, 154-157.
153. Kim, D.W.; Ahn, D.S.; Oh, Y.H.; Lee, S.; Kil, H.S.; Oh, S.J.; Lee, S.J.; Kim, J.S.; Ryu, J.S.; Moon, D.H.; Chi, D.Y. A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules. J. Am. Chem. Soc., 2006, 128, 16394-16397.
154. 18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent. Eur. J. Nucl. Med. Mol. Imaging, 2007, 34, 1406-1409.
155. 18F]fluorothymidine by nucleophilic fluorination in various alcohol solvents. J. Label. Compds. Radiopharm., 2008, 51, 80-82.
156. 18F]N-3-fluoropropyl-2-carbomethoxy-3- -(4-iodophenyl)nortropane and the first human study with positron emission tomography. Nucl. Med. Biol., 1996, 23, 999-1004.
157. Kim, D.W.; Song, C.E.; Chi, D.Y. New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity. J. Amer. Chem. Soc., 2002, 124, 10278-10279.
158. Kim, D.W.; Choe, Y.S.; Chi, D.Y. A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: reaction in ionic liquids shows tolerance for water. Nucl. Med. Biol., 2003, 30, 345-350.
159. 18F]fluorination. J. Label. Compds. Radiopharm., 2003, 46 (Suppl. 1), S89.
160. 18F]FDG without an evaporation step using an ionic liquid. Appl. Radiat. Isot., 2004, 61, 1241-1246.
161. 18F]FLT) in ionic liquid, [bmim][OTf]. J. Label. Compds. Radiopharm., 2006, 49, 287-293.
162. Shinde, S.S.; Lee, Y.S.; Chi, D.Y. Synergistic effect of two solvents, tert-alcohol and ionic liquid, in one molecule in nucleophilic fluorination. Org. Lett., 2008, 10, 733-735.
163. O'Hagan, D.; Schaffrath, C.; Cobb, S.L.; Hamilton, J.T.G.; Murphy C.D. Biosynthesis of an organofluorine molecule. Nature, 2002, 416, 279.
164. Zhu, X.F.; Robinson, D.A.; McEwan, A.R.; O'Hagan, D.; Naismith, J.H. Mechanism of enzymatic fluorination in Streptomyces cattleya. J. Amer. Chem. Soc., 2007, 129, 14597-14604.
165. 18F]-fluoro-5'-deoxyadenosine for imaging with PET. J. Label. Compds. Radiopharm., 2003, 46, 1181-1189.
166. 18F bond formation, an enzymatic tool for PET labelling. Chem. Comm., 2006, 652-654.
167. O'Hagan, D. Recent developments on the fluorinase from Streptomyces cattleya. J. Fluor. Chem., 2006, 127, 1479-1483.
168. 18F]fluoro-adenosine by radiofluorination of 5'-deoxy-5'-haloadenosine derivatives. J. Radioanal. Nucl. Chem., 2000, 245, 399-401.
169. 18F]fluoride-ion on the series of N6- benzoyl-2',3'-isopropylideneadenosine-5'-sulfonates. J. Radioanal. Nucl. Chem., 2002, 251, 413-416.
170. 18F]-5'-deoxy-5'- fluorouridines. Angew. Chem. Int. Engl., 2008, 47, 10141-10143.
171. Deng, H.; Cross, S.M.; McGlinchey, R.P.; Hamilton, J.T.G.; O'Hagan, D. In vitro reconstituted biotransformation of 4- fluorothreonine from fluoride ion: application of the fluorinase. Chem. Biol., 2008, 15, 1268-1276.