Automated synthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-β-d-arabin ofuranosyluracil ([18F]-FMAU) using a one reactor radiosynthesis module

Nuclear Medicine and Biology

Volumn 38, Issue 2, 2011, Pages 201-206

  Li, Zibo ^a   Cai, Hancheng ^a   Conti, Peter S ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

18F FMAU; Automated synthesis; F 18 labeling; Friedel Crafts catalysts; PET probe

Indexed keywords

ACETONITRILE; ALCOHOL; CLEVUDINE F 18; PHOSPHATE; RADIOISOTOPE; UNCLASSIFIED DRUG; WATER;

ARTICLE; AUTOMATION; CELL PROLIFERATION; DRUG PURIFICATION; DRUG PURITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RADIOCHEMISTRY; REACTION TIME; REACTOR;

ARABINOFURANOSYLURACIL; AUTOMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; IODINE RADIOISOTOPES; RADIOCHEMISTRY;

EID: 79651471152     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.08.010     Document Type: Article

References (37)

1. 18F]FLT. Eur J Nucl Med Mol Imaging 2008, 35:990-998.
2. Conti P.S., Bading J.R., Mouton P.P., Links J.M., Alauddin M.M., Fissekis J.D., et al. In vivo measurement of cell proliferation in canine brain tumor using C-11-labeled FMAU and PET. Nucl Med Biol 2008, 35:131-141.
3. 18F-Fluoro-1-beta-d-arabinofuranosyl)-5-bromou racil: PET imaging studies in dogs. J Nucl Med 2005, 46:1916-1922.
4. 18F-FMAU and PET. J Nucl Med 2005, 46:292-296.
5. 18F-fluoro-beta-d-arabinofuranosyl)thymine and PET. J Nucl Med 2007, 48:1436-1441.
6. Bading J.R., Shahinian A.H., Vail A., Bathija P., Koszalka G.W., Koda R.T., et al. Pharmacokinetics of the thymidine analog 2'-fluoro-5-methyl-1-beta-d-arabinofuranosyluracil (FMAU) in tumor-bearing rats. Nucl Med Biol 2004, 31:407-418.
7. 18F]-FCAU), and their biological evaluation as markers for gene expression. Nucl Med Biol 2004, 31:399-405.
8. 18F-fluoro-5-fluoro-1-beta-d-arabinofuranosylurac il as a potential PET imaging agent for suicide gene expression. J Nucl Med 2004, 45:2063-2069.
9. Hajitou A., Trepel M., Lilley C.E., Soghomonyan S., Alauddin M.M., Marini F.C., et al. A hybrid vector for ligand-directed tumor targeting and molecular imaging. Cell 2006, 125:385-398.
10. Najjar A.M., Nishii R., Maxwell D.S., Volgin A., Mukhopadhyay U., Bornmann W.G., et al. Molecular-genetic PET imaging using an HSV1-tk mutant reporter gene with enhanced specificity to acycloguanosine nucleoside analogs. J Nucl Med 2009, 50:409-416.
11. 18F]FFEAU, and other imaging probes. J Nucl Med 2008, 49:637-648.
12. Bading J.R., Shields A.F. Imaging of cell proliferation: status and prospects. J Nucl Med 2008, 49(Suppl 2):64S-80S.
13. 18F]FMAU and positron emission tomography in patients with cancer. Eur J Nucl Med Molec Imaging 2005, 32:15-22.
14. Schwartz J.L., Tamura Y., Jordan R., Grierson J.R., Krohn K.A. Monitoring tumor cell proliferation by targeting DNA synthetic processes with thymidine and thymidine analogs. J Nucl Med 2003, 44:2027-2032.
15. Grierson J.R., Schwartz J.L., Muzi M., Jordan R., Krohn K.A. Metabolism of 3'-deoxy-3'-[F-18]fluorothymidine in proliferating A549 cells: validations for positron emission tomography. Nucl Med Biol 2004, 31:829-837.
16. Kong X.B., Zhu Q.Y., Vidal P.M., Watanabe K.A., Polsky B., Armstrong D., et al. Comparisons of anti-human immunodeficiency virus activities, cellular transport, and plasma and intracellular pharmacokinetics of 3'-fluoro-3'-deoxythymidine and 3'-azido-3'-deoxythymidine. Antimicrob Agents Chemother 1992, 36:808-818.
17. 18F]-FLT) as positron emission tomography tracer for imaging proliferation in a murine B-cell lymphoma model and in the human disease. Cancer Res 2003, 63:2681-2687.
18. 76Br-BFU as proliferation markers. J Nucl Med 2002, 43:1688-1698.
19. 18F]FLT. Eur J Nucl Med Molec Imaging 2008, 35:990-998.
20. 11C-FMAU): Comparison Studies with FDG. Radiological Society of North America (RSNA) 2002, T16-1657, Dec. 5-9, Chicago, IL.
21. Horn D.M., Neeb L.A., Colacino J.M., Richardson F.C. Fialuridine is phosphorylated and inhibits DNA synthesis in isolated rat hepatic mitochondria. Antiviral Res 1997, 34:71-74.
22. Colacino J.M. Mechanisms for the anti-hepatitis B virus activity and mitochondrial toxicity of fialuridine (FIAU). Antiviral Res 1996, 29:125-139.
23. Fu D.X., Tanhehco Y., Chen J., Foss C.A., Fox J.J., Chong J.M., et al. Bortezomib-induced enzyme-targeted radiation therapy in herpesvirus-associated tumors. Nat Med 2008, 14:1118-1122.
24. Fu D.X., Tanhehco Y.C., Chen J., Foss C.A., Fox J.J., Lemas V., et al. Virus-associated tumor imaging by induction of viral gene expression. Clin Cancer Res 2007, 13:1453-1458.
25. Watanabe K.A., Reichman U., Hirota K., Lopez C., Fox J.J. Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. J Med Chem 1979, 22:21-24.
26. Chu C.K., Ma T., Shanmuganathan K., Wang C., Xiang Y., Pai S.B., et al. Use of 2'-fluoro-5-methyl-beta-l-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus. Antimicrob Agents Chemother 1995, 39:979-981.
27. Watanabe K.A., Su T.L., Reichman U., Greenberg N., Lopez C., Fox J.J. Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)uracils. J Med Chem 1984, 27:91-94.
28. 11C]-FMAU): a potential nucleoside analog for in vivo study of cellular proliferation with PET. Nucl Med Biol 1995, 22:783-789.
29. 18F]-FMAU). J Labelled Comp Radiopharm 2002, 45:583-590.
30. 18F]fluoro-1-'-d-arabinofuranosyluracil and its 5-substituted nucleosides. J Labelled Comp Radiopharm 2003, 46:285-289.
31. 18F]labelled FAU, FMAU, FBAU, FIAU. Nucl Med Biol 2003, 30:215-224.
32. 18F]FEAU: a novel PET imaging agent for HSV1-tk/sr39tk reporter gene expression. Mol Imaging Biol 2008, 10:82-91.
33. 18F]-FMAU using a novel dual reactor radiosynthesis module. J Labelled Comp Radiopharm 2009, 52:553-558.
34. 18F]FEAU. Nat Protoc 2007, 2:416-423.
35. Rasey J.S., Grierson J.R., Wiens L.W., Kolb P.D., Schwartz J.L. Validation of FLT uptake as a measure of thymidine kinase-1 activity in A549 carcinoma cells. J Nucl Med 2002, 43:1210-1217.
36. 18F-FMAU). J Nucl Med 2010, 51(Supplement 2):533.
37. 18F-FMAU). 240th American Chemical Society (ACS) National Meeting & Exposition August 22-26, 2010 2010, Abstract # 19729, Boston, Massachusetts.