Radiosynthesis of 2'-deoxy-2'-[18f]fluorothymidine ([18f]ft), a putative pet agent for imaging HSV-TK expression

Current Radiopharmaceuticals

Volumn 2, Issue 1, 2009, Pages 75-82

  Sun, William ^a,b   Wilson, John ^b   Kumar, Piyush ^b   Knaus, Edward ^a   Wiebe, Leonard ^a,b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b CROSS CANCER INSTITUTE   (Canada)

Author keywords

( 18f ft); 2' deoxy 2' 18f fluorothymidine; 18f radiofluorination; Fluorodeoxythymidine; Herpes simplex thymidine kinase; HSV TK; Transgene imaging

Indexed keywords

2' DEOXY 2 FLUOROTHYMIDINE F 18; THYMIDINE KINASE; TRACER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; DRUG PURIFICATION; DRUG SYNTHESIS; FLUORINATION; GENE EXPRESSION; HERPES SIMPLEX VIRUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; POSITRON EMISSION TOMOGRAPHY; PRECURSOR; PRIORITY JOURNAL; REACTION TIME; REPORTER GENE;

EID: 77953770573     PISSN: 18744710     EISSN: None     Source Type: Journal    
DOI: 10.2174/1874471010902010075     Document Type: Article

References (49)

1. Prusoff, W.H.; Holmes, W.L.; Welch, A.D. Non-utilization of radioactive iodinated uracil, uridine, and orotic acid by animal tissues in vivo. Cancer Res., 1953, 13, 221-6.
2. Prusoff, W.H. Synthesis and biological activities of iododeoxyuridine, an analog of thymidine. Biochim. Biophys. Acta, 1959, 32, 295-6.
3. Prusoff, W.H.; Jaffee, J.J.; Guenther, H. Studies in the mouse of the pharmacology of 5-iododeoxyuridine, an analogue of thymidine. Biochem. Pharmacol., 1960, 3, 110-21.
4. Duschinsky, R.T.; Pleven, E.; Heidelberger, C. The Synthesis of 5-fluoropyrimidines. J. Am. Chem. Soc., 1957, 79, 4559-62.
5. 18F-5-fluorouracil. J. Nucl. Med., 1973, 14, 63-4.
6. Heidelberger, C.; Chaudhuri, N. K.; Danneberg, P.; Mooren, D.; Griesbach, L.; Duschinsky, R.; Schnitzer, R.J.; Pleven, E.; Scheiner, J. Fluorinated pyrimidines, a new class of tumour-inhibitory compounds. Nature, 1957, 179, 663-6.
7. 18F-5-Fluoro-2'-deoxyuridine as a radiopharmaceutical for diagnostic oncology. In: The Chemistry of Radiopharmaceuticals; Heindel, N.N.; Burns, H.D.; Honda, T.; Brady, LW, Eds.; Masson Publishing USA, Inc., NY, 1977; 205-13.
8. Wiebe, L.I. Applications of nucleoside-based molecular probes for the in vivo assessment of tumour biochemistry using positron emission tomography (PET). Brazilian Arch. Biol. Technol., 2007, 50, 445-59.
9. Elion, G.B. The chemotherapeutic exploitation of virus-specified enzymes. Adv. Enzyme Regul., 1980, 18, 53-66.
10. Samuel, J. Radiohalogenated pyrimidine nucleosides as potential non-invasive diagnostic agents for Herpes simplex encephalitis. PhD Thesis, University of Alberta, Edmonton, Canada, 1985.
11. Moolten, F.L. Tumor chemosensitivity conferred by inserted herpes thymidine kinase genes: paradigm for a prospective cancer control strategy. Cancer Res., 1986, 46, 5276-81.
12. Knaus, E.E.; Wiebe, L.I.; Morin, K.W. Combined use of nucleoside analogues and gene transfection for tissue imaging and therapy. UK Priority Patent: 1994:10:21. Canadian Patent 2,202,891 issued 1997.07.16.
13. Balzarini, J.; Morin, K.W.; Knaus, E.E.; Wiebe, L.I.; De Clercq, E. Novel (E)-5-(2-iodovinyl)-2'-deoxyuridine derivatives as potential cytostatic agents against herpes simplex virus thymidine kinase gene transfected tumors. Gene Ther., 1995, 2, 317-22.
14. Tjuvajev, J.G.; Stockhammer, G.; Desai, R.; Uehara, H.; Watanabe, K.; Gansbacher, B.; Blasberg, R.G. Imaging the expression of transfected genes in vivo. Cancer Res., 1995, 55, 6126-32.
15. Rome, C.; Couillaud, F.; Moonen, C.T. Gene expression and gene therapy imaging. Eur. Radiol., 2007, 17, 305-19.
16. Peñuelas, I.; Haberkorn, U.; Yaghoubi, S.; Gambhir, S.S. Gene therapy imaging in patients for oncological applications. Eur. J. Nucl. Med. Mol. Imaging, 2005, 32 (Suppl 2), S384-403.
17. Couturier, O.; Chatal, J.F.; Hustinx, R. Fluorinated analogs of nucleosides and fluorinated tracers of gene expression for positron emission tomography. Bull. Cancer, 2004, 91, 695-703.
18. Wiebe, L.I.; Knaus, E.E. Nucleosides in gene therapy imaging. Curr. Pharmaceut. Des., 2001, 7, 1893-906.
19. 18F]FEAU) as markers for suicide gene expression. Eur. J. Nucl. Med. Mol. Imaging, 2007, 34, 822-9.
20. 18F-FMAU and PET. J. Nucl. Med., 2005, 46, 292-6.
21. Wang, J.; Eriksson, S. Phosphorylation of the anti-hepatitis B nucleoside analog 1-(2'-deoxy-2'-fluoro-1-beta-D-arabinofuranosyl)-5-iodouracil (FIAU) by human cytosolic and mitochondrial thymidine kinase and implications for cytotoxicity. Antimicrob. Agents Chemother., 1996, 40, 1555-7.
22. Langen, P.; Etzold, G.; Hintsche, R.; Kowollik, G. 3'-Deoxy-3'-fluorothymidine, a new selective inhibitor of DNA-synthesis. Acta Biol. Med. Ger., 1969, 23, 759-66.
23. Grierson, J.R.; Shields, A.F.; Eary, J.F. Development of a radiosynthesis for 3'-[F-18]fluoro-3'-deoxynucleosides. J. Lab. Comp. Radiopharm., 1997,40, 60-2.
24. Matthes, E.; Lehmann, C.; Scholz, D.; Rosenthal, H.A.; Langen, P. Phosphorylation, anti-HIV activity and cytotoxicity of 3'-fluorothymidine. Biochem. Biophys. Res. Commun., 1988, 153, 825-31.
25. Munch-Petersen, B.; Cloos, L.; Tyrsted, G.; Eriksson, S. Diverging substrate specificity of pure human thymidine kinases 1 and 2 against antiviral dideoxynucleosides. J. Biol. Chem., 1991, 266, 9032-8.
26. Olofsson, S.; Eriksson, S.; Karlsson, A.; Oberg, B. The HIV replication inhibitor 3'-fluoro-3'-deoxythymidine blocks sialylation of N-linked oligosaccharides. Antiviral Res., 1992, 19, 71-80.
27. Shields, A.F.; Grierson, J.R.; Dohmen, B.M.; Machulla, H-J.; Stayanoff, J.C.; Lawhorn-Crews, J.M.; Obradovich, J.E.; Muzik, O.; Mangner, T.J. Imaging proliferation in vivo with [F-18]FLT and positron emission tomography. Nature Med., 1998, 4, 1334-6.
28. 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, 1210-7.
29. 18F-FLT in cancer imaging: does it really reflect proliferation? Eur. J. Nucl. Med. Mol. Imaging, 2008, 35, 523-6.
30. Nanda, D.; de Jong, M.; Vogels, R.; Driesse, R.; Bakker, W.; Bijster, M.; Avezaat, C.; Cox, P.; Morin, K.; Naimi, E.; Knaus, E.; Wiebe, L.; Sillevis Smitt, P. Imaging expression of adenoviral HSV1-tk suicide gene transfer using the nucleoside analogue FIRU. Eur. J. Nucl. Med. Mol. Imaging, 2002, 29, 939-47.
31. Morin, K.W.; Duan, W.; Xu, L.; Zhou, A.; Moharram, A.S.; Knaus, E.E.; McEwan, A.J.B.; Wiebe, L.I. Cytotoxicity and cellular uptake of pyrimidine nucleosides for imaging Herpes simplex Type-1 thymidine kinase (HSV-1 TK) expression in mammalian cells. Nucl. Med. Biol., 2004, 31, 623-30.
32. Codington, J.F.; Doerr, I.L.; Fox, J.J. Nucleosides. XVIII. Synthesis of 2'-fluorothymidine, 2'-fluorodeoxyuridine, and other 2'-halogeno-2'-deoxynucleosides. J. Org. Chem., 1964, 29, 558-64.
33. Doi, Y.; Katafuchi, A.; Fujiwara, Y.; Hitomi, K.; Tainer, J.A.; Ide, H.; Iwai, S. Synthesis and characterization of oligonucleotides containing 2'-fluorinated thymidine glycol as inhibitors of the endonuclease III reaction. Nucleic Acids Res., 2006, 34, 1540-51.
34. Shields, A.F.; Grierson, J.R.; Koxawa, S.M.; Zheng, M. Development of labeled thymidine analogs for imaging tumor proliferation. Nucl. Med. Biol., 1992, 23, 17-22.
35. 131I-labelled 5-halo-1-(2'-fluoro-2'-deoxy-β-D-ribofuranosyl)uracils. J. Med. Chem., 1989, 32, 1289-94.
36. Middleton, W.J.J. New fluorinating reagents. Dialkylaminosulfur fluorides. Org. Chem., 1975, 40, 574-8.
37. Biggadike, K.; Borthwick, A.D.; Evans, D.; Exall, A.M.; Kirk, B.E.; Roberts, S.M.; Stephenson, L.; Youds, P. Use of diethylaminosulphur trifluoride (DAST) in the preparation of synthons of carbocyclic nucleosides J. Chem. Soc., Perkin Trans., 1988, 1, 549.
38. 18F]fluorouridine via a new nosylate precursor. J. Label. Compd. Radiopharm., 2006, 49, 1237-46.
39. Legorburu, U.; Reese, C.B.; Song, Q. Conversion of uridine into 2'-O-(2-methoxyethyl)-uridine and 2'-O-(2-methoxyethyl)cytidine. Tetrahedron, 1999, 55, 5635-40.
40. Ozaki, H.; Nakajima, K.; Tatsui, K.; Izumi, C.; Kuwahara, M.; Sawai, H. Convenient synthesis of oligodeoxyribonuclotides bearing arabinoafuranosyl pyrimidine derivatives and its duplex formation with complementary DNA. Bioorg. Med. Chem. Lett., 2003, 13, 2441-3.
41. Manfredini, S.; Baraldi, P.G.; Durini, E.; Porcu, L.; Angusti, A.; Vertuani, S.; Solaroli, N.; De Clercq, E.; Karlsson, A.; Balzarini, J. Design, synthesis and enzymatic activity of highly selective human mitochondrial thymidine kinase inhibitors. Bioorg. Med. Chem. Lett., 2001, 11. 1329-32.
42. 18F]fluorothymidine using (5'-O-dimethoxytrityl-2'-deoxy-3'-O-nosyl-threopentofuranosyl)thymine and its 3-N-BOC-protected analogue as a labeling precursor. Nucl. Med. Biol., 2003, 30, 151-157.
43. Grierson, J.R.; Shields, A.F. An improved radiosynthesis of [F-18]FLT. J. Label. Compd. Radiopharm., 1999, 42, S525-6.
44. 18F]FLT for imaging cellular proliferation in vivo. Nucl. Med. Biol., 2000, 27, 143-6.
45. 18F]FLT. Nucl. Med. Biol., 2002, 29, 263-73.
46. 18F]fluorothymidine using three precursors. Appl. Radiat. Isot., 2006, 64, 187-93.
47. Myers, A.G.; Gin, D.Y.; Rogers, D.H. Synthetic studies of the tunicamycin antibiotics. Preparation of (+)-tunicaminyluracil, (+)-tunicamycin-V, and 5'-epi-tunicamycin-V. J. Am. Chem. Soc., 1994,116, 4697-718.
48. Abrams, D.N.; Mercer, J.R.; Knaus, E.E.; Wiebe, L.I. The synthesis of radiolabelled 1-(2'-fluoro-2'-deoxy-β-D-ribofuranosyl)-uracil and 1-(2'-chloro-2'-deoxy-β-D-ribofuranosyl)-uracil. Int. J. App. Radiat. Isot., 1985, 36, 233-8.
49. Shi, J.; Du, J.; Ma, T.; Pankiewicz, K.W.; Patterson, S.E.; Tharnish, P.M.; McBrayer, T.R.; Stuyver, L.J.; Otto, M.J.; Chu, C.K.; Schinazi, R.F.; Watanabe, K.A. Synthesis and anti-viral activity of a series of D-and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system. Bioorg. Med. Chem., 2005, 13, 1641-52.