Nuclear Medicine and Biology
Volume 35, Issue 4 , Pages 413-423 , May 2008

3′-Sulfonylesters of 2,5′-anhydro-1-(2-deoxy-β-d-threo-pentofuranosyl)thymine as precursors for the synthesis of [18F]FLT: syntheses and radiofluorination trials

  • Albert D. Windhorst

      Affiliations

    • Department of Nuclear Medicine and PET Research, Vrije Universiteit Medical Center, De Boelelaan 1085c, Amsterdam, The Netherlands
    • Corresponding Author InformationCorresponding author.
    • ,
  • Pieter J. Klein

      Affiliations

    • Department of Nuclear Medicine and PET Research, Vrije Universiteit Medical Center, De Boelelaan 1085c, Amsterdam, The Netherlands
    • ,
  • Joseph Eisenbarth

      Affiliations

    • Department of Radiopharmaceutical Chemistry, German Cancer Research Center, Im Neuenheimer Feld 280, 69120 Heidelberg, Germany
    • ,
  • Thomas Oeser

      Affiliations

    • Department of Organic Chemistry, University of Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
    • ,
  • Perry S. Kruijer

      Affiliations

    • BV Cyclotron VU, Amsterdam, The Netherlands
    • ,
  • Michael Eisenhut

      Affiliations

    • Department of Radiopharmaceutical Chemistry, German Cancer Research Center, Im Neuenheimer Feld 280, 69120 Heidelberg, Germany

Received 28 September 2007 ,Revised 18 February 2008 ,Accepted 18 February 2008.

References 

  1. Shields AF, Grierson JR, Dohmen BM, Machulla HJ, Stayanoff JC, Lawhorn-Crews JM, et al. Imaging proliferation in vivo with [F-18]FLT and positron emission tomography. Nat Med. 1998;4:1334–1336
  2. Barthel H, Cleij MC, Collingridge DR, Hutchinson OC, Osman S, He QM, et al. 3′-Deoxy-3′-[F-18]fluorothymidine as a new marker for monitoring tumor response to antiproliferative therapy in vivo with positron emission tomography. Cancer Res. 2003;63:3791–3798
  3. Been LB, Suurmeijer AJH, Cobben DCP, Jager PL, Hoekstra HJ, Elsinga PH. [F-18]FLT-PET in oncology: current status and opportunities. Eur J Nucl Med Mol Imaging. 2004;31:1659–1672
  4. Buck AK, Schirrmeister H, Hetzel M, von der Heide M, Halter G, Glatting G, et al. 3-Deoxy-3-[F-18]fluorothymidine-positron emission tomography for noninvasive assessment of proliferation in pulmonary nodules. Cancer Res. 2002;62:3331–3334
  5. Buck AK, Halter G, Schirrmeister H, Kotzerke J, Wurziger I, Glatting G, et al. Imaging proliferation in lung tumors with PET: F-18-FLT versus F-18-FDG. J Nucl Med. 2003;44:1426–1431
  6. Chen W, Cloughesy T, Kamdar N, Satyamurthy N, Bergsneider M, Liau L, et al. Imaging proliferation in brain tumors with F-18-FLT PET: comparison with F-18-FDG. J Nucl Med. 2005;46:945–952
  7. Cobben DCP, Jager PL, Elsinga PH, Maas B, Suurmeijer AJH, Hoekstra HJ. 3′-F-18-fluoro-3′-deoxy-l-thymidine: a new tracer for staging metastatic melanoma?. J Nucl Med. 2003;44:1927–1932
  8. Cobben DCP, Elsinga PH, Hoekstra HJ, Suurmeijer AJH, Vaalburg W, Maas B, et al. Is F-18-3′-fluoro-3′-deoxy-l-thymidine useful for the staging and restaging of non-small cell lung cancer?. J Nucl Med. 2004;45:1677–1682
  9. Cobben DCP, van der Laan BFAM, Maas B, Vaalburg W, Suurmeijer AJH, Hoekstra HJ, et al. F-18-FLT PET for visualization of laryngeal cancer: comparison with F-18-FDG PET. J Nucl Med. 2004;45:226–231
  10. Dittmann H, Dohmen BM, Paulsen F, Eichhorn K, Eschmann SM, Horger M, et al. [F-18]FLT PET for diagnosis and staging of thoracic tumours. Eur J Nucl Med Mol Imaging. 2003;30:1407–1412
  11. Leyton J, Alao JP, Da Costa M, Stavropoulou AV, Latigo JR, Perumal M, et al. In vivo biological activity of the histone deacetylase inhibitor LA0824 is detectable with 3′-deoxy-3′-[F-18]fluorothymidine positron emission tomography. Cancer Res. 2006;66:7621–7629
  12. Lu L, Samuelsson L, Bergstrom M, Sato K, Fasth KJ, Langstrom B. Rat studies comparing C-11-FMAU, F-18-FLT, and Br-76-BFU as proliferation markers. J Nucl Med. 2002;43:1688–1698
  13. Mier W, Haberkorn U, Eisenhut M. [F-18]FLT; portrait of a proliferation marker. Eur J Nucl Med Mol Imaging. 2002;29:165–169
  14. Saga T, Kawashima H, Araki N, Takahashi JA, Nakashima Y, Higashi T, et al. Evaluation of primary brain tumors with FLT-PET: usefulness and limitations. Clin Nucl Med. 2006;31:774–780
  15. Shields AF. Positron emission tomography measurement of tumor metabolism and growth: its expanding role in oncology. Mol Imaging Biol. 2006;8:141–150
  16. Sugiyama M, Sakahara H, Sato K, Harada N, Fukumoto D, Kakiuchi T, et al. Evaluation of 3′-deoxy-3′-F-18-fluorothymidine for monitoring tumor response to radiotherapy and photodynamic therapy in mice. J Nucl Med. 2004;45:1754–1758
  17. van Waarde A, Cobben DCP, Suurmeijer AJH, Maas B, Vaalburg W, de Vries EFJ, et al. Selectivity of F-18-FLT and F-18-FDG for differentiating tumor from inflammation in a rodent model. J Nucl Med. 2004;45:695–700
  18. Wagner M, Seitz U, Buck A, Neumaier B, Schultheiss S, Bangerter M, et al. 3′-[F-18]fluoro-3′-deoxythymidine ([F-18]-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
  19. Wilson IK, Chatterjee S, Wolf W. Synthesis of 3′-fluoro-3′-deoxythymidine and studies of its F-18 radiolabeling, as a tracer for the noninvasive monitoring of the biodistribution of drugs against AIDS. J Fluor Chem. 1991;55:283–289
  20. Grierson JR, Shields AF. Radiosynthesis of 3′-deoxy-3′-[F-18]fluorothymidine: [F-18]FLT for imaging of cellular proliferation in vivo. Nucl Med Biol. 2000;27:143–156
  21. Machulla HJ, Blocher A, Kuntzsch M, Piert M, Wei R, Grierson JR. Simplified labeling approach for synthesizing 3′-deoxy-3′-[F-18]fluorothymidine ([F-18]FLT). J Radioanal Nucl Chem. 2000;243:843–846
  22. Martin SJ, Eisenbarth JA, Wagner-Utermann U, Mier W, Henze M, Pritzkow H, et al. A new precursor for the radiosynthesis of [F-18]FLT. Nucl Med Biol. 2002;29:263–273
  23. Kim DW, Ahn DS, Oh YH, Lee S, Kil HS, Oh SJ, et al. A new class of S(N)2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules. J Am Chem Soc. 2006;128:16394–16397
  24. Joshi BV, Rao TS, Reese CB. Conversion of some pyrimidine 2′-deoxyribonucleosides into the corresponding 2′,3′-didehydro-2′,3′-dideoxynucleosides. J Chem Soc Perkin Trans 1. 1992;2537–2544
  25. Mansuri MM, Starrett JE, Ghazzouli I, Hitchcock MJM, Sterzycki RZ, Brankovan V, et al. 1-(2,3-Dideoxy-beta-d-glycero-pent-2-enofuranosyl)thymine — a highly potent and selective anti-HIV agent. J Med Chem. 1989;32:461–466
  26. Paramashivappa R, Phani Kumar P, Subba Rao PV, Srinivasa Rao A. Simple and efficient method for the synthesis of2,3-didehydro-3-deoxythymidine (d4T). Tet Lett. 2003;44:1003–1005
  27. Horwitz JP, Chua J, Noel M. Nucleosides: 5. Monomesylates of 1-(2]-deoxy-beta-d-lyxofuranosyl)thymine. J Org Chem. 1964;29:2076–2078
  28. Lin TS, Shen ZY, August EM, Brankovan V, Yang HY, Ghazzouli I, et al. Synthesis and antiviral activity of several 2,5′-anhydro analogs of 3′-azido-3′-deoxythymidine, 3′-azido-2′,3′-dideoxyuridine, 3′-azido-2′,3′-dideoxy-5-halouridines, and 3′-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia-virus. J Med Chem. 1989;32:1891–1895
  29. Schram KH, Ratcliff S, Neenan J. O-18 labeled nucleosides:1. A general-method for the synthesis of specifically labeled pyrimidine deoxyribosides. J Labell Compnds and Radiopharm. 1982;19:399–404
  30. Tewson TJ. Production of F-18 fluorothymidine; substrates and yields. J Labell Compnds Radiopharm. 2003;46:S222
  31. Sheldrick GM. Bruker analytical X-ray division, Program ‘SADABS V2.03 for absorption correction’. 2001;Madison (WI)
  32. Sheldrick GM. Bruker analytical X-ray division, Software package ‘SHELXTL V6.12 for structure solution and refinement’. 2001;Madison (WI)

PII: S0969-8051(08)00060-7

doi: 10.1016/j.nucmedbio.2008.02.012

Nuclear Medicine and Biology
Volume 35, Issue 4 , Pages 413-423 , May 2008

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