Nuclear Medicine and Biology
Volume 37, Issue 4 , Pages 439-442 , May 2010

Improved synthesis of 2′-deoxy-2′-[18F]-fluoro-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU)

  • Harry Anderson

      Affiliations

    • Advion BioSystems, 19 Brown Road, Ithaca, NY 14850, USA
  • ,
  • NagaVaraKishore Pillarsetty

      Affiliations

    • Radiochemistry Service, Department of Radiology, Memorial Sloan-Kettering Cancer Center, New York, NY 10065, USA
  • ,
  • Melchor Cantorias

      Affiliations

    • Radiochemistry Service, Department of Radiology, Memorial Sloan-Kettering Cancer Center, New York, NY 10065, USA
  • ,
  • Jason S. Lewis

      Affiliations

    • Radiochemistry Service, Department of Radiology, Memorial Sloan-Kettering Cancer Center, New York, NY 10065, USA
    • Corresponding Author InformationCorresponding author. Tel.: +1 646 888 3038; fax: +1 646 422 0408.

Received 18 September 2009 ,Revised 4 January 2010 ,Accepted 17 January 2010.

References 

  1. Serganova I, Mayer-Kukuck P, Huang R, Blasberg R. Molecular imaging: reporter gene imaging. Handb Exp Pharmacol. 2008;167–223
  2. Ponomarev V. Nuclear imaging of cancer cell therapies. J Nucl Med. 2009;50:1013–1016
  3. Keller PM, Fyfe JA, Beauchamp L, Lubbers CM, Furman PA, Schaeffer HJ, et al. Enzymatic phosphorylation of acyclic nucleoside analogs and correlations with antiherpetic activities. Biochem Pharmacol. 1981;30:3071
  4. De Clercq E. Antivirals and antiviral strategies. Nat Rev Microbiol. 2004;2:704
  5. Gambhir SS, Herschman HR, Cherry SR, Barrio JR, Satyamurthy N, Toyokuni T, et al. Imaging transgene expression with radionuclide imaging technologies. Neoplasia. 2000;2:118–138
  6. Doubrovin M, Ponomarev V, Beresten T, Balatoni J, Bornmann W, Finn R, et al. Imaging transcriptional regulation of p53-dependent genes with positron emission tomography in vivo. Proc Natl Acad Sci U S A. 2001;98:9300
  7. Koehne G, Doubrovin M, Doubrovina E, Zanzonico P, Gallardo HF, Ivanova A, et al. Serial in vivo imaging of the targeted migration of human HSV-TK-transduced antigen-specific lymphocytes. Nat Biotechnol. 2003;21:405–413
  8. Dobrenkov K, Olszewska M, Likar Y, Shenker L, Gunset G, Cai S, et al. Monitoring the efficacy of adoptively transferred prostate cancer-targeted human T lymphocytes with PET and bioluminescence imaging. J Nucl Med. 2008;49:1162–1170
  9. Pomper MG, Hammond H, Yu X, Ye Z, Foss CA, Lin DD, et al. Serial imaging of human embryonic stem-cell engraftment and teratoma formation in live mouse models. Cell Res. 2009;19:370–379
  10. Miyagawa T, Gogiberidze G, Serganova I, Cai S, Balatoni JA, Thaler HT, et al. Imaging of HSV-tk reporter gene expression: comparison between [18F]FEAU, [18F]FFEAU, and other imaging probes. J Nucl Med. 2008;49:637–648
  11. Chin FT, Namavari M, Levi J, Subbarayan M, Ray P, Chen X, et al. Semiautomated radiosynthesis and biological evaluation of [18F]FEAU: a novel PET imaging agent for HSV1-tk/sr39tk reporter gene expression. Mol Imaging Biol. 2008;10:82–91
  12. Alauddin MM, Shahinian A, Park R, Tohme M, Fissekis JD, Conti PS. In vivo evaluation of 2′-deoxy-2′-[(18)F]fluoro-5-iodo-1-beta-d-arabinofuranosyluracil ([18F]FIAU) and 2′-deoxy-2′-[18F]fluoro-5-ethyl-1-beta-d-arabinofuranosyluracil ([18F]FEAU) as markers for suicide gene expression. Eur J Nucl Med Mol Imaging. 2007;34:822–829
  13. Alauddin MM, Conti PS, Fissekis JD. A general synthesis of 2′-deoxy-2′-[F-18]fluoro-1-beta-d-arabinofuranosyluracil and its 5-substituted nucleosides. J Labell Compounds Radiopharm. 2003;46:285
  14. Mangner TJ, Klecker RW, Anderson L, Shields AF. Synthesis of 2′-deoxy-2′-[18F]fluoro-beta-d-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation. Synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU. Nucl Med Biol. 2003;30:215
  15. Vorbruggen H, Bennua B. Nucleoside synthesis: 19. New simplified nucleoside synthesis. Tetrahedron Lett. 1978;1339–1342
  16. Yamaguchi T, Saneyoshi M. Synthetic nucleosides and nucleotides: 21. On the synthesis and biological evaluations of 2′-deoxy-alpha-d-ribofuranosyl nucleosides and nucleotides. Chem Pharm Bull. 1984;32:1441–1450

PII: S0969-8051(10)00022-3

doi: 10.1016/j.nucmedbio.2010.01.003

Nuclear Medicine and Biology
Volume 37, Issue 4 , Pages 439-442 , May 2010