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; received in revised form 4 January 2010; accepted 17 January 2010. published online 08 March 2010.

Abstract 

An improved synthesis of 2′-[18F]-fluoro-2′-deoxy-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU) has been developed. The method utilizes trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed coupling of 2-deoxy-2-[18F]-fluoro-1,3,5-tri-O-benzoyl-d-arabinofuranose with 2,4-bis(trimethylsilyloxy)-5-iodouracil to yield the protected dibenzoyl-[18F]-FIAU. Dibenzoyl-[18F]-FIAU was deprotected with sodium methoxide to yield a mixture of α- and β-anomers in a ratio of 1:1, which were purified by HPLC. The procedure described in this article eliminates the need for HBr activation of the sugar prior to coupling with silylated iodouracil and is suitable for automation. The total reaction time was about 110 min, starting from [18F]-fluoride. The average isolated yield of the required β-anomer was 10±6% (decay corrected) with average specific activity of 125 mCi/μmol.

Keywords: FIAU, PET, Microfluidics, HSV1-tk

To access this article, please choose from the options below

Login to an existing account or Register a new account.

  • Purchase this article for 31.50 USD (You must login/register to purchase this article)

    Online access for 24 hours. The PDF version can be downloaded as your permanent record.

  • Subscribe to this title

    Get unlimited online access to this article and all other articles in this title 24/7 for one year.

  • Claim access now

    For current subscribers with Society Membership or Account Number.

  • Visit SciVerse ScienceDirect to see if you have access via your institution.
 

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

Article Tools

* Image Usage & Resolution