Literature DB >> 20447555

Improved synthesis of 2'-deoxy-2'-[18F]-fluoro-1-beta-D-arabinofuranosyl-5-iodouracil ([18F]-FIAU).

Harry Anderson1, Nagavarakishore Pillarsetty, Melchor Cantorias, Jason S Lewis.   

Abstract

An improved synthesis of 2'-[(18)F]-fluoro-2'-deoxy-1-beta-D-arabinofuranosyl-5-iodouracil ([(18)F]-FIAU) has been developed. The method utilizes trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed coupling of 2-deoxy-2-[(18)F]-fluoro-1,3,5-tri-O-benzoyl-d-arabinofuranose with 2,4-bis(trimethylsilyloxy)-5-iodouracil to yield the protected dibenzoyl-[(18)F]-FIAU. Dibenzoyl-[(18)F]-FIAU was deprotected with sodium methoxide to yield a mixture of alpha- and beta-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 [(18)F]-fluoride. The average isolated yield of the required beta-anomer was 10+/-6% (decay corrected) with average specific activity of 125 mCi/micromol. (c) 2010 Elsevier Inc. All rights reserved.

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Year:  2010        PMID： 20447555      PMCID： PMC4410717          DOI： 10.1016/j.nucmedbio.2010.01.003

Source DB:  PubMed          Journal:  Nucl Med Biol        ISSN： 0969-8051            Impact factor:   2.408


  14 in total

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Journal:  Mol Imaging Biol       Date:  2007-12-22       Impact factor: 3.488

4.  Imaging of HSV-tk Reporter gene expression: comparison between [18F]FEAU, [18F]FFEAU, and other imaging probes.

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6.  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.

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Journal:  Nucl Med Biol       Date:  2003-04       Impact factor: 2.408

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Journal:  J Nucl Med       Date:  2008-06-13       Impact factor: 10.057

Review 10.  Antivirals and antiviral strategies.

Authors:  Erik De Clercq
Journal:  Nat Rev Microbiol       Date:  2004-09       Impact factor: 60.633
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  10 in total

1.  An improved strategy for the synthesis of [¹⁸F]-labeled arabinofuranosyl nucleosides.

Authors:  Hanwen Zhang; Melchor V Cantorias; NagaVaraKishore Pillarsetty; Eva M Burnazi; Shangde Cai; Jason S Lewis
Journal:  Nucl Med Biol       Date:  2012-07-18       Impact factor: 2.408

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Authors:  Jeffrey Collins; Christopher M Waldmann; Christopher Drake; Roger Slavik; Noel S Ha; Maxim Sergeev; Mark Lazari; Bin Shen; Frederick T Chin; Melissa Moore; Saman Sadeghi; Michael E Phelps; Jennifer M Murphy; R Michael van Dam
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3.  Plug-and-play modules for flexible radiosynthesis.

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Journal:  Appl Radiat Isot       Date:  2013-04-25       Impact factor: 1.513

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Review 5.  The Current Role of Microfluidics in Radiofluorination Chemistry.

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6.  Radiosynthesis of 6'-Deoxy-6'[18F]Fluorosucrose via Automated Synthesis and Its Utility to Study In Vivo Sucrose Transport in Maize (Zea mays) Leaves.

Authors:  David Rotsch; Tom Brossard; Saadia Bihmidine; Weijiang Ying; Vikram Gaddam; Michael Harmata; J David Robertson; Michael Swyers; Silvia S Jurisson; David M Braun
Journal:  PLoS One       Date:  2015-05-29       Impact factor: 3.240

7.  Tumor-specific targeting with modified Sindbis viral vectors: evaluation with optical imaging and positron emission tomography in vivo.

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8.  ELIXYS - a fully automated, three-reactor high-pressure radiosynthesizer for development and routine production of diverse PET tracers.

Authors:  Mark Lazari; Kevin M Quinn; Shane B Claggett; Jeffrey Collins; Gaurav J Shah; Henry E Herman; Brandon Maraglia; Michael E Phelps; Melissa D Moore; R Michael van Dam
Journal:  EJNMMI Res       Date:  2013-07-12       Impact factor: 3.138

9.  TMSOTf assisted synthesis of 2'-deoxy-2'-[18F]fluoro-β-D-arabinofuranosylcytosine ([18F]FAC).

Authors:  Kishore K Gangangari; John L Humm; Steven M Larson; Naga Vara Kishore Pillarsetty
Journal:  PLoS One       Date:  2018-05-01       Impact factor: 3.240

10.  Radiosynthesis of [18F]-Labelled Pro-Nucleotides (ProTides).

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Journal:  Molecules       Date:  2020-02-06       Impact factor: 4.411
  10 in total

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