Nuclear Medicine and Biology
Volume 33, Issue 6 , Pages 765-772 , August 2006

Alkyl-fluorinated thymidine derivatives for imaging cell proliferation: II. Synthesis and evaluation of N3-(2-[18F]fluoroethyl)-thymidine

  • Jun Toyohara

      Affiliations

    • Probe Research Section, Department of Molecular Probe, Molecular Imaging Center, National Institute of Radiological Sciences, Chiba 263-8555, Japan
    • Corresponding Author InformationCorresponding author. Tel.: +81 43 206 4041; fax: +81 43 206 3261.
    • ,
  • Akio Hayashi

      Affiliations

    • Research and Development Division, Research Center, Nihon Medi-Physics Co., Ltd., Chiba, Japan
    • ,
  • Akie Gogami

      Affiliations

    • Research and Development Division, Research Center, Nihon Medi-Physics Co., Ltd., Chiba, Japan
    • ,
  • Yasuhisa Fujibayashi

      Affiliations

    • Biomedical Imaging Research Center, University of Fukui, Fukui, Japan

Received 17 January 2006 ,Revised 16 May 2006 ,Accepted 11 June 2006.

References 

  1. Grierson JR, Schwartz JL, Muzi M, Jordan R, Krohn KA. Metabolism of 3′-deoxy-3′-[F-18]fluorothymidine in proliferating A549 cells: validations for positron emission tomography. Nucl Med Biol. 2004;31:829–837
  2. Martin SJ, Eisenbarth JA, Wagner-Utermann U, Mier W, Henze M, Pritzkow H, et al. A new precursor for the radiosynthesis of [18F]FLT. Nucl Med Biol. 2002;29:263–273
  3. Edgell WF, Parts L. Synthesis of alkyl and substituted alkyl fluorides from p-toluenesulfonic acid esters. The preparation of p-toluenesulfonic acid esters of lower alcohols. J Am Chem Soc. 1955;77:4899–4902
  4. Kit S, Dubbes DR, Piekarski LJ, Hsu TC. Deletion of thymidine kinase activity from L cells resistant to bromodeoxyuridine. Exp Cell Res. 1963;31:297–312
  5. Ayusawa D, Shimizu K, Koyama H, Kaneda S, Takeishi K, Seno T. Cell-cycle-directed regulation of thymidylate synthase messenger RNA in human diploid fibroblasts stimulated to proliferate. J Mol Biol. 1986;190:559–567
  6. Chi DY, Kilbourn MR, Katzenellenbogen JA, Brodack JW, Welch MJ. Synthesis of no-carrier-added N-([18F]fluoroalkyl)spiperone derivatives. Appl Radiat Isot. 1986;37:1173–1180
  7. Hamacher K, Coenen HH, Stocklin G. Efficient stereospecific synthesis of no-carrier-added 2-[18F]-fluoro-2-deoxy-d-glucose using aminopolyether supported nucleophilic substitution. J Nucl Med. 1986;27:235–238
  8. Toyohara J, Waki A, Takamatsu S, Yonekura Y, Magata Y, Fujibayashi Y. Basis of FLT as a cell proliferation marker: comparative uptake studies with [3H]thymidine and [3H]arabinothymidine, and cell-analysis in 22 asynchronously growing tumor cell lines. Nucl Med Biol. 2002;29:281–287
  9. Mori T, Kasamatsu S, Mosdzianowski C, Welch MJ, Yonekura Y, Fujibayashi Y. Automatic synthesis of 16α-[18F]fluoro-17β-estradiol ([18F]FES) using a cassette-type [18F]fluorodeoxyglucose synthesizer. Nucl Med Biol. 2006;33:281–286
  10. van Waarde A, Cobben DC, Suurmeijer AJ, Maas B, Vaalburg W, de Vries EF, et al. Selectivity of 18F-FLT and 18F-FDG for differentiating tumor from inflammation in a rodent model. J Nucl Med. 2004;45:695–700
  11. Rasey JS, Grierson JR, Wiens LW, Kolb PD, Schwartz JL. Validation of FLT uptake as a measure of thymidine kinase-1 activity in A549 carcinoma cells. J Nucl Med. 2002;43:1210–1217
  12. Guo Y, Kotova E, Chen Z-S, Lee K, Hopper-Borge E, Belinsky MG, et al. MRP8, ATP-binding cassette C11 (ABCC11), is a cyclic nucleotide efflux pump and a resistance factor for fluoropyrimidines 2′,3′-dideoxycytidine and 9′-(2′-phosphonylmethoxyethyl)adenine. J Biol Chem. 2003;278:29509–29514
  13. Barthel H, Cleij MC, Collingridge DR, Hutchinson OC, Osman S, He Q, et al. 3′-Deoxy-3′-[18F]fluorothymidine as a new marker for monitoring tumor response to antiproliferative therapy in vivo with positron emission tomography. Cancer Res. 2003;63:3791–3798
  14. Barthel H, Perumal M, Latigo J, He Q, Brady F, Luthra SK, et al. The uptake of 3′-deoxy-3′-[18F]fluorothymidine into L5178Y tumors in vivo is dependent on thymidine kinase 1 protein levels. Eur J Nucl Med Mol Imaging. 2005;32:257–263

PII: S0969-8051(06)00102-8

doi: 10.1016/j.nucmedbio.2006.06.001

Nuclear Medicine and Biology
Volume 33, Issue 6 , Pages 765-772 , August 2006

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