Nuclear Medicine and Biology
Volume 35, Issue 1 , Pages 75-82 , January 2008

Improved synthesis and metabolic stability analysis of the dopamine transporter ligand [18F]FECT

  • Satish K. Chitneni

      Affiliations

    • Laboratory for Radiopharmacy, Faculty of Pharmaceutical Sciences, Katholieke Universiteit Leuven, BE-3000, Leuven, Belgium
    • ,
  • Lucette Garreau

      Affiliations

    • Médecine Nucléaire, CHRU Tours, F-37200, Fours, France
    • ,
  • Bernard Cleynhens

      Affiliations

    • Laboratory for Radiopharmacy, Faculty of Pharmaceutical Sciences, Katholieke Universiteit Leuven, BE-3000, Leuven, Belgium
    • ,
  • Nele Evens

      Affiliations

    • Laboratory for Radiopharmacy, Faculty of Pharmaceutical Sciences, Katholieke Universiteit Leuven, BE-3000, Leuven, Belgium
    • ,
  • Marva Bex

      Affiliations

    • Department of Nuclear Medicine, Katholieke Universiteit Leuven, Leuven, BE-3000, Belgium
    • ,
  • Peter Vermaelen

      Affiliations

    • Department of Nuclear Medicine, Katholieke Universiteit Leuven, Leuven, BE-3000, Belgium
    • ,
  • Sylvie Chalon

      Affiliations

    • Médecine Nucléaire, CHRU Tours, F-37200, Fours, France
    • ,
  • Roger Busson

      Affiliations

    • Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Katholieke Universiteit Leuven, Leuven, BE-3000, Belgium
    • ,
  • Denis Guilloteau

      Affiliations

    • Médecine Nucléaire, CHRU Tours, F-37200, Fours, France
    • ,
  • Koen Van Laere

      Affiliations

    • Department of Nuclear Medicine, Katholieke Universiteit Leuven, Leuven, BE-3000, Belgium
    • ,
  • Alfons Verbruggen

      Affiliations

    • Laboratory for Radiopharmacy, Faculty of Pharmaceutical Sciences, Katholieke Universiteit Leuven, BE-3000, Leuven, Belgium
    • ,
  • Guy Bormans

      Affiliations

    • Laboratory for Radiopharmacy, Faculty of Pharmaceutical Sciences, Katholieke Universiteit Leuven, BE-3000, Leuven, Belgium
    • Corresponding Author InformationCorresponding author. Onderwijs & Navorsing 2, Herestraat-49, Bus 821, BE-3000, Leuven, Belgium. Tel.: +32 16 330447; fax: +32 16 330449.

Received 23 April 2007 ,Revised 6 August 2007 ,Accepted 4 September 2007.

References 

  1. Elsinga PH, Hatano K, Ishiwata K. PET tracers for imaging of the dopaminergic system. Curr Med Chem. 2006;13:2139–2153
  2. Halldin C, Erixon-Lindroth N, Pauli S, Chou YH, Okubo Y, Karlsson P, et al. [C-11]PE2I: a highly selective radioligand for PET examination of the dopamine transporter in monkey and human brain. Eur J Nucl Med Mol Imaging. 2003;30:1220–1230
  3. Chalon S, Garreau L, Emond P, Zimmer L, Vilar MP, Besnard JC, et al. Pharmacological characterization of (E)-N-(3-iodoprop-2-enyl)-2 beta-carboxymethoxy-3 beta-(4′-methylphenyl)nortropane as a selective and potent inhibitor of the neuronal dopamine transporter. J Pharmacol Exp Ther. 1999;291:648–654
  4. Goodman MM, Kilts CD, Keil R, Shi B, Martarello L, Xing DX, et al. F-18-labeled FECNT: a selective radioligand for PET imaging of brain dopamine transporters. Nucl Med Biol. 2000;27:1–12
  5. Voll RJ, McConathy J, Waldrep MS, Crowe RJ, Goodman MM. Semi-automated preparation of the dopamine transporter ligand [F-18]FECNT for human PET imaging studies. Appl Radiat Isot. 2005;3:353–361
  6. Davis MR, Votaw JR, Bremner JD, Byas-Smith MG, Faber TL, Voll RJ, et al. Initial human PET imaging studies with the dopamine transporter ligand F-18-FECNT. J Nucl Med. 2003;44:855–861
  7. Zoghbi SS, Shetty HU, Ichise M, Fujita M, Imaizumi M, Liow JS, et al. PET Imaging of the dopamine transporter with 18F-FECNT: a polar radiometabolite confounds brain radioligand measurements. J Nucl Med. 2006;47:520–527
  8. Shetty HU, Sami SZ, Jeih-San L, Masanori I, Jinsoo H, John LM, et al. Identification and regional distribution in rat brain of radiometabolites of the dopamine transporter PET radioligand [11C]PE2I. Eur J Nucl Med Mol Imaging. 2007;34:667–678(s00259-006-0277-1)
  9. Dolle F, Emond P, Mavel S, Demphel S, Hinnen F, Mincheva Z, et al. Synthesis, radiosynthesis and in vivo preliminary evaluation of [C-11]LBT-999, a selective radioligand for the visualisation of the dopamine transporter with PET. Bioorg Med Chem. 2006;14:1115–1125
  10. Wilson AA, Dasilva JN, Houle S. Synthesis of two radiofluorinated cocaine analogs using distilled 2-[F-18]fluoroethyl bromide. Appl Radiat Isot. 1995;46:765–770
  11. Wilson AA, Dasilva JN, Houle S. In vivo evaluation of [C-11]- and [F-18]-labelled cocaine analogues as potential dopamine transporter ligands for positron emission tomography. Nucl Med Biol. 1996;23:141–146
  12. Gu XH, Zong R, Kula NS, Baldessarini RJ, Neumeyer JL. Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: potential positron emission tomography (PET) imaging agents for the dopamine transporter. Bioorg Med Chem Lett. 2001;11:3049–3053
  13. Casteels C, Vermaelen P, Nuyts J, Van Der Linden A, Baekelandt V, Mortelmans L, et al. Construction and evaluation of multitracer small-animal PET probabilistic atlases for voxel-based functional mapping of the rat brain. J Nucl Med. 2006;47:1858–1866
  14. Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, et al. Cocaine and 3-beta-(4′-substituted phenyl)tropane-2-beta-carboxylic acid ester and amide analogs — new high-affinity and selective compounds for the dopamine transporter. J Med Chem. 1995;38:379–388
  15. Cleynhens BJ, de Groot TJ, Vanbilloen HP, Kieffer D, Mortelmans L, Bormans GM, et al. Technetium-99m labelled integrated tropane-BAT as a potential dopamine transporter tracer. Bioorg Med Chem. 2005;13:1053–1058
  16. Zhang MR, Furutsuka K, Yoshida Y, Suzuki K. How to increase the reactivity of [F-18]fluoroethyl bromide: [F-18]fluoroethylation of amine, phenol and amide functional groups with [F-18]FEtBr, [F-18]FEtBr/NaI and [F-18]FEtOTf. J Label Compd Radiopharm. 2003;46:587–598
  17. Young RC, Mitchell RC, Brown TH, Ganellin CR, Griffiths R, Jones M, et al. Development of a new physicochemical model for brain penetration and its application to the design of centrally acting H-2-receptor histamine-antagonists. J Med Chem. 1988;31:656–671
  18. Dishino DD, Welch MJ, Kilbourn MR, Raichle ME. Relationship between lipophilicity and brain extraction of C-11-labeled radiopharmaceuticals. J Nucl Med. 1983;24:1030–1038
  19. Chitneni SK, Deroose CM, Balzarini J, Gijsbers R, Celen SJL, deGroot TJ, et al. Synthesis and preliminary evaluation of 18F- or 11C-labeled bicyclic nucleoside analogues as potential probes for imaging varicella-zoster virus thymidine kinase gene expression using positron emission tomography. J Med Chem. 2007;50:1041–1049

☆ This work was supported by the Animone-SBO research grant of the Flemish Institute supporting Scientific-Technological Research in Industry (IWT), and by the EC-FP6-project DiMI, LSHB-CT-2005-512146.

PII: S0969-8051(07)00239-9

doi: 10.1016/j.nucmedbio.2007.09.001

Nuclear Medicine and Biology
Volume 35, Issue 1 , Pages 75-82 , January 2008

Article Tools

* Image Usage & Resolution