Nuclear Medicine and Biology
Volume 33, Issue 6 , Pages 785-795 , August 2006

Synthesis and radiolabeling of N-[4-[4-(2-[11C]methoxyphenyl)piperazin-1-yl]butyl]benzo[b]thiophene-2-carboxamide — a potential radiotracer for D3 receptor imaging with PET

  • Bertrand Kuhnast

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Héric Valette

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Laurent Besret

      Affiliations

    • CNRS URA2210, CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Stéphane Demphel

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Christine Coulon

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Michèle Ottaviani

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Martine Guillermier

      Affiliations

    • CNRS URA2210, CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Michel Bottlaender

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • ,
  • Frédéric Dollé

      Affiliations

    • Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France
    • Corresponding Author InformationCorresponding author. Tel.: +33 1 69 86 77 04; fax: +33 1 69 86 77 49.

Received 27 February 2006 ,Revised 24 May 2006 ,Accepted 25 May 2006.

References 

  1. Sokoloff P, Giros B, Martres MP, Bouthenet ML, Schwartz JC. Molecular cloning and characterization of a novel dopamine D3 receptor as a target for neuroleptics. Nature. 1990;347:146–151
  2. Levant B. The D3 dopamine receptor: neurobiology and potential clinical relevance. Pharmacol Rev. 1997;49:231–252
  3. Campiani G, Butini S, Trotta F, Fattorusso C, Catalanotti FA, Gemma S, et al. Synthesis and pharmacological evaluation of potent and highly selective D3 receptor ligands: inhibition of cocaine-seeking behaviour and the role of dopamine D3/D2 receptors. J Med Chem. 2003;46:3822–3838
  4. Witkin JM, Dijkstra D, Levant B, Akunne HC, Zapata A, Peters S, et al. Protection against cocaine toxicity in mice by the dopamine D3/D2 agonist R-(+)-trans-3,4a,10b-tetrahydro-4-propyl-2H,5H-[1]benzopyrano[4,3-b]-1,4-oxazin-9-ol [(+)-PD 128,907]. J Pharmacol Exp Ther. 2004;308:957–964
  5. Sokoloff P, Le Foll B, Perachon S, Bordet R, Ridray S, Schwartz JC. The dopamine D3 receptor and drug addiction. Neurotox Res. 2001;3:433–441
  6. Le Foll B, Schwartz JC, Sokoloff P. Disruption of nicotine conditioning by dopamine D3 receptor ligands. Mol Psychiatry. 2003;8:225–230
  7. Joyce JN, Millan MJ. Dopamine D3 receptor antagonists as therapeutic agents. Drug Discov Today. 2005;10:917–925
  8. Heidbreder CA, Gardner EL, Xi Z, Thanos PK, Mugnaini M, Hagan JJ, et al. The role of central dopamine D3 receptors in drug addiction: a review of pharmacological evidence. Brain Res Rev. 2005;49:77–105
  9. Hackling AH, Stark H. Dopamine D3 receptor ligands with antagonist properties. Chembiochem. 2002;3:946–961
  10. Mach RH, Huang Y, Freeman RA, Wu L, Vangveravong S, Luedtke RR. Conformationally-flexible benzamide analogues as dopamine D3 and sigma 2 receptor ligands. Bioorg Med Chem Lett. 2004;14:192–202
  11. Grundt P, Carlson EE, Cao J, Bennett CJ, McElveen E, Taylor M, et al. Novel heterocyclic trans olefin analogues of N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl}arylcarboxamides as selective probes with high affinity for the dopamine D3 receptor. J Med Chem. 2005;48:839–848
  12. Hackling A, Ghosh R, Perachon S, Mann A, Höltje HD, Wermuth CG, et al. N-(omega-(4-(2-methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as dopamine D2 and D3 receptor ligands. J Med Chem. 2003;46:3883–3899
  13. Dutta AK, Fei XS, Reith M. A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors. Bioorg Med Chem Lett. 2002;12:619–622
  14. Leopoldo M, Berardi F, Colabufo NA, De Giorgio P, Lacivita E, Perrone R, et al. Structure–affinity relationship study on N-[4-(4-arylpiperazin-1-yl)butyl]arylcarboxamides as potent and selective dopamine D3 receptor ligands. J Med Chem. 2002;45:5727–5735
  15. Newman AH, Cao J, Benett CJ, Robarge MJ, Freeman RA, Luedtke RR. N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl}arylcarboxamides as novel dopamine D3 receptor antagonists. Bioorg Med Chem Lett. 2003;13:2179–2183
  16. Chu W, Tu Z, McElveen E, Xu J, Taylor M, Luedtke RR, et al. Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem. 2005;13:77–87
  17. Bettinetti L, Schlotter K, Hübner H, Gmeiner P. Interactive SAR studies: rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists. J Med Chem. 2002;45:4594–4597
  18. Hocke C, Prante O, Löber S, Hübner H, Gmeiner P, Kuwert T. Synthesis and evaluation of 18F-labeled dopamine D3 receptor ligands as potential PET imaging agents. Bioorg Med Chem Lett. 2005;15:4819–4823
  19. Turolla EA, Matarrese M, Belloli S, Moresco RM, Simonelli P, Todde S, et al. 11C-labeling of N-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]arylcarboxamide derivatives and evaluation as potential radioligands for PET imaging of dopamine D3 receptors. J Med Chem. 2005;48:7018–7023
  20. Gao M, Mock BH, Hutchins GD, Zheng QH. Synthesis and initial PET imaging of new potential dopamine D3 receptor radioligands (E)-4,3,2-[11C]methoxy-N-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-cinnamoylamides. Bioorg Med Chem. 2005;13:6233–6343
  21. Langer O, Gulyas B, Sandell J, Laszlovszky I, Kiss B, Domany G, et al. Radiochemical labelling of the dopamine D3 receptor ligands RGH-1756. J Label Compd Radiopharm. 2000;43:1069–1074
  22. Hocke C, Prante O, Löber S, Hübner H, Gmeiner P, Kuwert T. Synthesis and radioiodination of selective ligands for the dopamine D3 receptor subtype. Bioorg Med Chem Lett. 2004;14:3963–3966
  23. Sovago J, Farde L, Halldin C, Langer O, Laszlovszky I, Kiss B, et al. Positron emission tomographic evaluation of the putative dopamine-D3 receptor ligand, [11C]RGH-1756 in the monkey brain. Neurochemistry International. 2004;45:609–617
  24. Pilla M, Perrachen S, Sautel F, Garrido F, Mann A, Wermuth CG, et al. Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. Nature. 1999;22:371–375
  25. Jewett D. A simple synthesis of [11C]methyl triflate. Appl Radiat Isot. 1992;43:1383–1385
  26. Någren K, Müller L, Halldin C, Swahn CG, Lehikoinen P. Improved synthesis of some commonly used PET radioligands by the use of [11C]methyl triflate. Nucl Med Biol. 1995;22:235–239
  27. Någren K, Halldin C, Müller L, Swahn CG, Lehikoinen P. Comparison of [11C]methyl triflate and [11C]methyl iodide in the synthesis of PET radioligands such as [11C]beta-CIT and [11C]beta-CFT. Nucl Med Biol. 1995;22:965–970
  28. Crouzel C, Langstrom B, Pike VW, Coenen H. Recommendations for a practical production of [11C]methyl iodide. Appl Radiat Isot. 1987;38:601–603
  29. Langer O, Någren K, Dollé F, Lundkvist C, Sandell J, Swahn CG, et al. Precursor synthesis and radiolabelling of the dopamine D2 receptor ligand [11C]raclopride from [11C]methyl triflate. J Label. Compd Radiopharm. 1999;42:1183–1193
  30. Sandell J, Langer O, Larsen P, Dollé F, Vaufrey F, Demphel S, et al. Improved specific radioactivity of the PET radioligand [11C]FLB 457 by use of the GE medical systems PETtrace MeI MicroLab. J Label Compd Radiopharm. 2000;43:331–338
  31. Dollé F, Bramoullé Y, Hinnen F, Fowler JS. Efficient synthesis and formulation of (R)-(−)-[11C]deprenyl, a selective radioligand for the quantification of MAO-B activity using PET. J Label Compd Radiopharm. 2002;45:803–811
  32. Dollé F, Valette H, Demphel S, Coulon C, Ottaviani M, Bottlaender M, et al. Radiosynthesis and in vivo evaluation of [11C]Ro-647312: a novel NR1/2B subtype selective NMDA receptor radioligand. J Label Compd Radiopharm. 2004;47:911–920
  33. Dollé F, Bottlaender M, Demphel S, Emond P, Fuseau C, Coulon C, et al. Highly efficient synthesis of [11C]PE2I, a selective radioligand for the quantification of the dopamine transporter using PET. J Label Compd Radiopharm. 2000;43:997–1004
  34. Lemaire C, Plenevaux A, Aerts J, Del Fiore G, Brihaye C, Le Bars D, et al. Solid phase extraction — an alternative to the use of rotary evaporators for solvent removal in the rapid formulation of PET radiopharmaceuticals. J Label Compd Radiopharm. 1999;42:63–75
  35. Joyce JN. Dopamine D3 receptor as a therapeutic target for antipsychotic and antiparkinsonian drugs. Pharmacol Ther. 2001;90:231–259
  36. Levant B. Differential distribution of D3 dopamine receptors in the brains of several mammalian species. Brain Res. 1998;3:269–274
  37. Bancroft GN, Morgan KA, Flietstra RJ, Levant B. Binding of [3H]PD128907, a putatively selective ligand for the D3 dopamine receptor, in rat brain: a receptor binding and quantitative autoradiography study. Neuropsychopharmacol. 1998;18:305–316
  38. Ding YS, Fowler J. New-generation radiotracers for nAChR and NET. Nucl Med Biol. 2005;32:707–718
  39. Zhang MR, Haradahira T, Maeda J, Okauchi T, Kawabe K, Noguchi J, et al. Syntheses and pharmacological evaluation of two potent antagonists for dopamine D4 receptors: [11C]YM-50001 and N-[2-[4-(4-chlorophenyl)-piperizin-1-yl]ethyl]-3-[11C]methoxybenzamide. Nucl Med Biol. 2002;29:233–241
  40. Levesque D, Diaz J, Pilon C, Martres MP, Giros B, Souil E, et al. Identification, characterization, and localization of the dopamine D3 receptor in rat brain using 7-[3H]hydroxy-N,N-di-n-propyl-2-aminotetralin. Proc Natl Acad Sci U S A. 1992;89:8155–8159
  41. Schotte A, Janssen PF, Bonaventure P, Leysen JE. Endogenous dopamine limits the binding of antipsychotic drugs to D3 receptors in the rat brain: a quantitative autoradiographic study. Histochem J. 1996;28:791–799
  42. Ginovart N, Farde L, Halldin C, Swahn CG. Effect of reserpine-induced depletion of synaptic dopamine on [11C]raclopride binding to D2-dopamine receptors in the monkey brain. Synapse. 1997;25:321–325
  43. Levant B. Differential sensitivity of [3H]7-OH-DPAT-labeled binding sites in rat brain to inactivation by N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. Brain Res. 1995;6:146–154
  44. Staelens L, Oltenfreiter R, Dumont F, Waterhouse RN, Vandenbulcke K, Blanckaert P, et al. In vivo evaluation of [123I]-4-iodo-N(4-(4-(2-methoxyphenyl)-piperazin-1-yl)butyl-benzamide: a potential sigma receptor ligand for SPECT studies. Nucl Med Biol. 2005;32:193–200

PII: S0969-8051(06)00098-9

doi: 10.1016/j.nucmedbio.2006.05.007

Nuclear Medicine and Biology
Volume 33, Issue 6 , Pages 785-795 , August 2006

Article Tools

* Image Usage & Resolution