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Disease Markers
Volume 2015, Article ID 729698, 11 pages
http://dx.doi.org/10.1155/2015/729698
Research Article

Radiosynthesis, In Vivo Biological Evaluation, and Imaging of Brain Lesions with [123I]-CLINME, a New SPECT Tracer for the Translocator Protein

1Life Sciences Division, Australian Nuclear Science and Technology Organisation, New Illawarra Road, Lucas Heights, NSW 2234, Australia
2Department of Molecular Imaging, Royal Prince Alfred Hospital, Camperdown, NSW 2050, Australia
3CEA, DSV/I2BM, Service Hospitalier Frédéric Joliot, 4 Place du Général Leclerc, 91401 Orsay, France

Received 8 March 2015; Accepted 10 June 2015

Academic Editor: Ralf Lichtinghagen

Copyright © 2015 F. Mattner et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. V. Papadopoulos, M. Baraldi, T. R. Guilarte et al., “Translocator protein (18 kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function,” Trends in Pharmacological Sciences, vol. 27, no. 8, pp. 402–409, 2006. View at Publisher · View at Google Scholar · View at Scopus
  2. R. C. Brown and V. Papadopoulos, “Role of the peripheral-type benzodiazepine receptor in adrenal and brain steroidogenesis,” International Review of Neurobiology, vol. 46, pp. 117–143, 2001. View at Google Scholar · View at Scopus
  3. J. Benavides, D. Quarteronet, and F. Imbault, “Labeling of ‘peripheral-type’ benzodiazepine binding sites in the rat brain by using [3H]PK 11195, an isoquinoline carboxamide derivative: kinetic studies and autoradiographic localization,” Journal of Neurochemistry, vol. 41, no. 6, pp. 1744–1750, 1983. View at Publisher · View at Google Scholar · View at Scopus
  4. T. Funakoshi, S. Chaki, S. Okuyama et al., “In vivo receptor labeling of peripheral benzodiazepine receptor by ex vivo binding of [3H]PK11195,” Research Communications in Molecular Pathology and Pharmacology, vol. 105, no. 1-2, pp. 35–41, 1999. View at Google Scholar · View at Scopus
  5. R. B. Banati, “Visualising microglial activation in vivo,” Glia, vol. 40, no. 2, pp. 206–217, 2002. View at Publisher · View at Google Scholar · View at Scopus
  6. F. Mattner, D. L. Bandin, M. Staykova et al., “Evaluation of [123I]-CLINDE as a potent SPECT radiotracer to assess the degree of astroglia activation in cuprizone-induced neuroinflammation,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 38, no. 8, pp. 1516–1528, 2011. View at Publisher · View at Google Scholar · View at Scopus
  7. S. Venneti, B. J. Lopresti, and C. A. Wiley, “The peripheral benzodiazepine receptor (translocator protein 18 kDa) in microglia: from pathology to imaging,” Progress in Neurobiology, vol. 80, no. 6, pp. 308–322, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. A. L. Bartels, A. T. M. Willemsen, and K. L. Leenders, “[11C]-PK11195 PET: a monitor of anti-inflammatory treatment in Parkinson's disease?” NeuroImage, vol. 41, supplement 2, T108 pages, 2008. View at Publisher · View at Google Scholar
  9. G. W. Kreutzberg, “Microglia: a sensor for pathological events in the CNS,” Trends in Neurosciences, vol. 19, no. 8, pp. 312–318, 1996. View at Publisher · View at Google Scholar · View at Scopus
  10. F. Mattner, M. Staykova, P. Berghofer et al., “Central nervous system expression and PET imaging of the translocator protein in relapsing-remitting experimental autoimmune encephalomyelitis,” Journal of Nuclear Medicine, vol. 54, no. 2, pp. 291–298, 2013. View at Publisher · View at Google Scholar · View at Scopus
  11. F. Mattner, M. Staykova, P. Callaghan et al., “Assessment of neuroinflammation in transferred EAE via a translocator protein ligand,” in Experimental Autoimmune Encephalomyelitis—Models Disease Biology and Experimental Therapy, R. Weissert, Ed., pp. 47–64, InTech, Rijeka, Croatia, 2012. View at Google Scholar
  12. M. Hardwick, D. Fertikh, M. Culty, H. Li, B. Vidic, and V. Papadopoulos, “Peripheral-type benzodiazepine receptor (PBR) in human breast cancer: correlation of breast cancer cell aggressive phenotype with PBR expression, nuclear localization, and PBR-mediated cell proliferation and nuclear transport of cholesterol,” Cancer Research, vol. 59, no. 4, pp. 831–842, 1999. View at Google Scholar · View at Scopus
  13. F. Bono, I. Lamarche, V. Prabonnaud, G. Le Fur, and J. M. Herbert, “Peripheral benzodiazepine receptor agonists exhibit potent antiapoptotic activities,” Biochemical and Biophysical Research Communications, vol. 265, no. 2, pp. 457–461, 1999. View at Publisher · View at Google Scholar · View at Scopus
  14. H. Li, Z.-X. Yao, B. Degenhardt, G. Teper, and V. Papadopoulos, “Cholesterol binding at the cholesterol recognition/interaction amino acid consensus (CRAC) of the peripheral-type benzodiazepine receptor and inhibition of steroidogenesis by an HIV TAT-CRAC peptide,” Proceedings of the National Academy of Sciences of the United States of America, vol. 98, no. 3, pp. 1267–1272, 2001. View at Publisher · View at Google Scholar · View at Scopus
  15. P. Charbonneau, A. Syrota, C. Crouzel, J. M. Valois, and C. Prenant, “Peripheral-type benzodiazepine receptors in the living heart characterized by positron emission tomography,” Circulation, vol. 73, no. 3, pp. 476–483, 1986. View at Publisher · View at Google Scholar · View at Scopus
  16. D. L. Gildersleeve, T. Y. Lin, D. M. Wieland, B. J. Ciliax, J. M. Olson, and A. B. Young, “Synthesis of a high specific activity 125I-labeled analog of PK 11195, potential agent for SPECT imaging of the peripheral benzodiazepine binding site,” International Journal of Radiation Applications and Instrumentation B, vol. 16, pp. 423–429, 1989. View at Google Scholar
  17. D. L. Gildersleeve, M. E. van Dort, J. W. Johnson, P. S. Sherman, and D. M. Wieland, “Synthesis and evaluation of [123I]-Iodo-PK11195 for mapping peripheral-type benzodiazepine receptors (ω3) in heart,” Nuclear Medicine and Biology, vol. 23, no. 1, pp. 23–28, 1996. View at Publisher · View at Google Scholar · View at Scopus
  18. S. L. Pimlott, L. Stevenson, D. J. Wyper, and A. Sutherland, “Rapid and efficient radiosynthesis of [123I]I-PK11195, a single photon emission computed tomography tracer for peripheral benzodiazepine receptors,” Nuclear Medicine and Biology, vol. 35, no. 5, pp. 537–542, 2008. View at Publisher · View at Google Scholar · View at Scopus
  19. C. Pascali, S. K. Luthra, V. W. Pike et al., “The radiosynthesis of [18F]PK 14105 as an alternative radioligand for peripheral type benzodiazepine binding sites,” International Journal of Radiation Applications and Instrumentation, vol. 41, no. 5, pp. 477–482, 1990. View at Publisher · View at Google Scholar · View at Scopus
  20. M. Politis, N. Pavese, Y. F. Tai et al., “Microglial activation in regions related to cognitive function predicts disease onset in Huntington's disease: a multimodal imaging study,” Human Brain Mapping, vol. 32, no. 2, pp. 258–270, 2011. View at Publisher · View at Google Scholar · View at Scopus
  21. A. Schuitemaker, M. A. Kropholler, R. Boellaard et al., “Microglial activation in Alzheimer's disease: an (R)-[11C]PK11195 positron emission tomography study,” Neurobiology of Aging, vol. 34, no. 1, pp. 128–136, 2013. View at Publisher · View at Google Scholar · View at Scopus
  22. A. Thiel, B. A. Radlinska, C. Paquette et al., “The temporal dynamics of poststroke neuroinflammation: a longitudinal diffusion tensor imaging-guided PET study with 11C-PK11195 in acute subcortical stroke,” Journal of Nuclear Medicine, vol. 51, no. 9, pp. 1404–1412, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. A. Gerhard, R. B. Banati, G. B. Goerres et al., “[11C](R)-PK11195 PET imaging of microglial activation in multiple system atrophy,” Neurology, vol. 61, no. 5, pp. 686–689, 2003. View at Publisher · View at Google Scholar · View at Scopus
  24. F. Chauveau, H. Boutin, N. Van Camp, F. Dollé, and B. Tavitian, “Nuclear imaging of neuroinflammation: a comprehensive review of [11C]PK11195 challengers,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 35, no. 12, pp. 2304–2319, 2008. View at Publisher · View at Google Scholar · View at Scopus
  25. A. Damont, D. Roeda, and F. Dollé, “The potential of carbon-11 and fluorine-18 chemistry: illustration through the development of positron emission tomography radioligands targeting the translocator protein 18 kDa,” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 56, no. 3-4, pp. 96–104, 2013. View at Publisher · View at Google Scholar · View at Scopus
  26. E. Briard, S. S. Zoghbi, M. Imaizumi et al., “Synthesis and evaluation in monkey of two sensitive 11C-labeled aryloxyanilide ligands for imaging brain peripheral benzodiazepine receptors in vivo,” Journal of Medicinal Chemistry, vol. 51, no. 1, pp. 17–30, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. C. J. R. Fookes, T. Q. Pham, F. Mattner et al., “Synthesis and biological evaluation of substituted [18F] imidazo[1,2-a]pyridines and [18F]pyrazolo[1,5-a]pyrimidines for the study of the peripheral benzodiazepine receptor using positron emission tomography,” Journal of Medicinal Chemistry, vol. 51, no. 13, pp. 3700–3712, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. A. Takano, R. Arakawa, H. Ito et al., “Peripheral benzodiazepine receptors in patients with chronic schizophrenia: a PET study with [11C]DAA1106,” International Journal of Neuropsychopharmacology, vol. 13, no. 7, pp. 943–950, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. C. Thominiaux, F. Mattner, I. Greguric et al., “Radiosynthesis of 2-[6-chloro-2-(4-iodophenyl)imidazo[1,2-a]pyridin-3-yl]-N-ethyl-N-[11C]methyl-acetamide, [11C]CLINME, a novel radioligand for imaging the peripheral benzodiazepine receptors with PET,” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 50, no. 4, pp. 229–236, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. N. Van Camp, R. Boisgard, B. Kuhnast et al., “In vivo imaging of neuroinflammation: a comparative study between [18F]PBR111, [11C]CLINME and [11C]PK11195 in an acute rodent model,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 37, no. 5, pp. 962–972, 2010. View at Publisher · View at Google Scholar · View at Scopus
  31. H. Boutin, F. Chauveau, C. Thominiaux et al., “In vivo imaging of brain lesions with [11C]CLINME, a new PET radioligand of peripheral benzodiazepine receptors,” Glia, vol. 55, no. 14, pp. 1459–1468, 2007. View at Publisher · View at Google Scholar · View at Scopus
  32. A. Katsifis, F. Mattner, B. Dikic, and V. Papazian, “Synthesis of substituted [123I]imidazo[1,2-a]pyridines as potential probes for the study of the peripheral benzodiazepine receptors using SPECT,” Radiochimica Acta, vol. 88, no. 3-4, pp. 229–232, 2000. View at Google Scholar · View at Scopus
  33. A. Katsifis, F. Mattner, Z. Zhang, B. Dikic, and V. Papazian, “Synthesis of [123I]N′,N′-dimethyl-6-methyl-(4′-iodophenyl)imidazo[1,2-a]pyridine-3-acetamide for the study of peripheral benzodiazepine receptors using SPECT,” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 43, no. 4, pp. 385–394, 2000. View at Publisher · View at Google Scholar · View at Scopus
  34. F. Dumont, R. N. Waterhouse, J. A. Montoya et al., “Synthesis and in vivo evaluation of [11C]zolpidem, an imidazopyridine with agonist properties at central benzodiazepine receptors,” Nuclear Medicine and Biology, vol. 30, no. 4, pp. 435–439, 2003. View at Publisher · View at Google Scholar · View at Scopus
  35. F. Mattner, K. Mardon, C. Loc'h, and A. Katsifis, “Pharmacological evaluation of an [123I] labelled imidazopyridine-3-acetamide for the study of benzodiazepine receptors,” Life Sciences, vol. 79, no. 3, pp. 287–294, 2006. View at Publisher · View at Google Scholar · View at Scopus
  36. G. Paxinos and C. Watson, The Rat Brain in Stereotaxic Coordinates, Academic Press, New York, NY, USA, 4th edition, 1998.
  37. D. Riviere, D. Papadopoulos, C. Poupon et al., “A structural browser for human brain mapping,” NeuroImage, vol. 11, no. 5, p. S912, 2000. View at Publisher · View at Google Scholar · View at Scopus
  38. S. Z. Langer, S. Arbilla, J. Benavides, and B. Scatton, “Zolpidem and alpidem: two imidazopyridines with selectivity for w1- and w3-receptor subtypes,” Advances in Biochemical Psychopharmacology, vol. 46, pp. 61–72, 1990. View at Google Scholar
  39. J. Benavides, C. Malgouris, F. Imbault et al., “‘Peripheral type’ benzodiazepine binding sites in rat adrenals: binding studies with [3H]Pk 11195 and autoradiographic localization,” Archives Internationales de Pharmacodynamie et de Therapie, vol. 266, no. 1, pp. 38–49, 1983. View at Google Scholar · View at Scopus
  40. D. R. Gehlert, H. I. Yamamura, and J. K. Wamsley, “Autoradiographic localization of ‘peripheral-type’ benzodiazepine binding sites in the rat brain, heart and kidney,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 328, no. 4, pp. 454–460, 1985. View at Publisher · View at Google Scholar · View at Scopus
  41. R. R. H. Anholt, K. M. M. Murphy, G. E. Mack, and S. H. Snyder, “Peripheral-type benzodiazepine receptors in the central nervous system: localization to olfactory nerves,” The Journal of Neuroscience, vol. 4, no. 2, pp. 593–603, 1984. View at Google Scholar · View at Scopus
  42. D. M. Zisterer and D. C. Williams, “Peripheral-type benzodiazepine receptors,” General Pharmacology, vol. 29, no. 3, pp. 305–314, 1997. View at Publisher · View at Google Scholar · View at Scopus
  43. F. Mattner, K. Mardon, and A. Katsifis, “Pharmacological evaluation of [123I]-CLINDE: a radioiodinated imidazopyridine-3-acetamide for the study of peripheral benzodiazepine binding sites (PBBS),” European Journal of Nuclear Medicine and Molecular Imaging, vol. 35, no. 4, pp. 779–789, 2008. View at Publisher · View at Google Scholar · View at Scopus
  44. M.-R. Zhang, J. Maeda, K. Furutsuka et al., “[18F]FMDAA1106 and [18F]FEDAA1106: two positron-emitter labeled ligands for peripheral benzodiazepine receptor (PBR),” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 2, pp. 201–204, 2003. View at Publisher · View at Google Scholar · View at Scopus
  45. M.-R. Zhang, M. Ogawa, J. Maeda et al., “[2-11C]isopropyl-, [1-11C]ethyl-, and [11C]methyl-labeled phenoxyphenyl acetamide derivatives as positron emission tomography ligands for the peripheral benzodiazepine receptor: radiosynthesis, uptake, and in vivo binding in brain,” Journal of Medicinal Chemistry, vol. 49, no. 9, pp. 2735–2742, 2006. View at Publisher · View at Google Scholar · View at Scopus
  46. J. Doorduin, H. C. Klein, R. A. Dierckx, M. James, M. Kassiou, and E. F. J. de Vries, “[11C]-DPA-713 and [18F]-DPA-714 as new PET tracers for TSPO: a comparison with [11C]-(R)-PK11195 in a rat model of herpes encephalitis,” Molecular Imaging and Biology, vol. 11, no. 6, pp. 386–398, 2009. View at Publisher · View at Google Scholar · View at Scopus
  47. A. Cappelli, M. Matarrese, R. M. Moresco et al., “Synthesis, labeling, and biological evaluation of halogenated 2-quinolinecarboxamides as potential radioligands for the visualization of peripheral benzodiazepine receptors,” Bioorganic and Medicinal Chemistry, vol. 14, no. 12, pp. 4055–4066, 2006. View at Publisher · View at Google Scholar · View at Scopus
  48. H. Akiyama and P. L. McGeer, “Brain microglia constitutively express β-2 integrins,” Journal of Neuroimmunology, vol. 30, no. 1, pp. 81–93, 1990. View at Publisher · View at Google Scholar · View at Scopus
  49. P. Carayon, M. Portier, D. Dussossoy et al., “Involvement of peripheral benzodiazepine receptors in the protection of hematopoietic cells against oxygen radical damage,” Blood, vol. 87, no. 8, pp. 3170–3178, 1996. View at Google Scholar · View at Scopus