Table of Contents
International Journal of Molecular Imaging
Volume 2011 (2011), Article ID 709416, 7 pages
http://dx.doi.org/10.1155/2011/709416
Research Article

Synthesis and In Vitro Evaluation of Novel Nortropane Derivatives as Potential Radiotracers for Muscarinic M2 Receptors

1Department of Nuclear Medicine, Medical Center Alkmaar, Wilhelminalaan 12, 1815 JD Alkmaar, The Netherlands
2Department of Organic Chemistry, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands
3GE Healthcare, Cygne Center, De Rondom 8, 5612 AP Eindhoven, The Netherlands
4Department of Nuclear Medicine, Academic Medical Center, University of Amsterdam, Meibergdreef 9, 1105 AZ Amsterdam, The Netherlands

Received 24 November 2010; Revised 3 March 2011; Accepted 25 March 2011

Academic Editor: Guy Bormans

Copyright © 2011 Remco J. J. Knol 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. D. C. Mash, D. D. Flynn, and L. T. Potter, “Loss of M2 muscarine receptors in the cerebral cortex in Alzheimer's disease and experimental cholinergic denervation,” Science, vol. 228, no. 4703, pp. 1115–1117, 1985. View at Google Scholar · View at Scopus
  2. P. Tiraboschi, L. A. Hansen, M. Alford et al., “Cholinergic dysfunction in diseases with LEWY bodies,” Neurology, vol. 54, no. 2, pp. 407–411, 2000. View at Google Scholar · View at Scopus
  3. D. S. Baskin, J. L. Browning, F. J. Pirozzolo, S. Korporaal, J. A. Baskin, and S. H. Appel, “Brain choline acetyltransferase and mental function in Alzheimer disease,” Archives of Neurology, vol. 56, no. 9, pp. 1121–1123, 1999. View at Publisher · View at Google Scholar · View at Scopus
  4. J. L. W. Bosboom, D. Stoffers, and E. C. Wolters, “Cognitive dysfunction and dementia in Parkinson's disease,” Journal of Neural Transmission, vol. 111, no. 10-11, pp. 1303–1315, 2004. View at Publisher · View at Google Scholar · View at Scopus
  5. E. K. Perry, M. Curtis, and D. J. Dick, “Cholinergic correlates of cognitive impairment in Parkinson's disease: comparisons with Alzheimer's disease,” Journal of Neurology Neurosurgery and Psychiatry, vol. 48, no. 5, pp. 413–421, 1985. View at Google Scholar
  6. J. M. Candy, R. H. Perry, and E. K. Perry, “Pathological changes in the nucleus of Meynert in Alzheimer's and Parkinson's diseases,” Journal of the Neurological Sciences, vol. 59, no. 2, pp. 277–289, 1983. View at Publisher · View at Google Scholar
  7. J. T. Coyle, D. L. Price, and M. R. DeLong, “Alzheimer's disease: a disorder of cortical cholinergic innervation,” Science, vol. 219, no. 4589, pp. 1184–1190, 1983. View at Google Scholar · View at Scopus
  8. I. Aubert, D. M. Araujo, D. Cecyre, Y. Robitaille, S. Gauthier, and R. Quirion, “Comparative alterations of nicotinic and muscarinic binding sites in Alzheimer's and Parkinson's diseases,” Journal of Neurochemistry, vol. 58, no. 2, pp. 529–541, 1992. View at Google Scholar · View at Scopus
  9. S. T. Rouse, S. M. Edmunds, H. Yi, M. L. Gilmor, and A. I. Levey, “Localization of M2 muscarinic acetylcholine receptor protein in cholinergic and non-cholinergic terminals in rat hippocampus,” Neuroscience Letters, vol. 284, no. 3, pp. 182–186, 2000. View at Publisher · View at Google Scholar · View at Scopus
  10. D. O. Kiesewetter, J. Lee, L. Lang, S. G. Park, C. H. Paik, and W. C. Eckelman, “Preparation of 18F-labeled muscarinic agonist with M2 selectivity,” Journal of Medicinal Chemistry, vol. 38, no. 1, pp. 5–8, 1995. View at Google Scholar · View at Scopus
  11. M. Maziere, “Cholinergic neurotransmission studied in vivo using positron emission tomography or single photon emission computerized tomography,” Pharmacology and Therapeutics, vol. 66, no. 1, pp. 83–101, 1995. View at Publisher · View at Google Scholar · View at Scopus
  12. D. W. McPherson, D. L. DeHaven-Hudkins, A. P. Callahan, and F. F. Knapp, “Synthesis and biodistribution of iodine-125-labeled 1-azabicyclo[2.2.2]oct-3-yl α-hydroxy-α-(1-iodo-1-propen-3-yl)-α-phenylacetate. A new ligand for the potential imaging of muscarinic receptors by single photon emission computed tomography,” Journal of Medicinal Chemistry, vol. 36, no. 7, pp. 848–854, 1993. View at Google Scholar · View at Scopus
  13. D. O. Kiesewetter, R. E. Carson, E. M. Jagoda, P. Herscovitch, and W. C. Eckelman, “Using single photon emission tomography (SPECT) and positron emission tomography (PET) to trace the distribution of muscarinic acetylcholine receptor (MACHR) binding radioligands,” Life Sciences, vol. 64, no. 6-7, pp. 511–518, 1999. View at Publisher · View at Google Scholar · View at Scopus
  14. P. Sauerberg, P. H. Olesen, S. Nielsen et al., “Novel functional M1 selective muscarinic agonists. Synthesis and structure-activity relationships of 3-(1,2,5-thiadiazolyl)-1,2,5,6-tetrahydro-1-methylpyridines,” Journal of Medicinal Chemistry, vol. 35, no. 12, pp. 2274–2283, 1992. View at Google Scholar · View at Scopus
  15. L. Ravasi, D. O. Kiesewetter, K. Shimoji, G. Lucignani, and W. C. Eckelman, “Why does the agonist [18F]FP-TZTP bind preferentially to the M2 muscarinic receptor?” European Journal of Nuclear Medicine and Molecular Imaging, vol. 33, no. 3, pp. 292–300, 2006. View at Publisher · View at Google Scholar · View at Scopus
  16. R. M. Cohen, T. A. Podruchny, A. L. W. Bokde et al., “Higher in vivo muscarinic-2 receptor distribution volumes in aging subjects with an apolipoprotein E-ε4 allele,” Synapse, vol. 49, no. 3, pp. 150–156, 2003. View at Publisher · View at Google Scholar · View at Scopus
  17. T. A. Podruchny, C. Connolly, A. Bokde et al., “In vivo muscarinic 2 receptor imaging in cognitively normal young and older volunteers,” Synapse, vol. 48, no. 1, pp. 39–44, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. D. M. Cannon, J. K. Klaver, S. K. Gandhi et al., “Genetic variation in cholinergic muscarinic-2 receptor gene modulates M receptor binding in vivo and accounts for reduced binding in bipolar disorder,” Molecular Psychiatry, vol. 16, pp. 407–418, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. J. Booij, G. Tissingh, A. Winogrodzka, and E. A. Van Royen, “Imaging of the dopaminergic neurotransmission system using single-photon emission tomography and positron emission tomography in patients with parkinsonism,” European Journal of Nuclear Medicine, vol. 26, no. 2, pp. 171–182, 1999. View at Publisher · View at Google Scholar · View at Scopus
  20. M. H. Bourguignon, E. K. J. Pauwels, C. Loc'h, and B. Mazière, “Iodine-123 labelled radiopharmaceuticals and single-photon emission tomography: a natural liaison,” European Journal of Nuclear Medicine, vol. 24, no. 3, pp. 331–344, 1997. View at Publisher · View at Google Scholar · View at Scopus
  21. F. J. Diaz-Corrales, S. Sanz-Viedma, D. Garcia-Solis, T. Escobar-Delgado, and P. Mir, “Clinical features and I-FP-CIT SPECT imaging in drug-induced parkinsonism and Parkinson's disease,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 37, no. 3, pp. 556–564, 2010. View at Publisher · View at Google Scholar · View at Scopus
  22. N. A. Lassen, “A reappraisal of the relative merits of SPET and PET in the quantitation of neuroreceptors: the advantage of a longer half-life!,” European Journal of Nuclear Medicine, vol. 23, no. 1, pp. 1–4, 1996. View at Publisher · View at Google Scholar · View at Scopus
  23. S. A. Ross and J. P. Seibyl, “Research applications of selected 123I-labeled neuroreceptor SPECT imaging ligands,” Journal of Nuclear Medicine Technology, vol. 32, no. 4, pp. 209–214, 2004. View at Google Scholar
  24. S. Vallabhajosula, Molecular Imaging: Radiopharmaceuticals for PET and SPECT, Springer, Berlin, Germany, 2009.
  25. R. J. J. Knol, T. Doornbos, J. C. Van Den Bos et al., “Synthesis and evaluation of iodinated TZTP-derivatives as potential radioligands for imaging of muscarinic M receptors with SPET,” Nuclear Medicine and Biology, vol. 31, no. 1, pp. 111–123, 2004. View at Publisher · View at Google Scholar · View at Scopus
  26. K. Nobuhara, C. Halldin, H. Hall et al., “Z-IQNP: a potential radioligand for SPECT imaging of muscarinic acetylcholine receptors in Alzheimer's disease,” Psychopharmacology, vol. 149, no. 1, pp. 45–55, 2000. View at Google Scholar · View at Scopus
  27. X. F. Pei, T. H. Gupta, B. Badio, W. L. Padgett, and J. W. Daly, “6β-acetoxynortropane: a potent muscarinic agonist with apparent selectivity toward M-receptors,” Journal of Medicinal Chemistry, vol. 41, no. 12, pp. 2047–2055, 1998. View at Publisher · View at Google Scholar · View at Scopus
  28. R. Robinson, “A synthesis of tropinone,” Journal of the Chemical Society, Transactions, vol. 111, pp. 762–768, 1917. View at Publisher · View at Google Scholar · View at Scopus
  29. J. W. Boja, M. J. Kuhar, T. Kopajtic et al., “Secondary amine analogues of 3β-(4-substituted phenyl)tropane-2β-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters,” Journal of Medicinal Chemistry, vol. 37, no. 8, pp. 1220–1223, 1994. View at Google Scholar · View at Scopus
  30. M. Koreeda and J. Luengo, “A new reagent for the selective, high-yield N-dealkylation of tertiary amines: improved syntheses of naltrexone and nalbuphine,” Journal of Organic Chemistry, vol. 49, no. 11, pp. 2081–2082, 1984. View at Google Scholar
  31. J. Booij, G. Andringa, L. J. M. Rijks et al., “[123I]FP-CIT binds to the dopamine transporter as assessed by biodistribution studies in rats and SPECT studies in MPTP-lesioned monkeys,” Synapse, vol. 27, no. 3, pp. 183–190, 1997. View at Publisher · View at Google Scholar · View at Scopus
  32. J. L. Neumeyer, S. Wang, Y. Gao et al., “N-ω-fluoroalkyl analogs of (1R)-2β-carbomethoxy-3β-(4-iodophenyl)- tropane (β-CIT): radiotracers for positron emission tomography and single photon emission computed tomography imaging of dopamine transporters,” Journal of Medicinal Chemistry, vol. 37, no. 11, pp. 1558–1561, 1994. View at Publisher · View at Google Scholar · View at Scopus
  33. S. Wang, Y. Gao, M. Laruelle et al., “Enantioselectivity of cocaine recognition sites: binding of (1S)- and (1R)-2β-carbomethoxy-3β-(4-iodophenyl)tropane (β-CIT) to monoamine transporters,” Journal of Medicinal Chemistry, vol. 36, no. 13, pp. 1914–1917, 1993. View at Google Scholar · View at Scopus