Table of Contents
International Journal of Molecular Imaging
Volume 2014, Article ID 507012, 10 pages
http://dx.doi.org/10.1155/2014/507012
Research Article

Ex Vivo Characterization of a Novel Iodine-123-Labelled Aminomethylchroman as a Potential Agonist Ligand for SPECT Imaging of Dopamine D2/3 Receptors

1Department of Nuclear Medicine, Academic Medical Center, University of Amsterdam, Meibergdreef 9, 1105 AZ Amsterdam, Netherlands
2SyMO-Chem BV, Den Dolech 2, 5612 AZ Eindhoven, Netherlands
3GE Healthcare, De Rondom 8, 5612 AP Eindhoven, Netherlands
4Department of Pharmacology, Johannes Gutenberg University, Obere Zahlbacher Straße 67, 55101 Mainz, Germany
5Department of Nuclear Medicine and Molecular Imaging, University Medical Center Groningen, University of Groningen, Hanzeplein 1, 9713 GZ Groningen, Netherlands

Received 29 July 2014; Revised 18 November 2014; Accepted 27 November 2014; Published 25 December 2014

Academic Editor: Adriaan A. Lammertsma

Copyright © 2014 Jan-Peter van Wieringen 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. 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
  2. S. Kapur and D. Mamo, “Half a century of antipsychotics and still a central role for dopamine D2 receptors,” Progress in Neuro-Psychopharmacology and Biological Psychiatry, vol. 27, no. 7, pp. 1081–1090, 2003. View at Publisher · View at Google Scholar · View at Scopus
  3. N. D. Volkow, J. S. Fowler, G.-J. Wang, and J. M. Swanson, “Dopamine in drug abuse and addiction: results from imaging studies and treatment implications,” Molecular Psychiatry, vol. 9, no. 6, pp. 557–569, 2004. View at Publisher · View at Google Scholar · View at Scopus
  4. S. von Campenhausen, B. Bornschein, R. Wick et al., “Prevalence and incidence of Parkinson's disease in Europe,” European Neuropsychopharmacology, vol. 15, no. 4, pp. 473–490, 2005. View at Publisher · View at Google Scholar · View at Scopus
  5. R. B. Goldstein, D. A. Dawson, S. Patricia Chou, and B. F. Grant, “Sex differences in prevalence and comorbidity of alcohol and drug use disorders: results from wave 2 of the national epidemiologic survey on alcohol and related conditions,” Journal of Studies on Alcohol and Drugs, vol. 73, no. 6, pp. 938–950, 2012. View at Google Scholar · View at Scopus
  6. J. C. Stoof and J. W. Kebabian, “Opposing roles for D-1 and D-2 dopamine receptors in efflux of cyclic AMP from rat neostriatum,” Nature, vol. 294, no. 5839, pp. 366–368, 1981. View at Publisher · View at Google Scholar · View at Scopus
  7. P. G. Strange, “New insights into dopamine receptors the central nervous system,” Neurochemistry International, vol. 22, no. 3, pp. 223–236, 1993. View at Publisher · View at Google Scholar · View at Scopus
  8. D. R. Sibley, A. de Lean, and I. Creese, “Anterior pituitary dopamine receptors. Demonstration of interconvertible high and low affinity states of the D-2 dopamine receptor,” Journal of Biological Chemistry, vol. 257, no. 11, pp. 6351–6361, 1982. View at Google Scholar · View at Scopus
  9. C. L. Chio, M. E. Lajiness, and R. M. Huff, “Activation of heterologously expressed D3 dopamine receptors: comparison with D2 dopamine receptors,” Molecular Pharmacology, vol. 45, no. 1, pp. 51–60, 1994. View at Google Scholar · View at Scopus
  10. P. Seeman, D. Weinshenker, R. Quirion et al., “Dopamine supersensitivity correlates with D2High states, implying many paths to psychosis,” Proceedings of the National Academy of Sciences of the United States of America, vol. 102, no. 9, pp. 3513–3518, 2005. View at Publisher · View at Google Scholar · View at Scopus
  11. J.-P. Van Wieringen, J. Booij, V. Shalgunov, P. Elsinga, and M. C. Michel, “Agonist high- and low-affinity states of dopamine D2 receptors: methods of detection and clinical implications,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 386, no. 2, pp. 135–154, 2013. View at Publisher · View at Google Scholar · View at Scopus
  12. N. R. Zahniser and P. B. Molinoff, “Effect of guanine nucleotides on striatal dopamine receptors,” Nature, vol. 275, no. 5679, pp. 453–455, 1978. View at Publisher · View at Google Scholar · View at Scopus
  13. P. Seeman, J. Schwarz, J.-F. Chen et al., “Psychosis pathways converge via D2High dopamine receptors,” Synapse, vol. 60, no. 4, pp. 319–346, 2006. View at Publisher · View at Google Scholar · View at Scopus
  14. S. R. George, M. Watanabe, and P. Seeman, “Dopamine D2 receptors in the anterior pituitary: a single population without reciprocal antagonist/agonist states,” Journal of Neurochemistry, vol. 44, no. 4, pp. 1168–1177, 1985. View at Publisher · View at Google Scholar · View at Scopus
  15. S. J. Finnema, B. Bang-Andersen, H. V. Wikström, and C. Halldin, “Current state of agonist radioligands for imaging of brain dopamine D2/D3 receptors in vivo with positron emission tomography,” Current Topics in Medicinal Chemistry, vol. 10, no. 15, pp. 1477–1498, 2010. View at Publisher · View at Google Scholar · View at Scopus
  16. N. Ginovart, M. Willeit, P. Rusjan et al., “Positron emission tomography quantification of [11C]-(+)-PHNO binding in the human brain,” Journal of Cerebral Blood Flow & Metabolism, vol. 27, no. 4, pp. 857–871, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. R. Narendran, W. G. Frankle, N. S. Mason et al., “Positron emission tomography imaging of D2/3 agonist binding in healthy human subjects with the radiotracer [11C]-N-propyl- norapomorphine: preliminary evaluation and reproducibility studies,” Synapse, vol. 63, no. 7, pp. 574–584, 2009. View at Publisher · View at Google Scholar · View at Scopus
  18. T. Otsuka, H. Ito, C. Halldin et al., “Quantitative PET analysis of the dopamine D2 receptor agonist radioligand 11C-(R)-2-CH3O-N-n-propylnorapomorphine in the human brain,” Journal of Nuclear Medicine, vol. 50, no. 5, pp. 703–710, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. R. Narendran, N. S. Mason, C. M. Laymon et al., “A comparative evaluation of the dopamine D2/3 agonist radiotracer [11C](-)-N-propyl-norapomorphine and antagonist [11C]raclopride to measure amphetamine-induced dopamine release in the human striatum,” Journal of Pharmacology and Experimental Therapeutics, vol. 333, no. 2, pp. 533–539, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. P. Shotbolt, A. C. Tziortzi, G. E. Searle et al., “Within-subject comparison of [11C]-(+)-PHNO and [11C]raclopride sensitivity to acute amphetamine challenge in healthy humans,” Journal of Cerebral Blood Flow and Metabolism, vol. 32, no. 1, pp. 127–136, 2012. View at Publisher · View at Google Scholar · View at Scopus
  21. R. Narendran, D.-R. Hwang, M. Slifstein et al., “In vivo vulnerability to competition by endogenous dopamine: comparison of the D2 receptor agonist radiotracer (−)-N-[11C]propyl-norapomorphine ([11C]NPA) with the D2 receptor antagonist radiotracer [11C]-raclopride,” Synapse, vol. 52, no. 3, pp. 188–208, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. N. Ginovart, L. Galineau, M. Willeit et al., “Binding characteristics and sensitivity to endogenous dopamine of [11C]-(+)-PHNO, a new agonist radiotracer for imaging the high-affinity state of D2 receptors in vivo using positron emission tomography,” Journal of Neurochemistry, vol. 97, no. 4, pp. 1089–1103, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. S. J. Finnema, V. Stepanov, R. Nakao et al., “18F-MCL-524, an 18F-labeled dopamine D2 and D3 receptor agonist sensitive to dopamine: a preliminary PET study,” Journal of Nuclear Medicine, vol. 55, no. 7, pp. 1164–1170, 2014. View at Google Scholar
  24. J.-P. Van Wieringen, V. Shalgunov, H. M. Janssen et al., “Synthesis and characterization of a novel series of agonist compounds as potential radiopharmaceuticals for imaging dopamine D2/3 receptors in their high-affinity state,” Journal of Medicinal Chemistry, vol. 57, no. 2, pp. 391–410, 2014. View at Publisher · View at Google Scholar · View at Scopus
  25. R. E. Mewshaw, J. Kavanagh, G. Stack et al., “New generation dopaminergic agents. 1. Discovery of a novel scaffold which embraces the D2 agonist pharmacophore. Structure-activity relationships of a series of 2-(aminomethyl)chromans,” Journal of Medicinal Chemistry, vol. 40, no. 26, pp. 4235–4256, 1997. View at Publisher · View at Google Scholar · View at Scopus
  26. 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, pp. 183–190, 1997. View at Publisher · View at Google Scholar
  27. B. Kiss, F. Horti, and A. Bobok, “In vitro and in vivo comparison of [3H](+)-PHNO and [3H]raclopride binding to rat striatum and lobes 9 and 10 of the cerebellum: a method to distinguish dopamine D3 from D2 receptor sites: a method to distinguish dopamine D3 from D2 receptor sites,” Synapse, vol. 65, no. 6, pp. 467–478, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. R. J. J. Knol, K. de Bruin, J. de Jong, B. L. F. van Eck-Smit, and J. Booij, “In vitro and ex vivo storage phosphor imaging of short-living radioisotopes,” Journal of Neuroscience Methods, vol. 168, no. 2, pp. 341–357, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Laruelle, M. Slifstein, and Y. Huang, “Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography,” Molecular Imaging and Biology, vol. 5, no. 6, pp. 363–375, 2003. View at Publisher · View at Google Scholar · View at Scopus
  30. D. F. Wong and M. G. Pomper, “Predicting the success of a radiopharmaceutical for in vivo imaging of central nervous system neuroreceptor systems,” Molecular Imaging and Biology, vol. 5, no. 6, pp. 350–362, 2003. View at Publisher · View at Google Scholar · View at Scopus
  31. E. J. Cobos, E. D. Pozo, and J. M. Baeyens, “Irreversible blockade of sigma-1 receptors by haloperidol and its metabolites in guinea pig brain and SH-SY5Y human neuroblastoma cells,” Journal of Neurochemistry, vol. 102, no. 3, pp. 812–825, 2007. View at Publisher · View at Google Scholar · View at Scopus
  32. W. K. Kroeze, S. J. Hufeisen, B. A. Popadak et al., “H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs,” Neuropsychopharmacology, vol. 28, no. 3, pp. 519–526, 2003. View at Publisher · View at Google Scholar · View at Scopus
  33. R. N. Waterhouse, “Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents,” Molecular Imaging & Biology, vol. 5, no. 6, pp. 376–389, 2003. View at Publisher · View at Google Scholar · View at Scopus
  34. V. Shalgunov, J. P. van Wieringen, H. M. Janssen et al., “Synthesis and evaluation in rats of the dopamine D2/3 receptor agonist 18F-AMC20 as potential radioligand for PET,” Journal of Nuclear Medicine, 2014. View at Publisher · View at Google Scholar