Nuclear Medicine and Biology
Volume 37, Issue 3 , Pages 347-355 , April 2010

Synthesis and evaluation of new imaging agent for central nicotinic acetylcholine receptor α7 subtype

  • Mikako Ogawa

      Affiliations

    • Photon Medical Research Center, Hamamatsu University School of Medicine, Hamamatsu, Japan
    • ,
  • Shingo Nishiyama

      Affiliations

    • PET Center, Central Research Laboratory, Hamamatsu Photonics K.K., Hamamatsu, Japan
    • ,
  • Hideo Tsukada

      Affiliations

    • PET Center, Central Research Laboratory, Hamamatsu Photonics K.K., Hamamatsu, Japan
    • ,
  • Kentaro Hatano

      Affiliations

    • National Institute for Longevity Sciences, National Center for Geriatrics and Gerontology, Obu, Japan
    • ,
  • Takeshi Fuchigami

      Affiliations

    • Photon Medical Research Center, Hamamatsu University School of Medicine, Hamamatsu, Japan
    • ,
  • Hiroshi Yamaguchi

      Affiliations

    • National Institute for Longevity Sciences, National Center for Geriatrics and Gerontology, Obu, Japan
    • Molecular Imaging Frontier Research Center, Hamamatsu University School of Medicine, Hamamatsu, Japan
    • ,
  • Yoshitaka Matsushima

      Affiliations

    • Department of Chemistry, Hamamatsu University School of Medicine, Hamamatsu, Japan
    • ,
  • Kengo Ito

      Affiliations

    • National Institute for Longevity Sciences, National Center for Geriatrics and Gerontology, Obu, Japan
    • ,
  • Yasuhiro Magata

      Affiliations

    • Photon Medical Research Center, Hamamatsu University School of Medicine, Hamamatsu, Japan
    • Molecular Imaging Frontier Research Center, Hamamatsu University School of Medicine, Hamamatsu, Japan
    • Corresponding Author InformationCorresponding author. Laboratory of Genome Bio-Photonics, Photon Medical Research Center, Hamamatsu University School of Medicine, 1-20-1 Handayama, Higashi-ku, Hamamatsu 431-3192, Japan. Tel.: +81 53 435 2398: fax: +81 53 435 2398.

Received 21 October 2009 ,Revised 6 November 2009 ,Accepted 25 November 2009.

References 

  1. Patrick J, Sequela P, Vernino S, Amador M, Luetje C, Dani JA. Functional diversity of neuronal nicotinic acetylcholine receptors. Prog Brain Res. 1993;98:113–120
  2. Karlin A and Akabas MH. Toward a structural basis for the function of nicotinic.
  3. Gotti C, Fornasari D, Clementi F. Human neuronal nicotinic receptors. Prog Neurobiol. 1997;53:199–237
  4. Albuquerque EX, Alkondon M, Pereira EF, Castro NG, Schrattenholz A, Barbosa CT, et al. Properties of neuronal nicotinic acetylcholine receptors: pharmacological characterization and modulation of synaptic function. J Pharmacol Exp Ther. 1997;280:1117–1136
  5. Court J, Spurden D, Lloyd S, McKeith I, Ballard C, Cairns N, et al. Neuronal nicotinic receptors in dementia with Lewy bodies and schizophrenia: alpha-bungarotoxin and nicotine binding in the thalamus. J Neurochem. 1999;73:1590–1597
  6. Court J, Martin-Ruiz C, Piggott M, Spurden D, Griffiths M, Perry E. Nicotinic receptor abnormalities in Alzheimer's disease. Biol Psychiatry. 2001;49:175–184
  7. Martin-Ruiz CM, Haroutunian VH, Long P, Young AH, Davis KL, Perry EK, et al. Dementia rating and nicotinic receptor expression in the prefrontal cortex in schizophrenia. Biol Psychiatry. 2003;54:1222–1233
  8. James RW, Bersinger NA, Schwendimann B, Fulpius BW. Characterization of iodinated derivatives of alpha-bungarotoxin. Hoppe Seylers Z Physiol Chem. 1980;361:1517–1524
  9. Davies AR, Hardick DJ, Blagbrough IS, Potter BV, Wolstenholme AJ, Wonnacott S. Characterisation of the binding of [3H]methyllycaconitine: a new radioligand for labelling alpha 7-type neuronal nicotinic acetylcholine receptors. Neuropharmacology. 1999;38:679–690
  10. Navarro HA, Zhong D, Abraham P, Xu H, Carroll FI. Synthesis and pharmacological characterization of [125I]iodomethyllycaconitine ([125I]iodo-MLA). A new ligand for the alpha(7) nicotinic acetylcholine receptor. J Med Chem. 2000;43:142–145
  11. Pomper MG, Phillips E, Fan H, McCarthy DJ, Keith RA, Gordon JC, et al. Synthesis and biodistribution of radiolabeled alpha 7 nicotinic acetylcholine receptor ligands. J Nucl Med. 2005;46:326–334
  12. Ortells MO, Lunt GG. Evolutionary history of the ligand-gated ion-channel superfamily of receptors. Trends Neurosci. 1995;18:121–127
  13. Ogawa M, Tatsumi R, Fujio M, Katayama J, Magata Y. Synthesis and evaluation of [125I]I-TSA as a brain nicotinic acetylcholine receptor alpha7 subtype imaging agent. Nucl Med Biol. 2006;33:311–316
  14. Hashimoto K, Nishiyama S, Ohba H, Matsuo M, Kobashi T, Takahagi M, et al. [11C]CHIBA-1001 as a novel PET ligand for alpha7 nicotinic receptors in the brain: a PET study in conscious monkeys. PLoS One. 2008;3:e3231
  15. Deuther-Conrad W, Fischer S, Hiller A, Nielsen EO, Timmermann DB, Steinbach J, et al. Molecular imaging of alpha7 nicotinic acetylcholine receptors: design and evaluation of the potent radioligand [18F]NS10743. Eur J Nucl Med Mol Imaging. 2009;36:791–800
  16. Mukhin AG, Gundisch D, Horti AG, Koren AO, Tamagnan G, Kimes AS, et al. 5-Iodo-A-85380, an alpha4beta2 subtype-selective ligand for nicotinic acetylcholine receptors. Mol Pharmacol. 2000;57:642–649
  17. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951;193:265–275
  18. Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol. 1973;22:3099–3108
  19. Mullen G, Napier J, Balestra M, DeCory T, Hale G, Macor J, et al. (-)-Spiro[1-azabicyclo[2.2.2]octane-3,5′-oxazolidin-2′-one], a conformationally restricted analogue of acetylcholine, is a highly selective full agonist at the alpha 7 nicotinic acetylcholine receptor. J Med Chem. 2000;43:4045–4050
  20. Saji H, Iida Y, Nakatsuka I, Kataoka M, Ariyoshi K, Magata Y, et al. Radioiodinated 2′-iododiazepam: a potential imaging agent for SPECT investigations of benzodiazepine receptors. J Nucl Med. 1993;34:932–937
  21. Watanabe M, Okada H, Shimizu K, Omura T, Yoshikawa E, Kosugi T, et al. A high resolution animal PET scanner using compact PS-PMT detectors. IEEE. Trans. Nucl. Sci. 1997;44:1277–1282
  22. Kulak JM, Carroll FI, Schneider JS. [125I]Iodomethyllycaconitine binds to alpha7 nicotinic acetylcholine receptors in monkey brain. Eur J Neurosci. 2006;23:2604–2610
  23. Toyohara J, Sakata M, Wu J, Ishikawa M, Oda K, Ishii K, et al. Preclinical and the first clinical studies on [11C]CHIBA-1001 for mapping alpha7 nicotinic receptors by positron emission tomography. Ann Nucl Med. 2009;23:301–309
  24. Navarro HA, Xu H, Zhong D, Abraham P, Carroll FI. In vitro and in vivo characterization of [125I]iodomethyllycaconitine in the rat. Synapse. 2002;44:117–123
  25. Clarke PB, Schwartz RD, Paul SM, Pert CB, Pert A. Nicotinic binding in rat brain: autoradiographic comparison of [3H]acetylcholine, [3H]nicotine, and [125I]-alpha-bungarotoxin. J Neurosci. 1985;5:1307–1315
  26. Cimino M, Marini P, Fornasari D, Cattabeni F, Clementi F. Distribution of nicotinic receptors in cynomolgus monkey brain and ganglia: localization of alpha 3 subunit mRNA, alpha-bungarotoxin and nicotine binding sites. Neuroscience. 1992;51:77–86
  27. Court JA, Martin-Ruiz C, Graham A, Perry E. Nicotinic receptors in human brain: topography and pathology. J Chem Neuroanat. 2000;20:281–298
  28. Han ZY, Zoli M, Cardona A, Bourgeois JP, Changeux JP, Le Novere N. Localization of [3H]nicotine, [3H]cytisine, [3H]epibatidine, and [125I]alpha-bungarotoxin binding sites in the brain of Macaca mulatta. J Comp Neurol. 2003;461:49–60
  29. Kulak JM, Schneider JS. Differences in alpha7 nicotinic acetylcholine receptor binding in motor symptomatic and asymptomatic MPTP-treated monkeys. Brain Res. 2004;999:193–202
  30. Whiteaker P, Davies AR, Marks MJ, Blagbrough IS, Potter BV, Wolstenholme AJ, et al. An autoradiographic study of the distribution of binding sites for the novel alpha7-selective nicotinic radioligand [3H]-methyllycaconitine in the mouse brain. Eur J Neurosci. 1999;11:2689–2696

PII: S0969-8051(09)00287-X

doi: 10.1016/j.nucmedbio.2009.11.007

Nuclear Medicine and Biology
Volume 37, Issue 3 , Pages 347-355 , April 2010

Article Tools

* Image Usage & Resolution