Nuclear Medicine and Biology
Volume 33, Issue 3 , Pages 311-316 , April 2006

Synthesis and evaluation of [125I]I-TSA as a brain nicotinic acetylcholine receptor α7 subtype imaging agent

  • Mikako Ogawa

      Affiliations

    • Laboratory of Genome Bio-Photonics, Photon Medical Research Center, Hamamatsu Medical University, Hamamatsu 431-3192, Japan
  • ,
  • Ryo Tatsumi

      Affiliations

    • Pharmaceuticals Research Unit, Research & Development Division, Mitsubishi Pharma Corporation, Yokohama 227-0033, Japan
  • ,
  • Masakazu Fujio

      Affiliations

    • Pharmaceuticals Research Unit, Research & Development Division, Mitsubishi Pharma Corporation, Yokohama 227-0033, Japan
  • ,
  • Jiro Katayama

      Affiliations

    • Pharmaceuticals Research Unit, Research & Development Division, Mitsubishi Pharma Corporation, Yokohama 227-0033, Japan
  • ,
  • Yasuhiro Magata

      Affiliations

    • Laboratory of Genome Bio-Photonics, Photon Medical Research Center, Hamamatsu Medical University, Hamamatsu 431-3192, Japan
    • Corresponding Author InformationCorresponding author. Tel.: +81 53 435 2398; fax: +81 53 435 2398.

Received 9 November 2005 ,Revised 20 December 2005 ,Accepted 26 December 2005.

References 

  1. Karlin A, Akabas MH. Toward a structural basis for the function of nicotinic acetylcholine receptors and their cousins. Neuron. 1995;15:1231–1244
  2. 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
  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. Davies AR, Hardick DJ, Blagbrough IS, Potter BV, Wolstenholme AJ, Wonnacott S. Characterisation of the binding of [3H]methyllycaconitine: a new radioligand for labelling alpha7-type neuronal nicotinic acetylcholine receptors. Neuropharmacology. 1999;38:679–690
  6. 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
  7. 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
  8. 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
  9. Espinoza-Fonseca LM. Molecular docking of four beta-amyloid1-42 fragments on the alpha7 nicotinic receptor: delineating the binding site of the Abeta peptides. Biochem Biophys Res Commun. 2004;323:1191–1196
  10. Wang HY, Lee DH, D'Andrea MR, Peterson PA, Shank RP, Reitz AB. Beta-Amyloid(1–42) binds to alpha7 nicotinic acetylcholine receptor with high affinity. Implications for Alzheimer's disease pathology. J Biol Chem. 2000;275:5626–5632
  11. Martin LF, Kem WR, Freedman R. Alpha-7 nicotinic receptor agonists: potential new candidates for the treatment of schizophrenia. Psychopharmacology (Berl). 2004;174:54–64
  12. Jonnala RR, Buccafusco JJ. Relationship between the increased cell surface alpha7 nicotinic receptor expression and neuroprotection induced by several nicotinic receptor agonists. J Neurosci Res. 2001;66:565–572
  13. Dajas-Bailador FA, Lima PA, Wonnacott S. The alpha7 nicotinic acetylcholine receptor subtype mediates nicotine protection against NMDA excitotoxicity in primary hippocampal cultures through a Ca(2+) dependent mechanism. Neuropharmacology. 2000;39:2799–2807
  14. Kaneko S, Maeda T, Kume T, Kochiyama H, Akaike A, Shimohama S, et al. Nicotine protects cultured cortical neurons against glutamate-induced cytotoxicity via alpha7-neuronal receptors and neuronal CNS receptors. Brain Res. 1997;765:135–140
  15. Couturier S, Bertrand D, Matter JM, Hernandez MC, Bertrand S, Millar N, et al. A neuronal nicotinic acetylcholine receptor subunit (alpha 7) is developmentally regulated and forms a homo-oligomeric channel blocked by alpha-BTX. Neuron. 1990;5:847–856
  16. Ward JM, Cockcroft VB, Lunt GG, Smillie FS, Wonnacott S. Methyllycaconitine: a selective probe for neuronal alpha-bungarotoxin binding sites. FEBS Lett. 1990;270:45–48
  17. Navarro HA, Zhong D, Abraham P, Xu H, Carroll FI. Synthesis and pharmacological characterization of [(125)I]iodomethyllycaconitine ([(125)I]iodo-MLA). A new ligand for the alpha(7) nicotinic acetylcholine receptor. J Med Chem. 2000;43:142–145
  18. James RW, Bersinger NA, Schwendimann B, Fulpius BW. Characterization of iodinated derivatives of alpha-bungarotoxin. Hoppe Seyler Z Physiol Chem. 1980;361:1517–1524
  19. 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
  20. Ortells MO, Lunt GG. Evolutionary history of the ligand-gated ion-channel superfamily of receptors. Trends Neurosci. 1995;18:121–127
  21. Tatsumi R, Fujio M, Satoh H, Katayama J, Takanashi S, Hashimoto K, et al. Discovery of the alpha7 nicotinic acetylcholine receptor agonists. (R)-3′-(5-Chlorothiophen-2-yl)spiro-1-azabicyclo[2.2.2]octane-3,5′-[1′,3′] oxazolidin-2′-one as a novel, potent, selective, and orally bioavailable ligand. J Med Chem. 2005;48:2678–2686
  22. 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
  23. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951;193:265–275
  24. 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
  25. Boess FG, Steward LJ, Steele JA, Liu D, Reid J, Glencorse TA, et al. Analysis of the ligand binding site of the 5-HT3 receptor using site directed mutagenesis: importance of glutamate 106. Neuropharmacology. 1997;36:637–647
  26. 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
  27. Waterhouse RN. Determination of lipophilicity and its use as a predictor of blood–brain barrier penetration of molecular imaging agents. Mol Imaging Biol. 2003;5:376–389

PII: S0969-8051(05)00306-9

doi: 10.1016/j.nucmedbio.2005.12.016

Nuclear Medicine and Biology
Volume 33, Issue 3 , Pages 311-316 , April 2006