New iodinated quinoline-2-carboxamides for SPECT imaging of the translocator protein

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 954-957

  Stevenson, Louise ^a   Tavares, Adriana A S ^a   Brunet, Aurélie ^a   McGonagle, Fiona I ^a   Dewar, Deborah ^a   Pimlott, Sally L ^a   Sutherland, Andrew ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Heterocyclic synthesis; Imaging; Quinoline 2 carboxamides; SPECT; Translocator protein

Indexed keywords

AMIDE; BENZODIAZEPINE RECEPTOR BLOCKING AGENT; CONTRAST MEDIUM; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; N,N DIETHYL 3 IODOMETHYL 4 PHENYLQUINOLINE 2 CARBOXAMIDE; TRANSLOCATOR PROTEIN; UNCLASSIFIED DRUG; 4 AMINOBUTYRIC ACID A RECEPTOR; ANTINEOPLASTIC AGENT; BZRP PROTEIN, RAT; CARRIER PROTEIN; ISOQUINOLINE DERIVATIVE; PROTEIN BINDING; QUINOLINE DERIVATIVE; RADIOACTIVE IODINE;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG STABILITY; DRUG SYNTHESIS; IODINATION; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; ANIMAL; BRAIN; CHEMISTRY; COMPARATIVE STUDY; MALE; METABOLISM; PHYSIOLOGY; PROCEDURES; RAT; SCINTISCANNING;

ANIMALS; ANTINEOPLASTIC AGENTS; BRAIN; CARRIER PROTEINS; IODINE RADIOISOTOPES; ISOQUINOLINES; MALE; PROTEIN BINDING; QUINOLINES; RATS; RECEPTORS, GABA-A; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 74049152577     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.061     Document Type: Article

References (37)

1. Braestrup C., and Squires R. Proc. Natl. Acad. Sci. U.S.A. 74 (1977) 3805
2. Gavish M., Bachman I., Shoukrun R., Katz Y., Veenman L., Weisinger G., and Weizman A. Pharmacol. Rev. 51 (1999) 629
3. Papadopoulos V., Baraldi M., Guilarte T.R., Knudsen T.B., Lacapère J.J., Lindemann P., Norenberg M.D., Nutt D., Weizman A., Zhang M.R., and Gavish M. Trends Pharmacol. Sci. 27 (2006) 402
4. Scarf A.M., Ittner L.M., and Kassiou M. J. Med. Chem. 52 (2009) 581 and references therein
5. Wang M., Gao M., Hutchins G.D., and Zheng Q.-H. Eur. J. Med. Chem. 44 (2009) 2748
6. Benavides J., Fage D., Carter C., and Scatton B. Brain Res. 421 (1987) 167
7. Kuhlmann A.C., and Guilarte T.R. J. Neurochem. 74 (2000) 1694
8. Chen M.K., Baidoo K., Verina T., and Guilarte T.R. Brain 127 (2004) 1379
9. Maeda J., Ji B., Irie T., Tomiyama T., Maruyama M., Okauchi T., Staufenbiel M., Iwata N., Ono M., Saido T.C., Suzuki K., Mori H., Higuchi M., and Suhara T. J. Neurosci. 27 (2007) 10957
10. Venneti S., Wang G., Nguyen J., and Wiley C.A. J. Neuropathol. Exp. Neurol. 67 (2008) 1001
11. Yasuno F., Ota M., Kosaka J., Ito H., Higuchi M., Doronbekov T.K., Nozaki S., Fujimura Y., Koeda M., Asada T., and Suhara T. Biol. Psychiatry 64 (2008) 835
12. Imaizumi M., Kim H.J., Zoghbi S.S., Briard E., Hong J., Musachio J.L., Ruetzler C., Chuang D.M., Pike V.W., Innis R.B., and Fujita M. Neurosci. Lett. 411 (2007) 200
13. Rojas S., Martín A., Arranz M.J., Pareto D., Purroy J., Verdaguer E., Llop J., Gómez V., Gispert J.D., Millán O., Chamorro A., and Planas A.M. J. Cereb. Blood Flow Metab. 27 (2007) 1975
14. Chauveau F., Boutin H., Van Camp N., Dollé F., and Tavitian B. Eur. J. Nucl. Med. Mol. Imaging 35 (2008) 2304 and references therein
15. Yu W., Wang E., Voll R.J., Miller A.H., and Goodman M.M. Bioorg. Med. Chem. 16 (2008) 6145
16. Wang H., Pullambhatla M., Guilarte T.R., Mease R.C., and Pomper M.G. Biochem. Biophys. Res. Commun. 389 (2009) 80
17. Yanamoto K., Yamasaki T., Kumata K., Yui J., Odawara C., Kawamura K., Hatori A., Inoue O., Yamaguchi M., Suzuki K., and Zhang M.-R. Synapse 63 (2009) 961
18. Petit-Taboué M.-C., Baron J.-C., Barré L., Travére J.-M., Speckel D., Camsonne R., and MacKenzie E.T. Eur. J. Pharmacol. 200 (1991) 347
19. Shah F., Hume S.P., Pike V.W., Ashworth S., and McDermott J. Nucl. Med. Biol. 21 (1994) 573
20. Lockhart A., Davis B., Matthews J.C., Rahmoune H., Hong G., Gee A., Earnshaw D., and Brown J. Nucl. Med. Biol. 30 (2003) 199
21. Maeda J., Suhara T., Zhang M.-R., Okauchi T., Yasuno F., Ikoma Y., Inaji M., Nagai Y., Takano A., Obayashi S., and Suzuki K. Synapse 52 (2004) 283
22. Cappelli A., Anzini M., Vomero S., De Benedetti P.G., Menziani M.C., Giorgi G., and Manzoni C. J. Med. Chem. 40 (1997) 2910
23. Matarrese M., Moresco R.M., Cappelli A., Anzini M., Vomero S., Simonello P., Verza E., Magni F., Sudati F., Soloviev D., Todde S., Carpinelli A., Kienle M.G., and Fazio F. J. Med. Chem. 44 (2001) 579
24. Anzini M., Cappelli A., Vomero S., Seeber M., Menziani M.C., Langer T., Hagen B., Manzoni C., and Bourguignon J.-J. J. Med. Chem. 44 (2001) 1134
25. Cappelli A., Mohr G.P., Galleli A., Giuliani G., Anzini M., Vomero S., Fresta M., Porcu P., Maciocco E., Concas A., Biggio G., and Donati A. J. Med. Chem. 46 (2003) 3568
26. Cappelli A., Matarrese M., Moresco R.M., Valenti S., Anzini M., Vomero S., Turolla E.A., Belloli S., Simonelli P., Filannino M.A., Lecchi M., and Fazio F. Bioorg. Med. Chem. 14 (2006) 4055
27. Abbott P.A., Bonnert R.V., Caffrey M.V., Cage P.A., Cooke A.J., Donald D.K., Furber M., Hill S., and Withnall J. Tetrahedron 58 (2002) 3185
28. Stevenson L., Pimlott S.L., and Sutherland A. Tetrahedron Lett. 48 (2007) 7137
29. Ryabukhin S.V., Volochnyuk D.M., Plaskon A.S., Naumchik V.S., and Tolmachev A.A. Synthesis (2007) 1214
30. Anzini M., Cappelli A., and Vomero S. Heterocycles 38 (1994) 103
31. 3H]-PK11195 displacement assay was used for TSPO. See Supplementary data for full experimental details.
32. 50 value of 0.4 nM with TSPO. See Ref. 9e for details.
33. Valkó K., Bevan C., and Reynolds D. Anal. Chem. 69 (1997) 2022
34. Valkó K. J. Chromatogr., A 1037 (2004) 299
35. Valkó K. LCGC North America 25 (2007) 284
36. The log P value for CNS 1261, a known SPECT imaging agent for the NMDA receptor (Owens, J.; Tebbutt, A. A.; McGregor, A. L.; Kodama, K.; Magar, S. S.; Perlman, M. E.; Robins, D. J.; Durant, G. J.; McCulloch, J. Nucl. Med. Biol. 2000, 27, 557) was determined using our HPLC method and was found to be 4.94.
37. Compound 18 was incubated in phosphate buffered saline at 37 °C. The decomposition of 18 was then monitored using HPLC. Decomposition was only observed at around 24 h. See Supplementary data for full experimental details. A patient, on average is normally scanned 2-4 h after injection of a SPECT imaging agent.