Synthesis and in vitro evaluation of 18F-labelled S-fluoroalkyl diarylguanidines: Novel high-affinity NMDA receptor antagonists for imaging with PET

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 5, 2010, Pages 1749-1751

  Robins, Edward G ^a   Zhao, Yongjun ^a   Khan, Imtiaz ^b   Wilson, Anthony ^b   Luthra, Sajinder K ^a   Årstad, Erik ^a  

^a HAMMERSMITH HOSPITAL   (United Kingdom)

^b GE HEALTHCARE   (United Kingdom)

Author keywords

Fluorine 18; Glutamate; Imaging; NMDA; PET

Indexed keywords

FLUORODEOXYGLUCOSE F 18; GUANIDINE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; RADIOPHARMACEUTICAL AGENT;

ARTICLE; BINDING AFFINITY; DIAGNOSTIC IMAGING; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; ISOTOPE LABELING; LIPOPHILICITY; METHYLATION; POSITRON EMISSION TOMOGRAPHY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ANIMALS; BINDING SITES; FLUORINE RADIOISOTOPES; GUANIDINES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; SULFHYDRYL COMPOUNDS; SULFIDES;

EID: 76649143057     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.052     Document Type: Article

References (38)

1. Dingledine R., Borges K., Bowie D., and Traynelis S.F. Pharmacol. Rev. 51 (1999) 7
2. Lau C.G., and Zukin R.S. Nat. Rev. Neurosci. 8 (2007) 413
3. Kalia L.V., Kalia S.K., and Salter M.W. Lancet Neurol. 7 (2008) 742
4. Walters M.R., Bradford A.P., Fischer J., and Lees K.R. Br. J. Clin. Pharmacol. 53 (2002) 305
5. Gamzu E. Eur. Neuropsychopharm. 5 (1995) 171
6. Muir K.W., Grosset D.G., Gamzu E., and Lees K.R. Br. J. Clin. Pharmacol. 38 (1994) 33
7. Paoletti P., and Neyton J. Curr. Opin. Pharmacol. 7 (2007) 39
8. Cavara N.A., and Hollmann M. Mol. Neurobiol. 38 (2008) 16
9. Waterhouse R.N. Nucl. Med. Biol. 30 (2003) 869 and references therein
10. Kiesewetter D.O., Finn R.D., Rice K.C., and Monn J.A. Int. J. Rad. Appl. Instrum. [A] 41 (1990) 139
11. Andersson Y., Tyrefors N., Sihver S., Onoe H., Watanabe Y., Tsukada H., and Långström B. J. Label. Compd. Radiopharm. 41 (1998) 567
12. Brady F., Luthra S.K., and Pike V.W. Appl. Radiat. Isot. 40 (1989) 325
13. Brown D.R.P., Wyper D.J., Owens J., Patterson J., Kelly R.C., Hunter R., and McCulloch J. J. Psychiatr. Res. 31 (1997) 605
14. Owens J., Wyper D.J., Patterson J., Brown D.R.P., Elliott A.T., Teasdale G.M., and McCulloch J. Nucl. Med. Commun. 18 (1997) 149
15. Samnick S., Ametamey S., Leenders K.L., Vontobel P., Quack G., Parsons C.G., Neu H., and Schubiger P.A. Nucl. Med. Biol. 25 (1998) 323
16. Ametamey S.M., Bruehlmeier M., Kneifel S., Kokic M., Honer M., Arigoni M., Buck A., Burger C., Samnick S., Quack G., and Schubiger P.A. Nucl. Med. Biol. 29 (2002) 227
17. Shiue C.-Y., Vallabhahosula S., Wolf A.P., Dewey S.L., Fowler J.S., Schlyer D.J., Arnett C.D., and Zhou Y.-G. Nucl. Med. Biol. 24 (1997) 145
18. Haradahira T., Sasaki S., Maeda M., Kobayashi K., Inoue O., Tomita U., Nishikawa T., and Suzuki K. J. Label. Compd. Radiopharm. 41 (1998) 843
19. Orita K., Sasaki S., Maeda M., Hashimot A., Nishikawa T., Yugami T., and Umezu K. Nucl. Med. Biol. 20 (1993) 865
20. Sihver S., Sihver W., Andersson Y., Murata T., Bergström M., Onoe H., Matsumura K., Tsukada H., Oreland L., Långström B., and Watanabe Y. J. Neural Transm. 105 (1998) 117
21. Blin J., Denis A., Yamaguchi1 T., Crouzel1 C., MacKenzie E.T., and Baron J.C. Neurosci. Lett. 121 (1991) 183
22. Owens J., Tebbutt A.A., McGregor A.L., Kodama K., Magar S.S., Perlman M.E., Robins D.J., Durant G.J., and McCulloch J. Nucl. Med. Biol. 27 (2000) 557
23. Knol R.J.J., De Bruin K., Van Eck-Smit B.L.F., Pimlott S., Wyper D.J., and Booij J. Synapse 63 (2009) 557
24. Erlandsson K., Bressan R.A., Mulligan R.S., Gunn R.N., Cunningham V.J., Owens J., Wyper D., Ell P.J., and Pilowsky L.S. Nucl. Med. Biol. 30 (2003) 441
25. Stone J.M., Erlandsson K., Årstad E., Bressan R.A., Squassante L., Teneggi V., Ell P.J., and Pilowsky L.S. Nucl. Med. Biol. 33 (2006) 239
26. Stone J.M., Erlandsson K., Årstad E., Squassante L., Teneggi V., Bressan R.A., Krystal J.H., Ell P.J., and Pilowsky L.S. Psychopharmacology 197 (2008) 401
27. Zhao Y., Robins E.G., Turton D., Brady F., Luthra S.K., and Årstad E. J. Label. Compd. Radiopharm. 49 (2006) 163
28. Biegon A., Gibbs A., Alvarado M., Ono M., and Taylor S. Synapse 61 (2007) 577
29. Waterhouse R.N., Dumont F., Sultana A., Simpson N., and Laruelle M. J. Label. Compd. Radiopharm. 45 (2002) 955
30. Robins, E.G.; Arstad, E. Patent WO2006136846A1, 2006.
31. Bressan R.A., Erlandsson K., Mulligan R.S., Gunn R.N., Cunningham V.J., Owens J., Cullum I.D., Ell P.J., and Pilowsky L.S. Nucl. Med. Biol. 31 (2004) 155
32. Allert R. Chem. Ber. 14 (1881) 1434
33. Hu L.Y., Guo J., Magar S.S., Fischer J.B., Burke-Howie K.J., and Durant G.J. J. Med. Chem. 40 (1997) 4281
34. Simão D., Alves H., Belo D., Rabaça S., Lopes E.B., Santos I.C., Gama V., Duarte M.T., Henriques R.T., Novais H., and Almeida M. Eur. J. Inorg. Chem. (2001) 3119
35. In vitro ligand binding assays were performed by MDS Pharma Services Ltd, Taiwan. http://www.mdsps.com/.
36. Block D., Coenen H.H., and Stöcklin G. J. Label. Compd. Radiopharm. 25 (1988) 201
37. Neal T.R., Apana S., and Berridge M.S. J. Label. Compd. Radiopharm. 48 (2005) 557
38. 7.4) determination for compound 1 was performed by Syngene International Ltd following the method described by Mondal, S. K.; Mondal, N. B.; Banerjee, S.; Mazumder, U. K. Indian J. Pharmacol., 2009, 41, 176.