Reactive derivatives for affinity labeling in the ifenprodil site of NMDA receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 9, 2008, Pages 2765-2770

  Alarcon, Karine ^a   Martz, Adeline ^a   Mony, Laetitia ^b   Neyton, Jacques ^b   Paoletti, Pierre ^b   Goeldner, Maurice ^a   Foucaud, Bernard ^a  

^a CNRS   (France)

^b ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Ifenprodil; NMDA; NR2B

Indexed keywords

CYSTEINE; IFENPRODIL; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2B;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL REACTION; DRUG BINDING; DRUG INHIBITION; ELECTROPHYSIOLOGY;

ADRENERGIC ALPHA-ANTAGONISTS; AFFINITY LABELS; ANIMALS; BINDING SITES; BRAIN; CYSTEINE; ELECTROPHYSIOLOGY; MEMBRANE POTENTIALS; MODELS, CHEMICAL; PIPERIDINES; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 42949164549     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.04.019     Document Type: Article

References (33)

1. Cull-Candy S.G., Brickley S., and Farrant M. Curr. Opin. Neurobiol. 11 (2001) 32
2. Paoletti P., and Neyton J. Curr. Opin. Pharmacol. 7 (2007) 39
3. Chizh B.A., Headley P.M., and Tzschentke T.M. Trends Pharmacol. Sci. 22 (2001) 636
4. Parsons C.G. Eur. J. Pharmacol. 429 (2001) 71
5. Kemp J.A., and McKernan R.M. Nat. Neurosc. 5 (2002) 1039
6. Perin-Dureau F., Rachline J., Neyton J., and Paoletti P. J. Neurosci. 22 (2002) 5955
7. Malherbe P., Mutel V., Broger C., Perin-Dureau F., Kemp J.A., Neyton J., Paoletti P., and Kew J.N.C. J. Pharmacol. Exp. Ther. 307 (2003) 897
8. Chenard B.L., and Menniti F.S. Curr. Pharm. Des. 5 (1999) 381
9. Kornberg B.E., Nikam S.S., Wright J.L., Kesten S.R., Meltzer L.T., Coughenour L., Barr B., Serpa K.A., and McCormick J. Bioorg. Med. Chem. Lett. 5 (2004) 1213
10. Nikam S.S., and Meltzer L. Curr. Pharm. Des. 8 (2002) 845
11. Masuko T., Kashiwagi K., Kuno T., Nguyen N.D., Pahk A.J., Fukuchi J., Igarashi K., and Williams K. Mol. Pharmacol. 55 (1999) 957
12. Paoletti P., Perin-Dureau F., Fayyazuddin A., LeGoff A., Callebaut I., and Neyton J. Neuron 28 (2000) 911
13. Rachline J., Perin-Dureau F., Le Goff A., Neyton J., and Paoletti P. J. Neurosci. 25 (2005) 308
14. Herin G.A., and Aizenman E. Eur. J. Pharmacol. 500 (2004) 101
15. Hawkins L.M., Chazot P.L., and Stephenson F.A. Br. J. Pharmacol. 1p (1999) 126
16. Gallagher M.J., Huang H., Pritchett D.B., and Lynch D.R. J. Biol. Chem. 271 (1996) 9603
17. Wong E., Ng F.M., Yu C.Y., Lim P., Lim L.H., Traynelis S.F., and Low C.M. Protein Sci. 14 (2005) 2275
18. Foucaud B., Perret P., Grutter T., and Goeldner M. Trends Pharmacol. Sci. 22 (2001) 170
19. Foucaud B., Laube B., Schemm R., Goeldner M., and Betz H. J. Biol. Chem. 278 (2003) 24011
20. Kreimeyer A., Laube B., Sturgess M., Goeldner M., and Foucaud B. J. Med. Chem. 42 (1999) 4394
21. Furukawa H., and Gouaux E. EMBO J. 22 (2003) 2873
22. Foucaud B., Alarcon K., Sakr E., and Goeldner M. Curr. Chem. Biol. 1 (2007) 271
23. Tamiz A.P., Whittemore E.R., Zhou Z.L., Huang J.C., Drewe J.A., Chen J.C., Cai S.X., Weber E., Woodward R.M., and Keana J.F.W. J. Med. Chem. 41 (1998) 3499
24. Gershon H., Scala A., and Parmegiani R. J. Am. Chem. Soc. 8 (1965) 877
25. Cromwell N.H. J. Am. Chem. Soc. 68 (1946) 2634
26. Girreser U., Heber D., and Schütt M. Synthesis (1998) 715
27. Givens R.S., and Park C.-H. Tetrahedron Lett. 37 (1996) 6259
28. Imamura S., Nishikawa Y., Ichikawa T., Hattori T., Matsushita Y., Hashiguchi S., Kanzaki N., Iizawa Y., Baba M., and Sugihara Y. Bioorg. Med. Chem. 13 (2005) 397
29. HPLC retention time on a Analytical C18 Acclaim (4.6 × 300 mm) column using a 30 min linear gradient from 0% to 50% acetonitrile in 0.1% TFA water solution at 1 ml/min, for compounds 4 and 12, and 20 min similar linear gradient for compounds 8 and 9: 22.7, 25.5, 20.6 and 19.9 min, respectively. For compound 5, the linear gradient was as for compounds 4 and 12, except for the acetonitrile concentration, from 20% to 70%; retention time: 24.7 min.
30. Mutel V., Buchy D., Klingelschmidt A., Messer J., Bleuel Z., Kemp J.A., and Richards J.G. J. Neurochem. 70 (1998) 2147
31. Cheng Y.-C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
32. Avenet P., Léonardon J., Besnard F., Graham D., Frost J., Deporteere H., Langer S.Z., and Scatton B. Eur. J. Pharmacol. 296 (1996) 209
33. Williams K. Mol. Pharmacol. 44 (1993) 851