The identification of nonpeptide neurotensin receptor partial agonists from the potent antagonist SR48692 using a calcium mobilization assay

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 5, 2009, Pages 1438-1441

  Thomas, James B ^a   Navarro, Hernán ^a   Warner, Keith R ^a   Gilmour, Brian ^a  

^a RTI INTERNATIONAL   (United States)

Author keywords

Antagonist; Neurotensin; Nonpeptide; Partial agonist

Indexed keywords

2 [[1 (7 CHLORO 4 QUINOLINYL) 5 (2,6 DIMETHOXYPHENYL) 3 PYRAZOLYL]CARBONYLAMINO] 2 ADAMANTANECARBOXYLIC ACID; ADAMANTANE DERIVATIVE; AMINO ACID; CHLOROQUINE; LEUCINE; NAPHTHALENE; NEUROTENSIN DERIVATIVE; NEUROTENSIN RECEPTOR; PYRAZOLE;

AGONIST; ARTICLE; CALCIUM MOBILIZATION; DRUG DETERMINATION; DRUG EFFECT; DRUG IDENTIFICATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PROTEIN FUNCTION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; CALCIUM SIGNALING; CHO CELLS; CRICETINAE; CRICETULUS; DOSE-RESPONSE RELATIONSHIP, DRUG; PROTEIN BINDING; PYRAZOLES; QUINOLINES; RECEPTORS, NEUROTENSIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60449091853     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.01.024     Document Type: Article

References (36)

1. Roehr B. BMJ 331 (2005) 476
2. Caraway R., and Leeman S.E. J. Biol. Chem. 248 (1973) 6854
3. Quirion R., Rowe W.B., Lapchak P.A., Araujo D.M., and Beaudet A. Ann. N.Y. Acad. Sci. 668 (1992) 109
4. Sarret P., Perron A., Stroh T., and Beaudet A. J. Comp. Neurol. 461 (2003) 520
5. Uhl G.R. Ann. N.Y. Acad. Sci. 400 (1982) 132
6. Walker N., Lepee-Lorgeoux I., Fournier J., Betancur C., Rostene W., Ferrara P., and Caput D. Brain Res. Mol. Brain Res. 57 (1998) 193
7. Hokfelt T., Everitt B.J., Theodorsson-Norheim E., and Goldstein M. J. Comp. Neurol. 222 (1984) 543
8. Kalivas P.W., and Miller J.S. Brain Res. 300 (1984) 157
9. Kalivas P.W., Nemeroff C.B., and Prange Jr. A.J. Eur. J. Pharmacol. 78 (1982) 471
10. Ford A.P., and Marsden C.A. Brain Res. 534 (1990) 243
11. Nemeroff C.B., Hernandez D.E., Luttinger D., Kalivas P.W., and Prange Jr. A.J. Ann. N.Y. Acad. Sci. 400 (1982) 330
12. Lee K., Kim Y., Kim A.M., Helmin K., Nairn A.C., and Greengard P. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 3399
13. Matsuyama S., Fukui R., Higashi H., and Nishi A. Eur. J. Neurosci. 18 (2003) 1247
14. Matsuyama S., Higashi H., Maeda H., Greengard P., and Nishi A. J. Neurochem. 81 (2002) 325
15. Binder E.B., Kinkead B., Owens M.J., and Nemeroff C.B. Biol. Psychiatry 50 (2001) 856
16. Kitabgi P. Curr. Opin. Drug Discov. Dev. 5 (2002) 764
17. Tanaka K., Masu M., and Nakanishi S. Neuron 4 (1990) 847
18. Vita N., Laurent P., Lefort S., Chalon P., Dumont X., Kaghad M., Gully D., Le Fur G., Ferrara P., and Caput D. FEBS Lett. 317 (1993) 139
19. Chalon P., Vita N., Kaghad M., Guillemot M., Bonnin J., Delpech B., Le Fur G., Ferrara P., and Caput D. FEBS Lett. 386 (1996) 91
20. Mazella J., Botto J., Guillemare E., Coppola T., Sarret P., and Vincent J.P. J. Neurosci. 16 (1996) 5613
21. Petersen C.M., Nielsen M.S., Nykjaer A., Jacobsen L., Tommerup N., Rasmussen H.H., Roigaard H., Gliemann J., Madsen P., and Moestrup S.K. J. Biol. Chem. 272 (1997) 3599
22. Mazella J., Zsurger N., Navarro V., Chabry J., Kaghad M., Caput D., Ferrara P., Vita N., Gully D., Maffrand J.P., and Vincent J.P. J. Biol. Chem. 273 (1998) 26273
23. Gully D., Canton M., Boigegrain R., Jeanjean F., Molimard J., Poncelet M., Gueudet C., Heaulme M., Leyris R., Brouard A., Pelaprat D., Labbe-Jullie C., Mazella J., Soubrie P., Maffrand J.P., Rostene W., Kitabgi P., and Le Fur G. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 65
24. Gully D., Labeeuw B., Boigegrain R., Oury-Donat F., Bachy A., Poncelet M., Steinberg R., Suaud-Chagny M.F., Santucci V., Vita N., Pecceu F., Labbe-Jullie C., Kitabgi P., Soubrie P., Le Fur G., and Maffrand J.P. J. Pharmacol. Exp. Ther. 280 (1997) 802
25. Hong F., Zaidi J., Cusack B., and Richelson E. Bioorg. Med. Chem. 10 (2002) 3849
26. Richard F., Barroso S., Martinez J., Labbe-Jullie C., and Kitabgi P. Mol. Pharmacol. 60 (2001) 1392
27. Barroso S., Richard F., Nicolas-Etheve D., Reversat J.L., Bernassau J.M., Kitabgi P., and Labbe-Jullie C. J. Biol. Chem. 275 (2000) 328
28. Labbe-Jullie C., Barroso S., Delphine N., Reversat J., Botto J., Mazella J., Bernassau J., and Kitabgi P. J. Biol. Chem. 273 (1998) 16351
29. Labbe-Jullie C., Barroso S., Nicolas-Eteve D., Reversat J.L., Botto J.M., Mazella J., Bernassau J.M., and Kitabgi P. J. Biol. Chem. 273 (1998) 16351
30. Pang Y., Cusack B., Groshan K., and Richelson E. J. Biol. Chem. 271 (1996) 15060
31. Labeeuw, B.; Gully, D.; Jeanjean, F.; Molimard, J.-C.; Boigegrain, R. WO/1996/032382, 1996.
32. 3) δ 8.8 (d, 1H, J = 4.72 Hz), 8.14 (d, 1H, J = 1.81 Hz), 7.95 (d, 1H, J = 9.1), 7.5 (dd, 1H, J = 1.89 and 9.1 Hz), 7.4 (d, 1H, J = 7.95 Hz), 7.20 (t, 1H, J = 8.42 Hz), 7.10 (s, 1H), 7.08 (d, 1H, J = 4.72 Hz), 6.38 (d, 2H, J = 8.42 Hz), 4.81 (br s, 1H), 3.39 (s, 6H), 1.74 (m, 3H), 0.96 (dd, 6H, J = 5.49 and 10.21 Hz).
33. 50 values were determined from 10-point half-log concentration-response curves.
34. 50 values were determined using Prism (v 5.0, Graph Pad, San Diego, CA).
35. Quéré L., Boigegrain R., Jeanjean F., Gully D., Evrard G., and Durant F. J. Chem. Soc., Perkin Trans. 2 (1996) 2639
36. Fan Y., Lai M.H., Sullivan K., Popiolek M., Andree T.H., Dollings P., and Pausch M.H. Bioorg. Med. Chem. Lett. 18 (2008) 5789