Comparative molecular field analysis of quinoline derivatives as selective and noncompetitive mGluR1 antagonists

Chemical Biology and Drug Design

Volumn 70, Issue 6, 2007, Pages 511-519

  Nataraja Sekhar, Y ^a   Ravi Shashi Nayana, M ^a   Ravikumar, Muttineni ^b   Mahmood, S K ^a  

^a OSMANIA UNIVERSITY   (India)

^b GVK BIOSCIENCES PVT LTD   (India)

Author keywords

Drug design; G protein coupled receptor; Molecular modeling

Indexed keywords

GLUTAMATE RECEPTOR ANTAGONIST; QUINOLINE DERIVATIVE;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; CORRELATIONAL STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG INHIBITION; ELECTRICITY; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOSPECIFICITY;

ANIMALS; DRUG DESIGN; MICE; MODELS, MOLECULAR; QUINOLINES; RECEPTORS, AMPA; SOFTWARE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 36348986080     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2007.00596.x     Document Type: Article

References (30)

1. Masu M., Tanabe Y., Tsuchida K., Shigemoto R., Nakanishi S. (1991) Sequence and expression of a metabotropic glutamate receptor. Nature (London) 349 : 760 765.
2. Nakanishi S., Masu M. (1994) Molecular diversity and functions of glutamate receptors. Annu Rev Biophys Biomol Struct 23 : 319 348.
3. Hollmann M., Heinemann S. (1994) Cloned glutamate receptors. Annu Rev Neurosci 17 : 31 108.
4. Aramori I., Nakanishi S. (1992) Signal transduction and pharmacological characteristics of a metabotropic glutamate receptor, mGluRl, in transfected CHO cells. Neuron 8 : 757 765.
5. O'Hara P.J., Sheppard P.O., Thogersen H., Venezia D., Haldeman B.A., McGrane V., Houamed K.M., Thomsen C., Gilbert T.L., Mulvihill E.R. (1993) The ligand-binding domain in metabotropic glutamate receptors is related to bacterial periplasmic binding proteins. Neuron 11 : 41 52.
6. Okamoto T., Sekiyama N., Otsu M., Shimada Y., Sato A., Nakanishi S., Jingami H. (1998) Expression and purification of the extracellular ligand binding region of metabotropic glutamate receptor subtype 1. J Biol Chem 273 : 13089 13096.
7. Pin J.P., Duvoisin R. (1995) The metabotropic glutamate receptors: structure and functions. Neuropharmacology 34 : 1 26.
8. Schoepp D.D. (1994) Novel functions for subtypes of metabotropic. glutamate receptors. Neurochem Int 24 : 439 449.
9. Miller S., Kesslac J.P., Romano C., Cotman C.W. (1994) Roles of metabotropic glutamate receptors in brain plasticity and pathology. Ann N Y Acad Sci 757 : 460 474.
10. Bordi F., Ugolini A. (1999) Group I metabotropic glutamate receptors: implications for brain diseases. Prog Neurobiology 59 : 55 79.
11. Gasparini F., Kuhn R., Pin J.P. (2002) Allosteric modulators of group I metabotropic glutamate receptors: novel subtype-selective ligands and therapeutic perspectives. Curr Opin Pharmacol 2 : 43 49.
12. Lesage A.S.J. (2004) Role of group I metabotropic glutamate receptors mGlu1 and mGlu5 in nociceptive signaling. Curr Neuropharmacol 2 : 363 393.
13. Varney M.A., Gereau R.W. (2002) Metabotropic glutamate receptor involvement in models of acute and persistent pain: prospects for the development of novel analgesics. Curr Drug Targets CNS & Neurol Disord 1 : 283 296.
14. Neugebauer V. (2002) Metabotropic glutamate receptors - important modulators of nociception and pain behavior. Pain 98 : 1 8.
15. Spooren W., Ballard T., Gasparini F., Amalric M., Mutel V., Schreiber R. (2003) Insight into the function of Group I and Group II metabotropic glutamate (mGlu) receptors: behavioural characterization and implications for the treatment of CNS disorders. Behav Pharmacol 14 : 257 277.
16. Litschig S., Gasparini F., Rueegg D., Stoehr N., Flor P.J., Vranesic I., Prezeau L., Pin J.P., Thomsen C., Kuhn R. (1999) CPCCOEt, a noncompetitive metabotropic glutamate receptor 1 antagonist, inhibits receptor signaling without affecting glutamate binding. Mol Pharmacol 55 : 453 461.
17. De Vry J., Horvath E., Schreiber R. (2001) Neuroprotective and behavioral effects of the selective metabotropic glutamate mGlu(1) receptor antagonist BAY 36-7620. Eur J Pharmacol 428 : 203 214.
18. Okada M., Takahashi M., Hayashibe S 1999) PCT Int. Appl. WO 9944639.
19. Van Wagenen C., Moe S.T., Smith D.L., Sheehan S.M., Shcherbakova I., Travato R., Walton R., Barmore R., Delmar E.G., Stormann T.M 2000) PCT Int. Appl. WO 2000073283.
20. Binggeli A., Maerki H., Mutel V., Wilhelm M., Wostl W 2002) PCT Int. Appl. WO 2002051418.
21. Clark B.P., Harris J.R., Kingston A.E 2000) PCT Int. Appl. WO 2000026199.
22. Ambler S.J., Baker S.R., Clark B.P., Coleman D.S., Foglesong R.J., Goldsworthy J., Jagdmann G.E., Johnson K.W., Kingston A.E., Owton W.M., Schoepp D.D., Hong J.E., Schkeryantz J.M., Vannieuwenhze M.S., Zia- Ebrahimi M.S 2001) PCT Int. Appl. WO 2001032632.
23. Micheli F., Di Fabio R., Bordi F., Cavallini P., Cavanni P., Donati D., Faedo S., Maffeis M., Sabbatini F.M., Tarzia G., Tranquillini M.E. (2003) 2,4-Dicarboxy-pyrroles as selective non-Competitive mGluR1 antagonists: further characterization of 3,5-Dimethyl pyrrole-2, 4-dicarboxylic acid 2-propyl ester 4-(1,2,2-Trimethyl-propyl) ester and structure-Activity relationships. Bioorg Med Chem Lett 13 : 2113.
24. Zheng G.Z., Bhatia P., Daanen J., Kolsa T., Patel M., Latshaw S., El Kouhen O.F. et al. (2005) Structure-Activity Relationship of Triazafluorenone Derivatives as Potent and Selective mGluR1 Antagonists. J Med Chem 48L : 7374.
25. Zheng G.Z., Bhatia P., Kolsa T., Patel M., El Kouhen O.F., Chang R., Uchic M.E. et al. (2006) Correlation between brain/plasma ratios and efficacy in neuropathic pain models of selective metabotropic glutamate receptor 1 antagonists. Bioorg Med Chem Lett 16 : 4936.
26. Mabire D., Coupa S., Adelinet C., Poncelet A., Simonnet Y., Venet M., Wouters R., Lesage A.S.J., Beijsterveldt L.V., Bischoff F. (2005) Synthesis, Structure-Activity Relationship, and Receptor Pharmacology of a New Series of Quinoline Derivatives Acting as Selective, Noncompetitive mGlu1 Antagonists. J Med Chem 48 : 2134.
27. Oprea T.I., Waller C.L., Marshall G.R. (1994) Three-dimensional quantitative structure-activity relationship of human immunodeficiency virus (I) protease inhibitors. 2. Predictive power using limited exploration of alternate binding modes. J Med Chem 37 : 2206.
28. Tripos inc., Sybyl 6.8.1 1699 South Hanely Rd., St. Louis, MO 63144, USA.
29. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. (1985) Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc 107 : 3902 3909.
30. Cramer R.D. III., Patterson D.E., Bunce J.D. (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110 : 5959.