Synthesis and structure-activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel

European Journal of Medicinal Chemistry

Volumn 75, Issue , 2014, Pages 391-402

  Rodrigues, Nuno ^a,b   Bennis, Khalil ^a,b   Vivier, Delphine ^a,b   Pereira, Vanessa ^a,c   Chatelain, Franck C ^d   Chapuy, Eric ^a,c   Deokar, Hemantkumar ^a,b   Busserolles, Jérôme ^a,c   Lesage, Florian ^d   Eschalier, Alain ^a,c,e   Ducki, Sylvie ^a,b  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b ICCF   (France)

^c Pharmacologie Fondamentale et Clinique de la Douleur ^*  (France)

^d Laboratory of Excellence in Ion Channel Science and Therapeutics   (France)

^e UNIVERSITY HOSPITAL OF CLERMONT FERRAND   (France)

Author keywords

Analgesic agents; Antinociceptive; Caffeate esters; Pain; QSAR; Structure activity relationship study; TREK 1 channel

Indexed keywords

ANALGESIC AGENTS; ANTINOCICEPTIVE; CAFFEATE ESTERS; PAIN; QSAR; STRUCTURE-ACTIVITY RELATIONSHIP STUDY; TREK-1 CHANNEL;

ANALGESICS; ANIMALS; CAFFEIC ACIDS; CINNAMATES; ESTERS; MALE; MICE; MODELS, MOLECULAR; PAIN; POTASSIUM CHANNELS, TANDEM PORE DOMAIN; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS;

EID: 84894582647     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.01.049     Document Type: Article

References (32)

1. E. Bourinet, A. Alloui, A. Monteil, C. Barrere, B. Couette, O. Poirot, A. Pages, J. McRory, T. Snutch, A. Eschalier, and J. Nargeot Silencing of the Cav3.2 T-type calcium channel gene in sensory neurons demonstrates its major role in nociception EMBO J. 24 2005 315 324 (Pubitemid 40216136)
2. T.R. Cummins, P.L. Sheets, and S.G. Waxman The roles of sodium channels in nociception: implications for mechanisms of pain Pain 131 2007 243 257 (Pubitemid 47374344)
3. D. Juilius, and A.I. Basbaum Molecular mechanisms of nociception Nature 413 2001 203 210 (Pubitemid 32867885)
4. + channel EMBO J. 17 1998 4283 4290 (Pubitemid 28362619)
5. F. Maingret, A.J. Patel, F. Lesage, M. Lazdunski, and E. Honore Mechano- or acid stimulation, two interactive modes of activation of the TREK-1 potassium channel J. Biol. Chem. 274 1999 26691 26696
6. + channel Biochem. Biophys. Res. Commun. 292 2002 339 346 (Pubitemid 34694269)
7. A. Dedman, R. Sharif-Naeini, J.H.A. Folgering, F. Duprat, A. Patel, and E. Honore The mechano-gated K-2P channel TREK-1 Eur. Biophys. J. 38 2009 293 303
8. W. Treptow, and M.L. Klein The membrane-bound state of K2P potassium channels J. Am. Chem. Soc. 132 2010 8145 8151
9. + channel involved in polymodal pain perception EMBO J. 25 2006 2368 2376 (Pubitemid 44012220)
10. + channels TRAAK and TREK-1 control both warm and cold perception EMBO J. 28 2009 1308 1318
11. J. Noël, G. Sandoz, and F. Lesage Molecular regulations governing TREK and TRAAK functions Channels 5 2011 402 409
12. S.N. Bagriantsev, K.H. Ang, A. Gallardo-Godoy, K.A. Clark, M.R. Arkin, A.D. Renslo, and D.L. Minor Jr. A high-throughput functional screen identifies small molecule regulators of temperature- and mechano-sensitive K2P channels ACS Chem Biol. 16 2013 1841 1851
13. A. Doble The pharmacology and mechanism of action of riluzole Neurology 47 1996 S233 S241
14. + channels TREK-1 and TRAAK Mol. Pharmacol. 57 2000 906 912 (Pubitemid 30253373)
15. A. Cadaveira-Mosquera, S.J. Ribeiro, A. Reboreda, M. Perez, and J.A. Lamas Activation of TREK currents by the neuroprotective agent riluzole in mouse sympathetic neurons J. Neurosci. 31 2011 1375 1385
16. S. Danthi, J.A. Enyeart, and J.J. Enyeart Caffeic acid esters activate TREK-1 potassium channels and inhibit depolarization-dependent secretion Mol. Pharmacol. 65 2004 599 610 (Pubitemid 38264027)
17. H. Cho, M. Ueda, M. Tamaoka, M. Hamaguchi, K. Aisaka, Y. Kiso, T. Inoue, R. Ogino, and T. Tatsuoka Novel caffeic acid derivatives: extremely potent inhibitors of 12-lipoxygenase J. Med. Chem. 34 1991 1503 1505
18. L.H. Hu, H.B. Zou, J.X. Gong, H.B. Li, L.X. Yang, W. Cheng, C.X. Zhou, H. Bai, F. Gueritte, and Y. Zhao Synthesis and biological evaluation of a natural ester sintenin and its synthetic analogues J. Nat. Prod. 68 2005 342 348 (Pubitemid 40545468)
19. + channels by polyunsaturated fatty acids and lysophospholipids J. Membr. Biol. 195 2003 147 164 (Pubitemid 37338957)
20. C.A. Zarate Jr., and H.K. Manji Riluzole in psychiatry: a systematic review of the literature Expert Opin. Drug Metab. Toxicol. 4 2008 1223 1234
21. C. Pittenger, C. Vladimir, M. Banasr, M. Bloch, J.H. Krystal, and G. Sanacora Riluzole in the treatment of mood and anxiety disorders CNS Drugs 22 2008 761 786
22. M.C. Obinu, M. Reibaud, V. Blanchard, S. Moussaoui, and A. Imperato Neuroprotective effect of riluzole in a primate model of Parkinson's disease: behavioral and histological evidence Mov. Disord. 17 2002 12 19 (Pubitemid 36041255)
23. D.L. Ginsberg Riluzole for treatment-resistant obsessive-compulsive disorder Prim. Psychiatry 12 2005 33 34 (Pubitemid 41531967)
24. T.J. Ritchie, P. Ertl, and R. Lewis The graphical representation of ADME-related molecule properties for medicinal chemists Drug Discov. Today 16 2011 65 72
25. T. Wa̧seka, J. Olczakb, and T. Janecki New, simple and versatile synthesis of protected α-alkylidene-β-amino acids from activated vinylphosphonates Synlett 10 2006 1507 1510
26. + channel EMBO J. 15 1996 6854 6862
27. H. Miranda, F. Sierralta, and G. Pinardi Neostigmine interactions with non-steroidal anti-inflammatory drugs Br. J. Pharmacol. 135 2002 219 222
28. E. Siegmund, R. Cadmus, and G. Lu A method for evaluating both non-narcotic and narcotic analgesics Proc. Soc. Exp. Biol. Med. 95 1957 729 731
29. S.L. Dixon, A.M. Smondyrev, and S.N. Rao PHASE: a novel approach to pharmacophore modeling and 3D database searching Chem. Biol. Drug Des. 67 2006 370 372
30. S.L. Dixon, A.M. Smondyrev, E.H. Knoll, S.N. Rao, D.E. Shaw, and R.A. Friesner PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results J. Comput. Aided Mol. Des. 20 2006 647 671 (Pubitemid 46023928)
31. T. Nagaaoka, A.H. Bansjota, I.S. Tezuka, and S. Kadota Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-metastatic murine colon 26-L5 carcinoma cell line Bioorg. Med. Chem. 10 2002 3351 3359 (Pubitemid 34863215)
32. S. Saito, S. Kurakane, M. Seki, E. Takai, T. Kasai, and J. Kawabata Radical scavenging activity of dicaffeoyloxycyclohexanes: contribution of an intramolecular interaction of two caffeoyl residues Bioorg. Med. Chem. 13 2005 4191 4199 (Pubitemid 40779388)