Tryptamine-Based Derivatives as Transient Receptor Potential Melastatin Type 8 (TRPM8) Channel Modulators

Journal of Medicinal Chemistry

Volumn 59, Issue 5, 2016, Pages 2179-2191

  Bertamino, Alessia ^a   Ostacolo, Carmine ^b   Ambrosino, Paolo ^c   Musella, Simona ^b   Di Sarno, Veronica ^a   Ciaglia, Tania ^a   Soldovieri, Maria Virginia ^c   Iraci, Nunzio ^a   Fernandez Carvajal, Asia ^d   De La Torre Martinez, Roberto ^d   Ferrer Montiel, Antonio ^d   Gonzalez Muniz, Rosario ^e   Novellino, Ettore ^b   Taglialatela, Maurizio ^c   Campiglia, Pietro ^a   Gomez Monterrey, Isabel ^b  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF MOLISE   (Italy)

^d MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

^e INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BIPHENYL 4 YLMETHYL) 3 (2 BROMOETHYL) 1H INDOLE; 1 (IODOMETHYL) 4 PHENYLBENZENE; 2 (1H INDOL 3 YL) N (4 PHENOXYBENZYL) ETHANAMINE; 2 (1H INDOL 3 YL) N (4 PHENOXYBENZYL)ETHANAMINE; 2 (1H INDOL 3 YL) N (ISOQUINOLIN 5 YLMETHYL)ETHANAMINE; 2 (1H INDOL 3 YL) N (NAPHTHALEN 1 YLMETHYL)ETHANAMINE; 2 (1H INDOL 3 YL) N (QUINOLIN 5 YLMETHYL)ETHANAMINE; 2 (1H INDOL 3 YL) N [(10 METHYLANTHRACEN 9 YL)METHYL] ETHANAMINE; 2 (1H INDOL 3 YL) N [(2 METHOXYNAPHTHALEN 1 YL)METHYL] ETHANAMINE; 2 [(1,1' BIPHENYL) 4 YL] N [2 (1 METHYL 1H INDOL 3 YL)ETHYL] ETHANAMINE; 2 [1 [(1,1' BIPHENYL) 4 YLMETHYL] 1H INDOL 3 YL] N (3,4 DIMETHOXYPHENETHYL)ETHANAMINE; 3 (2 BROMOETHYL) 1 METHYL 1H INDOLE; 5[[2 (1H INDOL 3 YL)ETHYLAMINO]METHYL] 2 METHOXYPHENOL; N (3,4 DIMETHOXYBENZYL) 2 (1H INDOL 3 YL)ETHANAMINE; N (4 CHLOROBENZYL) 2 (1 METHYL 1H INDOL 3 YL)ETHANAMINE; N (4 METHOXYBENZYL) 2 (1 METHYL 1H INDOL 3 YL)ETHANAMINE; N METHYL 2 (1 METHYL 1H INDOL 3 YL) N (4 PHENOXYBENZYL) ETHANAMINE; N [(1,2,3,4,TETRAHYDRONAPHTHALEN 1 YL)METHYL] 2 (1H INDOL 3 YL)ETHANAMINE; N [2 (1H INDOL 3 YL)ETHYL]NAPHTHALEN 1 AMINE; N [2 (1H INDOL 3 YL)ETHYL]NAPHTHALEN 2 AMINE; N,N DIBENZYL 2 (1H INDOL 3 YL)ETHANAMINE; TRANSIENT RECEPTOR POTENTIAL CHANNEL AFFECTING AGENT; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG; TRANSIENT RECEPTOR POTENTIAL CHANNEL M; TRPM8 PROTEIN, HUMAN; TRYPTAMINE;

AMINO ACID SEQUENCE; ARTICLE; BINDING SITE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG SYNTHESIS; EC50; ELECTROPHYSIOLOGY; HEK293 CELL LINE; HUMAN; HUMAN CELL; HYDROGEN BOND; IC50; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR MODEL; MOUSE; NONHUMAN; NUCLEOPHILICITY; PATCH CLAMP TECHNIQUE; PHARMACOPHORE; RACEMIC MIXTURE; RAT; STATIC ELECTRICITY; SUBSTITUTION REACTION; AGONISTS; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; HEK293 CELLS; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TRPM CATION CHANNELS; TRYPTAMINES;

EID: 84961196596     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01914     Document Type: Article

References (53)

1. Peier, A. M.; Moqrich, A.; Hergarden, A. C.; Reeve, A. J.; Andersson, D. A.; Story, G. M.; Earley, T. J.; Dragoni, I.; McIntyre, P.; Bevan, S.; Patapoutian, A. A TRP channel that senses cold stimuli and menthol Cell 2002, 108, 705-715 10.1016/S0092-8674(02)00652-9
2. Proudfoot, C. J.; Garry, E. M.; Cottrell, D. F.; Rosie, R.; Anderson, H.; Robertson, D. C.; Fleetwood-Walker, S. M.; Mitchell, R. Analgesia mediated by the TRPM8 cold receptor in chronic neuropathic pain Curr. Biol. 2006, 16, 1591-1605 10.1016/j.cub.2006.07.061
3. Knowlton, W. M.; Daniels, R. L.; Palkar, R.; McCoy, D. D.; McKemy, D. D. Pharmacological blockade of TRPM8 ion channels alters cold and cold pain responses in mice PLoS One 2011, 6, e25894 10.1371/journal.pone.0025894
4. Varrassi, G.; Muller-Schwefe, G.; Pergolizzi, J.; Oronska, A.; Morlion, B.; Mavrocordatos, P.; Margarit, C.; Mangas, C.; Jaksch, W.; Huygen, F.; Collett, B.; Berti, M.; Aldington, D.; Ahlbeck, K. Pharmacological treatment of chronic pain-the need for CHANGE Curr. Med. Res. Opin. 2010, 26, 1231-1245 10.1185/03007991003689175
5. Zhang, L.; Barritt, G. J. Evidence that TRPM8 is an androgen-dependent Ca2+ channel required for the survival of prostate cancer cells Cancer Res. 2004, 64, 8365-8373 10.1158/0008-5472.CAN-04-2146
6. Beck, B.; Bidaux, G.; Bavencoffe, A.; Lemonnier, L.; Thebault, S.; Shuba, Y.; Barrit, G.; Skryma, R.; Prevarskaya, N. Prospects for prostate cancer imaging and therapy using high-affinity TRPM8 activators Cell Calcium 2007, 41, 285-294 10.1016/j.ceca.2006.07.002
7. Dhennin-Duthille, I.; Gautier, M.; Faouzi, M.; Guilbert, A.; Brevet, M.; Vaudry, D.; Ahidouch, A.; Sevestre, H.; Ouadid-Ahidouch, H. High expression of transient receptor potential channels in human breast cancer epithelial cells and tissues: correlation with pathological parameters Cell. Physiol. Biochem. 2011, 28, 813-822 10.1159/000335795
8. Ouadid-Ahidouch, H.; Dhennin-Duthille, I.; Gautier, M.; Sevestre, H.; Ahidouch, A. TRP calcium channel and breast cancer: expression, role and correlation with clinical parameters Bull. Cancer 2012, 99, 655-664 10.1684/bdc.2012.1595
9. Yee, N. S.; Zhou, W.; Lee, M. Transient receptor potential channel TRPM8 is over-expressed and required for cellular proliferation in pancreatic adenocarcinoma Cancer Lett. 2010, 297, 49-55 10.1016/j.canlet.2010.04.023
10. Yamamura, H.; Ugawa, S.; Ueda, T.; Morita, A.; Shimada, S. TRPM8 activation suppresses cellular viability in human melanoma Am. J. Physiol. Cell Physiol. 2008, 295, C296-C301 10.1152/ajpcell.00499.2007
11. Lashinger, E. S.; Steiginga, M. S.; Hieble, J. P.; Leon, L. A.; Gardner, S. D.; Nagilla, R.; Davenport, E. A.; Hoffman, B. E.; Laping, N. J.; Su, X. AMTB, a TRPM8 channel blocker: evidence in rats for activity in overactive bladder and painful bladder syndrome Am. J. Physiol. Renal Physiol. 2008, 295, F803-F810 10.1152/ajprenal.90269.2008
12. Andersson, K. E.; Gratzke, C.; Hedlund, P. The role of the transient receptor potential (TRP) superfamily of cation-selective channels in the management of the overactive bladder BJU Int. 2010, 106, 1114-1127 10.1111/j.1464-410X.2010.09650.x
13. Fernández-Peña, C.; Viana, F. Targeting TRPM8 for pain relief Open Pain J. 2013, 6, 154-164 10.2174/1876386301306010154
14. Parra, A.; Madrid, R.; Echevarria, D.; del Olmo, S.; Morenilla-Palao, C.; Acosta, M. C.; Gallar, J.; Dhaka, A.; Viana, F.; Belmonte, C. Ocular surface wetness is regulated by TRPM8-dependent cold thermoreceptors of the cornea Nat. Med. 2010, 16, 1396-1399 10.1038/nm.2264
15. Foster, A.; Van Der Logt, C. P. E.; Tareilus, E. W. Tetrahydropyrimidine-2-one derivatives and their uses. WO2004026840, 2005; Unilever Plc (GB)
16. Bassoli, A.; Borgonovo, G.; Busnelli, G.; Morini, G. Synthesis of a new family of N-aryl lactams active on chemesthesis and taste Eur. J. Org. Chem. 2006, 2006, 1656-1663 10.1002/ejoc.200500677
17. Calvo, R.; Chen, J.; Illig, C.; Meegalla, S.; Parks, D.; Parsons, W.; Player, M. R. Substituted benzimdazole derivatives useful as trpm8 receptor modulators. WO2012109100, 2012; Janssenn Pharmaceutica NV (BE)
18. Irlapati, N. R.; Thomas, A.; Kurhe, D. K.; Shelke, S. Y.; Khairatkar, J. N.; Viswanadha, S.; Mukhopadhyay, I. Fused oxazole and thiazole derivatives as trpms modulators. WO2010010435, 2010; Glenmark Pharmaceutical SA(CH).
19. Tamayo, N. A.; Bo, Y.; Gore, V.; Ma, V.; Nishimura, N.; Tang, P.; Deng, H.; Klionsky, L.; Lehto, S. G.; Wang, W.; Youngblood, B.; Chen, J.; Correll, T. L.; Bartberger, M. D.; Gavva, N. R.; Norman, M. H. Fused piperidines as a novel class of potent and orally available transient receptor potential melastatin type 8 (TRPM8) antagonists J. Med. Chem. 2012, 55, 1593-1611 10.1021/jm2013634
20. Zhu, B.; Xia, M.; Xu, X.; Ludovici, D. W.; Tennakoon, M.; Youngman, M. A.; Matthews, J. M.; Dax, S. L.; Colburn, R. W.; Qin, N.; Hutchinson, T. L.; Lubin, M. L.; Brandt, M. R.; Stone, D. J.; Flores, C. M.; Macielag, M. J. Arylglycine derivatives as potent transient receptor potential melastatin 8 (TRPM8) antagonists Bioorg. Med. Chem. Lett. 2013, 23, 2234-2237 10.1016/j.bmcl.2013.01.062
21. Ostacolo, C.; Ambrosino, P.; Russo, R.; Lo Monte, M.; Soldovieri, M. V.; Laneri, S.; Sacchi, A.; Vistoli, G.; Taglialatela, M.; Calignano, A. Isoxazole derivatives as potent transient receptor potential melastatin type 8 (TRPM8) agonists Eur. J. Med. Chem. 2013, 69, 659-669 10.1016/j.ejmech.2013.08.056
22. Ferrer-Montiel, A.; Fernandez-Carvajal, A.; Planells-Cases, R.; Fernandez-Ballester, G.; Gonzalez-Ros, J. M.; Messeguer, A.; Gonzalez-Muniz, R. Advances in modulating thermosensory TRP channels Expert Opin. Ther. Pat. 2012, 22, 999-1017 10.1517/13543776.2012.711320
23. Than, J. Y.; Li, L.; Hasan, R.; Zhang, X. Excitation and modulation of TRPA1, TRPV1, and TRPM8 channel-expressing sensory neurons by the pruritogen chloroquine J. Biol. Chem. 2013, 288, 12818-12827 10.1074/jbc.M113.450072
24. Weil, A.; Moore, S. E.; Waite, N. J.; Randall, A.; Gunthorpe, M. J. Conservation of functional and pharmacological properties in the distantly related temperature sensors TRVP1 and TRPM8 Mol. Pharmacol. 2005, 68, 518-527 10.1124/mol.105.012146
25. Terada, Y.; Kitajima, M.; Taguchi, F.; Takayama, H.; Horie, S.; Watanabe, T. Identification of indole alkaloid structural units important for stimulus-selective TRPM8 inhibition: SAR study of naturally occurring iboga derivatives J. Nat. Prod. 2014, 77, 1831-1838 10.1021/np500235b
26. DeFalco, J.; Steiger, D.; Dourado, M.; Emerling, D.; Duncton, M. A. 5-benzyloxytryptamine as an antagonist of TRPM8 Bioorg. Med. Chem. Lett. 2010, 20, 7076-7079 10.1016/j.bmcl.2010.09.099
27. Campiglia, P.; Aquino, C.; Bertamino, A.; Sala, M.; Gomez-Monterrey, I. M.; Novellino, E.; Grieco, P. Novel route in the synthesis of ψ[CH2NH] amide bond surrogate Tetrahedron Lett. 2008, 49, 731-734 10.1016/j.tetlet.2007.11.112
28. Fürstner, A.; Langemann, K. Macrocycles by ring-closing metathesis Synthesis 1997, 1997, 792-803 10.1055/s-1997-4472
29. Bautista, D. M.; Siemens, J.; Glazer, J. M.; Tsuruda, P. R.; Basbaum, A. I.; Stucky, C. L.; Jordt, S. E.; Julius, D. The menthol receptor TRPM8 is the principal detector of environmental cold Nature 2007, 448, 204-208 10.1038/nature05910
30. McKemy, D. D.; Neuhausser, W. M.; Julius, D. Identification of a cold receptor reveals a general role for TRP channels in thermosensation Nature 2002, 416, 52-58 10.1038/nature719
31. Andersson, D. A.; Chase, H. W.; Bevan, S. TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH J. Neurosci. 2004, 24, 5364-5369 10.1523/JNEUROSCI.0890-04.2004
32. Behrendt, H. J.; Germann, T.; Gillen, C.; Hatt, H.; Jostock, R. Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay Br. J. Pharmacol. 2004, 141, 737-745 10.1038/sj.bjp.0705652
33. Malkia, A.; Madrid, R.; Meseguer, V.; de la Pena, E.; Valero, M.; Belmonte, C.; Viana, F. Bidirectional shifts of TRPM8 channel gating by temperature and chemical agents modulate the cold sensitivity of mammalian thermoreceptors J. Physiol. 2007, 581, 155-174 10.1113/jphysiol.2006.123059
34. Taberner, F. J.; López-Córdoba, A.; Fernández-Ballester, G.; Korchev, Y.; Ferrer-Montiel, A. The region adjacent to the C-end of the inner gate in transient receptor potential melastatin 8 (TRPM8) channels plays a central role in allosteric channel activation J. Biol. Chem. 2014, 289, 28579-28594 10.1074/jbc.M114.577478
35. Liao, M.; Cao, E.; Julius, D.; Cheng, Y. Structure of the TRPV1 ion channel determined by electron cryo-microscopy Nature 2013, 504, 107-112 10.1038/nature12822
36. SiteMap; Schrödinger LLC: New York, 2015.
37. Ambrosino, P.; Soldovieri, M. V.; De Maria, M.; Russo, C.; Taglialatela, M. Functional and biochemical interaction between PPARα receptors and TRPV1 channels: Potential role in PPARα agonists-mediated analgesia Pharmacol. Res. 2014, 87, 113-122 10.1016/j.phrs.2014.06.015
38. Madhavi Sastry, G.; Adzhigirey, M.; Day, T.; Annabhimoju, R.; Sherman, W. Protein and ligand preparation: Parameters, protocols, and influence on virtual screening enrichments J. Comput.-Aided Mol. Des. 2013, 27, 221-234 10.1007/s10822-013-9644-8
39. Protein Preparation Wizard; Schrödinger LLC: New York, 2015.
40. Epik; Schrödinger LLC: New York, 2015.
41. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and testing of the OPLS all atom force field on conformational energetics and properties of organic liquids J. Am. Chem. Soc. 1996, 118, 11225-11236 10.1021/ja9621760
42. Maestro; Schrödinger LLC: New York, 2015.
43. LigPrep; Schrödinger LLC: New York, 2015.
44. Halgren, T. A.; Murphy, R. B.; Friesner, R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening J. Med. Chem. 2004, 47, 1750-1759 10.1021/jm030644s
45. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy J. Med. Chem. 2004, 47, 1739-1749 10.1021/jm0306430
46. Glide; Schrödinger LLC: New York, 2015.
47. Friesner, R. A.; Murphy, R. B.; Repasky, M. P.; Frye, L. L.; Greenwood, J. R.; Halgren, T. A.; Sanschagrin, P. C.; Mainz, D. T. Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes J. Med. Chem. 2006, 49, 6177-6196 10.1021/jm051256o
48. Desmond Molecular Dynamics System; D.E. Shaw Research: New York, 2015.
49. Maestro-Desmond Interoperability Tools; Schrödinger LLC: New York, 2015.
50. Bowers, K. J.; Chow, E.; Xu, H.; Dror, R. O.; Eastwood, M. P.; Gregersen, B. A.; Klepeis, J. L.; Kolossvary, I.; Moraes, M. A.; Sacerdoti, F. D.; Salmon, J. K.; Shan, Y.; Shaw, D. E. Scalable algorithms for molecular dynamics simulations on commodity clusters. Proceedings of ACM/IEEE Supercomputing Conference, Tampa, FL, November 11-14 2006; ACM/IEEE, 2006; DOI: 10.1109/SC.2006.54.
51. Phase; Schrödinger LLC: New York, 2015.
52. Dixon, S. L.; Smondyrev, A. M.; Knoll, E. H.; Rao, S. N.; Shaw, D. E.; Friesner, R. A. 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. 2006, 20, 647-671 10.1007/s10822-006-9087-6
53. Dixon, S. L.; Smondyrev, A. M.; Rao, S. N. PHASE: A novel approach to pharmacophore modeling and 3D database searching Chem. Biol. Drug Des. 2006, 67, 370-372 10.1111/j.1747-0285.2006.00384.x