Design and synthesis of indole-based peptoids as potent noncompetitive antagonists of transient receptor potential vanilloid 1

Journal of Medicinal Chemistry

Volumn 50, Issue 24, 2007, Pages 6133-6143

  Quintanar Audelo, Martina ^a   Fernández Carvajal, Asia ^b   Van Den Nest, Wim ^c   Carreño, Cristina ^c   Ferrer Montiel, Antonio ^b   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

^c DiverDrugs SL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

[ARGINYL] [N (2,4 DICHLOROPHENETHYL)GLYCYL] N [2 (INDOL 3 YL)ETHYL]GLYCINAMIDE; ALKYL GROUP; CAPSAICIN; GLYCINE DERIVATIVE; INDOLE DERIVATIVE; PEPTOID; RESINIFERATOXIN; RUTHENIUM RED; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

ANIMAL CELL; ARTICLE; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; ELECTROPHYSIOLOGY; IC 50; NONHUMAN; OOCYTE; PAIN; PERIPHERAL NERVOUS SYSTEM; SOLID PHASE SYNTHESIS; STIMULATION; STRUCTURE ACTIVITY RELATION; XENOPUS;

ANALGESICS; ANIMALS; DRUG DESIGN; INDOLES; OLIGOPEPTIDES; OOCYTES; PATCH-CLAMP TECHNIQUES; PEPTOIDS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TRPV CATION CHANNELS; XENOPUS;

EID: 37849051087     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070612v     Document Type: Article

References (42)

1. Hunt, S. P.; Mantyh, P. W. The Molecular Dynamics of Pain Control. Nat. Rev. Neurosci. 2001, 2, 83-91.
2. Marx, J. Prolonging the Agony. Science 2004, 305, 326-329.
3. Brower, V. New Paths for Pain Relief. Nat. Biotech. 2000, 18, 387-391.
4. Kidd, B. L.; Urban, L. A. Mechanisms of Inflammatory Pain. Br. J. Anaesth. 2001, 87, 3-11.
5. Malmberg, A. B.; Chen, C.; Susumu, T.; Basbaum, A. I. Preserved Acute Pain in Reduced Neurophatic Pain in Mice Lacking PKC. Science 1997, 278, 279-283.
6. Julius, D.; Basbaum, A. I. Molecular Mechanisms of Nociception. Nature 2001, 413, 203-210.
7. Scholz, J.; Woolf, C. J. Can We Conquer Pain? Nat. Neurosci. 2002, 5, 1062-1067.
8. Szolcsányi, J. Forty Years in Capsaicin Research for Sensory Pharmacology and Physiology. Neuropeptides 2004, 38, 377-384.
9. Caterina, M. J.; Julius, D. The Vanilloid Receptor: A Molecular Gateway to the Pain Pathway. Annu. Rev. Neurosci. 2001, 24, 487-517.
10. Caterina, M. J. Vanilloids Receptors Take a TRP Beyond the Sensory Afferent. Pain 2003, 105, 5-9.
11. Beham, C. D.; Gunthorpe, M. J.; Davis, J. B. TRPV Channels as Temperature Sensors. Cell Calcium 2003, 33, 479-487.
12. Gavva, N. R.; Klionsky, L.; Qu, Y.; Shi, L.; Tamir, R.; Edenson, S.; Zhang, T. J.; Viswanadhan, V. N.; Toth, A.; Pearce, L. V.; Vanderah, T. W.; Porreca, F.; Blumberg, P. M.; Lile, J.; Sun, Y.; Wild, K.; Louis, J.; Treanor, J. J. S. Molecular Determinants of Vanilloid Sensitivity in TRPV1. J. Biol. Chem. 2004, 279, 20283-20295.
13. Caterina, M. J.; Schumacher, M. A.; Tominaga, M.; Rosen, T. A.; Levine, J. D.; Julius, D. The Capsaicin Receptor: A Heat-Activated Ion Channel in the Pain Pathway. Nature 1997, 389, 816-824.
14. Szallasi, A.; Cortright, D. N. Biochemical Pharmacology of the Vanilloid Receptor TRPV1. An Update. Eur. J. Biochem. 2004, 271, 1814-1819.
15. (a) Ferrer-Montiel, A. V.; García-Martínez, C.; Morenilla-Palao, C.; García-Sanz, N.; Fernández-Carvajal, A.; Fernández-Ballester, G.; Planells-Cases, R. Molecular Architecture of the Vanilloid Receptor. Insights for Drug Design. Eur. J. Biochem. 2004, 271, 1820-1826.
16. 2+/Calmodulin Modulates TRPV1 Activation by Capsaicin. J. Gen. Physiol. 2004, 123, 53-62.
17. Voets, T.; Talavera, K.; Owsianik, G.; Nilius, B. Sensing with TRP Channels. Nat. Chem. Biol. 2005, 1, 85-92.
18. Szallasi, A.; Blumberg, P. M. Vanilloid (Capsaicin) Receptors and Mechanisms. Pharmacol. Rev. 1999, 51, 159-211.
19. Szallasi, A. Vanilloid (Capsaicin) Receptors in Health and Disease. Am. J. Clin. Phatol. 2002, 118, 110-121.
20. Breitenbucher, J. G.; Chaplan, S. R.; Carruthers, N. I. The TRPV1 Vanilloid Receptor: A Target for Therapeutic Intervention. Annu. Rep. Med. Chem. 2005, 40, 185-196.
21. Appendino, G.; Munoz, E.; Fiebich, B. L. TRPV1 (Vanilloid Receptor, Capsaicin Receptor) Agonists and Antagonists. Expert. Opin. Ther. Patents 2003, 13, 1825-1837.
22. Culshaw, A. J.; Bevan, S.; Christiansen, M.; Copp, P.; Davis, A.; Davis, C.; Dyson, A.; Dziadulewicz, E. K.; Edwards, L.; Eggelte, H.; Fox, A.; Gentry, C.; Groarke, A.; Hallett, A.; Hart, T. W.; Hughes, G. A.; Knights, S.; Kotsonis, P.; Lee, W.; Lyothier, I.; McBryde, A.; McIntyre, P.; Paloumbis, G.; Panesar, M.; Patel, S.; Seiler, M-P.; Yaqoob, M.; Zimmermann, K. Identification and Biological Characterization of 6-Aryl-7-isopropylquinazolinones as Novel TRPV1 Antagonists that are Effective in Models of Chronic Pain. J. Med. Chem. 2006, 49, 471-474.
23. Rami, H. K.; Gunthorpe, M. J. The Therapeutic Potential of TRPV1 (VR1) Antagonists; Clinical Answers Await. Drug Discovery Today: Ther. Strateg. 2004, 1, 97-104.
24. Szallasi, A.; Appendino, G. Vanilloid Receptor TRPV1 Antagonists as the Next Generation of Painkillers. Are We Putting the Cart before the Horse? J. Med. Chem. 2004, 47, 2717-2723.
25. Planells-Cases, R.; García-Martínez, C.; Royo, M.; Pérez-Payá, E.; Carreño, C.; Albericio, F.; Messeguer, A.; Ferrer-Montiel, A. Small Molecules Targeting the Vanilloid Receptor Complex as Drugs for Inflammatory Pain. Drugs Future 2003, 28, 787-795.
26. Messeguer, A.; Planells-Cases, R.; Ferrer-Montiel, A. Physiology and Pharmacology of the Vanilloid Receptor. Curr. Neuropharmacol. 2006, 4, 1-15.
27. Westaway, S. M. The Potential of Transient Receptor Potential Vanilloid Type 1 Channel Modulators for the Treatment of Pain. J. Med. Chem. 2007, 50, 2589-2596.
28. Planells-Cases, R.; Aracil, A.; Merino, J. M.; Gallar, J.; Pérez-Payá, E.; Belmonte, C.; González-Ros, J. M.; Ferrer-Montiel, A. Arginine-Rich Peptides are Blockers of VR1 Channels with Analgesic Activity. FEBS Lett. 2000, 481, 131-136.
29. García-Martínez, C.; Humet, M.; Planells-Cases, R.; Gomis, A.; Caprini, M.; Viana, F.; De la Peña, E.; Sanchez-Baeza, F.; Carbonell, T.; De Felipe, C.; Pérez-Payá, E.; Belmonte, C.; Messeguer, A.; Ferrer-Montiel, A. Attenuation of Thermal Nociception and Hyperalgesia by VR1 Blockers. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 2374-2379.
30. Path, J. A.; Kirshenbaum, K.; Seurynck, S. L.; Zuckermann, R. N.; Barron, A. E. Pseudo-peptides in Drug Development; Nielsen. P. E., Ed.; Wiley-VCH Press: Weinheim UK, 2003; pp 1-31.
31. García-Martínez, C.; Fernández-Carvajal, A.; Valenzuela, B.; Gomis, A.; Van Den Nest, W.; Ferroni, S.; Carreño, C.; Belmonte, C.; Ferrer-Montiel, A. Design and Characterization of a Non-Competitive Antagonist of the Transient Receptor Potential Vanilloid Subunit 1 Channel with In Vivo Analgesic and Anti-inflammatory Activity. J. Pain 2006, 7, 735-746.
32. Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moss, W. H. Efficient Method for the Preparation of Peptoids [Oligo(N-Substituted Glycines] by Submonomer Solid-Phase Synthesis. J. Am. Chem. Soc. 1992, 114, 10646-10647.
33. Borch, R. F.; Hassid, A. I. New Method for the Methylation of Amines. J. Org. Chem. 1972, 37, 1673-1674.
34. Mancuso, A. J.; Swern, D. Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis. Synthesis 1981, 3, 165-184.
35. Yraola, F.; Ventura, R.; Vendrell, M.; Colombo, A.; Fernández, J. C.; De la Figuera, N.; Fernández-Forner, D.; Royo, M.; Forns, P.; Albericio, F. A Re-Evaluation of the Use of RINK, BAL, and PAL Resins and Linkers. QSAR Comb. Sci. 2004, 23, 145-152.
36. Miller, S. C.; Scanlan, T. S. Site-Selective N-Methylation of Peptides on Solid Support. J. Am. Chem. Soc. 1997, 119, 2301-2302.
37. Ferrer-Montiel, A. V.; Montal, M. Structure Function Relations in Ligand-Gated Ion Channels: Reconstitution in Lipid Bilayers and Heterologous Expression in Xenopus Oocytes. Methods, Companion Methods Enzymol. 1994, 6, 60-90.
38. Ferrer-Montiel, A. V.; Montal, M. Engineering the NMDA Receptor Channel Lining. Methods Mol. Biol. 1999, 128, 167-178.
39. Ferrer-Montiel, A. V.; Sun, W.; Montal, M. Molecular Design of the N-Methyl-D-Aspartate Receptor Binding Site for Phencyclidine and Dizolcipine. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8021-8025.
40. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 1970, 34, 595-598.
41. Madder, A.; Farcy, N.; Hosten, N. G. C.; De Muynck, H.; De Clercq, P-J.; Barry, J.; Davis, A. P. A Novel Sensitive Colorimetric Assay for Visual Detection of Solid-Phase Bound Amines. Eur. J. Org. Chem. 1999, 1999, 2787-2791.
42. Vázquez, J.; Albericio, F. An Useful Sensitive Color Test To Monitor Aldehydes on Solid-Phase. Tetrahedron Lett. 2001, 42, 6691-6693.