Methoctramine analogues inhibit responses to capsaicin and protons in rat dorsal root ganglion neurons

European Journal of Pharmacology

Volumn 505, Issue 1-3, 2004, Pages 37-50

  Mellor, Ian R ^a   Ogilvie, Jane ^b   Pluteanu, Florentina ^a   Clothier, Richard H ^b   Parker, Terence L ^b   Rosini, Michela ^c   Minarini, Anna ^c   Tumiatti, Vincenzo ^c   Melchiorre, Carlo ^c  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Channel block; Dorsal root ganglion; Methoctramine; Patch clamp; Polyamine; Vanilloid receptor

Indexed keywords

CAPSAICIN; DRUG ANALOG; METHOCTRAMINE; METHOCTRAMINE DERIVATIVE; POLYAMINE; PROTON; UNCLASSIFIED DRUG; VANILLOID RECEPTOR;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; FEMALE; FETUS; IC 50; MALE; NERVE CELL; NONHUMAN; PATCH CLAMP; PH MEASUREMENT; PRIORITY JOURNAL; RAT; SPINAL GANGLION; STRUCTURE ACTIVITY RELATION;

AGE FACTORS; ANIMALS; CAPSAICIN; DIAMINES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; FETUS; GANGLIA, SPINAL; HYDROGEN-ION CONCENTRATION; MALE; MEMBRANE POTENTIALS; MODELS, BIOLOGICAL; NEURONS; PATCH-CLAMP TECHNIQUES; PREGNANCY; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 8844234955     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2004.10.005     Document Type: Article

References (44)

1. 13C NMR chemical shift assignments of spermidine, spermine, and homologs Biophys. Chemist. 17 1983 67 74
2. A. Babes, B. Amuzescu, U. Krause, A. Scholz, M.L. Flonta, and G. Reid Cooling inhibits capsaicin-induced currents in cultured rat dorsal root ganglion neurones Neurosci. Lett. 317 2002 131 134
3. C.D. Benham, M.J. Gunthorpe, and J.B. Davis TRPV channels as temperature sensors Cell Calcium 33 2003 479 487
4. M.G. Bixel, C. Weise, M.L. Bolognesi, M. Rosini, M.J. Brierley, I.R. Mellor, P.N.R. Usherwood, C. Melchiorre, and F. Hucho Location of the polyamine binding site in the vestibule of the nicotinic acetylcholine receptor ion channel J. Biol. Chem. 276 2001 6151 6160
5. M.J. Caterina, and D. Julius The vanilloid receptor: a molecular gateway to the pain pathway Annu. Rev. Neurosci. 24 2001 487 517
6. M.J. Caterina, M.A. Schumacher, M. Tominaga, T.A. Rosen, J.D. Levine, and D. Julius The capsaicin receptor: a heat-activated ion channel in the pain pathway Nature 389 1997 816 824
7. M.J. Caterina, A. Leffler, A.B. Malmberg, W.J. Martin, J. Trafton, K.R. Petersen-Zeitz, M. Koltzenburg, A.I. Basbaum, and D. Julius Impaired nociception and pain sensation in mice lacking the capsaicin receptor Science 288 2000 306 313
8. V.N. Dedov, V.H. Tran, C.C. Duke, M. Connor, M.J. Christie, S. Mandadi, and B.D. Roufogalis Gingerols: a novel class of vanilloid receptor (VR1) agonists Br. J. Pharmacol. 137 2002 793 798
9. C. Garcia-Martinez, C. Morenilla-Palao, R. Planells-Cases, J.M. Merino, and A. Ferrer-Montiel Identification of an aspartic residue in the P-loop of the vanilloid receptor that modulates pore properties J. Biol. Chem. 275 2000 32552 32558
10. C. Garcia-Martinez, M. Humet, R. Planells-Cases, A. Gomis, M. Caprini, F. Viana, E. De La Pena, F. Sanchez-Baeza, T. Carbonell, C. De Felipe, E. Perez-Paya, C. Belmonte, A. Messeguer, and A. Ferrer-Montiel Attenuation of thermal nociception and hyperalgesia by VR1 blockers Proc. Natl. Acad. Sci. U. S. A. 99 2002 2374 2379
11. M.J. Gunthorpe, C.D. Benham, A. Randall, and J.B. Davis The diversity in the vanilloid (TRPV) receptor family of ion channels Trends Pharmacol. Sci. 23 2002 183 191
12. S.M. Huang, T. Bisogno, M. Trevisani, A. Al-Hayani, L. De Petrocellis, F. Fezza, M. Tognetto, T.J. Petros, J.F. Krey, C.J. Chu, J.D. Miller, S.N. Davies, P. Geppetti, J.M. Walker, and V. Di Marzo An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors Proc. Natl. Acad. Sci. U. S. A. 99 2002 8400 8405
13. Y. Ishida, S. Ugawa, T. Ueda, S. Murakami, and S. Shimada Vanilloid receptor subtype-1 (VR1) is specifically localized to taste papillae Mol. Brain Res. 107 2002 17 22
14. N. Kedei, T. Szabo, J.D. Lile, J.J. Treanor, Z. Olah, M.J. Iadarola, and P.M. Blumberg Analysis of the native quaternary structure of vanilloid receptor 1 J. Biol. Chem. 276 2001 28613 28619
15. M. Kress, and H.U. Zeilhofer Capsaicin, protons and heat: new excitement about nociceptors Trends Pharmacol. Sci. 20 1999 112 118
16. C.A. Maggi, R. Patacchini, P. Santicioli, S. Giuliani, P. Geppetti, and A. Meli Protective action of ruthenium red toward capsaicin desensitization of sensory fibers Neurosci. Lett. 88 1988 201 205
17. C. Melchiorre, A. Cassinelli, and W. Quaglia Differential blockade of muscarinic receptor subtypes by polymethylene tetraamines. Novel class of selective antagonists of cardiac M-2 muscarinic receptors J. Med. Chem. 30 1987 201 204
18. C. Melchiorre, W. Quaglia, M.T. Picchio, D. Giardinà, L. Brasili, and P. Angeli Structure-activity relationships among methoctramine-related polymethylene tetraamines. Chain-length and substituent effects on M-2 muscarinic receptor blocking activity J. Med. Chem. 32 1989 79 84
19. I.R. Mellor, and P.N.R. Usherwood Targeting ionotropic receptors with polyamine-containing toxins Toxicon 43 2004 493 508
20. I.R. Mellor, T.J. Brier, F. Pluteanu, K. Strømgaard, A. Saghyan, N. Eldursi, M.J. Brierley, K. Andersen, J.W. Jaroszewski, P. Krogsgaard-Larsen, and P.N.R. Usherwood Modification of the philanthotoxin-343 polyamine moiety results in different structure-activity profiles at muscle nicotinic ACh, NMDA and AMPA receptors Neuropharmacology 44 2003 70 80
21. A. Minarini, W. Quaglia, V. Tumiatti, and C. Melchiorre An improved synthesis of N,N′-bis[6-o-methoxyphenyl methyl hexylamino]-1,8- octanediamine (methoctramine) Chem. Ind. 19 1989 652 653
22. A. Minarini, R. Budriesi, A. Chiarini, C. Melchiorre, and V. Tumiatti Further investigation on methoctramine-related tetraamines: effects of terminal N-substitution and of chain length separating the four nitrogens on M2 muscarinic receptor blocking activity Farmaco 46 1991 1167 1178
23. D.P. Mohapatra, S-Y. Wang, G.K. Wang, and C. Nau A tyrosine residue in TM6 of the vanilloid receptor TRPV1 involved in desensitization and calcium permeability of capsaicin-activated currents Mol. Cell. Neurosci. 23 2003 314 324
24. C. Montell, L. Birnbaumer, V. Flockerzi, R.J. Bindels, E.A. Bruford, M.J. Caterina, D.E. Clapham, C. Harteneck, S. Heller, D. Julius, I. Kojima, Y. Mori, R. Penner, D. Prawitt, A.M. Scharenberg, G. Schultz, N. Shimizu, and M.X. Zhu A unified nomenclature for the superfamily of TRP cation channels Mol. Cell 9 2002 229 231
25. I. Nagy, and H.P. Rang Similarities and differences between the responses of rat sensory neurons to noxious heat and capsaicin J. Neurosci. 19 1999 10647 10655
26. U. Oh, S.W. Hwang, and D. Kim Capsaicin activates a nonselective cation channel in cultured neonatal rat dorsal root ganglion neurons J. Neurosci. 16 1996 1659 1667
27. R. Planells-Cases, A. Aracil, J.M. Merino, J. Gallar, E. Perez-Paya, C. Belmonte, J.M. Gonzalez-Ros, and A.V. Ferrer-Montiel Arginine-rich peptides are blockers of VR-1 channels with analgesic activity FEBS Lett. 481 2000 131 136
28. L.S. Premkumar, S. Agarwal, and D. Steffen Single-channel properties of native and cloned rat vanilloid receptors J. Physiol. 545 2002 107 117
29. W. Quaglia, D. Giardinà, G. Marucci, C. Melchiorre, A. Minarini, and V. Tumiatti Structure-activity relationships among methoctramine-related polymethylene tetraamines: 3. Effect of the four nitrogens on M2 muscarinic blocking activity as revealed by symmetrical and unsymmetrical polyamines Farmaco 46 1991 417 434
30. M. Rosini, R. Budriesi, M.G. Bixel, M.L. Bolognesi, A. Chiarini, F. Hucho, P. Krogsgaard-Larsen, I.R. Mellor, A. Minarini, V. Tumiatti, P.N. Usherwood, and C. Melchiorre Design, synthesis, and biological evaluation of symmetrically and unsymmetrically substituted methoctramine-related polyamines as muscular nicotinic receptor noncompetitive antagonists J. Med. Chem. 42 1999 5212 5223
31. M. Rosini, M.G. Bixel, G. Marucci, R. Budriesi, M. Krauss, M.L. Bolognesi, A. Minarini, V. Tumiatti, F. Hucho, and C. Melchiorre Structure-activity relationships of methoctramine-related polyamines as muscular nicotinic receptor noncompetitive antagonists: 2. Role of polymethylene chain lengths separating amine functions and of substituents on the terminal nitrogen atoms J. Med. Chem. 45 2002 1860 1878
32. J.R. Savidge, S.P. Ranasinghe, and H.P. Rang Comparison of intracellular calcium signals evoked by heat and capsaicin in cultured rat dorsal root ganglion neurons and in a cell line expressing the rat vanilloid receptor, VR1 Neuroscience 102 2001 177 184
33. G.R. Seabrook, K.G. Sutton, W. Jarolimek, G.J. Hollingworth, S. Teague, J. Webb, N. Clark, S. Boyce, J. Kerby, Z. Ali, M. Chou, R. Middleton, G. Kaczorowski, and A.B. Jones Functional properties of the high-affinity TRPV1 (VR1) vanilloid receptor antagonist (4-hydroxy-5-iodo-3-methoxyphenylacetate ester) iodo-resiniferatoxin J. Pharmacol. Exp. Ther. 303 2002 1052 1060
34. D. Smart, M.J. Gunthorpe, J.C. Jerman, S. Nasir, J. Gray, A.I. Muir, J.K. Chambers, A.D. Randall, and J.B. Davis The endogenous lipid anandamide is a full agonist at the human vanilloid receptor (hVR1) Br. J. Pharmacol. 129 2000 227 230
35. G.D. Smith, M.J. Gunthorpe, R.E. Kelsell, P.D. Hayes, P. Reilly, P. Facer, J.E. Wright, J.C. Jerman, J.-P. Walhin, L. Ooi, J. Egerton, K.J. Charles, D. Smart, A.D. Randall, P. Anand, and J.B. Davis TRPV3 is a temperature-sensitive vanilloid receptor-like protein Nature 418 2002 186 190
36. K. Strømgaard, and I. Mellor AMPA receptor ligands: synthetic and pharmacological studies of polyamines and polyamine toxins Med. Res. Rev. 24 2004 589 620
37. A. Szallasi, and P.M. Blumberg Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper Neuroscience 30 1989 515 520
38. A. Szallasi, and V. Di Marzo New perspectives on enigmatic vanilloid receptors Trends Neurosci. 23 2000 491 497
39. M. Trevisani, D. Smart, M.J. Gunthorpe, M. Tognetto, M. Barbieri, B. Campi, S. Amadesi, J. Gray, J.C. Jerman, S.J. Brough, D. Owen, G.D. Smith, A.D. Randall, S. Harrison, A. Bianchi, J.B. Davis, and P. Geppetti Ethanol elicits and potentiates nociceptor responses via the vanilloid receptor-1 Nat. Neurosci. 5 2002 546 551
40. L. Urban, and A. Dray Capsazepine, a novel capsaicin antagonist, selectively antagonises the effects of capsaicin in the mouse spinal cord in vitro Neurosci. Lett. 134 1991 9 11
41. P. Wahl, C. Foged, S. Tullin, and C. Thomsen Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist Mol. Pharmacol. 59 2001 9 15
42. R. Waldmann, G. Champigny, F. Bassilana, C. Heurteaux, and M. Lazdunski A proton-gated cation channel involved in acid-sensing Nature 386 1997 173 177
43. J.M. Welch, S.A. Simon, and P.H. Reinhart The activation mechanism of rat vanilloid receptor 1 by capsaicin involves the pore domain and differs from the activation by either acid or heat Proc. Natl. Acad. Sci. U. S. A. 97 2000 13889 13894
44. 2+ currents through capsaicin- and proton-activated ion channels in rat dorsal root ganglion neurones J. Physiol. 503 1997 67 78