Convolutamydine A and synthetic analogues have antinociceptive properties in mice

Pharmacology Biochemistry and Behavior

Volumn 103, Issue 3, 2013, Pages 431-439

  Figueiredo, Gabriela S M ^a   Zardo, Renata S ^a   Silva, Bárbara V ^a   Violante, Flávio A ^b   Pinto, Angelo C ^a   Fernandes, Patricia D ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b INSTITUTO FEDERAL DE EDUCAÇÃO   (Brazil)

Author keywords

Analgesia; Antinociceptive activity; Convolutamydine; Isatin; Pain

Indexed keywords

3 ( 2 OXOPROPYL) 3 HYDROXY 2 OXINDOLE; 5 BROMO 3 ( 2 OXOPROPYL) 3 HYDROXY 2 OXINDOLE; ACETIC ACID; ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; ATROPINE; CHOLINERGIC RECEPTOR; CONVOLUTAMYDINE A; FORMALDEHYDE; MORPHINE; N(G) NITROARGININE METHYL ESTER; NALOXONE; NITRIC OXIDE; OPIATE; UNCLASSIFIED DRUG;

ANALGESIA; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ANTINOCICEPTION; AREA UNDER THE CURVE; ARTICLE; CHOLINERGIC SYSTEM; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG SYNTHESIS; FEMALE; HOT PLATE TEST; IC 50; LICKING; MALE; MEDIATOR; MOUSE; NEUROTRANSMISSION; NONHUMAN; PAIN; PRIORITY JOURNAL; SPINE;

ANALGESICS; ANIMALS; BEHAVIOR, ANIMAL; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; ISATIN; MALE; MICE; MOTOR ACTIVITY; PAIN; PAIN MEASUREMENT;

GYMNOLAEMATA; MUS;

EID: 84867773483     PISSN: 00913057     EISSN: 18735177     Source Type: Journal    
DOI: 10.1016/j.pbb.2012.09.023     Document Type: Article

References (62)

1. M.D. Aceto, L.S. Harris, and E.R. Bowman Etorphines: μ-opioid receptor-selective antinociception and low physical dependence capacity Eur J Pharmacol 338 1997 215 223 (Pubitemid 27507764)
2. E. Barocelli, V. Ballabeni, S. Bertoni, M. de Amici, and M. Impicciatore Evidence for specific analgesic activity of a muscarinic agonist selected among a new series of acetylenic derivatives Life Sci 68 2001 1775 1785 (Pubitemid 32245626)
3. H.M.T. Barros, M.A.L. Tannhauser, S.L. Tannhauser, and M. Tannhauser Enhanced detection of hyperactivity after drug withdrawal with a simple modification of the open-field apparatus J Pharmacol Methods 26 1991 269 275
4. N. Bernardini, P. Reeh, and S. Sauer Muscarinic M2 receptors inhibit heat induced CGRP release from isolated rat skin Neuroreport 12 2001 2457 2460 (Pubitemid 32682202)
5. N. Bernardini, S.K. Sauer, R. Haberberger, M.J. Fischer, and P.W. Reeh Excitatory nicotinic and desensitizing muscarinic (M2) effects on C-nociceptors in isolated rat skin J Neurosci 21 2001 3295 3302 (Pubitemid 32323511)
6. B. Bhrigu, D. Pathak, N. Siddiqui, M.S. Alam, and W. Ahsan Search for biological active isatins: A short review Int J Pharm Sci Drug Res 2 2010 229 235
7. + channels pathway Eur J Neurosci 24 2006 1175 1181 (Pubitemid 44268147)
8. S. Bruehl, J.W. Burns, O.Y. Chung, and M. Chont Pain-related effects of trait anger expression: neural substrates and the role of endogenous opioid mechanisms Neurosci Biobehav Rev 33 2009 475 491
9. L. Bueno, and J. Fioramonti Visceral perception: inflammatory and non-inflammatory mediators Gut 51 Suppl. I 2002 i19 i23
10. V. Chapman, and A.H. Dickenson The spinal and peripheral roles of bradykinin and prostaglandins in nociceptive processing in the rat Eur J Pharmacol 219 1992 427 433
11. H.O.J. Collier, J.C. Dinneen, C.A. Johnson, and C. Schneider The abdominal constriction response and its suppression by analgesic drugs in the mouse Br J Pharmacol Chemother 32 1968 295 310
12. G. Cravotto, G.B. Giovenzana, G. Palmisano, A. Penoni, T. Pilati, and M. Sisti Convolutamydine A: The first authenticated absolute configuration and enantioselective synthesis Tetrahedron Asymmetry 17 2006 3070 3074 (Pubitemid 44969571)
13. J.F.M. Da Silva, S.J. Garden, and A.C. Pinto The chemistry of isatins: A review from 1975 to 1999 J Braz Chem Soc 12 2001 273 324
14. 2 receptor antagonist Eur J Pharmacol 316 1996 277 286 (Pubitemid 27008162)
15. M. Decker, M. Buckley, and J. Brioni Differential effects of pretreatment with nicotine and lobeline on nicotine-induced changes in body temperature and locomotor activity in mice Drug Dev Res 31 1994 52 58 (Pubitemid 24103873)
16. N.B. Eddy, and D. Leimbach Synthetic analgesics: II. Dithienylbutenyl- and dithienylbutylamines J Pharmacol Exp Ther 107 1953 385 393
17. S.J. Garden, J.C. Torres, A.A. Ferreira, R.B. Silva, and A.C. Pinto A modified Sandmeyer methodology and the synthesis of (±)-convolutamydine A Tetrahedron Lett 38 1997 1501
18. M.C.M. Godoy, M.R. Figuera, A.E. Flores, M.A. Rubin, M.R. Oliveira, and N. Zanatta α2-Adrenoceptors and 5-HT receptors mediate the antinociceptive effect of new pyrazoles, but not of dipyrone Eur J Pharmacol 496 2004 93 97 (Pubitemid 39024321)
19. N.M. Gomes, C.M. Rezende, S.P. Fontes, M.E. Matheus, and P.D. Fernandes Antinociceptive activity of Amazonian Copaiba oils J Ethnopharmacol 109 2007 486 492 (Pubitemid 46054378)
20. M.D. Hall, N.K. Salam, J.L. Hellawell, H.M. Fales, C.B. Kensler, and J.A. Ludwig Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells J Med Chem 52 2009 3191 3204
21. K. Honda, A. Harada, Y. Takano, and H. Kamiya Involvement of M3 muscarinic receptors of the spinal cord in formalin-induced nociception in mice Brain Res 859 2000 38 44 (Pubitemid 30138191)
22. K. Honda, K. Koga, T. Moriyama, M. Koguchi, Y. Takano, and H. Kamiya Intrathecal alpha2 adrenoceptor agonist clonidine inhibits mechanical transmission in mouse spinal cord via activation of muscarinic M1 receptors Neurosci Lett 322 2002 161 164 (Pubitemid 34230544)
23. D.D. Hood, J.C. Eisenach, and R. Tuttle Phase I safety assessment of intrathecal neostigmine methylsulfate in humans Anesthesiology 82 1995 331 335
24. S. Hunskaar, and K. Hole The formalin test in mice: dissociation between inflammatory and non-inflammatory pain Pain 30 1987 103 114 (Pubitemid 17094194)
25. E.T. Iwamoto, and L. Marion Characterization of the anti-nociception produced by intrathecally administered muscarinic agonists in the rats J Pharmacol Exp Ther 266 1993 329 338 (Pubitemid 23315666)
26. J. Jage Opioid tolerance and dependence. Do they matter? Eur J Pain 9 2005 157 162 (Pubitemid 40311838)
27. P.G. Jones, and J. Dunlop Targeting the cholinergic system as a therapeutic strategy for the treatment of pain Neuropharmacol 53 2007 197 206 (Pubitemid 47187447)
28. Y. Kamano, H.-P. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, and G.R. Pettit Convolutamydine A, a novel bioactive hydroxyindole alkaloid from marine bryozoan Amathia convoluta Tetrahedron Lett 36 1995 2783 2784
29. C. Kennedy, and P. Leff Painful connection for ATP Nature 377 1995 385 386
30. B.B. Lorenzetti, and S.H. Ferreira Activation of the arginine-nitric oxide pathway in primary sensory neurons contributes to dipyrone-induced intrathecal and peripheral analgesia Inflamm Res 45 1996 308 311 (Pubitemid 26197553)
31. D. Lorke A new approach to practical acute toxicity testing Arch Toxicol 54 1983 275 287 (Pubitemid 14205493)
32. G. Luppi, M. Monari, R.J. Corrêa, F.A. Violante, A.C. Pinto, and B. Kaptein The first total synthesis of (R)-convolutamydine A Tetrahedron 62 2006 12017 12024 (Pubitemid 44794328)
33. A.V. Malkov, M.A. Kabeshov, M. Bella, O. Kysilka, D.A. Malyshev, and K. Pluháková Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: Application in the synthesis of convolutamydine A Org Lett 9 2007 5473 5476
34. M.E. Matheus, L.F. Berrondo, E.C. Vieitas, F.S. Menezes, and P.D. Fernandes Evaluation of the antinociceptive properties from Brillantaisia palisotii Lindau stems extracts J Ethnopharmacol 102 2005 377 381 (Pubitemid 41571844)
35. M.E. Matheus, F.A. Violante, S.J. Garden, A.C. Pinto, and P.D. Fernandes Isatins inhibit cyclooxygenase-2 and inducible nitric oxide synthase in a mouse macrophage cell line Eur J Pharmacol 556 2007 200 206 (Pubitemid 46074000)
36. M.F. Otuki, J. Ferreira, F.V. Lima, C. Meyre-Silva, A. Malheiros, and L.A. Muller Antinociceptive properties of mixture of alpha-amyrin and beta-amyrin triterpenes: evidence for participation of protein kinase C and protein kinase A pathways J Pharmacol Exp Ther 313 2005 310 318 (Pubitemid 40411356)
37. C.A. Parada, C.H. Tambeli, F.Q. Cunha, and S.H. Ferreira The major role of peripheral release of histamine and 5-hydroxytryptamine in formalin-induced nociception Neuroscience 102 2001 937 944 (Pubitemid 32155888)
38. S. Peddibhotla 3-Substituted-3-hydroxy-2-oxindole, an emerging new scaffold for drug discovery with potential anti-cancer and other biological activities Curr Bioact Compd 5 2009 20 38
39. M.M.G. Pinheiro, S.O. Bessa, C.E. Fingolo, R.M. Kuster, M.E. Matheus, and F.S. Menezes Antinociceptive activity of fractions from Couroupita guianensis Aubl. leaves J Ethnopharmacol 127 2010 407 413
40. O. Pol The involvement of the nitric oxide in the effects and expression of opioid receptors during peripheral inflammation Curr Med Chem 14 2007 1945 1955
41. W.M. Purcell, and C.K. Atterwill Mast cells in neuroimmune function: neurotoxicological and neuropharmacological perspectives Neurochem Res 20 1995 521 532
42. W. Riedel, and G. Neeck Nociception, pain, and antinociception: current concepts Z Rheumatol 60 2001 404 415 (Pubitemid 34066644)
43. J.H. Rosland, A. Tjolsen, B. Maehle, and D.K. Hole The formalin test in mice. Effect of the formalin concentration Pain 42 1990 235 242 (Pubitemid 20258908)
44. T.L. Sahley, and G.G. Berntson Antinociceptive effects of central and systemic administration of nicotine in the rat Psychopharmacol 65 1979 279 283 (Pubitemid 10194755)
45. G. Schechtmann, Z. Song, C. Ultenius, B.A. Meyerson, and B. Linderoth Cholinergic mechanisms involved in the pain relieving effect of spinal cord stimulation in a model of neuropathy Pain 139 2008 136 145
46. M. Shibata, T. Ohkubo, H. Takahashi, and R. Inoki Modified formalin test: characteristic biphasic response Pain 38 1989 347 352 (Pubitemid 19251258)
47. M.G. Shvekhgeimer Synthesis of heterocyclic compounds by the cyclization of isatin and its derivatives (review) Chem Heteroc Comp 32 1996 249 276
48. B.V. Silva, N.M. Ribeiro, A.C. Pinto, M.D. Vargas, and L.D. Dias Synthesis of ferrocenyl oxindole compounds with potential anticancer activity J Braz Chem Soc 19 2008 1244 1247
49. B.V. Silva, N.M. Ribeiro, M.D. Vargas, M. Lanznaster, J.W.M. Carneiro, and R. Krogh Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles Dalton Trans 39 2010 7338 7344
50. B.V. Silva, P.M. Esteves, and A.C. Pinto Chlorination of isatins with trichloroisocyanuric acid J Braz Chem Soc 22 2011 257 263
51. Z. Tabarelli, D.B. Berlese, P.D. Sauzem, M.A. Rubin, T.P. Missio, and M.V. Teixeira Antinociceptive effect of novel pyrazolines in mice Braz J Med Biol Res 37 2004 1531 1540 (Pubitemid 39369041)
52. M. Tanabe, K. Takasu, N. Kasuya, S. Shimizu, M. Honda, and H. Ono Role of descending noradrenergic system and spinal α2-adrenergic receptors in the effects of gabapentin on thermal and mechanical nociception after partial nerve injury in the mouse Br J Pharmacol 144 2005 703 714 (Pubitemid 40445619)
53. A. Tjølsen, J.H. Rosland, O.G. Berge, and K. Hole The increasing temperature hot-plate test: An improved test of nociception in mice and rats J Pharmacol Methods 25 1991 241 250
54. D.J. Tracey, and J.S. Walker Pain due to nerve damage: Are inflammatory mediators involved? Inflamm Res 44 1995 407 411
55. A. Tsølsen, O.C. Berge, S. Hunskaar, J.H. Rosland, and K. Hole The formalin test: An evaluation of the method Pain 51 1992 5 17
56. K.L. Vine, L. Matesic, J.M. Locke, M. Ranson, and D. Skropeta Cytotoxic and anticancer activities of isatin and its derivatives: A comprehensive review from 2000-2008 Anticancer Agents Med Chem 9 2008 397 414
57. B.J.R. Whittle Gastrointestinal effects of nonsteroidal anti-inflammatory drugs Fundam Clin Pharmacol 17 2003 301 313 (Pubitemid 36774165)
58. Y.F. Xie, F.Q. Huo, and J.S. Tang Cerebral cortex modulation of pain Acta Pharmacol Sin 30 2009 31 41
59. T.L. Yaksh, R. Dirksen, and G.J. Harty Antinociceptive effects of intrathecally injected cholinomimetic drugs in the rat and cat Eur J Pharmacol 117 1985 81 88 (Pubitemid 16204502)
60. G. Zapata-Sudo, L.B. Pontes, D. Gabriel, T.C.F. Mendes, N.M. Ribeiro, and A.C. Pinto Sedative-hypnotic profile of novel isatin ketals Pharmacol Biochem Behav 86 2007 678 685 (Pubitemid 46829321)
61. P.O. Zimer, R.L. Wynn, R.D. Ford, and F.G. Rudo Effect of hot plate temperature on the antinociceptive activity of mixed opioid agonist antagonist compounds Drug Dev Res 7 1986 277 280 (Pubitemid 16139688)
62. M. Zimmermann Ethical guidelines for investigation of experimental pain in conscious animals Pain 16 1983 109 110 (Pubitemid 13058546)