Comparative anticonvulsant activity of N-acetyl-1-aryl-6,7-dimethoxy-1,2,3, 4-tetrahydroisoquinoline derivatives in rodents

Pharmacology Biochemistry and Behavior

Volumn 77, Issue 1, 2004, Pages 85-94

  Ferreri, Guido ^a   Chimirri, Alba ^b   Russo, Emilio ^a   Gitto, Rosaria ^b   Gareri, Pietro ^a   De Sarro, Angela ^c   De Sarro, Giovambattista ^a  

^a UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

^c UNIVERSITY OF MESSINA   (Italy)

Author keywords

2,3 Benzodiazepines; AMPA kainate receptor antagonists; Audiogenic seizures; CFM 2; Chemoconvulsions; DBA 2 mice; Epilepsy; GYKI 52466; GYKI 53655; GYKI 53773; Maximal electroshock; N acetyl 1 aryl 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinolines; NBQX

Indexed keywords

1 (4 AMINOPHENYL) 3,4 DIHYDRO 4 METHYL 3 METHYLCARBAMOYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; 1 (4 AMINOPHENYL) 4 METHYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; 2,3 DIHYDROXY 6 NITRO 7 SULFAMOYLBENZOQUINOXALINE; 4 AMINOBUTYRIC ACID; 4 AMINOPYRIDINE; ACETIC ACID DERIVATIVE; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; ALPHA AMINO 5 TERT BUTYL 3 HYDROXY 4 ISOXAZOLEPROPIONIC ACID; ANTICONVULSIVE AGENT; BENZODIAZEPINE DERIVATIVE; CHLORINE; DIAZEPAM; KAINIC ACID; MERCAPTOPROPIONIC ACID; N METHYL DEXTRO ASPARTIC ACID; PENTETRAZOLE; PHENYL GROUP; PROPIONIC ACID DERIVATIVE; TALAMPANEL; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; ATOM; AUDIOGENIC SEIZURE; CLONIC SEIZURE; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; ELECTRIC SHOCK; EXPERIMENTAL MODEL; GABAERGIC SYSTEM; GENETIC SUSCEPTIBILITY; LETHALITY; MOUSE STRAIN; NEUROTRANSMISSION; NONHUMAN; PRIORITY JOURNAL; PROTECTION; SEIZURE; TONIC SEIZURE;

RODENTIA;

EID: 0347915541     PISSN: 00913057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pbb.2003.09.019     Document Type: Article

References (62)

1. Abraham K.E., McGinty J.F., Brewer K.L. The role of kainic acid/AMPA and metabotropic glutamate receptors in the regulation of opioid mRNA expression and the onset of pain-related behavior following excitotoxic spinal cord injury. Neuroscience. 104:2001;863-874.
2. Armand V., Rundfeldt C., Heinemann U. Effects of retigabine (D-23129) on different patterns of epileptiform activity induced by 4-aminopyridine in rat entorhinal cortex hippocampal slices. Naunyn-Schmiedeberg's Arch. Pharmacol. 359:1999;33-39.
3. Barreca M.L., Gitto R., Quartarone S., De Luca L., De Sarro G., Chimirri A. Pharmacophore modeling as an efficient tool in the discovery of novel noncompetitive AMPA receptor antagonists. J. Chem. Inf. Comput. Sci. 43:2003;651-655.
4. Bettler B., Mulle C. Review: neurotransmitter receptors II: AMPA and kainate receptors. Neuropharmacology. 34:1995;123-139.
5. Bleakman R., Schoepp D.D., Ballyk B., Bufton H., Sharpe E.F., Thomas K. et al. Pharmacological discrimination of GluR5 and GluR6 kainate receptor subtypes by (3S,4aR,6R,8aR)-6-[2-(1 (2)H-tetrazole-5-yl)ethyl] decahydroisdoquinoline-3 carboxylic-acid. Mol. Pharmacol. 49:1996;581-585.
6. Block F., Schwarz M. The depressant effect of GYKI 52466 on spinal reflex transmission in rats is mediated via non-NMDA and benzodiazepine receptors. Eur. J. Pharmacol. 256:1994;149-153.
7. Buchan A.M., Lesiuk H., Barnes K.A., Li H., Huang Z.G., Smith K.E.et al. AMPA antagonists: do they hold more promise for clinical stroke trials than NMDA antagonists? Stroke. 24:1993;I148-I152.
8. Chimirri A., De Sarro G.B., De Sarro A., Gitto R., Grasso S., Quartarone S.et al. 1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists. J. Med. Chem. 40:1997;1258-1269.
9. Chimirri A., Gitto R., Zappalà M. AMPA receptor antagonists. Expert Opin. Ther. Pat. 9:1999;557-570.
10. Clarke V.R., Collingridge G.L. Characterisation of the effects of, ATPA, a GLU(K5) receptor selective agonist, on excitatory synaptic transmission in area CA1 of rat hippocampal slices. Neuropharmacology. 42:2002;889-902.
11. Clarke V.R., Ballyk B.A., Hoo K.H., Mandelzys A., Pellizzari A., Bath C.P.et al. A hippocampal GluR5 kainate receptor regulating inhibitory synaptic transmission. Nature. 389:1997;599-603.
12. Cui C., Mayer M.L. Heteromeric kainate receptors formed by the coassembly of GluR5, GluR6, and GluR7. J. Neurosci. 19:1999;8281-8291.
13. De Sarro G.B., Croucher M.J., Meldrum B.S. Anticonvulsant actions of DS 103-282. Neuropharmacology. 23:1984;525-530.
14. De Sarro G.B., Meldrum B.S., Nisticò G. Anticonvulsant effects of some calcium entry blockers in DBA/2 mice. Br. J. Pharmacol. 93:1988;247-256.
15. De Sarro G.B., Ongini E., Bertorelli R., Aguglia U., De Sarro A. Excitatory amino acid neurotransmission through both NMDA and non-NMDA receptors is involved in the anticonvulsant activity of felbamate in DBA/2 mice. Eur. J. Pharmacol. 262:1994;11-19.
16. De Sarro G.B., Chimirri A., De Sarro A., Gitto R., Grasso S., Giusti P. et al. GYKI 52466 and related 2,3-benzodiazepines as anticonvulsant agents in DBA/2 mice. Eur. J. Pharmacol. 294:1995;411-422.
17. De Sarro G.B., Donato Di Paola E., Gareri P., Gallelli L., Scotto G., De Sarro A. Effects of some AMPA receptor antagonists on the development of tolerance in epilepsy-prone rats and in pentylenetetrazole kindled rats. Eur. J. Pharmacol. 368:1998;149-159.
18. De Sarro A., De Sarro G.B., Gitto R., Grasso S., Micale N., Zappalà M. Synthesis and anticonvulsant activity of new 2,3-benzodiazepines as AMPA receptor antagonists. Farmaco. 54:1999;178-187.
19. De Sarro G.B., Rizzo M., Spagnolo C., Gitto R., De Sarro A., Scotto G.et al. Anticonvulsant activity and plasma level of 2,3-benzodiazepin-4-ones (CFMs) in genetically epilepsy-prone rats. Pharmacol. Biochem. Behav. 4:1999;621-627.
20. De Sarro G., Ferreri G., Gareri P., Russo E., De Sarro A., Gitto R.et al. Comparative anticonvulsant activity of some 2,3-benzodiazepine derivatives in rodents. Pharmacol. Biochem. Behav. 74:2003;595-602.
21. Donevan S.D., Yamaguchi S.I., Rogawski M.A. Non-N-methyl-D-aspartate receptor antagonism by 3-N-substituted 2,3-benzodiazepines: relationship to anticonvulsant activity. J. Pharmacol. Exp. Ther. 271:1994;25-29.
22. Dreier J.P., Heinemann U. Late low magnesium-induced epileptiform activity in rat entorhinal cortex slices becomes insensitive to the anticonvulsant valproic acid. Neurosci. Lett. 119:1990;68-70.
23. Gitto R., Chimirri A., Zappalà M., De Sarro G.B., De Sarro A. Synthesis and pharmacological evaluation of 4-aryl-6,7-dimethoxyphtalazines as anticonvulsant agents. Med. Chem. Res. 10:2000;1-10.
24. Gitto R., Barreca M.L., De Luca L., De Sarro G., Ferreri G., Quartarone S.et al. Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. J. Med. Chem. 46:2003;197-200.
25. Gitto R., Orlando V., Quartarone S., De Sarro G., De Sarro A., Russo E. et al. Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives. J. Med. Chem. 46:2003;3758-3761.
26. Grasso S., De Sarro G., De Sarro A., Micale N., Zappala M., Puja G.et al. Synthesis and anticonvulsant activity of novel and potent 6,7- methylenedioxyphthalazin-1 (2H)-ones. J. Med. Chem. 43:2000;2851-2859.
27. Honorè T., Davies S.N., Drejer J., Fletcher E.J., Jacobsen P., Lodge D.et al. Quinoxalinediones: potent competitive non-NMDA glutamate receptor antagonists. Science. 241:1988;701-703.
28. Horton R.W., Meldrum B.S. Seizures induced by allylglicyne, 3-mercaptopropionic acid and 4-deoxy-pyridoxine in mice and photosensitive baboons, and different modes of inhibition of cerebral glutamic acid decarboxylase. Br. J. Pharmacol. 49:1973;52-63.
29. Jorgensen M., Tygesen C.K., Andersen P.H. Ionotropic glutamate receptors - focus on non-NMDA receptors. Pharmacol. Toxicol. 76:1995;312-319.
30. Lazzaro J.T., Paternain A.V., Lerma J., Chenard B.L., Ewing F.E., Huang J.et al. Functional characterization of CP-465,022, a selective, noncompetitive AMPA receptor antagonist. Neuropharmacology. 42:2002;143-153.
31. Lerma J., Morales M., Vicente M.A., Herreras O. Glutamate receptors of the kainate type and synaptic transmission. Trends Neurosci. 20:1997;9-12.
32. Li H., Rogawski M.A. GluR5 kainate receptor mediated synaptic transmission in rat basolateral amygdala in vitro. Neuropharmacology. 37:1998;1279-1286.
33. Litchfield J.T., Wilcoxon F. A simplified method of evaluating dose-effect experiments. J. Pharmacol. Exp. Ther. 96:1949;99-113.
34. Löscher W., Honack D. The behavioural effects of MK-801 in rats: involvement of dopaminergic, serotonergic and noradrenergic systems. Eur. J. Pharmacol. 215:1992;199-208.
35. Löscher W., Honack D. Over-additive anticonvulsant effect of memantine and NBQX in kindled rats. Eur. J. Pharmacol. 259:1994;R3-R5.
36. Löscher W., Schmidt D. Strategies in antiepileptic drug development: is rational drug design superior to random screening and structural variation? Epilepsy Res. 17:1994;95-134.
37. Löscher W., Lehmann H., Behl B., Seemann D., Teschendorf H.J., Hofmann H.P.et al. A new pyrrolyl-quinoxalinedione series of non-NMDA glutamate receptor antagonists: pharmacological characterization and comparison with NBQX and valproate in the kindling model of epilepsy. Eur J. Neurosci. 11:1999;250-262.
38. Mulle C., Sailer A., Perez-Otano I., Dickinson-Anson H., Castillo P.E., Bureau I.et al. Altered synaptic physiology and reduced susceptibility to kainate-induced seizures in GluR6-deficient mice. Nature. 392:1998;601-605.
39. O'Neill M.J., Bond A., Ornstein P.L., Ward M.A., Hicks C.A., Hoo K.et al. Decahydroisoquinolines: novel competitive AMPA/kainate antagonists with neuroprotective effects in global cerebral ischaemia. Neuropharmacology. 37:1998;1211-1222.
40. Parsons C.G., Danysz W., Quack G., Hartmann S., Lorenz B., Wollenburg C.et al. Novel systemically active antagonists of the glycine site of the N-methyl-D-aspartate receptor: electrophysiological, biochemical and behavioral characterization. J. Pharmacol. Exp. Ther. 283:1997;1264-1275.
41. Paternain A.V., Herrera M.T., Nieto M.A., Lerma J. GluR5 and GluR6 kainate receptor subunits coexist in hippocampal neurons and coassemble to form functional receptors. J. Neurosci. 20:2000;196-205.
42. Pei X., Sturgess M.A., Valenzuela C.F., Maccecchini M.L. Allosteric modulators of AMPA receptor: novel 6-substituted dihydrophthalazines. Bioorg. Med. Chem. Lett. 9:1999;539-542.
43. Pelletier J.C., Hesson D.P., Jones K.A., Costa A.M. Substituted 1,2-dihydrophthalazines: potent, selective, and noncompetitive inhibitors of the AMPA receptor. J. Med. Chem. 39:1996;343-346.
44. Rogawski M.A. Therapeutic potential of excitatory amino acid antagonists: channel blockers and 2,3-benzodiazepines. Trends Pharmacol. Sci. 14:1993;325-331.
45. Rogawski M.A., Gryder D., Castaneda D., Yonekawa W., Banks M.K., Lia H. GluR5 kainate receptors, seizures, and the amygdala. Ann. N. Y. Acad. Sci. 985:2003;150-162.
46. Sailer A., Swanson G.T., Perez-Otano I., O'Leary L., Malkmus S.A., Dyck R.H.et al. Generation and analysis of GluR5 (Q636R) kainate receptor mutant mice. J. Neurosci. 19:1999;8757-8764.
47. Smith S.E., Durmuller N., Meldrum B.S. The non-N-methyl-D-aspartate receptor antagonist, GYKI 52466 and NBQX are anticonvulsant in two animal models of reflex epilepsy. Eur. J. Pharmacol. 201:1991;179-183.
48. Smolders I., Bortolotto Z.A., Clarke V.R., Warre R., Khan G.M., O'Neill M.J.et al. Antagonists of GLU (K5)-containing kainate receptors prevent pilocarpine-induced limbic seizures. Nat. Neurosci. 5:2002;796-804.
49. Spyker D.A., Lynch C., Shabanowitz J., Sinn J.A. Poisoning with 4-aminopyridine: report of three cases. Clin. Toxicol. 16:1980;487-497.
50. Stensbøl T.B., Borre L., Johansen T.N., Egebjerg J., Madsen U., Ebert B.et al. Resolution, absolute stereochemistry and molecular pharmacology of the enantiomers of ATPA. Eur. J. Pharmacol. 380:1999;153-162.
51. Sutcliffe M.J., Wo Z.G., Oswald R.E. Three-dimensional models of non-NMDA glutamate receptors. Biophys. J. 70:1996;1575-1589.
52. Swinyard E.A., Woodhead J.M. Experimental detection, quantification and evaluation of anticonvulsants. Woodbury D.M., Penry J.K., Pippenger C.E. Epileptic drugs. 1982;111-126 Raven Press, New York.
53. Tarnawa I., Farkas S., Berzsenyi P., Pataki A., Andrasi F. Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466. Eur. J. Pharmacol. 167:1989;193-199.
54. Turski L., Jacobsen P., Honore T., Stephens D.N. Relief of experimental spasticity and anxiolytic/anticonvulsant actions of the alpha-amino-3-hydroxy-5- methyl-4-isoxazolepropionate antagonist 2,3-dihydroxy-6-nitro-7-sulfamoyl benzo (F) quinoxaline. J. Pharmacol. Exp. Ther. 260:1992;742-747.
55. Vizi E.S., Mike A., Tarnawa I. 2,3-Benzodiazepines (GYKI 52466 analogues): negative allosteric modulators of AMPA receptors. CNS Drug Rev. 2:1996;91-126.
56. Welch W.M., Ewing F.E., Huang J., Menniti F.S., Pagnozzi M.J., Kelly K. et al. Atropisomeric quinazolin-4-one derivatives are potent noncompetitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists. Bioorg. Med. Chem. Lett. 11:2001;177-181.
57. Yamaguchi S., Rogawski M.A. Effects of anticonvulsant drugs on 4-aminopyridine-induced seizure in mice. Epilepsy Res. 11:1992;9-16.
58. Yamaguchi S., Donevan S.D., Rogawski M.A. Anticonvulsant activity of AMPA/kainate antagonists: comparison of GYKI 52466 and NBQX in maximal electroshock and chemoconvulsant seizure models. Epilepsy Res. 15:1993;179-184.
59. Yonekawa W.D., Kapetanovic I.M., Kupferberg H.J. The effects of D-23129 (ADD230001) and standard anticonvulsant on the paired-pulse paradigm in rat hippocampus in vitro (abstract). Soc. Neurosci. Abstr. 21:1995;R2117.
60. Yonekawa W.D., Kapetanovic I.M., Kupferberg H.J. The effects of anticonvulsant agents on 4-aminopyridine-induced epileptiform activity in rat hippocampus in vitro. Epilepsy Res. 20:1995;137-150.
61. Zappalà M., Gitto R., Bevacqua F., Quartarone S., Chimirri A., Rizzo M.et al. Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-(1,2,4)triazolo (4,5-c) (2,3)benzodiazepin-3 (2H)-ones. J. Med. Chem. 43:2000;4834-4839.
62. 2+ induced epileptiform activity in rat temporal cortex slices: development of pharmacoresistant epileptiform activity (abstract). Pflugers Archiv. 418:1991;R10.