T-type channel blocking properties and antiabsence activity of two imidazo[1,2-b]pyridazine derivatives structurally related to indomethacin

Neuropharmacology

Volumn 56, Issue 3, 2009, Pages 637-646

  Rimoli, Maria Grazia ^a   Russo, Emilio ^b   Cataldi, Mauro ^c   Citraro, Rita ^b   Ambrosino, Paolo ^c   Melisi, Daniela ^a   Curcio, Annalisa ^a   De Lucia, Salvatore ^a   Patrignani, Paola ^d   De Sarro, Giovambattista ^b   Abignente, Enrico ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^c University School of Medicine Federico II   (Italy)

^d UNIVERSITY OF CHIETI   (Italy)

Author keywords

Absence epilepsy; Imidazopyridazines; Indomethacin; T type channel

Indexed keywords

6 METHOXY 2 PHENYLIMIDAZO[1,2 B]PYRIDAZINE 3 CARBOXYLIC ACID; 7 METHYL 2 PHENYLIMIDAZO[1,2 B]PYRIDAZINE 3 CARBOXYLIC ACID; CALCIUM CHANNEL T TYPE; CARBOXYLIC ACID DERIVATIVE; IMIDAZO[1,2 B]PYRIDAZINE DERIVATIVE; INDOMETACIN; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSENCE; ANTICONVULSANT THERAPY; ARTICLE; CALCIUM TRANSPORT; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; DRUG POTENCY; FEMALE; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; MALE; MEMBRANE DEPOLARIZATION; NORMAL HUMAN; PATCH CLAMP; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SEIZURE; THALAMUS NUCLEUS; WISTAR ALBINO GLAXO RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTICONVULSANTS; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS, T-TYPE; CELLS, CULTURED; DISEASE MODELS, ANIMAL; ELECTROENCEPHALOGRAPHY; EPILEPSY, ABSENCE; IMIDAZOLES; INDOMETHACIN; MALE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PYRIDAZINES; RANDOM ALLOCATION; RATS; RATS, INBRED STRAINS;

EID: 58749085881     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2008.11.003     Document Type: Article

References (59)

1. Abignente E. Etudes d'imidazo[1,2-a]pyridines et d'analogues douées d'activité anti-inflammatoire. Actualités de Chimie Thérapeutique 18 (1991) 193-214
2. Abignente E., Arena F., Luraschi E., De Caprariis P., Marmo E., Vitagliano S., and Donnoli D. Research on heterocyclic compounds. XXVI. Antiinflammatory and related activities of some 2-phenylimidazo[1,2-b]pyridazines. Research Communications in Chemical Pathology and Pharmacology 67 (1990) 43-54
3. Abignente E., Arena F., Luraschi E., Saturnino C., Marmo E., Berrino L., and Donnoli D. Research on heterocyclic compounds. XXVII. Synthesis and antiinflammatory activity of 2-phenylimidazo[1,2-b]pyridazine-3-carboxylic acids. Farmaco 45 (1990) 1075-1087
4. Breder C.D., Dewitt D., and Kraig R.P. Characterization of inducible cyclooxygenase in rat brain. Journal of Comparative Neurology 355 (1995) 296-315
5. Burke A., Smyth E.M., and FitzGerald G.A. Analgesic-antipyretic and antiinflammatory drugs; pharmacotherapy of gout. In: Brunton L., Lazo J., and Parker K. (Eds). Goodman & Gilman's The Pharmacological Basis of Therapeutics. 11th ed. (2006), McGrawHill Columbus, OH (USA) 671-716
6. 2 regulates membrane excitability and synaptic transmission in hippocampal CA1 pyramidal neurons. Journal of Neurophysiology 93 (2005) 929-941
7. 2+ channels by ethosuximide is not the whole story. Epilepsy Currents 2 (2002) 53-56
8. Coulter D.A., Huguenard J.R., and Prince D.A. Specific petit mal anticonvulsants reduce calcium currents in thalamic neurons. Neuroscience Letters 98 (1989) 74-78
9. Coulter D.A., Huguenard J.R., and Prince D.A. Characterization of ethosuximide reduction of low-threshold calcium current in thalamic neurons. Annals of Neurology 25 (1989) 582-593
10. Coulter D.A., Huguenard J.R., and Prince D.A. Differential effects of petit mal anticonvulsants and convulsants on thalamic neurons: calcium current reduction. British Journal of Pharmacology 100 (1990) 800-806
11. De Gaetano G., Cerletti C., Dejana E., and Latin R. Pharmacology of platelet inhibition in humans: implications of the salicylate-aspirin interaction. Circulation 72 (1985) 1185-1193
12. Depoortere H., Françon D., van Luijtelaar E.L., Drinkenburg W.H., and Coenen A.M. Differential effects of midazolam and zolpidem on sleep-wake states and antiepileptic activity inWAG/Rij rats. Pharmacology, Biochemistry, and Behavior 51 (1995) 571-576
13. Dhir A., and Kulkarni P.S. Rofecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor potentiates the anticonvulsant activity of tiagabine against pentylenetetrazol-induced convulsions in mice. Inflammopharmacology 14 (2006) 222-225
14. Dhir A., Naidu P.S., and Kulkarni S.K. Effect of cyclooxygenase inhibitors on pentylenetetrazol (PZT)-induced convulsions. Possible mechanism of action. Progress in Neuropsychopharmacology & Biological Psychiatry 30 (2006) 1478-1485
15. 2-induced inhibition of potassium currents in rat sensory neurones. The Journal of Physiology 516 (1999) 163-178
16. Gray L.S., and Macdonald T.L. The pharmacology and regulation of T type calcium channels: new opportunities for unique therapeutics for cancer. Cell Calcium 40 (2006) 115-120
17. Gund R., and Shen T.Y. A model for the prostaglandin synthetase cyclooxygenation site and its inhibition by anti-inflammatory arylacetic acids. Journal of Medicinal Chemistry 20 (1977) 1146-1152
18. Hanif R., Pittas A., Feng Y., Koutsos M.I., Qiao L., Staiano-Coico L., Shiff S.I., and Rigas B. Effects of nonsteroidal anti-inflammatory drugs on proliferation and on induction of apoptosis in colon cancer cells by a prostaglandin-independent pathway. Biochemical Pharmacology 52 (1996) 237-245
19. Kajiwara K., Nagawawa H., Shimizu-Nishikawa S., Ookuri T., Kimura M., and Sugaya E. Molecular characterization of seizure-related genes isolated by differential screening. Biochemical and Biophysical Research Communications 219 (1996) 795-799
20. Kaufmann W.E., Worley P.F., Pegg J., Bremer M., and Isakson P. COX-2, a synaptically induced enzyme, is expressed by excitatory neurons at postsynaptic sites in rat cerebral cortex. Proceedings of the National Academy of Sciences of the United States of America 93 (1996) 2317-2321
21. 2+ channels. Neuron 31 (2001) 35-45
22. Kopp E., and Ghosh S. Inhibition of NF-kB by sodium salicylate and aspirin. Science 265 (1994) 956-959
23. Kovacs Z., Kekesi K.A., Szilagyi N., Abraham I., Szekacs D., Kiraly N., Papp E., Csaszar I., Szego E., Barabas K., Peterfy H., Erdei A., Bartfai T., and Juhasz G. Facilitation of spike-wave discharge activity by lipopolysaccharides in Wistar Albino Glaxo/Rijswijk rats. Neuroscience 140 (2006) 731-742
24. Liantonio A., Giannuzzi V., Picollo A., Babini E., Pusch M., and Conte Camerino D. Niflumic acid inhibits chloride conductance of rat skeletal muscle by direct inhibiting the CLC-1 channel and by increasing intracellular calcium. British Journal of Pharmacology 150 (2007) 235-247
25. van Luijtelaar E.L., and Coenen A.M. Electrophysiological evaluation of three paradoxical sleep deprivation techniques in rats. Physiology and Behavior 36 (1986) 603-609
26. Luraschi E., Arena F., Sacchi A., Laneri S., Abignente E., Avallone L., D'Amico M., Berrino L., and Rossi F. Research on heterocyclic compounds. XXXVIII. Synthesis and pharmacological activity of imidazo[1,2-b]pyridazine-2-carboxylic derivatives. Farmaco 52 (1997) 213-217
27. Malykhina A.P., Shoeb F., and Akbarali H.I. Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes. European Journal of Pharmacology 11 (2002) 269-277
28. Matasic R., Dietz A.B., and Vuk-Pavlovic S. Cyclooxygenase-independent inhibition of dendritic cell maturation by aspirin. Immunology 101 (2000) 53-60
29. Mehta J.L., Lawson D.L., and Nichols W.W. Attenuated coronary relaxation after reperfusion: effects of superoxide dismutase and TXA2 inhibitor U-63557A. American Journal of Physiology. Heart Circulation Physiology (1989) H1240-H1246
30. Meshram H.M., Reddy P.N., Sadashiv K., and Yadav J.S. Amberlyst-15-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides. Tetrahedron Letters 46 (2005) 623-626
31. Murakami H., and Castle R.N. The synthesis of imidazo[4,5-c]- and v-triazolo[4,5-c]-pyridazines. Journal of Heterocyclic Chemistry 4 (1967) 555
32. Nicol G.D., Vasko M.R., and Evans A.R. Prostaglandins suppress an outward potassium current in embryonic rat sensory neurons. Journal of Neurophysiology 77 (1997) 167-176
33. O'Kane P.D., Queen L.R., Ji Y., Reebye V., Stratton P., Jackson G., and Ferro A. Aspirin modifies nitric oxide synthase activity in platelets: effects of acute versus chronic aspirin treatment. Cardiovascular Research 59 (2003) 152-159
34. Panner A., and Wurster R.D. T-type calcium channels and tumor proliferation. Cell Calcium 40 (2006) 253-259
35. + currents in rat dorsal root ganglion neurons. Brain Research 1148 (2007) 53-61
36. Patrignani P., Panara M.R., Greco A., Fusco O., Natoli C., Iacobelli S., Cipolline F., Ganci A., Creminon C., Maclouf J., and Patrono C. Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases. Journal of Pharmacology and Experimental Therapeutics 271 (1994) 1705-1712
37. 2 production in healthy subjects. Thrombosis Research 17 (1980) 317-327
38. Paxinos G., and Watson C. The Rat Brain in Stereotaxic Coordinates. fourth ed. (1998), Academic Press, San Diego, CA, USA
39. Peretz A., Degani N., Nachman R., Uziyel Y., Gibor G., Shabat D., and Attali B. Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties. Molecular Pharmacology 67 (2005) 1053-1066
40. Pierce J.W., Read M.A., Ding H., Luscinskas F.W., and Collins T. Salicylates inhibit IκB-α phosphorylation, endothelial-leukocyte adhesion molecule expression, and neutrophil transmigration. Journal of Immunology 156 (1996) 3961-3969
41. Posner E.B., Mohamed K., and Marson A.G. Ethosuximide, sodium valproate or lamotrigine for absence seizures in children and adolescents. Cochrane Database of Systematic Reviews 4 (2005) Art. No.: CD003032
42. Rigas B., and Kashfi K. Cancer prevention: a new era beyond cyclooxygenase-2. Journal of Pharmacology and Experimental Therapeutics 314 (2005) 1-8
43. Russo E., Constanti A., Ferreri G., Citraro R., and De Sarro G. Nifedipine affects the anticonvulsant activity of topiramate in various animal models of epilepsy. Neuropharmacology 46 (2004) 865-878
44. Sakurada S., Kato T., and Okamoto T. Induction of cytokines and ICAM-1 by proinflammatory cytokines in primary rheumatoid synovial fibroblasts and inhibition by N-acetyl-l-cysteine and aspirin. International Immunology 8 (1996) 1483-1493
45. 2+ channels as therapeutic targets in the nervous system. Current Opinion in Pharmacology 8 (2008) 33-41
46. Song I., Kim D., Choi S., Sun M., and Shin H.S. Role of the alpha1G T-type calcium channel in spontaneous absence seizures in mutant mice. Journal of Neuroscience 24 (2004) 5249-5257
47. 2+ channel alpha1G. Journal of General Physiology 124 (2004) 225-238
48. Tandon M., Anuradha K., and Pandhi P. Evaluation of antiepileptic activity of aspirin in combination with newer antiepileptic lamotrigine in mice. Methods and Findings in Experimental and Clinical Pharmacology 25 (2003) 607-610
49. Tegeder I., Pfeilschifter J., and Geisslinger G. Cyclooxygenase-independent actions of cyclooxygenase inhibitors. FASEB Journal 15 (2001) 2057-2072
50. Tegeder I., Niederberger E., Israr E., Gühring H., Brune K., Euchenhofer C., Grösch S., and Geisslinger G. Inhibition of NF-κB and AP-1 activation by R- and S-flurbiprofen. FASEB Journal 15 (2001) 2-4
51. Tocco G., Freire-Moar J., Schreiber S.S., Sakhi S.H., Aisen P.S., and Pasinetti G.M. Maturational regulation and regional induction of cyclooxygenase-2 in rat brain: implications for Alzheimer's disease. Experimental Neurology 144 (1997) 339-349
52. 2+ channels in the heart. Cell Calcium 40 (2006) 205-220
53. Visioli F., Rodriguez de Turco E.B., Kreisman N.R., and Bazan N.G. Membrane lipid degradation is related to interictal cortical activity in a series of seizures. Metabolic Brain Disease 9 2 (1994 Jun) 161-170
54. Visioli F., Rihn L.L., Rodriguez de Turco E.B., Kreisman N.R., and Bazan N.G. Free fatty acid and diacylglycerol accumulation in the rat brain during recurrent seizures is related to cortical oxygenation. Journal of Neurochemistry 61 (1993) 1835-1842
55. Voilley N., de Weille J., Mamet J., and Lazdunski M. Nonsteroid anti-inflammatory drugs inhibit both the activity and the inflammation-induced expression of acid-sensing ion channels in nociceptors. Journal of Neuroscience 21 (2001) 8026-8033
56. Yamagata K., Andreasson K.I., Kaufmann W.E., Barnes C.A., and Worley P.F. Expression of a mitogen-inducible cyclooxygenase in brain neurons: regulation by synaptic activity and glucocorticoids. Neuron 11 (1993) 371-386
57. Yin M.J., Yamamoto Y., and Gaynor R.B. The anti-inflammatory agents aspirin and salicylate inhibit the activity of IκB kinase-β. Nature 396 (1998) 77-80
58. Zhang Y., Cribbs L.L., and Satin J. Arachidonic acid modulation of alpha1H, a cloned human T-type calcium channel. American Journal of Physiology. Heart and Circulatory Physiology 278 (2000) H184-H193
59. Zhang Y., Tao J., Huang H., Ding G., Cheng Y., and Sun W. Effects of celecoxib on voltage-gated calcium channel currents in rat pheochromocytoma (PC12) cells. Pharmacological Research 56 (2007) 267-274