A novel dihydro-pyrazolo(3,4d)(1,2,4)triazolo(1,5a)pyrimidin-4-one (AJ23) is an antagonist at adenosine A1 receptors and enhances consolidation of step-down avoidance

Behavioural Brain Research

Volumn 234, Issue 2, 2012, Pages 184-191

  Harvey, Alan L ^a   Young, Louise C ^a   Kornisiuk, Edgar ^b   Snitcofsky, Marina ^b   Colettis, Natalia ^b   Blanco, Carlos ^b   Jerusalinsky, Diana ^b   Jamieson, Andrew G ^c   Hartley, Richard C ^c   Stone, Trevor W ^d  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^c UNIVERSITY OF GLASGOW   (United Kingdom)

^d UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

A1 receptors; Adenosine; Hippocampus; Non xanthine antagonists; Purine receptors

Indexed keywords

7 METHYL 1 PHENYL 1,8 DIHYDROPYRAZOLO (3,4D)(1,2,4) TRIAZOLO (1,5A) PYRIMIDIN 4 ONE; ADENOSINE A1 RECEPTOR; AJ 23; NOOTROPIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AVOIDANCE BEHAVIOR; BINDING AFFINITY; COGNITIVE DEFECT; CONTROLLED STUDY; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; EXCITATORY POSTSYNAPTIC POTENTIAL SUMMATION; MALE; MEMORY CONSOLIDATION; NONHUMAN; PRIORITY JOURNAL; RAT; TASK PERFORMANCE;

ADENOSINE; ANALYSIS OF VARIANCE; ANIMALS; AVOIDANCE LEARNING; CA1 REGION, HIPPOCAMPAL; CHO CELLS; CRICETINAE; CRICETULUS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG ADMINISTRATION SCHEDULE; DRUG INTERACTIONS; ELECTRIC STIMULATION; EXCITATORY POSTSYNAPTIC POTENTIALS; HEK293 CELLS; HETEROCYCLIC COMPOUNDS, 3-RING; HUMANS; INHIBITION (PSYCHOLOGY); MALE; PROTEIN BINDING; PURINERGIC P1 RECEPTOR ANTAGONISTS; PYRIMIDINES; RATS; RATS, WISTAR; REACTION TIME; RETENTION (PSYCHOLOGY); STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES; TRIAZOLES; TRITIUM; XANTHINES;

EID: 84864042714     PISSN: 01664328     EISSN: 18727549     Source Type: Journal    
DOI: 10.1016/j.bbr.2012.06.023     Document Type: Article

References (59)

1. Peng S., Zhang Y., Zhang J.N., Wang H., Ren B.X. Glutamate receptors and signal transduction in learning and memory. Molecular Biology Reports 2001, 38:453-460.
2. Winters B.D., Bussey T.J. Glutamate receptors in perirhinal cortex mediate encoding, retrieval and consolidation of object recognition memory. Journal of Neuroscience 2005, 25:4243-4251.
3. Blokland A. Acetylcholine: a neurotransmitter for learning and memory. Brain Research Reviews 1996, 21:285-300.
4. Stone T.W. Adenosine receptors and their pharmacological roles. Advances in Drug Research 1989, 18:292-430.
5. Ribeiro J.A., Sebastiao A.M., de Mendonca A. Adenosine receptors in the nervous system: pathophysiological implications. Progress in Neurobiology 2002, 68:377-392.
6. Schingnitz G., Kufner-Muhl U., Ensinger H., Lehr E., Kuhn F.J. Selective A1 antagonists for treatment of cognitive deficits. Nucleosides and Nucleotides 1991, 10:1067-1076.
7. Kopf S.R., Melani A., Pedata F., Pepeu G. Adenosine and memory storage: effect of A(1) and A(2) receptor antagonists. Psychopharmacology 1999, 146:214-219.
8. Stone T.W., Nikbakht M.R., O'Kane E.M. Adenosine and purines. Memories are made of these: from messengers to molecules 2004, 196-223. Kluwer/Plenum Press, [Chapter 29]. G. Riedel, B. Platt (Eds.).
9. Normile H.J., Barraco R.A. N6-cyclopentyladenosine impairs passive avoidance retention by selective action at A1 receptors. Brain Research Bulletin 1991, 27:101-104.
10. Ohno M., Watanabe S. Working memory failure by stimulation of hippocampal adenosine A1 receptors in rats. Neuroreport 1996, 7:3013-3016.
11. Zarrindast M.R., Shafaghi B. Effects of adenosine receptor agonists and antagonists in acquisition of passive avoidance learning. European Journal of Pharmacology 1994, 256:233-239.
12. Corodimas K.P., Tomita H. Adenosine A1 receptor activation selectively impairs the acquisition of contextual fear conditioning in rats. Behavioral Neuroscience 2001, 115:1283-1290.
13. Pereira G.S., Rossato J.I., Sarkis J.J.F., Cammarota M., Bonan C.D., Izquierdo I. Activation of adenosine receptors in the posterior cingulate cortex impairs memory retrieval in the rat. Neurobiol Learning Memory 2005, 83:217-223.
14. Pereira G.S., Souza T.M.E., Vinade E.R.C., Choi H., Rodrigues C., Battastini A.M.O., et al. Blockade of adenosine A, receptors in the posterior cingulate cortex facilitates memory in rats. European Journal of Pharmacology 2002, 437:151-154.
15. Jacobson K.A., Gao Z.-G. Adenosine receptors as therapeutic targets. Nature Reviews 2006, 5:247-257.
16. Schwabe U., Ukena D., Lohse M.J. Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn-Schmiedeberg's Archives of Pharmacology 1985, 330:212-221.
17. Jacobson K.A., Delacruz R., Schulick R., Kiriasis L., Padgett W., Pfleiderer W., et al. 8-Substituted xanthines as antagonists at A1-adenosine and A2-adenosine receptors. Biochemical Pharmacology 1988, 37:3653-3661.
18. Shamim M.T., Ukena D., Padgett W.L., Hong O., Daly J.W. 8-Aryl-1,3-dipropylxanthines and 8-cycloalkyl-1,3-dipropylxanthines - further potent and selective antagonists for a1-adenosine receptors. Journal of Medicinal Chemistry 1988, 31:613-617.
19. Shimada J., Suzuki F., Nonaka H., Ishii A. 8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for adenosine-A1-receptors. Journal of Medicinal Chemistry 1992, 35:924-930.
20. Kiesman W.F., Zhao J., Conlon P.R., Dowling J.E., Petter R.C., Lutterodt F., et al. Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A(1) receptor antagonists. Journal of Medicinal Chemistry 2006, 49:7119-7131.
21. Van Galen P.J.M., Ijzerman A.P., Soudijn W. Xanthine-7-ribosides as adenosine-A1 receptor antagonists - further evidence for adenosines anti mode of binding. Nucleosides and Nucleotides 1990, 9:275-291.
22. Van Der Wenden E.M., Ijzerman A.P., Soudijn W. A steric and electrostatic comparison of 3 models for the agonist antagonist binding-site on the adenosine-a1-receptor. Journal of Medicinal Chemistry 1992, 35:629-635.
23. Muller C.E., Geis U., Grahner B., Lanzner W., Eger K. Chiral pyrrolo [2,3-d]-pyrimidine and pyrimido[4,5-b]indole derivatives: structure-activity relationships of potent, highly stereoselective A(1)-adenosine receptor antagonists. Journal of Medicinal Chemistry 1996, 39:2482-2491.
24. Van Calenbergh S., von Frijtag J.K., Kunzel D., Blaton N.M., Peeters O.M., Rozenski J., et al. N-6-cyclopentyl-3'-substituted-xylofuranosyladenosines: a new class of non-xanthine adenosine A(1) receptor antagonists. Journal of Medicinal Chemistry 1997, 40:3765-3772.
25. Poulsen S.A., Quinn R.J. Synthesis and structure-activity relationship of pyrazolo[3,4-d]pyrimidines: potent and selective adenosine A(1) receptor antagonists. Journal of Medicinal Chemistry 1996, 39:4156-4161.
26. Kuroda S., Akahane A., Itani H., Nishimura S., Durkin K., Tenda Y., et al. Novel adenosine A(1) receptor antagonists. Synthesis and structure-activity relationships of a novel series of 3-(2-cyclohexenyl-3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-alpha]pyridines. Bioorganic and Medicinal Chemistry 2000, 8:55-64.
27. El-Sherbeny M.A., El-Ashmawy M.B., El-Subbagh H.I., El-Emam A.A., Badria F.A. Synthesis, antimcirobial and antiviral evaluation of certain thienopyrimidine derivatives. European Journal of Medicinal Chemistry 1995, 30:445-449.
28. Schmidt P., Druey J. Heilmittelchemische Untersuchungen In Der Heterocyclischen Reihe.14. Pyrazolo-(3,4-D)-pyrimidine. Helvetica Chimica Acta 1956, 39:986-991.
29. Kopp M., Lancelot J.-C., Dallemagne P., Rault S. Synthesis of novel pyrazolopyrrolopyrazines, potential analogs of sildenafil. Journal of Heterocyclic Chemistry 2001, 38:1045-1050.
30. Hayallah A.M., Sandoval-Ramirez J., Reith U., Schobert U., Preiss B., Schumacher B., et al. 1,8-Disubstituted xanthine derivatives: synthesis of potent A(2B)-selective adenosine receptor antagonists. Journal of Medicinal Chemistry 2002, 45:1500-1510.
31. Yan L., Müller C. Preparation, properties, reactions and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulphonic acid prodrugs with peroral bioavailability. Journal of Medicinal Chemistry 2004, 47:1031-1043.
32. Stone T.W. Kynurenic acid blocks nicotinic synaptic transmission to hippocampal interneurons in young rats. The European Journal of Neuroscience 2007, 25:2656-2665.
33. Ferguson A.L., Stone T.W. TI Glutamate-induced depression of EPSP-spike coupling in rat hippocampal CA1 neurons and modulation by adenosine receptors. The European Journal of Neuroscience 2010, 31:1208-1218.
34. Kornisiuk E., Snitcofsky M., Blanco C., Harvey A.L., Stone T.W., Jerusalinsky D. Memory impairment in rats by intrahippocampal administration of the serine protease subtilisin. Behavioural Brain Research 2011, 219:63-67.
35. Paxinos G., Watson C. The rat brain in stereotaxic coordinates 2009, Elsevier, London. Sixth ed.
36. Yang S.C., Chiu T.H., Yang H.W., Min M.Y. Presynaptic adenosine A(1) receptors modulate excitatory synaptic transmission in the posterior piriform cortex in rats. Brain Research 2007, 1156:67-79.
37. Fontanez D.E., Porter J.T. Adenosine A(1) receptors decrease thalamic excitation of inhibitory and excitatory neurons in the barrel cortex. Neuroscience 2006, 137:1177-1184.
38. Cunha R.A., Sebastiao A.M., Ribeiro J.A. Inhibition by ATP of hippocampal synaptic transmission requires localized extracellular catabolism by ecto-nucleotidases into adenosine and channeling to adenosine A(1) receptors. Journal of Neuroscience 1998, 18:1987-1995.
39. Rodrigues R.J., Canas P.M., Lopes L.V., Oliveira C.R., Cunha R.A. Modification of adenosine modulation of acetylcholine release in the hippocampus of aged rats. Neurobiology of Aging 2008, 29:1597-1601.
40. Arrigoni E., Chamberlin N.L., Saper C.B., McCarley R.W. Adenosine inhibits basal forebrain cholinergic and noncholinergic neurons in vitro. Neuroscience 2006, 140:403-413.
41. Van Dort C.J., Baghdoyan H.A., Lydic R. Adenosine A(1) and A(2A) receptors in mouse prefrontal cortex modulate acetylcholine release and behavioral arousal. Journal of Neuroscience 2009, 29:871-881.
42. Cunha R.A., Milusheva E., Vizi E.S., Ribeiro J.A., Sebastiao A.M. Excitatory and inhibitory effects of a(1) and a(2a) adenosine receptor activation on the electrically-evoked [H-3] acetylcholine-release from different areas of the rat hippocampus. Journal of Neurochemistry 1994, 63:207-214.
43. Sperlagh B., Zsilla G., Vizi E.S. K-ATP channel blockers selectively interact with A(1)-adenosine receptor mediated modulation of acetylcholine release in the rat hippocampus. Brain Research 2001, 889:63-70.
44. Quarta D., Ferre S., Solinas M., You Z.B., Hockemeyer J., Popoli P., et al. Opposite modulatory roles for adenosine A(1) and A(2A) receptors on glutamate and dopamine release in the shell of the nucleus accumbens. Effects of chronic caffeine exposure. Journal of Neurochemistry 2004, 88:1151-1158.
45. Carter A.J., O'Connor W.T., Carter M.J., Ungerstedt U. Caffeine enhances acetylcholine-release in the hippocampus in vivo by a selective interaction with adenosine a(1) receptors. The Journal of Pharmacology and Experimental Therapeutics 1995, 273:637-642.
46. Pitsikas N., Borsini F. The adenosine A1 receptor antagonist BIIP 20 counteracts scopolamine-induced behavioural deficits in the passive avoidance task in the rat. European Journal of Pharmacology 1997, 328:19-22.
47. Suzuki F., Shimada J., Shiozaki S., Ichikawa S., Ishii A., Nakamura J., et al. Adenosine A1 antagonists: SAR on amelioration against scopolamine or N6-PIA-induced cognitive disturbance. Journal of Medicinal Chemistry 1993, 36:2508-2518.
48. Botton P.H., Costa M.S., Ardais A.P., Mioranzza S., Souza D.O., da Rocha J.B.T., et al. Caffeine prevents disruption of memory consolidation in the inhibitory avoidance and novel object recognition tasks by scopolamine in adult mice. Behavioural Brain Research 2010, 214:254-259.
49. Riedel W., Hogervorst E., Leboux R., Verhey F., Vanpraag H., Jolles W. Caffeine attenuates scopolamine-induced memory impairment in humans. Psychopharmacology 1995, 122:158-168.
50. Vizi E.S., Knoll J. Inhibitory effect of adenosine and related nucleotides on release of acetylcholine. Neuroscience 1976, 1:391-398.
51. Porsolt R.D., Roux S., Wettstein J.G. Animals models of dementia. Drug Development Research 1995, 35:214-229.
52. Irwin S. Comprehensive observational assessment: a systematic quantitative procedure for assessing the behavioral and physiologic state of the mouse. Psychopharmacologia 1968, 13:222-257.
53. Sperlagh B., Vizi E.S. The role of extracellular adenosine in chemical neurotransmission in the hippocampus and basal ganglia: pharmacological and clinical aspects. Current Topics in Medicinal Chemistry 2011, 11:1034-1046.
54. Stone T.W., Stefania C., Abbracchio M. Adenosine receptors and neurological disease: neuroprotection and neurodegeneration. Handbook of Experimental Pharmacology 2009, 193:535-587.
55. Baraldi P.G., Tabrizi M.A., Romagnoli R., Fruttarolo F., Merighi S., Varani, et al. Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine ligands, new tools to characterize A(3) adenosine receptors in human tumor cell lines. Current Medicinal Chemistry 2005, 12:1319-1329.
56. Fedorova I.M., Jacobson M.A., Basile A., Jacobson K.A. Behavioral characterization of mice lacking the A(3) adenosine receptor: sensitivity to hypoxic Neurodegeneration. Cellular and Molecular Neurobiology 2003, 23:431-447.
57. Tordera R.M., Totterdell S., Wojcik S.M., Brose N., Elizalde N., Lasheras B., et al. Enhanced anxiety, depressive-like behaviour and impaired recognition memory in mice with reduced expression of the vesicular glutamate transporter 1 (VGLUT1). The European Journal of Neuroscience 2007, 25:281-290.
58. Balschun D., Moechars D., Callaerts-Vegh Z., Vermaercke B., Van Acker N., Andries L., et al. Vesicular glutamate transporter VGLUT1 has a role in hippocampal long-term potentiation and spatial reversal learning. Cerebral Cortex 2010, 20:684-693.
59. Angulo E., Casado V., Mallol J., Canela E.I., Vinals F., Ferrer I., et al. A1 adenosine receptors accumulate in neurodegenerative structures in Alzheimer's disease and mediate both amyloid precursor protein processing and tau phosphorylation and translocation. Brain Pathology 2003, 13:440-451.