Antinociceptive Effects of Novel A2B Adenosine Receptor Antagonists

Journal of Pharmacology and Experimental Therapeutics

Volumn 308, Issue 1, 2004, Pages 358-366

  Abo Salem, Osama M ^a   Hayallah, Alaa M ^a   Bilkei Gorzo, Andras ^a   Filipek, Barbara ^b   Zimmer, Andreas ^a   Müller, Christa E ^a  

^a UNIVERSITY OF BONN   (Germany)

^b JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 PROPYL 8 (4 SULFOPHENYL)XANTHINE; 3,7 DIMETHYL 1 PROPARGYLXANTHINE; 4 (1 BUTYLXANTHIN 8 YL)BENZOIC ACID; 8 (4 BROMOPHENYL) 1 PROPARGYLXANTHINE; 8 (4 SULFOPHENYL)THEOPHYLLINE; 8 (4 SULFOPHENYLCAFFEINE); 8 [4 [2 (4 BENZYLPIPERAZIN 1 YL) 2 OXOETHOXYPHENYL] 1 BUTYLXANTHINE; 8 CYCLOPENTYL 1,3 DIPROPYLXANTHINE; 8 ETHYL 4 METHYL 2 (2,3,5 TRICHLOROPHENYL) 4,5,7,8 TETRAHYDRO 1H IMIDAZO[2,1 I]PURIN 5 ONE; ACETYLSALICYLIC ACID; ADENOSINE A1 RECEPTOR ANTAGONIST; ADENOSINE A2A RECEPTOR ANTAGONIST; ADENOSINE A2B RECEPTOR; ADENOSINE A2B RECEPTOR ANTAGONIST; ADENOSINE RECEPTOR BLOCKING AGENT; CAFFEINE; CODEINE SULFATE; ENPROFYLLINE; IMIDAZOLE DERIVATIVE; MORPHINE; NONSTEROID ANTIINFLAMMATORY AGENT; OPIATE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORIC ACID [3 [8 [2 (3 METHOXYPHENYL)VINYL] 7 METHYL 2,6 DIOXO 1 PROP 2 YNYL 1,2,6,7 TETRAHYDROPURIN 3 YL]PROPYL]ESTER; PSYCHOSTIMULANT AGENT; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; HOT PLATE TEST; HYPERALGESIA; MALE; MOUSE; NONHUMAN; PAIN THRESHOLD; PRIORITY JOURNAL; RECEPTOR BINDING;

ADENOSINE; ANALGESIA; ANIMALS; CAFFEINE; DRUG SYNERGISM; MALE; MICE; MORPHINE; PAIN; RECEPTOR, ADENOSINE A2B;

EID: 0347128094     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.103.056036     Document Type: Article

References (36)

1. Bailey A, Ledent C, Kelly M, Hourani SM, and Kitchen I (2002) Changes in spinal delta and kappa opioid systems in mice deficient in the A2A receptor gene. J Neurosci 22:9210-9220.
2. Bastia E, Varani K, Monopoli A, and Bertorelli R (2002) Effects of A(1) and A(2A) adenosine receptor ligands in mouse acute models of pain. Neurosci Lett 328:241-244.
3. Baumgold J, Nikodijevic O, and Jacobson KA (1992) Penetration of adenosine antagonists into mouse brain as determined by ex vivo binding. Biochem Pharmacol 43:889-894.
4. Brackett LE and Daly JW (1994) Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts. Biochem Pharmacol 47:801-814.
5. Cahill CM, White TD, and Sawynok J (1996) Synergy between mu/ delta-opioid receptors mediates adenosine release from spinal cord synaptosomes. Eur J Pharmacol 298:45-49.
6. Cass IJ and Frederik WS (1962) The augmentation of analgesic effect of aspirin with phenacetin and caffeine. Curr Ther Res 4:583-588.
7. Daly JW (2000) Alkylxanthines as research tools. J Auton Nerv Syst 81:44-52.
8. Daly JW, Butts-Lamb P, and Padgett W (1983) Subclasses of adenosine receptors in the central nervous system: interaction with caffeine and related methylxanthines. Cell Mol Neurobiol 3:69-80.
9. DeLander GE and Hopkins CJ (1986) Spinal adenosine modulates descending antinociceptive pathways stimulated by morphine. J Pharmacol Exp Ther 239:88-93.
10. Dixon AK, Gubitz AK, Sirinathsinghji DJ, Richardson PJ, and Freeman TC (1996) Tissue distribution of adenosine receptor mRNAs in the rat. Br J Pharmacol 118:1461-1468.
11. Doak GJ and Sawynok J (1995) Complex role of peripheral adenosine in the genesis of the response to subcutaneous formalin in the rat. Eur J Pharmacol 281:311-318.
12. Feoktistov I and Biaggioni I (1995) Adenosine A2b receptors evoke interleukin-8 secretion in human mast cells. An enprofylline-sensitive mechanism with implications for asthma. J Clin Investig 96:1979-1986.
13. Feoktistov I and Biaggioni I (1997) Adenosine A2B receptors. Pharmacol Rev 49:381-402.
14. Finlayson K, Butcher SP, Sharkey J, and Olverman HJ (1997) Detection of adenosine receptor antagonists in rat brain using a modified radioreceptor assay. J Neurosci Methods 77:135-142.
15. Fredholm BB, AP IJ, Jacobson KA, Klotz KN and Linden J (2001) International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors. Pharmacol Rev 53:527-552.
16. Hayallah AM, Sandoval-Ramirez J, Reith U, Schobert U, Preiss B, Schumacher B, Daly JW, and Muller CE (2002) 1,8-Disubstituted xanthine derivatives: synthesis of potent A2B-selective adenosine receptor antagonists. J Med Chem 45:1500-1510.
17. Holmgren M, Hedner J, Mellstrand T, Nordberg G, and Hedner T (1986) Characterization of the antinociceptive effects of some adenosine analogues in the rat. Naunyn-Schmiedeberg's Arch Pharmacol 334:290-293.
18. Johansson B, Halldner L, Dunwiddie TV, Masino SA, Poelchen W, Gimenez-Llort L, Escorihuela RM, Fernandez-Teruel A, Wiesenfeld-Hallin Z, Xu XJ, et al. (2001) Hyperalgesia, anxiety and decreased hypoxic neuroprotection in mice lacking the adenosine A1 receptor. Proc Natl Acad Sci USA 98:9407-9412.
19. Karlsten R, Gordh T, and Post C (1992) Local antinociceptive and hyperalgesic effects in the formalin test after peripheral administration of adenosine analogues in mice. Pharmacol Toxicol 70:434-438.
20. Keil GJ, 2nd and DeLander GE (1994) Adenosine kinase and adenosine deaminase inhibition modulate spinal adenosine- and opioid agonist-induced antinociception in mice. Eur J Pharmacol 271:37-46.
21. Kim SA, Marshall MA, Melman N, Kim HS, Muller CE, Linden J, and Jacobson KA (2002) Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7- and 8-positions. J Med Chem 45:2131-2138.
22. Ledent C, Vaugeois JM, Schiffmann SN, Pedrazzini T, El Yacoubi M, Vanderhaeghen JJ, Costentin J, Heath JK, Vassart G, and Parmentier M (1997) Aggressiveness, hypoalgesia and high blood pressure in mice lacking the adenosine A2a receptor. Nature (Lond) 388:674-678.
23. Malec D and Michalska E (1988) The effect of methylxanthines on morphine analgesia in mice and rats. Pol J Pharmacol Pharm 40:223-232.
24. Müller CE (2003) Medicinal chemistry of adenosine A3 receptor ligands. Curr Topics Med Chem 3:445-462.
25. Nakamura I, Ohta Y, and Kemmotsu O (1997) Characterization of adenosine receptors mediating spinal sensory transmission related to nociceptive information in the rat. Anesthesiology 87:577-584.
26. Ongini E and Fredholm BB (1996) Pharmacology of adenosine A2A receptors. Trends Pharmacol Sci 17:364-372.
27. Ozola V, Thorand M, Diekmann M, Qurishi R, Schumacher B, Jacobson KA, and Müller CE (2003) 2-Phenylimidazo[2,1-i]purin-5-ones: structure-activity relationships and characterization of potent and selective inverse agonists at human A3 adenosine receptors. Bioorg Med Chem 11:347-356.
28. Palmer TM and Stiles GL (1995) Adenosine receptors. Neuropharmacology 34:683-694.
29. Phillis JW, Jiang ZG, Chelack BJ, and Wu PH (1980) Morphine enhances adenosine release from the in vivo rat cerebral cortex. Eur J Pharmacol 65:97-100.
30. Reeve AJ and Dickenson AH (1995) The roles of spinal adenosine receptors in the control of acute and more persistent nociceptive responses of dorsal horn neurones in the anaesthetized rat. Br J Pharmacol 116:2221-2228.
31. Rivkees SA, Price SL, and Zhou FC (1995) Immunohistochemical detection of A1 adenosine receptors in rat brain with emphasis on localization in the hippocampal formation, cerebral cortex, cerebellum and basal ganglia. Brain Res 677:193-203.
32. Salvatore CA, Jacobson MA, Taylor HE, Linden J, and Johnson RG (1993) Molecular cloning and characterization of the human A3 adenosine receptor. Proc Natl Acad Sci USA 90:10365-10369.
33. Sawynok J (1998) Adenosine receptor activation and nociception. Eur J Pharmacol 347:1-11.
34. Sawynok J and Yaksh TL (1993) Caffeine as an analgesic adjuvant: a review of pharmacology and mechanisms of action. Pharmacol Rev 45:43-85.
35. Sawynok J, Zarrindast MR, Reid AR, and Doak GJ (1997) Adenosine A3 receptor activation produces nociceptive behaviour and edema by release of histamine and 5-hydroxytryptamine. Eur J Pharmacol 333:1-7.
36. Taiwo YO and Levine JD (1990) Direct cutaneous hyperalgesia induced by adenosine. Neuroscience 38:757-762.