Orally active adenosine A 1 receptor agonists with antinociceptive effects in mice

Journal of Medicinal Chemistry

Volumn 55, Issue 14, 2012, Pages 6467-6477

  Korboukh, Ilia ^a   Hull Ryde, Emily A ^a   Rittiner, Joseph E ^b   Randhawa, Amarjit S ^a   Coleman, Jennifer ^b   Fitzpatrick, Brendan J ^b   Setola, Vincent ^b   Janzen, William P ^a   Frye, Stephen V ^a   Zylka, Mark J ^b   Jin, Jian ^a  

^a University of North Carolina   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (ACETOXYMETHYL) 5 [2 CHLORO 6 [(2 HYDROXYCYCLOPENTYL)AMINO] 9H PURIN 9 YL]TETRAHYDROFURAN 3,4 DIYL DIACETATE; 2 (ACETOXYMETHYL) 5 [2 CHLORO 6 [[2 [(DI TERT BUTOXYPHOSPHORYL)OXY]CYCLOPENTYL]AMINO] 9H PURIN 9 YL]TETRAHYDROFURAN 3,4 DIYL DIACETATE; 2 [2 CHLORO 6 [(1 HYDROXY 3 PHENYLPROPAN 2 YL)AMINO] 9H PURIN 9 YL] 5 (HYDROXYMETHYL)TETRAHYDROFURAN 3,4 DIOL; 2 [[2 CHLORO 9 [3,4 DIHYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 9H PURIN 6 YL]AMINO] 3 PHENYLPROPYL DIMETHYL PHOSPHATE; 2 [[2 CHLORO 9 [3,4 DIHYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 9H PURIN 6 YL]AMINO]CYCLOPENTYL DIMETHYL PHOSPHATE; [5 [2 CHLORO 6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYL DIETHYL PHOSPHATE; [5 [2 CHLORO 6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYL DIMETHYL PHOSPHATE; [5 [2 CHLORO 6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYL DIPHENETHYL PHOSPHATE; [5 [6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYL DIMETHYL PHOSPHATE; ADENOSINE A1 RECEPTOR AGONIST; ADENOSINE A2A RECEPTOR AGONIST; ADENOSINE A2B RECEPTOR AGONIST; ADENOSINE A3 RECEPTOR AGONIST; ADENOSINE PHOSPHATE; DI TERT BUTYL [2 [[2 CHLORO 9 [3,4 DIHYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 9H PURIN 6 YL]AMINO] 3 PHENYLPROPYL] PHOSPHATE; ETHYL 2 [[[[5 [2 CHLORO 6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHOXY][(2 OXO 2 ETHYLOXYETHYL)AMINO]PHOSPHORYL]AMINO]ACETATE; SODIUM 2 [[2 CHLORO 9 [3,4 DIHYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 9H PURIN 6 YL]AMINO] 3 PHENYLPROPYL PHOSPHATE; SODIUM 2 [[2 CHLORO 9 [3,4 DIHYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 9H PURIN 6 YL]AMINO]CYCLOPENTYL PHOSPHATE; SODIUM [5 [2 CHLORO 6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYL PHOSPHATE; SODIUM [5 [6 (CYCLOPENTYLAMINO) 9H PURIN 9 YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYL PHOSPHATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN;

ADENOSINE A1 RECEPTOR AGONISTS; ADENOSINE MONOPHOSPHATE; ADMINISTRATION, ORAL; ANALGESICS; ANIMALS; BEHAVIOR, ANIMAL; HEK293 CELLS; HUMANS; MALE; MICE; NOCICEPTION; RECEPTOR, ADENOSINE A1; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 84864243926     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3004834     Document Type: Article

References (50)

1. Fredholm, B. B.; Arslan, G.; Halldner, L.; Kull, B.; Schulte, G.; Wasserman, W. Structure and function of adenosine receptors and their genes Naunyn-Schmiedeberg's Arch. Pharmacol. 2000, 362, 364-374
2. Swanson, T. H.; Drazba, J. A.; Rivkees, S. A. Adenosine A1 receptors are located predominantly on axons in the rat hippocampal formation J. Comp. Neurol. 1995, 363, 517-531
3. Saura, C. A.; Mallol, J.; Canela, E. I.; Lluis, C.; Franco, R. Adenosine deaminase and A1 adenosine receptors internalize together following agonist-induced receptor desensitization J. Biol. Chem. 1998, 273, 17610-17617
4. Middlekauff, H. R.; Rivkees, S. A.; Raybould, H. E.; Bitticaca, M.; Goldhaber, J. I.; Weiss, J. N. Localization and functional effects of adenosine A1 receptors on cardiac vagal afferents in adult rats Am. J. Physiol. 1998, 274, H441-447
5. Schulte, G.; Robertson, B.; Fredholm, B. B.; DeLander, G. E.; Shortland, P.; Molander, C. Distribution of antinociceptive adenosine A1 receptors in the spinal cord dorsal horn, and relationship to primary afferents and neuronal subpopulations Neuroscience 2003, 121, 907-916
6. Proctor, W. R.; Dunwiddie, T. V. Pre- and postsynaptic actions of adenosine in the in vitro rat hippocampus Brain Res. 1987, 426, 187-190
7. Johansson, S. M.; Lindgren, E.; Yang, J. N.; Herling, A. W.; Fredholm, B. B. Adenosine A1 receptors regulate lipolysis and lipogenesis in mouse adipose tissue-interactions with insulin Eur. J. Pharmacol. 2008, 597, 92-101
8. Boison, D. Adenosine as a neuromodulator in neurological diseases Curr. Opin. Pharmacol. 2008, 8, 2-7
9. Mantell, S.; Jones, R.; Trevethick, M. Design and application of locally delivered agonists of the adenosine A(2A) receptor Expert. Rev. Clin. Pharmacol. 2010, 3, 55-72
10. Castillo, C. A.; Albasanz, J. L.; Leon, D.; Jordan, J.; Pallas, M.; Camins, A.; Martin, M. Age-related expression of adenosine receptors in brain from the senescence-accelerated mouse Exp. Gerontol. 2009, 44, 453-461
11. Jacobson, K. A.; van Galen, P. J.; Williams, M. Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential J. Med. Chem. 1992, 35, 407-422
12. Poulsen, S. A.; Quinn, R. J. Adenosine receptors: new opportunities for future drugs Bioorg. Med. Chem. 1998, 6, 619-641
13. Gao, Z. G.; Jacobson, K. A. Emerging adenosine receptor agonists Expert Opin. Emerg. Drugs 2007, 12, 479-492
14. Hayashida, M.; Fukuda, K.; Fukunaga, A. Clinical application of adenosine and ATP for pain control J. Anesth. 2005, 19, 225-235
15. Zylka, M. J. Pain-relieving prospects for adenosine receptors and ectonucleotidases Trends. Mol. Med. 2011, 17, 188-196
16. Sawynok, J.; Liu, X. J. Adenosine in the spinal cord and periphery: release and regulation of pain Prog. Neurobiol. 2003, 69, 313-340
17. Eisenach, J. C.; Rauck, R. L.; Curry, R. Intrathecal, but not intravenous adenosine reduces allodynia in patients with neuropathic pain Pain 2003, 105, 65-70
18. Eisenach, J. C.; Curry, R.; Hood, D. D. Dose response of intrathecal adenosine in experimental pain and allodynia Anesthesiology 2002, 97, 938-942
19. Belfrage, M.; Segerdahl, M.; Arner, S.; Sollevi, A. The safety and efficacy of intrathecal adenosine in patients with chronic neuropathic pain Anesth. Analg. 1999, 89, 136-142
20. Sowa, N. A.; Voss, M. K.; Zylka, M. J. Recombinant ecto-5′- nucleotidase (CD73) has long lasting antinociceptive effects that are dependent on adenosine A1 receptor activation Mol. Pain. 2010, 6, 20
21. Sowa, N. A.; Vadakkan, K. I.; Zylka, M. J. Recombinant mouse PAP has pH-dependent ectonucleotidase activity and acts through A(1)-adenosine receptors to mediate antinociception PLoS One 2009, 4, e4248
22. Zylka, M. J.; Sowa, N. A.; Taylor-Blake, B.; Twomey, M. A.; Herrala, A.; Voikar, V.; Vihko, P. Prostatic acid phosphatase is an ectonucleotidase and suppresses pain by generating adenosine Neuron 2008, 60, 111-122
23. Goldman, N.; Chen, M.; Fujita, T.; Xu, Q.; Peng, W.; Liu, W.; Jensen, T. K.; Pei, Y.; Wang, F.; Han, X.; Chen, J. F.; Schnermann, J.; Takano, T.; Bekar, L.; Tieu, K.; Nedergaard, M. Adenosine A1 receptors mediate local anti-nociceptive effects of acupuncture Nat. Neurosci. 2010, 13, 883-888
24. Rittiner, J. E.; Korboukh, I.; Hull-Ryde, E. A.; Jin, J.; Janzen, W. P.; Frye, S. V.; Zylka, M. J. AMP Is an Adenosine A1 Receptor Agonist J. Biol. Chem. 2012, 287, 5301-5309
25. Curros-Criado, M. M.; Herrero, J. F. The antinociceptive effects of the systemic adenosine A1 receptor agonist CPA in the absence and in the presence of spinal cord sensitization Pharmacol., Biochem. Behav. 2005, 82, 721-726
26. Klotz, K. N. Adenosine receptors and their ligands Naunyn-Schmiedeberg's Arch. Pharmacol. 2000, 362, 382-391
27. Franchetti, P.; Cappellacci, L.; Vita, P.; Petrelli, R.; Lavecchia, A.; Kachler, S.; Klotz, K. N.; Marabese, I.; Luongo, L.; Maione, S.; Grifantini, M. N6-Cycloalkyl- and N6-bicycloalkyl-C5′(C2′)-modified adenosine derivatives as high-affinity and selective agonists at the human A1 adenosine receptor with antinociceptive effects in mice J. Med. Chem. 2009, 52, 2393-2406
28. Mathew, S. C.; Ghosh, N.; By, Y.; Berthault, A.; Virolleaud, M. A.; Carrega, L.; Chouraqui, G.; Commeiras, L.; Condo, J.; Attolini, M.; Gaudel-Siri, A.; Ruf, J.; Parrain, J. L.; Rodriguez, J.; Guieu, R. Design, synthesis and biological evaluation of a bivalent micro opiate and adenosine A1 receptor antagonist Bioorg. Med. Chem. Lett. 2009, 19, 6736-6739
29. Klotz, K. N.; Hessling, J.; Hegler, J.; Owman, C.; Kull, B.; Fredholm, B. B.; Lohse, M. J. Comparative pharmacology of human adenosine receptor subtypes-characterization of stably transfected receptors in CHO cells Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 357, 1-9
30. Schenone, S.; Brullo, C.; Musumeci, F.; Bruno, O.; Botta, M. A1 receptors ligands: past, present and future trends Curr. Top. Med. Chem. 2010, 10, 878-901
31. Fredholm, B. B.; AP, I. J.; Jacobson, K. A.; Klotz, K. N.; Linden, J. International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors Pharmacol. Rev. 2001, 53, 527-552
32. Elzein, E.; Zablocki, J. A1 adenosine receptor agonists and their potential therapeutic applications Expert. Opin. Investig. Drugs 2008, 17, 1901-1910
33. Naito, Y.; Lowenstein, J. M. 5′-Nucleotidase from rat heart membranes. Inhibition by adenine nucleotides and related compounds Biochem. J. 1985, 226, 645-651
34. Xu, F.; Wu, H.; Katritch, V.; Han, G. W.; Jacobson, K. A.; Gao, Z. G.; Cherezov, V.; Stevens, R. C. Structure of an agonist-bound human A2A adenosine receptor Science 2011, 332, 322-327
35. Lebon, G.; Warne, T.; Edwards, P. C.; Bennett, K.; Langmead, C. J.; Leslie, A. G.; Tate, C. G. Agonist-bound adenosine A2A receptor structures reveal common features of GPCR activation Nature 2011, 474, 521-525
36. Daly, J. W.; Padgett, W.; Thompson, R. D.; Kusachi, S.; Bugni, W. J.; Olsson, R. A. Structure-activity relationships for N6-substituted adenosines at a brain A1-adenosine receptor with a comparison to an A2-adenosine receptor regulating coronary blood flow Biochem. Pharmacol. 1986, 35, 2467-2481
37. Qu, X.; Cooney, G.; Donnelly, R. Short-term metabolic and haemodynamic effects of GR79236 in normal and fructose-fed rats Eur. J. Pharmacol. 1997, 338, 269-276
38. Muller, C. E. Adenosine receptor ligands-recent developments part I. Agonists Curr. Med. Chem. 2000, 7, 1269-1288
39. Linden, J.; Thai, T.; Figler, H.; Jin, X.; Robeva, A. S. Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells Mol. Pharmacol. 1999, 56, 705-713
40. Bozarov, A.; Wang, Y. Z.; Yu, J. G.; Wunderlich, J.; Hassanain, H. H.; Alhaj, M.; Cooke, H. J.; Grants, I.; Ren, T.; Christofi, F. L. Activation of adenosine low-affinity A3 receptors inhibits the enteric short interplexus neural circuit triggered by histamine Am. J. Physiol. Gastrointest. Liver Physiol. 2009, 297, G1147-1162
41. Hecker, S. J.; Erion, M. D. Prodrugs of phosphates and phosphonates J. Med. Chem. 2008, 51, 2328-2345
42. Cappellacci, L.; Franchetti, P.; Vita, P.; Petrelli, R.; Lavecchia, A.; Costa, B.; Spinetti, F.; Martini, C.; Klotz, K. N.; Grifantini, M. 5′-Carbamoyl derivatives of 2′-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 receptor from different species Bioorg. Med. Chem. 2008, 16, 336-353
43. Vittori, S.; Lorenzen, A.; Stannek, C.; Costanzi, S.; Volpini, R.; AP, I. J.; Kunzel, J. K.; Cristalli, G. N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor J. Med. Chem. 2000, 43, 250-260
44. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities J. Org. Chem. 1997, 62, 7512-7515
45. Inbe, H.; Watanabe, S.; Miyawaki, M.; Tanabe, E.; Encinas, J. A. Identification and characterization of a cell-surface receptor, P2Y15, for AMP and adenosine J. Biol. Chem. 2004, 279, 19790-19799
46. Cooper, J.; Hill, S. J.; Alexander, S. P. An endogenous A2B adenosine receptor coupled to cyclic AMP generation in human embryonic kidney (HEK 293) cells Br. J. Pharmacol. 1997, 122, 546-550
47. Hua, X.; Erikson, C. J.; Chason, K. D.; Rosebrock, C. N.; Deshpande, D. A.; Penn, R. B.; Tilley, S. L. Involvement of A1 adenosine receptors and neural pathways in adenosine-induced bronchoconstriction in mice Am. J. Physiol. Lung Cell Mol. Physiol. 2007, 293, L25-32
48. Johansson, B.; Halldner, L.; Dunwiddie, T. V.; Masino, S. A.; Poelchen, W.; Gimenez-Llort, L.; Escorihuela, R. M.; Fernandez-Teruel, A.; Wiesenfeld-Hallin, Z.; Xu, X. J.; Hardemark, A.; Betsholtz, C.; Herlenius, E.; Fredholm, B. B. Hyperalgesia, anxiety, and decreased hypoxic neuroprotection in mice lacking the adenosine A1 receptor Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 9407-9412
49. Hargreaves, K.; Dubner, R.; Brown, F.; Flores, C.; Joris, J. A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia Pain 1988, 32, 77-88
50. Fairbanks, C. A. Spinal delivery of analgesics in experimental models of pain and analgesia Adv. Drug Delivery Rev. 2003, 55, 1007-1041