Synthesis and pharmacological evaluation of dual acting antioxidant a 2A adenosine receptor agonists

Journal of Medicinal Chemistry

Volumn 55, Issue 7, 2012, Pages 3521-3534

  Hausler, Nicholas E ^a   Devine, Shane M ^a   McRobb, Fiona M ^a   Warfe, Lyndon ^a   Pouton, Colin W ^a   Haynes, John M ^a   Bottle, Steven E ^b   White, Paul J ^a   Scammells, Peter J ^a  

^a MONASH UNIVERSITY   (Australia)

^b QUEENSLAND UNIVERSITY OF TECHNOLOGY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE 5' N ALKYLCARBOXAMIDE; ADENOSINE A2 RECEPTOR; ADENOSINE RECEPTOR STIMULATING AGENT; CYCLIC AMP; N (2,2 DIPHENYLETHYL)ADENOSINE 5 N ALKYLCARBOXAMIDE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL DAMAGE; CELL DEATH; CELL SURVIVAL; CHO CELL; ISCHEMIA; NONHUMAN;

ADENOSINE; ADENOSINE A2 RECEPTOR AGONISTS; AMIDES; ANIMALS; ANTIOXIDANTS; CELL HYPOXIA; CELL LINE; CELL SURVIVAL; CHO CELLS; CRICETINAE; CRICETULUS; CYCLIC AMP; HUMANS; MODELS, MOLECULAR; MYOBLASTS; MYOCYTES, CARDIAC; RATS; REACTIVE OXYGEN SPECIES; RECEPTOR, ADENOSINE A2A; REPERFUSION INJURY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84859786851     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300206u     Document Type: Article

References (41)

1. 3 adenosine receptor agonists: a novel, targeted therapy Immun., Endocr. Metab. Agents in Med. Chem. 2007, 7, 298-303
2. 3 adenosine receptor-mediated protection of the ischemic heart Vasc. Pharmacol. 2005, 42, 271-279
3. 2A agonists in development for the treatment of inflammation Expert Opin. Invest. Drugs 2005, 14, 797-806
4. 2A receptor agonist (CGS-21680) prevents endotoxin-induced effects on nucleotidase activities in mouse lymphocytes Eur. J. Pharmacol. 2011, 651, 212-217
5. Junqueira, A. F. T.; de, A.; Dias, A. A. M.; Vale, M. L.; Spilborghs, G. M. G. T.; Bossa, A. S.; Lima, B. B.; Carvalho, A. F.; Guerrant, R. L.; Ribeiro, R. A.; Brito, G. A. Adenosine deaminase inhibition prevents Clostridium difficile toxin A-induced enteritis in mice Infect. Immun. 2011, 79, 653-662
6. Wu, B; Chien, E. Y. T.; Mol, C. D.; Fenalti, G.; Liu, W.; Katritch, V.; Abagyan, R.; Brooun, A.; Wells, P.; Bi, F. C.; Hamel, D. J.; Kuhn, P.; Handel, T. M.; Cherezov, V.; Stevens, R. C. Structures of the CXCR4 Chemokine GPCR with Small-Molecule and Cyclic Peptide Antagonists Science 2010, 330, 1066-1071
7. Chien, E. Y. T.; Liu, W.; Zhao, Q.; Katritch, V.; Han, G. W.; Hanson, M. A.; Shi, L.; Newman, A. H.; Javitch, J. A.; Cherezov, V.; Stevens, R. C. Structure of the Human Dopamine D3 Receptor in Complex with a D2/D3 Selective Antagonist Science 2010, 330, 1091-1095
8. Warne, T.; Serrano-Vega, M. J.; Baker, J. G.; Moukhametzianov, R.; Edwards, P. C.; Henderson, R.; Leslie, A. G. W.; Tate, C. G.; Schertler, G. F. X. Structure of a β1-adrenergic G-protein-coupled receptor Nature 2008, 454, 486-491
9. 2-adrenergic G protein-coupled receptor Science 2007, 318, 1258-1265
10. 2A adenosine receptor bound to an antagonist Science 2008, 322, 1211-1217
11. 2A adenosine receptor Science 2011, 332, 322-327
12. 2 receptor agonist, involve the opening of glibenclamide-sensitive potassium channels Eur. J. Pharmacol. 1992, 213, 199-204
13. 6-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl) ethyl]adenosine, and its 5′- N -ethylribofuranuronamide derivative Nucleosides Nucleotides 1989, 8, 357-366
14. 2 receptor ligands J. Med. Chem. 1990, 33, 1919-1924
15. 2A receptors mediate GABAergic inhibition of respiration in immature rats J. Appl. Physiol. 2006, 100, 91-97
16. 2A receptor facilitates brain-derived neurotrophic factor modulation of synaptic transmission in hippocampal slices J. Neurosci. 2004, 24, 2905-2913
17. 2A agonists and comparison of inhaled pharmacokinetics in a preclinical model with clinical pharmacokinetic data Bioorg. Med. Chem. Lett. 2009, 19, 4471-4475
18. Müller, C. E.; Jacobson, K. A. Recent developments in adenosine receptor ligands and their potential as novel drugs Biochim. Biophys. Acta 2011, 1808, 1290-1308
19. Garnock-Jones, K. P.; Curran, M. P. Regadenoson Am. J. Cardiovasc. Drugs 2010, 10, 65-71
20. Laubach, V. E.; French, B. A.; Okusa, M. D. Targeting of adenosine receptors in ischemia-reperfusion injury Expert Opin. Ther. Targets 2011, 15, 103-118
21. 2 receptor activation attenuates reperfusion injury by inhibiting neutrophil accumulation, superoxide generation and coronary endothelial adherence J. Pharmacol. Exp. Ther. 1997, 280, 301-309
22. Marczin, N.; El-Habashi, N.; Hoare, G. S.; Bundy, R. E.; Yacoub, M. Antioxidants in myocardial ischemia-reperfusion injury: therapeutic potential and basic mechanisms Arch. Biochem. Biophys. 2003, 420, 222-236
23. Zweier, J. L.; Talukder, M. A. H. The role of oxidants and free radicals in reperfusion injury Cardiovasc. Res. 2006, 70, 181-190
24. 1-Adenosine Receptor Agonists Bioorg. Med. Chem. Lett. 2007, 17, 5437-5441
25. 3 Adenosine Receptor Agonists Bioorg. Med. Chem. 2010, 18, 3078-3087
26. Burton, G. W.; Ingold, K. U. Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro J. Am. Chem. Soc. 1981, 103, 6472-6477
27. Packer, L.; Witt, E. H.; Tritschler, H. J. Alpha-lipoic acid as a biological antioxidant Free Radical Biol. Med. 1995, 19, 227-250
28. Ghibu, S.; Richard, C.; Vergely, C.; Zeller, M.; Cottin, Y.; Rochette, L. Antioxidant properties of an endogenous thiol: alpha-lipoic acid, useful in the prevention of cardiovascular diseases J. Cardiovasc. Pharmacol. 2009, 54, 391-398
29. Foitzik, R. C.; Devine, S. M.; Hausler, N. E.; Scammells, P. J. Linear and convergent approaches to 2-substituted adenosine-5′- N -alkylcarboxamides Tetrahedron 2009, 65, 8851-8857
30. 6-(benzotriazol-1-yl) Purine Nucleosides Eur. J. Org. Chem. 2011, 1092-1098
31. 2A receptor structures reveal common features of GPCR activation Nature 2011, 474, 521-525
32. 2A Receptor J. Med. Chem. 2011, 54, 4312-4323
33. 2B receptors by endogenous adenosine J. Cardiovasc. Pharmacol. 2009, 53, 424-433
34. 1 receptor agonist VCP28 reduces ischemia injury in a cardiac cell line and ischaemia-reperfusion injury in isolated rat hearts at concentrations that do not affect heart rate J. Cardiovasc. Pharmacol. 2010, 56, 282-292
35. Walker, J. R.; Fairfull-Smith, K. E.; Anzai, K.; Lau, S.; White, P. J.; Scammells, P. J.; Bottle, S. E. Edaravone containing isoindoline nitroxides for potential treatment of ischemia Med. Chem. Comm. 2011, 2, 436-441
36. Kolamunne, R. T.; Clare, M.; Griffiths, H. R. Mitochondrial superoxide anion radicals mediate induction of apoptosis in cardiac myoblasts exposed to chronic hypoxia Arch. Biochem. Biophys. 2011, 505, 256-265
37. Ballesteros, J. A.; Weinstein, H.; Stuart, C. S. Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors Methods Neurosci. 1995, 25, 366-428
38. LigPrep, version 2.4; Schrödinger, LLC: New York, 2010.
39. Maestro, version 9.1; Schrödinger, LLC: New York, 2010.
40. Verdonk, M. L.; Cole, J. C.; Hartshorn, M. J.; Murray, C. W.; Taylor, R. D. Improved protein-ligand docking using GOLD Proteins 2003, 52, 609-623
41. Verdonk, M. L.; Chessari, G.; Cole, J. C.; Hartshorn, M. J.; Murray, C. W.; Nissink, J. W. M.; Taylor, R. D.; Taylor, R. Modeling water molecules in protein-ligand docking using GOLD J. Med. Chem. 2005, 48, 6504-6515