Novel ergopeptides as dual ligands for adenosine and dopamine receptors

Journal of Medicinal Chemistry

Volumn 50, Issue 13, 2007, Pages 3062-3069

  Vendrell, Marc ^a   Angulo, Ester ^a   Casadó, Vicent ^a   Lluis, Carme ^a   Franco, Rafael ^a   Albericio, Fernando ^a   Royo, Miriam ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; CYCLIC AMP; DOPAMINE RECEPTOR; DOPAMINE RECEPTOR STIMULATING AGENT; PEPTIDE LIBRARY;

ARTICLE; CENTRAL NERVOUS SYSTEM; COMBINATORIAL CHEMISTRY; CONTROLLED STUDY; HUMAN; HUMAN CELL; LIGAND BINDING; PARKINSON DISEASE;

ANIMALS; BINDING, COMPETITIVE; CELL LINE, TUMOR; CELLS, CULTURED; CYCLIC AMP; DOPAMINE AGONISTS; DOPAMINE ANTAGONISTS; ERGOLINES; HUMANS; LIGANDS; MICE; OLIGOPEPTIDES; RADIOLIGAND ASSAY; RECEPTORS, DOPAMINE; RECEPTORS, PURINERGIC P1; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34347267665     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060947x     Document Type: Article

References (49)

1. 2 dopamine agonists increases antiparkinsonian activity but not dyskinesia in MPTP-treated monkeys. Exp. Neurol. 2000, 162, 321-327.
2. 2A receptor antagonist, for the treatment of Parkinson's disease. Expert Opin. Invest. Drugs 2005, 14, 729-738.
3. 2A receptor selective antagonist KW6002: Research and development toward a novel nondopaminergic therapy for Parkinson's disease. Neurology 2003, 61 (Suppl 6), S97-S100.
4. Roth, B. L.; Sheffler, D. J.; Kroeze, W. K. Magic shotguns versus magic bullets: Selectively non-selective drugs for mood disorders and schizophrenia. Nat. Rev. Drug Discovery 2004, 3, 353-359.
5. Cmeserly, P.; Ágoston, V.; Pongor, S. The efficiency of multi-target drugs: The network approach might help drug design. Trends Pharmacol. Sci. 2005, 26, 178-182.
6. Barbey, S.; Goosens, L.; Taverne, T.; Cornet, J.; Choesmel, V.; Rouaud, C.; Gimeno, G.; Yannic-Arnoult, S.; Michaux, C.; Charlier, C.; Houssin, R.; Henichard, J. P. Synthesis and activity of a new methoxytetrahydropyran derivative as dual cyclooxygenase-2/5-lipoxygenase inhibitor. Bioorg. Med. Chem. Lett. 2002, 12, 779-782.
7. Morphy, R.; Kay, C.; Rankovic, Z. From magic bullets to designed multiple ligands. Drug Discovery Today 2004, 9, 641-651.
8. Carlsson, A. The current status of the dopamine hyphotesis of schizophrenia. Neuropsychopharmacology 1988, 1, 179-186.
9. Campiani, G.; Butini, S.; Fattorusso, C.; Catalanotti, B.; Gemma, S.; Nacci, V.; Fiorini, I.; Morelli, E.; Cagnotto, A.; Mereghetti, I.; Mennini, T.; Carli, M.; Minetti, P.; Di Cesare, M. A.; Mastroianni, D.; Scafetta, N.; Galletti, B.; Stasi, M. A.; Castorina, M.; Pacifici, L.; Vertechy, M.; Di Serio, S.; Ghirardi, O.; Tinti, O.; Carminati, P. Pyrrolo[1,3]benzothiazepine-based serotonin and dopamine receptor antagonists. Molecular modeling, further structure-activity relationship studies, and identification of novel atypical antipsychotic agents. J. Med. Chem. 2004, 47, 143-157.
10. Campiani, G.; Butini, S.; Fattorusso, C.; Trotta, F.; Gemma, S.; Catalanotti, B.; Nacci, V.; Fiorini, I.; Cagnotto, A.; Mereghetti, I.; Mennini, T.; Minetti, P.; Di Cesare, M. A.; Stasi, M. A.; Di Serio, S.; Ghirardi, O.; Tinti, O.; Carminati, P. Novel atypical antyphsicotic agents: Rational design, an efficient palladium-catalyzed route, and pharmacological studies. J. Med. Chem. 2005, 48, 1705-1708.
11. Jones, H. M.; Pilowsky, L. S. New targets for antiphysotics. Expert Rev. Neurother. 2002, 2, 61-68.
12. Morphy, R.; Rankovic, Z. Designed multiple ligands. An emerging drug discovery paradigm. J. Med. Chem. 2005, 48, 1-21 and references therein.
13. Buccafusco, J. J.; Terry, A. V., Jr. Multiple CNS targets for eliciting beneficial effects on memory and cognition. J. Pharmacol. Exp. Ther. 2000, 295, 438-446.
14. Youdim, M. B. H.; Buccafusco, J. J. Multi-functional drugs for various CNS targets in the treatment of neurodegenerative disorders. Trends Pharmacol. Sci. 2005, 26, 27-35.
15. Mercuri, N. B.; Bernardi, G. The 'magic' of L-dopa: Why is it the gold standard Parkinson's disease therapy? Trends Pharmacol. Sci. 2005, 26, 341-344.
16. (a) Kurlan, R. Practical therapy of Parkinson's disease. Semin. Neurol. 1987, 7, 160-166.
17. (b) Mouradian, M. M.; Heuser, I. J. E.; Baronti, F.; Fabbrini, G.; Juncos, J. L.; Chase, T. N. Pathogenesis of dyskinesias in Parkinson's disease. Ann. Neurol. 1989, 25, 523-526.
18. Ferré, S.; Fredholm, B. B.; Morelli, M.; Popoli, P.; Fuxe, K. Adenosine-dopamine receptor-receptor interactions as an integrative mechanism in the basal ganglia. Trends Neurosci. 1997, 10, 482-487.
19. Agnati, L. F.; Ferré, S.; Lluis, C.; Franco, R.; Fuxe, K. Mechanisms and therapeutical implications of intramembrane receptor/receptor interactions among heptahelical receptors with examples from the striatopallidal GABA neurons. Pharmacol. Rev. 2003, 55, 509-550.
20. Franco, R.; Casadó, V.; Mallol, J.; Ferré S.; Fuxe, K.; Cortés, A.; Ciruela, F.; Lluis, C.; Canela, E. I. Dimer-based model for heptaspanning membrane receptors. Trends Biochem. Sci. 2005, 300, 360-366.
21. 1 receptors form functionally interacting heteromeric complexes. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 8606-8611.
22. 1 receptors in stably cotransfected fibroblast cells and neurons. Neuroscience 2002, 113, 709-719.
23. 2A receptor. J. Mol. Neurosci. 2004, 25, 191-200.
24. 2 receptors. J. Biol. Chem. 2002, 277, 18091-18097.
25. 2 receptor-receptor heteromerization. J. Biol. Chem. 2003, 278, 46741-46749.
26. 2 receptors in living cells. Biochem. Biophys. Res. Commun. 2003, 306, 544-549.
27. 2 receptors. Anal. Chem. 2004, 76, 5354-5363.
28. 2 receptors in rat striatal membranes. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 7238-7241.
29. 2 receptors induces rotational behaviour in response to dopaminergic stimulation in intact rats. Eur. J. Pharmacology 1994, 257, 21-25.
30. 2A receptor antagonist. J. Neuroscience 2000, 20, 5848-5852.
31. 2A adenosine receptor antagonists with 8-styrylxanthine structure: Potential drugs for Parkinson's disease. J. Org. Chem. 2004, 69, 3308-3318.
32. Evans, B. E.; Rittle, K. E.; Bock, M. G.; Dipardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. Methods for drug discovery - Development of potent, selective, orally effective cholecystokinin antagonists. J. Med. Chem. 1988, 31, 2235-2246.
33. Guo, T.; Hobbs, D. W. Privileged structure-based combinatorial libraries targeting G protein-coupled receptors. Assay Drug Dev. Technol. 2003, 1, 579-592.
34. Messer, W. S. Bivalent ligands for G-protein coupled receptors. Curr. Pharm. Des. 2004, 10, 2015-2020.
35. Berde, B.; Stürmer, E. Introduction to the pharmacology of ergot alkaloids and related compounds as a basis of their therapeutic application. In Ergot Alkaloids and Related Compounds; Berde, B.; Schild, H. O. Eds.; Springer-Verlag: Berlin, 1978; pp 1-28.
36. Stadler, P. A.; Stürmer, E. Comparative studies on the pharmacological properties of stereoisomerers of ergotamine and dihydroergotamine. Naunyn-Schmiedeberg's Arch. Pharmacol. 1970, 266, 457.
37. Walzel, B.; Riederer, B.; Keller, U. Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea. Chem. Biol. 1997, 4, 223-230.
38. Jacobson, K. A.; Gao, Z.-G. Adenosine receptors as therapeutic targets. Nat. Rev. Drug Disovery 2006, 5, 247-264.
39. Fredholm, B. B.; IJzerman, A. P.; 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.
40. 2A receptor heteromers. J. Neurosci. 2006, 26, 2080-2087.
41. 2BR, see: Casadó, V.; Casillas, T.; Mallol, J.; Canela, E. I.; Lluis, C.; Franco, R. The adenosine receptors present on the plasma membrane of chromaffin cells are of the A2b subtype. J. Neurochem. 1992, 59, 425-431.
42. Missale, C.; Nash, S. R.; Robinson, S. W.; Jaber, M.; Caron, M. G. Dopamine receptors: From structure to function. Physiol. Rev. 1998, 78, 189-225.
43. Neve, K. A.; Seamans, J. K.; Trantham-Davidson, H. Dopamine receptor signalling. J. Recept. Signal Transduction 2004, 24, 165-205.
44. 2 receptor-induced responses in stably transfected human neuroblastoma cells. J. Neurochem. 2000, 74, 432-43.
45. 1 adenosine receptor from pig brain: Characterization and evidence of the role of the cell membrane on the coexistence of high and low affinity states. J. Neurosci. Res. 1990, 26, 467-473.
46. 1 adenosine receptors to form functional modules in the cell membrane. Mol. Cell. Biol. 2000, 20, 5164-5174.
47. Cheng, Y.-C.; Prusoff, W. H. Relation between the inhibition constant (K1) and the concentration of inhibitor which causes fifty per cent inhibition (I50) of an enzymic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
48. Casadó, V.; Casillas, T.; Mallol, J.; Canela, E. I.; Lluis, C.; Franco, R. The adenosine receptors present on the plasma membrane of chromaffin cells are of the A2b subtype. J. Neurochem. 2000, 59, 425-431.
49. 1 receptors in stably cotransfected fibroblast cells. J. Biol. Chem. 1998, 273, 4718-4724.