Structure-activity relationships of bisphosphate nucleotide derivatives as P2Y1 receptor antagonists and partial agonists

Journal of Medicinal Chemistry

Volumn 42, Issue 9, 1999, Pages 1625-1638

  Nandanan, Erathodiyil ^a   Camaioni, Emidio ^a   Jang, Soo Yeon ^a   Kim, Yong Chul ^a   Cristalli, Gloria ^d   Herdewijn, Piet ^e   Secrist III, John A ^c   Tiwari, Kamal N ^c   Mohanram, Arvind ^b   Harden, T Kendall ^b   Boyer, José L ^b   Jacobson, Kenneth A ^a,f  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

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

^c SOUTHERN RESEARCH INSTITUTE   (United States)

^d UNIVERSITY OF CAMERINO   (Italy)

^e REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^f NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1', 5' ANHYDRO 2' (ADENIN 9 YL) 2',3' DIDEOXY DEXTRO ARABINOHEXITOL 4',6' BIS(DIAMMONIUM PHOSPHATE); 2 CHLORO 2' DEOXY N6 METHYLADENOSINE 3',5' BIS(DIAMMONIUM PHOSPHATE); 2 METHYLTHIOADENOSINE 5' DIPHOSPHATE; 2' DEOXY 2 (METHYLTHIO) N6 METHYLADENOSINE 3',5' BIS(DIAMMONIUM PHOSPHATE); 2' DEOXY 2 (PROPYLTHIO) N6 METHYLADENOSINE 3',5' BIS(DIAMMONIUM PHOSPHATE); DEOXYADENOSINE DERIVATIVE; NUCLEOTIDE DERIVATIVE; PHOSPHOLIPASE C; PURINE P2Y RECEPTOR; PURINERGIC RECEPTOR BLOCKING AGENT; PURINERGIC RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CYTOSKELETON; DRUG RECEPTOR BINDING; ENZYME INHIBITION; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; THROMBOCYTE ACTIVATION; THROMBOCYTE AGGREGATION;

ANIMALS; CELL LINE; DEOXYADENOSINES; ENZYME ACTIVATION; ERYTHROCYTE MEMBRANE; HUMANS; PHOSPHOLIPASE C; PHOSPHORIC ACID ESTERS; RECEPTORS, PURINERGIC P2; STRUCTURE-ACTIVITY RELATIONSHIP; TURKEYS;

EID: 0033529073     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980657j     Document Type: Article

References (39)

1. Fredholm, B. B.; Abbracchio, M. P.; Burnstock, G.; Dubyak, G. R.; Harden, T. K.; Jacobson, K. A.; Schwabe, U.; Williams, M. Toward a revised nomenclature for P1 and P2 receptors. Trends Pharm. Sci. 1997, 18, 79-82.
2. North, R. A.; Barnard, E. A. Nucleotide receptors. Curr. Opin. NeuroBiol. 1997, 7, 346-357.
3. Webb, T. E.; Simon, J.; Krishek, B. J.; Bateson, A. N.; Smart, T. G.; King, B. F.; Burnstock, G.; Barnard, E. A. Cloning and functional expression of a brain G-protein-coupled ATP receptor. FEBS Lett. 1993, 324, 219-225.
4. Schachter, J. B.; Li, Q.; Boyer, J. L.; Nicholas, R. A.; Harden, T. K. 2nd messenger cascade specificity and pharmacological selectivity of the human P2Y1-purinoceptor. Br. J. Pharmacol. 1996, 118, 167-173.
5. Janssens, R.; Communi, D.; Pirotton, S.; Samson, M.; Parmentier, M.; Boeynaems, J.-M. Cloning and tissue distribution of the human P2Y1 receptor. Biochem. Biophys. Res. Commun. 1996, 221, 588-593.
6. 1 purinoceptor. Biochem. Biophys. Res. Commun. 1996, 218, 783-788.
7. Burnstock, G.; King, B. F. Numbering of cloned P2 purinoceptors. Drug Dev. Res. 1998, 38, 67-71.
8. Communi, D.; Govaerts, C.; Parmentier, M.; Boeynaems, J. M. Cloning of a human purinergic P2Y receptor coupled to phospholipase C and adenylyl cyclase. J. Biol. Chem. 1997, 272, 31969-31973.
9. Lazarowski, E. R.; Homolya, L.; Boucher, R. C.; Harden, T. K. Direct demonstration of mechanically induced release of cellular UTP and its implication for uridine nucleotide receptor activation. J. Biol. Chem. 1997, 272, 24348-24354.
10. Harden, T. K.; Hawkins, P. T.; Stephens, L.; Boyer, J. L.; Downes, P. Phosphoinositide hydrolysis by guanosine 5′-(gamma-thio]triphosphate-activated phospholipase C of turkey erythrocyte membranes. Biochem. J. 1988, 252, 583-593.
11. 1 receptor mediates ADP-induced intracellular calcium mobilization and shape change in platelets. J. Biol. Chem. 1998, 273, 2030-2034.
12. 1 receptor is necessary for adenosine 5′-diphosphate-induced platelet aggregation. Blood 1998, 92, 152-159.
13. Crowley, M. R. Oxygen-induced pulmonary vasodilation is mediated by adenosine triphosphate in newborn lambs. J. Cardiovasc. Pharmacol. 1997, 30, 102-109.
14. Loubatières-Mariani, M.-M.; Hillaire-Buys, D.; Chapal, J.; Bertrand, G.; Petit, P. P2 purinoceptor agonists: New insulin secretagogues potentially useful in the treatment of noninsulin-dependent diabetes mellitus. In Purinergic Approaches in Experimental Therapeutics; Jacobson, K. A., Jarvis, M. F., Eds.; Wiley: New York, 1997; pp 253-260.
15. 1-receptors in human platelets which are pharmacologically distinct from P2Y(ADP)-receptors. Br. J. Pharmacol. 1998, 124, 157-164.
16. 2/3 receptors. Mol. Pharmacol. 1998, 53, 969-973.
17. 7 nucleotide receptor: high selectivity for the human versus rat receptor homologues. Mol. Pharmacol. 1998, 54, 22-32.
18. Kim, Y.-C.; Camaioni, E.; Ziganshin, A. U.; Ji, X.-J.; King, B. F.; Wildman, S. S.; Rychkov, A.; Yoburn, J.; Kim, H.; Mohanram, A.; Harden, T. K.; Boyer, J. L.; Burnstock, G.; Jacobson, K. A. Synthesis and structure activity relationships of pyridoxal-6-azoaryl-5′-phosphate and phosphonate derivatives as P2 receptor antagonists. Drug Dev. Res., in press.
19. 1 receptor. Mol. Pharmacol. 1996, 50, 1323-1329.
20. 1 receptors. J. Med. Chem. 1998, 41, 183-190.
21. 6-methyl 2′-deoxyadenosine 3′,5′-bisphosphate. Brit. J. Pharmacol. 1998, 124, 1-3.
22. Boyer, J. L.; Lazarowski, E.; Chen, X.-H.; Harden, T. K. Identification of a P2Y-purinergic receptor that inhibits adenylyl cyclase but does not activate phospholipase C. J. Pharmacol. Exp. Ther. 1993, 267, 1140-1146.
23. Boyer, J. L.; Mohanram, A.; Deleney, S.; Waldo, G.; Harden, T. K. Signaling mechanism and pharmacological selectivity of an avian P2 receptor. Nucleotides and their receptors in the nervous system; Leipzig, Germany, Aug 1, 1998; Abstact A03.
24. Cristalli, G.; Vittori, S.; Eleuteri, A.; Volpini, R.; Camaioni, E.; Lupidi, G. Synthesis of 2′-deoxynucleoside derivatives of 1-deazapurine. Nucleosides Nucleotides 1994, 13, 835-848.
25. Verheggen, I.; van Aerschot, A.;Toppet, S.; Snoeck, R.; Janssen, G.; Balzarini, J.; de Clercq, E.; Herdewijn, P. Synthesis and antiherpes virus activity of 1,5-anhydrohexitol nucleosides. J. Med. Chem. 1993, 36, 2033-2040.
26. Messini, L.; Tiwari, K. N.; Montgomery, J. A.; Secrist, J. A. III. Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides; 13th International Round Table on Nucleosides, Nucleotides and their Biological Applications; Sept. 6-10, 1998.
27. Shealy, Y. F.; O'Dell, C. A. Carbocyclic Analogues of 2′-Deoxyadenosine. Tetrahedron Lett. 1969, 2231-2234.
28. Hobins, M. J.; Fouron, Y.; Mengel, R. Adenosine 2′,3′-riboepoxide. Synthesis, intramolecular degradation, and transformation into 3′-substituted xylofuranosyl nucleosides and the lyxoepoxide. J. Org. Chem. 1974, 39, 1564-1570.
29. Robins, M. J.; Uza'nski, B. Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived nucleosides. Can. J. Chem. 1981, 59, 2601-2607.
30. van Aerschot, A.; Mamos, P.; Weyns, N.; Ikeda, S.; de Clercq, E.; Herdewijn, P. Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents. J. Med. Chem. 1993, 36, 2938-2942.
31. Hoffman, D. J.; Whistler, R. L. Synthesis and properties of nucleotides containing 4-thio-D-ribofuranoside. Biochemistry 1970, 9, 2367-2372.
32. Hancox, E. L.; Walker, R. T. Some reactions of 4′-thionucleosides and their sulfones. Nucleosides Nucleotides 1996, 15, 1-3.
33. Fischer, B.; Boyer, J. L.; Hoyle, C. H. V.; Ziganshin, A. U.; Brizzolara, A. L.; Knight, G. E.; Zimmet, J.; Burnstock, G.; Harden, T. K.; Jacobson, K. A. Identification of potent, selective P2Y-purinoceptor agonists - structure-activity-relationships for 2-thioether derivatives of adenosine 5′-triphosphate. J. Med. Chem. 1993, 36, 3937-3946.
34. Boyer, J. L.; Siddiqi, S.; Fischer, B.; Romero-Avila, T.; Jacobson, K. A.; Harden, T. K. Identification of potent P2Y-purinoceptor agonists that are derivatives of adenosine 5′-monophosphate. Br. J. Pharmacol. 1996, 118, 1959-1964.
35. 1 receptor. J. Med. Chem. 1998, 41, 102-108.
36. Jasper, J. R.; Insel, P. A. Evolving concepts of partial agonism. The beta-adrenergic receptor as a paradigm. Biochem. Pharmacol. 1992, 43, 119-130.
37. 2 receptors: Ligand development aided by molecular modeling and mutagenesis. Prog. Brain Res., in press.
38. 1 receptors. J. Med. Chem. 1998, 41, 2201-2206.
39. 2Y purinergic receptor agonists and guanine nucleotides. J. Biol. Chem. 1989, 264, 884-890.