Deoxyadenosine bisphosphate derivatives as potent antagonists at P2Y1 receptors

Journal of Medicinal Chemistry

Volumn 41, Issue 2, 1998, Pages 183-190

  Camaioni, Emidio ^a   Boyer, José L ^b   Mohanram, Arvind ^b   Harden, T Kendall ^b   Jacobson, Kenneth A ^a,c  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

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

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

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; DEOXYADENOSINE DIPHOSPHATE; HYDROXYL GROUP; NUCLEOSIDE; PHOSPHATE; PHOSPHOLIPASE C; PURINE P2 RECEPTOR; PURINERGIC RECEPTOR BLOCKING AGENT; RIBOSE;

ANIMAL CELL; ARTICLE; ENZYME ACTIVATION; ERYTHROCYTE MEMBRANE; METHYLATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; TURKEY (BIRD);

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYADENINE NUCLEOTIDES; ERYTHROCYTE MEMBRANE; MODELS, CHEMICAL; PHOSPHOLIPASE C; RECEPTORS, PURINERGIC P2; STRUCTURE-ACTIVITY RELATIONSHIP; TURKEYS;

EID: 0031916069     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970433l     Document Type: Article

References (26)

1. Burnstock, G. Purinergic nerves. Pharmacol. Rev. 1972, 24, 509-81.
2. Fredholm, B. B.; Abbracchio, M. P.; Burnstock, G.; Daly, J. W.; Harden, T. K.; Jacobson, K. A.; Leff, P.; Williams, M. Nomenclature and classification of purinoceptors. Pharmacol. Rev. 1994, 46, 143-156.
3. Abbracchio, M. P.; Burnstock, G. Purinoceptors: are there families of P2x and P2y purinoceptors? Pharmacol. Ther. 1994, 64, 445-475.
4. Burnstock, G.; King, B. F. Numbering of cloned P2 purinoceptors. Drug Dev. Res. 1996, 38, 67-71.
5. 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.
6. 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.
7. Boyer, J. L.; Zohn, I. E.; Jacobson, K. A.; Harden, T. K. Differential-effects of P2-purinoceptor antagonists on phospholipase C-coupled and adenylyl cyclase-coupled P2Y-purinoceptors. Br. J. Pharmacol. 1994, 113, 614-620.
8. 1 receptor. Mol. Pharmacol. 1996, 50, 1323-1329.
9. Lee, Y. C.; Park, C. S.; Komatsu, K.; Kwack, J.; Strott, C. A. Adrenocortical pregnenolone binding activity resides with estrogen sulfotransferase. Endocrinology 1995, 136, 361-364.
10. Uchiyama, M.; Aso, Y.; Noyory, R.; Hayakawa, Y. O-Seletive phosphorylation of nucleosides without N-protection. J. Org. Chem. 1993, 58, 373-379.
11. Christensen, L. F.; Broom, A. D. Synthesis and biological activity of selected 2,6-disubstituted-(2-deoxy-α- and -β-D-erythro-pentofuranosyl)purines. J. Med. Chem. 1972, 15, 735-739.
12. Olivanen, M.; Lonnberg, H.; Zhou, X.-X.; Chattopadhyaya, J. Acidic hydrolysis of 6-substituted 9-(2-deoxy-β-D-erythro-pentofuranosyl)purines and their 9-(1-alkoxyethyl) counter-parts: kinetics and mechanism. Tetrahedron 1987, 43, 1133-1140.
13. Ikehara, M.; Uesugi, S.; Kaneco, M. 8-Bromoadenosine and its 5′-phosphate. Direct bromination of adenine nucleosides and nucleotides. In Nucleic Acid Chemistry; Townsend, L. B.; Tipson, R. S., Eds.; John Wiley and Sons: New York, 1978; Vol II, pp 837-841.
14. van der Wenden, E. M.; von Drabbe-Künzel, J. K.; Mathôt, R. A. A.; Danhof, M.; IJzerman, A. P.; Soudijn, W. Ribose-modified adenosine-analogs as potential partial agonists for the adenosine receptor. J. Med. Chem. 1995, 38, 4000-4006
15. Nair, V.; Richardson, S. G. Modification of nucleic acid bases via radical intermediates: synthesis of dihalogenated purine. Synthesis 1982, 670-672.
16. Holý, A.; Šorm, F. Nucleic acids and their analogues. LXXX. Preparation of nucleoside phosphites by reaction of nucleosides with triphenyl phosphite. Collect Czech. Chem. Commun. 1966, 31, 1544-1560.
17. Himmelsbach, F.; Charubala, R.; Pfleiderer, W. Bis[2-(p-nitrophenyl)ethyl]phosphorochloridate, a new versatile phosphorylating agent in nucleotide chemistry. Helv. Chim. Acta 1987, 70, 1286-1295.
18. Harden, T. K.; Hawkins, P. T.; Stephens, L.; Boyer, J. L.; Downes, P. Phosphoinositide hydrolysis by guanosine 5′-(gammathio)triphosphate-activated phospholipase C of turkey erythrocyte membranes. Biochem. J. 1988, 252, 583-593.
19. 2Y purinergic receptor agonists and guanine nucleotides. J. Biol. Chem. 1989, 264, 884-90.
20. Filtz, T. M.; Li, Q.; Boyer, J. L.; Nicholas, R. A.; Harden, T. K. Expression of a cloned P2Y purinergic receptor that couples to phospholipase-C. Mol. Pharmacol. 1994, 46, 8-14.
21. 2Y-subtypes. Drug Dev. Res. 1994, 31, 206-219.
22. 2Y purinoceptor using rhodopsin as template. Drug Des. Discovery 1995, 13, 133-154.
23. Jacobson, K. A.; Kim, Y.-C.; Camaioni, E.; van Rhee, A. M. Structure activity relationships of P2 receptor agonists and antagonists. Chapter 4 in The P2 Nucleotide Receptors, in the series The Receptors; Turner, J. T., Weisman, G., Fedan, J., Eds.; Humana Press: Clifton, NJ, 1997; pp 81-107.
24. Lambrecht, G.; Friebe, T.; Grimm, U.; Windscheif, U.; Bungardt, E.; Hildebrandt, C.; Baumert, H. G.; Spatzkumbel, G.; Mutschler, E. PPADS, a Novel Functionally Selective Antagonist of P2 Purinoceptor-Mediated Responses. Eur. J. Pharmacol. 1992, 217, 217-219.
25. Siddiqi, S. M.; Jacobson, K. A.; Esker, J. L.; Melman, N.; Tiwari, K. N.; Secrist, J. A.; Schneller, S. W.; Cristalli, G.; Johnson, C. A.; IJzerman, A. P. Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors. J. Med. Chem. 1995, 38, 1174-1188.
26. 3 adenosine receptor. Mol. Pharmacol. 1994, 45, 1101-1111.