Boranophosphate isoster controls P2Y-receptor subtype selectivity and metabolic stability of dinucleoside polyphosphate analogues

Journal of Medicinal Chemistry

Volumn 55, Issue 1, 2012, Pages 437-448

  Yelovitch, Shir ^a   Camden, Jean ^b   Weisman, Gary A ^b   Fischer, Bilha ^a  

^a BAR ILAN UNIVERSITY   (Israel)

^b University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANOPHOSPHATE ISOSTER; DINUCLEOSIDE POLY(BORANO)PHOSPHATE DERIVATIVE; NUCLEIC ACID BASE; POLYPHOSPHATE; PURINERGIC P2Y RECEPTOR; PURINERGIC P2Y RECEPTOR AGONIST; PURINERGIC P2Y1 RECEPTOR; PURINERGIC P2Y4 RECEPTOR; PURINERGIC P2Y6 RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROLYSIS; ISOMER; RECEPTOR BINDING;

ANIMALS; BORANES; CALCIUM; CELL LINE, TUMOR; DINUCLEOSIDE PHOSPHATES; DRUG STABILITY; HUMANS; HYDROLYSIS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOSPHORIC DIESTER HYDROLASES; PURINERGIC P2Y RECEPTOR AGONISTS; PYROPHOSPHATASES; RECEPTORS, PURINERGIC P2Y; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TURKEY;

EID: 84855845664     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2013198     Document Type: Article

References (34)

1. Zamecnik, P. C.; Stephenson, M. L.; Janeway, C. M.; Randerath, K. Enzymatic synthesis of diadenosine tetraphosphate and diadenosine triphosphate with a purified lysyl-sRNA synthetase Biochem. Biophys. Res. Commun. 1966, 24, 91-97
2. Randerath, K.; Janeway, C. M.; Stephenson, M. L.; Zamecnik, P. C. Isolation and characterization of dinucleoside tetra- and tri-phosphates formed in the presence of lysyl-sRNA synthetase Biochem. Biophys. Res. Commun. 1966, 24, 98-105
3. Pintor, J.; Rotllan, P.; Torres, M.; Miras-Portugal, M. T. Characterization and quantification of diadenosine hexaphosphate in chromaffin cells: granular storage and secretagogue-induced release Anal. Biochem. 1992, 200, 296-300
4. McLennan, A. G. Dinucleoside polyphosphates-friend or foe? Pharmacol. Ther. 2000, 87, 73-89
5. Jankowski, V.; van der Giet, M.; Mischak, H.; Morgan, M.; Zidek, W.; Jankowski, J. Dinucleoside polyphosphates: strong endogenous agonists of the purinergic system Br. J. Pharmacol. 2009, 157, 1142-1153
6. Flores, N. A.; Stavrou, B. M.; Sheridan, D. J. The effects of diadenosine polyphosphates on the cardiovascular system Cardiovasc. Res. 1999, 42, 15-26
7. Schlueter, H.; Offers, E.; Brueggemann, G.; van der Giet, M.; Tepel, M.; Nordhoff, E.; Karas, M.; Spieker, C.; Witzel, H.; Zidek, W. Diadenosine phosphates and the physiological control of blood pressure Nature (London) 1994, 367, 186-188
8. van der Giet, M.; Schmidt, S.; Tolle, M.; Jankowski, J.; Schluter, H.; Zidek, W.; Tepel, M. Effects of dinucleoside polyphosphates on regulation of coronary vascular tone Eur. J. Pharmacol. 2002, 448, 207-213
9. Hoyle, C. H. V.; Hilderman, R. H.; Pintor, J. J.; Schluter, H.; King, B. F. Diadenosine polyphosphates as extracellular signal molecules Drug Dev. Res. 2001, 52, 260-273
10. Flores, N. A.; Stavrou, B. M.; Sheridan, D. J. The effects of diadenosine polyphosphates on the cardiovascular system Cardiovasc. Res. 1999, 42, 15-26
11. Delicado Esmerilda, G.; Miras-Portugal, M. T.; Carrasquero Luz Maria, G.; Leon, D.; Perez-Sen, R.; Gualix, J. Dinucleoside polyphosphates and their interaction with other nucleotide signaling pathways Pfluegers Arch. 2006, 452, 563-572
12. Pintor, J.; Diaz-Hernandez, M.; Gualix, J.; Gomez-Villafuertes, R.; Hernando, F.; Miras-Portugal, M. T. Diadenosine polyphosphate receptors from rat and guinea-pig brain to human nervous system Pharmacol. Ther. 2000, 87, 103-115
13. Abbracchio, M. P.; Burnstock, G.; Boeynaems, J.-M.; Barnard, E. A.; Boyer, J. L.; Kennedy, C.; Knight, G. E.; Fumagalli, M.; Gachet, C.; Jacobson, K. A.; Weisman, G. A. International Union of Pharmacology LVIII: update on the P2Y G protein-coupled nucleotide receptors: from molecular mechanisms and pathophysiology to therapy Pharmacol. Rev. 2006, 58, 281-341
14. Shaver, S. R.; Rideout, J. L.; Pendergast, W.; Douglass, J. G.; Brown, E. G.; Boyer, J. L.; Patel, R. I.; Redick, C. C.; Jones, A. C.; Picher, M.; Yerxa, B. R. Structure-activity relationships of dinucleotides: potent and selective agonists of P2Y receptors Purinergic Signalling 2005, 1, 183-191
15. Pendergast, W.; Yerxa, B. R.; Douglass, J. G.; Shaver, S. R.; Dougherty, R. W.; Redick, C. C.; Sims, I. F.; Rideout, J. L. Synthesis and P2Y receptor activity of a series of uridine dinucleoside 5′-polyphosphates Bioorg. Med. Chem. Lett. 2001, 11, 157-160
16. Jacobson, K. A.; Boeynaems, J.-M. P2Y nucleotide receptors: promise of therapeutic applications Drug Discovery Today 2010, 15, 570-578
17. Jacobson, K. A.; Ivanov, A. A.; de Castro, S.; Harden, T. K.; Ko, H. Development of selective agonists and antagonists of P2Y receptors Purinergic Signalling 2009, 5, 75-89
18. 2 receptor agonist for the treatment of cystic fibrosis J. Pharmacol. Exp. Ther. 2002, 302, 871-880
19. Kikuta, Y.; Ohiwa, E.; Okada, K.; Watanabe, A.; Haruki, S. Clinical application of diadenosine tetraphosphate (Ap4A:F-1500) for controlled hypotension Acta Anaesthesiol. Scand. 1999, 43, 82-86
20. Maminishkis, A.; Jalickee, S.; Blaug, S. A.; Rymer, J.; Yerxa, B. R.; Peterson, W. M.; Miller, S. S. The P2Y(2) receptor agonist INS37217 stimulates RPE fluid transport in vitro and retinal reattachment in rat Invest. Ophthalmol. Visual Sci. 2002, 43, 3555-3566
21. 2 agonist in healthy subjects J. Ocul. Pharmacol. Ther. 2001, 17, 173-179
22. Nahum, V.; Tulapurkar, M.; Levesque, S. A.; Sevigny, J.; Reiser, G.; Fischer, B. Diadenosine and diuridine poly(borano)phosphate analogs: synthesis, chemical and enzymatic stability, and activity at P2Y1 and P2Y2 receptors J. Med. Chem. 2006, 49, 1980-1990
23. Jankowski, V.; Tolle, M.; Vanholder, R.; Schonfelder, G.; van der Giet, M.; Henning, L.; Schluter, H.; Paul, M.; Zidek, W.; Jankowski, J. Uridine adenosine tetraphosphate: a novel endothelium-derived vasoconstrictive factor Nat. Med. (N. Y.) 2005, 11, 223-227
24. Hoard, D. E.; Ott, D. G. Conversion of mono- and oligodeoxyribonucleotides to 5′-triphosphates J. Am. Chem. Soc. 1965, 87, 1785-1788
25. Nahum, V.; Fischer, B. Boranophosphate salts as an excellent mimic of phosphate salts: preparation, characterization, and properties Eur. J. Inorg. Chem. 2004, 4124-4131
26. Ludwig, J.; Eckstein, F. Synthesis of nucleoside 5′- O -(1,3-dithiotriphosphates) and 5′- O -(1,1-dithiotriphosphates) J. Org. Chem. 1991, 56, 1777-1783
27. Han, Q.; Gaffney, B. L.; Jones, R. A. One-flask synthesis of dinucleoside tetra- and penta-phosphates Org. Lett. 2006, 8, 2075-2077
28. Li, P.; Xu, Z.; Liu, H.; Wennefors, C. K.; Dobrikov, M. I.; Ludwig, J.; Shaw, B. R. Synthesis of α-P-modified nucleoside diphosphates with ethylenediamine J. Am. Chem. Soc. 2005, 127, 16782-16783
29. Vollmayer, P.; Clair, T.; Goding, J. W.; Sano, K.; Servos, J.; Zimmermann, H. Hydrolysis of diadenosine polyphosphates by nucleotide pyrophosphatases/phosphodiesterases Eur. J. Biochem. 2003, 270, 2971-2978
30. Yegutkin, G. G. Nucleotide- and nucleoside-converting ectoenzymes: important modulators of purinergic signalling cascade Biochim. Biophys. Acta, Mol. Cell Res. 2008, 1783, 673-694
31. Guranowski, A.; Sillero, A. In Ap4A and Other Dinucleoside Polyphosphates; McLennan, A. G., Ed; CRC Press: Boca Raton, FL, 1992; pp 84-95
32. Major, D. T.; Nahum, V.; Wang, Y.; Reiser, G.; Fischer, B. Molecular recognition in purinergic receptors. 2. Diastereoselectivity of the h-P2Y1-receptor J. Med. Chem. 2004, 47, 4405-4416
33. Kikugawa, K.; Suehiro, H.; Yanase, R.; Aoki, A. Platelet aggregation inhibitors. IX. Chemical transformation of adenosine into 2-thioadenosine derivatives Chem. Pharm. Bull. 1977, 25, 1959-1969
34. 2 nucleotide receptor. Consequences of truncation of the C terminus J. Biol. Chem. 1998, 273, 29437-29444