Novel inhibitors of nucleoside triphosphate diphosphohydrolases: Chemical synthesis and biochemical and pharmacological characterizations

Journal of Medicinal Chemistry

Volumn 43, Issue 11, 2000, Pages 2239-2247

  Gendron, Fernand Pierre ^a   Halbfinger, Efrat ^b   Fischer, Bilha ^b   Duval, Martine ^c   D'Orléans Juste, Pédro ^c   Beaudoin, Adrien R ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b BAR ILAN UNIVERSITY   (Israel)

^c UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE DERIVATIVE; HYDROLASE; NUCLEOSIDE TRIPHOSPHATE; PURINE RECEPTOR;

ARTICLE; ASTROCYTE; BLOOD PRESSURE; CHEMICAL ANALYSIS; ENZYME INHIBITION; ENZYME SYNTHESIS; ERYTHROCYTE; HYDROLYSIS; NONHUMAN; RAT;

ADENOSINE TRIPHOSPHATE; ANIMALS; APYRASE; CATTLE; ENZYME INHIBITORS; FEMALE; GUINEA PIGS; HYDROLYSIS; KINETICS; MALE; MESENTERIC ARTERIES; RATS; RECEPTORS, PURINERGIC P2; VASODILATION;

EID: 0034214125     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000020b     Document Type: Article

References (61)

1. Dubyak, G. R.; El Moatassim, C. Signal transduction via P2-purinergic receptors for extracellular ATP and other nucleotides. Am. J. Physiol. 1993, 265, C577-C606.
2. El Moatassim, C. E.; Dornand, J.; Mani, J.-C. Extracellular ATP and cell signaling. Biochim. Biophys. Acta 1992, 1134, 31-45.
3. Motte, S.; Commun, D.; Pirotton, S.; Boeynaems, J. M. Involvement of multiple receptors in the actions of extracellular ATP: the example of vascular endothelial cells. Int. J. Biochem. Cell Biol. 1995, 27, 1-7.
4. North, R. A.; Barnard, E. A. Nucleotide receptors. Curr. Opin. Neurobiol. 1997, 7, 346-357.
5. Rubino, A.; Burnstock, G. Evidence for a P2-purinoceptor mediating vasoconstriction by UTP, ATP and related nucleotides in the isolated pulmonary vascular bed of the rat. Br. J. Pharmacol. 1996, 118, 1415-1420.
6. Fijnheer, R.; Boomgaard, M. N.; van den Eertwegh, A. J.; Homburg, C. H.; Gouwerok, C. W.; Veldman, H. A.; Roos, D.; de Korte, D. Stored platelets release nucleotides as inhibitors of platelet function. Thromb. Haemost. 1992, 68, 595-599.
7. Luthje, J. Origin, metabolism and function of extracellular adenine nucleotides in the blood. Kiln. Wochenschr. 1989, 67, 317-327.
8. Traut, T. W. Physiological concentrations of purines and pyrimidines. Mol. Cell. Biochem. 1994, 140, 1-22.
9. Abbracchio, M. P.; Burnstock, G. Purinoceptors: are there families of P2X and P2Y purinoceptors? Pharmacol. Ther. 1994, 64, 445-475.
10. Boarder, M. R.; Hourani, S. M. O. The regulation of vascular function by P2 receptors: Multiple sites and multiple receptors. Trends Pharmacol. Sci. 1998, 19, 99-107.
11. Fischer, B. Therapeutic applications of ATP-(P2)-receptors agonists and antagonists. Expert Opin. Ther. Patents 1999, 9. 385-399.
12. 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, 143-152.
13. Fredholm, B. B.; Abbracchio, M. P.; Burnstock, G.; Dubyak, G. R.; Harden, T. K.; Jacobson, K. A.; Schwabe, U.; Williams, M. Towards a revised nomenclature for Pl and P2 receptors. Trends Pharmacol. Sci. 1997, 18, 79-82.
14. Rongen, G. A.; Floras, J. S.; Lenders, J. W. M.; Thien, T.; Smits, P. Cardiovascular pharmacology of purines. Clin. Sci. 1997, 92, 13-24.
15. Beaudoin, A. R.; Sévigny, J.; Picher, M. ATP diphosphohydrolases, apyrases and nucleotide phosphohydrolases: Biochemical properties and functions. In Biomembrane; Lee, A. G., Ed.; JAI: Greenwich, CT, 1996; Vol. 5, pp 369-401.
16. Beaudoin, A. R.; Grondin, G.; Enjyoji, K.; Robson, S. C.; Sévigny. J.; Fischer, B.; Gendron, F.-P. Physiological role of NTPDases (ATP diphosphohydrolases) in mammals. Proceeding of the 2nd International Workshop on ecto-ATPase and related nucleotidases. Diepenbeek, Belgium, 14-18 June 1999; Vanduffel L., Lemmens, R., Eds.; Shaker Publishing B. V.: The Netherlands, 2000; pp 125-135.
17. Plesner, L. Ecto-ATPases: identities and functions. Int. Rev. Cytol. 1995, 158, 141-214.
18. Vlajkovic, S. M.; Thorne, P. R.; Hously, G. D.; Munoz, D. J. B.; Kendrick, I. S. Ecto-nucleotidases terminate purinergic signaling in the cochlear endolymphatic compartment. Neuroreport 1998, 9, 1559-1565.
19. Zimmermann, H. 5′-Nucleotidase: Molecular structure and functional aspects. Biochem. J. 1992, 285, 345-365.
20. Christoforidis, S.; Papamarcaki, T.; Galaris, D.; Kellner, R.; Tsolas, O. Purification and properties of human placental ATP diphosphohydrolase. Eur. J. Biochem. 1995, 234, 66-74.
21. LeBel, D.; Poirier, G. G.; Phaneuf, S.; St-Jean, P.; Laliberté, J.-F.; Beaudoin, A. R. Characterization and purification of a calcium sensitive ATP diphosphohydrolase from the pig pancreas. J. Biol. Chem. 1980, 255, 1227-1233.
22. Sévigny, J.; Côté, Y. P.; Beaudoin, A. R. Purification of pancreas type I ATP diphosphohydrolase and identification by affinity labeling with 5′-p-fluorosulfonyl benzoyl adenosine ATP analogue. Biochem. J. 1997, 312, 351-356.
23. Sévigny, J.; Levesque, F. R.; Grondin, G.; Beaudoin, A. R. Purification of the blood vessel ATP diphosphohydrolase, identification and localization by immunological techniques. Biochim. Biophys. Acta 1997, 1334, 73-88.
24. Sévigny, J., Dumas, F., and Beaudoin, A. R. Purification and identification by immunological techniques of different isoforms of mammalian ATP diphosphohydrolase. In Ecto-ATPase; Plesner, L., Kirley, T. L., Knowles, A. F., Eds.; Plenum Press: New York, 1997; pp 143-151.
25. Kaczmarek, E.; Koziack, K.; Sévigny, J.; Siegel, J. B.; Anrather, J.; Beaudoin, A. R.; Bach, F. H.; Robson, S. C. Identification and characterization of CD39/vascular ATP diphosphohydrolase. J. Biol. Chem. 1996, 271, 33116-33122.
26. Maliszewski, C. R.; Delespesse, G. L.; Schoenborn, M. A.; Armitage, R. J.; Fanslow, W. C.; Nakajima, T.; Baker, E.; Sutherland, G. R.; Poindexter, K.; Birks, C.; Alpert, A.; Friend, D.; Gimpel, S. D.; Gayle, R. B., III. The CD39 lymphoid cell activation antigen: Molecular cloning and structural characterization. J. Immunol. 1994, 153, 3574-3583.
27. 2+)-apyrase. J. Biol. Chem. 1996, 271, 9898-9901.
28. Enjyoji, K.; Sévigny, J.; Lin, Y.; Fenette, P. S.; Christie, P. D.; Schulteam Esch, J., II; Imai, M.; Edelberg, J. M.; Rayburn, H.; Lech, M.; Beller, D. L.; Csizmadia, E.; Wagner, D. D.; Robson, S. C.; Rosenburg, R. D. Tartgeted disruption of cd39/ATP diphosphohydrolase results in disordered hemostasis and thromboregulation. Nature Med. 1999, 5, 101-1017.
29. Dowd, F. J.; Murphy, H. C.; Li, L. Metabolism of extracellular ATP by rat parotids cells. Arch. Oral Biol. 1996, 41, 855-862.
30. Kegel, B.; Braun, N.; Heine, P.; Maliszewski, C. R.; Zimmermann, H. An ecto-ATPase and an ecto-ATP diphosphohydrolase are expressed in rat brain. Neuropkarmacol. 1997, 36, 1189-1200.
31. Kennedy, C.; Leff, P. How should P2X purinoceptors be classified pharmacologically. Trends Pharmacol. Sci. 1995, 16, 168-174.
32. Welford, L. A.; Cusack, N. J.; Hourani, S. M. O. The structure-activity relationships of ectonucleotidases and of excitatory P2-purinoceptors: Evidence that the dephosphorylation of ATP analogues reduces pharmacological potency. Eur. J. Pharmacol. 1987, 141, 123-130
33. Ziganshin, A. U.; Hoyle, C. H. V.; Burnstock, G. Ecto-enzymes and metabolism of extracellular ATP. Drug. Dev. Res. 1994, 32, 134-146.
34. Picher, M.; Sévigny, J.; D'Orléans-Juste, P.; Beaudoin, A. R. Hydrolysis of P2-purinoceptor agonists by a purified ectonucleotidase from the bovine aorta, the ATP diphosphohydrolase. Biochem. Pharmacol. 1996, 51, 1453-1460.
35. Zimmet, J.; Jarlebark, L.; Hammarberg, T.; van Galen, P. J. M.; Jacobson, K. A.; Heilbronn, E. Synthesis and biological activity of novel 2-thio derivatives of ATP. Nucleosides Nucleotides 1993, 12, 1-20
36. Boyer, J. L.; Otuel, J. W.; Fischer, B.; Jacobson, K. A.; Harden, T. K. 2-Thioether derivatives of adenine nucleotides are exceptionally potent agonists at adenylyl cyclase-linked P2Y-purinoceptors. Br. J. Pharmacol. 1995, 116, 2611-2616.
37. Burnstock, G.; Fischer, B.; Hoyle, C. H. V.; Maillard, M.; Ziganshin, A. U.; Brizzolara, A. L.; von Isakovics, A.; Boyer, J. L.; Kendall, T. H.; Jacobson, K. A. Structure-activity relationships for derivatives of adenosine 5′-triphosphate as agonist of P2-purinoceptors: Heterogeneity within P2X and P2Y subtypes. Drug Dev. Res. 1994, 31, 206-219.
38. Fischer, B.; Boyer, J. L.; Hoyle, C. H.; 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.
39. 1-receptor. Part I. A synthetic, biochemical, and NMR approach. J. Med. Chem. 1999, 42, 5325-5337.
40. Fischer, B.; Chulkin, A.; Boyer, J. L.; Harden, K. T.; Gendron, F.-P.; Beaudoin, A. R.; Chapal, J.; Hillaire-Buys, D.; Petit, P. 2-thioether-5′-O-(1-thiotriphosphate) adenine derivatives as new insulin secretagogues acting through P2Y-receptors. J. Med. Chem. 1999, 42, 3636-3646.
41. Fischer, B.; Kabha, E.; Gendron, F.-P.; Beaudoin, A. R. Synthesis, mechanism and fluorescent properties of 8-(aryl)3-β-D-ribufuranosylimidazo[2,1-i] purine 5′-phosphate derivatives. Nucleosides Nucleotides. In press.
42. Côté, Y. P.; Pavate, C.; Beaudoin, A. R. The control of nucleotides in blood vessels: Role of the ATP diphosphohydrolase (apyrase). Curr. Top. Pharmacol. 1992, 1, 83-92.
43. Dixon, M.; Webb, E. C. Enzyme, 3rd ed.; Academic Press: New York, 1979; p 1116.
44. Crack, B. E.; Beukers, M. W.; McKechnie, K. C. W.; Ijzerman, A. P.; Left, P. Pharmacological analysis of ecto-ATPase inhibition: Evidence for combined enzyme inhibition and receptor antagonism in P2X-purinoceptor ligands. Br. J. Pharmacol. 1994, 273, 24814-24821.
45. Siefert, R.; Schultz, G. Involvement of pyrimidinoceptors in the regulation of cell functions by uridine and uracil nucleotides. Trends Pharmacol. Sci. 1989, 10, 365-369.
46. Stone, T. W. Receptors for adenosine and adenine nucleotides. Gen. Pharmacol. 1991, 22, 25-31.
47. Cusack, N. J.; Hourani, S. M. O. Some pharmacological and biochemical interactions of the enantiomers of adenylyl 5′-(β, γ-methylene)-diphosphate with the guinea-pig urinary bladder. Br. J. Pharmacol. 1984, 82, 155-159.
48. Cusack, N. J.; Hourani, S. M. O.; Welford, L. A. ATP analogues and the guinea-pig urinary bladder: Pharmacological potency is related to resistance to breakdown by ectoenzymes. Br. J. Pharmacol. 1986, 89, 514p.
49. Hourani, S. M. O.; Welford, L. A.; Cusack, N. J. L-AMP-PCP an ATP receptor agonist in guinea-pig bladder, is inactive on taenia coli. Eur. J. Pharmacol. 1985, 1008, 197-200.
50. Major, D. T.; Halbfinger, E.; Fischer, B. Molecular recognition of modified adenine nucleotides by the P2Y1-receptor. II. A computational approach. J. Med. Chem. 1999, 42, 5338-5347.
51. Van Rhee, A. M.; Fischer, B.; Van Galen, P. J. M.; Jacobson, K. A. Modelling the P2Y purinoceptor using rhodopsin as template. Drug Design Delivery 1995, 13, 133-154.
52. Westley, J. Enzymatic Catalysis; Harper and Row: New York, 1969.
53. Stout, J. G.; Kirley, T. L. Control of cell membrane ecto-ATPase by oligomerization state-Intermolecular cross-linking modulates ATPase activity. Biochemistry 1996, 35, 8289-8298.
54. Wang, T. F.; Ou, Y.; Guidotti, G. The transmembrane domains of ecto-apyrase (CD39) affects its enzymatic activity and quaternary structure. J. Biol. Chem. 1998, 273, 24814-24821.
55. Hirst, G. D. S.; Jobling, P. The distribution of γ-adrenoceptors and P2 purinoceptors in mesenteric arteries and vains of the guinea-pig. Br. J. Pharmacol. 1989, 96, 993-999.
56. Onaka, U.; Fujii, K.; Abe, I.; ; Fujishima, M. Enhancement by exogenous and locally generated angiotensin II of purinergic neurotransmission via angiotensin type 1 receptor in the guinea-pig isolated mesenteric artery. Br. J. Pharmacol. 1997, 122, 942-948.
57. Fujii, K. Evidence for adenosine triphosphate as an excitatory transmitter in guinea-pig, rabbit and pig urinary bladder. J. Physiol. 1989, 404, 39-52.
58. Ishikawa, S. Actions of ATP and α, β-methylene ATP on neuromuscular transmission and smooth muscle membrane of the rabbit and guinea-pig mesenteric arteries. Br. J. Pharmacol. 1985, 86, 777-787.
59. Berthiaume, N.; Claing, A.; Regoli, D.; Warner, T. D.; D'Orléans-Juste, P. Charaterization of receptors for kinins and neurokinins in the arterial and venous mesenteric vasculatures of the guinea-pig. Br. J. Pharmacol. 1995, 115, 1319-1325.
60. Baykov, A. A.; Evtushenko, O. A.; Avaeve, S. M. Malachite green procedure for orthophosphate determination and its use in alkaline phosphatase-based enzyme immunoassay. Anal. Biochem. 1988, 171, 266-270.
61. Bradford, M. M. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.