Molecular recognition of modified adenine nucleotides by the P2Y1-receptor. 1. A synthetic, biochemical, and NMR approach

Journal of Medicinal Chemistry

Volumn 42, Issue 26, 1999, Pages 5325-5337

  Halbfinger, Efrat ^a   Major, Dan T ^a   Ritzmann, Marco ^b   Ubl, Joachim ^b   Reiser, Georg ^b   Boyer, Jose L ^c   Harden, Kendall T ^c   Fischer, Bilha ^a  

^a BAR ILAN UNIVERSITY   (Israel)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

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

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE NUCLEOTIDE; ADENOSINE PHOSPHATE; ADENOSINE TRIPHOSPHATE; CALCIUM; INOSITOL PHOSPHATE; PHOSPHOLIPASE C; PURINE P2Y RECEPTOR;

ANIMAL CELL; ARTICLE; CHEMICAL BOND; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; LIGAND BINDING; MOLECULAR RECOGNITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; RECEPTOR AFFINITY; STEREOSPECIFICITY;

ADENINE NUCLEOTIDES; ANIMALS; ASTROCYTES; CALCIUM; ENZYME ACTIVATION; ERYTHROCYTES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR CONFORMATION; PHOSPHOLIPASE C; RATS; RATS, WISTAR; RECEPTORS, PURINERGIC P2; TUMOR CELLS, CULTURED; TURKEYS;

EID: 0033619998     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990156d     Document Type: Article

References (51)

1. (a) Burnstock, G. Purinergic nerves. Pharmacol. Rev. 1972, 24, 509-581.
2. (b) Chan, C. M.; Unwin, R. J.; Burnstock, G. Potential functional roles of extracellular ATP in kidney and urinary tract. Exp. Nephrol. 1998, 6, 200-207.
3. (c) Boarder, M. R.; Hourani, S. M. O. The regulation of vascular function by P2 receptors: multiple site and multiple receptors. Trends Pharmacol. Sci. 1998, 19, 99-107.
4. (d) Inoue, K. The function of ATP receptors in the hippocampus. Pharmacol. Res. 1998, 38, 323-331.
5. (e) Abbrachio, M. P. P1 and P2 receptors in cell growth and differentiation. Drug Dev. Res. 1996, 39, 393-406.
6. (f) Bhagwat, S. S.; Williams, M. P2 purine and pyrimidine receptors: emerging superfamilies of G-protein and ligand-gated ion channels receptors. Eur. J. Med. Chem. 1997, 32, 183-193.
7. (a) Hoyle, C. H. V.; Burnstock, F. ATP receptors and their physiological roles. In Adenosine in the Nervous System; Stone, T. W., Ed.; Academic Press Ltd.: London, 1991; pp 43-47.
8. (b) Barnard, E. A.; Simon, J.; Webb, T. E. Nucleotide receptors in the nervous system- An abundant component using diverse transduction mechanisms. Mol. Neurobiol. 1997, 15, 103-129.
9. Zimmerman, H. Signaling via ATP in the nervous system. Trends Neurosci. 1994, 17, 420.
10. Edwards, F. A.; Gibb, A. J.; Colquhoun, D. ATP receptor-mediated synaptic currents in the central nervous system. Nature 1992, 359, 144-147.
11. (a) Abbracchio, M. P.; Burnstock, G. Purinoceptors: are there families of P2X and P2Y Purinoceptors? Pharmacol. Ther. 1994, 64, 445-475.
12. (b) Fredholm, B. B.; Burnstock, G.; Harden, T. K.; Spedding, M. P2-receptor nomenclature. Drug Dev. Res. 1996, 39, 461-466.
13. Neary, J. T.; Maccarthy, M.; Kang Y.; Zuniga, S. Mitogen signaling from P1 and P2 purinergic receptors to mitogen-activated protein kinase in human fetal astrocyte cultures. Neurosci. Lett. 1998, 242, 159-162.
14. Fischer, B. Therapeutic applications of ATP-(P2)-receptors agonists and antagonists. Exp. Opin. Ther. Patents 1999, 9, 385-399.
15. (a) Burnstock, G.; Cusack, N. J.; Meldrum, L. A. Effects of phosphorothioate analogues of ATP, ADP and AMP on guinea-pig taenia coli and urinary bladder. Br. J. Pharmacol. 1984, 82, 369-374.
16. (b) Uri, A.; Jarlebark, L.; Von Kugelgen, I.; Schonberg, T.; Unden, A.; Heilbronn, E. A new class of compounds, peptide derivatives of adenosine 5′-carboxylic acid, includes inhibitors of ATP receptor-mediated responses. Bioorg. Med. Chem. 1994, 2, 1099-1105.
17. (c) Jarlebark, L.; Erlandsson, M.; Uri, A. King, B. F.; Ziganshin, A. U.; Johansson, C.; Heilbronn, E. Peptidyl conjugates of adenosine 5′-carboxylic acid synthesized and evaluated as ligands for P2 purinoceptors. Biochem. Biophys. Res. Commun. 1996, 229, 363-369.
18. (d) Pehk, T.; Uri, A. Synthesis and structural chracterization of conjugates of adenosine and tetra-aspartate, novel analogues of ATP. Bioorg. Med. Chem. Lett. 1997, 7, 2159-2164.
19. Burnstock, G.; Fischer, B.; Hoyle, C. H. V.; Maillard, M.; Ziganshin, A. V.; Brizzolara, A. L.; von Isakovics, A.; Boyer, J. L.; Harden, T. K.; Jacobson, K. A. Structure activity relationship for derivatives of adenosine 5′-triphosphate as agonists at P2-purinoceptors: heterogeneity within P2X and P2Y subtypes. Drug Dev. Res. 1994, 31, 206-219.
20. (a) Fischer, B.; Boyer, J. L.; Hoyle, C. H. V.; Ziganshin, A. V.; 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.
21. (b) Boyer, J. L.; O'Tuel, 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.
22. (a) 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.
23. (b) Fischer, B.; Yefidoff, R.; Major, D. T.; Rutman-Halili, I.; Shneyyays, V.; Zinman, T.; Jacobson, K. A.; Shainberg A. Characterization of 'mini-nucleotides' as P2X-receptor agonists in rat cardiocytes culture. An integrated synthetic, biochemical and theoretical study. J. Med. Chem. 1999, 42, 2685-2696.
24. (a) Zimmet, J.; Järlebark, L.; 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.
25. (b) Gendron, F.-P.; Halbfinger, E.; Fischer, B.; D'Orleans-Juste, P.; Duval, M.; Beaudoin, A. R. Unpublished results.
26. Scott, S.-P.; Tanaka, J. C. Molecular interaction of 3′,5′-cyclic purine analogues with the binding site of retinal rod ion channels. Biochemistry 1995, 34, 2338-2347.
27. Brown, R. L.; Bert, R. J.; Evans, F. E.; Karpen, J. W. Activation of retinal rod cGMP-gated channels: what makes for an effective 8-substituted derivative of cGMP? Biochemistry 1993, 32, 10089-10095.
28. Nair, V.; Richerdson, S. G. Modification of nucleic acid bases via radical intermediates: synthesis of dihalogenated purine nucleosides. Synthesis 1982, 670-672.
29. Robins, M. J.; Uznanski, B. Nucleic acid related compounds. 33. Conversion of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides. Can. J. Chem. 1981, 59, 2601-2606.
30. Ikemoto, T.; Haze, A.; Hatano, H.; Kitamoto, Y.; Ishida, M.; Nara, K. Phosphorylation of nucleosides with phosphorous oxychloride in trialkyl phosphate. Chem. Pharm. Bull. 1995, 43, 210-215.
31. Kikugawa, K.; Suehiro, H.; Ichino, M. Platelet aggregation inhibitors. 6. 2-Thioadenosine derivatives. J. Med. Chem. 1973, 16, 1381-88.
32. 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, 1959-69 and references therein.
33. Burnstock, G. The past, present and future of purine nucleotides as signaling molecules. Neuropharmacology 1997, 36, 13-18.
34. 2+ responses. Biochem. J. 1996, 310, 215-219.
35. Lin, T.-A.; Lustig, K. D.; Sportiello, M. G.; Weisman, G. A.; Sun, G. Y. Signal transduction pathways coupled to a P2U receptor in neuroblastoma X glioma (NG 108-15) cells. J. Neurochem. 1993, 60, 1115-1125.
36. (a) Davies, B. D. Conformation of nucleosides and nucleotides. Prog. NMR Spectrosc. 1978, 12, 135-225.
37. (b) Ikehara, M.; Uesugi, S.; Yoshida, K. Studies on the conformation of purine nucleosides and their 5′-phosphates. Biochemistry, 1972, 11, 830-836.
38. 31P) fast Fourier transform nuclear magnetic resonance methods and conformational energy calculations. J. Am. Chem. Soc. 1974, 96, 7337-7348.
39. (a) Evans, F. E.; Kaplan, N. O. 8-Alkylaminoadenyl nucleotides as probes of dehydrogenase interactions with nucleotide analogues of different glycosyl conformation. J. Biol. Chem. 1976, 251, 6791-6797.
40. (b) Neidle, S.; Sanderson, M. R.; Subbiah, A.; Chattopadhyaya, J. B.; Kuroda, R.; Reese, C. B. 9-β-D-arabinofuranosyl-8-n-butylaminoadenine, a C-8 substituted nucleoside in the anti conformation. Crystallographic and NMR studies. Biochim. Biophys. Acta 1979, 565, 379-386.
41. 2+ response evoked by ATP and other nucleotides in mammalian brain astrocytes. Br. J. Pharmacol. 1997, 121, 1700-1706.
42. King, B. F.; Neary, J. T.; Zhu, Q.; Wang, S.; Norenberg, M. D.; Burnstock, G. P2 purinoceptors in rat cortial astrocytes: expression, calcium-imaging and signaling studies. Neuroscience 1996, 74, 1187-1196.
43. 1-receptor. 2. A computational approach. J. Med. Chem. 1999, 42, 5338-5347.
44. (a) Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984; pp 404-405;
45. (b) p 21.
46. (a) van Rhee, M. A.; Fischer, B.; van Galen, P. G. M.; Jacobson, K. A. Modelling the P2Y purinoceptor using rhodopsin as template. Drug Des. Discovery 1995, 13, 133-154.
47. 1 receptor: Molecular modeling and site-directed mutagenesis as tools to identify agonist and antagonist recognition sites. J. Med. Chem. 1998, 41, 1456-1466.
48. Hamprecht, B.; Löffler, F. Primary glial cultures as a model for studying hormone action. Methods Enzymol. 1985, 109, 341-345.
49. Reiser, G. Neuroblastoma cells. In Practical Electrophysiological Methods; Kettenmann, H., Grantyn, R., Eds.; Wiley-Liss: New York, 1992; pp 11-116.
50. Boyer, J. L.; Downes, C. P.; Harden, T. K. Kinetics of activation of phospholipase C by P2Y purinergic receptor agonists and guanine nucleotides. J. Biol. Chem. 1989, 264, 884-890.
51. Harden, T. K.; Hawkins, P. T.; Stephens, L.; Boyer, J. L.; Downes, C. P. Phosphoinositide hydrolysis by guanosine 5′-[gamma-thio]triphosphate-activated phospholipase C of turkey erythrocyte membranes. Biochem. J. 1988, 252, 583-93.