2-Substitution of Adenine Nucleotide Analogues containing a Bicyclo[3.1.0]hexane Ring System Locked in a Northern Conformation: Enhanced Potency as P2Y1 Receptor Antagonists

Journal of Medicinal Chemistry

Volumn 46, Issue 23, 2003, Pages 4974-4987

  Kim, Hak Sung ^a,e   Ohno, Michihiro ^a   Xu, Bin ^a   Kim, Hea Ok ^b   Choi, Yongseok ^a   Ji, Xiao D ^a   Maddileti, Savitri ^d   Marquez, Victor E ^c   Harden, T Kendall ^d   Jacobson, Kenneth A ^a  

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

^b Seoul National University   (South Korea)

^c NATIONAL CANCER INSTITUTE   (United States)

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

^e Wonkwang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO N6 METHYLMETHANOCARBA 2' DEOXYADENOSINE 3',5' BISPHOSPHATE; 2 METHYLTHIOADENOSINE DIPHOSPATE; 4 (2 IODO 6 METHYLAMINOPURIN 9 YL) 1 [(PHOSPHATO)METHYL] 2 (PHOSPHATO)BICYCLO[3.1.0]HEXANE; ADENINE NUCLEOTIDE 3',5' BISPHOSPHATE; ADENINE NUCLEOTIDE DERIVATIVE; ADENOSINE DIPHOSPHATE; BICYCLO[3.1.0]HEXANE; HEXANE; METHANOCARBA N6 METHYL 2 IODINE DERIVATIVE; PHOSPHOLIPASE C; PURINE P2Y RECEPTOR; PURINE P2Y1 RECEPTOR; PURINE P2Y1 RECEPTOR ANTAGONIST; PURINERGIC RECEPTOR BLOCKING AGENT; RIBOSE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ASTROCYTOMA CELL; CELL MEMBRANE; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING; DRUG CONFORMATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; NONHUMAN; PHOSPHORYLATION; PROTEIN PHOSPHORYLATION; STRUCTURE ANALYSIS;

EID: 0242267908     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030127+     Document Type: Article

References (48)

1. von Kügelgen, I.; Wetter, A. Molecular pharmacology of P2Y-receptors.Naunyn Schmiedebergs Arch. Pharmacol. 2000, 362, 310-323.
2. Khakh, B. S.; Burnstock, G.; Kennedy, C.; King, B. F.; North, R. A.; Seguela, P.; Voigt, M.; Humphrey, P. P. International union of pharmacology. XXIV. Current status of the nomenclature and properties of P2X receptors and their subunits. Pharmacol. Rev. 2001, 53, 107-118.
3. Hollopeter, G.; Jantzen, H. M.; Vincent, D.; Li, G.; England, L.; Ramakrishnan, V.; Yang, R. B.; Nurden, P.; Nurden, A.; Julius, D.; Conley, P. B. Identification of the platelet ADP receptor targeted by antithrombotic drugs. Nature 2001, 409, 202-207.
4. Communi, D.; Suarez Gonzalez, N.; Detheux, M.; Brézillon, S.; Lannoy, V.; Parmentier, M.; Boeynaems, J.-M. Identification of a novel human ADP receptor coupled to Gi. J. Biol. Chem. 2001, 276, 41479-41485.
5. 14 receptor. Trends Pharmacol. Sci. 2003, 24, 52-55.
6. Chambers, J. K.; Macdonald, L. E.; Sarau, H. M.; Ames, R. S.; Freeman, K.; Foley, J. J.; Zhu, Y.; McLaughlin, M. M.; Murdock, P.; McMillan, L.; Trill, J.; Swift, A.; Aiyar, N.; Taylor, P.; Vawter, L.; Naheed, S.; Szekeres, P.; Hervieu, G.; Scott, C.; Watson, J. M.; Murphy, A. J.; Duzic, E.; Klein, C.; Bergsma, D. J.; Wilson, S.; Livi, G. P. A G protein-coupled receptor for UDP-glucose. J. Biol. Chem. 2000, 275, 10767-10771.
7. 2+ in human eosinophils: Activation of purinergic P2Y receptors. J. Allergy Clin. Immunol. 2001, 107, 849-855.
8. 1 receptor. Biochem. Biophys. Res. Commun. 1996, 221, 588-593.
9. 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.
10. 1 purinergic receptor in the human brain: Striking neuronal localisation. Comput. Neurol. 2000, 421, 374-384.
11. Franke, H.; Krugel, U.; Schmidt, R.; Grosche, J.; Reichenbach, A.; Illes, P. P2 receptor-types involved in astrogliosis in vivo. Br. J. Pharmacol. 2001, 134, 1180-1189.
12. 12. FEBS Lett. 2002, 513, 179-183.
13. 1 purinergic receptor in Alzheimer's disease. Neuroreport 2000, 11, 3799-3803.
14. Kaiser, R. A.; Buxton, I. L. Nucleotide-mediated relaxation in guinea-pig aorta: Selective inhibition by MRS2179. Br. J. Pharmacol. 2002, 135, 537-545.
15. 1 and P2YT receptors in the morphological changes of platelet aggregation. Thromb. Haemost. 2001, 85, 694-701.
16. Jacobson, K. A. Purine and pyrimidine nucleotide (P2) receptors. Ann. Rep. Med. Chem. 2002, 37, 75-84.
17. 1 receptor antagonists and partial agonists. J. Med. Chem. 1999, 42, 1625-1638.
18. 1 receptor ligands. J. Med. Chem. 2000, 43, 829-842.
19. 1 receptor: Structure activity relationships and receptor docking. J. Med. Chem. 2001, 44, 3092-3108.
20. 1 receptor antagonist. Br. J. Pharmacol. 2002, 135, 2004-2010.
21. 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.
22. Boyer, J. L.; Siddiqi, S.; Fischer, B.; Romera-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.
23. Fischer, B.; Chulkin, A.; Boyer, J. L.; Harden, T. K.; Gendron, F. P.; Beaudoin, A. R.; Chapal, J.; Hillaire-Buys, D.; Petit, P. 2-Thioether 5′-O-(1-thiotriphosphate)adenosine derivatives as new insulin secretagogues acting through P2Y-Receptors. J. Med. Chem. 1999, 42, 3636-3646.
24. 1 purinergic receptor: Synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques. J. Med. Chem. 2002, 45, 962-972.
25. 1-receptor antagonists. J. Org. Chem. 2002, 67, 8063-8071.
26. Ingall, A. H.; Dixon, J.; Bailey, A.; Coombs, M. E.; Cox, D.; McInally, J. I.; Hunt, S. F.; Kindon, N. D.; Theobald, B. J.; Willis, P. A.; Humphries, R. G.; Leff, P.; Clegg, J. A.; Smith, J. A.; Tomlinson, W. Antagonists of the platelet P2T receptor: A novel approach to antithrombotic therapy. J. Med. Chem. 1999, 42, 213-220.
27. Brown, S. G.; King, B. F.; Kim, Y.-C.; Burnstock, G.; Jacobson, K. A. Activity of novel adenine nucleotide derivatives as agonists and antagonists at recombinant rat P2X receptors. Drug Devel. Res. 2000, 49, 253-259.
28. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides? J. Med. Chem. 1996, 39, 3739-3747.
29. Ezzitouni, A.; Russ, P.; Marquez, V. E. (1S,2R)-[(Benzyloxy)-methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4′,1′a-methano and 1′,1′a-methano carbocyclic nucleosides. J. Org. Chem. 1997, 62, 4870-4873.
30. Siddiqui, M. A.; Ford, H., Jr.; George, C.; Marquez, V. E. Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analogue of 2′-deoxyaristeromycin built on a bicyclo[3.1.0]hexane template. Nucleosides Nucleotides 1996, 15, 235-250.
31. 1 receptor with a high affinity radiolabeled antagonist. Mol. Pharmacol. 2002, 62, 1249-1257.
32. Yoshimura, Y.; Moon, H. R.; Choi, Y.; Marquez, V. E. Enantioselective synthesis of bicyclo[3.1.0]hexane carbocyclic nucleosides via a lipase-catalyzed asymmetric acetylation. Characterization of an unusual acetal byproduct. J. Org. Chem. 2002, 67, 5938-5945.
33. Perich, J. W.; Johns, R. B. Di-tert-butyl N, N-diethylphosphoramidite. A new phosphitylating agent for the efficient phosphorylation of alcohols. Synthesis 1988, 2, 142-144.
34. 1 receptor. Tetrahedron 1993, 49, 2169-2184.
35. Wilds, C. J.; Pattanayek, R.; Pan, C.; Wawrzak, Z.; Egli, M. Selenium-assisted nucleic acid crystallography: Use of phosphoroselenoates for MAD phasing of a DNA structure. J. Am. Chem. Soc. 2002, 124, 14910-14916.
36. Robins, M. J.; Uznanski, B. Nucleic acid related compounds. 34. Nonaqueous diazotization of tert-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides. Can. J. Chem. 1981, 59, 2608-2611.
37. 6-methyladenine derivatives as potential adenosine receptor ligand. Arch. Pharm. Res. 2001, 6, 508-513.
38. Coenen, H. H.; Moerlein, S. M.; Stocklin, G. No-Carrier-Added Radiohalogenation Methods with Heavy Halogens. Radiochimica Acta 1983, 34, 47-68.
39. Wilbur, D. S.; Hamlin, D. K.; Srivastava, R. R.; Burns, H. D. Synthesis and radioiodination of N-Boc-p-(tri-butylstannyl)-1-phenylalanine tetrafluorophenyl ester: Preparation of a radiolabeled phenylalanine derivative for peptide synthesis. Bioconjugate Chem. 1993, 4, 574-580.
40. Foged, C.; Halldin, C.; Hiltunen, J.; Braestrup, C.; Thomsen, C.; Hansen, H. C.; Suhara, T.; Pauli, S.; Swahn, C. G.; Karlsson, P.; Larsson, S.; Farde, L. Development of 123I-labeled NNC 13-8241 as a radioligand for SPECT visualization of benzodiazepine receptor binding. Nucl. Med. Biol. 1996, 23, 201-209.
41. Rasmussen, M.; Leonard, N. J. The synthesis of 3-(2′ -Deoxy-D-ribofuranosyl)adenine. Application of a new protecting group, Pivaloyloxymethyl (Pom) J. Am. Chem. Soc. 1967, 89, 9 (21), 5439-5445.
42. Baranowska-Kortylewicz, J.; Helseth, L. D.; Lai, J.; Schneiderman, M. H. ; Schneiderman, G. S.; Dalrymple, G. V. Radiolabeling kit/generator for 5-radiohalogenated uridines Journal of Labeled Compounds and Radiopharceuticals 1994, 34, 513-522.
43. 3-labeled PET tracers Chem. Eur. J. 1997, 3, 2039-2042.
44. Chaconas, G.; v. d. Sande, J. H. 5′-32P labeling of RNA and DNA restriction fragments. Methods Enzymol. 1980, 65, 75-85.
45. Xu, B.; Stephens, A.; Kirschenheuter, G.; Greslin, A. F.; Cheng, X.; Sennelo, J.; Cattaneo, M.; Zighetti, M. L.; Chen, A.; Kim, S. A.; Kim, H. S.; Bischofberger, N.; Cook, G.; Jacobson, K. A. Acyclic analogues of adenosine bisphosphates as P2Y receptor antagonists: Phosphate substitution leads to multiple pathways of inhibition of platelet aggregation. J. Med. Chem. 2002, 45, 5694-5709.
46. Lee, K.; Cass, C.; Jacobson, K. A. Synthesis using ring closure metathesis and effect on nucleoside transport of a (N)-methanocarba S-(4-nitrobenzyl)thioinosine derivative. Org. Lett. 2001, 3, 597-599.
47. 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.
48. 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.