Molecular recognition in purinergic receptors. 2. Diastereoselectivity of the h-P2Y1-receptor

Journal of Medicinal Chemistry

Volumn 47, Issue 18, 2004, Pages 4405-4416

  Major, Dan T ^a   Nahum, Victoria ^a   Wang, Yingfei ^b   Reiser, Georg ^b   Fischer, Bilha ^a  

^a BAR ILAN UNIVERSITY   (Israel)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE DERIVATIVE; ASPARTIC ACID; COORDINATION COMPOUND; MAGNESIUM ION; NUCLEOTIDE DERIVATIVE; PHOSPHATE; PURINE P2Y1 RECEPTOR; PURINE RECEPTOR;

ARTICLE; BINDING AFFINITY; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHIRALITY; COMPLEX FORMATION; COMPUTER ANALYSIS; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DIASTEREOISOMER; ELECTRONICS; MOLECULAR MECHANICS; MOLECULAR MODEL; MOLECULAR RECOGNITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTEIN CONFORMATION; PROTEIN PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ADENOSINE TRIPHOSPHATE; BINDING SITES; CALCIUM SIGNALING; CELL LINE; COMPUTER SIMULATION; HUMANS; LIGANDS; MAGNESIUM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PROTEIN BINDING; RECEPTORS, PURINERGIC P2; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4143056857     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049771u     Document Type: Article

References (55)

1. (a) Fischer, B. Therapeutic Applications of ATP-(P2)-Receptors Agonists and Antagonists. Exp. Opin. Therap. Pat. 1999, 9, 385-399.
2. (b) Guile, S. D.; Ince, F.; Ingall, A. H.; Kindon, N. D.; Meghani, P.; Mortimore, M. P. The Medicinal Chemistry of the P2 Receptor Family. Prog. Med. Chem. 2001, 38, 115-187.
3. 1-Receptor. 1. A Synthetic, Biochemical, and NMR Approach. J. Med. Chem. 1999, 42, 5325-5337.
4. 1-Receptor. 2. A Computational Approach. J. Med. Chem. 1999, 42, 5338-5347.
5. 15N NMR. J. Org. Chem. 2002, 67, 790-802.
6. (a) Jacobson, K. A.; Jarvis, M. F.; Williams, M.Purine and Pyrimidine (P2) Receptors as Drug Targets J. Med. Chem. 2002, 45, 4057-4093.
7. (b) van Rhee, A. M.; Fischer, B.; van Galen, P. J. M.; Jacobson, K. A. Modelling the P2Y Purinoceptor Using Rhodopsin As Template. Drug Des. Discovery 1995, 13, 133-154.
8. (c) Moro, S.; Guo, D.; Camaioni, E.; Boyer, J. L.; Harden, T. K.; Jacobson, K. A Human P2Y(1) Receptor: Molecular Modeling and Site-Directed Mutagenesis as Tools to Identify Agonist and Antagonist Rrecognition Sites. J. Med. Chem. 1998, 41, 1456-1466.
9. (d) Moro, S.; Hoffmann, C.; Jacobson, K. A. Role of the Extracellular Loops of G Protein-Coupled Receptors in Ligand Recognition: A Molecular Modeling Study of the Human P2Y(1) Receptor. Biochemistry 1999, 38, 3498-3509.
10. (e) Kim, H. O.; Barak, D.; Harden, T. K.; Boyer, J. L.; Jacobson, K. A. Acyclic and Cyclopropyl Analogues of Adenosine Bisphosphate Antagonists of the P2Y(1) Receptor: Structure-Activity Relationships and Receptor Docking. J. Med. Chem. 2001, 44, 3092-3108.
11. 1 Receptor Agonists. J. Med. Chem. 2002, 45, 5384-5396.
12. 1-Receptor. J. Med. Chem. 2004, 47, 4391-4404.
13. (a) Eckstein, F. Nucleoside Phosphorothioates. Annu. Rev. Biochem. 1985, 54, 367-402.
14. (b) Garcia, G. A.; Leatherbarrow, R. J.; Eckstein, F.; Fersht, A. R. Metal-Ion Dependence of Phosphorothioate ATP Analogues in the Bacillus-Stearothermophilus Tyrosyl-Transfer RNA-Synthetase Reaction. Biochemistry 1990, 29, 1643-1648.
15. 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.
16. 2 Receptors Induced by Novel Adenosine 5′-O-(1-boranotriphosphate) Derivatives. Br. J. Pharmacol. 2004, 142, 869-878.
17. Saenger W. In Principles of nucleic acid structure; Springer-Verlag: New York, 1984; pp 81-82.
18. Donohue, J.; Trueblood, K. N. Base Pairing in DNA. J. Mol. Biol. 1960, 2, 363-371.
19. Sundaralingam, M. Stereochemistry of Nucleic Acids and their Constituents. IV. Allowed and Preferred Conformations of Nucleosides, Nucleoside Mono-, Di-, Tri-, Tetraphosphates, Nucleic Acids, and Polynucleotides. Biopolymers 1969, 7, 821-860.
20. Ippel, J. H.; Wijmenga, S. S.; de Jong, R.; Heus, H. A.; Hilbers, C. W. Heteronuclear Scalar Coupling in the Bases and Sugar Rings of Nucleic Acids: Their Determination and Application in Assignment and Conformational Analysis. Magn. Reson. Chem. 1996, 34, S156-S176.
21. Davies, D. B.; Danyluk, S. S. Nuclear Magnetic Resonance Studies of 5′-Ribo- and Deoxyribonucleotide Structures in Solution. Biochemistry 1974, 13, 4417-4434.
22. (a) Altona, C.; and Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. New Description Using the Concept of Pseudorotation. J. Am. Chem. Soc. 1972, 94, 8205-8212.
23. (b) Altona, C.; Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. Improved Method for the Interpretation of Proton Magnetic Resonance Coupling Constants. J. Am. Chem. Soc. 1973, 95, 2333-2344.
24. Davies, D. B.; Danyluk, S. S. International Symposiuym on NMR Spectroscopy, University of Surrey, 1972.
25. Blackburn, B. J.; Grey, A. A.; Smith, I. C. P.; Hruska, F. E. Determination of the Molecular Conformation of Uridine in Aqueous Solution by Proton Magnetic Resonance Spectroscopy. Comparison with β-Pseudouridine. Can. J. Chem. 1970, 48, 2866-2870.
26. Hruska, F. E. In Conformations of Biological Molecules and Polymers (Proceedings of Jerusalem Symposium); Bergmann, E. D., Pullman, B., Eds.; Israel Academy of Science and Humanities: Jerusalem, 1973; p 345.
27. Nahum, V. and Fischer, B. Eur J. Inorg. Chem. 2004, in press.
28. Fujii, A.; Patwari, G. N.; Ebata, T.; Mikami, N. Vibrational Spectroscopic Evidence of Unconventional Hydrogen Bonds. Int. J. Mass Spect. 2002, 220, 289-312.
29. Srivastava, P. C.; Robins, R. K.; Meyer, R. B., Jr. In Chemistry of nucleosides and nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988; Vol. 1, pp 197-198.
30. Platts, J. A.; Howard, S. T.; Bracke, B. R. F. Directionality of Hydrogen Bonds to Sulfur and Oxygen. J. Am. Chem. Soc. 1996, 118, 2726-2733.
31. Meyer, P.; Schneider, B.; Sarfati, S.; Deville-Bonne, D.; Guerreiro, C.; Boretto, J.; Canard, B. Structural Basis for Activation of α- Boranophosphate Nucleotide Analogues Targeting Drug-resistant Reverse Transcriptase. EMBO J. 2069, 19, 3520-3529.
32. Jaffe, E. K.; Cohn M. Divalent Cation-Dependent Stereospecifity of Adenosine 5′-O-(2-thiotriphosphate) in the Hexokinase and Pyrivate Kinase Reactions. The Absolute Stereochemistry of the Diastereoisomers of Adenosine 5′-O-(2-thiotriphosphate). J. Biol. Chem. 1978, 253, 4823-4825.
33. 2+ Binding. J. Biol. Chem. 1978, 17, 652-657.
34. 32P-labled Phosphorothioate analogues of ATP. J. Biol. Chem. 1981, 256, 7322-7328.
35. Lippard, S. J.; Berg, J. M. In Principles of Bioinorganic Chemistry, University Science Books: Mill Valley, CA, 1994; pp 64-66, 132-133, 276-277.
36. Klevickis & Grisham In Metal ion in biological systems; Sigel, A., Sigel, H., Eds.; Marcel Dekker: New York, 1996; Vol. 32.
37. (a) Lane, M.; Boatman, D. E.; Albrecht, R. M.; Bavister, B. D. Intracellular Divalent Cation Homeostasis and Developmental Competence in the Hamster Preimplantation Embryo. Mol. Reprod. Dev. 1998, 50, 443-50.
38. (b) Touyz, R. M.; Yao, G. Modulation of Vascular Smooth Muscle Cell Growth by Magnesium-role of Mitogen-Activated Protein Kinases. J. Cell Physiol. 2003, 197, 326-335.
39. (c) Grubbs, R. D. Intracellular Magnesium and Magnesium Buffering. BioMetals 2002, 15, 251-259.
40. Cohn, M. In Biological actions of extracellular ATP; Dubyak, G. R., Fedan, J. S., Eds.; Annals of the New York Academy of Sciences, Vol. 603; The New York Academy of Sciences: New York, 1990.
41. -32P] diphosphate: Synthesis and Use as Probe of Platelet ADP Receptors. Methods Enzymol. 1992, 215, 137-142.
42. (a) Kikugawa, K.; Suehiro, H.; Inchino, M. Platelet Aggregation Inhibitors. 6. 2-Thioadenosine Derivatives. J. Med. Chem. 1973, 16, 1381-1388.
43. (b) 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.
44. 1 Receptor Tagged with Green-Fluorescent Protein: High-Affinity Ligand Recognition of Adenosine Diphosphates and Triphosphates and Selectivity Identical to that of the Wild-Type Receptor. Biochem. Pharmacol. 2000, 59, 791-800.
45. 1, Receptor Isolation. Biochem. Pharmacol. 2001, 61, 1259-1269.
46. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. CHARMM. A program for macromolecular energy, minimization, and dynamics calculations. J. Comput. Chem. 1983, 4, 187-217.
47. Foloppe, N.; MacKerell, A. D., Jr. All-atom empirical force field for nucleic acids: I. Parameter optimization based on small molecule and condensed phase macromolecular target data. J. Comput. Chem. 2000, 21, 86-104.
48. Pavelites, J. J.; Gao, J.; Bash, P. A.; Mackerell, A. D., Jr. A molecular mechanics force field for NAD(+), NADH, and the pyrophosphate groups of nucleotides. J. Comput. Chem. 1997, 18, 221-239.
49. Otkidach, D. S.; Pletnev, I. V. Conformational analysis of boron-containing compounds using Gillespie-Kepert version of molecular mechanics. J. Mol. Struct. (THEOCHEM) 2001,536,65-72.
50. Møller, C.; Plesset, M. S. Note on an approximate treatment for many-electron systems. Phys. Rev. 1934, 46, 618-622.
51. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of simple potential functions for simulating liquid water. J. Chem. Phys. 1983, 79, 926-935.
52. (a) Hall, G. G. The molecular orbital theory of chemical valency VIII. A method for calculating ionisation potentials. Proc. R. Soc. London Ser. A 1951, 205, 541-552.
53. (b) Roothan C. C. J. New developments in molecular orbital theory. Rev. Mod. Phys. 1951, 23, 69-89.
54. Steinbach, P. J.; Brooks, B. R. New spherical-cutoff methods for long-range forces in macromolecular simulation. J. Comput. Chem. 1994, 15, 667-683.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 (Revision A.7); Gaussian, Inc., Pittsburgh, PA, 1998.