Mutagenesis reveals structure-activity parallels between human A(2A) adenosine receptors and biogenic amine G protein-coupled receptors

Journal of Medicinal Chemistry

Volumn 40, Issue 16, 1997, Pages 2588-2595

  Jiang, Qiaoling ^a   Lee, Brian X ^a   Glashofer, Marc ^a   Van Rhee, A Michiel ^a   Jacobson, Kenneth A ^a,b  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

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

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 (2 CARBOXYETHYL)PHENETHYLAMINO]ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE RECEPTOR; GUANINE NUCLEOTIDE BINDING PROTEIN; RADIOLIGAND; RHODOPSIN;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; GENE EXPRESSION; GENE MUTATION; LIGAND BINDING; MEMBRANE POTENTIAL; PROTEIN ANALYSIS; PROTEIN BINDING; RECEPTOR BINDING; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION;

ADENOSINE; ADENOSINE-5'-(N-ETHYLCARBOXAMIDE); AFFINITY LABELS; ANIMALS; COS CELLS; ENZYME-LINKED IMMUNOSORBENT ASSAY; GTP-BINDING PROTEINS; HUMANS; HYDROGEN-ION CONCENTRATION; IODOBENZENES; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; PHENETHYLAMINES; RATS; RECEPTOR, ADENOSINE A2A; RECEPTORS, BIOGENIC AMINE; RECEPTORS, PURINERGIC P1; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHINES;

EID: 0030796011     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970084v     Document Type: Article

References (50)

1. Fredholm, B. B.; Abbraechio, M. P.; Burnstock, G.; Daly, J. W.; Harden, K. T.; Jacobson, K. A.; Leff, P.; Williams, M. Nomenclature and classification of purinoceptors: a report from the IUPHAR subcommittee. Pharmacol. Rev. 1994, 46, 143-156.
2. Jacobson, K. A.; van Galen, P. J. M.; Williams, M. Adenosine receptors - pharmacology, structure activity relationships, and therapeutic potential. J. Med. Chem. 1992, 35, 407-422.
3. Libert, F.; Parmentier, M.; Lefort, A.; Dinsart, C.; van Sande J.; Maenhaut, C.; Simons, M. J.; Dumont, J. E.; Vassart, G. Selective amplification and cloning of four new members of the G protein-coupled receptor family. Science 1989, 244, 569-572.
4. Jacobson, M. Molecular biology of adenosine receptors. In Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology; Belardinelli, L., Pelleg, A., Eds.; Kluver: Norwell, MA, 1995; pp 5-14.
5. 2a adenosine receptor. J. Biol. Chem. 1995, 270, 13987-13997.
6. 2A adenosine receptors are required for ligand recognition. Mol. Pharmacol. 1996, 50 512-521.
7. 13 in agonist recognition. Eur. J. Pharmacol. 1996, 310, 269-272.
8. 1 adenosine receptor-studies on the ligand binding site by site-directed mutagenesis. J. Biol. Chem. 1992, 267, 10764-10770.
9. 1-adenosine receptor mediates specific agonist binding. J. Biol. Chem. 1994, 269, 2373-2376.
10. 1 adenosine receptors-2 amino-acids are responsible for species-differences in ligand recognition. J. Biol.Chem. 1994, 269, 27900-27906.
11. Olah, M. E.; Jacobson, K. A.; Stiles, G. L. Identification of an adenosine receptor domain specifically involved in binding of 5′-substituted adenosine agonists. J. Biol. Chem. 1994, 269, 18016-18020.
12. 2a adenosine receptors. J. Biol. Chem. 1995, 270, 20485-20490.
13. 2 adenosine receptor binding subunit by photoaffinity crosslinking. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 6572-6576.
14. 2-adenosine receptors. J. Mol. Recognit. 1989, 2, 170-178.
15. 2-adenosine receptors. J. Fluoresc. 1992, 2, 217-223.
16. 2A-adenosine receptor. Mol. Pharmacol. 1994, 45, 871-877.
17. van Rhee, A. M.; Jacobson, K. A. Molecular architecture of G protein-coupled receptors. Drug Dev. Res. 1996, 37, 1-38.
18. 2Y purinoceptor using rhodopsin as template. Drug Des. Discovery 1995, 13, 133-154.
19. Ballesteros, J. A.; Weinstein, H. Integrated methods for the construction of three dimensional models and computational probing of structure-function relations in G-protein coupled receptors. Methods Neurosci. 1995, 25, 366-428.
20. 2 receptors in rat brain. J. Pharmacol. Exp. Ther. 1989, 257, 888-893.
21. 3H]NECA in rat striatal membranes. Mol. Pharmacol. 1986, 29, 331-346.
22. Blüml, K.; Mutschler, E.; Wess, J. Functional role in ligand binding and receptor activation of an asparagine residue present in the sixth transmembrane domain of all muscarinic acetylcholine receptors. J. Biol. Chem. 1994, 269, 18870-18876.
23. 3 receptors. J. Med. Chem. 1996, 39, 2980-2989.
24. Ji, X. D.; Melman, N.; Jacobson, K. A. Interactions of flavonoids and other phytochemicals with adenosine receptors. J. Med. Chem. 1996, 39, 781-788.
25. van Rhee, A. M.; Siddiqi, S. M.; Melman, N.; Shi, D.; Padgett, W. L.; Daly, J. W.; Jacobson, K. A. Tetrahydrobenzothiophenone derivatives as a novel class of adenosine receptor antagonists. J. Med. Chem. 1996, 39, 398-406.
26. 2-adenosine receptors using radioligand binding and photoaffinity labeling. J. Recept. Res. 1992, 12, 149-169.
27. 2a receptor ligand binding site. J. Neurochem. 1994, 63, 1477-1484.
28. 1 receptors in calf brain. Biochem. Pharmacol. 1990, 40, 827-834.
29. Jacobson, K. A.; van Rhee, A. M.; Siddiqi, S. M.; Ji, X. D.; Jiang, Q.; Kim, J.; Kim, H. O. Molecular recognition in adenosine receptors. Perspect. Recept. Res. 1996, 153-164.
30. Fong, T. M.; Yu, H.; Cascieri, M. A.; Underwood, D.; Swain, C. J.; Strader, C. D. The role of histidine 265 in antagonist binding to the neurokinin-1 receptor. J. Biol. Chem. 1994, 269, 2728-2732.
31. Ridge, K. D.; Bhattacharya, S.; Nakayama, T. A.; Khorana, H. G. Light-stable rhodopsin. II. An opsin mutant (Trp265Phe) and a retinal analog with a nonisomerizable 11-cis configuration form a photostable chromophore. J. Biol. Chem. 1992, 267, 6770-6775.
32. Perlman, J. H.; Laakkonen, L.; Osman, R.; Gershengorn, M. C. A model of the thyrotropin-releasing hormone (TRH) receptor binding pocket. Evidence for a second direct interaction between transmembrane helix 3 and TRH. J. Biol. Chem. 1994, 269, 23383-23386.
33. Wang, C. D.; Gallaher, T. K.; Shih, J. C. Site-directed mutagenesis of the serotonin 5-hydroxytrypamine2 receptor: identification of amino acids necessary for ligand binding and receptor activation. Mol. Pharmacol. 1993, 43, 931-940.
34. 1 receptor: roles of aspartic acid107, asparagine198 and threonine194. Biochem. Biophys. Res. Commun. 1994, 203, 1096-1101.
35. Strader, C. D.; Candelore, M. R.; Hill, W. S.; Dixon, R. A.; Sigal, I. S. A single amino acid substitution in the beta-adrenergic receptor promotes partial agonist activity from antagonists. J. Biol. Chem. 1989, 264, 16470-16477.
36. Strader, C. D.; Gaffney, T.; Sugg, E. E.; Candelore, M. R.; Keys, R.; Patchett, A. A.; Dixon, R. A. Allele-specific activation of genetically engineered receptors. J. Biol. Chem. 1991, 266, 5-8.
37. 2 receptor by the substituted-cysteine accessibility method. Neuron 1995, 14, 825-831.
38. 2 dopamine-receptor are important for binding and signal-transduction. J. Neurochem. 1995, 65, 2105-2115.
39. Strader, C. D.; Candelore, M. R.; Hill, W. S.; Sigal, I. S.; Dixon, R. A. Identification of two serine residues involved in agonist activation of the beta-adrenergic receptor. J. Biol. Chem. 1989, 264, 13572-13578.
40. Wess, J.; Gdula, D.; Brann, M. R. Site-directed mutagenesis of the m3 muscarinic receptor: identification of a series of threonine and tyrosine residues involved in agonist but not antagonist binding. EMBO J. 1991, 10, 3729-3734.
41. 2a receptor. Eur. J. Pharmacol. Mol. Pharmacol. Sect. 1994, 268, 95-104.
42. Hibert, M. F.; Trumpp-Kallmeyer, S.; Bruinvels, A. Hoflack, J. Three-dimensional models of neurotransmitter G-binding protein-coupled receptors. Mol. Pharmacol. 1991, 40, 8-15.
43. Nordvall, G.; Hacksell, U. Binding-site modeling of the muscarinic m1 receptor: a combination of homology-based and indirect approaches. J. Med. Chem. 1993, 36, 967-976.
44. van der Wenden, E. M.; Price, S. L.; Apaya, R. P.; Uzerman, A. P.; Soudijn, W. J. Comput.-Aided Mol. Des. 1995, 9, 44-54.
45. 1 adenosine receptor with an antagonist photoaffinity probe. Biochemistry 1996, 50, 789-798.
46. Okayama, H.; Berg, P. A. A cDNA cloning vector that permits expression of cDNA inserts in mammalian cells. Mol. Cell. Biol. 1983, 3, 280-289.
47. Higuchi, R. Using PCR to Engineer DNA. in PCR Technology; Ehrlich, H. A., Ed.; Stockton Press: New York, 1989; pp 61-70.
48. Sanger, R.; Nicklen, S.; Coulson, A. R. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 5463-5467.
49. Cullen, B. R. Use of eukaryotic expression technology in the functional analysis of cloned genes. Methods Enzymol. 1987, 152, 684-704.
50. 50) of an enzyme reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.