Hydrophilic side chains in the third and seventh transmembrane helical domains of human A(2A) adenosine receptors are required for ligand recognition

Molecular Pharmacology

Volumn 50, Issue 3, 1996, Pages 512-521

  Jiang, Qiaoling ^a   Van Rhee, A Michiel ^a   Kim, Jeongho ^a   Yehle, Susan ^a   Wess, Jürgen ^a   Jacobson, Kenneth A ^a  

^a 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); 4 [2 [7 AMINO 2 (2 FURYL) 1,2,4 TRIAZOLO[2,3 A][1,3,5]TRIAZIN 5 YLAMINO]ETHYL]PHENOL; 6 N [2 (3,5 DIMETHOXYPHENYL) 2 (2 METHYLPHENYL)ETHYL]ADENOSINE; 9 CHLORO 2 (2 FURYL) 5,6 DIHYDRO 5 IMINO 1,2,4 TRIAZOLO[2,3 C]QUINAZOLINE; ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE A2 RECEPTOR; ROLIPRAM;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROPHILICITY; LIGAND BINDING; NEUROMODULATION; PRIORITY JOURNAL; PROTEIN STRUCTURE; RECEPTOR AFFINITY; RECEPTOR BINDING;

ADENOSINE; ADENYLATE CYCLASE; ALANINE; AMINO ACID SEQUENCE; BASE SEQUENCE; BINDING SITES; BINDING, COMPETITIVE; CYCLIC AMP; GTP-BINDING PROTEINS; HUMANS; KINETICS; LIGANDS; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; OLIGODEOXYRIBONUCLEOTIDES; POINT MUTATION; POLYMERASE CHAIN REACTION; PROTEIN STRUCTURE, SECONDARY; RADIOLIGAND ASSAY; RECEPTOR, ADENOSINE A2A; RECEPTORS, PURINERGIC P1; RECOMBINANT PROTEINS; RIBOSE; SEQUENCE TAGGED SITES; SERINE;

EID: 0029810167     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. Jacobson, K. A., P. J. M. van Galen, and M. Williams. Adenosine receptors: pharmacology, structure activity relationships, and therapeutic potential. J. Med. Chem. 35:407-422 (1992).
2. Libert, F., M. Parmentier, A. Lefort, C. Dinsart, J. van Sande, C. Maenhaut, M. J. Simons, J. E. Dumont, and G. Vassart. Selective amplification and cloning of four new members of the G protein-coupled receptor family. Science (Washington D. C.) 244:569-572 (1989).
3. Jacobson, M. Molecular biology of adenosine receptors, in Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology (L. Belardinelli and A Pelleg, eds.). Kluver, Norwell, MA, 5-14 (1995).
4. Barraco, R. A., K. Martens, M. Parizon, and H. J. Normile. Role of adenosine A2a receptors in the nucleus-accumbens. Prog. Neuropsychopharmacol. Biol. Psychiatry 18:545-553 (1994).
5. Olsson, R. A., and J. D. Pearson. Cardiovascular purinoceptors. Pharmacol. Rev. 3:761-845 (1990).
6. 2 receptors in rat brain. J. Pharmacol. Exp. Ther. 251:888-893 (1989).
7. 2 receptors in the ventral striopallidal system: implications for the treatment of schizophrenia. Neuroscience 63:765-773 (1994).
8. Nikodijevié, O., K. A. Jacobson, and J. W. Daly. Acute treatment of mice with high-doses of caffeine: an animal-model for choreiform movement. Drug Dev. Res. 30:121-128 (1993).
9. Martin, G. E., D. J. Rossi, and M. F. Jarvis. Adenosine agonists reduce conditioned avoidance responding in the rat. Pharm. Biochem. Behav. 45:951-958 (1993).
10. 2 receptor regulation of striatal gene expression, in Adenosine, and Adenine Nucleotides: From Molecular Biology to Integrative Physiology (L. Belardinelli and A. Pelleg, eds.). Kluver, Norwell, MA, 71-76 (1995).
11. Kanda, T., S. Shiozaki, J. Shimada, F. Suzuki, and J. Nakamura. KF1783: a novel selective adenosine A2a receptor antagonist with anticataleptic activity. Eur. J. Pharmacol. 256:263-268 (1994).
12. 2 adenosine receptor binding subunit by photoaffinity crosslinking. Proc. Natl. Acad. Sci. USA 86:6572-6576 (1989).
13. 2-adenosine receptors. J. Mol. Recognit. 2:170-178 (1989).
14. 2-adenosine receptors. J. Fluoresc. 2:217-223 (1992).
15. 2. adenosine receptor. J. Biol. Chem. 270:13987-13997 (1995).
16. 2a. receptor. Eur. J. Pharmacol. 268:95-104 (1994).
17. 1 adenosine receptor: studies on the ligand binding site by site-directed mutagenesis. J. Biol. Chem. 267:10764-10770 (1992).
18. Olah, M. E., K. A. Jacobson, and G. L. Stiles. Identification of an adenosine receptor domain specifically involved in binding of 5′-substituted adenosine agonists. J. Biol. Chem. 269:18016-18020 (1994).
19. Townsend-Nicholson, A., and P. R. Schofield. A threonine residue in the 7th transmembrane domain of the human A1-adenosine receptor mediates specific agonist binding. J. Biol. Chem. 269:2373-2376 (1994).
20. 1 adenosine receptors: 2 amino-acids are responsible for species-differences in ligand recognition. J. Biol. Chem. 269: 27900-27906 (1994).
21. 6-benzyladenosine-5′-uronamides as A3-selective adenosine agonists. J. Med. Chem. 37:636-646 (1994).
22. Okayama, H., and P. A. Berg. A cDNA cloning vector that permits expression of cDNA inserts in mammalian cells. Mol. Cell. Biol. 3:280-289 (1983).
23. Higuchi, R. Using PCR to engineer DNA, in PCR Technology (H. A. Ehrlich, ed.). Stockton Press, New York, 61-70 (1989).
24. Sanger, R., S. Nicklen, and A. R. Coulson. DNA sequencing with chainterminating inhibitors. Proc. Natl. Acad. Sci. USA 74:5463-5467 (1977).
25. Cullen, B. R. Use of eukaryotic expression technology in the functional analysis of cloned genes. Methods Enzymol. 152:684-704 (1987).
26. 2 dopamine receptor negatively coupled with adenylate cyclase in rat anterior pituitary. Mol. Pharmacol. 23:576-584 (1983).
27. 2-dopamine receptor-mediated inhibition of cyclic AMP formation in striatal neurons in primary culture. Mol. Pharmacol. 27:595-599 (1985).
28. 3-adenosine receptors. Drug Dev. Res. 33:51-59 (1994).
29. Baraldi, P. G., S. Manfredini, D. Simoni, L. Zappaterra, C. Zocchi, S. Dionisotti, and E. Ongini. Synthesis of new pyrazolo[4,3-e]1,2,4-triazolo[1,5-c] pyrimidine and 1,2,3-triazolo[4,5-e]1,2,4-triazolo[1,5-c]pyrimidine displaying potent and selective activity as A2a adenosine receptor antagonists. Bioorg. Med. Chem. Lett. 4:2539-2544 (1994).
30. Poucher, S. M., J. R. Keddie, P. Singh, S. M. Stoggall, P. W. R. Caulkett, G. Jones, and M. G. Collis. The in-vitro pharmacology of ZM241385, a potent, nonxanthine, A2a selective adenosine receptor antagonist. Br. J. Pharmacol. 115:1096-1102 (1995).
31. van Rhee, A. M., S. M. Siddiqi, N. Melman, D. Shi, W. L. Padgett, J. W. Daly, and K. A. Jacobson. Tetrahydrobenzothiophenone derivatives as a novel class of adenosine receptor antagonists. J. Med. Chem. 39:398-406 (1996).
32. 1b-adrenergic receptor by all amino acid substitution at a single site. J. Biol. Chem. 267:1430-1433 (1992).
33. 2-adrenergic receptor. J. Biol. Chem. 268:16483-16487 (1993).
34. 2 receptors: structure-function relationships. Med. Res. Rev. 12:423-471 (1992).
35. 2a-adenosine receptors. Mol. Pharmacol. 42:123-133 (1992).
36. Hubbard, S. J., S. F. Campbell, and J. M. Thornton. Molecular recognition: conformational analysis of limited proteolysis sites and serine protease inhibitors. J. Mol. Biol. 220:507-530 (1991).
37. 1 receptor liganda: a test case for Distributed Multipole Analysis in medicinal chemistry. J. Comput. Aided Mol. Design 9:44-54 (1995).
38. Strader, C. D., I. S. Sigal, M. R. Candelore, E. Rands, W. S. Hill, and R. A. Dixon. Conserved aspartic acid residues 79 and 113 of the β-adrenergic receptor have different roles in receptor function. J. Biol. Chem. 263: 10267-10271 (1988).
39. Strader, C. D., T. Gaffney, E. E. Sugg, M. R. Candelore, R. Keys, A. A. Patchett, and R. A. Dixon. Allele-specific activation of genetically engineered receptors. J. Biol. Chem. 266:5-8 (1991).
40. 2 receptor. Eur. J. Pharmacol. 227:205-214 (1992).
41. 2 receptor by the substituted-cysteine accessibility method. Neuron 14:825-831 (1995).
42. 2 receptor. J. Biol. Chem. 267:20840-20843 (1992).
43. 1A receptor: a site-directed mutation study. FEBS Lett. 312:259-262 (1992).
44. Wang, C. D., T. K. Gallaher, and J. C. Shih. Site-directed mutageneeis of the serotonin 5-hydroxytrypamine2 receptor: identification of amino acids necessary for ligand binding and receptor activation. Mol. Pharmacol. 43:931-940 (1993).
45. Fraser, C. M., C. D. Wang, D. A. Robinson, J. D. Gocayne, and J. C. Venter. Site-directed mutagenesis of ml muscarinic acetylcholine receptors: conserved aspartic acids play important roles in receptor function. Mol. Pharmacol. 36:840-847 (1989).
46. Kurtenbach, E., C. A. Curtis, E. K. Pedder, A. Aitken, A. C. Harris, and E. C. Hulme. Muscarinic acetylcholine receptors: peptide sequencing identifies residues involved in antagonist binding and disulfide bond formation. J. Biol. Chem. 265:13702-13708 (1990).
47. Vassart, G., J. Parma, J. Van Sande, and J. E. Dumont. The thyrotropin receptor and the regulation of thyrocyte function and growth: update 1994, in Endocrine Reviews Monographs 3. Clinical and Molecular Aspects of Diseases of the Thyroid (L. E. Braverman and S. Refetoff, eds.). The Endocrine Society Press, Bethesda, MD, 77-80 (1994).
48. Fong, T. M., H. Yu, and C. D. Strader. Molecular basis for the species selectivity of the neurokinin-1 receptor antagonists CP-96,345 and RP67580. J. Biol. Chem. 267:25668-25671 (1992).
49. Zvyaga, T. A., K. C. Min, M. Beck, and T. P. Sakmar. Movement of the retinylidene Schiff base counterion in rhodopsin by one helix turn reverses the pH dependence of the metarhodopsin I to metarhodopsin II transition. J. Biol. Chem. 268:4661-4667 (1993).
50. Strader, C. D., M. R. Candelore, W. S. Hill, I. S. Sigal, and R. A. F. Dixon. Identification of two serine residues involved in agonist activation of the β-adrenergic receptor. J. Biol. Chem. 264:13572-13578 (1989).
51. Savarese, T. M., C.-D. Wang, and C. M. Fraser. Site-directed mutagenesis of the rat m1 muscarinic receptor: role of conserved cysteines in receptor function. J. Biol. Chem. 267:11439-11448 (1992).
52. Latronico, A. C., J. Anasti, I. J. P. Arnhold, R. Rapaport, B. B. Mendonca, W. Bloise, M. Castro, C. Tsigos, and G. P. Chrousos. Testicular and ovarian resistance to luteinizing-hormone caused by inactivating mutations of the luteinizing hormone-receptor gene. N. Engl. J. Med. 334:507-512 (1996).