The four cysteine residues in the second extracellular loop of the human adenosine A2B receptor: Role in ligand binding and receptor function

Biochemical Pharmacology

Volumn 82, Issue 4, 2011, Pages 389-399

  Schiedel, Anke C ^a   Hinz, Sonja ^a   Thimm, Dominik ^a   Sherbiny, Farag ^b   Borrmann, Thomas ^a   Maaß, Astrid ^b   Müller, Christa E ^a  

^a UNIVERSITY OF BONN   (Germany)

^b FRAUNHOFER INSTITUTE FOR ALGORITHMS AND SCIENTIFIC COMPUTING SCAI   (Germany)

Author keywords

Adenosine A2B receptor; Disulfide bonds; Extracellular loop 2; Mutagenesis; PSB 603

Indexed keywords

ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE A2B RECEPTOR; CYCLIC AMP; CYSTEINE; CYSTEINE DERIVATIVE; DITHIOTHREITOL;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BIOACCUMULATION; CHO CELL; CONTROLLED STUDY; ENZYME ANALYSIS; ENZYME INACTIVATION; EXTRACELLULAR LOOP 2; FEMALE; HUMAN; LIGAND BINDING; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN STRUCTURE;

ADENOSINE A2 RECEPTOR ANTAGONISTS; ANIMALS; CELLS, CULTURED; CHO CELLS; CRICETINAE; CRICETULUS; CRYSTALLOGRAPHY, X-RAY; CYSTEINE; DISULFIDES; EXTRACELLULAR FLUID; HUMANS; LIGANDS; PROTEIN BINDING; PROTEIN STABILITY; PROTEIN STRUCTURE, SECONDARY; RECEPTOR, ADENOSINE A2B;

EID: 79960373063     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.05.008     Document Type: Article

References (63)

1. G. Burnstock Purine and pyrimidine receptors Cell Mol Life Sci 64 2007 1471 1483 (Pubitemid 46954150)
2. A. Brunschweiger, and C.E. Müller P2 receptors activated by uracil nucleotides - an update Curr Med Chem 13 2006 289 312
3. B.B. Fredholm, A.P. IJzerman, K.A. Jacobson, J. Linden, and C.E. Müller Nomenclature and classification of adenosine receptors - an update Pharmacol Rev 63 2011 1 34
4. G. Schulte, and B.B. Fredholm Signalling from adenosine receptors to mitogen-activated protein kinases Cell Signal 15 2003 813 827 (Pubitemid 36776656)
5. J. Linden, T. Thai, H. Figler, X. Jin, and A.S. Robeva Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells Mol Pharmacol 56 1999 705 713 (Pubitemid 29491171)
6. I. Feoktistov, and I. Biaggioni Adenosine A2B receptors Pharmacol Rev 49 1997 381 402
7. 2b adenosine receptors Br J Pharmacol 122 1997 1075 1082 (Pubitemid 27494221)
8. G. Pearson, F. Robinson, T. Beers Gibson, B.E. Xu, M. Karandikar, and K. Berman Mitogen-activated protein (MAP) kinase pathways: regulation and physiological functions Endocr Rev 22 2001 153 183 (Pubitemid 32458157)
9. 2B adenosine receptor mediates human chorionic vasoconstriction and signals through arachidonic acid cascade Am J Physiol Heart Circ Physiol 288 2005 H2439 H2449
10. C.E. Müller, and K.A. Jacobson Recent developments in adenosine receptor ligands and their potential as novel drugs Biochim Biophys Acta 1808 2010 1290 1308
11. 2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity J Med Chem 52 2009 3994 4006
12. L. Yan, J.C. Burbiel, A. Maass, and C.E. Müller Adenosine receptor agonists: from basic medicinal chemistry to clinical development Expert Opin Emerg Drugs 8 2003 537 576 (Pubitemid 37522665)
13. P.G. Baraldi, M.A. Tabrizi, F. Fruttarolo, R. Romagnoli, and D. Preti Recent improvements in the development of A(2B) adenosine receptor agonists Purinergic Signal 4 2008 287 303 [Epub 2008, April 29]
14. B.B. Fredholm Adenosine, an endogenous distress signal, modulates tissue damage and repair Cell Death Differ 14 2007 1315 1323 (Pubitemid 46965261)
15. 2B receptor in hypoxia FASEB J 20 2006 2242 2250 (Pubitemid 44953854)
16. 2B receptor followed by growth selection in yeast. Identification of constitutively active and gain of function mutations Mol Pharmacol 65 2004 702 710 (Pubitemid 38264038)
17. S. Ryzhov, R. Zaynagetdinov, A.E. Goldstein, S.V. Novitskiy, M.M. Dikov, and M.R. Blackburn Effect of A2B adenosine receptor gene ablation on proinflammatory adenosine signaling in mast cells J Immunol 180 2008 7212 7220
18. M.L. Trincavelli, M. Marroni, D. Tuscano, S. Ceruti, A. Mazzola, and N. Mitro Regulation of A2B adenosine receptor functioning by tumour necrosis factor a in human astroglial cells J Neurochem 91 2004 1180 1190 (Pubitemid 39587456)
19. S. Ryzhov, S.V. Novitskiy, R. Zaynagetdinov, A.E. Goldstein, D.P. Carbone, and I. Biaggioni Host A(2B) adenosine receptors promote carcinoma growth Neoplasia 10 2008 987 995
20. R. Volpini, S. Costanzi, S. Vittori, G. Cristalli, and K.N. Klotz Medicinal chemistry and pharmacology of A2B adenosine receptors Curr Top Med Chem 3 2003 427 443
21. G. Pastorin, S. Federico, S. Paoletta, M. Corradino, F. Cateni, and B. Cacciari Synthesis and pharmacological characterization of a new series of 5,7-disubstituted-[1,2,4]triazolo[1,5-a][1,3,5]triazine derivatives as adenosine receptor antagonists: a preliminary inspection of ligand-receptor recognition process Bioorg Med Chem 18 2010 2524 2536
22. G. Pastorin, T. Da Ros, G. Spalluto, F. Deflorian, S. Moro, and B. Cacciari Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as adenosine receptor antagonists. Influence of the N5 substituent on the affinity at the human A 3 and A 2B adenosine receptor subtypes: a molecular modeling investigation J Med Chem 46 2003 4287 4296 (Pubitemid 37153010)
23. M.W. Beukers, H. den Dulk, E.W. van Tilburg, J. Brouwer, and A.P. IJzerman Why are A(2B) receptors low-affinity adenosine receptors? Mutation of Asn273 to Tyr increases affinity of human A(2B) receptor for 2-(1-Hexynyl)adenosine Mol Pharmacol 58 2000 1349 1356
24. A.L. Matharu, S.J. Mundell, J.L. Benovic, and E. Kelly Rapid agonist-induced desensitization and internalization of the A(2B) adenosine receptor is mediated by a serine residue close to the COOH terminus J Biol Chem 276 2001 30199 30207
25. 2B receptor FASEB J 4 2010 4
26. A.A. Ivanov, V.A. Palyulin, and N.S. Zefirov Computer aided comparative analysis of the binding modes of the adenosine receptor agonists for all known subtypes of adenosine receptors J Mol Graph Model 25 2007 740 754 (Pubitemid 46177687)
27. 2B receptor antagonists J Med Chem 48 2005 6813 6820 (Pubitemid 41533103)
28. 3 receptor subtypes J Med Chem 41 1998 2835 2845 (Pubitemid 28350348)
29. 2A receptor J Comput Aided Mol Des 23 2009 807 828
30. J. Ballesteros, and H. Weinstein Integrated methods for the constructionof three-dimensional models of structure-function relations in G protein-coupled receptors Meth Neurosci 25 1995 366 428
31. C. de Graaf, N. Foata, O. Engkvist, and D. Rognan Molecular modeling of the second extracellular loop of G-protein coupled receptors and its implication on structure-based virtual screening Proteins 71 2008 599 620 (Pubitemid 351430001)
32. V.A. Avlani, K.J. Gregory, C.J. Morton, M.W. Parker, P.M. Sexton, and A. Christopoulos Critical role for the second extracellular loop in the binding of both orthosteric and allosteric G protein-coupled receptor ligands J Biol Chem 282 2007 25677 25686 (Pubitemid 47372845)
33. http://www.ebi.ac.uk/Tools/clustalw2/ (27.01.2011).
34. http://www.ebi.ac.uk/Tools/emboss/align/ (27.01.2011).
35. http://www.cbs.dtu.dk/services/NetNGlyc/ (27.01.2011).
36. http://www.sacs.ucsf.edu/TOPO2/ (27.01.2011).
37. http://modbase.compbio.ucsf.edu/modloop/ (27.01.2011).
38. http://ambermd.org/ (27.01.2011).
39. http://www.ebi.ac.uk/thornton-srv/software/PROCHECK/ (27.01.2011).
40. M.J. Sippl Recognition of errors in three-dimensional structures of proteins Proteins 17 1993 355 362 (Pubitemid 23358545)
41. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the Folin phenol reagent J Biol Chem 193 1951 265 275
42. P. Hillmann, G.Y. Ko, A. Spinrath, A. Raulf, I. von Kügelgen, and S.C. Wolff Key determinants of nucleotide-activated G protein-coupled P2Y(2) receptor function revealed by chemical and pharmacological experiments, mutagenesis and homology modeling J Med Chem 52 2009 2762 2775
43. H.J. Motulsky, and A. Christopoulos Fitting models to biological data using linear and nonlinear regression 2003 GraphPad Software Inc San Diego
44. C. Nordstedt, and B.B. Fredholm A modification of a protein-binding method for rapid quantification of cAMP in cell-culture supernatants and body fluid Anal Biochem 189 1990 231 234 (Pubitemid 20312803)
45. 2A adenosine receptor bound to an antagonist Science 322 2008 1211 1217
46. M.C. Peeters, G.J. van Westen, Q. Li, and A.P. IJzerman Importance of the extracellular loops in G protein-coupled receptors for ligand recognition and receptor activation Trends Pharmacol Sci 32 2011 35 42
47. S.S. Karnik, T.P. Sakmar, H.B. Chen, and H.G. Khorana Cysteine residues 110 and 187 are essential for the formation of correct structure in bovine rhodopsin Proc Natl Acad Sci U S A 85 1988 8459 8463
48. 12 receptor by thiol reagents requires interaction with both extracellular cysteine residues, Cys17 and Cys270 Blood 101 2003 3908 3914 (Pubitemid 36857866)
49. L. Shi, and J.A. Javitch The second extracellular loop of the dopamine D2 receptor lines the binding-site crevice Proc Natl Acad Sci U S A 101 2004 440 445 (Pubitemid 38084655)
50. 3 adenosine receptor to probe interactions between the 2-position of adenosine analogs and Gln167 in the second extracellular loop Nucleosides Nucleotides Nucleic Acids 24 2005 1507 1517 (Pubitemid 41831813)
51. M.P. Bokoch, Y. Zou, S.G. Rasmussen, C.W. Liu, R. Nygaard, and D.M. Rosenbaum Ligand-specific regulation of the extracellular surface of a G-protein-coupled receptor Nature 463 2010 108 112
52. L.S. Ai, and F. Liao Mutating the four extracellular cysteines in the chemokine receptor CCR6 reveals their differing roles in receptor trafficking, ligand binding, and signaling Biochemistry 41 2002 8332 8341 (Pubitemid 34705486)
53. L.W. McGinnes, and T.G. Morrison Disulfide bond formation is a determinant of glycosylation site usage in the hemagglutinin-neuraminidase glycoprotein of Newcastle disease virus J Virol 71 1997 3083 3089 (Pubitemid 27119954)
54. I. Azimi, J.W. Wong, and P.J. Hogg Control of mature protein function by allosteric disulfide bonds Antioxid Redox Signal 14 2011 113 126
55. L.A. Rubenstein, R.J. Zauhar, and R.G. Lanzara Molecular dynamics of a biophysical model for beta2-adrenergic and G protein-coupled receptor activation J Mol Graph Model 25 2006 396 409 (Pubitemid 44667583)
56. R.W. Mercier, Y. Pei, L. Pandarinathan, D.R. Janero, J. Zhang, and A. Makriyannis hCB2 ligand-interaction landscape: cysteine residues critical to biarylpyrazole antagonist binding motif and receptor modulation Chem Biol 17 2010 1132 1142
57. K. Varani, G. Caramori, F. Vincenzi, A. Tosi, A. Barczyk, and M. Contoli Oxidative/nitrosative stress selectively altered A2B adenosine receptors in chronic obstructive pulmonary disease FASEB J 14 2009 14
58. W.A. Goddard 3rd, S.K. Kim, Y. Li, B. Trzaskowski, A.R. Griffith, and R. Abrol Predicted 3D structures for adenosine receptors bound to ligands: comparison to the crystal structure J Struct Biol 170 2010 10 20
59. S. Barrondo, and J. Salles Allosteric modulation of 5-HT(1A) receptors by zinc: binding studies Neuropharmacology 56 2009 455 462 [Epub 2008, October 14]
60. J.A. Schetz, A. Chu, and D.R. Sibley Zinc modulates antagonist interactions with D2-like dopamine receptors through distinct molecular mechanisms J Pharmacol Exp Ther 289 1999 956 964 (Pubitemid 29191254)
61. C.E. Elling, T.M. Frimurer, L.O. Gerlach, R. Jorgensen, B. Holst, and T.W. Schwartz Metal ion site engineering indicates a global toggle switch model for seven-transmembrane receptor activation J Biol Chem 281 2006 17337 17346 [Epub 2006, March 27]
62. J.M. Klco, T.B. Lassere, and T.J. Baranski C5a receptor oligomerization. I. Disulfide trapping reveals oligomers and potential contact surfaces in a G protein-coupled receptor J Biol Chem 278 2003 35345 35353 (Pubitemid 37102303)
63. M. Berthouze, L. Rivail, A. Lucas, M.A. Ayoub, O. Russo, and S. Sicsic Two transmembrane Cys residues are involved in 5-HT4 receptor dimerization Biochem Biophys Res Commun 356 2007 642 647 (Pubitemid 46509766)