Role of extracellular cysteine residues in the adenosine A2A receptor

Purinergic Signalling

Volumn 12, Issue 2, 2016, Pages 313-329

  De Filippo, Elisabetta ^a   Namasivayam, Vigneshwaran ^a   Zappe, Lukas ^a   El Tayeb, Ali ^a   Schiedel, Anke C ^a   Müller, Christa E ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

A2A adenosine receptor; A2B adenosine receptor; Cysteine; Disulfide bonds; GPCR; Mutagenesis

Indexed keywords

ADENOSINE; ADENOSINE A2A RECEPTOR; CYCLIC AMP; CYSTEINE; G PROTEIN COUPLED RECEPTOR; INFLUENZA VIRUS HEMAGGLUTININ;

ALGORITHM; ARTICLE; BINDING COMPETITION; BIOINFORMATICS; CELL DISRUPTION; DISULFIDE BOND; EC50; ENZYME LINKED IMMUNOSORBENT ASSAY; GENE MUTATION; HUMAN; HUMAN CELL; LIGAND BINDING; MOLECULAR DOCKING; MUTAGENESIS; NERVE DEGENERATION; NONHUMAN; POINT MUTATION; POLYMERASE CHAIN REACTION; SEQUENCE ANALYSIS; SITE DIRECTED MUTAGENESIS; STRUCTURE ANALYSIS; VESICULAR STOMATITIS; ANIMAL; CHEMISTRY; CHO CELL LINE; CRICETULUS; EXTRACELLULAR SPACE; METABOLISM; MOLECULAR MODEL;

ANIMALS; CHO CELLS; CRICETULUS; CYSTEINE; EXTRACELLULAR SPACE; HUMANS; MODELS, MOLECULAR; MOLECULAR DOCKING SIMULATION; MUTAGENESIS, SITE-DIRECTED; RECEPTOR, ADENOSINE A2A;

EID: 84960410869     PISSN: 15739538     EISSN: 15739546     Source Type: Journal    
DOI: 10.1007/s11302-016-9506-7     Document Type: Article

References (52)

1. Fredholm BB, IJzerman AP, Jacobson KA, Linden J, Müller CE (2011) International union of basic and clinical pharmacology. LXXXI. Nomenclature and classification of adenosine receptors—an update. Pharmacol Rev 63:1–34
2. Jacobson KA, Müller CE (2015) Medicinal chemistry of adenosine, P2Y and P2X receptors. Neuropharmacology. doi:10.1016/j.neuropharm.2015.12.001
3. Fredholm BB (2007) Adenosine, an endogenous distress signal, modulates tissue damage and repair. Cell Death Differ 14:1315–23
4. Hasko G, Linden J, Cronstein B, Pacher P (2008) Adenosine receptors: therapeutic aspects for inflammatory and immune diseases. Nat Rev Drug Discov 7:759–70
5. Boros D, Thompson J, Larson D (2015) Adenosine regulation of the immune response initiated by ischemia reperfusion injury. Perfusion. doi:10.1177/0267659115586579
6. Eltzschig HK, Carmeliet P (2011) Hypoxia and inflammation. N Engl J Med 364:656–65
7. Eltzschig HK, Sitkovsky M, Robson SC (2012) Purinergic signaling during inflammation. N Engl J Med 367:2322–33
8. Antonioli L, Blandizzi C, Pacher P, Haskó G (2013) Immunity, inflammation and cancer: a leading role for adenosine. Nat Rev Cancer 13:842–57
9. 2AAR antagonists: next generation checkpoint blockade for cancer immunotherapy. Comput Struct Biotechnol J 13:265–72
10. Müller CE, Jacobson KA (1808) Recent developments in adenosine receptor ligands and their potential as novel drugs. Biochim Biophys Acta 2011:1290–308
11. 2B receptor: role in ligand binding and receptor function. Biochem Pharmacol 82:389–99
12. 2A adenosine receptor: identification and characterization of essential amino acid residues. J Biol Chem 285:13032–44
13. 2B adenosine receptor antagonist chemotypes. J Med Chem. doi:10.1021/acs.jmedchem.5b01586
14. Peeters MC, van Westen GJP, Li Q, IJzerman AP (2011) Importance of the extracellular loops in G protein-coupled receptors for ligand recognition and receptor activation. Trends Pharmacol Sci 32:35–42
15. Ni F, So S-P, Cervantes V, Ruan K-H (2008) A profile of the residues in the second extracellular loop that are critical for ligand recognition of human prostacyclin receptor. FEBS J 275:128–37
16. Ott TR, Troskie BE, Roeske RW, Illing N, Flanagan CA, Millar RP (2002) Two mutations in extracellular loop 2 of the human GnRH receptor convert an antagonist to an agonist. Mol Endocrinol 16:1079–88
17. Ahn KH, Bertalovitz AC, Mierke DF, Kendall DA (2009) Dual role of the second extracellular loop of the cannabinoid receptor 1: ligand binding and receptor localization. Mol Pharmacol 76:833–42
18. 3 adenosine receptors. J Biol Chem 269:24692–8
19. 2 adenosine receptors. Biochem Pharmacol 85:1317–29
20. 12 receptor in complex with an antithrombotic drug. Nature 509:115–8
21. Avlani VA, Gregory KJ, Morton CJ, Parker MW, Sexton PM, Christopoulos A (2007) Critical role for the second extracellular loop in the binding of both orthosteric and allosteric G protein-coupled receptor ligands. J Biol Chem 282:25677–86
22. Unal H, Jagannathan R, Bhat MB, Karnik SS (2010) Ligand-specific conformation of extracellular loop 2 in the angiotensin II type 1 receptor. J Biol Chem 285:16341–50
23. Klco JM, Wiegand CB, Narzinski K, Baranski TJ (2005) Essential role for the second extracellular loop in C5a receptor activation. Nat Struct Mol Biol 12:320–6
24. De Graaf C, Foata N, Engkvist O, Rognan D (2008) Molecular modeling of the second extracellular loop of G protein-coupled receptors and its implication on structure-based virtual screening. Proteins 71:599–620
25. 2A adenosine receptor bound to an antagonist. Science 322:1211–7
26. Sherbiny FF, Schiedel AC, Maass A, Müller CE (2009) Homology modelling of the human adenosine A2B receptor based on X-ray structures of bovine rhodopsin, the beta2-adrenergic receptor and the human adenosine A2A receptor. J Comput Aided Mol Des 23:807–28
27. Rader AJ, Anderson G, Isin B, Khorana HG, Bahar I, Klein-Seetharaman J (2004) Identification of core amino acids stabilizing rhodopsin. Proc Natl Acad Sci U S A 101:7246–51
28. Katritch V, Cherezov V, Stevens RC (2013) Structure-function of the G protein-coupled receptor superfamily. Annu Rev Pharmacol Toxicol 53:531–56
29. Ballesteros JA, Weinstein H (1995) Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors. Methods Neurosci 25:366–428
30. Liu W, Chun E, Thompson AA, Chubukov P, Xu F, Katritch V et al (2012) Structural basis for allosteric regulation of GPCRs by sodium ions. Science 337:232–6
31. 2A receptor structures reveal common features of GPCR activation. Nature 474:521–5
32. 2A receptor. Mol Pharmacol 87:907–15
33. Goddard WA, Kim S-K, Li Y, Trzaskowski B, Griffith AR, Abrol R (2010) Predicted 3D structures for adenosine receptors bound to ligands: comparison to the crystal structure. J Struct Biol 170:10–20
34. 12 receptor. Nature 509:119–22
35. 2A receptor: extracellular cysteines influence receptor distribution within the cell and ligand-binding recognition. Biochim Biophys Acta 2015:603–14
36. Markowitz D, Goff S, Bank A (1988) A safe packaging line for gene transfer: separating viral genes on two different plasmids. J Virol 62:1120–4
37. Nordstedt C, Fredholm BB (1990) A modification of a protein-binding method for rapid quantification of cAMP in cell culture supernatants and body fluid. Anal Biochem 189:231–4
38. Backliwal G, Hildinger M, Kuettel I, Delegrange F, Hacker DL, Wurm FM (2008) Valproic acid: a viable alternative to sodium butyrate for enhancing protein expression in mammalian cell cultures. Biotechnol Bioeng 101:182–9
39. Bradford M (1976) Rapid and sensitive method for quantification of microgram quantities of protein utilizing principle of protein-dye binding. Anal Biochem 72:248–54
40. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS et al (2009) AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 30:2785–91
41. Computing GC, Inc. Molecular Operating Environment (MOE) 2014.09 2014.
42. 2 receptor function revealed by chemical and pharmacological experiments, mutagenesis and homology modeling. J Med Chem 52:2762–75
43. 2A adenosine receptors: high-affinity agonist binding to receptor-G protein complexes containing Gβ4. Mol Pharmacol 61:455–62
44. Katritch V, Kufareva I, Abagyan R (2011) Structure based prediction of subtype selectivity for adenosine receptor antagonists. Neuropharmacology 60:108–15
45. 2A receptor in complex with ZM241385 and the xanthines XAC and caffeine. Structure 19:1283–93
46. 2A adenosine receptor. Science 332:322–7
47. Hino T, Arakawa T, Iwanari H, Yurugi-kobayashi T (2012) G protein-coupled receptor inactivation by an allosteric inverse agonist antibody. Nature 482:237–40
48. 2A receptor stability: effects of ligands and disulfide bonds. Biochemistry 49:9181–9
49. 2A adenosine receptors in agonist binding. Biochim Biophys Acta 1324:159–70
50. Müller CE, Scior T (1993) Adenosine receptors and their modulators. Pharm Acta Helv 68:77–111
51. Sabbadin D, Moro S (2014) Supervised molecular dynamics (SuMD) as a helpful tool to depict GPCR-ligand recognition pathway in a nanosecond time scale. J Chem Inf Model 54:372–6
52. 1 adenosine receptor. Biochem Pharmacol 60:1647–54