Biosensor-based affinities and binding kinetics of small molecule antagonists to the adenosine A2A receptor reconstituted in HDL like particles

FEBS Letters

Volumn 589, Issue 13, 2015, Pages 1399-1405

  Segala, Elena ^a   Errey, James C ^a   Fiez Vandal, Cédric ^a   Zhukov, Andrei ^a   Cooke, Robert M ^a  

^a Heptares Therapeutics Ltd   (United Kingdom)

Author keywords

Abbreviations DDM n dodecyl d maltoside; DM decyl d maltopyranoside; GPCR G protein coupled receptor; NTA nitrilotriacetic acid; PhT phenol triazine; POPC 1 palmitoyl 2 oleoyl sn glycero 3 phosphocholine; POPG 1 palmitoyl 2 oleoyl sn glycero 3 phosphoglycerol; rHDL reconstituted high density lipoprotein; RU resonance unit; SPA scintillation proximity assay; SPR Surface Plasmon Resonance; StaR stabilised receptor; XAC xanthine amine congener

Indexed keywords

4 [2 [7 AMINO 2 (2 FURYL) 1,2,4 TRIAZOLO[2,3 A][1,3,5]TRIAZIN 5 YLAMINO]ETHYL]PHENOL; 5 AMINO 2 (2 FURYL) 7 (2 PHENYLETHYL)PYRAZOLO[4,3 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDINE; 8 CYCLOPENTYL 1,3 DIPROPYLXANTHINE; 8 [4 (2 AMINOETHYLCARBAMOYL)METHOXYPHENYL] 1,3 DIPROPYLXANTHINE; ADENOSINE A2A RECEPTOR; ADENOSINE A2A RECEPTOR ANTAGONIST; G PROTEIN COUPLED RECEPTOR; HIGH DENSITY LIPOPROTEIN; PHENOL TRIAZINE; ROLOFYLLINE; SCH 442416; SLV 320; THEOPHYLLINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG; ADENOSINE A2 RECEPTOR ANTAGONIST; IMMOBILIZED PROTEIN; MOLECULAR LIBRARY; PROTEIN BINDING; RECOMBINANT PROTEIN;

ARTICLE; ASSOCIATION CONSTANT; BINDING AFFINITY; BIOCHIP; BIOSENSOR; CONCENTRATION RESPONSE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG RECEPTOR BINDING; DRUG STRUCTURE; IMMOBILIZATION; INSECT CELL; INTERMETHOD COMPARISON; LIGAND BINDING; MEMBRANE RECONSTITUTION; MOLECULAR WEIGHT; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PURIFICATION; PROTEIN STABILITY; SURFACE PLASMON RESONANCE; THERMOSTABILITY; ANIMAL; ANTAGONISTS AND INHIBITORS; BINDING COMPETITION; GENETIC PROCEDURES; GENETICS; HUMAN; KINETICS; METABOLISM; MOLECULAR LIBRARY; PHARMACOLOGY; PROCEDURES; RADIOASSAY; REPRODUCIBILITY; SF9 CELL LINE; SPODOPTERA;

HEXAPODA;

ADENOSINE A2 RECEPTOR ANTAGONISTS; ANIMALS; BINDING, COMPETITIVE; BIOSENSING TECHNIQUES; HUMANS; IMMOBILIZED PROTEINS; KINETICS; LIPOPROTEINS, HDL; PROTEIN BINDING; RADIOLIGAND ASSAY; RECEPTOR, ADENOSINE A2A; RECEPTORS, G-PROTEIN-COUPLED; RECOMBINANT PROTEINS; REPRODUCIBILITY OF RESULTS; SF9 CELLS; SMALL MOLECULE LIBRARIES; SPODOPTERA; SURFACE PLASMON RESONANCE;

EID: 84929703379     PISSN: 00145793     EISSN: 18733468     Source Type: Journal    
DOI: 10.1016/j.febslet.2015.04.030     Document Type: Article

References (32)

1. M. Rask-Andersen Trends in the exploitation of novel drug targets Nat. Rev. Drug Discov. 10 2010 579 590
2. A.A. Alex, and D.S. Millan Contribution of structure-based drug design to the discovery of marketed drugs RSC Drug Discov. Ser. 13 2012
3. A.S. Doré, K. Okrasa, and J.C. Patel Structure of class C GPCR metabotropic glutamate receptor 5 transmembrane domain Nature 511 2014 557 562
4. A. Srivastava, J. Yano, and Y. Hirozane High-resolution structure of the human GPR40 receptor bound to allosteric agonist TAK-875 Nature 513 2014 124 127
5. H. Wu, C. Wang, and K.J. Gregory Structure of a class C GPCR metabotropic glutamate receptor 1 bound to an allosteric modulator Science 344 2014 58 64
6. N. Robertson, A. Jazayeri, and J. Errey The properties of stabilised G protein-coupled receptors (StaRs) and their use in drug discovery Neuropharmacology 60 2011 36 44
7. 2A receptor J. Med. Chem. 54 2011 4312 4323
8. J.A. Christopher, J. Brown, and A.S. Doré Biophysical fragment screening of the β1-adrenergic receptor: identification of high affinity arylpiperazine leads using structure-based drug design J. Med. Chem. 56 2013 3446 3455
9. T. Aristotelous, S. Ahn, and A.K. Shukla Discovery of β2 adrenergic receptor ligands using biosensor fragment screening of tagged wild-type receptor ACS Med. Chem. Lett. 4 2013 1005 1010
10. T.H. Bayburt, and S.G. Sligar Membrane protein assembly into Nanodiscs FEBS Lett. 584 2010 1721 1727
11. C. Fiez-Vandal, L. Leder, and F. Freuler HDL-like discs for assaying membrane proteins in drug discovery Biophys. Chem. 165-166 2012 56 61
12. A.W. Shaw, V.S. Pureza, and S.G. Sligar The local phospholipid environment modulates the activation of blood clotting J. Biol. Chem. 9 2007 6556 6563
13. J. Borch, F. Torta, and S. Sligar Nanodiscs for immobilization of lipid bilayers and membrane receptors: kinetic analysis of cholera toxin binding to a glycolipid receptor Anal. Chem. 80 2008 6245 6252
14. J.M. Glück, B.W. Koenig, and D. Willbold Nanodiscs allow the use of integral membrane proteins as analytes in surface plasmon resonance studies Anal. Biochem. 408 2011 46 52
15. R.J. Adamson, and A. Watts Kinetics of the early events of GPCR signalling FEBS Lett. 588 2014 4701 4707
16. R.A. Copeland, D.L. Pompliano, and T.D. Meek Drug-target residence time and its implications for lead optimization Nat. Rev. Drug Discov. 5 2006 730 739
17. H. Lu, and P.J. Tonge Drug-target residence time: critical information for lead optimization Curr. Opin. Chem. Biol. 14 2010 467 474
18. 2A antagonist using structure based drug design J. Med. Chem. 55 2012 1898 1903
19. S. Banerjee, T. Huber, and T.P. Sakmar rapid incorporation of functional rhodopsin into nanoscale apolipoprotein bound bilayer (NABB) particles J. Mol. Biol. 377 2008 1067 1081
20. H.J. Motulsky, and L.C. Mahan The kinetics of competitive radioligand binding predicted by the law of mass action Mol. Pharmacol. 25 1984 1 9
21. M.R. Dowling, and S.J. Charlton Quantifying the association and dissociation rates of unlabelled antagonists at the muscarinic M3 receptor Br. J. Pharmacol. 148 2006 927 937
22. 2A receptor define ligand efficacy Mol. Pharmacol. 83 2013 949 958
23. P. Kalk, B. Eggert, and K. Relle The adenosine A1 receptor antagonist SLV320 reduces myocardial fibrosis in rats with 5/6 nephrectomy without affecting blood pressure Br. J. Pharmacol. 151 2007 1025 1032
24. B. Fredholm, A.J. Ijzerman, and K.A. Jacobson International union of pharmacology. XXV. Nomenclature and classification of adenosine receptors Pharmacol. Rev. 53 2001 557-552
25. C. Zocchi, E. Ongini, and S. Ferrara Binding of the radioligand [3H]-SCH 58261, a new non-xanthine A2A adenosine receptor antagonist, to rat striatal membranes Br. J. Pharmacol. 117 1996 1381 1386
26. J.R. Pfister, L. Belardinelli, and G. Lee Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]-xanthine J. Med. Chem. 40 1997 1773 1778
27. 2A receptor ChemMedChem 9 2014 752 761
28. S. Todde, R.M. Moresco, and P. Simonelli Design, radiosynthesis, and biodistribution of a new potent and selective ligand for in vivo imaging of the adenosine A2A receptor system using positron emission tomography J. Med. Chem. 43 4359-4362 2000 27
29. R.L. Rich, J. Errey, and F. Marshall Biacore analysis with stabilized G-protein-coupled receptors Anal. Biochem. 409 2011 267 272
30. V. Früh, Y. Zhou, and D. Chen Application of fragment-based drug discovery to membrane proteins: identification of ligands of the integral membrane enzyme DsbB Chem. Biol. 17 2010 881 891
31. 2 J. Biol. Chem. 284 2009 26732 26741
32. R.A. Cerione Reconstitution of receptor/GTP-binding protein interactions Biochim. Biophys. Acta 1071 1991 473 501