Selective fluorescent nonpeptidic antagonists for vasopressin V2 GPCR: Application to ligand screening and oligomerization assays.

Journal of Medicinal Chemistry

Volumn 55, Issue 20, 2012, Pages 8588-8602

  Loison, Stéphanie ^a   Cottet, Martin ^b   Orcel, Hélène ^b   Adihou, Hélène ^a   Rahmeh, Rita ^b   Lamarque, Laurent ^c   Trinquet, Eric ^c   Kellenberger, Esther ^a   Hibert, Marcel ^a   Durroux, Thierry ^b   Mouillac, Bernard ^b   Bonnet, Dominique ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSTITUT DE GÉNOMIQUE FONCTIONNELLE   (France)

^c Parc Marcel Boiteux ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID; PIPERAZINE; PURINERGIC P2Y RECEPTOR ANTAGONIST; PURINERGIC P2Y12 RECEPTOR;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG IDENTIFICATION; IC 50; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION; THROMBOCYTE RICH PLASMA;

BENZAZEPINES; CLICK CHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; HIGH-THROUGHPUT SCREENING ASSAYS; LIGANDS; MODELS, MOLECULAR; PROTEIN MULTIMERIZATION; RECEPTORS, OXYTOCIN; RECEPTORS, VASOPRESSIN; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867753791     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3006146     Document Type: Article

References (49)

1. Thomsen, W.; Frazer, J.; Unett, D. Functional assays for screening GPCR targets Curr. Opin. Biotechnol. 2005, 16 (6) 655-665
2. Drews, J. Drug discovery: a historical perspective Science 2000, 287 (5460) 1960-1964
3. Ma, P.; Zemmel, R. Value of novelty? Nature Rev. Drug Discovery 2002, 1 (8) 571-572
4. Hovius, R.; Vallotton, P.; Wohland, T.; Vogel, H. Fluorescence techniques: shedding light on ligand-receptor interactions Trends Pharmacol. Sci. 2000, 21 (7) 266-273
5. Owicki, J. C. Fluorescence polarization and anisotropy in high throughput screening: perspectives and primer J. Biomol. Screening 2000, 5 (5) 297-306
6. Allen, M.; Reeves, J.; Mellor, G. High throughput fluorescence polarization: a homogeneous alternative to radioligand binding for cell surface receptors J. Biomol. Screening 2000, 5 (2) 63-69
7. Albizu, L.; Teppaz, G.; Seyer, R.; Bazin, H.; Ansanay, H.; Manning, M.; Mouillac, B.; Durroux, T. Toward efficient drug screening by homogeneous assays based on the development of new fluorescent vasopressin and oxytocin receptor ligands J. Med. Chem. 2007, 50 (20) 4976-4985
8. Tahtaoui, C.; Parrot, I.; Klotz, P.; Guillier, F.; Galzi, J. L.; Hibert, M.; Ilien, B. Fluorescent pirenzepine derivatives as potential bitopic ligands of the human M1 muscarinic receptor J. Med. Chem. 2004, 47 (17) 4300-4315
9. Szollosi, J.; Damjanovich, S.; Matyus, L. Application of fluorescence resonance energy transfer in the clinical laboratory: routine and research Cytometry 1998, 34 (4) 159-179
10. Daval, S. B.; Valant, C.; Bonnet, D.; Kellenberger, E.; Hibert, M.; Galzi, J. L.; Ilien, B. Fluorescent Derivatives of AC-42 To Probe Bitopic Orthosteric/Allosteric Binding Mechanisms on Muscarinic M1 Receptors J. Med. Chem. 2012, 55 (5) 2125-2143
11. Marie, J.; Leyris, J. P.; Roux, T.; Trinquet, E.; Verdie, P.; Fehrentz, J. A.; Oueslati, N.; Douzon, S.; Bourrier, E.; Lamarque, L.; Gagne, D.; Galleyrand, J. C.; Mkadmi, C.; Martinez, J.; Mary, S.; Baneres, J. L. Homogeneous time-resolved fluorescence-based assay to screen for ligands targeting the growth hormone secretagogue receptor type 1a Anal. Biochem. 2011, 408 (2) 253-262
12. Degorce, F.; Card, A.; Soh, S.; Trinquet, E.; Knapik, G. P.; Xie, B. HTRF: A technology Tailored for Drug Discovery-A review of Theoretical Aspects and Recent Applications Curr. Chem. Genomics 2009, 3, 22-32
13. Pin, J. P.; Maurel, D.; Comps-Agrar, L.; Brock, C.; Rives, M. L.; Bourrier, E.; Ayoub, M. A.; Bazin, H.; Tinel, N.; Durroux, T.; Prezeau, L.; Trinquet, E. Cell-surface protein-protein interaction analysis with time-resolved FRET and snap-tag technologies: application to GPCR oligomerization Nature Methods 2008, 5 (6) 561-567
14. Albizu, L.; Cottet, M.; Kralikova, M.; Stoev, S.; Seyer, R.; Brabet, I.; Roux, T.; Bazin, H.; Bourrier, E.; Lamarque, L.; Breton, C.; Rives, M. L.; Newman, A.; Javitch, J.; Trinquet, E.; Manning, M.; Pin, J. P.; Mouillac, B.; Durroux, T. Time-resolved FRET between GPCR ligands reveals oligomers in native tissues Nature Chem. Biol. 2010, 6 (8) 587-594
15. Middleton, R. J.; Kellam, B. Fluorophore-tagged GPCR ligands Curr. Opin. Chem. Biol. 2005, 9 (5) 517-525
16. Robertson, G. L. Vaptans for the treatment of hyponatremia Nature Rev. Endocrinol. 2011, 7 (3) 151-161
17. Arai, Y.; Fujimori, A.; Sudoh, K.; Sasamata, M. Vasopressin receptor antagonists: potential indications and clinical results Curr. Opin. Pharmacol. 2007, 7 (2) 124-129
18. Jean-Alphonse, F.; Perkovska, S.; Frantz, M. C.; Durroux, T.; Mejean, C.; Morin, D.; Loison, S.; Bonnet, D.; Hibert, M.; Mouillac, B.; Mendre, C. Biased Agonist Pharmacochaperones of the AVP V2 Receptor May Treat Congenital Nephrogenic Diabetes Insipidus J. Am. Soc. Nephrol. 2009, 20 (10) 2190-2203
19. Manning, M.; Misicka, A.; Olma, A.; Bankowski, K.; Stoev, S.; Chini, B.; Durroux, T.; Mouillac, B.; Corbani, M.; Guillon, G. Oxytocin and Vasopressin Agonists and Antagonists as Research Tools and Potential Therapeutics J. Neuroendocrinol. 2012, 24 (4) 609-628
20. Mouillac, B.; Manning, M.; Durroux, T. Fluorescent agonists and antagonists for vasopressin/oxytocin G protein-coupled receptors: usefulness in ligand screening assays and receptor studies Mini-Rev. Med. Chem. 2008, 8 (10) 996-1005
21. Durroux, T.; Peter, M.; Turcatti, G.; Chollet, A.; Balestre, M. N.; Barberis, C.; Seyer, R. Fluorescent pseudo-peptide linear vasopressin antagonists: design, synthesis, and applications J. Med. Chem. 1999, 42 (7) 1312-1319
22. Bonnet, D.; Riche, S.; Loison, S.; Dagher, R.; Frantz, M. C.; Boudier, L.; Rahmeh, R.; Mouillac, B.; Haiech, J.; Hibert, M. Solid-phase organic tagging resins for labeling biomolecules by 1,3-dipolar cycloaddition: application to the synthesis of a fluorescent non-peptidic vasopressin receptor ligand Chem.-Eur. J. 2008, 14 (20) 6247-6254
23. Ogawa, H.; Yamashita, H.; Kondo, K.; Yamamura, Y.; Miyamoto, H.; Kan, K.; Kitano, K.; Tanaka, M.; Nakaya, K.; Nakamura, S.; Mori, T.; Tominaga, M.; Yabuuchi, Y. Orally active, nonpeptide vasopressin V2 receptor antagonists: a novel series of 1-[4-(benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1 H -benzazepines and related compounds J. Med. Chem. 1996, 39 (18) 3547-3555
24. Matsuhisa, A.; Tanaka, A.; Kikuchi, K.; Shimada, Y.; Yatsu, T.; Yanagisawa, I. Nonpeptide arginine vasopressin antagonists for both V1A and V2 receptors: synthesis and pharmacological properties of 2-phenyl-4′-[(2,3, 4,5-tetrahydro-1 H -1-benzazepin-1-yl)carbonyl]benzanilide derivatives Chem. Pharm. Bull. (Tokyo) 1997, 45 (11) 1870-1874
25. Rzepecki, P.; Geib, N.; Peifer, M.; Biesemeier, F.; Schrader, T. Synthesis and binding studies of Alzheimer ligands on solid support J. Org. Chem. 2007, 72 (10) 3614-3624
26. Wermuth, C. G. Preparation of Water-Soluble Compounds by Covalent Attachment of Solubilizing Moieties. In The Practice of Medicinal Chemistry, 2nd ed.; Wermuth, C. G., Eds.; Elsevier Academic Press: New York, 2003; pp 626-627.
27. Jia, J.; Wang, K.; Shi, W.; Chen, S. M.; Li, X. H.; Ma, H. M. Rhodamine B Piperazinoacetohydrazine: A Water-Soluble Spectroscopic Reagent for Pyruvic Acid Labeling Chem.-Eur. J. 2010, 16 (22) 6638-6643
28. Bai, M.; Wyatt, S. K.; Han, Z.; Papadopoulos, V.; Bornhop, D. J. A novel conjugable translocator protein ligand labeled with a fluorescence dye for in vitro imaging Bioconjuate Chem. 2007, 18 (4) 1118-1122
29. Glunde, K.; Foss, C. A.; Takagi, T.; Wildes, F.; Bhujwalla, Z. M. Synthesis of 6′- O -lissamine-rhodamine B-glucosamine as a novel probe for fluorescence imaging of lysosomes in breast tumors Bioconjuate Chem. 2005, 16 (4) 843-851
30. Bonnet, D.; Ilien, B.; Galzi, J. L.; Riche, S.; Antheaune, C.; Hibert, M. A rapid and versatile method to label receptor ligands using "click" chemistry: Validation with the muscarinic M1 antagonist pirenzepine Bioconjuate Chem. 2006, 17 (6) 1618-1623
31. Xu, J. D.; Corneillie, T. M.; Moore, E. G.; Law, G. L.; Butlin, N. G.; Raymond, K. N. Octadentate Cages of Tb(III) 2-Hydroxyisophthalamides: A New Standard for Luminescent Lanthanide Labels J. Am. Chem. Soc. 2011, 133 (49) 19900-19910
32. Ghose, S.; Trinquet, E.; Laget, M.; Bazin, H.; Mathis, G. Rare earth cryptates for the investigation of molecular interactions in vitro and in living cells J. Alloys Compd. 2008, 451 (1-2) 35-37
33. Boeglin, D.; Bonnet, D.; Hibert, M. Solid-phase preparation of a pilot library derived from the 2,3,4,5-tetrahydro-1 H -benzo[ b ]azepin-5-amine scaffold J. Comb. Chem. 2007, 9 (3) 487-500
34. Coste, J.; Le-Nguyen, D.; Castro, B. PyBOP: a new peptide coupling reagent devoid of toxic by-product Tetrahedron Lett. 1990, 31 (2) 205-208
35. Zhang, A. J.; Russell, D. H.; Zhu, J.; Burgess, K. A method for removal of N-BOC protecting groups from substrates on TFA-sensitive resins Tetrahedron Lett. 1998, 39, 7439-7442
36. Corrie, J. E. T.; Davis, C. T.; Eccleston, J. F. Chemistry of sulforhodamine-amine conjugates Bioconjugate Chem. 2001, 12 (2) 186-194
37. Yang, H.; Vasudevan, S.; Oriakhi, C. O.; Shields, J.; Carter, R. G. Scalable synthesis of lissamine rhodamine B sulfonyl chloride and incorporation of xanthene derivatives onto polymer supports Synthesis (Stuttgart) 2008, 6) 957-961
38. Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Reactions of Peptide Bond 0.4. Benzotriazonyl- N -Oxytridimelthylamino Phosphonium Hexafluorophosphate (BOP) Tetrahedron Lett. 1975, 14) 1219-1222
39. Breton, C.; Chellil, H.; Kabbaj-Benmansour, M.; Carnazzi, E.; Seyer, R.; Phalipou, S.; Morin, D.; Durroux, T.; Zingg, H.; Barberis, C.; Mouillac, B. Direct identification of human oxytocin receptor-binding domains using a photoactivatable cyclic peptide antagonist: comparison with the human V1a vasopressin receptor J. Biol. Chem. 2001, 276 (29) 26931-26941
40. Jacobson, K. A. Functionalized Congener Approach to the Design of Ligands for G Protein-Coupled Receptors (GPCRs) Bioconjugate Chem. 2009, 20 (10) 1816-1835
41. Karton, Y.; Baumgold, J.; Handen, J. S.; Jacobson, K. A. Molecular Probes for Muscarinic Receptors-Derivatives of the M1-Antagonist Telenzepine Bioconjugate Chem. 1992, 3 (3) 234-240
42. Kruse, A. C.; Hu, J. X.; Pan, A. C.; Arlow, D. H.; Rosenbaum, D. M.; Rosemond, E.; Green, H. F.; Liu, T.; Chae, P. S.; Dror, R. O.; Shaw, D. E.; Weis, W. I.; Wess, J.; Kobilka, B. K. Structure and dynamics of the M3 muscarinic acetylcholine receptor Nature 2012, 482 (7386) 552-556
43. Wu, B. L.; Chien, E. Y. T.; Mol, C. D.; Fenalti, G.; Liu, W.; Katritch, V.; Abagyan, R.; Brooun, A.; Wells, P.; Bi, F. C.; Hamel, D. J.; Kuhn, P.; Handel, T. M.; Cherezov, V.; Stevens, R. C. Structures of the CXCR4 Chemokine GPCR with Small-Molecule and Cyclic Peptide Antagonists Science 2010, 330 (6007) 1066-1071
44. Manglik, A.; Kruse, A. C.; Kobilka, T. S.; Thian, F. S.; Mathiesen, J. M.; Sunahara, R. K.; Pardo, L.; Weis, W. I.; Kobilka, B. K.; Granier, S. Crystal structure of the mu-opioid receptor bound to a morphinan antagonist Nature 2012, 485 (7398) 321-326
45. Ilien, B.; Franchet, C.; Bernard, P.; Morisset, S.; Weill, C. O.; Bourguignon, J. J.; Hibert, M.; Galzi, J. L. Fluorescence resonance energy transfer to probe human M1 muscarinic receptor structure and drug binding properties J. Neurochem. 2003, 85 (3) 768-778
46. Bazin, H.; Trinquet, E.; Mathis, G. Time resolved amplification of cryptate emission: a versatile technology to trace biomolecular interactions J. Biotechnol. 2002, 82 (3) 233-250
47. Keppler, A.; Gendreizig, S.; Gronemeyer, T.; Pick, H.; Vogel, H.; Johnsson, K. A general method for the covalent labeling of fusion proteins with small molecules in vivo Nature Biotechnol. 2003, 21 (1) 86-89
48. Zwier, J. M.; Roux, T.; Cottet, M.; Durroux, T.; Douzon, S.; Bdioui, S.; Gregor, N.; Bourrier, E.; Oueslati, N.; Nicolas, L.; Tinel, N.; Boisseau, C.; Yverneau, P.; Charrier-Savournin, F.; Fink, M.; Trinquet, E. A Fluorescent Ligand-Binding Alternative Using Tag-lite (R) Technology J. Biomol. Screening 2010, 15 (10) 1248-1259
49. Cottet, M; A., L.; Comps-Agrar, L; Trinquet, E; Pin, J. P.; Mouillac, B; Durroux, T. Time resolved FRET strategy with fluorescent ligands to analyze receptor interactions in native tissues: application to GPCR oligomerization Methods Mol. Biol. 2011, 746, 373-387