Fluorescent pseudo-peptide linear vasopressin antagonists: Design, synthesis, and applications

Journal of Medicinal Chemistry

Volumn 42, Issue 7, 1999, Pages 1312-1319

  Durroux, Thierry ^a   Peter, Marion ^a   Turcatti, Gerardo ^b   Chollet, André ^b   Balestre, Marie Noëlle ^a   Barberis, Claude ^a   Seyer, René ^a  

^a CCIPE   (France)

^b SERONO PHARMACEUTICAL RES INSTITUTE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; INOSITOL PHOSPHATE; PSEUDOPEPTIDE; VASOPRESSIN; VASOPRESSIN ANTAGONIST;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CHO CELL; DRUG DESIGN; DRUG SYNTHESIS; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; RECEPTOR BINDING; STRUCTURE ANALYSIS; VASOPRESSIN BLOOD LEVEL;

ANIMALS; BINDING, COMPETITIVE; CELL MEMBRANE; CHO CELLS; CRICETINAE; DRUG DESIGN; FLUORESCENT DYES; HUMANS; INOSITOL PHOSPHATES; LIGANDS; OLIGOPEPTIDES; RECEPTORS, OXYTOCIN; RECEPTORS, VASOPRESSIN; RHODAMINES; SPECTROMETRY, FLUORESCENCE; TRANSFECTION;

EID: 0033535519     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9804782     Document Type: Article

References (33)

1. Jard, S.; Elands, J.; Schmidt, A.; Barberis, C. Vasopressin and oxytocin receptors: an overview. In Progress in Endocrinology; Imura, H., Shizume, K., Eds.; Elsevier: Amsterdam, 1988; pp 1183-1189.
2. Mouillac, B.; Chini, B.; Balestre, M. N.; Elands, J.; Trumpp-Kallmeyer, S.; Hoflack, J.; Hibert, M.; Jard, S.; Barberis, C. The binding site of neuropeptide vasopressin V1a receptor. Evidence for a major localization within transmembrane regions. J. Biol. Chem. 1995, 270, 25771-25777.
3. Phalipou, S.; Cotte, N.; Carnazzi, E.; Seyer, R.; Mahé, E.; Jard, S.; Barberis, C.; Mouillac, B. Mapping peptide-binding domains of the human V1a vasopressin receptor with a photoactivatable linear peptide antagonist. J. Biol. Chem. 1997, 272, 26536-26544.
4. Kojro, E.; Eich, P.; Gimpl, G.; Fahrenholz, F. Direct identification of an extracellular agonist binding site in the renal V2 vasopressin receptor. Biochemistry 1993, 32, 13537-13544.
5. MacGrath, J. C.; Arribas, S.; Daly, C. J. Fluorescent ligands for the study of receptors. Trends Pharmacol. Sci. 1996, 17, 393-399.
6. Hein, L.; Meinel, L.; Pratt, E.; Dzau, V. J.; Kobilka, B. K. Intracellular trafficking of angiotensin II and its AT1 and AT2 receptors: evidence for selective sorting of receptor and ligand. Mol. Endocrinol. 1997, 11, 1266-1277.
7. Zagyansky, Y. A.; Jard, S. Does lectin-receptor complex formation produce zones of restricted mobility within the membrane? Nature 1979, 280, 591-593.
8. Sterrer, S.; Henco, K Fluorescence correlation spectroscopy (FCS) - a highly sensitive method to analyse drug/target interactions. J. Recept. Signal Transd. Res. 1997, 17, 511-520.
9. Raines, D. E.; Krishnan, N. S. Transient low-affinity agonist binding to Torpedo postsynaptic membranes resolved by using sequential mixing stopped-flow fluorescence spectroscopy. Biochemistry 1998, 37, 956-964.
10. Turcatti, G.; Vogel, H.; Chollet, A. Probing the binding domain of the NK2 receptor with fluorescent ligands: evidence that heptapeptide agonists and antagonists bind differently. Biochemistry 1995, 34, 3972-3980.
11. Tota, M. R.; Daniel, S.; Sirotina, A.; Mazina, K. E.; Frong, T. M.; Longmore, J.; Strader, C. D. Characterization of a fluorescent substance P analogue. Biochemistry 1994, 33, 13079-13086.
12. Turcatti, G.; Nemeth, K.; Edgerton, M.; Knowles, J.; Vogel, H.; Chollet, A. Fluorescent labeling of NK2 receptor at specific sites in vivo and fluorescence energy transfer analysis of NK2 ligand-receptor complexes. Recept. Channels 1997, 5, 201-207.
13. 2-containing linear V2 agonists: potential radioiodinated ligand for vasopressin receptors. In Peptides 1990; Giralt, E., Andreu, D., Eds.; Escom Science Publishers B.V.: Leiden, 1991; pp 665-667.
14. Manning, M.; Bankowski, K.; Barberis, C.; Jard, S.; Elands, J.; Chan, W. Y. Novel approach to the design of synthetic radio-iodinated linear V1a receptor antagonists of vasopressin. Int. J. Pept. Protein Res. 1992, 40, 261-267.
15. Lutz, W. H.; Londowski, J. M.; Kumar, R. The synthesis and biological activity of four novel fluorescent vasopressin analogues. J. Biol. Chem. 1990, 265, 4657-4663.
16. Yuan, T.; Weljie, A. M.; Vogel, H. J. Tryptophan fluorescence quenching by methionine and selenomethionine residues of calmodulin: orientation of peptide and protein binding. Biochemistry 1998, 37, 3187-3195.
17. 8]-vasopressin measured using frequency-domain fluorescence resonance energy transfer. Eur. Biophys. J. 1996, 24, 185-193.
18. Carnazzi, E.; Aumelas, A.; Barberis, C.; Guillon, G.; Seyer, R. A new series of photoactivatable and iodinatable linear vasopressin antagonists. J. Med. Chem. 1994, 37, 1841-1849.
19. Guillon, G.; Barbeau, D.; Neugebauer, W.; Guay, S.; Bilodeau, L.; Balestre, M. N.; Gallo-Payet, N.; Escher, E. Fluorescent peptide hormones: development of high affinity vasopressin analogues. Peptides 1992, 13, 7-11.
20. Haugland, R. P. In Handbook of fluorescent probes and research chemicals; Spence, M. T. Z., Ed.; Eugene, 1996.
21. Faure, M-P.; Gaudreau, P.; Shaw, I.; Cashman, N. R.; Beaudet, A. Synthesis of a biologically active fluorescent probe for labeling neurotensin receptors. J. Histochem. Cytochem. 1994, 42, 755-763.
22. Frérot, E.; Coste, J.; Pantaloni, A.; Dufour, M. N.; Jouin, P. PyBOP and PyBroP: two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib. Tetrahedron 1991, 47, 259-270.
23. Barberis, C.; Balestre, M.-N.; Jard, S.; Tribollet, E.; Arsenijevic, Y.; Dreifuss, J.-J.; Bankowski, K.; Manning, M.; Chan, W. Y.; Schlosser, S. S.; Holsboer, F.; Elands, J. Characterization of a novel linear radioiodinated vasopressin antagonist: an excellent radioligand for vasopressin V1a receptors. Neuroendocrinology 1995, 62, 135-146.
24. Schmidt, A.; Audigier, S.; Barberis, C.; Jard, S.; Manning, M.; Kolodziejczyk, A. S.; Sawyer, W. H. A radioiodinated linear vasopressin antagonist: a ligand with high affinity and specificity for V1a receptors. FEBS Lett. 1991, 252, 77-81.
25. Serradeil-Le Gal, C.; Wagnon, J.; Garcia, C.; Lacour, P.; Guiraudou, P.; Christophe, B.; Villanova, G.; Nisato, D.; Maffrand, J. P.; Le Fur, G.; Guillon, G.; Cantau, B.; Barberis, C.; Trueba, M.; Ala, Y.; Jard, S. Biochemical and pharmacological properties of SR 49059, a new potent, non-peptide antagonist of rat and human vasopressin V1a receptors. J. Clin. Invest. 1993, 92, 224.
26. Kirk, C. J.; Guillon, G.; Balestre, M.-N.; Jard, S. Stimulation, by vasopressin and other agonists, of inositol-lipid breakdown and inositol phosphate accumulation in WRK1 cells. Biochem. J. 1986, 240, 197-204.
27. Lutz, W.; Londowki, J. M.; Sanders, M.; Salisbury, J.; Kumar, R. A vasopressin analogue that binds but does not activate V1 or V2 vasopressin receptors is not internalized into cells that express V1 or V2 receptors. J. Biol. Chem. 1992, 267, 1109-1115.
28. Jans, D. A.; Peters, R.; Zsigo, J.; Fahrenholz, F. The adenylate cyclase-coupled vasopressin V2-receptor is highly laterally mobile in membranes of LLC-PK1 renal epithelial cells at physiological temperature. EMBO J, 1989, 8, 2481-2488.
29. Strakova, Z.; Kumar, A.; Watson, A. J.; Soloff, M. S. A new linear V1a vasopressin antagonist and its use in characterizing receptor/G protein interactions. Mol. Pharmacol. 1997, 51, 217-224.
30. Coste, J.; Le-Nguyen, D.; Castro, B. PyBOP: a new peptide coupling reagent devoid of toxic byproduct. Tetrahedron Lett. 1990, 31, 205-208.
31. 9]OVT: a selective oxytocin receptor ligand. Eur. J. Pharmacol. 1987, 147, 197-207.
32. Seyer, R.; Aumelas, A. Synthesis of biotinylated and photoreactive probes for angiotensin receptors. J. Chem. Soc., Perkin Trans. 1 1990, 3289-3299.
33. Kassis, S.; Henneberry, R. C.; Fishman, P. H. Induction of catecholamine-responsive adenylate cyclase in HeLa cells by sodium butyrate. J. Biol. Chem. 1984, 259, 4910-4916.