Efficient photoaffinity labeling of the rat V(1a) vasopressin receptor using a linear azidopeptidic antagonist

European Journal of Biochemistry

Volumn 247, Issue 3, 1997, Pages 906-913

  Carnazzi, Eric ^a,c   Aumelas, André ^b   Phalipou, Sylvie ^c   Mouillac, Bernard ^c   Guillon, Gilles ^c   Barberis, Claude ^c   Seyer, René ^a  

^a CNRS UPR 9023   (France)

^b INSERM   (France)

^c CCIPE   (France)

Author keywords

Antagonist; Photoaffinity; Proteolysis; Receptor; Vasopressin

Indexed keywords

RECEPTOR SUBTYPE; RECOMBINANT PROTEIN; VASOPRESSIN ANTAGONIST; VASOPRESSIN V1 RECEPTOR;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CELL STRAIN COS1; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GENE EXPRESSION; IN VITRO STUDY; ISOTOPE LABELING; LEPIDOPTERA; LIVER; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; RAT; ULTRAVIOLET SPECTROSCOPY;

ANIMALIA; LEPIDOPTERA; SPODOPTERA FRUGIPERDA;

EID: 0030835940     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00906.x     Document Type: Article

References (43)

1. Akhuntiova, A., Getmanova, E., Gorbulev, V., Carnazzi, E., Eggena, P. & Fahrenholz, F. (1996) Cloning and functional characterization of the amphibian mesotocin receptor, a member of the oxytocin/vasopressin receptor superfamily, Eur. J. Biochem. 237, 759-767.
2. Barbeau, D., Guay, S., Neugebauer, W. & Escher, E. (1992) Preparation and biological activities of potential vasopressin photoaffinity labels, J. Med. Chem. 35, 151-157.
3. Barbeau, D., Bouley, R. & Escher, E. (1996) Molecular weight determination of the hepatic vasopressin receptor with a high-affinity probe, Int. J. Pept. Protein Res. 48, 364-373.
4. 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. (1995) Characterization of a novel, linear radioiodinated vasopressin antagonist: an excellent radioligand for vasopressin V1a receptors, Neuroendocrinology 62, 135-146.
5. Bax, A. & Davis, D. G. (1985) MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy, J. Magn. Reson. 65, 355-360.
6. Bax, A. & Subramanian, S. (1986) Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy, J. Magn. Reson. 67, 565-569.
7. Boer, R. & Fahrenholz, F. (1985) Photoaffinity labeling of the V1 vasopressin receptor in plasma membranes from rat liver, J. Biol. Chem. 260, 15051-15054.
8. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72, 248-254.
9. Brunner, J. (1993) New photolabeling and crosslinking methods, Annu. Rev. Biochem. 62, 483-514.
10. Buku, A., Gazis, D. & Eggena, P. (1989) Photoaffinity, biotinyl and iodo analogues as probes for vasotocin receptors, J. Med. Chem. 32, 2432-2435.
11. Carnazzi, E., Aumelas, A., Barberis, C., Guillon, G. & Seyer, R. (1994) A new series of photoactivatable and iodinatable linear vasopressin antagonists, J. Med. Chem. 37, 1841-1849.
12. Castro, B., Evin, G., Selve, C. & Seyer, R. (1977) Peptide coupling reagents; VIII. A high yield preparation of phenyl esters of amino acids using benzotriazolyloxytris[dimethylamino]phosphonium hexafluorophosphate (BOP reagent), Synthesis, 413.
13. Chini, B., Mouillac, B., Ala, Y., Balestre, M.-N., Trumpp-Kallmeyer, S., Hoflack, J., Elands, J., Hibert, M., Manning, M., Jard, S. & Barberis, C. (1995) Tyr115 is the key residue for determining agonist selectivity in the Via vasopressin receptor, EMBO J. 14, 2176-2182.
14. ®: a new peptide coupling reagent devoid of toxic by-product, Tetrahedron Lett. 31, 205-208.
15. Eberlé, A. N., Drozdz, R., Solca, F. & Jürg, G. (1991) Peptides containing multiple photolabels for studies of hormone-receptor interactions, in Peptides 1990 (Giralt, E. & Andreu, D., eds) pp. 692-694.
16. Fahrenholz, F., Kojro, E., Müller, M., Boer, R., Löhr, R. & Grzonka, Z. (1986) Iodinated photoreactive vasopressin antagonists: labelling of hepatic vasopressin receptor subunits, Eur. J. Biochem. 161, 321-328.
17. Hinko, A., Soloff, M. S. & Potier, M. (1992) Molecular size characterization of oxytocin receptors in rabbit amnion, Endocrinology 130, 3554-3559.
18. Hutchins, A. M., Phillips, P. A., Venter, D. J., Burrell, L. M. & Johnston, C. I. (1995) Molecular cloning and sequencing of the gene encoding a sheep arginine vasopressin type 1a receptor, Biochim. Biophys. Acta 1263, 266.
19. Innamorati, G., Lolait, S. J. & Birnbaumer, M. (1995) Sequence identity between the rat and human vasopressin Via receptors, Biochem. J. 314, 709-711.
20. Jard, S. (1983) Vasopressin isoreceptors in mammals: relation to cyclic AMP-dependent and cyclic AMP-independent transduction mechanisms, Curr. Top. Membr. Transp. 18, 255-285.
21. Kojro, E., Eich, P., Gimpl, G. & Fahrenholz, F. (1993) Direct identification of an extracellular agonist binding site in the renal V2 vasopressin receptor, Biochemistry 32, 13537-13544.
22. Kojro, E. & Fahrenholz, F. (1995) Ligand-induced cleavage of the V2 vasopressin receptor by a plasma membrane metalloproteinase, J. Biol. Chem. 270, 6476-6481.
23. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4, Nature 227, 680-685.
24. Lerner, L. & Bax, A. (1986) Sensitivity-enhanced two-dimensional heteronuclear relayed coherence transfer NMR spectroscopy, J. Magn. Reson. 69, 375-380.
25. Luckow, V. A. & Summers, M. D. (1988) Signals important for high level expression of foreign genes in Autographa Californica nuclear polyhedrosis virus expression vectors, Bio-technology (NY) 6, 47-55.
26. Macura, S., Huang, Y., Sutter, D. & Ernst, R. R. (1981) Two-dimensional chemical exchange and cross relaxation spectroscopy of coupled nuclear spins, J. Magn. Reson. 43, 259-281.
27. Manning, M., Klis, W. A., Kruszynski, M., Przybylski, J. P., Olma, A., Wo, N. C., Pelton, G. H. & Sawyer, W. H. (1988) Novel linear antagonists of the antidiuretic (V2) and vasopressor (V1) responses to vasopressin, Int. J. Pept. Protein Res. 32, 455-467.
28. Manning, M. & Sawyer, W. H. (1993) Design, synthesis and some uses of receptor-specific agonists and antagonists of vasopressin and oxytocin, J. Recept. Res. 13, 195-214.
29. Marie, J. & Roy, C. (1988) Covalent labeling of vasopressin receptors from LLC-PK1 cells by the use of a bifunctionnal reagent, Mol. Pharmacol. 33, 432-440.
30. Morel, A., O'Carrol, A.-M., Brownstein, M. J. & Lolait, S. J. (1992) Molecular cloning and expression of a rat V1a arginine vasopressin receptor, Nature 356, 523-526.
31. Mouillac, B., Caron, M., Bonin, H., Dennis, M. & Bouvier, M. (1992) Agonist-modulated palmitoylation of β2-adrenergic receptor in Sf9 cells, J. Biol. Chem. 267, 21 733-21 737.
32. Mouillac, B., Chini, B., Balestre, M.-N., Elands, J., Trumpp-Kallmeyer, S., Hoflack, J., Hibert, M., Jard, S. & Barberis, C. (1995) The binding site of neuropeptide vasopressin V1a receptor, J. Biol. Chem. 270, 25 771-25 777.
33. Munson, P. J. & Rodbard, D. (1980) Ligand: a versatile computerized approach for characterization of ligand-binding systems, Anal. Biochem. 107, 220-239.
34. Neville, D. M. (1968) Isolation of an organic specific protein antigen from cell-surface membrane of rat liver, Biochim. Biophys. Acta 154, 540-522.
35. Rance, M., Sorensen, O. W., Bodenhausen, G., Wagner, G., Ernst, R. R. & Wüthrich, K. (1983) Improved spectral resolution in COSY 1H NMR spectra of proteins via double quantum filtering, Biochem. Biophys. Res. Commun. 117, 479-485.
36. Ratnam, M., Le Nguyen, D., Rivier, J., Sargent, P. B. & Lindstrom, J. (1986) Transmembrane topography of nicotinic acetylcholine receptor: immunochemical tests contradict theoretical predictions based on hydrophobicity profiles, Biochemistry 25, 2633-2643.
37. Rosenthal, W., Seibold, A., Antaramian, A., Lonergan, M., Arthus, M.-F., Hendy, G. N., Birnbaumer, M. & Bichet, D. G. (1992) Molecular identification of the gene responsible for congenital nephrogenic diabetes insipidus, Nature 359, 233-235.
38. Rosenthal, W., Seibold, A., Antaramian, A., Gilbert, S., Birnbaumer, M., Bichet, D. G., Arthus, M. F. & Lonergan, M. (1994) Mutations in the vasopressin V2 receptor gene in families with nephrogenic diabetes insipidus and functional expression of the Q-2 mutant, Cell. Mol. Biol. 40, 429-436.
39. Schmidt, A., Audigier, S., Barberis, C., Jard, S., Manning, M., Kolodziejczyk, A. S. & Sawyer, W. H. (1991) A radioiodinated linear vasopressin antagonist: a ligand with high affinity and specificity for V1a receptors, FEBS Lett. 282, 77-81.
40. Servant, G., Boulay, G., Bossé, R., Escher, E. & Guillemette, G. (1993) Photoaffinity labeling of subtype 2 angiotensin receptor of human myometrum, Mol. Pharmacol. 43, 677-683.
41. Seyer, R. & Aumelas, A. (1990) Synthesis of biotinylated and photoreactive probes for angiotensin receptors, J. Chem. Soc. Perkin Trans. 1, 3289-3299.
42. Thibonnier, M., Auzan, C., Madhun, Z., Wilkins, P., Berti-Mattera, L. & Clauser, E. (1994) Molecular cloning, sequencing and functional expression of a cDNA encoding the human V1a vasopressin receptor, J. Biol. Chem. 269, 3304-3310.
43. Wüthrich, K. (1986) NMR of proteins and nucleic acids, John Wiley and Sons, New York.