Structure-activity relationships and structural conformation of a novel urotensin II-related peptide

Peptides

Volumn 25, Issue 10 SPEC. ISS., 2004, Pages 1819-1830

  Chatenet, David ^a   Dubessy, Christophe ^a   Leprince, Jérôme ^a   Boularan, Cédric ^d   Carlier, Ludovic ^b   Ségalas Milazzo, Isabelle ^b   Guilhaudis, Laure ^b   Oulyadi, Hassan ^b   Davoust, Daniel ^b   Scalbert, Elizabeth ^c   Pfeiffer, Bruno ^c   Renard, Pierre ^c   Tonon, Marie Christine ^a   Lihrmann, Isabelle ^a   Pacaud, Pierre ^d   Vaudry, Hubert ^a  

^a INSERM   (France)

^b UNIVERSITÉ DE ROUEN   (France)

^c IDRS   (France)

^d UNIVERSITÉ DE NANTES   (France)

Author keywords

Ala scan; Conformational analysis; d scan; Ligand binding; NMR; Rat aortic ring contraction; Solid phase peptide synthesis; Structure activity relationships; Urotensin II receptor; Urotensin II related peptide

Indexed keywords

G PROTEIN COUPLED RECEPTOR 14; HYDROXYALANYLCYSTEINYLALANYLTRYPTOPHYLLYSYLTYROSYLCYSTEINYLVALINE; HYDROXYALANYLCYSTEINYLPHENYLALANYLALANYLLYSYLTYROSYLCYSTEINYLVALINE; HYDROXYALANYLCYSTEINYLPHENYLALANYLTRYPTOPHYLALANYLTYROSYLCYSTEINYLVALINE; HYDROXYALANYLCYSTEINYLPHENYLALANYLTRYPTOPHYLLYSYLALANYLCYSTEINYLVALINE; HYDROXYALANYLCYSTEINYLPHENYLALANYLTRYPTOPHYLLYSYLTYROSYLCYSTEINYLALANINE; HYDROXYALANYLCYSTEINYLPHENYLALANYLTRYPTOPHYLLYSYLTYROSYLCYSTEINYLVALINE; HYDROXYGLUTAMYLTHREONYLPROLYLASPARTYLCYSTEINYLPHENYLALANYLTRYPTOPHYLLYSYL TYROSYLCYSTEINYLVALINE; NEUROPEPTIDE RECEPTOR; PEPTIDE FRAGMENT; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANIMAL CELL; ARTICLE; BINDING AFFINITY; BIOASSAY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; EVOKED MUSCLE RESPONSE; GENETIC TRANSFECTION; MOLECULAR DYNAMICS; MUSCLE CONTRACTILITY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; VASCULAR RING;

EID: 5144231980     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2004.04.019     Document Type: Article

References (70)

1. F. Albericio, R.P. Hammer, C. Garcia-Echeverria, M.A. Molins, J.L. Chany, and M.C. Munson Cyclization of disulfide-containing peptides in solid-phase synthesis Int J Pept Protein Res 37 1991 402 413
2. R.S. Ames, H.M. Sarau, J.K. Chambers, R.N. Willette, N.V. Aiyar, and A.M. Romanic Human urotensin-II is a potent vasoconstrictor and agonist for the orphan receptor GPR14 Nature 401 1999 282 286
3. M. Basille, D. Vaudry, Y. Coulouarn, S. Jégou, I. Lihrmann, and A. Fournier Comparative distribution of pituitary adenylate cyclase-activating polypeptide (PACAP) binding sites and PACAP receptor mRNAs in the rat brain during development J Comp Neurol 425 2000 495 509
4. A.G. Beck-Sickinger, W. Gaida, G. Schorrenberg, R. Lang, and G. Jung Neuropeptide Y: identification of the binding site Int J Pept Protein Res 36 1990 522 530
5. D.J. Behm, C.L. Herold, E.H. Ohlstein, S.D. Knight, D. Dhanak, and S.A. Douglas Pharmacological characterization of SB-710411 (Cpa-c[d-Cys-Pal-d-Trp- Lys-Val-Cys]-Cpa-amide), a novel peptidic urotensin-II receptor antagonist Br J Pharmacol 137 2002 449 458
6. D.J. Behm, S.M. Harrison, Z. Ao, K. Maniscalco, S.J. Pickering, and E.V. Grau Deletion of the UT receptor gene results in the selective loss of urotensin-II contractile activity in aortae isolated from UT receptor knockout mice Br J Pharmacol 139 2003 464 472
7. R. Bhaskaran, A.I. Arunkumar, and C. Yu NMR and dynamical simulated annealing studies on the solution conformation of urotensin II Biochem Biophys Acta 1199 1994 115 122
8. V. Camarda, A. Rizzi, G. Calo, G. Gendron, S.I. Perron, and E. Kostenis Effects of human urotensin II in isolated vessels of various species: comparison with other vasoactive agents Naunyn Schmiedebergs Arch Pharmacol 365 2002 141 149
9. V. Camarda, R. Guerrini, E. Kostenis, A. Rizzi, G. Calo, and A. Hattenberger A new ligand for the urotensin II receptor Br J Pharmacol 137 2002 311 314
10. J.R. Cann, R.E. London, N.A. Matwiyoff, and J.M. Stewart A combined spectroscopic study of the solution conformation of bradykinin Adv Exp Med Biol 156 1983 495 500
11. S.D. Clark, H.P. Nothacker, Z. Wang, Y. Saito, F.M. Leslie, and O. Civelli The urotensin II receptor is expressed in the cholinergic mesopontine tegmentum of the rat Brain Res 923 2001 120 127
12. J.M. Conlon, D. Arnold-Reed, and R.J. Balment Post-translational processing of prepro-urotensin II FEBS Lett 266 1990 37 40
13. J.M. Conlon, F. O'Harte, D.D. Smith, R.J. Balment, and N. Hazon Purification and characterization of urotensin II and parvalbumin from an elasmobranch fish, Scyliorhinus canicula (common dogfish) Neuroendocrinology 55 1992 230 235
14. J.M. Conlon, F. O'Harte, D.D. Smith, M.C. Tonon, and H. Vaudry Isolation and primary structure of urotensin II from the brain of a tetrapod, the frog Rana ridibunda Biochem Biophys Res Commun 188 1992 578 583
15. J.M. Conlon, K. Yano, D. Waugh, and M. Hazon Distribution and molecular forms of urotensin II and its role in cardiovascular regulation in vertebrates J Exp Zool 275 1996 226 238
16. Y. Coulouarn, I. Lihrmann, S. Jégou, Y. Anouar, H. Tostivint, and J.C. Beauvillain Cloning of the cDNA encoding the urotensin II precursor in frog and human reveals intense expression of the urotensin II gene in motoneurons of the spinal cord Proc Natl Acad Sci 95 1998 15803 15808
17. Y. Coulouarn, S. Jégou, H. Tostivint, H. Vaudry, and I. Lihrmann Cloning, sequence analysis and tissue distribution of the mouse and rat urotensin II precursors FEBS Lett 457 1999 28 32
18. D.H. Coy, W.J. Rossowski, B.L. Cheng, and J.E. Taylor Structural requirements at the N-terminus of urotensin II octapeptides Peptides 23 2002 2259 2264
19. S.A. Douglas, A.C. Sulpizio, V. Piercy, H.M. Sarau, R.S. Ames, and N.V. Aiyar Differential vasoconstrictor activity of human urotensin-II in vascular tissue isolated from the rat, mouse, dog, pig, marmoset and cynomolgus monkey Br J Pharmacol 131 2000 1262 1274
20. S.A. Douglas, L. Tayara, E.H. Ohlstein, N. Halawa, and A. Giaid Congestive heart failure and expression of myocardial urotensin II Lancet 359 2002 1990 1997
21. N.A. Elshourbagy, S.A. Douglas, U. Shabon, S. Harrison, G. Duddy, and J.L. Sechler Molecular and pharmacological characterization of genes encoding urotensin-II peptides and their cognate G-protein-coupled receptors from the mouse and monkey Br J Pharmacol 136 2002 9 22
22. S. Flohr, M. Kurz, E. Kostenis, A. Brkovich, A. Fournier, and T. Klabunde Identification of nonpeptidic urotensin II receptor antagonists by virtual screening based on a pharmacophore model derived from structure-activity relationships and nuclear magnetic resonance studies on urotensin II J Med Chem 45 2002 1799 1805
23. M. Galantino, R. de Castiglione, C. Cristiani, F. Vaghi, W. Liu, and J.W. Zhang d-Amino acid scan of endothelin: importance of amino acids adjacent to cysteinyl residues in isomeric selectivity Pept Res 8 1988 154 159
24. J. Gartlon, F. Parker, D.C. Harrison, S.A. Douglas, T.E. Ashmeade, and G.J. Riley Central effects of urotensin-II following ICV administration in rats Psychopharmacology 155 2001 426 433
25. A. Gibson, H.A. Bern, M. Ginsburg, and J.H. Botting Neuropeptide-induced contraction and relaxation of the mouse anococcygeus muscle Proc Natl Acad Sci U.S.A. 81 1984 625 629
26. A. Gibson, P. Wallace, and H.A. Bern Cardiovascular effects of urotensin II in anesthetized and pithed rats Gen Comp Neurol 64 1986 435 439
27. P. Grieco, A. Carotenuto, P. Campiglia, E. Zampelli, R. Patacchini, and C.A. Maggi A new, potent urotensin II receptor peptide agonist containing a Pen residue at the disulfide bridge J Med Chem 45 2002 4391 4394
28. P. Grieco, A. Carotenuto, R. Patacchini, C.A. Maggi, E. Novellino, and P. Rovero Design, synthesis, conformational analysis, and biological studies of urotensin-II lactam analogues Bioorg Med Chem 10 2002 3731 3739
29. D.W. Hay, H.W. Luttman, and S.A. Douglas Human urotensin-II is a potent spasmogen of primate airway smooth muscle Br J Pharmacol 131 2000 10 12
30. M. Hedenstrom, Z. Yuan, K. Brickmann, J. Carlsson, K. Ekholm, and B. Johansson Conformations and receptor activity of desmopressin analogues, which contain γ-turn mimetics or a ψ[CH(2)O] isostere J Med Chem 45 2002 2501 2511
31. C.L. Herold, D.J. Behm, P.T. Buckley, J.J. Foley, W.E. Wixted, and H.M. Sarau The neuromedin B receptor antagonist, BIM-23127, is a potent antagonist at human and rat urotensin-II receptors Br J Pharmacol 139 2002 203 207
32. T. Ichikawa, K. Lederis, and H. Kobayashi Primary structures of multiple forms of urotensin II in the urophysis of the carp Cyprinus Carpio Gen Comp Endocrinol 55 1984 133 141
33. W.A. Kinney, H.R.J.R. Almond, J. Qi, C.E. Smith, R.J. Santulli, and L. de Garavilla Structure-function analysis of urotensin II and its use in the construction of a ligand-receptor working model Angew Chem Int Ed 41 2002 240 244
34. P. Labarrère, D. Chatenet, J. Leprince, C. Marionneau, G. Loirand, and M.C. Tonon Structure-activity relationships of human urotensin II and related analogues on rat aortic ring contraction J Enz Inh Med Chem 18 2003 77 88
35. B. Leitbeg, F. Otvos, and G. Toth Conformational analysis of endomorphin-2 by molecular dynamics methods Biopolymers 68 2003 497 511
36. J.C. Le Mevel, K.R. Olson, D. Conklin, D. Waugh, D.D. Smith, and H. Vaudry Cardiovascular actions of trout urotensin II in the conscious trout, Oncorhynchus mykiss Am J Physiol 271 1996 1335 1343
37. J. Leprince, P. Gandolfo, J.L. Thoumas, C. Patte, J.L. Fauchère, and H. Vaudry Structure-activity relationships of a series of analogues of the octadecaneuropeptide ODN on calcium mobilization in rat astrocytes J Med Chem 41 1998 4433 4438
38. J. Leprince, H. Oulyadi, D. Vaudry, O. Masmoudi, P. Gandolfo, and C. Patte Synthesis, conformational analysis and biological activity of cyclic analogs of the octadecaneuropeptide ODN Design of a potent endozepine antagonist Eur J Biochem 268 2001 6045 6057
39. P.N. Lewis, F.A. Momany, and H.A. Scheraga Chain reversals in proteins Biochem Biophys Acta 303 1973 211 219
40. Q. Liu, S.S. Pong, Z. Zeng, Q. Zhang, A.D. Howard, and D.L. Williams Identification of urotensin II as the endogenous ligand for the orphan G-protein-coupled receptor GPR14 Biochem Biophys Res Commun 266 1999 174 178
41. Y. Lu, C.J. Zou, D.W. Huang, and C.S. Tang Cardiovascular effects of urotensin II in different brain areas Peptides 23 2002 1631 1635
42. A. Marchese, M. Heiber, T. Nguyen, H.H.Q. Heng, V.R. Saldivia, and R. Cheng Cloning and chromosomal mapping of three novel genes, GPR9, GPR10, and GPR14, encoding receptors related to interleukin 8, neuropeptide Y, and somatostatin receptors Genomics 29 1995 335 344
43. 15N Hartmann-Hahn-multiple quantum coherence and nuclear Overhauser-multiple quantum coherence spectroscopy: application to IL1β Biochemistry 28 1989 6150 6156
44. M. Matsushita, M. Shichiri, T. Imai, M. Iwashina, H. Tanaka, and N. Takasu Co-expression of urotensin II and its receptor (GPR14) in human cardiovascular and renal tissues J Hypertens 19 2001 2185 2190
45. D. McMaster, and K. Lederis Isolation and amino acid sequence of two urotensin II peptides from Catostomus commersoni urophyses Peptides 4 1983 367 373
46. D. McMaster, M.A. Belenky, A.L. Polenov, and K. Lederis Isolation and amino acid sequence of urotensin II from the sturgeon Acipenser ruthenus Gen Comp Endocrinol 87 1992 275 285
47. M. Mori, T. Sugo, M. Abe, Y. Shimomura, M. Kurihara, and C. Kitada Urotensin II is the endogenous ligand of a G-protein-coupled orphan receptor, SENR (GPR14) Biochem Biophys Res Commun 265 1999 123 129
48. 1 receptor agonist J Biol Chem 275 2000 24003 240012
49. M. Nilges, G.M. Clore, and A.M. Gronenborn Determination of three-dimensional structures of proteins from interproton distance data by hybrid distance geometry-dynamical simulated annealing calculations FEBS Lett 229 1988 317 324
50. H.P. Nothacker, Z. Wang, A.M. McNeill, Y. Saito, S. Merten, and B. O'Dowd Identification of the natural ligand of an orphan G-protein-coupled receptor involved in the regulation of vasoconstriction Nat Cell Biol 1 1999 383 385
51. S. Ohsako, I. Ishida, T. Ichikawa, and T. Deguchi Cloning and sequence analysis of cDNAs encoding precursors of urotensin II-α and -γ J Neurosci 6 1986 2730 2735
52. 3JHN alpha for identification of helical secondary structure J Mol Biol 180 1984 741 751
53. D. Pearson, J.E. Shively, B.R. Clark, I.I. Geschwind, M. Barkley, and R.S. Nishioka Urotensin II: a somatostatin-like peptide in the caudal neurosecretory system of fishes Proc Natl Acad Sci U.S.A. 77 1980 5021 5024
54. T.D.J. Perkins, S. Bansal, and D.J. Barlow Molecular modelling and design of analogues of the peptide hormone urotensin II Biochem Soc Trans 18 1990 918 919
55. G.D. Rose, L.M. Gierasch, and J.A. Smith Turns in peptides and proteins Adv Protein Chem 37 1985 1 109
56. V. Sauzeau, E. Le Mellionnec, J. Bertoglio, E. Scalbert, P. Pacaud, and G. Loirand Human urotensin II-induced contraction and arterial smooth muscle cell proliferation are mediated by RhoA and Rho-kinase Circ Res 88 2001 1102 1104
57. P. Sieber An improved method for anchoring of 9-fluorenylmethoxycarbonyl- amino acids to 4-alkoxybenzylalcohol resins Tetrahedron Lett 28 1987 6147 6150
58. 15N HSQC experiments optimized to retain full sensitivity J Magn Reson 102 1993 241 245
59. J.A. Smith, and L.G. Pease Reverse turns in peptides and proteins Crit Rev Biochem 8 1980 315 399
60. T. Sugo, Y. Murakami, Y. Shimomura, M. Harada, M. Abe, and Y. Ishibashi Identification of urotensin II-related peptide as the urotensin II-immunoreactive molecule in the rat brain Biochem Biophys Res Commun 310 2003 860 868
61. M. Tal, D.A. Ammar, M. Karpuj, V. Krizhanovsky, M. Naim, and D.A. Thompson A novel putative neuropeptide receptor expressed in neural tissue, including sensory epithelia Biochem Biophys Res Commun 209 1995 752 759
62. K. Tamura, M. Okazaki, M. Tamura, K. Isozumi, H. Tasaki, and Y. Nakashima Urotensin II-induced activation of extracellular signal-regulated kinase in cultured vascular smooth muscle cells: involvement of cell adhesion-mediated integrin signaling Life Sci 72 2003 1049 1060
63. K. Totsune, K. Takahashi, Z. Arihara, M. Sone, F. Satoh, and S. Ito Role of urotensin II in patients on dialysis Lancet 358 2001 810 811
64. A. Tzanidis, R.D. Hannan, W.G. Thomas, D. Onan, D.J. Autelitano, and F. See Direct actions of urotensin II on the heart: implications for cardiac fibrosis and hypertrophy Circ Res 93 2003 246 253
65. D.F. Veber, F.W. Holly, R.F. Nutt, S.J. Bergstrand, S.F. Brady, and R. Hirschmann Highly active and bicyclic somatostatin analogues of reduced ring size Nature 280 1979 512 514
66. T. Watanabe, R. Pakala, T. Katagiri, and C.R. Benedict Synergistic effect of urotensin II with mildly oxidized LDL on DNA synthesis in vascular smooth muscle cells Circulation 104 2001 16 18
67. D. Waugh, and J.M. Conlon Purification and characterization of urotensin II from the brain of a teleost (trout, Oncorhynchus mykiss) and an elasmobranch (skate, Raja rhina) Gen Comp Endocrinol 92 1993 419 427
68. D. Waugh, J. Youson, S.D. Mims, S. Sower, and J.M. Conlon Urotensin II from the river lamprey (Lampetra fluviatilis), the sea lamprey (Petromyzon marinus), and the paddlefish (Polyodon spathula) Gen Comp Endocrinol 99 1995 323 332
69. Wüthrich K. In: Wiley J., editor. NMR of proteins and nucleic acids. New York 1986.
70. Y. Zou, R. Nagai, and T. Yamazaki Urotensin II induces hypertrophic responses in cultured cardiomyocytes from neonatal rats FEBS Lett 508 2001 57 60