Structural difference of vasoactive intestinal peptide in two distinct membrane-mimicking environments

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1814, Issue 5, 2011, Pages 724-730

  Umetsu, Yoshitaka ^a   Tenno, Takeshi ^a,b   Goda, Natsuko ^a   Shirakawa, Masahiro ^b   Ikegami, Takahisa ^c   Hiroaki, Hidekazu ^a,d  

^a KOBE UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d KOBE UNIVERSITY   (Japan)

Author keywords

Dodecylphosphocholine micelle; G protein coupled receptor; NMR structure; Pituitary adenylate cyclase activating peptide; Vasoactive intestinal peptide

Indexed keywords

G PROTEIN COUPLED RECEPTOR; HYPOPHYSIS ADENYLATE CYCLASE ACTIVATING POLYPEPTIDE; ISOLEUCINE; METHIONINE; PHENYLALANINE; TYROSINE; VASOACTIVE INTESTINAL POLYPEPTIDE; WATER;

AMINO TERMINAL SEQUENCE; ARTICLE; HYDROPHOBICITY; MICELLE; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN LOCALIZATION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; PITUITARY ADENYLATE CYCLASE-ACTIVATING POLYPEPTIDE; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE; VASOACTIVE INTESTINAL PEPTIDE;

EID: 79955588011     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbapap.2011.03.009     Document Type: Article

References (49)

1. B.H. Du, J. Eng, J.D. Hulmes, M. Chang, Y.C. Pan, and R.S. Yalow Guinea pig has a unique mammalian VIP Biochem. Biophys. Res. Commun. 128 1985 1093 1098 (Pubitemid 15008257)
2. S. Onoue, S. Misaka, and S. Yamada Structure-activity relationship of vasoactive intestinal peptide (VIP): potent agonists and potential clinical applications Naunyn Schmiedebergs Arch. Pharmacol. 377 2008 579 590
3. M. Laburthe, A. Couvineau, and V. Tan Class II G protein-coupled receptors for VIP and PACAP: structure, models of activation and pharmacology Peptides 28 2007 1631 1639 (Pubitemid 47371033)
4. R.M. Campbell, and C.G. Scanes Evolution of the growth hormone-releasing factor (GRF) family of peptides Growth Regul. 2 1992 175 191
5. G.V. Segre, and S.R. Goldring Receptors for secretin, calcitonin, parathyroid hormone (PTH)/PTH-related peptide, vasoactive intestinal peptide, glucagonlike peptide 1, growth hormone-releasing hormone, and glucagon belong to a newly discovered G-protein-linked receptor family Trends Endocrinol. Metab. 4 1993 309 314 (Pubitemid 24009874)
6. S.R. Rawlings, and M. Hezareh Pituitary adenylate cyclase-activating polypeptide (PACAP) and PACAP/vasoactive intestinal polypeptide receptors: actions on the anterior pituitary gland Endocr. Rev. 17 1996 4 29 (Pubitemid 26061365)
7. M. Laburthe, M. Rousset, C. Boissard, G. Chevalier, A. Zweibaum, and G. Rosselin Vasoactive intestinal peptide: a potent stimulator of adenosine 3':5'-cyclic monophosphate accumulation in gut carcinoma cell lines in culture Proc. Natl Acad. Sci. U.S.A. 75 1978 2772 2775 (Pubitemid 8374990)
8. R. Salomon, A. Couvineau, C. Rouyer-Fessard, T. Voisin, D. Lavallee, A. Blais, D. Darmoul, and M. Laburthe Characterization of a common VIP-PACAP receptor in human small intestinal epithelium Am. J. Physiol. 264 1993 294 300
9. C.J. MacKenzie, E.M. Lutz, D.A. McCulloch, R. Mitchell, and A.J. Harmar Phospholipase C activation by VIP1 and VIP2 receptors expressed in COS 7 cells involves a pertussis toxin-sensitive mechanism Ann. NY Acad. Sci. 805 1996 579 584 (Pubitemid 27058060)
10. D.L. Bellinger, D. Lorton, S. Brouxhon, S. Felten, and D.L. Felten The significance of vasoactive intestinal polypeptide (VIP) in immunomodulation Adv. Neuroimmunol. 6 1996 5 27 (Pubitemid 26185008)
11. S.G. Smalley, P.A. Barrow, and N. Foster Immunomodulation of innate immune responses by vasoactive intestinal peptide (VIP): its therapeutic potential in inflammatory disease Clin. Exp. Immunol. 157 2009 225 234
12. M. Kojima, T. Ito, T. Oono, T. Hisano, H. Igarashi, Y. Arita, K. Kawabe, D.H. Coy, R.T. Jensen, and H. Nawata VIP attenuation of the severity of experimental pancreatitis is due to VPAC1 receptor-mediated inhibition of cytokine production Pancreas 30 2005 62 70 (Pubitemid 40070628)
13. A. Arranz, C. Abad, Y. Juarranz, J. Leceta, C. Martinez, and R.P. Gomariz Vasoactive intestinal peptide as a healing mediator in Crohn's disease Neuroimmunomodulation 15 2008 46 53
14. E. Gonzalez-Rey, and M. Delgado Therapeutic treatment of experimental colitis with regulatory dendritic cells generated with vasoactive intestinal peptide Gastroenterology 131 2006 1799 1811 (Pubitemid 44958527)
15. M. Delgado, C. Martinez, D. Pozo, J.R. Calvo, J. Leceta, D. Ganea, and R.P. Gomariz Vasoactive intestinal peptide (VIP) and pituitary adenylate cyclase-activation polypeptide (PACAP) protect mice from lethal endotoxemia through the inhibition of TNF-alpha and IL-6 J. Immunol. 162 1999 1200 1205 (Pubitemid 29035454)
16. M. Delgado, C. Abad, C. Martinez, J. Leceta, and R.P. Gomariz Vasoactive intestinal peptide prevents experimental arthritis by downregulating both autoimmune and inflammatory components of the disease Nat. Med. 7 2001 563 568 (Pubitemid 32448323)
17. M.L. Thakur, C.S. Marcus, S. Saeed, V. Pallela, C. Minami, L. Diggles, H. Le Pham, R. Ahdoot, and E.A. Kalinowski 99mTc-labeled vasoactive intestinal peptide analog for rapid localization of tumors in humans J. Nucl. Med. 41 2000 107 110 (Pubitemid 30046691)
18. M.L. Thakur, M.R. Aruva, J. Gariepy, P. Acton, S. Rattan, S. Prasad, E. Wickstrom, and A. Alavi PET imaging of oncogene overexpression using 64Cu-vasoactive intestinal peptide (VIP) analog: comparison with 99mTc-VIP analog J. Nucl. Med. 45 2004 1381 1389 (Pubitemid 47618539)
19. J.C. Reubi In vitro identification of vasoactive intestinal peptide receptors in human tumors: implications for tumor imaging J. Nucl. Med. 36 1995 1846 1853
20. C. Boissard, J.C. Marie, G. Hejblum, C. Gespach, and G. Rosselin Vasoactive intestinal peptide receptor regulation and reversible desensitization in human colonic carcinoma cells in culture Cancer Res. 46 1986 4406 4413 (Pubitemid 16046862)
21. I. Rubinstein Human VIP-alpha: an emerging biologic response modifier to treat primary pulmonary hypertension Expert Rev. Cardiovasc. Ther. 3 2005 565 569 (Pubitemid 41086817)
22. V. Sethi, H. Onyuksel, and I. Rubinstein Liposomal vasoactive intestinal peptide Meth. Enzymol. 391 2005 377 395 (Pubitemid 40254046)
23. F. Hajos, B. Stark, S. Hensler, R. Prassl, and W. Mosgoeller Inhalable liposomal formulation for vasoactive intestinal peptide Int. J. Pharm. 357 2008 286 294
24. H. Inooka, T. Ohtaki, O. Kitahara, T. Ikegami, S. Endo, C. Kitada, K. Ogi, H. Onda, M. Fujino, and M. Shirakawa Conformation of a peptide ligand bound to its G-protein coupled receptor Nat. Struct. Biol. 8 2001 161 165 (Pubitemid 32116070)
25. C. Sun, D. Song, R.A. Davis-Taber, L.W. Barrett, V.E. Scott, P.L. Richardson, A. Pereda-Lopez, M.E. Uchic, L.R. Solomon, M.R. Lake, K.A. Walter, P.J. Hajduk, and E.T. Olejniczak Solution structure and mutational analysis of pituitary adenylate cyclase-activating polypeptide binding to the extracellular domain of PAC1-RS Proc. Natl Acad. Sci. U.S.A. 104 2007 7875 7880 (Pubitemid 47185844)
26. C.R. Grace, M.H. Perrin, J. Gulyas, M.R. Digruccio, J.P. Cantle, J.E. Rivier, W.W. Vale, and R. Riek Structure of the N-terminal domain of a type B1 G protein-coupled receptor in complex with a peptide ligand Proc. Natl Acad. Sci. U.S.A. 104 2007 4858 4863 (Pubitemid 47186141)
27. S. Runge, H. Thogersen, K. Madsen, J. Lau, and R. Rudolph Crystal structure of the ligand-bound glucagon-like peptide-1 receptor extracellular domain J. Biol. Chem. 283 2008 11340 11347
28. C. Parthier, M. Kleinschmidt, P. Neumann, R. Rudolph, S. Manhart, D. Schlenzig, J. Fanghanel, J.U. Rahfeld, H.U. Demuth, and M.T. Stubbs Crystal structure of the incretin-bound extracellular domain of a G protein-coupled receptor Proc. Natl Acad. Sci. U.S.A. 104 2007 13942 13947 (Pubitemid 350003317)
29. A.A. Pioszak, and H.E. Xu Molecular recognition of parathyroid hormone by its G protein-coupled receptor Proc. Natl Acad. Sci. U.S.A. 105 2008 5034 5039 (Pubitemid 351738505)
30. G. Gololobov, Y. Noda, S. Sherman, I. Rubinstein, J. Baranowska- Kortylewicz, and S. Paul Stabilization of vasoactive intestinal peptide by lipids J. Pharmacol. Exp. Ther. 285 1998 753 758 (Pubitemid 28237458)
31. Y.V. Tan, A. Couvineau, S. Murail, E. Ceraudo, J.M. Neumann, J.J. Lacapere, and M. Laburthe Peptide agonist docking in the N-terminal ectodomain of a class II G protein-coupled receptor, the VPAC1 receptor. Photoaffinity, NMR, and molecular modeling J. Biol. Chem. 281 2006 12792 12798 (Pubitemid 43855371)
32. T. Tenno, N. Goda, Y. Tateishi, H. Tochio, M. Mishima, H. Hayashi, M. Shirakawa, and H. Hiroaki High-throughput construction method for expression vector of peptides for NMR study suited for isotopic labeling Protein Eng. Des. Sel. 17 2004 305 314 (Pubitemid 39093510)
33. D. Neri, T. Szyperski, G. Otting, H. Senn, and K. Wuthrich Stereospecific nuclear magnetic resonance assignments of the methyl groups of valine and leucine in the DNA-binding domain of the 434 repressor by biosynthetically directed fractional 13C labeling Biochemistry 28 1989 7510 7516 (Pubitemid 19238098)
34. L.E. Kay, P. Keifer, and T. Saarinen Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity J. Am. Chem. Soc. 114 1992 10663 10665
35. F. Delaglio, S. Grzesiek, G.W. Vuister, G. Zhu, J. Pfeifer, and A. Bax NMRPipe: a multidimensional spectral processing system based on UNIX pipes J. Biomol. NMR 6 1995 277 293
36. T. Herrmann, P. Guntert, and K. Wuthrich Protein NMR structure determination with automated NOE assignment using the new software CANDID and the torsion angle dynamics algorithm DYANA J. Mol. Biol. 319 2002 209 227 (Pubitemid 34729497)
37. P. Guntert Automated NMR protein structure calculation Prog. Nucl. Magn. Reson. Spectrosc. 43 2003 105 125
38. T. D. Goddard, D. G. Kneller, Sparky 3. San Francisco: University of California.
39. G. Cornilescu, F. Delaglio, and A. Bax Protein backbone angle restraints from searching a database for chemical shift and sequence homology J. Biomol. NMR 13 1999 289 302 (Pubitemid 29143535)
40. J. Fahrenkrug, B. Ottesen, and C. Palle Non-amidated forms of VIP (glycine-extended VIP and VIP-free acid) have full bioactivity on smooth muscle Regul. Pept. 26 1989 235 239 (Pubitemid 20015730)
41. J. Cavanagh, W.J. Fairbrother III, A.G. Palmer, M. Rance, and N.J. Skelton Protein NMR Spectroscopy: Principles and Practice 2nd Ed 2007 Academic Press San Diego 535 673
42. F. Chevalier, J. Lopez-Prados, P. Groves, S. Perez, M. Martin-Lomas, and P.M. Nieto Structure and dynamics of the conserved protein GPI anchor core inserted into detergent micelles Glycobiology 16 2006 969 980 (Pubitemid 44390938)
43. P. Nicole, L. Lins, C. Rouyer-Fessard, C. Drouot, P. Fulcrand, A. Thomas, A. Couvineau, J. Martinez, R. Brasseur, and M. Laburthe Identification of key residues for interaction of vasoactive intestinal peptide with human VPAC1 and VPAC2 receptors and development of a highly selective VPAC1 receptor agonist. Alanine scanning and molecular modeling of the peptide J. Biol. Chem. 275 2000 24003 24012 (Pubitemid 30624691)
44. N. Komi, K. Okawa, Y. Tateishi, M. Shirakawa, T. Fujiwara, and H. Akutsu Structural analysis of pituitary adenylate cyclase-activating polypeptides bound to phospholipid membranes by magic angle spinning solid-state NMR Biochim. Biophys. Acta 1768 2007 3001 3011 (Pubitemid 350236101)
45. S.R.J. Hoare Mechanisms of peptide and nonpeptide ligand binding to Class B G-protein-coupled receptors Drug Discov. Today 10 2005 417 427 (Pubitemid 40450272)
46. M. O'Donnell, R.J. Garippa, N.C. O'Neill, D.R. Bolin, and J.M. Cottrell Structure-activity studies of vasoactive intestinal polypeptide J. Biol. Chem. 266 1991 6389 6392 (Pubitemid 21906230)
47. H. Igarashi, T. Ito, W. Hou, S.A. Mantey, T.K. Pradhan, C.D. Ulrich, S.J. Hocart, D.H. Coy, and R.T. Jensen Elucidation of vasoactive intestinal peptide pharmacophore for VPAC(1) receptors in human, rat, and guinea pig J. Pharmacol. Exp. Ther. 301 2002 37 50 (Pubitemid 34250277)
48. H. Igarashi, T. Ito, S.A. Mantey, T.K. Pradhan, W. Hou, D.H. Coy, and R.T. Jensen Development of simplified vasoactive intestinal peptide analogs with receptor selectivity and stability for human vasoactive intestinal peptide/pituitary adenylate cyclase-activating polypeptide receptors J. Pharmacol. Exp. Ther. 315 2005 370 381 (Pubitemid 41380533)
49. E. Ceraudo, S. Murail, Y.V. Tan, J.J. Lacapere, J.M. Neumann, A. Couvineau, and M. Laburthe The vasoactive intestinal peptide (VIP) alpha-helix up to C terminus interacts with the N-terminal ectodomain of the human VIP/Pituitary adenylate cyclase-activating peptide 1 receptor: photoaffinity, molecular modeling, and dynamics Mol. Endocrinol. 22 2008 147 155