Comparison of the solution structures of angiotensin I & II implication for structure-function relationship

European Journal of Biochemistry

Volumn 270, Issue 10, 2003, Pages 2163-2173

  Spyroulias, Georgios A ^a   Nikolakopoulou, Panagiota ^a   Tzakos, Andreas ^b   Gerothanassis, Ioannis P ^b   Magafa, Vassiliki ^a   Manessi Zoupa, Evy ^a   Cordopatis, Paul ^a  

^a UNIVERSITY OF PATRAS   (Greece)

^b UNIVERSITY OF IOANNINA   (Greece)

Author keywords

Angiotensin; NMR; Renin angiotensin system; Solid phase peptide synthesis; Solution structure

Indexed keywords

ANGIOTENSIN; ANGIOTENSIN 1 RECEPTOR; ANGIOTENSIN I; DIMETHYL SULFOXIDE; HISTIDINE; LEUCINE; TRIFLUOROETHANOL; WATER;

AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; CARBOXY TERMINAL SEQUENCE; COUPLING CONSTANT; ENERGY; HYDROPHOBICITY; INTERMETHOD COMPARISON; NUCLEAR OVERHAUSER EFFECT; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN FUNCTION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; RESTRAINED ENERGY MINIMIZATION; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANGIOTENSIN I; ANGIOTENSIN II; DIMETHYL SULFOXIDE; FREE RADICAL SCAVENGERS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDE BIOSYNTHESIS; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; PROTONS; RENIN-ANGIOTENSIN SYSTEM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037517107     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2003.03573.x     Document Type: Article

References (66)

1. Do, Y.S., Shinagawa, T., Tam, H., Inagami, T. & Hseuh, W. (1987) Characterization of pure human renal renin. Evidence for a subunit structure. J. Biol. Chem. 262, 1037-1043.
2. Reid, I. (1985) The renin-angiotensin system and body function. Arch. Int. Med. 145, 1475-1479.
3. Regoli, D., Park, W.K. & Rioux, F. (1974) Pharmacology of angiotensin. Pharmacol. Rev. 26, 69-123.
4. Kholsa, M.C., Smeby, R.R. & Bumepus, F.M. (1974) Structure-activity relationship in angiotensin II analogs. In Handbook Exp. Pharmacol. - Angiotensin (Page, I.H. & Bumpus, F.M., eds), pp. 126-161. Springer-Verlag, Berlin.
5. Cordopatis, P., Theodoropoulos, D. & Escher, E. (1999) A Course of structure-function studies in a series of angiotensin II Agonists. In Bioactive Peptides in Drug Discovery and Design. Medical Aspects (Matsoukas, J. & Mavromoustakos, T., eds), pp. 25-32. IOS Press, Amsterdam, NL.
6. De Coen, J.L. & Ralston, E. (1977) Theoretical conformational analysis of Asnl, Val5 angiotensin II. Biopolymers 16, 1929-1943.
7. Rauk, A., Hamilton, G. & Moore, G.J. (1987) Mechanistic consequences of charge transfer systems in serine proteases and angiotensin: semiempirical computations. Biochem. Biophys. Res. Commun. 145, 1349-1355.
8. Printz, M.P., Nemethy, G. & Bleich, H. (1972) Proposed models for angiotensin II in aqueous solution and conclusions about receptor topography. Nat. New Biol. 237, 135-140.
9. Fermandjian, S., Sakarellos, C., Piriou, F., Juy, M., Toma, F., Thanh, H.L., Lintner, K., Khosla, M.C., Smeby, R.R. & Bumpus, F.M. (1983) The key role of residue 5 in angiotensin II. Biopolymers 22, 227-231.
10. Weinkam, R.J. & Jorgensen, E.C. (1971) Angiotensin II analogs. 8. The use of free radical containing peptides to indicate the conformation of the carboxyl terminal region of angiotensin II. J. Am. Chem. Soc. 93, 7033-7038.
11. Weinkam, R.J. & Jorgensen, E.C. (1971) Angiotensin II analogs. IX. Conformational studies of angiotensin II by proton magnetic resonance. J. Am. Chem. Soc. 93, 7038-7044.
12. Liakopoulou-Kyriakides, M. & Galardy, R.E. (1979) s-Cis and s-tram isomerism of the His-Pro peptide bond in angiotensin and thyroliberin analogues. Biochemistry 18, 1952-1957.
13. Deslauriers, R., Paiva, A.C., Schaumburg, K. & Smith, I.C. (1975) Conformational flexibility of angiotensin II. A carbon-13 spin-lattice relaxation study. Biochemistry 14, 878-886.
14. Sakarellos, C., Lintner, K., Piriou, F. & Fermandjian, S. (1983) Conformation of the central sequence of angiotensin II and analogs. Biopolymers 22, 663-687.
15. Fermandjian, S., Morgat, J.L., Formageot, P., Legreussus, C. & Meyer, P. (1972) Angiotensin II conformations. Infrared and Raman studies. Eur. J. Biochem. 28, 174-182.
16. 1]angiotensin II conformation by nuclear Overhauser effect spectroscopy in the rotating frame (ROESY): clustering of the aromatic rings in dimethylsulfoxide. Peptides 11, 359-366.
17. Krimm, S. & Bandekar, J. (1986) Vibrational spectroscopy and conformation ofpeptides, polypeptides, and proteins. Adv. Protein Chem. 38, 181-364.
18. Byler, D.M. & Susi, H. (1986) Examination of the secondary structure of proteins by deconvolved FTIR spectra. Biopolymers 25, 469-487.
19. Printz, M.P., Williams, H.P. & Craig, L.C. (1972) Evidence for the presence of hydrogen-bonded secondary structure in angiotensin II in aqueous solution. Proc. Natl Acad. Sci. USA 69, 378-382.
20. Moore, G.J. (1985) Kinetics of acetylation-deacetylation of angiotensin II. Intramolecular interactions of the tyrosine and histidine side-chains. Int. J. Pept. Protein Res. 26, 469-481.
21. Moore, G.J. & Matsoukas, J.M. (1985) Angiotensin as a model for hormone-receptor interactions. Biosci. Report 5, 407-416.
22. Kataoka, T., Beusen, D.D., Clark, J.D., Yodo, M. & Marshall, G.R. (1992) The utility of side-chain cyclization in determining the receptor-bound conformation of peptides: cyclic tripeptides and angiotensin II. Biopolymers 32, 1519-1533.
23. 1]angiotensin II on conformation and activity. NMR evidence for aromatic ring clustering and peptide backbone folding compared with [des-1,2,3]angiotensin II. J. Biol. Chem. 269, 5303-5312.
24. Cordopatis, P., Manessi-Zoupa, E., Theodoropoulos, D., Bosse, R., Bouley, R., Gagnon, S. & Escher, E. (1994) Methylation in positions 1 and 7 of angiotensin II. A structure-activity relationship study. Int. J. Pept. Protein Res. 44, 320-324.
25. Joseph, M.-P., Maigret, B. & Scheraga, H.A. (1995) Proposals for the angiotensin II receptor-bound conformation by comparative computer modeling of AII and cyclic analogs. Int. J. Pept. Protein Res. 46, 514-526.
26. Barlos, K., Gatos, D., Kallitsis, J., Papaphotiou, G., Sotiriou, P., Wenquing, Y. & Shafer, W. (1989) Darstellung geshützter peptidfragmente unter einsatz substituierter triphenylmethyl-harze. Tetrahedron Lett. 30, 3943-3946.
27. Carpino, L.A. & Han, G.Y. (1972) The 9-fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 37, 3404-3409.
28. Piantini, U., Sorensen, O.W. & Ernst, R.R. (1982) Multiple quantum filters for elucidating NMR coupling networks. J. Am. Chem. Soc. 104, 6800-6801.
29. Bax, A. & Davis, D.G. (1985) MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 65, 355-360.
30. Palmer, A.G. III, Cavanagh, J., Wright, P.E. & Rance, M. (1991) Sensitivity improvement in proton-detected two-dimensional heteronuclear correlation NMR spectroscopy. J. Magn. Reson. 93, 151-170.
31. 1H spin-spin coupling constants in proteins. Biochem. Biophys. Res. Commun. 113, 967-974.
32. Jeener, J., Meier, B.H., Bachmann, P. & Ernst, R.R. (1979) Investigation of exchange processes by two-dimensional NMR spectroscopy. J. Chem. Phys. 71, 4546-4553.
33. Macura, S., Wüthrich, K. & Ernst, R.R. (1982) The relevance of J cross-peaks in two-dimensional NOE experiments of macromolecules. J. Magn. Reson. 47, 351-357.
34. Eccles, C., Güntert, P., Billeter, M. & Wüthrich, K. (1991) Efficient analysis of protein 2D NMR spectra using the software package EASY. J. Biomol. NMR 1, 111-130.
35. Güntert, P., Braun, W. & Wüthrich, K. (1991) Efficient computation of three-dimensional protein structures in solution from nuclear magnetic resonance data using the program DIANA and the supporting programs CALIBA, HABAS and GLOMSA. J. Mol. Biol. 217, 517-530.
36. Wüthrich, K. (1986) NMR of Proteins and Nucleic Acids. Wiley, New York.
37. Wüthrich, K., Billeter, M. & Brown, W. (1983) Pseudo-structures for the, 20 common amino acids for use in studies of protein conformations by measurements of intramolecular proton-proton distance constraints with nuclear magnetic resonance. J. Mol. Biol. 169, 949-961.
38. Güntert, P., Mumenthaler, C. & Wüthrich, K. (1997) Torsion angle dynamics for NMR structure calculation with the new program DYANA. J. Mol. Biol. 273, 283-298.
39. Pearlman, D.A., Case, D.A., Caldwell, J.W., Ross, W.S., Cheatham, T.E., Ferguson, D.M., Seibel, G.L., Singh, U.C., Weiner, P.K. & Kollman, P.A. (1997) AMBER 5.0. University of California, San Francisco.
40. Pearlman, D.A., Case, D.A., Caldwell, G.C., Siebel, G.L., Singh, U.C., Weiner, P. & Kollman, P.A. (1991) AMBER 4.0. University of California, San Francisco.
41. Koradi, R., Billeter, M. & Wüthrich, K. (1996) MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graph. 14, 51-55.
42. Perodin, J., Bouley, R., Escher, E., Assimomytis, N., Magafa, V., Manessi-Zoupa, E., Theodoropoulos, D. & Cordopatis, P. (2000) Angiotensin II analogues with sulphur-containing side-chains in position 5. A structure-activity relationship study. Arzneimittelforschung 50, 526-529.
43. Mavromoustakos, T., Kolocouris, A., Zervou, M., Roumelioti, P., Matsoukas, J. & Weisemann, R. (1999) An effort to understand the molecular basis of hypertension through the study of conformational analysis of losartan and sarmesin using a combination of nuclear magnetic resonance spectroscopy and theoretical calculations. J. Med. Chem. 42, 1714-1722.
44. Iyer, S.N., Ferrario, C.M. & Chappell, M.C. (1998) Angiotensin-(1-7) contributes to the antihypertensive effects of blockade of the renin-angiotensin system. Hypertension 31, 356-361.
45. Matsoukas, J.M., Polevaya, L., Ancans, J., Mavromoustakos, T., Kolocouris, A., Roumelioti, P., Vlahakos, D.V., Yamdagni, R., Wu, Q. & Moore, G.J. (2000) The design and synthesis of a potent angiotensin II cyclic analogue confirms the ring cluster receptor conformation of the hormone angiotensin II. Bioorg. Med. Chem. 8, 1-10.
46. Roumelioti, P., Tselios, T., Alexopoulos, K., Mavromoustakos, T., Kolocouris, A., Moore, G.J. & Matsoukas, J.M. (2000) Structural comparison between type I and type II antagonists: possible implications in the drug design of AT1 antagonists. Bioorg. Med. Chem. Lett. 10, 755-758.
47. 1H-NMR conformational studies in water of angiotensin II analogues modified at the N- and C-termini: Interactions of the aromatic side chains and folding of the N-terminal domain. Collect. Czech. Chem. Commun. 59, 2523-2532.
48. 8]ANG II for receptor blockade. Int. J. Pept. Protein Res. 38, 1-7.
49. Matsoukas, J.M., Goghari, M.H., Scanlon, M.N., Franklin, K.J. & Moore, G.J. (1985) Synthesis and biological activities of analogues of angiotensins II and III containing O-methyltyrosine and D-tryptophan. J. Med. Chem. 28, 780-783.
50. Matsoukas, J.M., Scanlon, M.N. & Moore, G.J. (1984) A cyclic angiotensin antagonist: [1,8-cysteine]angiotensin II. J. Med. Chem. 27, 404-406.
51. Shin, Y.A. & Yoo, S.-E. (1996) Conformational study of angiotensin II. Biopolymers 38, 183-190.
52. Nikiforovich, G.V. & Marshall, G.R. (1993) Three-dimensional recognition requirements for angiotensin agonists: a novel solution for an old problem. Biochem. Biophys. Res. Commun. 195, 222-228.
53. Nikiforovich, G.V., Kao, J.L.-F., Plucinska, K., Zhang, W.J. & Marshall, G.R. (1994) Conformational analysis of two cyclic analogs of angiotensin: Implications for the biologically active conformation. Biochemistry 33, 3591-3598.
54. Scanlon, M.N., Matsoukas, J.M., Franklin, K.J. & Moore, G.J. (1984) A new approach to angiotensin antagonists: methylation of the tyrosine hydroxyl in angiotensin II. Life Sci. 34, 317-321.
55. Samanen, J., Brandeis, E., Narindray, D., Adams, W., Cash, T., Yellin, T. & Regoli, D. (1988) The importance of residues 2 (arginine) and 6 (histidine) in high-affinity angiotensin II antagonists. J. Med. Chem. 31, 737-741.
56. Carpenter, K.A., Wilkes, B.C. & Schiller, P.W. (1998) The octapeptide angiotensin II adopts a well-defined structure in a phospholipid environment. Eur. J. Biochem. 251, 448-453.
57. Garcia, K.C., Ronco, P.M., Verroust, P.J., Brünger, A.T. & Amzel, L.M. (1992) Three-dimensional structure of an angiotensin II-Fab complex at 3 Å: hormone recognition by an anti-idiotypic antibody. Science 257, 502-507.
58. Boucard, A.A., Wilkes, B.C., Laporte, S.A., Escher, E., Guillemente, G. & Leduc, R. (2000) Photolabeling identifies position 172 of the human AT1 receptor as a ligand contact point: receptor-bound angiotensin II adopts an extended structure. Biochemistry 39, 9662-9670.
59. 1). J. Biol. Chem. 270, 14024-14030.
60. Inoue, Y., Nakamura, N. & Inagami, T. (1997) A review of mutagenesis studies of angiotensin II type 1 receptor, the three-dimensional receptor model in search of the agonist and antagonist binding site and the hypothesis of a receptor activation mechanism. J. Hypertens. 15, 703-714.
61. 1 receptor are not involved in ligand binding but participate in signal transduction. Mol. Endo. 12, 810-814.
62. Feng, Y.H., Noda, K., Saad, Y., Liu, X.P., Husain, A. & Kamik, S.S. (1995) The docking of Arg2 of angiotensin II with Asp281 of AT1 receptor is essential for full agonism. J. Biol. Chem. 270, 12846-12850.
63. Gerothanassis, I.P., Birlirakis, N., Karayannis, T., Tsikaris, V., Sakarellos-Daitsiotis, M., Sakarellos, C., Vitoux, B. & Marraud, M. (1992) 17O NMR and FT-IR study of the ionization state of peptides in aprotic solvents - Application to Leu-enkephalin. FEBS Lett. 298, 188-190.
64. Zhang, W.-J., Nikiforovich, G.V., Pérodin, J., Richard, D.E., Escher, E. & Marshall, G.R. (1996) Novel cyclic analogs of angiotensin II with cyclization between positions 5 and 7: conformational and biological implications. J. Med. Chem. 39, 2738-2744.
65. Pierson, M.E. & Freer, R.J. (1992) Analysis of the active conformation of angiotensin II: a comparison of AII and non-peptide AII antagonists. Pept. Res. 5, 102-105.
66. Noda, K., Saad, Y. & Karnik, S.S. (1995) Interaction of Phe8 of angiotensin II with Lys199 and His256 of AT1 receptor in agonist activation. J. Biol. Chem. 270, 28511-28514.