Insertion of an electronegative sulfur atom in the side chain of position 5 of angiotensin II: Changes in the tachyphylactic properties of the peptide

Journal of Peptide Research

Volumn 53, Issue 6, 1999, Pages 678-681

  Zalcberg, H ^a   Assimomytis, N ^b   Magafa, V ^b   Manessi Zoupa, E ^b   Cordopatis, P ^b   Shimuta, Suma Imura ^a  

^a FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF PATRAS   (Greece)

Author keywords

All analogs; Angiotensin II; Guinea pig ileum; Tachyphylaxis

Indexed keywords

ANGIOTENSIN;

ANIMAL TISSUE; ARTICLE; GUINEA PIG; ILEUM; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONFORMATION; RECEPTOR AFFINITY; TACHYPHYLAXIS;

AMINO ACID SUBSTITUTION; ANGIOTENSIN II; ANIMALS; FEMALE; GUINEA PIGS; ILEUM; MALE; SARCOSINE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR; TACHYPHYLAXIS; VASOCONSTRICTOR AGENTS;

EID: 0033020178     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00086.x     Document Type: Article

References (14)

1. 1. Timmermans, P.B.M.W., Wong, P.C., Chiu, A.T., Herblin, W.F., Benfield, P., Carini, D.J., Lee, D.J., Wexler, R.R., Saye, J.M. & Smith, R.D. (1993) Angiotensin II receptors and angiotensin II receptor antagonists. Pharmacol. Rev. 45, 205-251.
2. 2. Samanen, J. & Regoli, D. (1994) Structure activity relationships of peptide angiotensin II receptor agonists and antagonists. In Medicinal Chemistry, Vol. 2, Angiotensin II Receptors (Ruffolo, R.R. Jr, ed.). CRC Press Inc., Boca Raton, FL, pp. 11-97.
3. 3. Miasiro, N., Oshiro, M.E.M., Paiva, T.B. & Paiva, A.C.M. (1983) Role of the two N-terminal residues of angiotensin II in the production of tachyphylaxis. Eur J. Pharmacol. 87, 397-406.
4. 4. Moore, G.J., Franklin, K.J., Nystrom, D.M. & Goghari, M.H. (1985) Strucuture-desensitization relationships of angiotensin analogues in the rat isolated uterus. Can J. Physiol. Pharmacol. 63, 966-971.
5. 5. Shimuta, S.I., Nakaie, C.R., Paiva, A.C.M., Cordopatis, P. & Theodoropoulos, D. (1989) Changes in residues 1 and 4 of angiotensin II affect differently its agonist and tachyphylactic properties. Naunyn -Schmiedeberg's Arch. Pharmacol. 340, 309-313.
6. 6. Merrifield, R.B. (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Soc. 85, 2149-2154.
7. 7. Paiva, T., Goissis, G., Juliano, L., Miyamoto, M.E. & Paiva, A.C.M. (1974) Angiotensin-like and antagonistic activities of N-terminal modified [8-leucine] angiotensin II peptides. J. Med. Chem. 17, 238-241.
8. 8. Cordopatis, P., Theodoropoulos, D., Guillemette, G. & Escher, E. (1981) Studies on position 1 of angiotensin II: effects of affinity and duration of action from alkyl amide substitution. J. Med. Chem. 14, 209-211.
9. 9. Schwyzer, R. & Turrian, H. (1960) The chemistry and pharmacology of angiotensin. Vitam. Horm. 18, 237-288.
10. 10. Khosla, M.C., Smeby, R.R. & Bumpus, F.M. (1974) Structure-activity relationships in angiotensin II analogs. In Angiotensin (Page, I.H. & Bumpus, F.M., eds.). Springer-Verlag, Berlin, p. 126.
11. 11. Jorgensen, E.C. & Windridge, G.C. (1973) Angiotensin II analogues. 10. Stereochemical factors in the 5 position influencing pessor activity. J. Med. Chem. 16, 467-469.
12. 12. 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.
13. 13. Hunyady, L., Balla, T. & Catt, K.J. (1996) The ligand binding site of the angiotensin AT, receptor. Trends Pharmac. Sci. 17, 135-140.
14. 14. Oshiro, M.E.M., Miasiro, N., Paiva, T.B. & Paiva, A.C.M. (1984) Angiotensin tachyphylaxis in the isolated rabbit aorta. Blood Vessels 21, 72-79.