| Title | Synthesis and biological activities of angiotensin II analogues containing α-aminoisobutyric acid | |
| Authors | Paul Cordopatis1, Urania Belte1, Evy Manessi-Zoupa2, Dimitrios Theodoropoulos2, Roger Bosse3, Sylvain Gagnon3 and Emanuel Escher3
1. Department of Pharmacy and 2. Department of Chemistry, University of Patras, 265 00 Patra, Greece 3. Department of Pharmacology, University of Sherbrooke, Quebec J1H 5N4, Canada |
|
| Citation | Cordopatis, P., Belte, U., Manessi-Zoupa, E., Theodoropoulos, D., Bosse, R. et al.: Synthesis and biological activities of angiotensin II analogues containing α-aminoisobutyric acid, Epitheorese Klin. Farmakol. Farmakokinet. 9(2-3): 89-92 (1995) | |
| Publication Date | 1995 | |
| Full Text Language | English | |
| Order – Buy | Ηλεκτρονική Μορφή: pdf (10 €) – Digital Type: pdf (10 €)
pharmakonpress[at]pharmakonpress[.]gr |
|
| Keywords | Peptide synthesis, angiotensin II, α-aminoisobutyric acid analogues. | |
| Other Terms | review article | |
| Summary | Six analogues of angiotensin II (AT) were synthesized with modifications in position 1 and 7. Previous studies indicate that α,α dimethylation of Gly1 (aminoisobutyric acid, Aib) produced quite potent analogues, as did N-methylation of Gly1 (sarcosine). Combination of both, Cα and Nα méthylations to N-Me-Aib1 reduces, however, affinity in a drastic manner. Décyclisation of the Pro7-residue produced moderately active analogues with position 7N-methylation and inactive analogues if the N-alkylation was su-pressed. In order to investigate a possible interdependence of positions 1 and 7, a series of peptides with combinations of position 1 and 7 alkylations were investigated. The following analogues were prepared by solid phase synthesis: [Sar¹, Aib7]AT, [Sar1, Aib7, Leu8]AT, [Aib1,7 ]AT, [Aib1,7,Leu8]AT, [N-Me-Aib1,7, Leu8]AT. The biological properties of these peptides were assessed on the rabbit aorta preparation and their binding potencies were measured on bovine adrenal membranes. Both on agonistic and antagonistic analogues single Aib substitutions either in position 1 or 7 induced minor affinity modifications in both bioassays. Simultaneous Aib modifications in position 1 and 7 induced severe affinity loss in both bioassays. Agonistic Aib7 analogues have all reduced intrinsic activity, indicating an influence of this position on the activation mechanism of the AT receptor of the AT1 type. | |
| References | 1. IUPAC-IIUB Commission on Biochemical Nomencla-ture: Eur. J. Biochem. 138: 9 (1984)
2. Park, W.K., Choi, C., Rioux, F., Regoli, D.: Can. J. Biochem. 52: 113 (1974) 3. Andretta, R.H., Scheraga, H.A.: J. Med. Chem. 114: 489 (1971) 4. Moore, G.J., Ondeman, E.M., Ko, D., Nystrom, D.M.: J. Med. Chem: 22: 1147 (1979) 5. Smeby, R.R., Fermandjian, S.: In: (B. Weinstein, ed.) Amino Acids, Peptides and Proteins, p. 117, Dekker, New York, 1973 6. Johnson, J.A., Davis, J.O.: Science 179: 906 (1973) 7. Hall, M.M., Khosla, M.C., Khairallah, P.A., Bumpus, F.M.: J. Pharmacol. Exp. Ther. 188: 222 (1974) 8. Galardy, R.E., Stafford, S.S., Schaefer, M.L., Ho, H., La Vorgna, K.A., Jamieson, J.D.: J. Med. Chem. 21: 1279 (1978) 9. Cordopatis P., Belte U., Theodoropoulos, D., Bosse, R., Escher, E.: Col. Czechoslovak Chem. Commun. 53: 2599 (1988) 10. Cordopatis, P., Theodoropoulos, D.: Experientia 39: 106 (1983) 11. Rao, C.P., Nagara] R., Rao, C.N.R., Balaram P.: Biochemistry 19: 425 (1980) 12. Whitebread, S., Meie, M., Kamber, B., de Gasparo, M.: Biochem. Biophys. Res. Commun. 163: 284 (1989) 13. Escher, E„ Nguyen, T.M.D., Regoli, D.: Can. J. Physiol. Pharmacol. 56: 956 (1978) 14. Leduc, R., Bernier, M., Escher, E.: Heiv. Chim. Acta 66: 960 (1983) 15. Hoick, M., Bosse, R., Fischli, W., Gerold, H., Escher, E.: Biochem. Biophys. Res. Commun. 160: 1350 (1989) 16. Chaturvedi, N.C., Park, W.K., Smeby, R.R., Bumpus, F.M.: J. Med. Chem. 13: 177 (1970) 17. Fermandjian, S., Lintner, K., Haar, W., Fromageot, P., Khosla, M.C., Smeby, R.R., Bumpus, F.M.: Pept. Proc. Eur. Pept. Symp. 14th, p. 339, 1976 |
|
| Relative Papers |
Online ISSN 1011-6575
Άρθρα Δημοσιευμένα σε αυτό το Περιοδικό Καταχωρούνται στα:
- Chemical Abstracts
- Elsevier’s Bibliographic Databases: Scopus, EMBASE, EMBiology, Elsevier BIOBASE SCImago Journal and Country Rank Factor
Articles published in this Journal are Indexed or Abstracted in: • Chemical Abstracts • Elsevier’s Bibliographic Databases: Scopus, EMBASE, EMBiology, Elsevier BIOBASE SCImago Journal and Country Rank Factor
Συντακτικη Επιτροπή-Editorial Board
| ΕΤΗΣΙΑ ΣΥΝΔΡΟΜΗ 1995 – ANNUAL SUBSCRIPTION 1995 | |
| Γλώσσα Πλήρους Κειμένου – Full Text Language | Αγγλικά – English |
| Παραγγελία – Αγορά – Order – Buy | Ηλεκτρονική Μορφή: pdf (70 €) – Digital Type: pdf (70 €)
pharmakonpress[at]pharmakonpress[.]gr |
| Έντυπη Μορφή (70 € + έξοδα αποστολής) – Printed Type (70 € + shipping)
pharmakonpress[at]pharmakonpress[.]gr |
|