Bradykinin antagonists with dehydrophenylalanine analogues at postion 5

Journal of Peptide Science

Volumn 4, Issue 2, 1998, Pages 92-100

  Greiner, Georg ^a   Dornberger, Utz ^a   Paegelow, Inge ^b   Schölkens, Bernward A ^c   Liebmann, Claus ^a   Reissmann, Siegmund ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

^c SANOFI   (France)

Author keywords

Antagonists; Bradykinin; Dehydrophenylalanine; Radio ligand binding studies; Smooth muscle contraction

Indexed keywords

CAVIA PORCELLUS; SUS SCROFA;

BRADYKININ; BRADYKININ B2 RECEPTOR; BRADYKININ RECEPTOR; DEHYDROPHENYLALANINE; DRUG DERIVATIVE; FLUORINE DERIVATIVE; MEMBRANE PROTEIN; PHENYLALANINE;

ANIMAL; ARTICLE; BINDING COMPETITION; BINDING SITE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; FEMALE; GUINEA PIG; ILEUM; MALE; METABOLISM; PHYSIOLOGY; RAT; UTERUS; VASCULAR SMOOTH MUSCLE;

ANIMALS; BINDING SITES; BINDING, COMPETITIVE; BRADYKININ; FEMALE; FLUORINE COMPOUNDS; GUINEA PIGS; ILEUM; MALE; MEMBRANE PROTEINS; MUSCLE, SMOOTH, VASCULAR; PHENYLALANINE; RATS; RECEPTOR, BRADYKININ B2; RECEPTORS, BRADYKININ; UTERUS;

EID: 0032037287     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-1387(199804)4:2<92::aid-psc131>3.0.co;2-8     Document Type: Article

References (33)

1. R. J. Vavrek and J. M. Stewart (1985). Competitive antagonists of bradykinin. Peptides 6, 161-164.
2. J. M. Stewart (1995). Bradykinin antagonists: Development and applications. Biopolym. (Peptide Sci.) 37, 143-155.
3. 2 receptor antagonists. Bioorg. Med. Chem. Lett. 5, 357-362.
4. 2 receptor antagonist. Pharmacology 91, 4693-4697.
5. S. Chakravarty, D. Wilkins and D. J. Kyle (1993). Design of potent, cyclic peptide bradykinin receptor antagonists from conformationally constrained linear peptides. J. Med. Chem. 36, 2569-2571.
6. W. Guba, R. Haeßner, J. Knolle and H. Kessler (1995). A novel combined approach of NMR and molecular dynamics within a biphasic membran mimetic-conformation and orientation of the bradykinin antagonist Hoe 140. J. Am. Chem. Soc. 116, 7532-7540.
7. 2 receptor and its utility for drug design. J. Med. Chem. 37, 1347-1354.
8. A. Otter, P. Bigler, J. M. Stewart and G. Kotovych (1993). A proton magnetic resonance study of two synthetic agonist-antagonist pairs of bradykinin analogues. Biopolymers 33, 769-780.
9. L. Seyfarth, L. F. Pineda De Castro, I. Liepina, I. Paegelow, C. Liebmann and S. Reissman (1995). New cyclic bradykinin antagonists containing dsulfide and lactam bridges at the N-terminal sequence. Int. J. Peptide Protein Res. 46, 155-165.
10. J. K. Young and R. P. Hicks (1994). NMR and molecular modeling investigations of the neuropeptide bradykinin in three different solvent systems: DMSO, 9:1 dioxane/water, and in the presence of 7.4 mM lysophosphatidylcholine micelles. Biopolymers 34, 611-623.
11. 6-bradykinin: Molecular dynamics simulations in a biphasic membrane mimetic. J. Med. Chem. 40, 99-104.
12. S. Reissmann, G. Greiner, C. Schwuchow, L. F. Pineda De Castro and C. Liebmann (1993). In: Chemistry of Peptides and Proteins, D. Brandenburg, V. Ivanov and W. Voelter, Eds., p. 377-388, DWI Reports, Aachen.
13. S. Reissmann, C. Schwuchow, L. Seyfarth, L. F. Pineda De Castro, C. Liebmann, I. Paegelow, H. Werner and J. M. Stewart (1996). Highly selective bradykinin agonists and antagonists with replacement of proline residues by D- and L-N-methylphenylalanine. J. Med. Chem. 39, 929-936.
14. S. Reissmann, G. Greiner, L. Seyfarth, I. Paegelow, H. Werner, G. Vietinghoff, S. Boeckmann, E. Schultz, U. Wartner and L. Gera (1996). A new type of bradykinin antagonists: Analogues with N-alkyl amino acids in position 2. Immunopharmacology 33, 73-80.
15. I. Paegelow, H. Werner and S. Reissmann (1995). Effects of bradykinin and bradykinin analogues on spleen cells of mice. Eur. J. Pharmacol. 279, 211-216.
16. J. Porter, J. Dykert and J. Rivier (1987). Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans. Int. J. Peptide Protein Res. 30, 13-21.
17. D. J. Phelps and F. C. A. Gaeta (1982). A convenient synthesis of glycyl-(β-aryl)-dehydroalanines. Synthesis 1982, 234-235.
18. H. O. Schild (1942). A method of conducting a biological assay on a preparation giving repeated graded responses illustrated by the estimation of histamine. J. Physiol. 101, 115.
19. J. M. van Rossum, J. A. Th. M. van Hurkmans and C. J. J. Wolters (1963). Cumulative dose-response curves. II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters. Arch. Int. Pharmacodyn. 143, 299-330.
20. F. J. Hock, K. Wirth, U. Albus, W. Linz, H. J. Gerhards, G. Wiemer, St. Henke, G. Breipohl, W. König, J. Knolle and B. A. Schölkens (1991). Hoe 140 a new potent and long acting bradykinin antagonist: In vitro studies. Br. J. Pharmacol. 102, 769-773.
21. 2 receptor antagonist. Hoe 140, in the rat uterus. Eur. J. Pharmacol. 235, 183-188.
22. H. J. Tobler and G. Engel (1983). Affinity spectra: A novel way for the evaluation of equilibrium binding experiments. Naunyn-Schmiedeberg's Arch. Pharmacol. 322, 183-192.
23. G. H. Fisher, P. Berryer, J. W. Ryan, V. Chauhan and C. H. Stammer (1981). Dehydrophenylalanyl analogues of bradykinin: Synthesis and biological activities. Arch. Biochem. Biophys. 211, 269-275.
24. G. Vietinghoff, I. Paegelow and S. Reissmann (1996). Induction of histamine release from rat mast cells by bradykinin analogues. Peptides 17, 1467-1470.
25. 1-family. Biochem. Biophys. Res. Commun. 167, 910-917.
26. 2 receptor subtypes in guinea pig ileum smooth muscle membranes with a selective, iodinatable, bradykinin analogue. Mol. Pharmacol. 46, 949-956.
27. R. W. Ransom, C. B. Goodman and G. S. Young (1992). Bradykinin stimulation of phosphoinositide hydrolysis in guinea-pig ileum longitudinal muscle. Br. J. Pharmacol. 105, 919-924.
28. 2 receptor. Eur. J. Pharmacol. 288, 35-43.
29. C. Liebmann and S. Reissmann (1990). Bradykinin inhibits rat myocetrial adenylate cyclase activity via a high-affinity receptor. Biomed. Biochim. Acta. 49, 1231-1234.
30. J. M. Stewart and D. W. Woolley (1966). In: Hypotensive Peptides., E. G. Erdös, N. Back and F. Sicuteri, Eds., p. 23-31, Springer, Berlin.
31. R. Jain and V. S. Chauhan (1996). Conformatlonal characteristics of peptides containing α,β-dehydroamino acid residues. Biopolym. (Peptide Sci.) 40, 105-119.
32. G. Pietrzyński, B. Rzeszotarska, E. Cizak and M. Lisowski (1994). Turn tendency of model α,β-dehydropeptides. Polish J. Chem. 68, 1015-1021.
33. G. H. Fisher, J. W. Ryan and P. Berryer (1977). Biologically active bradykinin analogues containing p-fluorophenylalanine. Cardiovas. Med. 2, 1179-1181.