New bradykinin analogues modified in the C-terminal part with sterically restricted 1-aminocyclohexane-1-carboxylic acid

Journal of Medicinal Chemistry

Volumn 48, Issue 25, 2005, Pages 8055-8059

  Labudda Dawidowska, Olga ^a   Wierzba, Tomasz H ^b   Prahl, Adam ^a   Kowalczyk, Wioleta ^a   Gawiński, Łukasz ^b   Plackova, Marketa ^c   Slaninová, Jiřina ^c   Lammek, Bernard ^a  

^a UNIVERSITY OF GDA SK   (Poland)

^b MEDICAL UNIVERSITY OF GDANSK   (Poland)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

1 ADAMANTANEACETIC ACID; 1 AMINOCYCLOHEXANECARBOXYLIC ACID; ADAMANTANE DERIVATIVE; BRADYKININ B2 RECEPTOR ANTAGONIST; BRADYKININ DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXYLAMINE DERIVATIVE; ENALAPRIL; UNCLASSIFIED DRUG; UTEROTONIC AGENT;

ACYLATION; AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANXIETY DISORDER; ARTICLE; BRADYCARDIA; CONTROLLED STUDY; DRUG DETERMINATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FEMALE; HEART ARREST; HEART RATE; MALE; MEAN ARTERIAL PRESSURE; NONHUMAN; PEPTIDE SYNTHESIS; RAT; SEIZURE; SNIFFING; SOLID PHASE SYNTHESIS; STEREOSPECIFICITY; UTERUS CONTRACTILITY;

ACETIC ACIDS; ADAMANTANE; AMINO ACIDS, CYCLIC; ANIMALS; BLOOD PRESSURE; BRADYKININ; CYCLOHEXANECARBOXYLIC ACIDS; FEMALE; MALE; RATS; RATS, WISTAR; RECEPTOR, BRADYKININ B2; STRUCTURE-ACTIVITY RELATIONSHIP; UTERINE CONTRACTION;

EID: 29144454528     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0580353     Document Type: Article

References (27)

1. Bathon, J. M.; Proud, D. Bradykinin antagonists. Annu. Rev. Pharmacol. Toxicol. 1991, 31, 129-162.
2. Burgess, G. M.; Perkins, M. N.; Rang, H. P.; Campbell, E. A.; Brown, M. C.; McIntyre, P.; Urban, L.; Dziadulewicz, E. K.; Ritchie, T. J.; Hallett, A.; Snell, C. R.; Wrigglesworth, R.; Lee, W.; Davis, C.; Phagoo, S. B.; Davis A. J.; Phillips, E.; Drake, G. S.; Hughes, G. A.; Dunstan, A.; Bloomfield, G. C. Bradyzide, a potent non-peptide B2 bradykinin receptor antagonist with long-lasting oral activity in animal models of inflammatory hyperalgesia. Br. J. Pharmacol. 2000, 129, 77-86.
3. Farmer, S. G.; Burch, R. M. Biochemical and molecular pharmacology of kinin receptors. Annu. Rev. Pharmacol. Toxicol. 1992, 32, 511-536.
4. Hess, J. F.; Borkowski, J. A.; Young, G. S.; Strader, C. D.; Ramsom, R. W. Cloning and pharmacological characterization of a human bradykinin (BK-2) receptor. Biochem. Biophys. Res. Commun. 1992, 184, 260-268.
5. Menke, J. G.; Borkowski, J. A.; Bierilo, K. K.; MacNeil, T.; Derrick, A. W.; Schneck, K. A.; Ransom, R. W.; Strader, C. D.; Linemeyer, D. L.; Hess, J. F. Expresion cloning of a human B1 bradykinin receptor. J. Biol. Chem. 1994, 269, 21583-21586.
6. Barki-Harrington, L.; Daaka, Y. Bradykinin induced mitogenesis of androgen independent prostate cancer cells. J. Urol. 2001, 165, 2121-2125.
7. 2 bradykinin antagonist. In Bradykinin Antagonists. Basic and Clinical Research; Burch, R. M., Ed.; Marcel Dekker Inc.; New York, 1991; pp 51-96.
8. Hock, F. J.; Wirth, K.; Albus, U.; Linz, W.; Gerhards, H. J.; Wiemer, G.; Henke, S.; Breipohl, G.; Konig, W.; Knolle, J.; Scholkens. B. HOE 140, a new potent and long acting bradykinin antagonist. Br. J. Pharmacol. 1991, 102, 769-773.
9. 2-antagonists of brady-kinin. Pol. J. Chem. 1994, 68, 913-920.
10. Jastrzȩbska, B.; Derdowska, I.; Kowalczyk, W.; Machová, A.; Slaninová, J.; Lammek, B. Influence of 1-aminocyclohexane-1-carboxylic acid in position 2 or 3 of AVP and its analogues on their pharmacological properties. J. Pept. Res. 2003, 62, 70-77.
11. Yamada, T.; Iino, M.; Matsuoka, N.; Yanagihara, R.; Miyazawa, T.; Shirasu, N.; Shimohigashi, Y. Synthesis and receptor activity of endomorphin analogs containing α,α-disubstituted glycine. In Peptide Science 1999; Fujii, N., Eds.; The Japanese Peptide Society: Minoh, Japan, 2000; pp 441-444.
12. Schachter, L.; Uchida, Y.; Longridge, D.; Łabȩdź, T.; Whalley, F.; Vavrek, R.; Stewart, J. New synthetic antagonists of bradykinin. Br. J. Pharmacol. 1987, 92, 851.
13. Cloutier, F.; de Sousa Buck, H.; Ongali, B.; Couture, R. Pharmacologic and autoradiographic evidence for an up-regulation of kinin B(2) receptors in the spinal cord of spontaneously hypertensive rats. Br J. Pharmacol. 2002, 13, 1641-1654.
14. Milan, A.; Mulatero, P.; Williams, T. A.; Carra, R.; Schiavone, D.; Martuzzi, R.; Rabbia, F.; Veglio, F. Bradykinin B2 receptor gene (-58T/C) polymorphism influences baroreflex sensitivity in never-treated hypertensive patients. J Hypertens. 2005, 23, 63-69.
15. Gera, L.; Stewart, J. A new class of bradykinin antagonists con taining indanylglycine. Immunopharmacology 1996, 33, 174-177.
16. Prahl, A.; Wierzba, T.; Winklewski, P.; Musiakł, P.; Juzwa, W.; Lammek, B. Antagonists of bradykinin modified with conformationally restricted dipeptide fragment. Pol. J. Chem. 1997, 71, 929-935.
17. Derdowska, I.; Prahl, A.; Neubert, K.; Hartrodt, B.; Trzeciak, H.; Klimanek, M.; Winklewski, P.; Wierzba, T.; Juzwa, W.; Lammek, B. New bradykinin antagonists containing a conformationally restricted dipeptide fragment in their molecules. J. Pept. Res. 2001, 57, 11-18.
18. Lammek, B.; Wang, Y. X.; Gavras, I.; Gavras, H. A novel bradykinin antagonist with improved properties. J. Pharm. Pharmacol. 1991, 43, 887-888.
19. Lammek, B.; Wang, Y. X.; Gawras, I.; Gavras, H. A new highly potent antagonist of bradykinin. Peptides 1990, 11, 1041-1043.
20. Odya, C. E.; Goodfriend, T. L.; Pena, C. Bradykinin receptor-like binding studied with iodinated analogues. Biochem. Pharmacol. 1980, 29, 175-185.
21. Plevin, R.; Owen, P. J. Multiple B2 kinin receptors in mammalian tissues. Trends Pharmacol. Sci. 1988, 9, 387-389.
22. Steranka, L. R.; Manning, D. C.; Dehas, C. J.; Ferkany, J. W.; Borosky, S. A.; Connor, J. R.; Vavrek, R. J.; Stewart, J. M.; Shyder, S. H. Bradykinin as a pain mediator: Receptors are localized to sensory neurons have analgesic actions. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 3245-3249.
23. Prahl, A.; Derdowska, I.; Dawidowska, O.; Neubert, K.; Hartrodt, B.; Wierzba, T.; Juzwa, W.; Lammek, B. New bradykinin analogues modified in position 6 and 7 with naphthylalanine. Pol. J. Chem. 2003, 77, 881-887.
24. Wang, S. S. p-Alkoxybenzyl alcohol resin and p- alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 1973, 95, 1328-1333.
25. Holton, P. A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 1948, 3, 328-334.
26. Munsick, R. A. Effect of magnesium ion on the response of the rat uterus to neurohypophysial hormones and analogues. Endocrinology 1960, 66, 451-457.
27. Trzeciak, H. I.; Kozik, W.; Melhem, S.; Kania, A.; Dobrowolski, D.; Prahl, A.; Derdowska, I.; Lammek, B. New bradykinin analogs in contraction of rat uterus. Peptides 2000, 21, 829-834.