A New Class of Nonpeptide Bradykinin B2 Receptor Ligand, Incorporating a 4-Aminoquinoline Framework. Identification of a Key Pharmacophore to Determine Species Difference and Agonist/Antagonist Profile

Journal of Medicinal Chemistry

Volumn 47, Issue 10, 2004, Pages 2667-2677

  Sawada, Yuki ^a   Kayakiri, Hiroshi ^a   Abe, Yoshito ^a   Mizutani, Tsuyoshi ^a   Inamura, Noriaki ^a   Asano, Masayuki ^a   Aramori, Ichiro ^a   Hatori, Chie ^a   Oku, Teruo ^a   Tanaka, Hirokazu ^a,b  

^a ASTELLAS PHARMA INC   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BRADYKININ; BRADYKININ B2 RECEPTOR; BRADYKININ B2 RECEPTOR ANTAGONIST; INOSITOL PHOSPHATE; LIGAND;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRONCHOSPASM; CHEMICAL MODIFICATION; CHO CELL; CONTROLLED STUDY; DRUG EFFECT; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GUINEA PIG; HUMAN; MALE; NONHUMAN; PHARMACOPHORE; RECEPTOR AFFINITY; SPECIES DIFFERENCE; STRUCTURE ANALYSIS;

ANIMALS; BRONCHOCONSTRICTION; CHO CELLS; CRICETINAE; GUINEA PIGS; HUMANS; INOSITOL PHOSPHATES; LIGANDS; QUINOLINES; RADIOLIGAND ASSAY; RECEPTOR, BRADYKININ B2; SPECIES SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2342505852     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030326t     Document Type: Article

References (38)

1. Regoli, D.; Barabé J. Pharmacology of Bradykinin and Related Kinins. Pharmacol. Rev. 1980, 32, 1-46.
2. Dray, A.; Perkins, M. Bradykinin and Inflammatory Pain. Trends Neurosci. 1993, 16, 99-104.
3. 2 Bradykinin Receptor. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 7724-7728.
4. 2 Receptor Antagonist, on the Development of Experimental Ulcerative Colitis in Mice. Digestive Diseases & Sciences. 1999, 44, 845-851.
5. Stewart, J. M.; Gera, L.; Chan, D. C.; Whalley, E. T.; Hanson, W. L.; Zuzack, J. S. Potent, Long-Acting Bradykinin Antagonists for a Wide Range of Applications. Can. J. Physiol. Pharmacol. 1997, 75, 719-724.
6. Stewart, J. M.; Gera, L.; Chan, D. C. Dimers of Bradykinin and Substance P Antagonists as Potential Anti-Cancer Drugs. Pep. Sci. 1999, 1, 731-732.
7. Lembeck, F.; Wirth, K.; Winkler, I.; Breipohl, G.; Henke, S.; Knolle, J. EP Patent 0 661 058, 1995.
8. Björck, L.; Sjöbring, U.; Ben, Nasr. A.; Olsen, A.; Herwald, H.; Müller-Esterl, W. WO Patent, 97 44353 1997.
9. Wirth, K. J.; Fink, E.; Rudolphi, K.; Heitsch, H.; Deutschländer, N.; Wiemer, G. Amyloid β-(1-40) Stimulates cyclic GMP Production via Release of Kinins in Primary Cultured Endothelial Cells. Eur. J. Pharmcol. 1999, 382, 27-33.
10. Hock, F. J.; Wirth, K.; Albus, U.; Linz, W.; Gerhards, H. J.; Wiemer, G. ; Henke, S.; Breipohl, G.; König, W.; Knolle, J.; Schölkens, B. A. Hoe 140 a New Potent and Long Acting Bradykinin-Antagonist: In Vitro Studies. Br. J. Pharmacol. 1991, 102, 769-773.
11. Wirth, K.; Hock, F. J.; Albus, U.; Linz, W.; Alpermann, H. G.; Anagnostopoulos, H.; Henke, St.; Breipohl, G.; König, W.; Knolle, J.; Schölkens, B. A. Hoe 140 a New Potent and Long Acting Bradykinin-Antagonist: In Vivo Studies. Br. J. Pharmacol. 1991, 102, 774-777.
12. Cheronis, J. C.; Whalley, E. T.; Nguyen, K. T.; Eubanks, S. R.; Allen, L. G.; Duggan, M., J.; Loy, S.; Bonham, K. A.; Blodgett, J. K. A New Class of Bradykinin Antagonists: Synthesis and In Vitro Activity of Bissuccinimidoalkane Peptide Dimers. J. Med. Chem. 1992, 35, 1563-1572.
13. Kyle, D. J.; Martin, J. A.; Burch, R. M.; Carter, J. P.; Lu, S.; Meeker, S.; Prosser, J. C.; Sullivan, J. P.; Togo, J.; Noronha-Blob, L.; Sinsko, J. A.; Walters, R. F.; Whaley, L. W.; Hiner, R. N. Proving the bradykinin receptor: Mapping the Geometric Topography Using Ethers of Hydroxyproline in Novel Peptides. J. Med. Chem. 1991, 34, 2649-2653.
14. Kyle, D. J. Structure-Based Drug Design: Progress toward the Discovery of the Elusive Bradykinin Receptor Antagonists. Curr. Pharm. Des. 1995, 1, 233-254.
15. 2 Receptor. J. Med. Chem. 1993, 36, 2583-2584.
16. 2 Receptor Antagonist. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4693-4697.
17. Gobeil, F.; Pheng, L. H.; Badini, I.; Nguyen-Le, X. K.; Pizard, A.; Rizzi, A.; Blouin, D.; Regoli, D. Receptors for Kinins in the Human Isolated Umbilical Vein. Br. J. Pharmacol. 1996, 118, 289-294.
18. Inamura, N. Presented at Peptide Receptors, Montreal, Canada, 1996.
19. 2 Receptor Antagonist. 1. Construction of the Basic Framework J. Med. Chem. 1998, 41, 564-578.
20. 2 Receptor Antagonists. 2. Overcoming the Species Difference between Guinea Pig and Man. J. Med. Chem. 1998, 41, 4053-4061.
21. 2 Receptor Antagonists. 3. Discovering Bioisosteres of the Imidazo[1,2-a]pyridine Moiety. J. Med. Chem. 1998, 41, 4062-4079.
22. 2 Receptor Antagonists. 4. Discovery of Novel Frameworks Mimicking the Active Conformation. J. Med. Chem. 1998, 41, 4087-4098.
23. 2 Receptor Antagonist, FR167344. Eur. J. Pharmacol. 1997, 333, 79-86.
24. Aramori, I.; Zenkoh, J.; Morikawa, N.; O'donnell, N.; Asano, M.; Nakamura, K.; Iwami, M.; Kojo, H.; Notsu, Y. Novel Subtype-Selective Nonpeptide Bradykinin Receptor Antagonists FR167344 and FR173657. Mol. Pharmacol. 1997, 51, 171-176.
25. 2 Receptor Antagonist, FR173657. Br. J. Pharmacol. 1997, 120, 617-624.
26. Charkravarty, S.; Mavunkel, B. J.; Goehring, R. R.; Kyle, D. J. Novel Bradykinin Receptor Antagonists from a Structure-Directed Non-Peptide Combinatorial Library. Immunopharmacology 1996, 33, 61-67.
27. 2 Receptor Antagonist. Eur. J. Pharmacol. 1998, 363, 179-187.
28. 2 Receptor Antagonist. Naunyn-Schmiedebergs Arch. Pharmacol. 1999, 360, 278-286.
29. 2 Receptor. Br. J. Pharmacol. 1998, 125, 365-372.
30. 2 Receptor Antagonist Immunopharmacology 1999, 43, 187-194.
31. 2 Bradykinin Receptor Antagonist with Long-Lasting Oral Activity In Animal Models of Inflammatory Hyperalgesia. Br. J. Pharmacol. 2000, 129, 77-86.
32. Sawada, Y.; Kayakiri, H.; Abe, Y.; Imai, K.; Mizutani, Y.; Inamura, N.; Asano, M.; Aramori I.; Hatori C.; Akira K.; Oku T.; Tanaka H. J. Med. Chem., in press.
33. Yoshida, A.; Oda, K.; Komina, H.; Koga, T. JP Patent 10316641, 1998.
34. 2 Receptor Antagonists. Drugs Fut. 1999, 24, 629-46.
35. Manning, D. C.; Vavrek, R.; Stewart, J. M.; Snyder, S. H. Two Bradykinin Binding Sites with Picomolar Affinities. J. Pharmacol. Exp. Ther. 1986, 237, 504-512.
36. Konzett, H.; Rössler, R. Versuchsanordnung zu Untersuchungen ah an der Bronchialmuskulatur. Naunyn-Schmiedeberg's Arch. Exp. Path. Pharmak. 1940, 195, 71-74.
37. Asano, M.; Inamura, N.; Nakahara, K.; Nagayoshi, A.; Isono, T.; Hamada, K.; Oku, T.; Notsu, Y.; Kohsaka, M.; Ono, T.; A 5-Lipoxygenase Inhibitor, FR110302, Suppresses Airway Hyperresponsiveness and Lung Eosinophilia Induced by Sephadex Particles in Rats. Agents Actions 1992, 36, 215-221.
38. Berridge, M. J.; Dawson, R. M. C.; Downes, C. P.; Heslop, J. P.; Irvine, R. F. Changes in the Levels of Inositol Phosphates after Agonist-Dependent Hydrolysis of Membrane Phosphoinositides. Biochem. J. 1983, 212, 473-482.