A new class of pseudopeptide antagonists of the kinin B1 receptor containing alkyl spacers

Journal of Medicinal Chemistry

Volumn 42, Issue 3, 1999, Pages 409-414

  Galoppini, Claudia ^a   Meini, Stefania ^b   Tancredi, Mariella ^a   Di Fenza, Armida ^a   Triolo, Antonio ^b   Quartara, Laura ^b   Maggi, Carlo A ^b   Formaggio, Fernando ^c   Toniolo, Claudio ^c   Mazzucco, Silvia ^d   Papini, Annamaria ^d   Rovero, Paolo ^a  

^a CNR   (Italy)

^b Menarini Ricerche SpA   (Italy)

^c UNIVERSITY OF PADOVA   (Italy)

^d UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ICATIBANT; KININ; LYSYLLYSYLARGINYLPROLYL(4 HYDROXYPROLYL)GLYCYL 2 (2,3 DIHYDRO 1H INDEN 2 YL)GLYCYLSERYL 2 (2,3 DIHYDRO 1H INDEN 2 YL)GLYCYLOCTAHYDRO 1H INDOLE 2 CARBOXYLIC ACID; MEN 11575; PSEUDOPEPTIDE; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; GUINEA PIG; ILEUM; INTESTINE MUSCLE; NONHUMAN; RAT; RECEPTOR BLOCKING;

AMINO ACID SEQUENCE; ANIMALS; BRADYKININ; GUINEA PIGS; MAGNETIC RESONANCE SPECTROSCOPY; MUSCLE, SMOOTH; OLIGOPEPTIDES; PEPTIDES; RATS; RECEPTORS, NEUROKININ-3;

EID: 0033047991     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980495r     Document Type: Article

References (42)

1. Regoli, D.; Barabè, J. Pharmacology of Bradykinin and Related Kinins. Pharmacol. Rev. 1980, 32, 1-46.
2. (a) Hess, J. F.; Borkowski, J. A.; Young, G. S.; Strader, C. D.; Ransom, R. W. Cloning and Pharmacological Characterization of a Human Bradikinin (BK-2) Receptor. Biochem. Biophys. Res. Commun. 1992, 184, 260-268.
3. 1 Bradykinin Receptor. J. Biol. Chem. 1994, 269, 21583-21586.
4. 1). Genomics 1996, 33, 374-381.
5. 2 Receptor Gene: Full Length cDNA, Genomic Organization and Identification of the Regulatory Region. Biochem. Biophys. Res. Commun. 1995, 211, 226-233.
6. nc, 1-aminocycloalkane-1-carboxylic acids; Ado, 12-aminododecanoic acid; Ahx, 6-aminohexanoic acid; Aoc, 8-aminooctanoic acid; Aun, 11-aminoundecanoic acid; BK, bradykinin; Boc, tert-butyloxycarbonyl; DIEA, diisopropylethylamine; DMF, dimethylformamide; ES-MS, electrospray ionization mass spectrometry; Fmoc, 9-fluorenylmethoxy-carbonyl; HATU, O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; Hyp, 4-hydroxy-L-proline; Igl, α-(2-indanyl)-L-glycine; KD, kallidine; βNal, β-3-(2-naphthyl)alanine; NMM, N-methylmorpholine; NMP, N-methylpyrrolidone; Oic, (3aS,7aS)-octahydroindole-2-carboxylic acid; PEG-PS, poly(ethylene glycol) polystyrene; RP-HPLC, reverse-phase high-performance liquid chromatography; TFA, trifluoroacetic acid; Thi, β-(2-thienyl)-L-alanine; Tic, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.
7. Bhoola, K. D.; Figueroa, C. D.; Worthy, K. Bioregulation of Kinins: Kallikreins, Kininogens and Kininases. Pharmacol. Rev. 1992, 44, 1-80.
8. 1 Receptors: a Review. Immunopharmacology 1995, 30, 1-26.
9. Regoli, D.; Barabè, J.; Park, W. K. Receptor for Bradykinin in Rabbit Aortae. Can. J. Physiol. Pharmacol. 1977, 55, 855-867.
10. 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.
11. 1 Receptor-Related Peptides Antagonists. Hypertension 1996, 28, 833-839.
12. (a) Hock, F. G.; Wirth, K.; Albus, U.; Linz, W.; Gerhards, H. J.; Wiemer, G.; Henke, S.; Breipohl, G.; Konig, W.; Knolle, J.; Scholkens, B. A. HOE 140, a New, Potent and Long Acting Bradykinin Antagonist: in Vitro Studies. Br. J. Pharmacol. 1991, 102, 769-773.
13. (b) Wirth, K.; Hock, F. G.; Albus, U.; Linz, W.; Alpermann, H. G.; Anagnostopoulos, H.; Henke, S.; Breipohl, G.; Konig, W.; Knolle, J.; Scholkens, B. A. HOE 140, a New, Potent and Long Acting Bradykinin Antagonist: in Vivo Studies. Br. J. Pharmacol. 1991, 102, 774-779.
14. 1 Receptor Antagonist. Eur. J. Pharmacol. 1991, 205, 217-218.
15. Stewart, J. M.; Gera, L.; Hanson, W.; Zuzack, J. S.; Burkard, M.; McCullough, R.; Whalley, E. T. A New Generation of Bradykinin Antagonists. Immunopharmacology 1996, 33, 51-60.
16. 2 Receptors. Immunopharmacology 1996, 33, 191-193.
17. 1 Receptor Agonists Containing Alkylic Spacers. Bioorg. Med. Chem. Lett. 1997, 7, 2661-2664.
18. 2 Receptor. Pept. Res. 1995, 8, 16-19.
19. (a) Toniolo, C.; Benedetti, E. Structures of Polypeptides from α-Amino Acids Disubstituted at the α-Carbon. Macromolecules 1991, 24, 4004-4009.
20. α,α-Disubstituted Glycines. Biopolymers (Pept. Sci.) 1996, 40, 519-522.
21. α,α-Disubstituted Glycine. J. Pept. Sci. 1996, 2, 14-27.
22. 10]HOE 140 on 2-Chlorotrityl Resin. Lett. Pept. Sci. 1995, 2, 319-323.
23. Stewart, J. M.; Young, J. D. Solid-Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984; pp 30-31.
24. Rapp, W. Prevention of Side Reaction by High-Speed Continuous Flow Peptide Synthesis. In Peptides 1992; Schneider, C. H., Eberle, A. N., Eds.; ESCOM: Leiden, 1993; pp 243-244.
25. (a) Akaji, K.; Kiso, Y.; Carpino, L. A. Fmoc-based Solid-phase Peptide Syntheis using a New t-Alcohol Type 4-(1′,1′-Dimethyl-1′-hydroxypropyl)phenoxyacetyl Handle (DHPP)-Resin. J. Chem. Soc., Chem. Commun. 1990, 584-586.
26. (b) Steinauer, R.; White, P. Multigram Synthesis of Peptides Containing C-Terminal Proline. In Innovation and Perspectives in Solid-Phase Synthesis; Epton, R., Ed.; Mayflower Worldwide: Birmingham, U.K., 1993; pp 689-692.
27. (a) Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenqing, Y.; Schafer, W. Darstellung Geschutzeter Peptid-fragmente Unter Einsatz Substituierter Triphenylmethyl-harze. Tetrahedron Lett. 1989, 30, 3943-3946.
28. 15-Gastrin I. Tetrahedron Lett. 1989, 30, 3947-3950.
29. Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. 2-Chlorotrityl chloride Resin. Studies on Anchoring of Fmoc-amino Acids and Peptide Cleavage. Int. J. Pept. Protein Res. 1991, 37, 513-520.
30. Carpino, L. A.; El-Faham, A.; Minor, C.; Albericio, F. Advantageous Applications to Azabenzotriazole-Based Coupling Reagents to Solid-Phase Peptide Synthesis. J. Chem. Soc., Chem. Commun. 1994, 201-203.
31. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. T. Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 1970, 34, 595-598.
32. (a) Siegler, G. F.; Fuller, W. D.; Chaturwedi, N. C.; Goodman, M.; Verlander, M. Formation of Oligopeptides During the Synthesis of 9-Fluorenylmethyloxycarbonyl Amino Acid Derivatives. Biopolymers 1983, 22, 2157-2162.
33. (b) Lapatsanis, L.; Milias, G.; Froussios, K.; Kolovos, M. Synthesis of N-2,2,2-(Trichloroethoxycarbonyl)-L-amino Acids and N-(9-Fluorenylmethoxycarbonyl)-L-amino Acids Involving Succinimidooxy Anion as a Leaving Group in Amino Acid Protection. Synthesis 1983, 671-673.
34. Khalil, E. M.; Subasinghe, N. L.; Johnson, R. L. An Efficient and High Yield Method for the N-tert-Butoxycarbonyl Protection of Sterically Hindered Amino Acids. Tetrahedron Lett. 1996, 37, 3441-3444.
35. (a) Wenschuh, H.; Beyermann, M.; Krause, E.; Carpino, L. A.; Bienert, M. Efficient Solid Phase Assembly of Peptides Bearing Contiguous Highly Hindered Aib Residues via Fmoc Fluoride. Tetrahedron Lett. 1993, 23, 3733-3736.
36. (b) Sapia, A. C.; Slomczynska, U.; Marshall, G. R. Evaluation of Two New Coupling Agents for Incorporation of α,α-Dialkylamino Acids, Such as α-Methylalanine, in Solid-Phase Peptide Synthesis. Lett. Pept. Sci. 1994, 1, 283-290.
37. Wysong, C. L.; Yokum, T. S.; Morales, G. A.; Gundry, R. L.; McLaughlin, M. L.; Hammer, R. P. 4-Aminopiperidine-4-carboxylic Acid: A Cyclic α,α-Disubstituted Amino Acid for Preparation of Water-Soluble Highly Helical Peptides. J. Org. Chem. 1996, 61, 7650-7651.
38. Yokum, T. S.; Elzer, P. H.; McLaughlin, M. L. Antimicrobial α,α-Dialkylated Amino Acid Rich Peptides with in-vivo Activity Against an Intracellular Pathogen. J. Med. Chem. 1996, 39, 3603-3605.
39. (e) Albericio, F.; Cases, M.; Alsina, J.; Triolo, S. A.; Carpino, L. A.; Kates, S. A. On the Use of PyAOP, a Phosphonium Salt Derived from HOAt, in Solid-Phase Peptide Synthesis. Tetrahedron Lett. 1997, 38, 4853-4856.
40. 1 Receptors. Br. J. Pharmacol. 1996, 117, 1619-1624.
41. 1 Receptors. Life Sci. 1992, 51, 125-129.
42. Boumrah, D.; Campbell, M. M.; Fenner, S.; Kinsman, R. G. Spacer (29)Molecules in Peptide Sequences: Incorporation into Analogues of Atrial Natriuretic Factor. Tetrahedron 1997, 53, 6977-6992.