Synthesis and biological activity of NK-1 selective, N-backbone cyclic analogs of the C-terminal hexapeptide of substance P

Journal of Medicinal Chemistry

Volumn 39, Issue 16, 1996, Pages 3174-3178

  Byk, Gerardo ^a,b   Halle, David ^a   Zeltser, Irena ^a   Bitan, Gal ^a   Selinger, Zvi ^a   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SUBSTANCE P DERIVATIVE; TACHYKININ RECEPTOR AGONIST;

ANIMAL TISSUE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CYCLIZATION; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG STABILITY; DRUG SYNTHESIS; GUINEA PIG; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ILEUM CONTRACTION; MOLECULAR STABILITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; GUINEA PIGS; MOLECULAR SEQUENCE DATA; MUSCLE, SMOOTH; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; PROTEIN BINDING; PROTEIN CONFORMATION; PYRROLIDONECARBOXYLIC ACID; RATS; RECEPTORS, NEUROKININ-1; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTANCE P;

EID: 0029742789     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960154i     Document Type: Article

References (28)

1. Regoli, D.; Boudon, A.; Fouchere, J.-L. Receptors and Antagonists for Substance P and Related Peptides. Pharmacological Rev. 1994, 46, 551-599.
2. Laufer, R.; Wormser, U.; Friedman, Z. Y.; Gilon, C.; Chorev, M.; Selinger, Z. Neurokinin B is a preferred agonist for neuronal Substance P receptor and its action is antagonized by enkephalin. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7444-7448.
3. Wormser, U.; Laufer, R.; Hart, Y.; Chorev, M.; Gilon, C.; Selinger, Z. Highly selective agonists for Substance P receptor subtypes. EMBO J. 1986, 5, 2805-2808.
4. Laufer, R.; Gilon, C.; Chorev, M.; Selinger, Z. Characterization of a neurokinin B receptor site in rat brain using a highly selective radioligand. J. Biol. Chem. 1986, 261, 10257-10263.
5. Laufer, R.; Gilon, C.; Chorev, M.; Selinger, Z. Desensitization with a Selective Agonist Discriminates between Multiple Tachykinin Receptores. Pharmacol. Exp. Ther. 1986, 245, 639-643.
6. Halle, D. Ph.D. Thesis, submitted to the Senate of the Hebrew University, October 1993.
7. Manavalan, P.; Momany, F. A. Conformational Energy Calculations on Substance P. Int. J. Pept. Protein Res. 1982, 20, 351-356.
8. Chassaing, G.; Convert, O.; Laville, S. Preferential Conformation of Substance P in Solution. Eur. J. Biochem. 1986, 154, 77-85.
9. Young, J. K.; Anklin, C.; Hicks, R. P. NMR and Molecular Modeling Investigations of the Neuropeptide Substance P in the Presence of 15 mM Sodium Dodecyl Sulfate Micelles. Biopolymers 1994, 34, 1449-1462.
10. Williams, B. J.; Curtis, N. R.; McKnight, A. T.; Maguire, J.; Foster, A.; Tridgett, R. Development of NK-2 Selective Antagonists. Regul. Pept. 1988, 21, 189P.
11. Maggi, C. A.; Quartara, L.; Giuliani, S.; Patacchini, R. Tachykinin NK-2 Receptor Antagonists. Drugs Future 1993, 18, 155-158.
12. 6-11 Hexapeptide. Pharmazie 1985, 40, 456-459.
13. 6-11 Hexapeptide. Pharmazie 1985, 40, 532-535.
14. Chassaing, G.; Lavielle, S.; Ploux, O.; Julien S.; Convert, O.; Marquet, A.; Beaujouan, J. C.; Torrens, Y.; Glowinsky, J. Biological and Conformational Studies of Cyclic Analogs of Substance P. In Peptides 1984; Ragnarsson, U., Ed.; Almquist & Wiksell: Stockholm, 1985; pp 345-348.
15. Sandberg, B. E. B.; Bishai, W. R.; Hanna, P. Synthesis of Cyclic Analogs Based on Substance P. In Peptides 1984; Ragnarson, U., Ed.; Almquist & Wiksell: Stockholm, 1985; pp 369-372.
16. Theodoropoulos, D.; Poulos, C.; Gatos, D.; Cordopatis, D.; Escher, E.; Mizrahi, J.; Regoli, D.; Dalietos, D.; Furst, A.; Lee, T. D. Conformationally Restricted C-Terminal Peptides of Substance P. Synthesis, Mass Spectral Analysis and Pharmacological Properties. J. Med. Chem. 1985, 28, 1536-1539.
17. Darman, P. S.; Landis, G. C.; Smits, J. R.; Hirning, L. D.; Gulya, K.; Yamamura, H. I.; Burks, T. F.; Hruby, V. J. Conformationally Restricted Cyclic Analogues of Substance P: Insight into the Receptor Binding Process. Biochem. Biophys. Res. Commun. 1988, 127, 656-662.
18. Mutulis, F. K.; Mutule, I. E.; Maurops, G. H.; Sekacis, I. P.; Grigoyeva, V. D.; Kukaine, E. M.; Golubeva, V. V.; Myshliakova, N. V.; Klusha, V. E.; Chipens, G. I. Substance P - a New Type of Cyclic Analogs. Bioorg. Khim. 1985, 11, 1276-1278.
19. 6. Biopolymers 1989, 28, 51-64.
20. Gilon, C.; Halle, D.; Chorev, M.; Selinger, Z.; Byk, G. Backbone Cyclization: A New Method for Conferring Conformational Constraint on Peptides. Biopolymers 1991, 31, 745-750.
21. Gilon, C.; Halle, D.; Chorev, M.; Selinger, Z.; Byk, G. SAR Studies of Cycloseptide: Effects of Cyclization and Charge at Position 6, In Peptides 1992; Smith, J. A., Rivier, J., Eds.; ESCOM Science BV: The Netherlands, 1993; pp 476-477.
22. Gilon, C.; Zeltser, I.; Rashti-Behar, V.; Muller, D.; Bitan, G.; Halle, D.; Bar-Akiva, G.; Selinger, Z.; Byk, G. Backbone cyclization as a tool for imposing conformational constraint on peptides. In Peptide Chemistry 1992; Yanaihara, N., Ed.; ESCOM Science BV: The Netherlands, 1993; pp 482-485.
23. Byk, G.; Gilon, C. Building Units for N-Backbone Cyclic Peptides. 1. Synthesis of Protected N-(ω-Aminoalkylene)amino Acids and Their Incorporation into Dipeptide Units. J. Org. Chem. 1992, 57, 5687-5691.
24. Muller, D.; Zeltser, I.; Bitan, G.; Gilon, C. Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N-(ω-Aminoalkylene)amino Acids and N-(ω-Carboxylkylene)amino Acids. Tetrahedron, submitted for publication.
25. Schiller, P. W.; Nguyen, T. M.-D.; Lamieur, C. Synthesis and OpioidActivity of Cyclic Dynorphin Analogs. Tetrahedron 1988, 44, 733-743.
26. Saulitis, J.; Mierke, D. F.; Byk, G.; Gilon, C.; Kessler, H. Conformation of Cyclic Analogues of Substance P: NMR and Molecular Dynamics in Dimethyl Sulfoxide. J. Am. Chem. Soc. 1992, 114, 4818-4827.
27. Golic-Grdadolnik, S.; Mierke, D.; Byk, G.; Zeltser, I.; Gilon, C.; Kessler, H. Comparison of the Conformation of Active and Nonactive Backbone Cyclic Analogs of Substance P as a Tool to Elucidate Features of the Bioactive Conformatio: NMR and Molecular Dynamics in DMSO and Water. J. Med. Chem. 1994, 37, 2145-2152.
28. Chorev, M.; Rubini, M.; Hart, Y.; Gilon, C.; Wormser, U.; Selinger, Z. Metabolically Stable Analogues of Substance P: Persistant Action of Partially Modified Retro-Inverso Analogues of Substance P on Rat Parotid and Hypothalamic Slices. Eur. J. Pharmacol. 1986, 127, 187-195.