Cyclic pentapeptides of chiral sequence DLDDL as scaffold for antagonism of G-protein coupled receptors: Synthesis, activity and conformational analysis by NMR and molecular dynamics of ITF 1565 a substance P inhibitor

Biopolymers

Volumn 50, Issue 2, 1999, Pages 211-219

  Porcelli, Massimiliano ^a   Casu, Mariano ^a   Lai, Adolfo ^a   Saba, Giuseppe ^a   Pinori, Massimo ^b   Cappelletti, Silvana ^b   Mascagni, Paolo ^c  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b Chemi SpA   (Italy)

^c Italfarmaco SpA   (Italy)

Author keywords

Conformation; Cyclic pentapeptides; G protein coupled receptors; Molecular dynamics; Nmr; Substance P

Indexed keywords

ENDOTHELIN; GUANINE NUCLEOTIDE BINDING PROTEIN; ITF 1565; NEUROKININ 1 RECEPTOR; NEUROKININ 2 RECEPTOR ANTAGONIST; PENTAPEPTIDE; SUBSTANCE P ANTAGONIST; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL TISSUE; ARTICLE; DRUG BINDING SITE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; STRUCTURE ACTIVITY RELATION;

ANIMALS; AORTA; GTP-BINDING PROTEINS; GUINEA PIGS; ILEUM; INDICATORS AND REAGENTS; INDOMETHACIN; MALE; MUSCLE CONTRACTION; MUSCLE, SMOOTH; MUSCLE, SMOOTH, VASCULAR; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; PULMONARY ARTERY; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NEUROKININ-1; RECEPTORS, NEUROKININ-2; SUBSTANCE P; VENAE CAVAE;

EID: 0033000078     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(199908)50:2<211::AID-BIP10>3.0.CO;2-E     Document Type: Article

References (42)

1. Penella, J. W.; Rozengurt, E. Growth Factors 1988, 1, 75-83.
2. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leany, E. M.; Sprengeler, P. A.; Furst, G.; Smith, A. B.; Strader, C.; Cascieri, M. A.; Candelore, M. R.; Donaldson, C.; Vale, W.; Maechler, L. J Am Chem Soc 1992, 114, 9217-9218.
3. Lowe, J. A., III; Drozda, S. E.; Snider, R. M.; Longo, K. P.; Zorn, S. H.; Morrone, J.; Jackson, E. R.; McLean, S.; Bryce, D. K.; Bordner, J.; Nagahisa, A.; Kamai, Y.; Duga, O.; Tsuchiya, M. J Med Chem 1992, 35, 2591-2600.
4. Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahan, M.; Madison, V. S.; Rusiescki, V.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J Med Chem 1993, 36, 3039-3049.
5. Ishikawa, M.; Fukami, T.; Nagase, T.; Fujita, K.; Hayama, K.; Mase, T.; Ihara, M.; Yano, M. J Med Chem 1992, 35, 2139-2142.
6. Bean, J. W.; Peishoff, C. E.; Kopple, K. D. Int J Peptide Protein Res 1994, 44, 223-232.
7. Karle, I. L. Int J Peptide Protein Res 1978, 28, 420-427.
8. Pease, L. G.; Watson, C. J Am Chem Soc 1978, 100, 1279-1286.
9. Demel, D.; Kessler, H. Tetrahedron Lett 1976, 32, 2801-2804.
10. Bruch, M. D.; Noggle, J.; Gierasch, L. M. J Am Chem Soc 1985, 107, 1400-1407.
11. Karle, I. L. Int J Peptide Protein Res 1986, 28, 420-427.
12. Stradley, S. J.; Rizo, J.; Bruch, M. D.; Stroup, A. N.; Gierasch, L. M. Biopolymers 1990, 29, 263-287.
13. Aumailly, M.; Gurrath, M.; Müller, G.; Calvete, J.; Timpl, R.; Kessler, H. FEBS Lett 1991, 291, 50-54.
14. Pinori, M.; Cappelletti, S.; Di Gregorio, G.; Porcelli, M.; Murgia, G.; Mascagni, P. In Peptides: Chemistry, Structure and Biology; Kaumaya, P. T. P., Hodges R. S., Eds.; Mayflower Scientific: Birmingham, 1996; pp 497-498.
15. Spatola, A. F.; Anwer, M. K.; Rockwell, A. L.; Gierasch, L. M. J Am Chem Soc 1986, 108, 825-831.
16. Brady, S. F.; Varga, S. L.; Freidinger, R. M.; Schwenk, D. A.; Mendlowski, M.; Veber, D. F. J Org Chem 1979, 44, 3101-3106.
17. Aue, W. P.; Bartholdi, E.; Ernst, R. J Chem Phys 1976, 64, 2229-2242.
18. Gerisenger, C.; Otting, G.; Wüthrich, K.; Ernst, R. J Am Chem Soc 1988, 110, 7870-7872.
19. Bothner-By, A. A.; Stephen, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. J Am Chem Soc 1984, 106, 811-813.
20. Wilker, W.; Leibfritz, D.; Kerssebaum, R.; Bermel, W. Magn Res Chem 1993, 31, 287-292.
21. Kay, L. E.; Keifer, P.; Saarinen, T. J Am Chem Soc 1992, 114, 10663-10665.
22. Corongiu, G.; Martorana, V. In Methods and Techniques in Computational Chemistry: METEC-94; Clementi, E., Ed.; STEF: Cagliari, 1993; Vol. C, Chapter 3.
23. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J Am Chem Soc 1984, 106, 765-784.
24. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J Comp Chem 1986, 2, 230-252.
25. Crippen, G. M.; Havel, T. F. In Distance Geometry and Molecular Conformation; Bawden, D., Ed.; Research Studies Press Ltd.: Taunton, Somerset, UK, 1988.
26. Blaney, J. M.; Crippen, G. M.; Dearing, A.; Dixon, J. S. QCPE, 590 DGEOM 1990.
27. Kirkpatrick, S.; Gelatt, C. D.; Vecchi, M. P. Science 1983, 220, 671-680.
28. Nilges, M.; Clore, M.; Gronenborn, A. M. FEBS Lett 1988, 229, 317-324.
29. Kessler, H.; Anders, U.; Schudok, M. J Am Chem Soc 1990, 112, 5908-5916.
30. Stroup, A. N.; Rockwell, A. L.; Gierasch, L. M. Biopolymers 1992, 32, 1713-1725.
31. Schroeder, E.; Lubke, K.; Hempel, R. Experientia 1965, 21, 70-71.
32. Yamaguchi, I.; Rackur, G.; Leban, J.; Bjorkroth, U.; Rosell, S.; Folkers, K. Acta Chem Scand 1979, 33, 63-68.
33. Folkers, K.; Horig, R. J.; Rosell, S.; Bjorkroth, U. Acta Physiol Scand 1981, 111, 595-506.
34. Leander, S.; Hakanson, R.; Rosell, S.; Folkers, K.; Sundler, F.; Tomqvist, K. Nature 1981, 294, 467-469.
35. Regoli, D.; Escher, E.; Mizrahi, J. Pharmacology 1984, 28, 301-320.
36. Hansen, P. E.; Morgan, B. A. Patent US 4472305, 1984.
37. Hagiwara, D.; Miyake, H.; Morimoto, H.; Murai, M.; Fujii, T.; Matsuo, M. J Med Chem 1992, 35, 3184-3194.
38. Regoli, D.; Boudon, A.; Fauchere, J. L. Pharm Rev 1994, 46, 551-599.
39. Pease, L. G. In Peptides: Structure and Function; Gross, E., Meienhofer, J., Eds.; Pierce Chemical: Rockford, IL, 1979; pp 197-200.
40. Karle, I. L. In Perspectives in Peptide Chemistry; Eberle, A., Geiger, R., Wieland, T., Eds.; Karger, Basel, Switzerland, 1978; pp 261-271.
41. Bystrov, F. V.; Arseniev, S.; Gavrilov, Y. D. J Magn Res 1978, 30, 151-184.
42. Wüthrich, K. NMR in Biological Research: Peptides and Proteins; North-Holland/American Elsevier: Amsterdam-New York, 1976.