Rediscovering an endothelin antagonist (BQ-123): A self-deconvoluting cyclic pentapeptide library

Journal of Medicinal Chemistry

Volumn 39, Issue 19, 1996, Pages 3842-3846

  Spatola, Arno F ^a   Crozet, Yvon ^a   DeWit, Damiane ^b   Yanagisawa, Masashi ^b  

^a UNIVERSITY OF LOUISVILLE   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYCLO(DEXTRO TRYPTOPHYL DEXTRO ASPARTYLPROLYL DEXTRO VALYLLEUCYL); CYCLOPEPTIDE; ENDOTHELIN A RECEPTOR; ENDOTHELIN RECEPTOR ANTAGONIST; PENTAPEPTIDE;

ANIMAL CELL; ARTICLE; CHO CELL; CONTROLLED STUDY; CYCLIZATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; CHO CELLS; CRICETINAE; ENDOTHELINS; HUMANS; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; RADIOLIGAND ASSAY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029837395     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9604078     Document Type: Article

References (32)

1. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J. Med. Chem. 1994, 37, 1233-1251.
2. Gordon, E. M.; Barrett, R.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J. Med. Chem. 1994, 37, 1385-1401.
3. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Combinatorial synthesis - The design of compound libraries and their application to drug discovery. Tetrahedron 1995, 51, 8135-8173.
4. Thompson, L. A.; Ellman, J. A. Synthesis and applications of small molecule libraries. Chem. Rev. 1996, 96, 555-600.
5. DeWitt, S.; Kiely, J.; Stankovic, C.; Schroeder, M.; Cody, D.; Pavia, M. "Diversomers": an approach to nonpeptide, nonoligomeric chemical diversity. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913.
6. Bunin, B.; Plunkett, M.; Ellmann, J. The combinatorial synthesis and chemical and biological evaluation of 1,4-benzodiazepine library. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4708-4712.
7. Cho, C.; Moran, E.; Stephans, J.; Fodor, S.; Adams, C.; Sundaram, A.; Jacobs, J.; Schultz, P. An unnatural biopolymer. Science 1993, 267, 1303-1305.
8. Ladner, R. C. Constrained peptides as binding entities. Tibtech 1995, 13, 426-430.
9. Olivera, B.; Rivier, J.; Clark, C.; Ramilo, C.; Corpuz, G.; Abogadie, F.; Mena, E.; Woodward, S.; Hillyard, D.; Cruz, L. Diversity of conus neuropeptides. Science 1990, 249, 257-263.
10. O'Neil, K. T.; Hoess, R. H.; Jackson, S. A.; Ramachandran, N.; Mousa, S. A.; DeGrado, W. F. Identification of GP-IIB/IIIA Binding Peptides Using a Conformationally Constrained Phage Peptide Library. Proteins 1992, 14, 509-515.
11. Rovero, P.; Quartara, L.; Fabbri, G. Synthesis of cyclic peptides on solid support. Tetrahedron Lett. 1991, 32, 2639-2642.
12. Kates, S. A.; Solé, N. A.; Johnson, C.; Hudson, D.; Barany, G.; Albericio, F. A novel, convenient, three phase synthesis of cyclic peptides. Tetrahedron Lett. 1993, 34, 1549-1552.
13. Kates, S. A.; Solé, N. A.; Albericio, F.; Barany, G. Solid phase synthesis of cyclic peptides. In Peptides: Design, Synthesis and Biological Activity; Basava, C., Anantharamaiah, G. M., Eds.; Birkhäuser: Boston, 1994; pp 39-58.
14. Darlak, K.; Romanovskis, P.; Spatola, A. Cyclic peptide libraries. In Peptides: Chemistry, Structure, and Biology; Hodges, R., Smith, J., Eds.; ESCOM: Leiden, 1994; pp 981-983.
15. Spatola, A. F.; Darlak, K.; Romanovskis, P. An approach to cyclic peptide libraries: reducing epimerization in medium size during solid phase synthesis. Tetrahedron Lett. 1996, 37, 591-594.
16. Green, J.; Bradley, K. Studies on the acylation of hydroxy-functionalized resins using Fmoc amino acids activated using diisopropylcarbodiimide/HOBt or as acid fluorides. Tetrahedron 1993, 49, 4141-4146.
17. Krchnak, V.; Vagner, J. Color monitored solid-phase multiple peptide synthesis under low-pressure continuous-flow conditions. Pept. Res. 1990, 3, 182.
18. Fields, G.; Tian, Z.; Barany, G. In Synthetic Peptides: A User's Guide; Grant, G., Ed.; W. H. Freeman and Co.: New York, 1992; Chapter 3.
19. Gairi, M.; Lloyd-Williams, P.; Albericio, F.; Giralt, E. Use of BOP reagent for the suppression of diketopiperazine formation in Boc/ Bzl solid-phase peptide synthesis. Tetrahedron Lett. 1990, 31, 7363-7366.
20. Castro, B.; Dormoy, J.; Evin, G.; Selve, C. Reactif de couplage peptidique IV (1)-L'hexafluorophosphate de benzotriazolyl N-oxytrisdimethylamino phosphonium (B.O.P.). (Peptide coupling reagents. IV. N-[Oxytris(dimethylamino)phosphonium]benzotriazole hexafluorophosphate.) Tetrahedron Lett. 1975, 1219-1222.
21. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
22. Hellberg, S.; Sjöström, M.; Skagerberg, B.; Wold, S. Peptide quantitative structure-activity relationship: a multivariate approach. J. Med. Chem. 1987, 30, 1126-1135.
23. Hansch, C. In Drug Design; Ariens, E., Ed.; Academic Press: New York and London, 1971; Chapter 2.
24. A receptor. Life Sci. 1992, 50, 247-255.
25. Geysen, H. M. U.S. Patent 5 194 392, 1993.
26. Houghten, R.; Pinilla, C.; Blondelle, S.; Appel, J.; Dooley, C.; Cuervo, J. Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery. Nature (London) 1991, 354, 84-86.
27. Dooley, C. T.; Houghten, R. A. The use of positional scanning synthetic peptide combinatorial libraries for the rapid determination of opioid receptor ligands. Life Sci. 1993, 52, 1509-1517 and references therein.
28. Houghten, R.; Bray, M.; Degraw, S.; Kirby, C. Simplified procedure for carrying out simultaneous multiple hydrogen fluoride cleavages of protected peptide resins. Int. J. Pept. Protein Res. 1986, 27, 673-768.
29. α-Boc-L-glutamic acid. Int. J. Pept. Protein Res. 1990, 35, 215-218.
30. Stewart, J.; Young, J. Solid Phase Peptide Synthesis; Pierce Chemical Co.: Rockford, 1984; pp 61-62.
31. Xu, D.; Emoto, N.; Giaid, A.; Slaughter, C.; Kaw, S.; deWit, D.; Yanagisawa, M. ECE-1: a membrane-bound metalloprotease that catalyzes the proteolytic activation of big endothelin-1. Cell 1994, 78, 473-485.
32. Sakurai, T.; Yanagisawa, M.; Takuwa, Y.; Miyazaki, H.; Kimura, S.; Goto, K.; Masaki, T. Cloning of a cDNA encoding a nonisopeptide-selective subtype of the endothelin receptor. Nature 1990, 348, 732-735.