Discovery of Nanomolar Ligands for 7-Transmembrane G-Protein-Coupled Receptors from a Diverse N-(Substituted)glycine Peptoid Library

Journal of Medicinal Chemistry

Volumn 37, Issue 17, 1994, Pages 2678-2685

  Zuckermann, Ronald N ^a   Martin, Eric J ^a   Spellmeyer, David C ^a   Stauber, Gregory B ^a   Shoemaker, Kevin R ^a   Kerr, Janice M ^a   Figliozzi, Gianine M ^a   Goff, Dane A ^a   Siani, Michael A ^a   Simon, Reyna J ^a   Banville, Steven C ^a   Brown, Edward G ^a   Wang, Liang ^a   Richter, Lutz S ^a   Moos, Walter H ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADRENERGIC RECEPTOR; GLYCINE DERIVATIVE; GUANINE NUCLEOTIDE BINDING PROTEIN; METENKEPHALIN; MORPHINE; MU OPIATE RECEPTOR; POLYMER; PRAZOSIN; RECEPTOR PROTEIN;

ARTICLE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; LIGAND BINDING;

AMINO ACID SEQUENCE; ANIMAL; BINDING, COMPETITIVE; BRAIN; COMPARATIVE STUDY; DATABASES, FACTUAL; DIPEPTIDES; ENKEPHALIN, ALA(2)-MEPHE(4)-GLY(5)-; ENKEPHALINS; GLYCINE; GTP-BINDING PROTEINS; LIGANDS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PRAZOSIN; RADIOLIGAND ASSAY; RATS; RECEPTORS, ADRENERGIC, ALPHA-1; RECEPTORS, CELL SURFACE; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0027934780     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00043a007     Document Type: Article

References (60)

1. Hirschmann, R. Medicinal Chemistry in the Golden Age of Biology: Lessons from Steroid and Peptide Research. Angew. Chem., Int. Ed. Engl. 1991, 30, 1278-1301.
2. Moos, W. H.; Green, G. D.; Pavia, M. R. Recent Advances in the Generation of Molecular Diversity. Annu. Rep. Med. Chem. 1993, 28, 315-324.
3. Tuerk, C.; Gold, L. Systematic Evolution of Ligands by Exponential Enrichment: RNA Ligands to Bacteriophage T4 DNA Polymerase. Science 1990, 24, 505-510.
4. Ellington, A. D.; Szostak, J. W. In Vitro Selection of RNA Molecules that Bind Specific Ligands. Nature 1990, 346, 818—822.
5. Bock, L. C.; Griffin, L. C.; Latham, J. A.; Vermann, E. H.; Toole, J. J. Selection of Single-stranded DNA Molecules that Bind and Inhibit Human Thrombin. Nature 1992, 355, 564-566.
6. Maeji, N. J.; Bray, A. M.; Valerio, R. M.; Seldon, M. A.; Wang, J. X.; Geysen, H. M. Systematic Screening of Bioactive Peptides. Pept. Res. 1991, 4, 142-146.
7. Fodor, S. P. A.; Read, J. L.; Pirrung, M. C.; Stryer, L.; Lu, A. T.; Solas, D. Light-Directed, Spatially Addressible Parallel Chemical Synthesis. Science 1991, 251, 767-773.
8. 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 1991, 354, 84-86.
9. Lam, K.; Salmon, S.; Hersh, E.; Hruby, V.; Kazmiersky, W.; Knapp, R. A New Type of Synthetic Peptide Library for Identifying Ligand-Binding Activity. Nature 1991, 354, 82-84.
10. Kerr, J. M.; Banville, S. C.; Zuckermann, R. N. Identification of Antibody Mimotopes Containing Non-Natural Amino Acids by Recombinant and Synthetic Peptide Library Affinity Selection Methods. Bioorg. Med. Chem. Lett. 1993, 3, 463-468.
11. Needles, M. C.; Jones, D. G.; Tate, E. H.; Heinkel, G. L.; Kochersperger, L. M.; Dower, W. J.; Barret, R. W.; Gallop, M. A. Generation and Screening of an Oligonucleotide-Encoded Synthetic Peptide Library. Proc. Natl. Acad. Sci., U.S.A. 1993, 90, 10700-10704.
12. Ohlmeyer, M. H. J.; Swanson, R. N.; Dillard, L. W.; Reader, J. C.; Asouline, G.; Kobayashi, R.; Wigler, M.; Still, W. C. Complex Synthetic Chemical Libraries Indexed with Molecular Tags. Proc. Natl. Acad. Sci., U.S.A. 1993, 90, 10922-10926.
13. Cwirla, S. E.; Peters, E. A.; Barret, R. W.; Dower, W. J. Peptides on Phage: A Vast Library of Peptides for Identifying Ligands. Proc. Natl. Acad. Sci., U.S.A. 1990, 87, 6378-6382.
14. Scott, J. K.; Smith, G. P. Searching for Peptide Ligands with an Epitope Library. Science 1990, 249, 386-390.
15. Devlin, J. J.; Panganiban, L. C.; Devlin, P. E. Random Peptide Libraries: A Source of Specific Protein Binding Molecules. Science 1990, 249, 404-406.
16. Houghten, R. A.; Cooley, C. T. The Use of Synthetic Peptide Combinatorial Libraries for the Determination of Peptide Ligands in Radio-Receptor Assays: Opioid Peptides. Bioorg. Med. Chem. Lett. 1993, 3, 405-412.
17. O'Neil, K. T.; Hoess, R. H.; Jackson, S. A.; Ramachandran, N. S.; Mousa, S. A.; DeGrado, W. F. Identification of Novel Peptide Antagonists for GPIIb/IIIa from a Conformationally Constrained Phage Peptide Library. Proteins 1992, 14, 509—515.
18. Scott, J. K.; Loganathan, D.; Easley, R. B.; Gong, X.; Goldstein, I. J. A Family of Concanavalin A-Binding Peptides from a Hexapeptide Epitope Library. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 5398-5402.
19. Oldenburg, K. R.; Loganathan, D.; Goldstein, I. J.; Schultz, P. G.; Gallop, M. A. Peptide Ligands for a Sugar-Binding Protein Isolated from a Random Peptide Library. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 5393-5397.
20. Plattner, J. J.; Norbeck, D. W. Obstacles to Drug Development from Peptide Leads. In Drug Discovery Technologies; Clark, C. R., Moos, W. H., Eds.; Ellis Horwood Limited: Chichester, England, 1990; pp 92-126.
21. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. Vinylogous Polypeptides: an Alternative Peptide Backbone. J. Am. Chem. Soc. 1992, 114, 6568-6570.
22. Egholm, M.; Buchardt, O.; Nielsen, P. E.; Berg, R. H. Peptide Nucleic Acids (PNA). Oligonucleotide Analogs with an Achiral Backbone. J. Am. Chem. Soc. 1992, 114, 1895-1897.
23. Simon, R. J.; Kania, R. S.; Zuckermann, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D. C.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Peptoids: A Modular Approach to Drug Discovery. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 9367-9371.
24. Smith A. B., III; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. Design, Synthesis, and Crystal Structure of a Pyrrolinone-Based Peptidomimetic Possessing the Conformation of a β-Strand: Potential Application to the Design of Novel Inhibitors of Proteolytic Enzymes. J. Am. Chem. Soc. 1992, 114, 10672-10674.
25. Cho, C. Y.; Moran, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacbos, J. W.; Schultz, P. G. An Unnatural Biopolymer. Science 1993, 261, 1303-1305.
26. Bunin, B. A.; Ellman, J. A. A General and Expedient Method for the Solid-Phase Synthesis of 1,4-Benzodiazepine Derivatives. J. Am. Chem. Soc. 1992, 114, 10997-10998.
27. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. “Diversomers”: An Approach to Nonpeptide, Nonoligomeric Chemical Diversity. Proc. Natl. Acad. Sci., U.S.A. 1993, 90, 6909-6913.
28. Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. Efficient Method for the Preparation of Peptoids [Gligo(NSubstituted Glycines)] by Submonomer Solid-Phase Synthesis. J. Am. Chem. Soc. 1992, 114, 10646-10647.
29. Zuckermann, R. N.; Kerr, J. M.; Siani, M. A.; Banville, S. C. Design, Construction and Application of a Fully Automated Equimolar Peptide Mixture Synthesizer. Int. J. Pept. Protein Res. 1992, 40, 497-506.
30. Furka, Á.; Sebestyén, M.; Asgedom, M.; Dibó, G. 1988, Abstr. 14th Int. Congr. Biochem., Prague, Czechoslovakia; Vol. 5, p 47.
31. Furka, Á.; Sebestyén, M.; Asgedom, M.; Dibó, G. 1988, Abstr. 10th Int. Symp. Med. Chem., Budapest, Hungary; p 288.
32. Furka, Á.; Sebestyén, M.; Asgedom, M.; Dibó, G. General Method for Rapid Synthesis of Multicomponent Peptide Mixtures. Int. J. Pept. Protein Res. 1991, 37, 487-493.
33. Zuckermann, R. N.; Kerr, J. M.; Siani, M. A.; Banville, S. C.; Santi, D. V. Identification of Highest-Affinity Ligands by Affinity Selection from Equimolar Peptide Mixtures Generated by Robotic Synthesis. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 4505-4509.
34. Probst, W. C.; Snyder, L. A.; Schuster, D. I.; Brosius, J.; Sealfon, S. C. Sequence Alignment of the G-Protein Coupled Receptor Superfamily. DNA Cell Biol. 1992, 11, 1-20.
35. Duncia, J. V.; Chiu, A. T.; Carini, D. J.; Gregory, G. B.; Calabrese, J. C.; Timmermanns, P. B. M. W. M. The Discovery of Potent Nonpeptide Angiotensin II Receptor Antagonists: A New Class of Potent Antihypertensives. J. Med. Chem. 1990, 33, 1312.
36. Timmermans, P. B. M. W. M.; Chiu, A. T.; Thoolen, M. J. M. C. α-Adrenergic Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 3; pp 133-185.
37. Main, B. G. β-Adrenergic Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 3; pp 187-228.
38. Blankley, C. J.; Hodges, J. C.; Klutchko, S. R.; Himmelsbach, R. J.; Chucholowski, A.; Connolly, C. J.; Neergaard, S. J.; Van Nieuwenhze, M. S.; Sebastian, A.; Quin, J., III.; Essenburg, A. D.; Cohen, D. M. Synthesis and Structure-Activity Relationships of a Novel Series of Non-peptide Angiotensin II Receptor Binding Inhibitors Specific for the AT2 Subtype. J. Med. Chem. 1991, 34, 3248-3260.
39. Wess, J.; Buhl, T.; Lambrecht, G.; Mutschler, E. Cholinergic Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 3; pp 423-491.
40. Snider, R. M.; Pereira, D. A.; Longo, K. P.; Davidson, R. E.; Vinick, F. J.; Laitinen, K.; Genc-Sehitoglu, E.; Crawley, J. N. UK-73,093: A Non-peptide Neurotensin Receptor Antagonist. Bioorg. Med. Chem. Lett. 1992, 2, 1535-1540.
41. Snider, R. M.; Constantine, J. W.; Lowe, J. A., III; Longo, K. P.; Lebel, W. S.; Woody, H. A.; Drozda, S. E.; Desai, M. C.; Vinick, F. J.; Spencer, R. W.; Hess, H.-J. A Potent Nonpeptide Antagonist of the Substance P (NK1) Receptor. Science 1991, 251, 435-437.
42. Garret, C.; Carruette, A.; Fardin, V.; Moussaoui, S.; Peyronel, J.-F.; Blanchard, J.-C.; Laduron, P. M. Pharmacological Properties of a Potent and Selective Nonpeptide Substance P Antagonist. Proc. Natl. Acad. Sci., U.S.A. 1991, 88, 10208-10212.
43. Bridges, A. J.; Moos, W. H.; Szotek, D. L.; Trivedi, B. K.; Bristol, J. A.; Heffner, T. G.; Bruns, R. F.; Downs, D. A. N6-(2,2-Diphenylethyl)adenosine, a Novel Adenosine Receptor Agoinst with Antipsychotic-like Activity. J. Med. Chem. 1987, 30, 1709-1711.
44. Cody, W. L.; Doherty, A. M.; He, J. X.; DePue, P. L.; Rapundalo, S. T.; Hingorani, G. A.; Major, T. C.; Panek, R. L.; Dudley, D. T.; Haleen, S. J.; LaDouceur, D.; Hill, K. E.; Flynn, M. A.; Reynolds, É. E. Design of a Functional Hexapeptide Antagonist of Endothelin. J. Med. Chem. 1992, 35, 3301-3303.
45. Hull, R. A. D.; Shankley, N. P.; Harper, E. A.; Gerskowitch, V. P.; Black, J. W. 2-Naphthalenesulphonyl L-aspartyl-(2-phenethyDamide (2-NAP)-a Selective Cholecystokinin CCKAreceptor Antagonist. Br. J. Pharmacol. 1993, 108, 734—740.
46. Lloyd, E. J.; Andrews, P. R. A Common Structural Model for Central Nervous System Drugs and Their Receptors. J. Med. Chem. 1986, 29, 453-462.
47. Salituro, G. M.; Pettibone, D. J.; Clineschmidt, B. V.; Willamson, J. M.; Zink, D. L. Potent, Non-peptidic Oxytocin Receptor Antagonists from a Natural Source. Bioorg. Med. Chem. Lett. 1993, 3, 337—340.
48. Clozel, M.; Breu, V.; Burri, K.; Cassal, J.-M.; Fischli, W.; Gray, G. A.; Hirth, G.; Loftier, B.-M.; Miiller, M.; Neidhart, W.; Ramuz, H. Pathophysiological Role of Endothelin Revealed by the First Orally Active Endothelin Receptor Antagonist. Nature 1993, 365, 759-761.
49. Potenza, M. N.; Graminski, G. F.; Lemer, M. R. A Method for Evaluating the Effects of Ligands upon G Protein-Coupled Receptors Using a Recombinant Melanophore-Based Bioassay. Anal. Biochem. 1992, 206, 315—322.
50. Monda, J. M.; Oesterling, J. E. Medical Treatment of Benign Prostatic Hyperplasia: 5-alpha-reductase Inhibitors and alpha-Adrenergic Antagonists. Mayo Clin. Proc. 1993, 68, 670-679.
51. Jaffe, J. H.; Martin, W. R. Opioid Analgesics and Antagonists. In Goodman and Gilman's the Pharmacological Basis of Therapeutics; Gilman, A. G., Rail, T. W., Nies, A. S., Taylor, P., Eds.; Pergamon: New York, 1990; pp 485-521.
52. Geysen, H. M.; Mason, T. J. Screening Chemically Synthesized Peptide Libraries for Biologically-Relevant Molecules. Bioorg. Med. Chem. Lett. 1993, 3, 397-404.
53. Timmermans, P. B. M. W. M.; Ali, F. K.; Kwa, H. Y.; Schoop, A. M. C.; Slothorst-Grisdijk, F. P.; van Zwieten, P. A. Identical Antagonist Selectivity of Central and Peripheral Alphal-Adrenoceptors. Mol. Pharmacol. 1981, 20, 295-301.
54. Gillan, M. G. C.; Kosterlitz, H. W. Spectrum of the mu-, delta-,and kappa-Binding Sites in Homogenates of Rat Brain. Br. J. Pharmacol. 1982, 77, 461-469.
55. Simon, R. J.; Martin, E. J.; Miller, S. M.; Zuckermann, R. N.; Moos, W. H. Using Peptoid Libraries [Oligo N-Substituted Glycines] for Drug Discovery. Tech. Protein Chem. 1994, V, 533-539.
56. Jacobson, K. A.; Marr-Leisy, D.; Rosenkranz, R. P.; Verlander, M. S.; Melmon, K. L.; Goodman, M. Conjugates to Catecholamines. 1. J. Med. Chem. 1983, 26, 492-499.
57. Kerr, J. M.; Banville, S. C.; Zuckermann, R. N. Encoded Combinatorial Peptide Libraries Containing Non-Natural Amino Acids. J. Am. Chem. Soc. 1993, 115, 2529-2531.
58. Nikolaiev, V.; Stierandova, A.; Krchnak, V.; Seligmann, B.; Lam, K. S.; Salmon, S. E.; Lebl, M. Peptide-Encoding for Structure Determination of Nonsequenceable Polymers Within Libraries Synthesized and Tested on Solid-Phase Supports. Pept. Res. 1993, 6, 161-170.
59. Forray, C.; Bard, J. A.; Wetzel, J. M.; Chiu, G.; Shapiro, E.; Tang, R.; Lepor, H.; Hartig, P. R.; Weinshank, R. L.; Branchek, T. A.; Gluchowski, C. The α1-Adrenergic Receptor that Mediates Smooth Muscle Contraction in Human Prostrate has the Pharmacological Properties of the Cloned Human α1c Subtype. Mol. Pharmacol. 1994, 45, 703-708.
60. Rees, D. C.; Hunter, J. C. Opioid Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, pp 805-846.