β-hairpin peptidomimetics: Design, structures and biological activities

Accounts of Chemical Research

Volumn 41, Issue 10, 2008, Pages 1278-1288

  Robinson, John A ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; BIOMIMETIC MATERIAL; CYTOKINE RECEPTOR; PEPTIDE; PROTEIN; PROTEINASE INHIBITOR; RNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; IMMUNOLOGY; METABOLISM; PROTEIN BINDING; PROTEIN SECONDARY STRUCTURE; X RAY CRYSTALLOGRAPHY;

ANTI-INFECTIVE AGENTS; ANTIBODIES; ANTIVIRAL AGENTS; BIOMIMETIC MATERIALS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; MODELS, MOLECULAR; PEPTIDES; PROTEASE INHIBITORS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; PROTEINS; RECEPTORS, CYTOKINE; RNA;

EID: 57349151828     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700259k     Document Type: Article

References (52)

1. Wells, J. A.; McClendon, C. L. Reaching for high-hanging fruit in drug discovery at protein-protein interfaces. Nature 2007, 450, 1001-1009.
2. Robinson, J. A. Horizons in Chemical Immunology - Approaches to Synthetic Vaccine Design. Chimia 2007, 61, 84-92.
3. Sibanda, B. L.; Blundell, T. L.; Thornton, J. M. Conformation of β-hairpins in protein structures. A systematic classification with applications to modelling by homology, electron density fitting and protein engineering. J. Mol. Biol. 1989, 206, 759-777.
4. Gunasekaran, K.; Ramakrishnan, C.; Balaram, P. β-Hairpins in proteins revisited: lessons for de novo design. Protein Eng. 1997, 10, 1131-1141.
5. Sibanda, B. L.; Thornton, J. M. β-Hairpin families in globular proteins. Nature 1985, 316, 170-174.
6. Robinson, J. A. The design, synthesis and conformation of some new β-hairpin mimetics: Novel reagents for drug and vaccine discovery. SynLett 2000, 429-441.
7. Nair, C. M.; Vijayan, M.; Venkatachalapathi, Y. V.; Balaram, P. X-ray crystal structure of pivaloyl-D-Pro-L-Pro-L-Ala-N-methylamide; Observation of a consecutive β-turn conformation. J. Chem. Soc., Chem. Commun. 1979, 1183-1184.
8. Bean, J. W.; Kopple, K. D.; Peishoff, C. E. Conformational analysis of cyclic hexapeptides containing the D-Pro-L-Pro sequence to fix β-turn positions. J. Am. Chem. Soc. 1992, 114, 5328-5334.
9. Chalmers, D. K.; Marshall, G. R. Pro-D-NMe-amino acid and D-Pro-NMe-amino acid: Simple, efficient reverse turn constraints. J. Am. Chem. Soc. 1995, 117, 5927-5937.
10. Jiang, L.; Moehle, K.; Dhanapal, B.; Obrecht, D.; Robinson, J. A. Combinatorial Biomimetic Chemistry. Parallel synthesis of a small library of β-hairpin mimetics based on loop III from human platelet-derived growth factor B. Helv. Chim. Acta 2001, 83, 3097-3112.
11. Clackson, T.; Wells, J. A. A hot spot of binding energy in a hormone-receptor interface. Science 1995, 267, 383-386.
12. Schreiber, G.; Fersht, A. Energetics of protein-protein interactions: analysis of the Barnase-Barstar interface by single mutations and double mutant cycles. J. Mol. Biol. 1995, 248, 478-486.
13. DeLano, W. L. Unraveling hot spots in binding interfaces: progress and challenges. Curr. Opin. Struct. Biol. 2002, 12, 14-20.
14. Reichmann, D.; Rabat, O.; Cohen, M.; Neuvirth, H.; Schreiber, G. The molecular architecture of protein-protein binding sites. Curr. Opin. Struct. Biol. 2007, 17, 67-76.
15. Chothia, C.; Lesk, A. M.; Tramontano, A.; Levitt, M.; Smith-Gill, S. J.; Air, G.; Sheriff, S.; Padlan, E. A.; Davies, D.; Tulip, W. R.; Colman, P. M.; Spinelli, S.; Alzari, P. M.; Poljak, R. J. Conformations of immunoglobulin hypervariable regions. Nature 1989, 342, 877-883.
16. Favre, M.; Moehle, K.; Jiang, L.; Bfeiffer, B.; Robinson, J. A. Structural mimicry of canonical conformations in antibody hypervariable loops using cyclic peptides containing a heterochiral diproline template. J. Am. Chem. Soc. 1999, 121, 2679-2685.
17. Cochran, A. G.; Skelton, N. J.; Starovasnik, M. A. Tryptophan zippers: Stable, monomeric beta -hairpins. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5578-5583.
18. Späth, J.; Stuart, F.; Jiang, L.; Robinson, J. A. Stabilization of a β-hairpin conformation in a cyclic peptide using the templating effect of a heterochiral diproline unit. Helv. Chim. Acta 1998, 81, 1726-1738.
19. Hancock, R. E. W.; Sahl, H. G. Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies. Nat. Biotechnol. 2006, 24, 1551-1557.
20. Brogden, K. A. Antimicrobial peptides: Pore formers or metabolic inhibitors in bacteria. Nat. Rev. Microbiol. 2005, 3, 238-250.
21. Shankaramma, S. C.; Athanassiou, Z.; Zerbe, O.; Moehle, K.; Mouton, C.; Bernardini, F.; Vrijbloed, J. W.; Obrecht, D.; Robinson, J. A. Macrocyclic hairpin mimetics of the cationic antimicrobial peptide protegrin I: A new family of broad-spectrum antibiotics. ChemBioChem 2002, 3, 1126-1133.
22. Robinson, J. A.; Shankaramma, S. C.; Jettera, P.; Kienzl, U.; Schwendener, R. A.; Vrijbloed, J. W.; Obrecht, D. Properties and structure-activity studies of cyclic beta-hairpin peptidomimetics based on the cationic antimicrobial peptide protegrin I. Bioorg. Med. Chem. 2005, 13, 2055-2064.
23. Frecer, V. QSAR analysis of antimicrobial and haemolytic effects of cyclic cationic antimicrobial peptides derived from protegrin-1. Bioorg. Med. Chem. 2006, 14, 6065-6074.
24. Shankaramma, S. C.; Moehle, K.; James, S.; Vrijbloed, J. W.; Obrecht, D.; Robinson, J. A. A family of macrocyclic antibiotics with a mixed peptide-peptoid β-hairpin backbone conformation. Chem. Commun. 2003, 1842-1843.
25. Srinivas, N.; Moehle, K.; Abou-Hadeed, K.; Obrecht, D.; Robinson, J. A. Biaryl amino acid templates in place of D-Pro-L-Pro in cyclic β-hairpin cationic antimicrobial peptidomimetics. Org. Biomol. Chem. 2007, 5, 3100-3105.
26. Tamamura, H.; Tsutsumi, H.; Masuno, H.; Fujii, N. Development of low molecular weight CXCR4 antagonists by exploratory structural tuning of cyclic tetra- and pentapeptide-scaffolds towards the treatment of HIV infection, cancer metastasis and rheumatoid arthritis. Curr. Med. Chem. 2007, 14, 93-102.
27. Burger, J. A.; Burkle, A. The CXCR4 chemokine receptor in acute and chronic leukaemia: a marrow homing receptor and potential therapeutic target. Br. J. Haematol. 2007, 137, 288-296.
28. De Clercq, E. The bicyclam AMD3100 story. Nat. Rev. Drug Discovery 2003, 2, 581-587.
29. Ichiyama, K.; Yokoyama-Kumakura, S.; Tanaka, Y.; Tanaka, R.; Hirose, K.; Bannai, K.; Edamatsu, T.; Yanaka, M.; Niitani, Y.; Miyano-Kurosaki, N.; Takaku, H.; Koyanagi, Y.; Yamamoto, N. A duodenally absorbable CXC chemokine receptor 4 antagonist, KRH-1636, exhibits a potent and selective anti-HIV-1 activity. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 4185-4190.
30. DeMarco, S. J.; Henze, H.; Lederer, A.; Moehle, K.; Mukherjee, R.; Romagnoli, B.; Robinson, J. A.; Brianza, F.; Gombert, F. O.; Lociuro, S.; Ludin, C.; Vrijbloed, J. W.; Zumbrunn, J.; Obrecht, J. P.; Obrecht, D.; Brondani, V.; Hamy, F.; Klimkait, T. Discovery of novel, highly potent and selective beta-hairpin mimetic CXCR4 inhibitors with excellent anti-HIV activity and pharmacokinetic profiles. Bioorg. Med. Chem. 2006, 14, 8396-8404.
31. Luckett, S.; Santiago Garcia, R.; Barker, J. J.; Konarev, A. V.; Shewry, P. R.; Clarke, A. R.; Brady, R. L. High-resolution structure of a potent, cyclic proteinase inhibitor from sunflower seeds. J. Mol. Biol. 1999, 290, 525-533.
32. Descours, A.; Moehle, K.; Renard, A.; Robinson, J. A. A new family of β-hairpin mimetics based on a trypsin inhibitor form sunflower seeds. ChemBioChem 2002, 3, 318-323.
33. Römer, L.; Klein, C.; Dehner, A.; Kessler, H.; Buchner, J. p53 - A natural cancer killer: Structural insights and therapeutic concepts. Angew. Chem., Int. Ed. 2006, 45, 6440-6460.
34. Shmueli, A.; Oren, M. Mdm2: p53's lifesaver. Mol. Cell 2007, 25, 794-796.
35. Kussie, P. H.; Gorina, S.; Marechal, V.; Elenbaas, B.; Moreau, J.; Levine, A. J.; Pavletich, N. P. Structure of the MDM2 oncoprotein bound to the p53 tumour suppressor transactivation domain. Science 1996, 274, 948-953.
36. Dawson, R.; Muller, L.; Dehner, A.; Klein, C.; Kessler, H.; Buchner, J. The N-terminal domain of p53 is natively unfolded. J. Mol. Biol. 2003, 332, 1131-1141.
37. Fasan, R.; Dias, R. L. A.; Moehle, K.; Zerbe, O.; Vrijbloed, J. W.; Obrecht, D.; Robinson, J. A. Using a beta-hairpin to mimic an α helix: Cyclic peptidomimetic inhibitors of the p53-HDM2 protein-protein interaction. Angew. Chem., Int. Ed. 2004, 43, 2109-2112.
38. Garcia-Echeverria, C. P. C.; Blommers, M. J. J.; Furet, P. Discovery of potent antagonists of the interaction between human double minute 2 and tumor suppressor p53. J. Med. Chem. 2000, 43, 3205-3208.
39. Fasan, R.; Dias, R. L. A.; Moehle, K.; Zerbe, O.; Obrecht, D.; Mittl, P. R. E.; Grutter, M. G.; Robinson, J. A. Structure-activity studies in a family of beta-hairpin protein epitope mimetic inhibitors of the p53-HDM2 protein-protein interaction. ChemBioChem 2006, 7, 515-526.
40. Uhrinova, S.; Uhrin, D.; Powers, H.; Watt, K.; Zheleva, D.; Fischer, P.; McInnes, C.; Barlow, P. N. Structure of free MDM2 N-terminal domain reveals conformational adjustments that accompany p53-binding. J. Mol. Biol. 2005, 350, 587-598.
41. Murray, J. K.; Gellman, S. H. Targeting protein-protein interactions: Lessons from P53/MDM2. Pept. Sci. 2007, 88, 657-686.
42. Sidhu, S. S.; Fairbrother, W. J.; Deshayes, K. Exploring protein-protein interactions with phage display. ChemBioChem 2003, 4, 14-25.
43. Dias, R. L. A.; Fasan, R.; Moehle, K.; Renard, A.; Obrecht, D.; Robinson, J. A. Protein ligand design: From phage display to synthetic protein epitope mimetics in human antibody Fc-binding peptidomimetics. J. Am. Chem. Soc. 2006, 128, 2726-2732.
44. DeLano, W. L.; Ultsch, M. H.; deVos, A. M.; Wells, J. A. Convergent solutions to binding at a protein-protein interface. Science 2000, 287, 1279-1283.
45. Hermann, T. Chemical and functional diversity of small molecule ligands for RNA. Biopolymers 2003, 70, 4-18.
46. Silva, J. G.; Carvalho, I. New insights into aminoglycoside antibiotics and derivatives. Curr. Med. Chem. 2007, 14, 1101-1119.
47. Puglisl, J. D.; Chen, L.; Blanchard, S.; Frankel, A. D. Solution Structure of a Bovine Immunodeficiency Virus Tat-TAR Peptide-RNA Complex. Science 1995, 270, 1200-1203.
48. Athanassiou, Z.; Dias, R. L. A.; Moehle, K.; Dobson, N.; Varani, G.; Robinson, J. A. Structural mimicry of retroviral tat proteins by constrained beta-hairpin peptidomimetics: ligands with high affinity and selectivity for viral TAR RNA regulatory elements. J. Am. Chem. Soc. 2004, 126, 6906-6913.
49. Leeper, T. C.; Athanassiou, Z.; Dias, R. L. A.; Robinson, J. A.; Varani, G. TAR RNA recognition by a cyclic peptidomimetic of Tat protein. Biochemistry 2005, 44, 12362-12372.
50. Athanassiou, Z.; Patora, K.; Dias, R. L. A.; Moehle, K.; Robinson, J. A.; Varani, G. Structure-guided peptidomimetic design leads to nanomolar beta-hairpin inhibitors of the Tat-TAR interaction of bovine immunodeficiency Virus. Biochemistry 2007, 46, 741-751.
51. Battiste, J. L.; Mao, H.; Rao, N. S.; Tan, R.; Muhandiram, D. R.; Kay, L. E.; Frankel, A. D.; Williamson, J. R. α-Helix-RNA Major Groove Recognition in an HIV-1 Rev Peptide-RRE RNA Complex. Science 1996, 273, 1547-1551.
52. Moehle, K.; Athanassiou, Z.; Patora, K.; Davidson, A.; Varani, G.; Robinson, J. A. Design of β-hairpin peptidomimetics that inhibit binding of α-helical HIV-1 Rev protein to the Rev response element RNA. Angew. Chem., Int. Ed. 2007, 46, 9101-9104.