Structural mimicry of retroviral Tat proteins by constrained β-hairpin peptidomimetics: Ligands with high affinity and selectivity for viral TAR RNA regulatory elements

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 6906-6913

  Athanassiou, Zafiria ^a   Dias, Ricardo L A ^a   Moehle, Kerstin ^a   Dobson, Neil ^b   Varani, Gabriele ^b   Robinson, John A ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; RNA; VIRUSES;

BOVINE IMMUNODEFICIENCY VIRUS (BIV); HAIRPIN STRUCTURES;

PROTEINS;

LIGAND; PROLINE; TRANSACTIVATOR PROTEIN; VIRUS PROTEIN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; BINDING AFFINITY; BOVINE IMMUNODEFICIENCY LIKE VIRUS; DNA RESPONSIVE ELEMENT; HUMAN IMMUNODEFICIENCY VIRUS; LIGAND BINDING; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; REGULATORY RNA SEQUENCE; RETROVIRUS; RNA BINDING; RNA STRUCTURE; TRANSACTIVATOR RESPONSE ELEMENT;

AMINO ACID SEQUENCE; ANIMALS; BASE PAIRING; BASE SEQUENCE; BIOMIMETICS; CATTLE; ELECTROPHORETIC MOBILITY SHIFT ASSAY; GENE PRODUCTS, TAT; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; PROTEIN STRUCTURE, TERTIARY; RNA, VIRAL; RNA-BINDING PROTEINS;

EID: 3042776646     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0497680     Document Type: Article

References (47)

1. Fischer, U.; Huber, J.; Boelens, W. C.; Mattaj, I. W.; Lührmann, R. Cell 1995, 82, 475-483.
2. Graeble, M. A.; Churcher, M. J.; Lowe, A. D.; Gait, M. J.; Karn, J. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6184-6188.
3. Dingwall, C.; Ernberg, I.; Gait, M. J.; Green, S. M.; Heaphy, S.; Karn, J.; Lowe, A. D.; Singh, M.; Skinner, M. A.; Valerio, R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 6925-6929.
4. Gallego, J.; Varani, G. Acc. Chem. Res. 2001, 34, 836-843.
5. Wilson, W. D.; Li, K. Curr. Med. Chem. 2000, 7, 73-98.
6. Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980-981.
7. Mei, H.-Y.; Cui, M.; Heldsinger, A.; Lemrow, S. M.; Loo, J. A.; Sannes-Lowery, K. A.; Sharmeen, L.; Czarnik, A. W. Biochemistry 1998, 37, 14204-14212.
8. Gonda, M. A.; Luther, D. G.; Fong, S. E.; Tobin, G. J. Virus Res. 1994, 32, 155-181.
9. Jones, K. A.; Peterlin, B. M. Annu. Rev. Biochem. 1994, 63, 717-743.
10. Wei, P.; Garber, M. E.; Fang, S.-M.; Fischer, W. H.; Jones, K. A. Cell 1998, 92, 451-462.
11. Tok, J. B.-H.; Des Jean, R. C.; Fenker, J. Bioorg. Med. Chem. Lett. 2001, 11, 43-46.
12. Smith, C. Mol. Cell 2000, 6, 1067-1076.
13. Frankel, A. D. Curr. Opin. Struct. Biol. 2000, 10, 332-340.
14. Xavier, K. A.; Eder, P. S.; Giordano, T. Trends Biotechnol. 2000, 18, 349-356.
15. Leulliot, N.; Varani, G. Biochemistry 2001, 40, 7947-7956.
16. Huq, I.; Wang, X.; Rana, T. M. Nat. Struct. Biol. 1997, 4, 881-882.
17. Huq, I.; Ping, Y.-H.; Tamilarasu, N.; Rana, T. M. Biochemistry 1999, 38, 5172-5177.
18. Hamy, F.; Felder, E. R.; Heizmann, G.; Lazdins, J.; Aboul-ela, F.; Varani, G.; Karn, J.; Klimkait, T. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3548-3553.
19. Puglisi, J. D.; Tan, R.; Canlan, B. J.; Frankel, A. D.; Williamson, J. R. Science 1992, 257, 76-80.
20. Tan, R.; Frankel, A. D. Biochemistry 1992, 31, 10288-10294.
21. Aboul-ela, F.; Karn, J.; Varani, G. J. Mol. Biol. 1995, 253, 313-332.
22. Aboul-ela, F.; Karn, J.; Varani, G. Nucleic Acids Res. 1996, 24, 3974-3981.
23. Al-Hashimi, H. M.; Gosser, Y.; Gorin, A.; Hu, W.; Majumdar, A.; Patel, D. J. J. Mol. Biol. 2002, 315, 95-102.
24. Ye, X.; Kumar, R. A.; Patel, D. J. Chem. Biol. 1995, 2, 827-840.
25. Puglisi, J. D.; Chen, L.; Blanchard, S.; Frankel, A. D. Science 1995, 270, 1200-1203.
26. Herrmann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1904.
27. Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
28. Cheng, A.; Calabro, V.; Frankel, A. Curr. Opin. Struct. Biol. 2001, 11, 478-484.
29. Runyon, S. T.; Puglisi, J. D. J. Am. Chem. Soc. 2003, 125, 15704-15705.
30. Atherton, E.; Sheppard, R. C. Solid-phase Peptide Synthesis-A Practical Approach; IRL Press: Oxford, 1989.
31. Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161-214.
32. Milligan, J. Nucleic Acids Res. 1987, 15, 8733-8798.
33. Bartels, C.; Xia, T.; Billeter, M.; Guentert, P.; Wüthrich, K. J. Biomol. NMR 1995, 6, 1-10.
34. Lippens, G.; Dhallium, C.; Wieruszeski, J. M. J. Biomol. NMR 1995, 5, 327-331.
35. Guntert, P.; Mumenthaler, C.; Wüthrich, K. J. Mol. Biol. 1997, 273, 283-298.
36. Van Gunsteren, W. F.; Billeter, S. R.; Eising, A. A.; Hünenberger, P. H.; Krüger, P.; Mark, A. E.; Scott, W. R. P.; Tironi, I. G. Biomolecular Simulation: The GROMOS96 Manual and User Guide; Hochschulverlag AG an der ETH Zurich, 1996.
37. Koradi, R.; Billeter, M.; Wüthrich, K. J. Mol. Graphics 1996, 14, 51-55.
38. Nicholls, A.; Sharp, K. A.; Honig, B. Proteins 1991, 11, 281-296.
39. Chen, L.; Frankel, A. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 5077-5081.
40. Sibanda, B. L.; Blundell, T. L.; Thornton, J. M. J. Mol. Biol. 1989, 206, 759-777.
41. Favre, M.; Moehle, K.; Jiang, L.; Pfeiffer, B.; Robinson, J. A. J. Am. Chem. Soc. 1999, 121, 2679-2685.
42. Jiang, L.; Moehle, K.; Dhanapal, B.; Obrecht, D.; Robinson, J. A. Helv. Chim. Acta 2000, 83, 3097-3112.
43. Chen, L.; Frankel, A. D. Biochemistry 1994, 33, 2708-2715.
44. Wüthrich, K. NMR of Proteins and Nucleic Acids; John Wiley & Sons: New York, 1986.
45. Späth, J.; Stuart, F.; Jiang, L.; Robinson, J. A. Helv. Chim. Acta 1998, 81, 1726-1738.
46. Shankaramma, S. C.; Athanassiou, Z.; Zerbe, O.; Moehle, K.; Mouton, C.; Bernardini, F.; Vrijbloed, J. W.; Obrecht, D.; Robinson, J. A. ChemBioChem 2002, 3, 1126-1133.
47. Descours, A.; Moehle, K.; Renard, A.; Robinson, J. A. ChemBioChem 2002, 3, 318-323.