Neomycin-acridine conjugate: A potent inhibitor of Rev-RRE binding [16]

Journal of the American Chemical Society

Volumn 122, Issue 5, 2000, Pages 980-981

  Kirk, Sarah R ^a   Luedtke, Nathan W ^a   Tor, Yitzhak ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; NEOMYCIN; VIRUS RNA;

BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; LETTER; PROTEIN RNA BINDING; REACTION ANALYSIS; VIRUS GENOME;

EID: 0034624435     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993387i     Document Type: Letter

References (24)

1. Fields, B. N.; Knipe, D. M.; Howley, P. M., Eds. Fundamental Virology; Lippincott-Raven: Philadelphia, 1996.
2. Tor, Y. Angew. Chem., Int. Ed. 1999, 38, 1579-1582.
3. (a) Michael, K.; Tor, Y. Chem. Eur. J. 1998, 4, 2091-2098.
4. (b) Ecker, D. J.; Griffey, R. H. Drug Discovery Today 1999, 4, 420-429.
5. (c) For a comprehensive review of RNA-ligand interactions, see: Chow, C. S.; Bogdan, F. M. Chem. Rev. 1997, 97, 1489-1513.
6. Coffin, J. M. in ref 1, pp 763-843.
7. Vaishnav, Y. N.; Wong-Staal., F. Annu. Rev. Biochem. 1991, 60, 577-630. Frankel, A. D.; Young, J. A. T. Annu. Rev. Biochem. 1998, 67, 1-25. Pollard, V. W.; Malim, M. H. Annu. Rev. Microbiol. 1998, 52, 491-532. Hope, T. J. Archiv. Biochem. Biophys. 1999, 365, 186-191.
8. Vaishnav, Y. N.; Wong-Staal., F. Annu. Rev. Biochem. 1991, 60, 577-630. Frankel, A. D.; Young, J. A. T. Annu. Rev. Biochem. 1998, 67, 1-25. Pollard, V. W.; Malim, M. H. Annu. Rev. Microbiol. 1998, 52, 491-532. Hope, T. J. Archiv. Biochem. Biophys. 1999, 365, 186-191.
9. Vaishnav, Y. N.; Wong-Staal., F. Annu. Rev. Biochem. 1991, 60, 577-630. Frankel, A. D.; Young, J. A. T. Annu. Rev. Biochem. 1998, 67, 1-25. Pollard, V. W.; Malim, M. H. Annu. Rev. Microbiol. 1998, 52, 491-532. Hope, T. J. Archiv. Biochem. Biophys. 1999, 365, 186-191.
10. Vaishnav, Y. N.; Wong-Staal., F. Annu. Rev. Biochem. 1991, 60, 577-630. Frankel, A. D.; Young, J. A. T. Annu. Rev. Biochem. 1998, 67, 1-25. Pollard, V. W.; Malim, M. H. Annu. Rev. Microbiol. 1998, 52, 491-532. Hope, T. J. Archiv. Biochem. Biophys. 1999, 365, 186-191.
11. Zapp, M. L.; Stern, S.; Green, M. R. Cell 1993, 74, 969-978.
12. See: Zapp, M. L.; Young, D. W.; Kumar, A.; Singh, R.; Boykin, D. W.; Wilson, W. D.; Green, M. R. Bioorg. Med. Chem. 1997, 5, 1149-1155. Tok, J. B.-H.; Cho, J.; Rando, R. R. Tetrahedron 1999, 55, 5741-5758. Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 10150-10155.
13. See: Zapp, M. L.; Young, D. W.; Kumar, A.; Singh, R.; Boykin, D. W.; Wilson, W. D.; Green, M. R. Bioorg. Med. Chem. 1997, 5, 1149-1155. Tok, J. B.-H.; Cho, J.; Rando, R. R. Tetrahedron 1999, 55, 5741-5758. Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 10150-10155.
14. See: Zapp, M. L.; Young, D. W.; Kumar, A.; Singh, R.; Boykin, D. W.; Wilson, W. D.; Green, M. R. Bioorg. Med. Chem. 1997, 5, 1149-1155. Tok, J. B.-H.; Cho, J.; Rando, R. R. Tetrahedron 1999, 55, 5741-5758. Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 10150-10155.
15. Holland, S. M.; Chavez, M.; Gerstberger, S.; Venkatesan, S. J. Virol. 1992, 66, 3699-3706. Tilley, L. S.; Malim, M. H.; Tewary, H. K.; Stockley, P. G.; Cullen, B. R. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 758-762.
16. Holland, S. M.; Chavez, M.; Gerstberger, S.; Venkatesan, S. J. Virol. 1992, 66, 3699-3706. Tilley, L. S.; Malim, M. H.; Tewary, H. K.; Stockley, P. G.; Cullen, B. R. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 758-762.
17. Kjems, J.; Canlan; B. J.; Frankel, A. D.; Sharp, P. A. EMBO J. 1992, 11, 1119-1129.
18. Battiste, J. L.; Mao, H.; Rao, N. S.; Tan, R.; Muhandiram, D. R.; Kay, L. E.; Frankel, A. D.; Williamson, J. R. Science 1996, 273, 1547-1551.
19. Wilson, W. B.; Ratmeyer, L.; Cegla, M. T.; Spychala, J.; Boykin, D.; Demeunynyck, M.; Lhomme, J.; Krishnan, G.; Kennedy, D.; Vinayak, R.; Zon, G. New J. Chem. 1994, 18, 419-423.
20. See Supporting Information for experimental details.
21. 2 derivative.
22. A second lower affinity RRE binding site is filled at higher neo-acridine concentrations (5-10 μM). Footprinting data at these concentrations suggest a lower affinity neo-acridine binding site located around A68, another bulged nucleotide. See ref 12.
23. A possible explanation is the formation of a G48·U72 base pair and expulsion of G71 into solution upon intercalation of the acridine moiety.
24. The Rev peptide has been shown to have the same RNA binding domain as the full length Rev protein. See ref 9 and: Daly, T. J.; Rennert, P.; Lynch, P.; Barry, J. K.; Dundas, M.; Rusche, J. R.; Doten, R. C.; Auer, M.; Farrington, G. K. Biochemistry 1993, 32, 8945-8954.