Sequences in the HSP90 promoter form G-quadruplex structures with selectivity for disubstituted phenyl bis-oxazole derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 18, 2012, Pages 5930-5935

  Ohnmacht, Stephan A ^a   Micco, Marialuisa ^a   Petrucci, Vanessa ^a   Todd, Alan K ^a   Reszka, Anthony P ^a   Gunaratnam, Mekala ^a   Carvalho, Marta A ^a   Zloh, Mire ^a   Neidle, Stephen ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

HSP90; Promoter; Quadruplex; Small molecule

Indexed keywords

ANTINEOPLASTIC AGENT; BRACO 19; DISUBSTITUTED PHENYL BIS OXAZOLE DERIVATIVE; DOUBLE STRANDED DNA; GUANINE QUADRUPLEX; HEAT SHOCK PROTEIN 90; OXAZOLE DERIVATIVE; TELOMESTATIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CIRCULAR DICHROISM; DNA BINDING; DRUG SELECTIVITY; GENE EXPRESSION; GENE SEQUENCE; HUMAN; MELTING POINT; NUCLEAR MAGNETIC RESONANCE IMAGING; PROMOTER REGION; PROTEIN TARGETING; SUBSTITUTION REACTION; TELOMERE;

DNA; DOSE-RESPONSE RELATIONSHIP, DRUG; G-QUADRUPLEXES; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; OXAZOLES; PROMOTER REGIONS, GENETIC; STRUCTURE-ACTIVITY RELATIONSHIP; TELOMERE;

EID: 84865469110     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.07.065     Document Type: Article

References (53)

1. D.J. Patel, A.T. Phan, and V. Kuryavyi Nucleic Acids Res. 35 2007 7429
2. S. Burge, G.N. Parkinson, P. Hazel, A.K. Todd, and S. Neidle Nucleic Acids Res. 34 2006 5402
3. S. Neidle Curr. Opin. Struct. Biol. 19 2009 1
4. See for example D. Sun, B. Thompson, B.E. Cathers, M. Salazar, S.M. Kerwin, J.O. Trent, T.C. Jenkins, S. Neidle, and L.H. Hurley J. Med. Chem. 40 1997 2113
5. D. Monchaud, and M.-P. Teulade-Fichou Org. Biomol. Chem. 6 2008 627
6. D.Z. Yang, and K. Okamoto Future Med. Chem. 2 2010 619
7. S. Neidle Therapeutic Aspects of Quadruplex Nucleic Acids 2011 Academic Press San Diego
8. J.W. Shay, and W.E. Wright Nature Rev. Drug Discov. 5 2006 577
9. J.L. Huppert, and S. Balasubramanian Nucleic Acids Res. 33 2005 2908
10. A.K. Todd, M. Johnston, and S. Neidle Nucleic Acids Res. 33 2005 2901
11. J.L. Huppert, and S. Balasubramanian Nucleic Acids Res. 35 2007 406
12. A. Siddiqui-Jain, C.L. Grand, D.J. Bearss, and L.H. Hurley Proc. Natl. Acad. Sci. U.S.A. 99 2002 11593
13. S. Balasubramanian, L.H. Hurley, and S. Neidle Nature Rev. Drug Discov. 10 2011 261
14. M. Wieland, and J.S. Hartig Chem. Biol. 14 2007 757
15. A. Bugaut, and S. Balasubramanian Nucleic Acids Res. 40 2012 4727
16. See for example: T.-M. Ou, Y.-J. Lu, C. Zhang, Z.-S. Huang, X.-D. Wang, J.-H. Tan, Y. Chen, D.-L. Ma, K.-Y. Wong, J.C.-O. Tang, A. Sun-Chi, and L.-Q. Gu J. Med. Chem. 50 2007 1465
17. Z.A. Waller, S.A. Sewitz, S.T. Hsu, and S. Balasubramanian J. Am. Chem. Soc. 131 2009 12628
18. For example J. Alzeer, B.R. Vummidi, P.J. Roth, and N.W. Luedtke Angew. Chem., Int. Ed. Engl. 48 2009 9362
19. R.V. Brown, F.L. Danford, V. Gokhale, L.H. Hurley, and T.A. Brooks J. Biol. Chem. 286 2011 41018
20. M. Gunaratnam, S. Swank, S.M. Haider, K. Galesa, A.P. Reszka, M. Beltran, F. Cuenca, J.A. Fletcher, and S. Neidle J. Med. Chem. 52 2009 3774
21. K.I. McLuckie, Z.A. Waller, D.A. Sanders, D. Alves, R. Rodriguez, J. Dash, G.J. McKenzie, A.R. Venkitaraman, and S. Balasubramanian J. Am. Chem. Soc. 133 2011 2658
22. R. Rodriguez, K.M. Miller, J.V. Forment, C.R. Bradshaw, M. Nikan, S. Britton, T. Oelschlaegel, B. Xhemalce, S. Balasubramanian, and S.P. Jackson Nature Chem. Biol. 8 2012 301
23. G.N. Parkinson, M.P.H. Lee, and S. Neidle Nature 417 2002 876
24. A. Ambrus, D. Chen, J. Dai, T. Bialis, R.A. Jones, and D. Yang Nucleic Acids Res. 34 2006 2723
25. K.N. Luu, A.T. Phan, V. Kuryavyi, L. Lacroix, and D.J. Patel J.Am. Chem. Soc. 128 2006 9963
26. A.T. Phan, Y.S. Modi, and D.J. Patel J. Am. Chem. Soc. 126 2004 8710
27. R.I. Mathad, E. Hatzakis, J. Dai, and D. Yang Nucleic Acids Res. 39 2011 9023
28. A.T. Phan, V. Kuryavyi, S. Burge, S. Neidle, and D.J. Patel J. Am. Chem. Soc. 129 2007 4386
29. S.T. Hsu, P. Varnai, A. Bugaut, A.P. Reszka, S. Neidle, and S. Balasubramanian J. Am. Chem. Soc. 131 2009 13399
30. D. Wei, G.N. Parkinson, A.P. Reszka, and S. Neidle Nucleic Acids Res. 40 2012 4691
31. J.X. Dai, D. Chen, R.A. Jones, L.H. Hurley, and D.Z. Yang Nucleic Acids Res. 34 2006 5133
32. K.W. Lim, L. Lacroix, D.J. Yue, J.K. Lim, J.M. Lim, and A.T. Phan J. Am. Chem. Soc. 132 2010 12331
33. X. Tong, W. Lan, X. Zhang, H. Wu, M. Liu, and C. Cao Nucleic Acids Res. 39 2011 6753
34. L. Neckers, and P. Workman Clin. Cancer Res. 18 2012 64
35. S.H. Millson, C.S. Chua, S.M. Roe, S. Polier, S. Solovieva, L.H. Pearl, T.S. Sim, C. Prodromou, and P.W. Piper FASEB J. 25 2011 3828
36. See for example: B.R. Keppler, A.T. Grady, and M.B. Jarstfer J. Biol. Chem. 281 2006 19840
37. R.H. Kim, R. Kim, W. Chen, S. Hu, K.H. Shin, N.H. Park, and M.K. Kang Carcinogenesis 29 2008 2425
38. S. Cogoi, and L.E. Xodo Nucleic Acids Res. 34 2006 2536
39. N.H. Capbell, G.N. Parkinson, A.P. Reszka, and S. Neidle J. Am. Chem. Soc. 130 2008 6722
40. See also Nielsen M.-Y. Kim, H. Vankayalapati, K. Shin-ya, K. Wierzba, and L.H. Hurley J. Am. Chem. Soc. 124 2002 2098
41. S.G. Rzuczek, D.S. Pilch, A. Liu, L. Liu, E.J. LaVoie, and J.E. Rice J. Med. Chem. 53 2010 3632
42. M.C.T. Ulven Curr. Med. Chem. 17 2010 3438 for a recent review of macrocyclic quadruplex ligands.
43. A.D. Moorhouse, A.M. Santos, M. Gunaratnam, M. Moore, S. Neidle, and J.E. Moses J. Am. Chem. Soc. 128 2006 15972
44. W.C. Drewe, and S. Neidle Chem. Commun. 2008 5295
45. M.R. Reeder, H.E. Gleaves, S.A. Hoover, H.R. Imbordino, and J. Pangborn J. Org. Process Res. Dev. 7 2003 696
46. A.M. van Leusen, B.E. Hoogenboom, and H. Siderius Tetrahedron Lett. 23 1972 2369
47. N.A. Strotman, H.R. Chobanian, Y. Gou, J. He, and J.E. Wilson Org. Lett. 16 2010 3578
48. S.A. Ohnmacht, P. Mamone, A.J. Culshaw, and M.F. Greaney Chem. Commun. 10 2008 1241
49. m are ±0.1 °C.
50. M. Gunaratnam, M. de la Fuente, S.M. Hampel, A.K. Todd, A.P. Reszka, A. Schatzlein, and S. Neidle Bioorg. Med. Chem. 19 2011 7151
51. F. Hamon, E. Large, A. Guédin-Beaurepaire, M. Rouchon-Dagois, A. Sidibe, D. Monchaud, J.-L. Mergny, J.-F. Riou, C.-H. Nyugen, and M.-P. Teulade-Fichou Angew. Chem., Int. Ed. 50 2011 8745
52. G.W. Collie, R. Promontorio, S.M. Hampel, M. Micco, S. Neidle, and G.N. Parkinson J. Am. Chem. Soc. 134 2012 2723
53. J. Dai, M. Carver, L.H. Hurley, and D. Yang J. Am. Chem. Soc. 134 2012 17673