Identification of novel telomeric G-quadruplex-targeting chemical scaffolds through screening of three NCI libraries

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 8, 2012, Pages 3006-3010

  Rahman, Khondaker M ^a   Tizkova, Karolina ^b   Reszka, Anthony P ^a   Neidle, Stephen ^a   Thurston, David E ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

^b UNIVERSITY OF VETERINARY AND PHARMACEUTICAL SCIENCES   (Czech Republic)

Author keywords

DNA; Drug likeness; Duplex; FRET based assay; G quadruplex; High throughput screen; Ligands; NCI Diversity Set

Indexed keywords

DOUBLE STRANDED DNA; GUANINE QUADRUPLEX; GUANINE QUADRUPLEX TARGETING AGENT; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; DATA BASE; DNA DENATURATION; DRUG SELECTIVITY; DRUG STRUCTURE; FLUORESCENCE RESONANCE ENERGY TRANSFER; GENE TARGETING; MOLECULAR WEIGHT;

G-QUADRUPLEXES; HUMANS; MOLECULAR STRUCTURE; NATIONAL CANCER INSTITUTE (U.S.); SMALL MOLECULE LIBRARIES; UNITED STATES;

EID: 84859445323     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.02.020     Document Type: Article

References (77)

1. A.K. Todd, S.M. Haider, G.N. Parkinson, and S. Neidle Nucleic Acids Res. 35 2007 5799
2. A.T. Phan, V. Kuryavyi, K.N. Luu, and D.J. Patel Nucleic Acids Res. 35 2007 6517
3. A.K. Todd, M. Johnston, and S. Neidle Nucleic Acids Res. 33 2005 2901
4. J.L. Huppert, and S. Balasubramanian Nucleic Acids Res. 33 2005 2908
5. J.L. Huppert Chem. Soc. Rev. 37 2008 1375
6. D. Monchaud, and M.-P. Teulade-Fichou Org. Biomol. Chem. 6 2008 627
7. M. Franceschin Eur. J. Org. Chem. 2009 2225
8. T.-M. Ou, Y.-J. Lu, J.-H. Tan, Z.-S. Huang, K.-Y. Wong, and L.-Q. Gu ChemMedChem 3 2008 690
9. J.L. Huppert, and S. Balasubramanian Nucleic Acids Res. 35 2007 406
10. Y. Qin, and L.H. Hurley Biochimie 90 2008 10049
11. A. Siddiqui-Jain, C.L. Grand, D.J. Bearss, and L.H. Hurley Proc. Natl. Acad. Sci. U.S.A. 99 2002 11593
12. S. Rankin, A.P. Reszka, J. Huppert, M. Zloh, G.N. Parkinson, A.K. Todd, S. Ladame, S. Balasubramanian, and S. Neidle J. Am. Chem. Soc. 127 2005 10584
13. S. Cogoi, M. Paramasivam, V. Filichev, I. Géci, E.B. Pedersen, and L.E. Xodo J. Med. Chem. 52 2009 564
14. Y. Qin, E.M. Rezler, V. Gokhale, D. Sun, and L.H. Hurley Nucleic Acid Res. 35 2007 7698
15. S. Balasubramanian, L.H. Hurley, and S. Neidle Nat. Rev. Drug Disc. 10 2011 261
16. T.A. Brooks, S. Kendrick, and L.H. Hurley FEBS J. 277 2010 3459
17. S. Neidle Therapeutic Applications of Quadruplex Nucleic Acids 2011 Academic Press San Diego
18. S. Cogoi, M. Paramasivam, A. Membrino, K.K. Yokoyama, and L.E. Xodo J. Biol. Chem. 285 2010 22003
19. 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
20. R.V. Brown, F.L. Danford, V. Gokhale, L.H. Hurley, and T.A. Brooks J. Biol. Chem. 286 2011 41018
21. J. Amato, B. Pagano, N. Borbone, G. Oliviero, V. Gabelica, E.D. Pauw, S. D'Errico, V. Piccialli, M. Varra, C. Giancola, G. Piccialli, and L. Mayol Bioconjug. Chem. 22 2011 654
22. S. Kumari, A. Bugaut, J.L. Huppert, and S. Balasubramanian Nat. Chem. Biol. 3 2007 218
23. K. Halder, M. Wieland, and J.S. Hartig Nucleic Acid Res. 37 2009 6811
24. See for example: S. Kumari, A. Bugaut, and S. Balasubramanian Biochemistry 47 2008 12664
25. A. Arora, and B. Suess RNA Biol. 8 2011 802
26. G.N. Parkinson, M.P. Lee, and S. Neidle Nature 417 2002 876
27. A.T. Phan, V. Kuryavyi, K.N. Luu, and D.J. Patel Nucleic Acids Res. 35 2007 6517
28. A. Ambrus, D. Chen, J. Dai, T. Bialis, R.A. Jones, and D. Yang Nucleic Acids Res. 34 2006 2723
29. K.W. Lim, S. Amrane, S. Bouaziz, W. Xu, Y. Mu, D.J. Patel, K.N. Luu, and A.T. Phan J. Am. Chem. Soc. 131 2009 4301
30. A.T. Phan FEBS J. 277 2010 1107
31. A.T. Phan, V. Kuryavyi, H.Y. Gaw, and D. Patel J. Nat. Chem. Biol. 1 2005 167
32. A.T. Phan, V. Kuryavyi, S. Burge, S. Neidle, and D.J. Patel J. Am. Chem. Soc. 129 2007 4386
33. S.T. Hsu, P. Varnai, A. Bugaut, A.P. Reszka, S. Neidle, and S. Balasubramanian J. Am. Chem. Soc. 131 2009 13399
34. D. Wei, G.N. Parkinson, A.P. Reszka, and S. Neidle Nucleic Acids Res. 2012 10.1093/nar/gks023
35. 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
36. R.J. Harrison, S.M. Gowan, L.R. Kelland, and S. Neidle Bioorg. Med. Chem. Lett. 9 1999 2463
37. P.J. Perry, M.A. Read, R.T. Davies, S.M. Gowan, A.P. Reszka, A.A. Wood, L.R. Kelland, and S. Neidle J. Med. Chem. 42 1999 2679
38. M. Read, R.J. Harrison, B. Romagnoli, F.A. Tanious, S.H. Gowan, A.P. Reszka, W.D. Wilson, L.R. Kelland, and S. Neidle Proc. Natl. Acad. Sci. U.S.A. 98 2001 4844
39. H.Y. Han, C.L. Cliff, and L.H. Hurley Biochemistry 38 1999 6981
40. F.X.G. Han, R.T. Wheelhouse, and L.H. Hurley J. Am. Chem. Soc. 121 1999 3561
41. K. Shin-ya, K. Wierzba, K. Matsuo, T. Ohtani, Y. Yamada, K. Furihata, Y. Hayakawa, and H. Seto J. Am. Chem. Soc. 123 2001 1262
42. S.M. Gowan, R. Heald, M.F.G. Stevens, and L.R. Kelland Mol. Pharmacol. 60 2001 981
43. E. Salvati, C. Leonetti, A. Rizzo, M. Scarsella, M. Mottolese, R. Galati, I. Sperduti, M.F. Stevens, M. D'Incalci, M. Blasco, G. Chiorino, S. Bauwens, B. Horard, E. Gilson, A. Stoppacciaro, G. Zupi, and A. Biroccio J. Clin. Invest 117 2007 3236
44. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P. Feeney J. Adv. Drug Del. Rev. 23 1997 3
45. D. Drygin, A. Siddiqui-Jain, S. O'Brien, M. Schwaebe, A. Lin, J. Bliesath, C.B. Ho, C. Proffitt, K. Trent, J.P. Whitten, J.K. Lim, D. Von Hoff, K. Anderes, and W.G. Rice Cancer Res. 50 2009 7653
46. 2]-TAMRA]. The stock solution of fluorescence-tagged F21T (Eurogentec, UK) in water (20 μM) was diluted to 400 nM using FRET buffer (50 mM potassium cacodylate, pH 7.4), and annealed by heating at 85 °C for 5 min followed by cooling to room temperature over 5 hrs. Fluorescence readings were taken at intervals of 0.5 °C over the range 30-100 °C, with a constant temperature maintained for 30 s prior to each reading.
47. A. Benz, V. Singh, T.U. Mayer, and J.S. Hartig ChemBioChem 12 2011 1422
48. http://pubchem.ncbi.nlm.nih.gov/ was accessed with the NSC numbers of the compounds to obtain their biological assay information (accessed Nov 2011).
49. P.C. Nair, and M.E. Sobhia J. Chem. Inform. Modeling 2008 1891 48
50. D.H. Qin, R. Sullivan, W.F. Berkowitz, R. Bittman, and S.A. Rotenberg J. Med. Chem. 43 2000 1413
51. G.L. Newton, N. Buchmeier, J.J. La Clair, and R.C. Fahey Bioorg. Med. Chem. 19 2011 3956
52. M.J. Weiss, J.R. Wong, C.S. Ha, R. Bleday, R.R. Salem, G.D. Steele, and L.B. Chen Proc. Natl. Acad. Sci. U.S.A. 84 1987 5444
53. N.A. Castle, D.G. Haylett, J.M. Morgan, and D.H. Jenkinson Eur. J. Pharmacol. 236 1993 201
54. B.F. Cain, G.J. Atwell, and R.N. Seelye J. Med. Chem. 12 1969 199
55. B. Festy, and M. Daune Biochemistry 12 1973 4827
56. D.L. Trump, K.D. Tutsch, J.K.V. Willson, S. Remick, K. Simon, D. Alberti, J. Grem, J. Koeller, and D.C. Tormey Cancer Res. 47 1987 3895
57. F.F. Ebetino Heterocycles 21 1984 436
58. S.M. Sondhi, A. Magan, and J.W. Lown Bull. Chem. Soc. Japan 65 1992 579
59. W. Fayad, M. Fryknäs, S. Brnjic, M.H. Olofsson, R. Larsson, and S. Linder PLoS ONE 4 2009 e7238
60. Y. Zhang, L. He, L. Meng, W. Luo, and X. Xu Cancer Lett. 262 2008 103
61. Y. Zhang, L. He, and Y. Zhou Phytomedicine 15 2008 112
62. L. Pieters, T. DeBruyne, B. VanPoel, R. Vingerhoets, J. Totte, D. VandenBerghe, and A. Vlietinck Phytomedicine 2 1995 17
63. B.H. Porrasreyes, W.H. Lewis, J. Roman, L. Simchowitz, and T.A. Mustoe Proc. Soc. Exp. Biol. Med. 203 1993 18
64. B.K. Sinha, R.M. Philen, R. Sato, and R.L. Cysyk J. Med. Chem. 20 1977 1528
65. S. St. George, J.V. Bishop, R.G. Titus, and C.P. Selitrennikoff Antimicrob. Agents Chemother. 50 2006 474
66. J. Booth, E. Boyland, and A. Gellhorn Cancer Chemother. Rep. Pt. 1 43 1964 11
67. D.W. Yesair, and C. Hofook Cancer Res. 28 1968 314
68. J.H. Burchenal, M.S. Lyman, J.R. Purple, V. Coley, S. Smith, and E. Bucholz Cancer Chemother. Rep. Pt. 1 19 1962 19
69. D.T.J. Liley, P.M. Wiggins, and B.C. Baguley Eur. J. Cancer Clin. Oncol. 25 1989 1287
70. A.W. Braithwaite, and B.C. Baguley Biochemistry 19 1980 1101
71. S.M. Gowan, J.R. Harrison, L. Patterson, M. Valenti, M.A. Read, S. Neidle, and L.R. Kelland Mol. Pharmacol. 61 2002 1154
72. A.M. Burger, F. Dai, C.M. Schultes, A.P. Reszka, M.J. Moore, J.A. Double, and S. Neidle Cancer Res. 65 2005 1489
73. W.C. Drewe, R. Nanjunda, M. Gunaratnam, M. Beltran, G.N. Parkinson, A.P. Reszka, W.D. Wilson, and S. Neidle J. Med. Chem. 51 2008 7751
74. M.C. Wenlock, R.P. Austin, P. Barton, A.M. Davis, and P.D. Leeson J. Med. Chem. 46 2003 1250
75. N.H. Campbell, G.N. Parkinson, A.P. Reszka, and S. Neidle J. Am. Chem. Soc. 130 2008 6722
76. G.N. Parkinson, F. Cuenca, and S. Neidle J. Mol. Biol. 381 2008 1154
77. G.W. Collie, S. Sparapani, G.N. Parkinson, and S. Neidle J. Am. Chem. Soc. 133 2011 2721