Synthesis, structural characterisation and quadruplex DNA binding studies of a new gold(III) pyrazolylpyridine complex

Chemistry - A European Journal

Volumn 16, Issue 12, 2010, Pages 3613-3616

  Suntharalingam, Kogularamanan ^a   Gupta, Deepali ^b   Sanz Miguel, Pablo J ^b   Lippert, Bernhard ^b   Vilar, Ramon ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Bioinorganic chemistry; Coordination chemistry; Gold; Quadruplex DNA; Telomere

Indexed keywords

BIOINORGANIC CHEMISTRY; CD SPECTROSCOPY; CHARACTERISATION; CIRCULAR DICHROISM; COMPLEX DISPLAYS; COORDINATION CHEMISTRY; DISPLACEMENT ASSAY; DNA BINDING STUDIES; DNA STRUCTURE; DNA-BINDING PROPERTIES; INTERCALATORS; QUADRUPLEX STRUCTURES; TELOMERES; TELOMERIC DNA;

BINDING ENERGY; BIOCHEMISTRY; COORDINATION REACTIONS; DICHROISM; DNA; GENES; GOLD; GOLD COMPOUNDS; SURFACE PLASMON RESONANCE;

COMPLEXATION;

COORDINATION COMPOUND; DNA; GOLD; GUANINE QUADRUPLEX; PYRAZOLE DERIVATIVE; PYRAZOLOPYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; X RAY CRYSTALLOGRAPHY;

CIRCULAR DICHROISM; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; DNA; G-QUADRUPLEXES; GOLD; MOLECULAR CONFORMATION; PYRAZOLES; PYRIDINES;

EID: 77949752068     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903501     Document Type: Article

References (36)

1. Quadruplex Nucleic Acids (Eds.: S. Neidle, S. Balasubramanian), RSC, Cambridge, 2006.
2. a) N. H. Campbell, G. N. Parkinson, Methods 2007, 43, 252;
3. b) S. Neidle, G.N. Parkinson, Biochimie 2008, 90, 1184;
4. c) D.J. Patel, A. T. Phan, V. Kuryavyi, Nucleic Acids Res. 2007, 35, 7429;
5. d) S. Neidle, Curr. Opin. Struct. Biol. 2009, 19, 239.
6. S. Balasubramanian, S. Neidle, Curr. Opin. Chem. Biol. 2009, 13, 345.
7. a) J. L. .Huppert, S. Balasubramanian, Nucleic Acids Res. 2006, 35, 406;
8. b) A. K. Todd, S. M. Haider, G. N. Parkinson, S. Neidle, Nucleic Acids Res. 2007, 35, 5799.
9. a) A. Rangan, O. Y. Fedoroff, L. H. Hurley, J. Biol. Chem. 2001, 276, 4640;
10. b) A. Siddiqui-Jain, C. L. Grand, D. J. Bearss, L. H. Hurley, Proc. Natl. Acad. Sci. USA 2002, 99, 11593;
11. c) H. Fernando, A. P. Reszka, J. Huppert, S. Ladame, S. Rankin, A. R. Venkitaraman, S. Neidle, S. Balasubramanian, Biochemistry 2006, 45, 7854;
12. d) Y. Qin, L. H. Hurley, Biochimie 2008, 90,1149.
13. a) N. W. Kim, M. A. Piatyszek, K. R. Prowse, C. B. Harley, M. D. West, P. L. Ho, G. M. Coviello, W. E. Wright, S. L. Weinrich, J. W. Shay, Science 1994, 266, 2011;
14. b) M. A. Blasco, Eur. J. Cell Biol. 2003, 82, 441;
15. c) D. Sun, B. Thompson, B. E. Cathers, M. Salazar, S. M. Kerwin, J. O. Trent, T. C. Jenkins, S. Neidle, L. H, Hurley, J. Med. Chem. 1997, 40, 2113;
16. d) A. De Cian, L. Lacroix, C. Douarre, N. Temime-Smaali, C. Trentesaux, J.-F. Riou, J. -L. Mergny, Biochimie 2008, 90,131.
17. a) A. Arola, R. Vilar, Curr. Top. Med, Chem. 2008, 8, 1405;
18. b) D. Monchaud, J.-P. Teulade-Fichou, Org. Biomol. Chem. 2008, 6, 627.
19. See, for example: a) J. E. Reed, A. A. Arnal, S. Neidle, R. Vilar, J. Am. Chem. Soc. 2006, 128, 5992;
20. b) K. Suntharalingam, A.J. P. White, R. Vilar, Inorg. Chem. 2009, 48, 9427;
21. c) J. E. Reed, S. Neidle, R. Vilar, Chem. Commun. 2007, 4366;
22. d) D.-F. Shi, R. T. Wheelhouse, D. Sun, L. H. Hurley, J. Med. Chem, 2001, 44, 4509;
23. e) H. Bertrand, D. Monchaud, A. De Cian, R. Guillot, J.-L. Mergny, M.-P. Teulade-Fichou, Org. Biomol. Chem. 2007, 5, 2555;
24. f) C. Rajput, R. Rutkaite, L. Swanson, I. Haq, J. A. Thomas, Chem. Eur. J. 2006, 12, 4611;
25. g) D.-L. Ma, C.-M. Che, S.-C. Yan, J. Am. Chem, Soc. 2009,131, 1835.
26. Given the possibility of tautomer equilibria, the more general formulation of the ligand as 2-(3′-pyrazolyl) pyridine seems more appropriate than the systematic name in use (i.e., 2-(1 H-pyrazol-3-yl)pyridine) . Moreover, the ligand may adopt different rotamer forms by rotating about the central C2-C3′ bond.
27. See, for example: W. R. Thiel, J. Eppinger, Chem. Eur. J. 1997, 3, 696-705.
28. See, for example: a) M. D. Ward, J. S. Fleming, E. Psillakis, J. C. Jeffrey, J. A. McCleverty, Acta Crystallogr. Sect. C 1998, 54, 609-612;
29. b) S.-Y. Chang, J. Kavitha, S.-W. Li, C.-S. Hsu, Y. Chi, Y.-S. Yeh, P.T. Chou, G.-H. Lee, A. J. Carty, Y.-T. Tao, C.-H. Chien, Inorg. Chem. 2006, 45, 137-146;
30. c) S.-Y. Chang, J. R. Chen, Y. Chi, Y.-M. Cheng, G.-H. Lee, C.-M. Jiang, P.-T. Chou, Inorg. Chem. 2007, 46, 11202-11212;
31. d) C.-S. Liu, J.-R. Li, C.-Y Li, J.-J. Wang, X.-H. Bu, Inorg. Chim. Acta 2007, 360, 2532-2540.
32. See, for example: W. Micklitz, B. Lippert, G. Müller, P. Mikulcik, J. Riede, Inorg. Chim. Acta 1989, 165, 57-64.
33. 50) is determined.
34. J. E. Redman, Methods 2007, 43, 302.
35. S. Paramasivan, I. Rujan, P. H. Bolton, Methods 2007, 43, 324.
36. A. Siddiqui-Jain, C. L. Grand, D. J. Bearss, L. H. Hurley, Proc. Natl. Acad. Sci. USA 2002, 99, 11593.