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Journal of Nucleic Acids
Volume 2010, Article ID 247137, 7 pages
http://dx.doi.org/10.4061/2010/247137
Research Article

Selective Binding of Distamycin A Derivative to G-Quadruplex Structure [d(TGGGGT)]4

1Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte don Melillo, 84084 Fisciano, Italy
2Dipartimento di Chimica “P. Corradini”, Università di Napoli Federico II, Via Cintia, 80126 Napoli, Italy
3Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy
4Dipartimento di Chimica Farmaceutica e Tossicologica, Università di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy

Received 21 January 2010; Accepted 7 March 2010

Academic Editor: Jean Louis Mergny

Copyright © 2010 Bruno Pagano et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. S. Burge, G. N. Parkinson, P. Hazel, A. K. Todd, and S. Neidle, “Quadruplex DNA: sequence, topology and structure,” Nucleic Acids Research, vol. 34, no. 19, pp. 5402–5415, 2006. View at Publisher · View at Google Scholar · View at Scopus
  2. J. L. Huppert and S. Balasubramanian, “Prevalence of quadruplexes in the human genome,” Nucleic Acids Research, vol. 33, no. 9, pp. 2908–2916, 2005. View at Publisher · View at Google Scholar · View at Scopus
  3. J. E. Johnson, J. S. Smith, M. L. Kozak, and F. B. Johnson, “In vivo veritas: using yeast to probe the biological functions of G-quadruplexes,” Biochimie, vol. 90, no. 8, pp. 1250–1263, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. Y. Qin and L. H. Hurley, “Structures, folding patterns, and functions of intramolecular DNA G-quadruplexes found in eukaryotic promoter regions,” Biochimie, vol. 90, no. 8, pp. 1149–1171, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. S. Neidle and G. N. Parkinson, “The structure of telomeric DNA,” Current Opinion in Structural Biology, vol. 13, no. 3, pp. 275–283, 2003. View at Publisher · View at Google Scholar · View at Scopus
  6. G. Laughlan, A. I. H. Murchie, D. G. Norman et al., “The high-resolution crystal structure of a parallel-stranded guanine tetraplex,” Science, vol. 265, no. 5171, pp. 520–524, 1994. View at Google Scholar · View at Scopus
  7. N. W. Kim, M. A. Piatyszek, K. R. Prowse et al., “Specific association of human telomerase activity with immortal cells and cancer,” Science, vol. 266, pp. 2011–2015, 1994. View at Google Scholar
  8. J. W. Shay and W. E. Wright, “Telomerase therapeutics for cancer: challenges and new directions,” Nature Reviews Drug Discovery, vol. 5, no. 7, pp. 577–584, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. B. Pagano and C. Giancola, “Energetics of quadruplex-drug recognition in anticancer therapy,” Current Cancer Drug Targets, vol. 7, no. 6, pp. 520–540, 2007. View at Publisher · View at Google Scholar · View at Scopus
  10. J.-F. Riou, “G-quadruplex interacting agents targetting the telomeric G-overhang are more than simple telomerase inhibitors,” Current Medicinal Chemistry, vol. 4, no. 5, pp. 439–443, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. S. Neidle, “The structures of quadruplex nucleic acids and their drug complexes,” Current Opinion in Structural Biology, vol. 19, no. 3, pp. 239–250, 2009. View at Publisher · View at Google Scholar · View at Scopus
  12. L. Martino, A. Virno, B. Pagano et al., “Structural and thermodynamic studies of the interaction of distamycin A with the parallel quadruplex structure [d(TGGGGT)]4,” Journal of the American Chemical Society, vol. 129, no. 51, pp. 16048–16056, 2007. View at Publisher · View at Google Scholar · View at Scopus
  13. N. Zaffaroni, S. Lualdi, R. Villa et al., “Inhibition of telomerase activity by a distamycin derivative: effects on cell proliferation and induction of apoptosis in human cancer cells,” European Journal of Cancer, vol. 38, no. 13, pp. 1792–1801, 2002. View at Publisher · View at Google Scholar · View at Scopus
  14. B. Pagano, A. Virno, C. A. Mattia, L. Mayol, A. Randazzo, and C. Giancola, “Targeting DNA quadruplexes with distamycin A and its derivatives: an ITC and NMR study,” Biochimie, vol. 90, no. 8, pp. 1224–1232, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. B. Pagano, C. A. Mattia, A. Virno, A. Randazzo, L. Mayol, and C. Giancola, “Thermodynamic analysis of quadruplex DNA-drug interaction,” Nucleosides, Nucleotides and Nucleic Acids, vol. 26, no. 6-7, pp. 761–765, 2007. View at Publisher · View at Google Scholar · View at Scopus
  16. M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, and R. E. Dickerson, “The molecular origin of DNA-drug specificity in netropsin and distamycin,” Proceedings of the National Academy of Sciences of the United States of America, vol. 82, no. 5, pp. 1376–1380, 1985. View at Google Scholar · View at Scopus
  17. M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, and R. E. Dickerson, “Binding of an antitumor drug to DNA netropsin and C-G-C-G-A-A-T-T-BrC-G-C-G,” Journal of Molecular Biology, vol. 183, no. 4, pp. 553–563, 1985. View at Google Scholar · View at Scopus
  18. L. A. Marky and K. J. Breslauer, “Origins of netropsin binding affinity and specificity: correlations of thermodynamic and structural data,” Proceedings of the National Academy of Sciences of the United States of America, vol. 84, no. 13, pp. 4359–4363, 1987. View at Google Scholar · View at Scopus
  19. I. Haq, “Thermodynamics of drug-DNA interactions,” Archives of Biochemistry and Biophysics, vol. 403, no. 1, pp. 1–15, 2002. View at Publisher · View at Google Scholar · View at Scopus
  20. C. R. Cantor, M. M. Warshaw, and H. Shapiro, “Oligonucleotide interactions. 3. Circular dichroism studies of the conformation of deoxyoligonucleotides,” Biopolymers, vol. 9, no. 9, pp. 1059–1077, 1970. View at Google Scholar · View at Scopus
  21. G. Di Pietro, G. Giannini, E. M. Iafrate et al., “N-formimidoyl analogues of distamycin,” Journal of the Chemical Society, Perkin Transactions 1, no. 12, pp. 1333–1335, 1996. View at Google Scholar · View at Scopus
  22. D. Rentzeperis, L. A. Marky, T. J. Dwyer, B. H. Geierstanger, J. G. Pelton, and D. E. Wemmer, “Interaction of minor groove ligands to an AAATT/AATTT site: correlation of thermodynamic characterization and solution structure,” Biochemistry, vol. 34, no. 9, pp. 2937–2945, 1995. View at Publisher · View at Google Scholar · View at Scopus
  23. T. L. Hwang and A. J. Shaka, “Water suppression that works. Excitation sculpting using arbitrary wave-forms and pulsed-field gradients,” Journal of Magnetic Resonance A, vol. 112, pp. 275–279, 1995. View at Google Scholar
  24. C. Dalvit, “Efficient multiple-solvent suppression for the study of the interactions of organic solvents with biomolecules,” Journal of Biomolecular NMR, vol. 11, no. 4, pp. 437–444, 1998. View at Google Scholar · View at Scopus
  25. D. R. Hare, D. E. Wemmer, S.-H. Chou, G. Drobny, and B. R. Reid, “Assignment of the non-exchangeable proton resonances of d(C-G-C-G-A-A-T-T-C-G-C-G) using two-dimensional nuclear magnetic resonance methods,” Journal of Molecular Biology, vol. 171, no. 3, pp. 319–336, 1983. View at Google Scholar · View at Scopus
  26. R. M. Wartell, J. E. Larson, and R. D. Wells, “Netropsin. A specific probe for AT regions of duplex deoxyribonucleic acid,” The Journal of Biological Chemistry, vol. 249, no. 21, pp. 6719–6731, 1974. View at Google Scholar · View at Scopus
  27. J. G. Pelton and D. E. Wemmer, “Binding modes of distamycin A with d(CGCAAATTTGCG)2 determined by two-dimensional NMR,” Journal of the American Chemical Society, vol. 112, no. 4, pp. 1393–1399, 1990. View at Google Scholar · View at Scopus
  28. C. Zimmer, “Effects of the antibiotics netropsin and distamycin A on the structure and function of nucleic acids,” Progress in Nucleic Acid Research and Molecular Biology, vol. 15, pp. 285–318, 1975. View at Google Scholar · View at Scopus
  29. A. Randazzo, A. Galeone, and L. Mayol, “1H-NMR study of the interaction of distamycin A and netropsin with the parallel stranded tetraplex [d(TGGGGT)]4,” Chemical Communications, vol. 11, pp. 1030–1031, 2001. View at Google Scholar
  30. M. J. Cocco, L. A. Hanakahi, M. D. Huber, and N. Maizels, “Specific interactions of distamycin with G-quadruplex DNA,” Nucleic Acids Research, vol. 31, no. 11, pp. 2944–2951, 2003. View at Publisher · View at Google Scholar · View at Scopus
  31. B. Pagano, C. A. Mattia, and C. Giancola, “Applications of isothermal titration calorimetry in biophysical studies of G-quadruplexes,” International Journal of Molecular Sciences, vol. 10, no. 7, pp. 2935–2957, 2009. View at Publisher · View at Google Scholar · View at Scopus
  32. J. B. Chaires, “A thermodynamic signature for drug-DNA binding mode,” Archives of Biochemistry and Biophysics, vol. 453, no. 1, pp. 24–29, 2006. View at Publisher · View at Google Scholar · View at Scopus