Thermodynamics and kinetic studies in the binding interaction of cyclic naphthalene diimide derivatives with double stranded DNAs

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 15, 2015, Pages 4769-4776

  Islam, Md Monirul ^a   Fujii, Satoshi ^a   Sato, Shinobu ^a   Okauchi, Tatsuo ^a   Takenaka, Shigeori ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Bis intercalative binding; Cyclic naphthalene diimide derivatives; Double stranded DNA; Entropy dependence binding; Hydrophobic interaction

Indexed keywords

ADENINE; CYCLIC NAPHTHALENE DIIMIDE DERIVATIVE; CYTOSINE; DNA; DNA TOPOISOMERASE; DOUBLE STRANDED DNA; GUANINE; IMIDE; THYMINE; UNCLASSIFIED DRUG; CALF THYMUS DNA; NAPHTHALENE DERIVATIVE; NAPHTHALENEDIIMIDE; POLY(D(A-T))2; POLYDEOXYRIBONUCLEOTIDE;

ARTICLE; BASE PAIRING; BINDING AFFINITY; CIRCULAR DICHROISM; DISSOCIATION; DNA DENATURATION; DNA DRUG COMPLEX; DRUG DNA BINDING; DRUG SYNTHESIS; ENTROPY; ENZYME ASSAY; FLOW KINETICS; HYDROPHOBICITY; KINETICS; MOLECULAR INTERACTION; SIGNAL PROCESSING; STOICHIOMETRY; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY; ANIMAL; BOVINE; CHEMISTRY; METABOLISM; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; CATTLE; CIRCULAR DICHROISM; DNA; DNA TOPOISOMERASES, TYPE I; IMIDES; KINETICS; NAPHTHALENES; POLYDEOXYRIBONUCLEOTIDES; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS;

EID: 84937523349     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.05.046     Document Type: Article

References (39)

1. J.B. Chaires Curr. Opin. Struct. Biol. 8 1998 314
2. G.M. Blackburn, M.J. Gait, D. Loakes, and D.M. Williams Nucleic Acids in Chemistry and Biology 3rd ed. 2006 RSC Publication Thomas Graham House, Science Park, Milton Road, Cambridge CB4 0WF, UK
3. J.B. Chaires Arch. Biochem. Biophys. 453 2006 26
4. V.M. Guelev, M.S. Cubberley, M.M. Murr, R.S. Lokey, and B.L. Iverson Design, synthesis, and characterization of polyintercalating ligands J.B. Chaires, M.J. Waring, Methods in Enzymol. 2001 Academic Press New York 556 570
5. R.S. Lokey, Y. Kwok, V. Guelev, C.J. Pursell, L.H. Hurley, and B.L. Iverson J. Am. Chem. Soc. 119 1997 7202
6. G.G. Holman, M. Zewail-Foote, A.R. Smith, K.A. Johnson, and B.L. Iverson Nat. Chem. 3 2011 875
7. A.R. Smith, and B.L. Iverson Am. Chem. Soc. 135 2013 12783
8. Y. Chu, D.W. Hoffman, and B.L. Iverson J. Am. Chem. Soc. 131 2009 3499
9. Y. Chu, S. Sorey, D.W. Hoffman, and B.L. Iverson J. Am. Chem. Soc. 129 2007 1304
10. J. Lee, V. Guelev, S. Sorey, D.W. Hoffman, and B.L. Iverson J. Am. Chem. Soc. 126 2004 14036
11. I. Czerwinska, S. Sato, B. Juskowiak, and S. Takenaka Bioorg. Med. Chem. 22 2014 2593
12. Y. Esaki, M.M. Islam, S. Fujii, S. Sato, and S. Takenaka Chem. Commun. 50 2014 5967
13. A. Milelli, V. Tumiatti, M. Micco, M. Rosini, G. Zuccari, L. Raffaghello, G. Bianchi, V. Pistoia, J.F. Diaz, B. Pera, C. Trigili, I. Barasoain, C. Musetti, M. Toniolo, C. Sissi, S. Alcaro, F. Moraca, M. Zini, C. Stefanelli, and A. Minarini Eur. J. Med. Chem. 57 2012 417
14. S.M. Hampel, A. Sidibe, M. Gunaratnam, J.F. Riou, and S. Neidle Bioorg. Med. Chem. Lett. 20 2010 6459
15. F.A. Tanious, S.F. Yen, and W.D. Wilson Biochemistry 30 1991 1813
16. J.D. McGhee, and P.H. von Hippel J. Mol. Biol. 86 1974 469
17. Y. Sato, S. Nishizawa, K. Yoshimoto, T. Seino, T. Ichihashi, K. Morita, and N. Teramae Nucleic Acids Res. 37 2009 1411
18. W.C. Tse, and D.L. Boger Chem. Biol. 11 2004 1607
19. Z.R. Liu, K.H. Hecker, and R.L. Rill J. Biomol. Struct. Dyn. 14 1996 331
20. R.E. McKnight Insights into the Relative DNA Binding Affinity and Preferred Binding Mode of Homologous Compounds Using Isothermal Titration Calorimetry (ITC) A.A. Elkordy, Applications of Calorimetry in a Wide Context-Differential Scanning Calorimetry, Isothermal Titration Calorimetry and Microcalorimetry 2013 InTech publication Rijeka, Croatia 129 152
21. P.H. vonHippel, N.P. Johnson, and A.H. Marcus Biopolymers 99 2013 923
22. N. Huang, K.B. Nilesh, and D.M. Alexander PNAS 100 2003 68
23. N.K. Banavali J. Am. Chem. Soc. 135 2013 8274
24. K. Nakatani, S. Hagihara, Y. Goto, A. Kobori, M. Hagihara, G. Hayashi, M. Kyo, M. Nomura, M. Mishima, and C. Kojima Chem. Biol. 1 2005 39
25. J.B. Chaires, F. Leng, T. Przewloka, I. Fokt, Y.H. Ling, R.P. Soler, and W. Priebe J. Med. Chem. 40 1997 261
26. G.G. Hu, X. Shui, F. Leng, W. Priebe, J.B. Chaires, and L.D. Williams Biochemistry 36 1997 5940
27. N. Shahabadi, and A. Fatahi J. Mol. Struct. 970 2010 90
28. I. Haq Arch. Biochem. Biophys. 403 2002 1
29. H. Becker, and B. Norden J. Am. Chem. Soc. 119 1997 5798
30. R.S. Spolar, and M.T. Reord Jr. Science 263 1994 777
31. F. Leng, J.B. Chaires, and M.J. Waring Nucleic Acids Res. 31 2003 6191
32. I. Haq, J.E. Ladbury, B.Z. Chowdhry, T.C. Jenkins, and J.B. Chaires J. Mol. Biol. 271 1997 244
33. W.D. Wilson, and F.A. Tanious Kinetic Analysis of Drug-nucleic acid Binding Modes: Absolute Rates and Effects of Salt Concentration S. Neidle, M. Waring, Molecular Aspects of Anticancer Drug-DNA Interactions Vol. 2 1994 CRC Press, MacMillan London 243 269
34. M.T. Record, C.F. Anderson, and T.M. Lohman Q. Rev. Biophys. 11 1978 103
35. R.L. Jones, A.C. Lanier, R.A. Keel, and W.D. Wilson Nucleic Acids Res. 8 1980 1613
36. W.D. Wilson, C.R. Krishnamoorthy, Y.H. Wang, and J.C. Smith Biopolymers 24 1985 1941
37. F.A. Tanious, T.C. Jenkis, S. Neidle, and W.D. Wilson Biochemistry 31 1992 11632
38. P. Peixoto, C. Bailly, and M.H. David-Cordonnier Methods Mol. Biol. 613 2010 235
39. M. Monnot, O. Mauffret, E. Lescot, and S. Fermandjian Eur. J. Biochem. 204 1992 1035