Anthraquinones quinizarin and danthron unwind negatively supercoiled DNA and lengthen linear DNA

Biochemical and Biophysical Research Communications

Volumn 444, Issue 1, 2014, Pages 50-55

  Verebová, Valéria ^a   Adamcik, Jozef ^b   Danko, Patrik ^c   Podhradský, Dušan ^c   Miškovský, Pavol ^c   Staničová, Jana ^a  

^a UNIVERSITY OF VETERINARY MEDICINE   (Slovakia)

^b ETH ZURICH   (Switzerland)

^c P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

Danthron; DNA lengthening; Intercalation; Negatively supercoiled DNA; Quinizarin

Indexed keywords

DANTHRON; DNA LENGTHENING; INTERCALATION; NEGATIVELY SUPERCOILED DNA; QUINIZARIN;

ANTHRAQUINONES; DENATURING GRADIENT GEL ELECTROPHORESIS; DNA; DNA, B-FORM; DNA, SUPERHELICAL; INTERCALATING AGENTS; MICROSCOPY, ATOMIC FORCE; NUCLEIC ACID CONFORMATION; PLASMIDS; SPECTROMETRY, FLUORESCENCE;

EID: 84893865624     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2014.01.007     Document Type: Article

References (37)

1. L.H. Hurley DNA and its associated processes as targets for cancer therapy Nat. Rev. Cancer 2 2002 188 200 (Pubitemid 37328788)
2. R. Palchaudhuri, and P.J. Hergenrother DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action Curr. Opin. Biotechnol. 18 2007 497 503
3. G. Bischoff, and S. Hoffmann DNA-binding of drugs used in medicinal therapies Curr. Med. Chem. 9 2002 312 348
4. R. Martínez, and L. Chacón-García The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work Curr. Med. Chem. 12 2005 127 151 (Pubitemid 40089830)
5. L. Strekowski, and B. Wilson Noncovalent interactions with DNA: an overview Mutat. Res. 623 2007 3 13 (Pubitemid 47368574)
6. N.J. Wheate, C.R. Brodie, J.G. Collins, S. Kemp, and J.R. Aldrich-Wright DNA intercalators in cancer therapy: organic and inorganic drugs and their spectroscopic tools of analysis Mini Rev. Med. Chem. 7 2007 627 648 (Pubitemid 47099183)
7. H. Ihmels, and D. Otto Intercalation of organic dye molecules into double-stranded DNA general principles and recent developments Top. Curr. Chem. 258 2005 161 204 (Pubitemid 44420807)
8. H. Zhou, Z. Sun, T. Hoshi, Y. Kashiwagi, J. Anzai, and G. Li Electrochemical studies of danthron and the DNA-danthron interaction Biophys. Chem. 114 2005 21 26 (Pubitemid 40403526)
9. C. Batchelor-McAuley, I.B. Dimov, L. Aldous, and R.G. Compton The electrochemistry of quinizarin revealed through its mediated reduction of oxygen Proc. Natl. Acad. Sci. USA 108 2011 19891 19895
10. M.B. Gholivand, S. Kashanian, H. Peyman, and H. Roshanfekr DNA-binding study of anthraquinone derivatives using chemometrics methods Eur. J. Med. Chem. 46 2011 2630 2638
11. C. Qiao, S. Bi, Y. Sun, D. Song, H. Zhang, and W. Zhou Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe Spectrochim. Acta, Part A 70 2008 136 143 (Pubitemid 351615106)
12. M.B. Gholivand, S. Kashanian, and H. Peyman DNA-binding, DNA cleavage and cytotoxicity studies of two anthraquinone derivatives Spectrochim. Acta, Part A 87 2012 232 240
13. D. Bhakta, and R. Siva Morindone, an anthraquinone, intercalates DNA sans toxicity: a spectroscopic and molecular modeling perspective Appl. Biochem. Biotechnol. 167 2012 885 896
14. P. Das, P.S. Guina, P.C. Mandal, M. Paul, S. Paul, and S. Das Cyclic voltammetric studies of 1,2,4-trihydroxy-9,10-anthraquinone, its interaction with calf thymus DNA and anti-leukemic activity on MOLT-4 cell lines: a comparison with anthracycline anticancer drugs J. Phys. Org. Chem. 24 2011 774 785
15. S. Mukherjee, P. Das, and S. Das Exploration of small hydroxy-9,10-anthraquinones as anthracycline analogues: physicochemical characteristics and DNA binding for comparison J. Phys. Org. Chem. 25 2012 385 393
16. P. Pristas, I. Vanat, and P. Javorský Isolation and characterization of a new restriction endonuclease, Sru30DI, from Selenomonas ruminantium Gene 158 1995 139 140
17. V. Víglasky, P. Danko, J. Adamcík, F. Valle, and G. Dietler Detection of cruciform extrusion in DNA by temperature-gradient gel electrophoresis Anal. Biochem. 343 2005 308 312 (Pubitemid 41074045)
18. J. Adamcík, V. Víglaský, F. Valle, M. Antalík, D. Podhradský, and G. Dietler Effect of bacteria growth temperature on the distribution of supercoiled DNA and its thermal stability Electrophoresis 23 2002 3300 3309 (Pubitemid 35230213)
19. V. Víglaský, M. Antalík, J. Adamcík, and D. Podhradský Early melting of supercoiled DNA topoisomers observed by TGGE Nucleic Acids Res. 28 2000 E51
20. J. Adamcik, F. Valle, G. Witz, K. Rechendorff, and G. Dietler The promotion of secondary structures in single-stranded DNA by drugs that bind to duplex DNA: an atomic force microscopy study Nanotechnology 19 2008 384016
21. J. Marek, E. Demjénová, Z. Tomori, J. Janácek, I. Zolotová, F. Valle, M. Favre, and G. Dietler Interactive measurement and characterization of DNA molecules by analysis of AFM images Cytometry A 63 2005 87 93 (Pubitemid 40224086)
22. A.A. Vetcher, A.E. McEwen, R. Abujarour, A. Hanke, and S.D. Levene Gel mobilities of linking-number topoisomers and their dependence on DNA helical repeat and elasticity Biophys. Chem. 148 2010 104 111
23. V. Víglasky, F. Valle, J. Adamcík, I. Joab, D. Podhradsky, and G. Dietler Anthracycline-dependent heat-induced transition from positive to negative supercoiled DNA Electrophoresis 24 2003 1703 1711 (Pubitemid 38088956)
24. P. Danko, A. Kozák, D. Podhradský, and V. Víglaský Analysis of DNA intercalating drugs by TGGE J. Biochem. Biophys. Methods 65 2005 89 95 (Pubitemid 41827580)
25. J.M. Edwardson, and R.M. Henderson Atomic force microscopy and drug discovery Drug Discov. Today 9 2004 64 71 (Pubitemid 38173075)
26. L.H. Pope, M.C. Davies, C.A. Laughton, C.J. Roberts, S.J. Tendler, and P.M. Williams Atomic force microscopy studies of intercalation-induced changes in plasmid DNA tertiary structure J. Microsc. 199 2000 68 78 (Pubitemid 30456741)
27. T. Banerjee, and R. Mukhopadhyay Structural effects of nogalamycin, an antibiotic antitumour agent, on DNA Biochem. Biophys. Res. Commun. 374 2008 264 268
28. J. Adamcik, J.H. Jeon, K.J. Karczewski, R. Metzler, and G. Dietler Quantifying supercoiling-induced denaturation bubbles in DNA Soft Matter 8 2012 8651 8658
29. J.E. Coury, L. McFail-Isom, L.D. Williams, and L.A. Bottomley A novel assay for drug-DNA binding mode, affinity, and exclusion number: scanning force microscopy Proc. Natl. Acad. Sci. USA 93 1996 12283 12286 (Pubitemid 26367134)
30. V. Cassina, D. Seruggia, G.L. Beretta, D. Salerno, D. Brogioli, S. Manzini, F. Zunino, and F. Mantegazza Atomic force microscopy study of DNA conformation in the presence of drugs Eur. Biophys. J. 40 2011 59 68
31. R. Kumar Senthil, K. Sasikala, and S. Arunachalam DNA Interaction of some polymer-copper(II) complexes containing 2,2′-bipyridyl ligand and their antimicrobial activities J. Inorg. Biochem. 102 2008 234 241
32. X. Yang, W.H. Liu, W.J. Jin, G.L. Shen, and R.Q. Yu DNA binding studies of a solvatochromic fluorescence probe 3-methoxybenzathrone Spectrochim. Acta, Part A 55 1999 2719 2727
33. N.S. Allen, J.F. McKellar, and S. Protopapas Lightfastness, phototendering and fluorescence of 3-methoxybenzanthrone J. Appl. Chem. Biotechnol. 27 1977 269 274
34. E.C. Long, and J.K. Barton On demonstrating DNA intercalation Acc. Chem. Res. 23 1990 271 273
35. C. Medhi, J.B. Mitchell, S.L. Price, and A.B. Tabor Electrostatic factors in DNA intercalation Biopolymers 52 1999 84 93 (Pubitemid 30429693)
36. C.A. Hunter, K.R. Lawson, J. Perkins, and C.J. Urch Aromatic interactions J. Chem. Soc., Perkin Trans. 2 2001 651 669
37. R.A. Copeland Protein-ligand binding equilibria R.A. Copeland, Enzymes: A Practical Introduction to Structure, Mechanism and Data Analysis 2000 John Wiley & Sons Inc New York 76 107