New insights into the mechanism of the DNA/doxorubicin interaction

Journal of Physical Chemistry B

Volumn 118, Issue 5, 2014, Pages 1288-1295

  Pérez Arnaiz, Cristina ^a   Busto, Natalia ^a   Leal, José M ^a   García, Begoña ^a  

^a UNIVERSITY OF BURGOS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE; BI-FUNCTIONAL; CALF THYMUS DNA (CT-DNA); GROOVE BINDING; ISOTHERMAL TITRATION CALORIMETRY; KINETIC STUDY; RELAXATION MEASUREMENTS; TWO-STEP MECHANISMS;

DIFFERENTIAL SCANNING CALORIMETRY;

DNA;

CALF THYMUS DNA; DNA; DOXORUBICIN; DOXORUBICIN DNA; DOXORUBICIN-DNA; POLY(DEOXYADENYLATE DEOXYTHYMIDYLATE); POLYDEOXYRIBONUCLEOTIDE; POLY[DEOXY(CYTIDYLATE GUANYLATE)];

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; DNA ADDUCT; KINETICS; METABOLISM; PH; THERMODYNAMICS; TRANSITION TEMPERATURE; VISCOSITY;

ANIMALS; CATTLE; DNA; DNA ADDUCTS; DOXORUBICIN; HYDROGEN-ION CONCENTRATION; KINETICS; POLY DA-DT; POLYDEOXYRIBONUCLEOTIDES; THERMODYNAMICS; TRANSITION TEMPERATURE; VISCOSITY;

EID: 84893841091     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp411429g     Document Type: Article

References (33)

1. Carvalho, C.; Santos, R. X.; Cardoso, S.; Correia, S.; Oliveira, P. J.; Santos, M. S.; Moreira, P. I. Doxorubicin: The good, the bad and the ugly effect Curr. Med. Chem. 2009, 16, 3267-3285
2. Gewirtz, D. A. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics Adriamycin and Daunorubicin Biochem. Pharmacol. 1999, 57, 727-741
3. Pommier, Y.; Leo, E.; Zhang, H.-L.; Marchand, C. DNA Topoisomerases and Their Poisoning by Anticancer and Antibacterial Drugs Chem. Biol. 2010, 17, 421-433
4. Minotti, G.; Menna, P.; Salvatorelli, E.; Cairo, G.; Gianni, L. Anthracyclines: Molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity Pharmacol. Rev. 2004, 56, 185-229
5. Yang, X. L.; Wang, A. H. J. Structural studies of atom-specific anticancer drugs acting on DNA Pharmacol. Ther. 1999, 83, 181-215
6. Aubel-Sadron, G.; Londos-Gagliardi, D. Daunorubicin and doxorubicin, anthracycline antibiotics, a physicochemical and biological review Biochimie 1984, 66, 333-52
7. Bodley, A.; Liu, L. F.; Israel, M.; Seshadri, R.; Koseki, Y.; Ciuliani, F. C.; Kirschenbaum, S.; Silber, R.; Potmesil, M. DNA topoisomerase II-mediated interaction of doxorubicin and daunorubicin congeners with DNA Cancer Res. 1989, 49, 5969-78
8. Rizzo, V.; Sacchi, N.; Menozzi, M. Kinetic studies of anthracycline-DNA interaction by fluorescence stopped flow confirm a complex association mechanism Biochemistry 1989, 28, 274-82
9. Förster, W.; Stutter, E. Interaction of anthracycline antibiotics with biopolymers: 9. Comparative study of the interaction kinetics of daunomycin, adriamycin and iremycin with DNA Int. J. Biol. Macromol. 1984, 6, 114-24
10. Bogojeski, J.; Bugarcic, Z. D.; Puchta, R.; van, E. R. Kinetic studies on the reactions of different bifunctional platinum(II) complexes with selected nucleophiles Eur. J. Inorg. Chem. 2010, 5439-5445
11. Chaires, J. B.; Satyanarayana, S.; Suh, D.; Fokt, I.; Przewloka, T.; Priebe, W. Parsing the free energy of anthracycline antibiotic binding to DNA Biochemistry 1996, 35, 2047-2053
12. Zunino, F.; Gambetta, R.; Di, M. A.; Velcich, A.; Zaccara, A.; Quadrifoglio, F.; Crescenzi, V. The interaction of adriamycin and its β anomer with DNA Biochim. Biophys. Acta, Nucleic Acids Protein Synth. 1977, 476, 38-46
13. Frederick, C. A.; Williams, L. D.; Ughetto, G.; Van, d. M. G. A.; Van, B. J. H.; Rich, A.; Wang, A. H. J. Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin Biochemistry 1990, 29, 2538-49
14. Ren, J. S.; Chaires, J. B. Sequence and structural selectivity of nucleic acid binding ligands Biochemistry 1999, 38, 16067-16075
15. DuVernay, V. H., Jr.; Pachter, J. A.; Crooke, S. T. Deoxyribonucleic acid binding studies on several new anthracycline antitumor antibiotics. Sequence preference and structure-activity relationships of marcellomycin and its analogues as compared to adriamycin Biochemistry 1979, 18, 4024-30
16. Cohen, G.; Eisenberg, H. Viscosity and sedimentation study of sonicated DNA-proflavine complexes Biopolymers 1969, 8, 45-55
17. Rigler, R.; Rabl, C. R.; Jovin, T. M. Temperature-jump apparatus for fluorescence measurements Rev. Sci. Instrum. 1974, 45, 580-8
18. Di, M. A.; Casazza, A. M.; Dasdia, T.; Necco, A.; Pratesi, G.; Rivolta, P.; Velcich, A.; Zaccara, A.; Zunino, F. Changes of activity of daunorubicin, adriamycin and stereoisomers following the introduction or removal of hydroxyl groups in the amino sugar moiety Chem.-Biol. Interact. 1977, 19, 291-302
19. Menozzi, M.; Valentini, L.; Vannini, E.; Arcamone, F. Self-association of doxorubicin and related compounds in aqueous solution J. Pharm. Sci. 1984, 73, 766-70
20. Garcia, B.; Leal, J. M.; Ruiz, R.; Biver, T.; Secco, F.; Venturini, M. Change of the Binding Mode of the DNA/Proflavine System Induced by Ethanol J. Phys. Chem. B 2010, 114, 8555-8564
21. Cory, M.; McKee, D. D.; Kagan, J.; Henry, D. W.; Miller, J. A. Design, synthesis, and DNA binding properties of bifunctional intercalators. Comparison of polymethylene and diphenyl ether chains connecting phenanthridine J. Am. Chem. Soc. 1985, 107, 2528-36
22. Biver, T.; Boggioni, A.; Secco, F.; Turriani, E.; Venturini, M.; Yarmoluk, S. Influence of cyanine dye structure on self-aggregation and interaction with nucleic acids: A kinetic approach to TO and BO binding Arch. Biochem. Biophys. 2007, 465, 90-100
23. Busto, N.; Garcia, B.; Leal, J. M.; Secco, F.; Venturini, M. The mode of binding ACMA-DNA relies on the base-pair nature Org. Biomol. Chem. 2012, 10, 2594-2602
24. Chaires, J. B.; Dattagupta, N.; Crothers, D. M. Kinetics of the daunomycin-DNA interaction Biochemistry 1985, 24, 260-267
25. Biver, T.; De, B. A.; Secco, F.; Venturini, M.; Yarmoluk, S. Cyanine dyes as intercalating agents: Kinetic and thermodynamic studies on the DNA/Cyan40 and DNA/CCyan2 systems Biophys. J. 2005, 89, 374-383
26. Record, M. T., Jr.; Lohman, T. M.; De, H. P. Ion effects on ligand-nucleic acid interactions J. Mol. Biol. 1976, 107, 145-58
27. Baguley, B. C.; Falkenhaug, E. M. The interaction of ethidium with synthetic double-stranded polynucleotides at low ionic strength Nucleic Acids Res. 1978, 5, 161-71
28. Chaires, J. B. Calorimetry and thermodynamics in drug design Annu. Rev. Biophys. 2008, 37, 135-151
29. Lozano, H. J.; Garcia, B.; Busto, N.; Leal, J. M. Interaction of Thionine with Triple-, Double-, and Single-Stranded RNAs J. Phys. Chem. B 2013, 117, 38-48
30. Scatchard, G. The attraction of proteins for small molecules and ions Ann. N.Y. Acad. Sci. 1949, 51, 660-72
31. Prue, J. E. Ionic Equilibria. The International Encyclopedia of Physical Chemistry and Chemical Physics, Topic 15: Equilibrium Properties of Electrolyte Solutions; Pergamon Press: Oxford, U.K., 1966; Vol. 3.
32. Guntelberg, E. Interaction of ions Z. Phys. Chem. 1926, 123, 199-247
33. Jelesarov, I.; Bosshard, H. R. Isothermal titration calorimetry and differential scanning calorimetry as complementary tools to investigate the energetics of biomolecular recognition J. Mol. Recognit. 1999, 12, 3-18