Drug–DNA interactions and their study by UV–Visible, fluorescence spectroscopies and cyclic voltametry

E.D. Gadsby, Drug–DNA Interactions and Condensations Investigation with Atomic Force Microscopy, PhD Dissertation, School of Chemistry and Biochemistry, Georgia Institute of Technology, July 2004, pp. 23–25. Harding, 1993, A P-31 NMR-study of the interaction of the antitumor active metallocene CP2MoCl2 with calf thymus DNA, FEBS Lett., 322, 291, 10.1016/0014-5793(93)81588-Q V. Gonzalez-Ruiz, A.I. Olives, M.A. Martin, P. Ribelles, M.T. Ramos, J.C. Menendez, An overview of analytical techniques employed to evidence drug–DNA interactions. Applications to the design of genosensors, in: M.A. Komorowska, S. Olsztynska-Janus (Eds.), Biomedical Engineering, Trends, Research and Technologies. In Tech, 2011, pp. 65–90. Kennard, 1993, DNA–drug interactions, Pure Appl. Chem., 65, 1213, 10.1351/pac199365061213 Hajian, 2009, Study on the interaction between doxorubicin and deoxyribonucleic acid with the use of methylene blue as a probe, J. Braz. Chem. Soc., 20, 1399, 10.1590/S0103-50532009000800003 Rauf, 2005, Electrochemical approach of anticancer drugs–DNA interaction, J. Pharmaceut. Biomed. Anal., 37, 205, 10.1016/j.jpba.2004.10.037 Snyder, 2005, Toward a greater appreciation of noncovalent chemical/DNA interactions: application of biological and computational approaches, Environ. Mol. Mutagen., 45, 100, 10.1002/em.20096 Silvestri, 2012, Tandem mass spectrometry for characterization of covalent adducts of DNA with anticancer therapeutics, Mass Spectrom Rev., 2, 1 Liu, 2011, Metal complexes as DNA intercalators, Acc. Chem. Res., 44, 349, 10.1021/ar100140e Hadjiliadis, 2009 “Antineop”, <http://faculty.swosu.edu/scott.long/phcl/antineop.htm> (retrieved 24.01.09). Rajski, 1998, DNA cross-linking agents as antitumor drugs, Chem. Rev., 98, 2723, 10.1021/cr9800199 Kondo, 2010, DNA damage induced by alkylating agents and repair pathways, J. Nucleic Acids, 2010, 1, 10.4061/2010/543531 Park, 1997, Covalent modification of N3 of guanine by (+)-CC-1065 results in protonation of the cross-strand cytosine, J. Am. Chem. Soc., 119, 629, 10.1021/ja9632264 Ni, 2006, Synchronous fluorescence, UV–visible spectrophotometric, and voltammetric studies of the competitive interaction of bis(1,10-phenanthroline)copper(II) complex and neutral red with DNA, Anal. Biochem., 352, 231, 10.1016/j.ab.2006.02.031 Lerman, 1961, Structural considerations in the interaction of DNA and acridines, J. Mol. Biol., 3, 18, 10.1016/S0022-2836(61)80004-1 Martínez, 2005, The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work, Curr. Med. Chem., 12, 127, 10.2174/0929867053363414 Shui, 2000, Effects of cationic charge on three-dimensional structures of intercalative complexes structure of a bis-intercalated DNA complex solved by MAD phasing, Curr. Med. Chem., 7, 59, 10.2174/0929867003375470 Waring, 1994, The purine 2-amino group as a critical recognition element for binding of small molecules to DNA, Gene, 149, 69, 10.1016/0378-1119(94)90414-6 Rehn, 1996, Molecular modeling of intercalation complexes of antitumor active 9-aminoacridine and a [d,e]-anellated isoquinoline derivative with base paired deoxytetranucleotides, Monatsh. Chem., 127, 645, 10.1007/BF00817256 Baginski, 1997, Electrostatic and non-electrostatic contributions to the binding free energies of anthracycline antibiotics to DNA, J. Mol. Biol., 274, 253, 10.1006/jmbi.1997.1399 Bauer, 1970, The interaction of closed circular DNA with intercalative dyes: III. Dependence of the buoyant density upon superhelix density and base composition, J. Mol. Biol., 54, 281, 10.1016/0022-2836(70)90430-4 Neidle, 1984, Structural and sequence-dependent aspects of drug intercalation into nucleic acid, CRC Crit. Rev. Biochem., 171, 73, 10.3109/10409238409110270 Keck, 1992, Unwinding of supercoiled DNA by platinum–ethidium and related complexes, J. Am. Chem. Soc., 114, 3386, 10.1021/ja00035a033 Moucheron, 1998, New DNA-binding ruthenium(II) complexes as photo-reagents for mononucleotides and DNA, J. Phys. Org. Chem., 11, 577, 10.1002/(SICI)1099-1395(199808/09)11:8/9<577::AID-POC53>3.0.CO;2-X Haq, 1995, Interaction of DELTA-and LAMBDA-[Ru(phen)2DPPZ]2+ with DNA: a calorimetric and equilibrium binding study, J. Am. Chem. Soc., 117, 4788, 10.1021/ja00122a008 Lincoln, 1998, DNA binding geometries of ruthenium(II) complexes with 1,10-phenanthroline and 2,2′-bipyridine ligands studied with linear dichroism spectroscopy. Borderline cases of intercalation, J. Phys. Chem. B, 102, 9583, 10.1021/jp9824914 Ambrosek, 2010, A theoretical study of Ru(II) polypyridyl DNA intercalators: structure and electronic absorption spectroscopy of [Ru(phen)2(dppz)]2+ and [Ru(tap)2(dppz)]2+ complexes intercalated in guanine–cytosine base pairs, J. Inorg. Biochem., 104, 893, 10.1016/j.jinorgbio.2010.04.002 Tiwari, 2011, Synthesis and DNA binding studies of Ni(II), Co(II), Cu(II) and Zn(II) metal complexes of N1, N5-bis[pyridine-2-methylene]-thiocarbohydrazone Schiff-base ligand, Spectrochim. Acta A, 79, 1050, 10.1016/j.saa.2011.04.018 Bulnes, 2009, Indirect effects modulating the interaction between DNA and a cytotoxic bisnaphthalimide reveal a two-step binding process, J. Am. Chem. Soc., 131, 7781, 10.1021/ja901505p Yeh, 1995, Biochemistry, 34, 13570, 10.1021/bi00041a037 Paul, 2012, Chemistry and biology of DNA-binding small molecules, Curr. Sci., 102, 212 Todd, 1999, Major groove binding and a “DNA-induced” fit in the intercalation of a derivative of the mixed topoisomerase I/II inhibitor DACA into DNA; X-ray structure complexed to d(CG(5BrU)ACG)2 at 1.3Å resolution, J. Med. Chem., 42, 536, 10.1021/jm980479u Janovec, 2011, Cytotoxic 3,6-bis((imidazolidinone)imino)acridines: synthesis, DNA binding and molecular modeling, Bioorg. Med. Chem., 19, 1790, 10.1016/j.bmc.2011.01.012 Mei, 1986, Chiral probe for A-form helices of DNA and RNA-tris(tetramethylphenanthroline)ruthenium(II), J. Am. Chem. Soc., 108, 7414, 10.1021/ja00283a050 Kopka, 1985, Binding of an antitumor drug to DNA: netropsin and C-G-C-G-A-A-T-T-BrC-G-C-G, J. Mol. Biol., 183, 553, 10.1016/0022-2836(85)90171-8 Haq, 2000, Drug–DNA recognition: energetics and implications for design, J. Mol. Recognit., 13, 188, 10.1002/1099-1352(200007/08)13:4<188::AID-JMR503>3.0.CO;2-1 Kelly, 1985, A study of the interactions of some polypyridylruthenium(II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation, Nucl. Acids Res., 13, 6017, 10.1093/nar/13.17.6017 Sun, 2011, A stabilizing and denaturing dual-effect for natural polyamines interacting with G-quadruplexes depending on concentration, Biochimie, 93, 1351, 10.1016/j.biochi.2011.06.007 Jaumot, 2012, Experimental methods for studying the interactions between G-quadruplex structures and ligands, Curr. Pharmaceut. Des., 18, 1900, 10.2174/138161212799958486 Wei, 2010, Spectroscopic study on the binding of porphyrins to (G4T4G4)4 parallel G-quadruplex, Biophys. Chem., 148, 51, 10.1016/j.bpc.2010.02.009 Bhadra, 1810, Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: a comparative spectroscopic and calorimetric study, Biochim. Biophys. Acta, 2011, 485 Benesi, 1949, Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc., 71, 2703, 10.1021/ja01176a030 Liu, 2002, DNA-binding and cleavage studies of macrocyclic copper(II) complexes, J. Inorg. Biochem., 91, 269, 10.1016/S0162-0134(02)00441-5 Sirajuddin, 2012, Synthesis, characterization, biological screenings and interaction with calf thymus DNA as well as electrochemical studies of adducts formed by azomethine [2-((3,5-dimethylphenylimino)methyl)phenol] and organotin(IV) chlorides, Polyhedron, 40, 19, 10.1016/j.poly.2012.03.048 Sirajuddin, 2012, Synthesis, characterization, biological screenings and interaction with calf thymus DNA of a novel azomethine 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol, Spectrochim. Acta A, 94, 134, 10.1016/j.saa.2012.03.068 Arjmand, 2011, DNA binding studies of new valine derived chiral complexes of tin(IV) and zirconium(IV), Spectrochim. Acta A, 78, 45, 10.1016/j.saa.2010.06.009 Pratviel, 1998, DNA and RNA cleavage by metal complexes, Adv. Inorg. Chem., 45, 251, 10.1016/S0898-8838(08)60027-6 Shahabadi, 2010, Multispectroscopic DNA interaction studies of a water-soluble nickel(II) complex containing different dinitrogen aromatic ligands, Tran. Met. Chem., 35, 699, 10.1007/s11243-010-9382-x Kumar, 2009, Synthesis, characterization and DNA binding and photocleavage studies of [Ru(bpy)2BDPPZ]2+, [Ru(dmb)2BDPPZ]2+ and [Ru(phen)2BDPPZ]2+ complexes and their antimicrobial activity, Appl. Organometal. Chem., 23, 409, 10.1002/aoc.1534 KaluCerovic, 2010, Synthesis, characterization and biological studies of 1-D polymeric triphenyltin(IV) carboxylates, J. Organomet. Chem., 695, 1883, 10.1016/j.jorganchem.2010.04.029 Falcioni, 2008, Interaction of tributyltin(IV) chloride and a related complex [Bu3Sn(LSM)] with rat leukocytes and erythrocytes: effect on DNA and on plasma membrane, Mutat. Res., 653, 57, 10.1016/j.mrgentox.2008.03.010 Tysoe, 1993, Spectroscopic investigation of differential binding modes of DELTA- and LAMBDA-Ru(bpy)2 (ppz)2+ with calf thymus DNA, J. Phys. Chem., 97, 1707, 10.1021/j100110a038 Zhang, 2004, A novel cytotoxic ternary copper(II) complex of 1,10-phenanthroline and l-threonine with DNA nuclease activity, J. Inorg. Biochem., 98, 2099, 10.1016/j.jinorgbio.2004.09.014 Dey, 2010, Copper(II) complex with tridentate N donor ligand: synthesis, crystal structure, reactivity and DNA binding study, Polyhedron, 29, 1583, 10.1016/j.poly.2010.01.022 Ghosh, 2010, Synthesis and reactivity studies on new copper(II) complexes: DNA binding, generation of phenoxyl radical, SOD and nuclease activities, Eur. J. Med. Chem., 45, 3770, 10.1016/j.ejmech.2010.05.026 Ghosh, 2011, Synthesis, crystal structure and DNA interaction studies on mononuclear zinc complexes, Inorg. Chim. Acta, 375, 77, 10.1016/j.ica.2011.04.035 Shujha, 2010, Diorganotin(IV) derivatives of ONO tridentate Schiff base: synthesis, crystal structure, in vitro antimicrobial, anti-leishmanial and DNA binding studies, Eur. J. Med. Chem., 45, 2902, 10.1016/j.ejmech.2010.03.015 Ju, 2011, The interesting DNA-binding properties of three novel dinuclear Ru(II) complexes with varied lengths of flexible bridges, J. Inorg. Biochem., 105, 435, 10.1016/j.jinorgbio.2010.12.004 Rehman, 2009, Synthesis, spectroscopic characterization, X-ray structures and evaluation of binding parameters of new triorganotin(IV) dithiocarboxylates with DNA, Eur. J. Med. Chem., 44, 3986, 10.1016/j.ejmech.2009.04.031 Kalanur, 2009, Electrochemical studies and spectroscopic investigations on the interaction of an anticancer drug with DNA and their analytical applications, J. Electroanal. Chem., 636, 93, 10.1016/j.jelechem.2009.09.018 Shah, 2010, Voltammetric and spectroscopic investigations of 4-nitrophenylferrocene interacting with DNA, Spectrochim. Acta A, 75, 1082, 10.1016/j.saa.2009.12.061 Lakowicz, 2006 Suh, 1995, Criteria for the mode of binding of DNA binding agents, Biorg. Med. Chem., 3, 723, 10.1016/0968-0896(95)00053-J Li, 1997, Study on the interaction between rivanol and DNA and its application to DNA assay, Spectrochim. Acta A, 53, 781, 10.1016/S1386-1425(97)00015-2 Li, 2005, Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods, Biophys. Chem., 116, 199, 10.1016/j.bpc.2005.04.009 Wu, 2011, Synthesis, structure, and DNA-binding properties of manganese(II) and zinc(II) complexes with tris (N-methylbenzimidazol-2-ylmethyl) amine ligand, Tran. Met. Chem., 36, 21, 10.1007/s11243-010-9429-z Wu, 2011, A Schiff base ligand N-(2-hydroxylacetophenone)-3-oxapentane-1,5-diamine and its nickel(II) complex: synthesis, crystal structure, antioxidation, and DNA-binding properties, Tran. Met. Chem., 36, 847, 10.1007/s11243-011-9539-2 Anbu, 2011, Electrochemical, magnetic, catalytic, DNA binding and cleavage studies of new mono and binuclear copper(II) complexes, Polyhedron, 30, 123, 10.1016/j.poly.2010.09.041 Carter, 1987, Voltammetric studies of the interaction of tris(1,10-phenanthroline)cobalt(III) with DNA, J. Am. Chem. Soc., 109, 7528, 10.1021/ja00258a046 Feng, 1997, Electrochemical studies of porphyrin interacting with DNA and determination of DNA, Anal. Chim. Acta, 344, 97, 10.1016/S0003-2670(97)00008-1 Li, 2010, Synthesis, structure and voltammetric studies of copper(II) polymer with DNA interaction: the first 1-D coordination polymer alternately bridged by oxalate and oxamidate ligands, J. Inorg. Organomet. Polym., 20, 586, 10.1007/s10904-010-9370-9 Aslanoglu, 2005, Voltammetric, UV absorption and viscometric studies of the interaction of norepinephrine with DNA, Turk. J. Chem., 29, 477 Aslanoglu, 2004, Voltammetric studies of the interaction of quinacrine with DNA, Anal. Bioanal. Chem., 380, 658, 10.1007/s00216-004-2797-5 Chu, 1998, Anal. Chim. Acta, 373, 29, 10.1016/S0003-2670(98)00362-6 Welch, 1996, J. Phys. Chem., 100, 13829, 10.1021/jp960251n Carter, 1989, J. Am. Chem. Soc., 111, 8901, 10.1021/ja00206a020 Muhammad, 2009, Organotin(IV) 4-nitrophenylethanoates: synthesis, structural characteristics and intercalative mode of interaction with DNA, J. Organomet. Chem., 694, 3431, 10.1016/j.jorganchem.2009.06.036