Synthesis, CMC determination, and intercalative binding interaction with nucleic acid of a surfactant–copper(II) complex with modified phenanthroline ligand (dpq)

References

• Ahmad, A., Asad, S. F., Singh, S., & Hadi, S. M. (2000). DNA breakage by resveratrol and Cu(II): Reaction mechanism and bacteriophage inactivation. Cancer Letters, 154, 29–37.10.1016/S0304-3835(00)00351-7
   PubMed Web of Science ®Google Scholar
• Ahsan, H., & Hadi, S. M. (1998). Strand scission in DNA induced by curcumin in the presence of Cu(II). Cancer Letters, 124, 23–30.10.1016/S0304-3835(97)00442-4
   PubMed Web of Science ®Google Scholar
• Ambika, S., Arunachalam, S., Arun, R., & Premkumar, K. (2013). Synthesis, nucleic acid binding, anticancer and antimicrobial activities of polymer–copper(ii) complexes containing intercalative phenanthroline ligand(DPQ). RSC Advances, 3, 16456–16468.10.1039/c3ra42512f
   Web of Science ®Google Scholar
• Badawi, A. M., Mekawias, M., Mohamed, M. Z., & Khowdairy, M. M. (2007). Surface and antitumor activity of some novel metal-based cationic surfactants. Journal of Cancer Research Therapeutics, 3, 198–206.
   PubMedGoogle Scholar
• Barton, J. K., Danishefsky, A., & Goldberg, J. (1984). Tris(phenanthroline)ruthenium(II): Stereoselectivity in binding to DNA. Journal of the American Chemical Society, 106, 2172–2176.10.1021/ja00319a043
   Web of Science ®Google Scholar
• Baskic, D., Popovic, S., Ristic, P., & Arsenijevic, N. N. (2006). Analysis of cycloheximide-induced apoptosis in human leukocytes: Fluorescence microscopy using annexin V/propidium iodide versus acridin orange/ethidium bromide. Cell Biology International, 30, 924–932.10.1016/j.cellbi.2006.06.016
   PubMed Web of Science ®Google Scholar
• Berners-Price, S. J., & Sadler, P. J. (1996). Coordination chemistry of metallodrugs: Insights into biological speciation from NMR spectroscopy. Coordination Chemical Reviews, 151, 1–40.
   Web of Science ®Google Scholar
• Carta, A., Sanna, P., Gherardini, G., Usai, D., & Zanetti, S. (2001). Novel functionalized pyrido[2,3-g]quinoxalinones as antibacterial, antifungal and anticancer agents. Farmaco, 56, 33–938.
   PubMedGoogle Scholar
• Carter, M. T., Rodriguez, M., & Bard, A. J. (1989). Voltammetric studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2ʹ-bipyridine. Journal of the American Chemical Society, 111, 8901–8911.10.1021/ja00206a020
   Web of Science ®Google Scholar
• Carter, P. J., Cheng, C. C., & Thorp, H. H. (1988). Oxidation of DNA and RNA by oxoruthenium(IV) metallointercalators: Visualizing the recognition properties of dipyridophenazine by high-resolution electrophoresis. Journal of American Chemical Society, 120, 632–642.
   Web of Science ®Google Scholar
• Chauhan, M., Banerjee, K., & Arjmand, F. (2007). DNA binding studies of novel copper(II) complexes containing l-tryptophan as chiral auxiliary: In vitro antitumor activity of Cu−Sn2 complex in human neuroblastoma cells. Inorganic Chemistry, 46, 3072–3082.10.1021/ic061753a
   PubMed Web of Science ®Google Scholar
• Chen, L. M., Liu, J., Chen, J. C., Tan, C. P., Shi, S., Zheng, K. C., & Ji, L. N. (2008). Synthesis, characterization, DNA-binding and spectral properties of complexes [Ru(L)4(dppz)]2+ (L = Im and MeIm). Journal of Inorganic Biochemistry, 102, 330–341.10.1016/j.jinorgbio.2007.09.006
   PubMed Web of Science ®Google Scholar
• Collins, J. G., Sleeman, A. D., Aldrich-Wright, J. R. A., Greguric, I., & Hambley, T. W. (1998). A 1H NMR study of the DNA binding of ruthenium(II) polypyridyl complexes. Inorganic Chemistry, 37, 3133–3141.10.1021/ic971194v
   Web of Science ®Google Scholar
• Coyle, B., Kinsella, P., McCann, M., Devereux, M., O’Connor, R. O., Clynes, M., & Kavanagh, K. (2004). Induction of apoptosis in yeast and mammalian cells by exposure to 1,10-phenanthroline metal complexes. Toxicology in Vitro, 18, 63–70.10.1016/j.tiv.2003.08.011
   PubMed Web of Science ®Google Scholar
• Drummond, T. G., Hill, M. G., & Barton, J. K. (2003). Electrochemical DNA sensors. Nature Biotechnology, 21, 1192–1199.10.1038/nbt873
   PubMed Web of Science ®Google Scholar
• El-Gendy, A. A., El-Meligie, S., El-Ansary, A., & Ahmedy, A. M. (1995). Synthesis of some quinoxaline derivatives containing indoline-2,3-dione or thiazolidinone residue as potential antimicrobial agents. Archives of Pharmacal Research, 18, 44–47.10.1007/BF02976507
   Google Scholar
• Galindo-Murillo, R., Ruíz-Azuara, L., Moreno-Esparza, R., & Cortés-Guzmán, F. (2011). Molecular recognition between DNA and a copper-based anticancer complex. Physical Chemistry Chemical Physics, 14, 15539–15546.
   Web of Science ®Google Scholar
• Garcı́a-Raso, A., Fiol, J. J., López-Zafra, A. L., Mata, I., Espinosa, E., & Molins, E. (2000). Synthesis of Zn N-salicylidene-l-aminoacidatos: X-ray structure of [(N-salicylidene-l-alaninato)(aqua)zinc(II)]·0.25H2O and [(N-salicylidene-l-valinato)(aqua)zinc(II)]. Polyhedron, 19, 673–680.10.1016/S0277-5387(00)00302-8
   Web of Science ®Google Scholar
• Gokce, C., & Gup, R. (2012). Synthesis and characterisation of Cu(II), Ni(II), and Zn(II) complexes of furfural derived from aroylhydrazones bearing aliphatic groups and their interactions with DNA. Chemical Papers, 67, 1293–1303.
   Web of Science ®Google Scholar
• González-Álvarez, M., Pascual-Álvarez, A., Del Castillo Agudo, L., Castiñeiras, A., Liu-González, M., Borrás, J., & Alzuet-Piña, G. (2013). Mixed-ligand copper(ii)–sulfonamide complexes: Effect of the sulfonamide derivative on DNA binding, DNA cleavage, genotoxicity and anticancer activity. Dalton Transactions, 42, 10244–10259.10.1039/c3dt50416f
   PubMed Web of Science ®Google Scholar
• González-Pérez, A., Del Castillo, J. L., Czapkiewicz, J., & Rodrı́guez, J. R. (2004). Thermodynamics of micellization of decyldimethylbenzylammonium bromide in aqueous solution. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 232, 183–189.10.1016/j.colsurfa.2003.10.018
   Web of Science ®Google Scholar
• Hadi, S. M., Bhat, S. H., Azmi, A. S., Hanif, S., Shamim, U., & Ullah, M. F. (2007). Oxidative breakage of cellular DNA by plant polyphenols: A putative mechanism for anticancer properties. Seminars in Cancer Biology, 17, 370–376.10.1016/j.semcancer.2007.04.002
   PubMed Web of Science ®Google Scholar
• Hathaway, B. J. (1987). Comprehensive coordination chemistry. In G. Wilkinson, R. D. Gillared, & A. Mecleverty (Eds.), Comprehensive coordination chemistry (Vol. 5, p. 583–774). Oxford: Pergfamon.
   Google Scholar
• Hazarika, P., Bezbaruah, B., Das, P., Medhi, O. K., & Medhi, C. (2011). A model study on the stacking interaction of phenanthroline ligand with nucleic acid base pairs: An ab initio, MP2 and DFT studies. Journal of Biophysical Chemistry, 2, 152–157.
   Google Scholar
• Hazarika, P., Bezbaruah, B., Gogoi, A., Das, P., Medhi, O. K., & Medhi, C. (2009). The selectivity of nucleobases in DNA binding by Ru(phenanthroline)3 complex. Indian Journal of Chemistry, 48A, 1235–1241.
   Google Scholar
• Hudson, B. P., Dupureur, C. M., & Barton, J. K. (1995). 1H NMR structural evidence for the sequence-specific design of an intercalator: DELTA-alpha.-[Rh[(R,R)-Me2trien]phi]3+ bound to d(GAGTGCACTC)2. Journal of the American Chemical Society, 117, 9379–9380.10.1021/ja00141a041
   Web of Science ®Google Scholar
• Kelly, J. M., Tossi, A. B., McConnell, D. J., & OhUigin, C. (1985). A study of the interactions of some polypyridylruthenium(II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation. Nucleic acids Research, 13, 6017–6034.10.1093/nar/13.17.6017
   PubMed Web of Science ®Google Scholar
• Khan, N. S., & Hadi, S. M. (1998). Structural features of tannic acid important for DNA degradation in the presence of Cu(II). Mutagenesis, 13, 271–274.10.1093/mutage/13.3.271
   PubMed Web of Science ®Google Scholar
• Kishu, T. (2012). Antifungal activity of organometallic complexes of cholic acid. Der Pharmacia Lettre, 4, 1567–1573.
   Google Scholar
• Kratz, F., & Schutte, M. T. (1998). Anticancer metal-complexes and tumor targeting strategies. Cancer Journal, 11, 176–179.
   Web of Science ®Google Scholar
• Lakowicz, J. R., & Weber, G. (1973). Quenching of fluorescence by oxygen. Probe for structural fluctuations in macromolecules. Biochemistry, 12, 4161–4170.10.1021/bi00745a020
   PubMed Web of Science ®Google Scholar
• Liu, F. R., Wang, K. Z., Bai, G. Y., Zhang, Y. G., & Gao, L. H. (2004). The pH-induced emission switching and interesting DNA-binding properties of a novel dinuclear ruthenium(II) complex. Inorganic Chemistry, 43, 1799–1806.10.1021/ic035109x
   PubMed Web of Science ®Google Scholar
• Long, E. C., & Barton, J. K. (1990). On demonstrating DNA intercalation. Accounts of Chemical Research, 23, 271–273.10.1021/ar00177a001
   Web of Science ®Google Scholar
• Maheswari, P. U., & Palaniandavar, M. (2004). DNA binding and cleavage properties of certain tetrammine ruthenium(II) complexes of modified 1,10-phenanthrolines – Effect of hydrogen-bonding on DNA-binding affinity. Journal of Inorganic Biochemistry, 98, 219–230.10.1016/j.jinorgbio.2003.09.003
   PubMed Web of Science ®Google Scholar
• Ming, L. J., & Epperson, J. D. (2002). Metal binding and structure–activity relationship of the metalloantibiotic peptide bacitracin. Journal of Inorganic Biochemistry, 91, 46–58.10.1016/S0162-0134(02)00464-6
   PubMed Web of Science ®Google Scholar
• Morris, M. L., & Busch, D. H. (1960). Infrared spectra studies on the cis and trans isomers of diacidobis-(ethylenediamine)-cobalt(III) complexes. Journal of the American Chemical Society, 82, 1521–1524.10.1021/ja01492a001
   Web of Science ®Google Scholar
• Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55–63.10.1016/0022-1759(83)90303-4
   PubMed Web of Science ®Google Scholar
• Myers, D. (1999). Surfaces, interfaces, and colloids (2nd ed.). New York, NY: Wiley-VCH, ISBN 0-471-33060-4.
   Google Scholar
• Nagaraj, K., & Arunachalam, S. (2013). Studies on DNA binding of a double-chain surfactant cobalt(III) complex containing 2,2′-bipyridine ligand. Zeitschrift für Physikalische Chemie, 227, 1–19.
   Web of Science ®Google Scholar
• Nagaraj, K., & Arunachalam, S. (2013). Binding of a double-chain surfactant cobalt(III) complex to CT DNA: Effect of β-cyclodextrin in the medium. International Journal of Biological Macromolecules, 62, 273–280.
   PubMed Web of Science ®Google Scholar
• Nehru, S., Arunachalam, S., Arun, R., & Premkumar, K. (2013). Polymer-cobalt(III) complexes: Structural analysis of metal chelates on DNA interaction and comparative cytotoxic activity. Journal of Biomolecular Structure and Dynamics, 1–13.
   Google Scholar
• Nordén, B., & Tjerneld, F. (1976). Binding of inert metal complexes to deoxyribonucleic acid detected by linear dichroism. FEBS Letters, 67, 368–370.10.1016/0014-5793(76)80566-2
   PubMed Web of Science ®Google Scholar
• Nusselder, J. J. H., & Engberts, J. B. F. N. (1992). Toward a better understanding of the driving force for micelle formation and micellar growth. Journal of Colloid and Interface Science, 148, 353–361.10.1016/0021-9797(92)90174-K
   Web of Science ®Google Scholar
• Osinsky, I., Levitin, L., Bubnovskaya, A., Sigan, I., & Ganusevich, N. (2004). Selectivity of effects of redox active cobalt(III) complexes on tumor tissue. Experimental Oncology, 26, 140–144.
   PubMed Web of Science ®Google Scholar
• Patel, M. N., Dosi, P. A., & Bhatt, B. S. (2011). DNA interaction, free radical scavenging and in-vitro antibacterial activity of drug-based copper(II) complexes. Applied Organometallic Chemistry, 25, 653–660.
   Web of Science ®Google Scholar
• Patel, R. N., Singh, N., Patel, D. K., & Gundla, V. L. N. (2007). Synthesis, characterization and superoxide dismutase studies of square pyramidal copper(II) complexes with bi and tridentate polyamine ligands. Indian Journal of Chemistry, 46A, 422–427.
   Google Scholar
• Pradeep, C. P., Acharias, P. S. Z., & Das, S. K. (2005). Synthesis and characterization of a chiral dimeric copper(II) complex: Crystal structure of [Cu2(m-Cl)2(HL)2] × H2O(H2L = S-(-)-2-[(2-hydroxy-1-phenyl-ethylimino)-methyl]-phenol). Journal of Chemical Science, 117, 133–137.
   Web of Science ®Google Scholar
• Pyle, A. M., & Barton, J. K. (1990). Progress in inorganic chemistry. In S. J. Lippard (Ed.), In progress in inorganic chemistry (Vol. 38, p. 413–465). New York, NY: Wiley Interscience.
   Google Scholar
• Pyle, A. M., Rehman, J. P., Meshoyrer, R., Kumar, C. V., Turro, N. J., & Barton, J. K. (1989). Mixed-ligand complexes of ruthenium(II): Factors governing binding to DNA. Journal of American Chemical Society, 111, 3053–3063.
   Google Scholar
• Rahman, A., Shahabuddin, Hadi, S. M., Parish, J. H., & Ainley, K. (1989). Strand scission in DNA induced by quercetin and Cu(II): Role of Cu(I) and oxygen free radicals. Carcinogenesis, 10, 1833–1839.10.1093/carcin/10.10.1833
   PubMed Web of Science ®Google Scholar
• Reichmann, M. F., Rice, S. A., Thomas, C. A., & Doty, P. (1954). A further examination of the molecular weight and size of desoxypentose nucleic acid. Journal of the American Chemical Society, 76, 3047–3053.10.1021/ja01640a067
   Web of Science ®Google Scholar
• Sanna, P., Carta, A., Loriga, M., Zanetti, S., & Sechi, L. (1999). Synthesis of 3,6,7-substituted-quinoxalin-2-ones for evaluation of antimicrobial and anticancer activity. Part 2. Il Farmaco, 54, 161–168.10.1016/S0014-827X(99)00010-5
   PubMedGoogle Scholar
• Santra, B. K., Reddy, P. A. N., Neelakanta, G., Mahadevan, S., Nethaji, M., & Chakravarty, A. R. (2002). Oxidative cleavage of DNA by a dipyridoquinoxaline copper(II) complex in the presence of ascorbic acid. Journal of Inorganic Biochemistry, 89, 191–196.10.1016/S0162-0134(01)00418-4
   PubMed Web of Science ®Google Scholar
• Sasikala, K., & Arunachalam, S. (2012). Antimicrobial activity, spectral studies and CMC determination of some surfactant-copper (II) complexes. Journal of Chemical, Biological and Physical Sciences, 2, 708–718.
   Google Scholar
• Sasmal, A., Saha, S., Gómez-García, C. J., Desplanches, C., Garribba, E., Bauzá, A., … Scott, S. (2013). Reversible switching of the electronic ground state in a pentacoordinated Cu(II) complex. Chemical Communications, 49, 7806–7808.10.1039/c3cc44276d
   PubMed Web of Science ®Google Scholar
• Satyanarayana, S., Dabrowiak, J. C., & Chaires, J. B. (1992). Neither .DELTA.- nor .LAMBDA.-tris(phenanthroline)ruthenium(II) binds to DNA by classical intercalation. Biochemistry, 31, 9319–9324.10.1021/bi00154a001
   PubMed Web of Science ®Google Scholar
• Satyanarayana, S., Dabrowiak, J. C., & Chaires, J. B. (1993). Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: Mode and specificity of binding. Biochemistry, 32, 2573–2584.10.1021/bi00061a015
   PubMed Web of Science ®Google Scholar
• Selvi, P., & Palaniandavar, M. (2002). Spectral, viscometric and electrochemical studies on mixed ligand cobalt(III) complexes of certain diimine ligands bound to calf thymus DNA. Inorganica Chimica Acta, 337, 420–428.10.1016/S0020-1693(02)01112-X
   Web of Science ®Google Scholar
• Shahabadi, N., Darabi, F., Maghsudi, M., & Kashanian, S. (2010). DNA binding and gel electrophoresis studies of a copper (II) complex containing mixed aliphatic and aromatic dinitrogen ligands. DNA and Cell Biology, 29, 329–336.10.1089/dna.2009.1001
   PubMed Web of Science ®Google Scholar
• Shakir, M., Azam, M., Ullah, M. F., & Hadi, S. M. (2011). Synthesis, spectroscopic and electrochemical studies of N,N-bis[(E)-2-thienylmethylidene]-1,8-naphthalenediamine and its Cu(II) complex: DNA cleavage and generation of superoxide anion. Journal of Photochemistry and Photobiology B: Biology, 104, 449–456.10.1016/j.jphotobiol.2011.05.003
   PubMed Web of Science ®Google Scholar
• Shamim, U., Hanif, S., Ullah, M. F., Azmi, A. S., Bhat, S. H., & Hadi, S. M. (2008). Plant polyphenols mobilize nuclear copper in human peripheral lymphocytes leading to oxidatively generated DNA breakage: Implications for an anticancer mechanism. Free Radical Research, 42, 764–772.10.1080/10715760802302251
   PubMed Web of Science ®Google Scholar
• Sigman, D. S., Mazumder, A., & Perrin, D. M. (1993). Chemical nucleases. Chemical Reviews, 93, 2295–2316.10.1021/cr00022a011
   Web of Science ®Google Scholar
• Spector, D. L., Goldman, R. D., & Leinwand, L. A. (1998). Culture and biochemical analysis of cells. In D. L. Spector, R. D. Goldman, & L. A. Leinwand (Eds.), Cell: A laboratory manual (Vol. 1, 15.1–15.24). Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
   Google Scholar
• Srinivas, C., Kumar, C. N. S. P., Rao, V. J., & Palaniappan, S. (2008). Green approach for the synthesis of quinoxaline derivatives in water medium using reusable polyaniline-sulfate salt catalyst and sodium laurylsulfate. Catalysis Letters, 121, 291–296.10.1007/s10562-007-9335-y
   Web of Science ®Google Scholar
• Staszewska, A., Stefanowicz, P., & Szewczuk, Z. (2005). Direct solid-phase synthesis of quinoxaline-containing peptides. Tetrahedron Letters, 46, 5525–5528.10.1016/j.tetlet.2005.06.047
   Web of Science ®Google Scholar
• Watson, R. T., Desai, N., Wildsmith, J., Wheeler, J. F. N., & Kane-Maguire, N. A. P. (1999). Interaction of Cr(diimine)33+ complexes with DNA. Inorganic Chemistry, 38, 2683–2687.10.1021/ic980857l
   Web of Science ®Google Scholar
• Wolfe, A., Shimer, G. H., & Meehan, T. (1987). Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry, 26, 6392–6396.10.1021/bi00394a013
   PubMed Web of Science ®Google Scholar
• Zakharova, L., Valeeva, F., Zakharov, A., Ibragimova, A., Kudryavtseva, L., & Harlampidi, H. (2003). Micellization and catalytic activity of the cetyltrimethylammonium bromide–Brij 97–water mixed micellar system. Journal of Colloid and Interface Science, 263, 597–605.10.1016/S0021-9797(03)00343-6
   PubMed Web of Science ®Google Scholar
• Zhao, G., Lin, H., Zhu, S., Sun, H., & Chen, Y. (1998). Dinuclear palladium(II) complexes containing two monofunctional [Pd(en)(pyridine)Cl]+ units bridged by Se or S. Synthesis, characterization, cytotoxicity and kinetic studies of DNA-binding. Journal of Inorganic Biochemistry, 70, 219–226.10.1016/S0162-0134(98)10019-3
   PubMed Web of Science ®Google Scholar
• Zou, X. H., Ye, B. H., Li, H., Zhang, Q. L., Cao, H., Liu, J.-G., … Li, X. Y. (2001). The design of new molecular “light switches” for DNA. Journal of Biological Inorganic Chemistry, 6, 143–147.
   PubMed Web of Science ®Google Scholar