Electrochemical Oxidation of Flavonoids and Interaction with DNA on the Surface of Supramolecular Ionic Liquid Grafted on Graphene Modified Glassy Carbon Electrode

Document Type : Research Article

Authors

1 Department of Chemistry, Faculty of Science, Science & Research Branch, Islamic Azad University, Tehran, I.R. IRAN

2 Food and Drug Control Reference Laboratories, 408-Valiasr Street, Tehran, I.R. IRAN

Abstract

The study of the interaction between DNA and small molecules such as drugs is one of the current general interest and importance. In this paper, the electrochemical investigation of the interaction between some flavonoids such as rutin, quercetin, and hesperidin with dsDNA on the surface of Supramolecular Ionic Liquid grafted on the Graphene Oxide Modified Glassy Carbon Electrode (SIL-GO/GCE) is reported for the first time. The apparent binding constant (K) of the interaction between flavonoids and dsDNA was calculated using the current titrations. The apparent binding constants (K) of rutin, quercetin and hesperidin were calculated to be 4.3×105, 2.1×105 and 9.2×1-6 M-1, respectively. Furthermore, the electrochemical behavior of rutin on the surface of SIL-GO/GCE was studied in details using cyclic voltammetry and linear sweep voltammetry.  The mechanism of the electrochemical redox reaction of rutin was proposed. When DNA was added into flavonoid solutions, their cathodic peak currents were decreased with few changes in the peak potentials. Furthermore, the interaction between rutin and bovine serum albuminwas studied using differential pulse voltammetry. In conclusion, the SIL-GO/GCE provides a promising platform for the study of the interaction between DNA and small molecules.

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[1] Tian X., Li F., Zhua L., Ye B., Study On the Electrochemical Behavior of Anticancer Herbal Drug Rutin and Its Interaction with DNA, J. Electroanal. Chem., 621: 1–6 (2008).
[2] Li H., Mei W.J., Xu Z.H., Pang D.W., Ji L.N., Lin Z.H., Electrochemistry Of a Novel Monoruthenated Porphyrin and Its Interaction with DNA, J. Electroanal. Chem., 600: 243-250 (2007).
[3] Li C., Liu S.L., Guo L.H., Chen D.P., A New Chemically Amplified Electrochemical System for DNA Detection in Solution, Electrochem. Commun., 7: 23-28 (2005).
[4] Singh B., Laffir F., Dickinson C., McCormac T., Dempsey E., Carbon Supported Cobalt and Nickel Based Nanomaterials for Direct Uric Acid Determination, Electroanalysis, 23: 79-89 (2011).
[5] Hegde N.R., Kumara Swamy B.E., Shetti N.P., Nandibewoor S.T., Electro-oxidation and Determination of Gabapentin at Gold Electrode, J. Electroanal. Chem., 635: 51-57 (2009).
[7] Hosseini H., Ahmar H., Dehghani A., Bagheri A., Fakhari A.R., Amini M.M., Au-SH-SiO2 Nanoparticles Supported on Metal-organic framework (Au-SH-SiO2@Cu-MOF) as a Sensor for Electrocatalytic Oxidation and Determination of Hydrazine, Electrochim. Acta, 88: 301-309 (2013).
[10] Wang F., Xu Y., Zhao J., Hu S., Electrochemical Oxidation of Morin and Interaction with DNA, Bioelectrochemistry, 70: 356–362 (2007).
[11] Zhang J.J., Wang B., Li Y.F., Jia W.L., Cui H., Wanga H.S., Electrochemical Study on DNA Damage Based on the Direct Oxidation of 8-Hydroxydeoxyguanosine at an Electrochemically Modified Glassy Carbon Electrode, Electroanalysis, 20: 1684–1689 (2008).
[13] Kauffmann J.M., Vire J.C., Extraction—Spectrophotometric Determination of Nickel with 4-chloro-2-nitroso-1-naphthol and Crystal Violet, Anal. Chim. Acta, 273: 329–334 (1993).
[14] Russo A., Acquaviva R., Campisi A., Sorrenti V., Di Giacomo C., Virgata G., Barcellona M.L., Vanella A., Bioflavonoids as Antiradicals, Antioxidants and DNA Cleavage Protectors, Cell Biol. Toxicol. 16: 91-98 (2000).
[15] Bohm H., Boeing H., Hempel J., Raab B., Kroke A., Flavonols, Flavone and Anthocyanins as Natural Antioxidants of Food and Their Possible Role in the Prevention of Chronic Diseases, Z Ernahrungswiss. 37: 147-163 (1998).
[16] Temerk Y.M., Ibrahim M.S., Kotb M., Schuhmann W., Interaction of Antitumor Flavonoids with dsDNA in the Absence and Presence of Cu(II), Anal. Bioanal. Chem., 405: 3839–3846 (2013).
[17] Kang J., Zhuo L., Lu X., Liu H., Zhang M., Wu H., Electrochemical Investigation on Interaction Between DNA with Quercetin and Eu–Qu3 Complex, J. Inorganic Biochemistry, 98: 79–86 (2004).
[18] Zatloukalová M., Křen V., Gažák R., Kubala M., Trouillas P., Ulrichová J., Electrochemical Investigation of Flavonolignans and Study of Their Interactions with DNA in the Presence of Cu(II), Bioelectrochemistry, 82: 117–124  (2011).
[19] Chen D., Feng H., Li J., Graphene Oxide: Preparation, Functionalization, and Electrochemical Applications, Chem. Rev., 112: 6027−6053 (2012).
[20] Georgakilas V., Otyepka M., Bourlinos A.B., Chandra V., Kim N., Kemp K.C., Hobza P., Zboril R., Kim K.S., Functionalization of Graphene: Covalent and Non-covalent Approaches, Derivatives and Applications, Chem. Rev., 112: 6156−6214 (2012).
[21] Lotya M., King P.J., Khan U., De S., Coleman J.N., High-Concentration, Surfactant-Stabilized Graphene Dispersions, ACS nano, 4: 3155–3162 (2010).
[22] Patil A.J., Vickery J.L., Scott T.B., Mann S., Aqueous Stabilization and Self-Assembly of Graphene Sheets into Layered Bio-Nanocomposites Using DNA, Advanc. Mater., 21: 3159–3164 (2009).
[23] Shih C.J., Lin S., Strano M.S., Blankschtein D., Understanding the Stabilization of Liquid-Phase-Exfoliated Graphene in Polar Solvents: Molecular Dynamics Simulations and Kinetic Theory of Colloid Aggregation, J. Am. Chem. Soc., 132: 14638–14648 (2010).
[24] Lonkar S.P., Bobenrieth A., Winter J.D., Gerbaux P., Raquez J.-M., Dubois P., A Supramolecular Approach Toward Organo-dispersible Graphene and Its Straightforward Polymer Nanocomposites, J. Mater. Chem., 22: 18124-18126 (2012).
[25] Ji Q., Honma I., Paek S.-M., Akada M., Hill J.P., Vinu A., Ariga K., Layer-by-Layer Films of Graphene and Ionic Liquids for Highly Selective Gas Sensing, Angew. Chem. Int. Ed.,  49: 9737–9739 (2010).
[26] Hasan, K.U., Sandberg, M.O, Nur, O, Willander, M., Polycation Stabilization of Graphene Suspensions, Nano. Res. Lett., 6: 493-498 (2011).
[27] Zhou X., Wu T., Ding K., Hu B., Hou M., Han B., Dispersion of Graphene Sheets in Ionic liquid [bmim][PF6] Stabilized by an Ionic Liquid Polymer, Chem. Commun., 46: 386-388 (2010).
[28] Gao F., Qi X., Cai X., Wang Q., Gao F., Sun W., Electrochemically Reduced Graphene Modified Carbon Ionic Liquid Electrode for the Sensitive Sensing of Rutin., Thin Solid Films, 520: 5064–5069 (2012).
[29] Bard A.J., Faulkner L.R., “Electrochemical Methods, Fundamentals and Applications”, John Wiley & Sons Inc., New York, (2001).
[30] Pang D.W., Abruna H.D., Micromethod for the Investigation of the Interactions Between DNA and Redox-Active Molecules. Anal. Chem, 70: 3162–3169 (1998).
[31] Rodriguez M., Bard A.J., Electrochemical Studies of the Interaction of Metal Chelates with DNA. Anal. Chem., 62: 2658–2662 (1990).
[32] Temerk Y.M., Ibrahim M.S., Kotb M., Voltammetric and Spectroscopic Studies on Binding of Antitumor Morin, Morin-Cu complex and Morin-beta-cyclodextrin with DNA, Spectrochim. Acta A, 71: 1830–1836 (2009).