Abstract
Benzo[c]phenanthridine alkaloid sanguilutine was extracted and purified from the dried roots of Sanguinaria canadensis. The interaction of the positively charged iminium form of alkaloid with double-stranded DNA oligonucleotides was studied using luminescence spectroscopy. The results showed that the interaction with various double-stranded oligonucleotides was not specific to A-T or G-C base pairs; also, no preference was found for either homogeneous or heterogeneous base composition of strands. The association constants were calculated to be in the range of (1.31–14.36) × 105 M−1. The luminescence intensity response at 610 nm to low concentrations of double-stranded DNA was found to be linear and can potentially be used for the fluorometric quantification of DNA. The limit of detection was estimated to be 120 ng mL−1 of DNA (calculated by 3σ method).
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References
Adhikari, A., Hossain, M., Maiti, M., & Kumar, G. S. (2008). Energetics of the binding of phototoxic and cytotoxic plant alkaloid sanguinarine to DNA: Isothermal titration calorimetric studies. Journal of Molecular Structure, 889, 54–63. DOI: 10.1016/j.molstruc.2008.01.016.
Bai, L. P., Zhao, Z. Z., Cai, Z. W., & Jiang, Z. H. (2006). DNAbinding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine. Bioorganic & Medicinal Chemistry, 14, 5439–5445. DOI: 10.1016/j.bmc.2006.05.012.
Bai, L. P., Cai, Z. W., Zhao, Z. Z., Nakatani, K., & Jiang, Z. H. (2008a). Site-specific binding of chelerythrine and sanguinarine to single pyrimidine bulges in hairpin DNA. Analytical and Bioanalytical Chemistry, 392, 709–716. DOI: 10.1007/s00216-008-2302-7.
Bai, L. P., Hagihara, M., Jiang, Z. H., & Nakatani, K. (2008b). Ligand binding to tandem G quadruplexes from human telomeric DNA. ChemBioChem, 9, 2583–2587. DOI: 10.1002/cbic.200800256.
Bhadra, K., & Kumar, G. S. (2011a). Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design. Medicinal Research Reviews, 31, 821–862. DOI: 10.1002/med.20202.
Bhadra, K., & Kumar, G. S. (2011b). Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: A comparative spectroscopic and calorimetric study. Biochimica et Biophysica Acta (BBA) — General Subjects, 1810, 485–496. DOI: 10.1016/j.bbagen.2011.01.011.
Dostál, J., Slavík, J., Potácek, M., Marek, R., Sklenár, V., De Hoffmann, E., Rozenberg, R., Tinant, B., & Declercq, J. P. (1998). Structure and transformations of the alkaloid sanguilutine. Phytochemistry, 47, 879–885. DOI: 10.1016/s0031-9422(97)00665-1.
Dvorak, Z., Kuban, V., Klejdus, B., Hlavac, J., Vicar, J., Ulrichova, J., & Simanek, V. (2006). Quaternary benzo[c]phenanthridines sanguinarine and chelerythrine: A review of investigations from chemical and biological studies. Heterocycles, 68, 2403–2422.
Hammerová, J., Uldrijan, S., Táborská, E., & Slaninová, I. (2011). Benzo[c]phenanthridine alkaloids — compounds with high anti-proliferative activity against malignant melanoma. European Journal of Cancer, 47, S655.
Hossain, M., & Kumar, G. S. (2009). DNA binding of benzophenanthridine compounds sanguinarine versus ethidium: Comparative binding and thermodynamic profile of intercalation. Journal of Chemical Thermodynamics, 41, 764–774. DOI: 10.1016/j.jct.2008.12.008.
Hossain, M., & Kumar, G. S. (2010). Thermodynamic profiles of the DNA binding of benzophenanthridines sanguinarine and ethidium: A comparative study with sequence specific polynucleotides. Journal of Chemical Thermodynamics, 42, 1273–1280. DOI: 10.1016/j.jct.2010.05.005.
Hossain, M., Khan, A. Y., & Kumar, G. S. (2012). Study on the thermodynamics of the binding of iminium and alkanolamine forms of the anticancer agent sanguinarine to human serum albumin. Journal of Chemical Thermodynamics, 47, 90–99. DOI: 10.1016/j.jct.2011.09.026.
Janovská, M., Kubala, M., Šimánek, V., & Ulrichová, J. (2009). Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms. Analytical and Bioanalytical Chemistry, 395, 235–240. DOI: 10.1007/s00216-009-2903-9.
Janovská, M., Kubala, M., Šimánek, V., & Ulrichová, J. (2010). Fluorescence of sanguinarine: spectral changes on interaction with amino acids. Physical Chemistry Chemical Physics, 12, 11335–11341. DOI: 10.1039/b925828k.
Ji, X. H., Sun, H. X., Zhou, H. X., Xiang, J. F., Tang, Y. L., & Zhao, C. Q. (2012). The interaction of telomeric DNA and Cmyc22 G-quadruplex with 11 natural alkaloids. Nucleic Acid Therapeutics, 22, 127–136. DOI: 10.1089/nat.2012.0342.
Kosina, P., Vacek, J., Papoušková, B., Stiborová, M., Stýskala, J., Cankař, P., Vrublová, E., Vostálová, J., Šimánek, V., & Ulrichová, J. (2011). Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry. Journal of Chromatography B, 879, 1077–1085. DOI: 10.1016/j.jchromb.2011.03.023.
Kovář, J., Stejskal, J., Paulová H., & Slavík, J. (1986). Reduction of quaternary benzophenanthridine alkaloids by NADH and NADPH. Collection of Czechoslovak Chemical Communications, 51, 2626–2634.
Kyvala, M., Lubal, P., & Lukes, I. (1998). Determination of equilibrium constants with the opium computer program. In IX Spanish — Italian and mediterranean congress on thermodynamics of metal complexes SIMEC’ 98, June 2–5, 1998 (pp. 115). Girona, Spain: Universitat de Girona.
Marek, R., Toušek, J., Dostál, J., Slavík, J., Dommisse, R., & Sklenář, V. (1999). 1H and 13C NMR study of quaternary benzo[c]phenanthridine alkaloids. Magnetic Resonance in Chemistry, 37, 781–787. DOI: 10.1002/(sici)1097-458x(199911)37:11〈781::aid-mrc556〉3.0.co;2-h.
Paul, P., Hossain, M., & Kumar, G. S. (2011). Calorimetric and thermal analysis studies on the binding of phenothiazinium dye thionine with DNA polynucleotides. Jour nal of Chemical Thermodynamics, 43, 1036–1043. DOI:10.1016/j.jct.2011.02.009.
Phenix Research Products (2011). Overview of common fluorescent dyes used in nucleic acid quantitation. Retrieved August 14, 2012, from http://www.phenixresearch.com/Images/TN_FluorecentProbeQuantitation.pdf
Sečkářovál, J., Dommisse, R., Dostál J., Dommisse, R., & Esmans, E. L. (2002). Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy. Magnetic Resonance in Chemistry, 40, 147–152. DOI: 10.1002/mrc.979.
Sen, A., Ray, A., & Maiti, M. (1996). Thermodynamics of the interactions of sanguinarine with DNA: influence of ionic strength and base composition. Biophysical Chemistry, 59, 155–170. DOI: 10.1016/0301-4622(95)00137-9.
Slavik, J., Dolejs, L., Hanus, V., & Cross, A. D. (1968). Alkaloids of Papaveraceae.40. chelirubine chelilutine sanguirubine and sanguilutine. Mass and nuclear magnetic resonance spectra of benzophenanthridine alkaloids. Collection of Czechoslovak Chemical Communications, 33, 1619–1647.
Suchomelová, J., Bochořáková, H., Paulová, H., Musil, P., & Táborská, E. (2007). HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae. Journal of Pharmaceutical and Biomedical Analysis, 44, 283–287. DOI: 10.1016/j.jpba.2007.02.005.
Urbanová, J., Lubal, P., Slaninová, I., Táborská, E., & Táborský, P. (2009). Fluorescence properties of selected benzo[c]phenantridine alkaloids and studies of their interaction with CT DNA. Analytical and Bioanalytical Chemistry, 394, 997–1002. DOI: 10.1007/s00216-009-2601-7.
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Rybáková, S., Rájecký, M., Urbanová, J. et al. Interaction of oligonucleotides with benzo[c]phenanthridine alkaloid sanguilutine. Chem. Pap. 67, 568–572 (2013). https://doi.org/10.2478/s11696-013-0340-x
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DOI: https://doi.org/10.2478/s11696-013-0340-x