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Interaction of oligonucleotides with benzo[c]phenanthridine alkaloid sanguilutine

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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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

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Correspondence to Petr Táborský.

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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

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