Skip to main content
Log in

Interaction of oligonucleotides with benzo[c]phenanthridine alkaloid sanguilutine

  • Short Communication
  • Published:
Chemical Papers Aims and scope Submit manuscript

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).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

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 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Petr Táborský.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-013-0340-x

Keywords

Navigation