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).
[1] 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. http://dx.doi.org/10.1016/j.molstruc.2008.01.01610.1016/j.molstruc.2008.01.016Search in Google Scholar
[2] 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. http://dx.doi.org/10.1016/j.bmc.2006.05.01210.1016/j.bmc.2006.05.012Search in Google Scholar
[3] 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. http://dx.doi.org/10.1007/s00216-008-2302-710.1007/s00216-008-2302-7Search in Google Scholar
[4] 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. http://dx.doi.org/10.1002/cbic.20080025610.1002/cbic.200800256Search in Google Scholar
[5] 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. http://dx.doi.org/10.1002/med.2020210.1002/med.20202Search in Google Scholar
[6] 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. http://dx.doi.org/10.1016/j.bbagen.2011.01.01110.1016/j.bbagen.2011.01.011Search in Google Scholar
[7] 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. http://dx.doi.org/10.1016/S0031-9422(97)00665-110.1016/S0031-9422(97)00665-1Search in Google Scholar
[8] 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. http://dx.doi.org/10.3987/REV-06-61010.3987/REV-06-610Search in Google Scholar
[9] 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. http://dx.doi.org/10.1016/S0959-8049(11)72519-910.1016/S0959-8049(11)72519-9Search in Google Scholar
[10] 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. http://dx.doi.org/10.1016/j.jct.2008.12.00810.1016/j.jct.2008.12.008Search in Google Scholar
[11] 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. http://dx.doi.org/10.1016/j.jct.2010.05.00510.1016/j.jct.2010.05.005Search in Google Scholar
[12] 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. http://dx.doi.org/10.1016/j.jct.2011.09.02610.1016/j.jct.2011.09.026Search in Google Scholar
[13] 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. http://dx.doi.org/10.1007/s00216-009-2903-910.1007/s00216-009-2903-9Search in Google Scholar
[14] 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. http://dx.doi.org/10.1039/b925828k10.1039/b925828kSearch in Google Scholar
[15] 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. 10.1089/nat.2012.0342Search in Google Scholar
[16] 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. http://dx.doi.org/10.1016/j.jchromb.2011.03.02310.1016/j.jchromb.2011.03.023Search in Google Scholar
[17] 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. http://dx.doi.org/10.1135/cccc1986262610.1135/cccc19862626Search in Google Scholar
[18] 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. Search in Google Scholar
[19] 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. http://dx.doi.org/10.1002/(SICI)1097-458X(199911)37:11<781::AID-MRC556>3.0.CO;2-H10.1002/(SICI)1097-458X(199911)37:11<781::AID-MRC556>3.0.CO;2-HSearch in Google Scholar
[20] 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. http://dx.doi.org/10.1016/j.jct.2011.02.00910.1016/j.jct.2011.02.009Search in Google Scholar
[21] 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 Search in Google Scholar
[22] 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. http://dx.doi.org/10.1002/mrc.97910.1002/mrc.979Search in Google Scholar
[23] 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. http://dx.doi.org/10.1016/0301-4622(95)00137-910.1016/0301-4622(95)00137-9Search in Google Scholar
[24] 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. http://dx.doi.org/10.1135/cccc1968161910.1135/cccc19681619Search in Google Scholar
[25] 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. http://dx.doi.org/10.1016/j.jpba.2007.02.00510.1016/j.jpba.2007.02.005Search in Google Scholar PubMed
[26] 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. http://dx.doi.org/10.1007/s00216-009-2601-710.1007/s00216-009-2601-7Search in Google Scholar PubMed
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