Fluorescence properties of selected benzo[c]phenantridine alkaloids and studies of their interaction with CT DNA

  • Jana Urbanová
  • Přemysl Lubal
  • Iva Slaninová
  • Eva Táborská
  • Petr Táborský
Original Paper

Abstract

The spectral, especially fluorescence properties, of seven selected quaternary benzo[c]phenantridine alkaloids (sanguinarine, chelerythrine, chelirubine, sanguirubine, chelilutine, sanguilutine, and macarpine) were studied in presence and in absence of double-stranded DNA. This study has proved dramatic differences in fluorescence emission of all studied alkaloids in presence of calf thymus DNA in comparison to fluorescence of free alkaloids. The most remarkable are changes in emission spectra of macarpine, chelirubine, and sanguirubine. Association constants (logK) for interaction of all studied alkaloids with CT DNA were calculated.

Keywords

Benzo[c]phenantridine alkaloids Sanguinarine Chelirubine Sanguirubine Chelilutine Macarpine Association constants 

Notes

Acknowledgments

This work was supported by projects CSF 525/08/0819 and LC06035 BIO-ANAL-MED.

References

  1. 1.
    Kovar J, Simek K, Kozouskova E, Klukanova H, Slavik J (1985) Collect Czech Chem Commun 50:1312–1328Google Scholar
  2. 2.
    Takao N, Kamigauchi M, Okada M (1983) Helv Chim Acta 66:473–483CrossRefGoogle Scholar
  3. 3.
    Ahmad N, Gupta S, Husain MM, Heiskanen KM, Mukhtar H (2000) Clin Cancer Res 6:1524–1528Google Scholar
  4. 4.
    Suchomelova J, Bochorakova H, Paulova H, Musil P, Taborska E (2007) J Pharm Biomed Anal 44:283–287CrossRefGoogle Scholar
  5. 5.
    Ishikawa T, Saito T, Ishii H (1995) Tetrahedron 51:8447–8458CrossRefGoogle Scholar
  6. 6.
    Hanaoka M, Won JC, Yoshida S, Fueki T, Mukai C (1989) Heterocycles 29:857–860CrossRefGoogle Scholar
  7. 7.
    Dostal J, Slavik J, Potacek M, Marek R, Humpa O, Sklenar V, Tousek J, de Hoffmann E, Rozenberg R (1998) Coll Czech Chem Commun 63:1045–1055CrossRefGoogle Scholar
  8. 8.
    Seckarova P, Marek R, Dostal J, Dommisse R, Esmans EL (2002) Magn Resonance Chem 40:147–152CrossRefGoogle Scholar
  9. 9.
    Slaninova I, Slanina J, Taborska E (2008) Chem Listy 102:427–433Google Scholar
  10. 10.
    Maiti M, Kumar GS (2007) Med Research Rev 27:649–695CrossRefGoogle Scholar
  11. 11.
    Zdarilova A, Malikova J, Dvorak Z, Ulrichova J, Simanek V (2006) Chem Listy 100:30–41Google Scholar
  12. 12.
    Kaminskyy VO, Lootsik MD, Stoika RS (2006) Central Eur J Biol 1:2–15CrossRefGoogle Scholar
  13. 13.
    Bai LP, Zhao ZZ, Cai ZW, Jiang ZH (2006) Bioorg Med Chem 14:5439–5445CrossRefGoogle Scholar
  14. 14.
    Sen A, Maiti M (1994) Biochem Pharmacology 48:2097–2102CrossRefGoogle Scholar
  15. 15.
    Sen A, Ray A, Maiti M (1996) Biophys Chem 59:155–170CrossRefGoogle Scholar
  16. 16.
    Debnath D, Kumar GS, Maiti M (1991) J Biomol Struct Dyn 9:61–79Google Scholar
  17. 17.
    Smekal E, Kubova N, Kleinwachter V (1984) Studia Biophys 101:125–132Google Scholar
  18. 18.
    Vlckova M, Kuban V, Vicar J, Simanek V (2005) Electrophoresis 26:1673–1679CrossRefGoogle Scholar
  19. 19.
    Slaninova I, Slanina J, Taborska E (2007) Cytometry Part A 71A:700–708CrossRefGoogle Scholar
  20. 20.
    Bai LP, Cai Z, Zhao ZZ, Nakatani K, Jiang ZH (2008) Anal Bioanal Chem 392:709–716CrossRefGoogle Scholar
  21. 21.
    Slaninova I, Taborska E, Bochorakova H, Slanina J (2001) Cell Biol Toxic 17:51–63CrossRefGoogle Scholar
  22. 22.
    Oconnor T, Mansy S, Bina M, McMillin DR, Bruck MA, Tobias RS (1982) Biophys Chem 15:53–64CrossRefGoogle Scholar
  23. 23.
    Eaton DF (1988) Pure Appl Chem 60:1107–1114CrossRefGoogle Scholar
  24. 24.
    Kellogg RE, Bennett RGJ (1964) Chem Phys 41:3042–&Google Scholar
  25. 25.
    Kyvala M, Lubal P, Lukes I (1998) Determination of Equilibrium Constants with the OPIUM Computer Program, IX Spanish–Italian and Mediterranean Congress on Thermodynamics of Metal Complexes SIMEC’98, Girona, Spain, June 2–5, 1998; http://www.natur.cuni.cz/∼kyvala/opium.html
  26. 26.
    Tousek J, Dostal J, Slaninova I, Taborska E (2005) A quantum chemical study vs. biological activity of seven quaternary benzophenanthridine alkaloids, 11th BDSHC (Czech Republic), Brno, PO 18Google Scholar
  27. 27.
    Khan N, Avino A, Tauler R, Gonzalez G, Eritja R, Gargallo R (2007) Biochimie 89:1562–1572CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Jana Urbanová
    • 1
  • Přemysl Lubal
    • 1
  • Iva Slaninová
    • 2
  • Eva Táborská
    • 3
  • Petr Táborský
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceMasaryk UniversityBrnoCzech Republic
  2. 2.Department of Biology, Faculty of MedicineMasaryk UniversityBrnoCzech Republic
  3. 3.Department of Chemistry and Biochemistry, Faculty of MedicineMasaryk UniversityBrnoCzech Republic

Personalised recommendations