Skip to main content
Log in

Interaction of 1,4-Dihydroxy–9,10-Anthraquinone with Calf Thymus DNA: A Comparison with Anthracycline Anticancer Drugs

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

The anthracycline drugs adriamycin and daunorubicin, efficient in the treatment of various human cancers, form strong intercalation complexes with DNA. The therapeutic efficacy and toxicity of such anticancer drugs are governed by biochemical reactions of the core dihydroxy-9,10-anthraquinone unit. The high cost and toxic side effects of anthracycline drugs limit their use in cancer therapy. For a few decades, efforts have been made to find cheap, less toxic yet efficient analogues of anthracyclines. This work on 1,4-dihydroxy-9,10-anthraquinone (QH2), a simple analogue of the anthracyclines, was carried out to compare its biochemical properties with anthracyclines. UV-Vis and fluorescence spectroscopic methods were used to analyze interaction of the compound with calf thymus DNA. The data were used to evaluate the binding constant and site size.

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.

Similar content being viewed by others

Abbreviations

QH2 :

1,4-dihydroxy-9,10-anthraquinone

ctDNA:

calf thymus DNA

References

  1. Hardman, J.G., Gilman, A.G., Limbird, L.E.: Goodman and Gilman’s The Pharmacological Basis of Therapeutics, 9th edn. McGraw-Hill, New York (1996)

    Google Scholar 

  2. Reszka, K., Kolodziejczyk, P., Hartley, J.A., Wilson, W.D., Lown, J.W.: Anthracycline and Anthracenedionebased Anticancer Agents. Elsevier, Amsterdam (1998)

    Google Scholar 

  3. Eriksson, M., Nordbn, B., Eriksson, S.: Anthracycline-DNA interactions studied with linear dichroism and fluorescence spectroscopy. Biochemistry 27, 8144–8151 (1988)

    Article  CAS  Google Scholar 

  4. Li, N., Ma, Y., Yang, C., Guo, L., Yang, L.: Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods. Biophys. Chem. 116, 199–205 (2005)

    Article  CAS  Google Scholar 

  5. Banerjee, T., Mukhopadhyay, R.: Structural effects of nogalamycin, an antibiotic antitumor agent, on DNA. Biochem. Biophys. Res. Commun. 374, 264–268 (2008)

    Article  CAS  Google Scholar 

  6. Dutta, P.K., Hutt, J.A.: Resonance Raman spectroscopic studies of adriamycin and copper(II)-adriamycin and copper(II)-adriamycin-DNA complexes. Biochemistry 25, 691–695 (1986)

    Article  CAS  Google Scholar 

  7. Beraldo, H., Gurnier-Suillerot, A., Tosi, L., Lavelle, F.: Iron(III)-adriamycin and iron(III)-daunorubicin complexes: physicochemical characteristics, interaction with DNA, and antitumor activity. Biochemistry 24, 284–289 (1985)

    Article  CAS  Google Scholar 

  8. Kellogg, G.E., Scarsdale, J.N., Fornari, F.A.: Identification and hydropathic characterization of structural features affecting sequence specificity for doxorubicin intercalation into DNA double-stranded polynucleotides. Nucleic Acids Res. 26, 4721–4732 (1998)

    Article  CAS  Google Scholar 

  9. Zhang, H.M., Li, N.Q.: Electrochemical studies of the interaction of adriamycin to DNA. J. Pharm. Biomed. Anal. 22, 67–73 (2000)

    Article  CAS  Google Scholar 

  10. Lown, J.W., Sim, S.-K., Majumdar, K.C.: Strand scission of DNA by bound adriamycin and daunorubicin in the presence of reducing agents. Biochem. Biophys. Res. Commun. 76, 705–710 (1977)

    Article  CAS  Google Scholar 

  11. Ferrans, V.J.: Overview of cardiac pathology in relation to anthracycline cardiotoxicity. Cancer Treat. Rep. 62, 955–961 (1978)

    CAS  Google Scholar 

  12. Abraham, R., Basser, R.L., Green, M.D.: A risk-benefit assessment of anthracycline antibiotics in antineoplastic therapy. Drug Safety 15, 406–429 (1996)

    Article  CAS  Google Scholar 

  13. Stathopoulos, G.P., Malamos, N.A., Dontas, I., Deliconstantinos, G., Perrea-Kotsarelis, D., Karayannacos, P.E.: Inhibition of adriamycin cardiotoxicity by 5-fluorouracil: A potential free oxygen radical scavenger. Anticancer Res. 18, 4387–4392 (1998)

    CAS  Google Scholar 

  14. Guin, P.S., Das, S., Mandal, P.C.: Electrochemical reduction of sodium 1,4-dihydroxy-9,10-anthraquinone-2-sulphonate in aqueous and aqueous dimethyl formamide mixed solvent: A cyclic voltametric study. Int. J. Electrochem. Sci. 3, 1016–1028 (2008)

    CAS  Google Scholar 

  15. Guin, P.S., Das, S., Mandal, P.C.: Sodium 1,4-dihydroxy–9,10-anthraquinone–2-sulphonate interacts with calf thymus DNA in a way that mimics anthracycline antibiotics: An electrochemical and spectroscopic study. J. Phys. Org. Chem. 23, 477–482 (2010)

    Article  CAS  Google Scholar 

  16. Priebe, W.: Targeting DNA with anthracyclines: the importance of the sugar moiety. Molecules 5, 299–301 (2000)

    Article  CAS  Google Scholar 

  17. Guin, P.S., Das, S., Mandal, P.C.: Studies on the formation of a complex of Cu(II) with sodium 1,4-dihydroxy–9,10-anthraquinone–2-sulphonate—An analogue of the core unit of anthracycline anticancer drugs and its interaction with calf thymus DNA. J. Inorg. Biochem. 103, 1702–1710 (2009)

    Article  CAS  Google Scholar 

  18. Guin, P.S., Das, S., Mandal, P.C.: Formation and characterization of Ni(II) complex of sodium 1,4-dihydroxy–9,10-anthraquinone–2-sulphonate, an analogue of the core unit of anthracycline antibiotics, by different spectroscopic techniques. Int. J. Pure Appl. Chem. 3, 283–290 (2008)

    Google Scholar 

  19. Toshima, K., Ouchi, H., Okazaki, Y., Kano, T., Moriguchi, M., Matsumura, S., Asai, A.: Artificial anthraquinone-carbohydrate hybrids: Design, synthesis, DNA binding and cytotoxicity. Angew. Chem. 36, 2748–2750 (1997)

    Article  CAS  Google Scholar 

  20. Warburg, O., Christian, W.: Isolation and crystallization of enolase. Biochem. Z. 310, 384–421 (1942)

    CAS  Google Scholar 

  21. Chakraborti, S., Bhattacharyya, B., Dasgupta, D.: Interaction of mithramycin and chromomycin A3 with d(TAGCTAGCTA)2: Role of sugars in antibiotic-DNA recognition. J. Phys. Chem. B 106, 6947–6953 (2002)

    Article  Google Scholar 

  22. Mir, M.A., Majee, S., Das, S., Dasgupta, D.: Association of chromatin with anticancer antibiotics, methramycin and chromomycin A 3. Bioorg. Med. Chem. Lett. 11, 2791–2801 (2003)

    Article  CAS  Google Scholar 

  23. Cantor, C., Schimmel, P.R.: Biophysical Chemistry, vol. 2. Freeman, San Francisco (1980)

    Google Scholar 

  24. Takenaka, I., Ihara, T., Takagi, M.: Bis-9-acridinyl derivative containing a viologen linker chain: electrochemically active intercalator for reversible labeling of DNA. J. Chem. Soc. Chem. Commun. 1485–1487 (1990)

  25. Long, E.C., Barton, J.K.: On demonstrating DNA intercalation. Acc. Chem. Res. 23, 271–273 (1990)

    Article  CAS  Google Scholar 

  26. Pyle, A.M., Rehmann, J.P., Meshoyrer, R., Kumar, C.V., Turro, N.J., Barton, J.K.: Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA. J. Am. Chem. Soc. 111, 3051–3058 (1989)

    Article  CAS  Google Scholar 

  27. Lakowicz, J.R.: Principles of Fluorescence Spectroscopy, pp. 239–240. Kluwer Academic, New York (1999)

    Google Scholar 

  28. Zhong, W., Yu, J.S., Huang, W.L., Ni, K.Y., Liang, Y.Q.: Spectroscopic studies of interaction of chlorobenzylidine with DNA. Biopolymers 62, 315–323 (2001)

    Article  CAS  Google Scholar 

  29. Frezard, F., Garnier-Suillerot, A.: Comparison of anthracycline derivatives to purified DNA and to cell nuclei. Biochim. Biophys. Acta 1036, 121–127 (1990)

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Parikshit Chandra Mandal.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Guin, P.S., Das, S. & Mandal, P.C. Interaction of 1,4-Dihydroxy–9,10-Anthraquinone with Calf Thymus DNA: A Comparison with Anthracycline Anticancer Drugs. J Solution Chem 40, 492–501 (2011). https://doi.org/10.1007/s10953-011-9654-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-011-9654-x

Keywords

Navigation