Skip to main content
SpringerLink
Log in

Cholesterol and its fatty acid esters in native DNA preparations: lipid analysis, computer simulation of their interaction with DNA and cholesterol binding to immobilized oligodeoxyribonucleotides

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Supramolecular DNA complexes were isolated from rat normal cells and murine tumors. The content of DNA-bound lipids (cholesterol and its esters) was determined. The content of cholesterol esters is higher than that of free cholesterol; the lipid content in tumor cells is higher than in normal cells. Using the molecular mechanics approach, it is demonstrated for the first time that cholesterol and its esters with stearic, oleic, linoleic, and linolenic acids bind to the DNA minor groove more strongly than with the major groove. The calculated DNA binding energies of cholesterol and its esters depend on both the number of double bonds in the fatty acid residue and on the DNA nucleotide composition. The formation of stable complexes between cholesterol molecules and d(AT)-rich oligonucleotides was demonstrated using biological microchip containing immobilized octadeoxyribonucleotides.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G. Bischoff and R. I. Zhdanov, in Analysis of Biomedical Signals and Images, Proc. of 16th EURASIP Conf., Eds J. Jan, J. Kozumplik, and I. Provaznik, Vutium Press, Brno, 2002, p. 409.

    Google Scholar 

  2. R. I. Zhdanov and A. A. Kubatiev, Patogenez (Pathogenesis) 2003, 1, 7 (in Russian).

    Google Scholar 

  3. G. Bischoff, R. Zhdanov, and S. Hoffmann, Frount. in Med. Chem., 2004, 1, 649.

    Google Scholar 

  4. Lipid MAPS (Lipid Metabolites and Pathways Strategy), Consortium, Washington (DC), 2004, www.lipidmaps.com

  5. L. Cocco, A. M. Martelli, R. S. Gilmour, S. G. Rhee, and F. A. Manzoli, Biochim. Biophys. Acta, 2001, 1530, 1.

    CAS  Google Scholar 

  6. J. P. Incardona and S. Eaton, Current Opinion Cell. Biol., 2000, 12, 193.

    CAS  Google Scholar 

  7. Z. Khan, M. Aziatti, and A. O. Hawtrey, Med. Sci. Res., 1987, 15, 1189.

    CAS  Google Scholar 

  8. V. A. Struchkov, N. B. Strazhevskaya, and R. I. Zhdanov, Bioelectrochem., 2002, 58, 23.

    Article  CAS  Google Scholar 

  9. R. I. Zhdanov, V. A. Struchkov, O. S. Dyabina, and N. B. Strazhevskaya, Cytobios, 2001, 106, 56.

    Google Scholar 

  10. R. I. Zhdanov, N. B. Strazhevskaya, A. R. Jdanov, and G. Bischoff, J. Biomol. Struct. Dynamics, 2002, 20, 232.

    Google Scholar 

  11. R. I. Zhdanov, A. A. Kubatiev, A. Arslan, G. Bischoff, and W. Lorenz, in Proc. of Int. Conf. “GeoN” the 200th Anniversary of Kazan’ State University, Kazan’, August 25–September 3, 2003, 411.

  12. V. A. Struchkov and N. B. Strazhevskaya, Biokhimiya, 1993, 58, 1154 [Biochemistry (Moscow), 1993, 58, 815 (Engl. Transl.)].

    CAS  Google Scholar 

  13. V. A. Struchkov, and N. B. Strazhevskaya, Biokhimiya, 2000, 65, 620 [Biochemistry (Moscow), 2000, 65, 525 (Engl. Transl.)].

    Google Scholar 

  14. S. D. Belyaev, N. B. Strazhevskaya, I. K. Kolomiitseva, V. A. Struchkov, and A. M. Kuzin, Dokl. Akad. Nauk SSSR, 1974, 214, 1189 [Dokl. Chem., 1974 (Engl. Transl.)].

    CAS  Google Scholar 

  15. G. P. Georgiev and V. A. Struchkov, Biofizika [Biophysics], 1961, 5, 745 (in Russian).

    Google Scholar 

  16. Zs. Balint, Basic Appl. Histochem., 1987, 31, 365.

    CAS  Google Scholar 

  17. H. Bene, D. Lasky, and J. M. Ntambi, Biochim. Biophys. Res. Commun., 2001, 284, 1194.

    Article  CAS  Google Scholar 

  18. R. I. Zhdanov, E. P. D’yachkov, V. A. Struchkov, N. B. Strazhevskaya, and P. N. D’yachkov, Izv. Akad. Nauk. Ser. Khim., 2003, 1794 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1893].

    Google Scholar 

  19. R. I. Zhdanov, E. P. D’yachkov, N. B. Strazhevskaya, V. A. Struchkov, and P. N. D’yachkov, Dokl. Akad. Nauk, 2003, 390, 548 [Dokl. Chem., 2003 (Engl. Transl.)].

    Google Scholar 

  20. A. S. Krylov, O. A. Zasedateleva, D. V. Prokopenko, J. Rouviere-Yaniv, and A. D. Mirzabekov, Nucleic Acids Res., 2001, 29, 2654.

    Article  CAS  Google Scholar 

  21. G. Yershov, V. Barsky, A. Belgovsky, Eu. Kirilov, E. Kreindlin, I. Ivanov, S. Parinov, D. Guschin, A. Drobyshev, S. Dubiley, and A. Mirzabekov, Proc. Nat. Acad. Sci. USA, 1996, 93, 4913.

    Article  CAS  Google Scholar 

  22. O. A. Zasedateleva, A. S. Krylov, D. V. Prokopenko, M. A. Skabkin, L. P. Ovchinnikov, A. Kolchinsky, and A. D. Mirzabekov, J. Mol. Biol., 2002, 324, 73.

    Article  CAS  Google Scholar 

  23. V. R. Chechetkin, D. V. Prokopenko, O. A. Zasedateleva, G. I. Gitelson, E. S. Lomakin, M. A. Livshits, L. Malinina, A. Yu. Turygin, A. S. Krylov, and A. D. Mirzabekov, J. Biomol. Struct. Dynamics., 2003, 21, 341.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of General Pathology and Pathophysiology, Russian Academy of Medical Sciences, 8 ul. Baltiiskaya, 125315, Moscow, Russian Federation

    R. I. Zhdanov, E. P. D’yachkov, N. B. Strazhevskaya, A. S. Shmyrina, A. S. Krylov & A. A. Kubatiev

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninskii prosp., Moscow, Russian Federation

    E. P. D’yachkov & P. N. D’yachkov

  3. Institute of Food and Environmental Chemistry, Martin—Luther University Halle-Wittenberg, Kurt-Mothes str. 2, 06120, Halle (Saale), Germany

    W. Lorenz

Authors
  1. R. I. Zhdanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. P. D’yachkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. B. Strazhevskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Shmyrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. S. Krylov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. P. N. D’yachkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. W. Lorenz
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. A. A. Kubatiev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2138–2144, September, 2005.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhdanov, R.I., D’yachkov, E.P., Strazhevskaya, N.B. et al. Cholesterol and its fatty acid esters in native DNA preparations: lipid analysis, computer simulation of their interaction with DNA and cholesterol binding to immobilized oligodeoxyribonucleotides. Russ Chem Bull 54, 2204–2210 (2005). https://doi.org/10.1007/s11172-006-0097-2

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-006-0097-2

Key words

Search

Navigation