Skip to main content
Log in

Synthesis of polycationic lipids based on cholesterol and spermine

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The synthesis of cholesterol-based cationic lipids in which the hydrophobic steroidal fragment is linked to a spermine residue as the hydrophilic domain by ester or carbamate linkage is described.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. D. Patil, D. G. Rhodes, D. J. Burgess, AAPS J., 2005, 7, E61.

    Article  CAS  Google Scholar 

  2. Non-viral Vectors for Gene Therapy, Part 1, Eds L. Huang, M.-C. Hung, E. Wagner, Elsevier, Amsterdam, 2005.

    Google Scholar 

  3. B. Martin, M. Sainlos, A. Aissaoui, N. Oudrhiri, M. Hauchecorne, J.-P. Vigneron, J.-M. Lehn, P. Lehn, Curr. Pharm. Design, 2005, 11, 375.

    Article  CAS  Google Scholar 

  4. M. A. Mintzer, E. E. Simanek, Chem. Rev., 2009, 109, 259.

    Article  CAS  Google Scholar 

  5. K. Kostarelos, A. D. Miller, Chem. Soc. Rev., 2005, 34, 970.

    Article  CAS  Google Scholar 

  6. M. A. Maslov, E. V. Sycheva, N. G. Morozova, G. A. Sere-brennikova, Izv. Akad. Nauk. Ser. Khim., 2000, 385 [Russ. Chem. Bull., Int. Ed., 2000, 49, 385].

    Google Scholar 

  7. A. D. Miller, Angew. Chem., Int. Ed., 1998, 37, 1768.

    Article  Google Scholar 

  8. H. Lv, S. Zhang, B. Wang, S. Cui, J. Yan, J. Control. Release, 2006, 114, 100.

    Article  CAS  Google Scholar 

  9. C. W. Tabor, H. Tabor, Annu. Rev. Biochem., 1984, 53, 749.

    Article  CAS  Google Scholar 

  10. R. W. Wilson, V. A. Bloomfield, Biochemistry, 1979, 18, 2192.

    Article  CAS  Google Scholar 

  11. V. A. Bloomfield, Curr. Opin. Struct. Biol., 1996, 6, 334.

    Article  CAS  Google Scholar 

  12. S. Venkiteswaran, T. Thomas, T. J. Thomas, in Polyamine Cell Signaling: Physiology, Pharmacology and Cancer Research, Eds J.-Y. Wang, R. A. Casero Jr., Humana Press Clifton, NJ, 2006, p. 91.

    Chapter  Google Scholar 

  13. A. A. Ouameur, H.-A. Tajmir-Riahi, J. Biol. Chem., 2004, 279, 42041.

    Article  CAS  Google Scholar 

  14. J. S. Remy, C. Sirlin, P. Vierling, J.-P. Behr, Bioconjugate Chem., 1994, 5, 647.

    Article  CAS  Google Scholar 

  15. A. J. Geall, R. J. Taylor, M. E. Earll, M. A. W. Eaton, I. S. Blagbrough, Bioconjugate Chem., 2000, 11, 314.

    Article  CAS  Google Scholar 

  16. G. Byk, C. Dubertret, V. Escriou, M. Frederic, G. Jaslin, R. Rangara, B. Pitard, J. Crouzet, P. Wils, B. Schwartz, D. Scherman, J. Med. Chem., 1998, 41, 224.

    Article  Google Scholar 

  17. A. J. Geall, M. A. W. Eaton, T. Baker, C. Catterall, I. S. Blagbrough, FEBS Lett., 1999, 459, 337.

    Article  CAS  Google Scholar 

  18. R. G. Cooper, C. J. Etheridge, L. Stewart, J. Marshall, S. Rudginsky, S. H. Cheng, A. D. Miller, Chem. Eur. J., 1998, 4, 137.

    Article  Google Scholar 

  19. L. Stewart, M. Manvell, E. Hillery, C. J. Etheridge, R. G. Cooper, H. Stark, M. van-Heel, M. Preuss, E. W. F. W. Alton, A. D. Miller, J. Chem. Soc., Perkin Trans. 2, 2001, 624.

  20. J. P. Behr, B. A. Demeneix, J. P. Loeffler, J. Perez-Mutul, Proc. Natl. Acad. Sci. USA, 1989, 86, 6982.

    Article  CAS  Google Scholar 

  21. E. R. Lee, J. Marshall, C. S. Siegel, C. Jiang, N. S. Yew, M. R. Nichols, J. B. Nietupski, R. J. Ziegler, M. Lane, K. X. Wang, R. K. Scheule, D. J. Harris, A. E. Smith, S. H. Cheng, Hum. Gene Ther., 1996, 7, 1701.

    Article  CAS  Google Scholar 

  22. P. Hawley-Nelson, V. Ciccarone, G. Gebeyehu, J. Jesse P. L. Felgner, Focus, 1993, 15, 73.

    Google Scholar 

  23. G. Ronsin, C. Perrin, P. Guédat, A. Kremer, P. Camilleri, A. J. Kirby, Chem. Commun., 2001, 2234.

  24. K. A. Miller, E. V. K. S. Kumar, S. J. Wood, J. R. Cromer, A. Datta, S. A. David, J. Med. Chem., 2005, 48, 2589.

    Article  CAS  Google Scholar 

  25. A. J. Geall, I. S. Blagbrough, Tetrahedron, 2000, 56, 2449.

    Article  CAS  Google Scholar 

  26. I. S. Blagbrough, A. J. Geall, A. P. Neal, Biochem. Soc. Trans., 2003, 31, 397.

    Article  CAS  Google Scholar 

  27. M. Oliver, M. R. Jorgensen, A. Miller, Tetrahedron Lett., 2004, 45, 3105.

    Article  CAS  Google Scholar 

  28. T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett., 1995, 36, 6373.

    Article  CAS  Google Scholar 

  29. T. Fukuyama, M. Cheung, C.-K. Jow, Y. Hidai, T. Kan, Tetrahedron Lett., 1997, 38, 5831.

    Article  CAS  Google Scholar 

  30. M. A. Ilies, W. A. Seitz, B. H. Johnson, E. L. Ezell, A. L. Miller, E. B. Thompson, A. T. Balaban, J. Med. Chem., 2006, 49, 3872.

    Article  CAS  Google Scholar 

  31. A. J. Kirby, P. Camilleri, J. B. F. N. Engberts, M. C. Feiters, R. J. M. Nolte, O. Soderman, M. Bergsma, P. C. Bell, M. L. Fielden, C. L. G. Rodriguez, P. Guedat, A. Kremer, C. McGregor, C. Perrin, G. Ronsin, M. C. P. van Eijk, Angew. Chem., Int. Ed., 2003, 42, 1448.

    Article  CAS  Google Scholar 

  32. M. C. Dowson, D. C. Elliot, W. H. Elliot, K. H. Jones, Date for Biochemical Research, Clarendon Press, Oxford, 1986.

    Google Scholar 

  33. D. Kritchevsky, M. R. Kirk, Arch. Biochem. Biophys., 1952, 35, 346.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. A. Maslov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 254–261, January, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Petukhov, I.A., Maslov, M.A., Morozova, N.G. et al. Synthesis of polycationic lipids based on cholesterol and spermine. Russ Chem Bull 59, 260–268 (2010). https://doi.org/10.1007/s11172-010-0071-x

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0071-x

Navigation