Advertisement

Russian Chemical Bulletin

, Volume 61, Issue 7, pp 1497–1501 | Cite as

Synthesis of mannose-containing neoglycolipids as a component of targeted delivery system for transfer of nucleic acids into antigen-presenting cells

  • E. V. Shmendel’
  • A. A. Timakova
  • M. A. Maslov
  • N. G. Morozova
  • V. V. Chupin
Brief Communications

Abstract

Two approaches to the preparation of mannose-containing neoglycolipid, designed for development of nonviral targeted delivery system for transfer of nucleic acids into antigen-presenting cells, were described. They differed from each other in the binding of the targeting ligand and the lipid anchor, which was effected either through the formation of an amide bond or via the chemoselective binding agent 3,4-diethoxycyclobut-3-ene-1,2-dione.

Key words

neoglycolipid mannose targeting ligand 3,4-diethoxycyclobut-3-ene-1,2-dione antigen-presenting cell 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    S. C. Oliveira, G. M. S. Rosinha, C. F. A. de-Brito, C. T. Fonseca, R. R. Afonso, M. C. M. S. Costa, A. M. Goes, E. L. Rech, V. Azevedo, Braz. J. Med. Biol. Res., 1999, 32, 207.Google Scholar
  2. 2.
    G. Chikh, M.-P. Schutze-Redelmeier, Biosci. Rep., 2002, 22, 339.CrossRefGoogle Scholar
  3. 3.
    S. Toda, N. Ishii, E. Okada, K. I. Kusakabe, H. Arai, K. Hamajima, I. Gorai, K. Nishioka, K. Okuda, Immunology, 1997, 92, 111.CrossRefGoogle Scholar
  4. 4.
    S. P. Vyas, Y. K. Katare, V. Mishra, V. Sihorkar, Int. J. Pharm., 2000, 210, 1.CrossRefGoogle Scholar
  5. 5.
    F. Chellata, Y. Merhib, A. Moreauc, L. Yahiaa, Biomaterials, 2005, 26, 7260.CrossRefGoogle Scholar
  6. 6.
    D. Boczkowski, S. K. Nair, D. Snyder, E. Gilboa, J. Exp. Med., 1996, 184, 465.CrossRefGoogle Scholar
  7. 7.
    M. R. Clark, D. Massenburg, K. Siemasko, P. Hou, Curr. Opin. Immunol., 2004, 16, 382.CrossRefGoogle Scholar
  8. 8.
    B. G. Davis, M. A. Robinson, Curr. Opin. Drug Discovery Dev., 2002, 5, 279.Google Scholar
  9. 9.
    S. Espuelas, C. Trumann, B. Heurtault, F. Schuber, B. Frisch, Bioconjugate Chem., 2008, 19, 2385.CrossRefGoogle Scholar
  10. 10.
    Y. Hattori, S. Kawakami, K. Nakamura, F. Yamashita, M. Hashida, J. Pharmacol. Exp. Ther., 2006, 318, 828.CrossRefGoogle Scholar
  11. 11.
    H.-K. Kim, H. Wei, A. Kulkarni, R. M. Pogranichniy, D. H. Thompson, Biomacromolecules, 2012, 13, 636.CrossRefGoogle Scholar
  12. 12.
    A. Bergh, B.-G. Magnusson, J. Ohlsson, U. Wellmar, U. J. Nilsson, Glycoconjugate J., 2001, 18, 615.CrossRefGoogle Scholar
  13. 13.
    E. V. Shmendel’, M. A. Maslov, N. G. Morozova, G. A. Serebrennikova, Russ. Chem. Bull. (Int. Ed.), 2010, 56, 2225 [Izv. Akad. Nauk, Ser. Khim., 2010, 2225].Google Scholar
  14. 14.
    G. Lemanski, T. Ziegler, Tetrahedron, 2000, 56, 563.CrossRefGoogle Scholar
  15. 15.
    C. A. Podlasek, J. Wu, W. A. Stripe, P. B. Bondo, A. S. Serianni, J. Am. Chem. Soc., 1995, 117, 8635.CrossRefGoogle Scholar
  16. 16.
    E. Shtal’, Khromatografiya v tonkikh sloyakh [Thin Layer Chromatography], Moscow, Mir, 1965, 477 pp. (in Russian).Google Scholar
  17. 17.
    D. Kritchevsky, M. R. Kirk, Arch. Biochem. Biophys., 1952, 35, 346.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • E. V. Shmendel’
    • 1
  • A. A. Timakova
    • 1
  • M. A. Maslov
    • 1
  • N. G. Morozova
    • 1
  • V. V. Chupin
    • 1
  1. 1.M. V. Lomonosov Moscow State University of Fine Chemical TechnologyMoscowRussian Federation

Personalised recommendations