Elsevier

Tetrahedron Letters

Volume 36, Issue 13, 27 March 1995, Pages 2207-2210
Tetrahedron Letters

A flexible approach to synthetic lipid ammonium salts for polynucleotide transfection

https://doi.org/10.1016/0040-4039(95)00276-IGet rights and content

Abstract

The synthesis of novel 2,3-acyloxy-1-propylammonium salts is described. The route incorporates the use of glycidol and N-methyl-2-aminoethanol to prepare cationic lipids with control of absolute stereochemistry and regioselective introduction of fatty acid side chains.

References (29)

  • X. Gao et al.

    Biochem. Biophys. Res. Commun.

    (1991)
  • H. Farhood et al.

    Biochim. Biophys. Acta

    (1992)
  • J.H. Felgner et al.

    J. Biol. Chem.

    (1994)
  • R. Leventis et al.

    Biochim. Biophys. Acta

    (1990)
  • A.F. Rosenthal et al.

    J. Biol. Chem.

    (1960)
  • S.K. Chaudhary et al.

    Tetrahedron Lett.

    (1979)
  • S.K. Chaudhary et al.

    Tetrahedron Lett.

    (1979)
  • M. Chini et al.

    Tetrahedron Lett.

    (1990)
  • D.R. Kodali et al.

    Chem. Phys. Lipids

    (1990)
  • A.A. Duralski et al.

    Tetrahedron Lett.

    (1989)
  • A.P.J. Mank et al.

    Chem. Phys. Lipids

    (1976)
  • J.-P. Behr

    Bioconjugate Chem.

    (1994)
  • K.L. Brigham et al.

    J. Liposome Res.

    (1993)
  • X. Gao et al.

    J. Liposome Res.

    (1993)
  • Cited by (36)

    • Carbamate-linked cationic lipids for gene delivery

      2008, Bioorganic and Medicinal Chemistry
    • Whole animal in vivo imaging after transient, nonviral gene delivery to the rat central nervous system

      2008, Molecular Therapy
      Citation Excerpt :

      Lipids and formulation of lipid:nucleic acid complexes (lipoplexes). After in vitro comparisons with several commercially available lipids, the cationic lipid that performed best was MLRI.23,24 This lipid was then used for further transfections in vitro and in vivo.

    • Synthesis of carbamate-linked lipids for gene delivery

      2005, Bioorganic and Medicinal Chemistry Letters
    • Nonviral gene delivery to the lateral ventricles in rat brain: Initial evidence for widespread distribution and expression in the central nervous system

      2001, Molecular Therapy
      Citation Excerpt :

      We refer to our optimized, controlled incubation of DNA and cationic lipid which leads to the self-assembly of these nucleic acid/cationic lipid complexes as “formulation.” In vitro transfections were optimized using novel cationic lipids developed by Nantz et al. (8–10). DNA dose and cationic lipid to DNA ratio was systematically varied in a series of transfections to arrive at our optimized formulation.

    View all citing articles on Scopus
    View full text