Journal of Surfactants and Detergents

, Volume 17, Issue 2, pp 261–268 | Cite as

Synthesis and Characterization of Novel Cationic Lipids Derived from Thio Galactose

Original Article

Abstract

Two double chain cationic lipids QAS Cn-2-S (n = 12, 14) derived from thio galactose and carbamate-linkage tertiary amine were synthesized and their structures were confirmed by MS, TOF-MS, 1H NMR and 13C NMR. The QAS C12-2-S revealed superior surface activity compared with QAS C14-2-S with lower CMC and γCMC. Though Lipo C12-2-S displayed large average particle-size with high polydispersity, positive charged Lipo Cn-2-S can be combined with the negative charged DNA, also negatively stained TEM images confirmed the formation of vesicles. All the above prove that the Lipo Cn-2-S is helpful for gene transfection.

Keywords

Synthesis Thio galactose Cationic lipids Vesicle 

References

  1. 1.
    Hirko A, Tang FX, Hughes JA (2003) Cationic lipid vectors for plasmid DNA delivery. Curr Med Chem 10:1185–1193CrossRefGoogle Scholar
  2. 2.
    Ewert K, Slack NL, Ahmad A, Evans HM, Lin AJ, Samuel CE, Safinya CR (2004) Cationic lipid–DNA complexes for gene therapy: understanding the relationship between complex structure and gene delivery pathways at the molecular level. Curr Med Chem 11:133–149CrossRefGoogle Scholar
  3. 3.
    Mahato RI, Kim SW (2002) Pharmaceutical perspectives of nucleic acid based therapeutics. Taylor and Francis, LondonCrossRefGoogle Scholar
  4. 4.
    Wilard HF (2000) Genomics and gene therapy: artificial chromosomes coming to life. Science 290:1308–1309CrossRefGoogle Scholar
  5. 5.
    Ashwell G, Harford J (1982) Carbohydrate-specific receptors of the liver. Annu Rev Biochem 51:531–554CrossRefGoogle Scholar
  6. 6.
    Hashida M, Nishikawa M, Yamashita F, Takakura Y (2001) Cell-specific delivery of genes with glycosylated carriers. Adv Drug Deliv Rev 52:187–196CrossRefGoogle Scholar
  7. 7.
    Yuzawa H, Fujioka H, Mizoe A, Azuma T, Furui J, Nishikawa M, Hashida M, Kanematsu T (2005) Inhibitory effects of safe and novel SOD derivatives, galactosylated-SOD, on hepatic warm ischemia/reperfusion injury in pigs. Hepatogastroenterology 52:839–843Google Scholar
  8. 8.
    Kawakami S, Yamashita F, Nishikawa M, Takakura Y, Hashida M (1998) Asialoglycoprotein receptor-mediated gene transfer using novel galactosylated cationic liposomes. Biochem Biophys Res Commun 252:78–83CrossRefGoogle Scholar
  9. 9.
    Shigeta K, Kawakami S, Higuchi Y, Okuda T, Yagi H, Yamashita F, Hashida M (2007) Novel histidine-conjugated galactosylated cationic liposomes for efficient hepatocyte-selective gene transfer in human hepatoma HepG2 cells. J Control Release 118:262–270CrossRefGoogle Scholar
  10. 10.
    Sun X, Hai L, Wu Y, Hu HY, Zhang ZR (2005) Targeted gene delivery to hepatoma cells using galactosylated liposome–polycation–DNA complexes (LPD). Drug Target 13:121–128CrossRefGoogle Scholar
  11. 11.
    Yang QR, Qiao WH, Zhang SM, Qu JP, Liu DL (2010) Synthesis and characterization of a new cationic galactolipid with carbamate for gene delivery. Tens Surf Det 5:294–299Google Scholar
  12. 12.
    Zhang SM, Qiao WH, Chen YX, Liu DL (2009) Synthesis of cationic surfactant intermediates 3-(dimethylamino) propane-1,2-di-alkylcarbamate. Tens Surf Det 46:228–231Google Scholar
  13. 13.
    Bangham AD, Standish MM, Watkins JC (1965) Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol 13:238–252CrossRefGoogle Scholar
  14. 14.
    Feitosa E, Brown W (1997) Fragment and vesicle structures in sonicated dispersions of dioctadecyldimethylammonium bromide. Langmuir 13:4810–4816CrossRefGoogle Scholar
  15. 15.
    Rosen MJ (1989) Surfactants and interfacial phenomena, 2nd edn. Wiley, New YorkGoogle Scholar
  16. 16.
    Xiao J, Zhao Z (2003) Principles of surfactant application, 1st edn. Chemical Industry Press, BeijingGoogle Scholar
  17. 17.
    Tanford C (1973) The hydrophobic effect: formation of micelles and biological membranes. Wiley-Interscience, New YorkGoogle Scholar
  18. 18.
    Israelachvili JN (1985) Intermolecular and surface forces: with applications to colloidal and biological systems. Academic Press, LondonGoogle Scholar

Copyright information

© AOCS 2013

Authors and Affiliations

  1. 1.State Key Laboratory of Fine Chemicals, School of Chemical EngineeringDalian University of TechnologyDalianPeople’s Republic of China

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