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Synthesis and Characterization of Novel Cationic Lipids Derived from Thio Galactose

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Journal of Surfactants and Detergents

Abstract

Two double chain cationic lipids QAS C n -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 C n -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 C n -2-S is helpful for gene transfection.

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References

  1. Hirko A, Tang FX, Hughes JA (2003) Cationic lipid vectors for plasmid DNA delivery. Curr Med Chem 10:1185–1193

    Article  CAS  Google Scholar 

  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 11:133–149

    Article  CAS  Google Scholar 

  3. Mahato RI, Kim SW (2002) Pharmaceutical perspectives of nucleic acid based therapeutics. Taylor and Francis, London

    Book  Google Scholar 

  4. Wilard HF (2000) Genomics and gene therapy: artificial chromosomes coming to life. Science 290:1308–1309

    Article  Google Scholar 

  5. Ashwell G, Harford J (1982) Carbohydrate-specific receptors of the liver. Annu Rev Biochem 51:531–554

    Article  CAS  Google Scholar 

  6. Hashida M, Nishikawa M, Yamashita F, Takakura Y (2001) Cell-specific delivery of genes with glycosylated carriers. Adv Drug Deliv Rev 52:187–196

    Article  CAS  Google Scholar 

  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 52:839–843

    CAS  Google Scholar 

  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 252:78–83

    Article  CAS  Google Scholar 

  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 118:262–270

    Article  CAS  Google Scholar 

  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 13:121–128

    Article  CAS  Google Scholar 

  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 5:294–299

    Google Scholar 

  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 46:228–231

    CAS  Google Scholar 

  13. Bangham AD, Standish MM, Watkins JC (1965) Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol 13:238–252

    Article  CAS  Google Scholar 

  14. Feitosa E, Brown W (1997) Fragment and vesicle structures in sonicated dispersions of dioctadecyldimethylammonium bromide. Langmuir 13:4810–4816

    Article  CAS  Google Scholar 

  15. Rosen MJ (1989) Surfactants and interfacial phenomena, 2nd edn. Wiley, New York

    Google Scholar 

  16. Xiao J, Zhao Z (2003) Principles of surfactant application, 1st edn. Chemical Industry Press, Beijing

    Google Scholar 

  17. Tanford C (1973) The hydrophobic effect: formation of micelles and biological membranes. Wiley-Interscience, New York

    Google Scholar 

  18. Israelachvili JN (1985) Intermolecular and surface forces: with applications to colloidal and biological systems. Academic Press, London

    Google Scholar 

Download references

Acknowledgments

The authors are grateful for the financial support from the National Natural Science Foundation of China (20876023).

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Correspondence to Weihong Qiao.

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Qiao, W., Zhou, M. & Luo, L. Synthesis and Characterization of Novel Cationic Lipids Derived from Thio Galactose. J Surfact Deterg 17, 261–268 (2014). https://doi.org/10.1007/s11743-013-1474-0

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  • DOI: https://doi.org/10.1007/s11743-013-1474-0

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