Skip to main content
SpringerLink
Log in

Vesicles Comprising Dimethylaminopropyl Octadecanamide, Stearic Acid, and Carboxyhexadecyl Disulfide and Their Release Property under Reducing Condition

  • Research Paper
  • Published:
Biotechnology and Bioprocess Engineering Aims and scope Submit manuscript

Abstract

Vesicles comprising dimethyl aminopropyl octadecanamide (DMAPODA), stearic acid (SA), and carboxyhexadecyl disulfide (CHDDS) were prepared as reduction-responsive carriers. Vesicular particles were found on TEM micrographs and the diameter fell within 100–400 nm. The hydrodynamic mean diameter increased with increasing the content of CHDDS. The zeta potential was lowered by the incorporation of CHDDS into the vesicular membrane. Vesicle whose DMAPODA/SA/ CHDDS molar ratio was 1/1/5 exhibited one endothermic peak around 50.9°C, indicating that the vesicular membrane was homogeneous in the composition. Strong signals were found in 500–540 cm-1 in the Raman spectrum of vesicles, suggesting that the disulfide lipid (i.e. CHDDS) was incorporated into the vesicular membranes. Vesicles containing CHDDS released rhodamine B in dithiothreitol (DTT, a reducing agent) concentration-dependent manner. The DTTsensitivity of the vesicles in terms of release was higher as the CHDDS content was higher.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Alexandridis, P. and B. Lindman (2000) Amphiphilic molecules: small and large. pp. 1–12. In: P. Alexandridis and B. Lindman (eds.). Amphiphilic Block Copolymers: Self-assembly and Applications. Elsevier, Amsterdam, Netherlands.

    Google Scholar 

  2. Markvoort, A. J., K. Pieterse, M. N. Steijaert, P. Spijker, and P. A. J. Hilbers (2005) The bilayer-vesicle transition is entropy driven. J. Phys. Chem. B. 109: 22649–22654.

    Article  CAS  Google Scholar 

  3. Mai, Y. and A. Eisenberg (2012) Self-assembly of block copolymers. Chem. Soc. Rev. 41: 5969–5985.

    Article  CAS  Google Scholar 

  4. Goetz, R. and R. Lipowsky (1998) Computer simulations of bilayer membranes: self-assembly and interfacial tension. J. Chem. Phys. 108: 7397–7409.

    Article  CAS  Google Scholar 

  5. Stuart, M. C. A. and E. J. Boekema (2007) Two distinct mechanisms of vesicle-to-micelle and micelle-to-vesicle transition are mediated by the packing parameter of phospholipid-detergent systems. Biochim. Biophys. Acta. 1768: 2681–2689.

    Article  CAS  Google Scholar 

  6. Kumar, V. V. (1991) Complementary molecular shapes and additivity of the packing parameter of lipids. Proc. Natl. Acad. Sci. USA. 88: 444–448.

    Article  CAS  Google Scholar 

  7. Antonietti, M. and S. Förster (2003) Vesicles and liposomes: a self-assembly principle beyond lipids. Adv. Mater. 15: 1323–1333.

    Article  CAS  Google Scholar 

  8. Balazs, D. A. and W. T. Godbey (2011) Liposomes for use in gene delivery. J. Drug Deliv. 2011: 326497.

    Article  Google Scholar 

  9. Taraschi, T. F., A. T. Van der Steen, B. De Kruijff, C. Tellier, and A. J. Verkleij (1982) Lectin-receptor interactions in liposomes: Evidence that binding of wheat germ agglutinin to glycoproteinphosphatidylethanolamine vesicles induces nonbilayer structures. Biochemistry. 21: 5756–5764.

    Article  CAS  Google Scholar 

  10. Litzinger, D. C. and L. Huang (1992) Phosphatidylethanolamine liposomes: drug delivery, gene transfer and immunodiagnostic applications. Biochim. Biophys. Acta. 1113: 201–227.

    Article  CAS  Google Scholar 

  11. Pinnaduwage, P. and L. Huang (1988) β-Galactosidase-induced destabilization of liposome composed of phosphatidylethanolamine and ganglioside GM1. Biochim. Biophys. Acta. 939: 375–382.

    Article  CAS  Google Scholar 

  12. Lee, E. O., J. G. Kim, and J. D. Kim (1992) Induction of vesicleto- micelle transition by bile salts for DOPE vesicles incorporating immunoglobulin G. J. Biochem. 112: 671–676.

    Article  CAS  Google Scholar 

  13. Seo, D. S., J. C. Kim, H. H. Sohn, W. G. Cho, S. U. Lee, E. Y. Kim, G. Tae, J. D. Kim, S. Y. Lee, and H. Y. Lee (2004) Two-dimensional packing patterns of amino acid surfactant and higher alcohols in an aqueous phase and their associated packing parameters. J. Colloid. Interface Sci. 273: 596–603.

    Article  CAS  Google Scholar 

  14. Dayan, N. and E. Touitou (2000) Carriers for skin delivery of trihexyphenidyl HCl: ethosomes vs. liposomes. Biomaterials. 21: 1879–1885.

    Article  CAS  Google Scholar 

  15. Bangham, A. D. and R. W. Horne (1964) Negative staining of phospholipids and their structural modification by surface-active agents as observed in the electron microscope. J. Mol. Biol. 8: 660–668.

    Article  CAS  Google Scholar 

  16. White, J. and A. Helenius (1980) pH-dependent fusion between the Semliki Forest virus membrane and liposomes. Proc. Natl. Acad. Sci. USA. 77: 3273–3277.

    Article  CAS  Google Scholar 

  17. Wang, M. H. and J. C. Kim (2014) Vesicles composed of fatty acid and N-[3-(dimethylamino)propyl]-octadecanamide: effect of fatty acid chain length on physicochemical properties of vesicles. Drug Dev. Ind. Pharm. 40: 318–324.

    Article  CAS  Google Scholar 

  18. Kim, J. C., M. E. Song, M. J. Kim, E. J. Lee, S. K. Park, M. J. Rang, and H. J. Ahn (2002) Preparation and characterization of Triclosan-containing vesicles. Colloids Surf. B Biointerfaces. 26: 235–241.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF- 2018R1D1A1B07043439) and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (No. 2018R1A6A1A03025582).

Author information

Authors and Affiliations

  1. Department of Medical Biomaterials Engineering, College of Biomedical Science and Institute of Bioscience and Biotechnology, Kangwon National University, Chuncheon, 24341, Korea

    Jin Ah Kim & Jin-Chul Kim

Authors
  1. Jin Ah Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jin-Chul Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jin-Chul Kim.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kim, J.A., Kim, JC. Vesicles Comprising Dimethylaminopropyl Octadecanamide, Stearic Acid, and Carboxyhexadecyl Disulfide and Their Release Property under Reducing Condition. Biotechnol Bioproc E 25, 690–698 (2020). https://doi.org/10.1007/s12257-019-0456-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12257-019-0456-0

Keywords

Search

Navigation