Skip to main content
Log in

Preparation of dimethylaminopropyl octadecanamide/stearic acid vesicles incorporating azobenzene and their UV-responsive release property

  • Original Contribution
  • Published:
Colloid and Polymer Science Aims and scope Submit manuscript

Abstract

UV-responsive vesicle was prepared by incorporating azobenzene in the vesicular membrane composed of dimethylaminopropyl octadecanamide (DMAPODA) and stearic acid (SA). Azobenzene intercalated in the vesicular membrane underwent cis-to-trans isomerization under the UV irradiation, confirmed by UV spectroscopy. The phase transition temperature of vesicle was found to be around 51.2 °C by differential scanning calorimetry. Using a negative staining technique, the vesicles were found as circular and irregular-shaped particles on the TEM photo. The mean hydrodynamic diameter of vesicles increased from 199.4 to 1597.3 nm when the lipid/azobenzene ratio increased from 100/0 to 100/5. The zeta potential of DMAPODA/SA vesicle decreased from about + 60 mV to – 60 mV when the pH value of medium increased from 3.0 to 10.0, and the inclusion of azobenzene in the vesicular membrane had little effect on the zeta potential. UV irradiation markedly promoted the release of carboxylic fluorescein loaded in vesicle incorporating azobenzene, possibly because the cis-to-trans photoisomerization would disturb the well-ordered crystalline structure of the vesicular membrane.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Aulton ME (2007) Aulton's pharmaceutics: the design and manufacture of medicines. Churchill Livingstone

  2. Balazs DA, Godbey W (2011) Liposomes for use in gene delivery. Journal of Drug Delivery, 2011

  3. Bandara HD, Burdette SC (2012) Photoisomerization in different classes of azobenzene. Chem Soc Rev 41:1809–1825

    Article  CAS  Google Scholar 

  4. Bangham AD, Horne R (1964) Negative staining of phospholipids and their structural modification by surface-active agents as observed in the electron microscope. J Mol Biol 8:660–IN610

    Article  CAS  Google Scholar 

  5. Cicogna F, Domenichelli I, Coiai S, Bellina F, Lessi M, Spiniello R, Passaglia E (2016) Structural, thermal and photo-physical data of azo-aromatic TEMPO derivatives before and after their grafting to polyolefins. Data Brief 6:562–570

    Article  Google Scholar 

  6. Cunningham WP, Morré DJ, Mollenhauer H (1966) Structure of isolated plant Golgi apparatus revealed by negative staining. J Cell Biol 28:169–179

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Goldenbogen Br, Brodersen N, Gramatica A, Loew M, Liebscher Jr, Herrmann A, Egger H, Budde B, Arbuzova A (2011)Reduction-sensitive liposomes from a multifunctional lipid conjugate and natural phospholipids: reduction and release kinetics and cellular uptake. Langmuir 27:10820–10829

    Article  CAS  Google Scholar 

  9. Hafez IM, Cullis PR (2001) Roles of lipid polymorphism in intracellular delivery. Adv Drug Deliv Rev 47:139–148

    Article  CAS  Google Scholar 

  10. Khalil RA, Al-hakam AZ (2014) Theoretical estimation of the critical packing parameter of amphiphilic self-assembled aggregates. Appl Surf Sci 318:85–89

    Article  CAS  Google Scholar 

  11. Kim JA, Kim J-C(2018) Temperature and electric field-triggerable liposomes incorporating poly (hydroxyethyl acrylate-co-hexadecyl acrylate-co-carboxyethyl acrylate). J Ind Eng Chem 62:383–391

    Article  CAS  Google Scholar 

  12. Kono K, Hayashi H, Takagishi T (1994)Temperature-sensitive liposomes: liposomes bearing poly (N-isopropylacrylamide). J Control Release 30:69–75

    Article  CAS  Google Scholar 

  13. Kono K, Ozawa T, Yoshida T, Ozaki F, Ishizaka Y, Maruyama K, Kojima C, Harada A, Aoshima S (2010) Highly temperature-sensitive liposomes based on a thermosensitive block copolymer for tumor-specific chemotherapy. Biomaterials 31:7096–7105

    Article  CAS  Google Scholar 

  14. Koshima H, Ojima N, Uchimoto H (2009) Mechanical motion of azobenzene crystals upon photoirradiation. J Am Chem Soc 131:6890–6891

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Kwon K, Kim J-C(2017) Preparation of liposome bearing disulfide proteinoid and its reduction-responsive release property. J Biomater Sci Polym Ed 28:1365–1381

    Article  CAS  Google Scholar 

  17. Leroux J-C, Roux E, Le Garrec D, Hong K, Drummond DC (2001)N-isopropylacrylamide copolymers for the preparation of pH-sensitive liposomes and polymeric micelles. J Control Release 72:71–84

    Article  CAS  Google Scholar 

  18. Ohline SM, Campbell ML, Turnbull MT, Kohler SJ (2001) Differential scanning calorimetric study of bilayer membrane phase transitions. A biophysical chemistry experiment. J Chem Educ 78:1251

    Article  CAS  Google Scholar 

  19. Paasonen L, Laaksonen T, Johans C, Yliperttula M, Kontturi K, Urtti A (2007) Gold nanoparticles enable selective light-induced contents release from liposomes. J Control Release 122:86–93

    Article  CAS  Google Scholar 

  20. Sagar GH, Arunagirinathan M, Bellare JR (2007)Self-assembled surfactant nano-structures important in drug delivery: a review

  21. Shum P, Kim J-M, Thompson DH (2001) Phototriggering of liposomal drug delivery systems. Adv Drug Deliv Rev 53:273–284

    Article  CAS  Google Scholar 

  22. Taylor KM, Morris RM (1995) Thermal analysis of phase transition behaviour in liposomes. Thermochim Acta 248:289–301

    Article  CAS  Google Scholar 

  23. Wang MH, Kim J-C(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 

  24. Yang X, Kim J-C(2009)pH-sensitive cationic vesicles prepared using N-[3-(Dimethylamino) propyl]-Octadecanamide and stearic acid. Mol Cryst Liq Cryst 508:200/[562]–213/[575]

    Article  Google Scholar 

  25. Yang X, Lee HY, You SG, Kim J-C(2009)pH-and temperature-dependent release from cationic vesicles coexisting with copolymer of N-isopropylacrylamide and methacrylic acid. Colloids Surf A Physicochem Eng Asp 348:109–115

    Article  CAS  Google Scholar 

  26. Zignani M, Drummond DC, Meyer O, Hong K, Leroux J-C(2000) In vitro characterization of a novel polymeric-based pH-sensitive liposome system. Biochim Biophys Acta (BBA)-Biomembr 1463:383–394

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by the Technology Development Program (S2911350) funded by the Ministry of SMEs and Startups (MSS, Korea). This research was supported by 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

Authors

Corresponding author

Correspondence to Jin-Chul Kim.

Ethics declarations

Conflict of interests

The authors declare that they have no conflict of interest.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kim, J.A., Long, W. & Kim, JC. Preparation of dimethylaminopropyl octadecanamide/stearic acid vesicles incorporating azobenzene and their UV-responsive release property. Colloid Polym Sci 299, 741–749 (2021). https://doi.org/10.1007/s00396-020-04806-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00396-020-04806-1

Keywords

Navigation