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.
Similar content being viewed by others
References
Aulton ME (2007) Aulton's pharmaceutics: the design and manufacture of medicines. Churchill Livingstone
Balazs DA, Godbey W (2011) Liposomes for use in gene delivery. Journal of Drug Delivery, 2011
Bandara HD, Burdette SC (2012) Photoisomerization in different classes of azobenzene. Chem Soc Rev 41:1809–1825
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
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
Cunningham WP, Morré DJ, Mollenhauer H (1966) Structure of isolated plant Golgi apparatus revealed by negative staining. J Cell Biol 28:169–179
Dayan N, Touitou E (2000) Carriers for skin delivery of trihexyphenidyl HCl: ethosomes vs. liposomes. Biomaterials 21:1879–1885
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
Hafez IM, Cullis PR (2001) Roles of lipid polymorphism in intracellular delivery. Adv Drug Deliv Rev 47:139–148
Khalil RA, Al-hakam AZ (2014) Theoretical estimation of the critical packing parameter of amphiphilic self-assembled aggregates. Appl Surf Sci 318:85–89
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
Kono K, Hayashi H, Takagishi T (1994)Temperature-sensitive liposomes: liposomes bearing poly (N-isopropylacrylamide). J Control Release 30:69–75
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
Koshima H, Ojima N, Uchimoto H (2009) Mechanical motion of azobenzene crystals upon photoirradiation. J Am Chem Soc 131:6890–6891
Kumar V (1991) Complementary molecular shapes and additivity of the packing parameter of lipids. Proc Natl Acad Sci 88:444–448
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
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
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
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
Sagar GH, Arunagirinathan M, Bellare JR (2007)Self-assembled surfactant nano-structures important in drug delivery: a review
Shum P, Kim J-M, Thompson DH (2001) Phototriggering of liposomal drug delivery systems. Adv Drug Deliv Rev 53:273–284
Taylor KM, Morris RM (1995) Thermal analysis of phase transition behaviour in liposomes. Thermochim Acta 248:289–301
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
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]
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
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
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
Corresponding author
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
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00396-020-04806-1