Synthesis of Sulfated Cyclodextrin Amphiphiles with Liposomal Encapsulation Properties

Tetsuya Furuike^*, Koichi Nasu, Hiroshi Tamura

Faculty of Chemistry, Materials and Engineering, Kansai University, Suita, Japan.

DOI: 10.4236/jeas.2015.53012                

Abstract

A novel class of amphiphiles with sulfate groups at the C-6 position and palmitoyl groups at the C-2, 3 positions of α-, β-, and γ-cyclodextrin (CD) were efficiently synthesized. These compounds formed stable monolayers with high collapse pressures at the air-water interface. The mixed monolayer behaviors of the 6-O-sulfated CD amphiphiles (SO₃-CDC₁₆) in the presence of dipalmitoyl phosphatidylcholine (DPPC) and cholesterol were discussed using the surface pressure-molecular area (π-A) isotherms. The collapse pressures showed maxima at molar ratios of SO₃-CDC₁₆ lower than 10 mol%. A morphological analysis of the liposomes containing DPPC and 4 mol% SO₃-CDC₁₆ formed in PBS was carried out using transmission electron microscopy with negative staining, and vesicles with maximum diameters of 350-500 nm were observed. Moreover, the releasing ability of these liposomes was examined using a fluorescent compound, calcein. It was clearly shown that liposomes containing SO₃-CDC₁₆ could release encapsulated calcein more easily than liposomes consisting only of DPPC, and that the release rate depended on the phase transition temperature of the SO₃-CDC₁₆ included in the liposome membrane.

Keywords

Cyclodextrin, Amphiphile, Liposome, Encapsulation

Conflicts of Interest

The authors declare no conflicts of interest.

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