Abstract
Giant vesicles (GVs) have attracted attention as functional materials because they can encapsulate both hydrophilic and hydrophobic compounds. For next generation functional GVs, both tolerance and stimuli-sensitivity are needed. So far, vesicles tolerant to acidic or basic conditions were generated using a mixture of cationic lipids and fatty acids. Here, to create functional GVs that are tolerant to a wide pH range but sensitively respond at below a specific pH, the behaviour of GVs composed of a cationic lipid with an imine bond and oleic acid was investigated. Even though the GVs prepared by the film swelling method were tolerant to strongly acidic conditions, GVs without oleic acid gradually shrank, accompanied by the generation of oil droplets at the same pH. 1H NMR analysis revealed that during hydration of the film, the imine bond hydrolysed to provide a cationic surfactant and an oil component in the presence of oleic acid due to its own Lewis basicity, suggesting the dissociation of oleic acid. The results of fluorescence spectroscopy using an environment-responsive probe and IR spectroscopy indicated that the GV tolerance originated from the intermolecular interactions of cationic lipids and anionic oleate.
Highlights
Amphiphilic molecules form various molecular aggregates in water depending on their hydrophilicity and hydrophobicity
To create functional Giant vesicles (GVs) that are tolerant to a wide pH range but sensitively respond at below a specific pH, the behaviour of GVs composed of a cationic lipid with an imine bond and oleic acid was investigated
Using either a uorescent lipid, Texas Red-1,2-dihexadecanoyl-snglycero-3-phosphoethanolamine trimethylammonium salt (DHPE), or Uranine, a water-soluble uorescent compound, GVs were observed in the dispersion without HCl and NaOH under a confocal laser microscope
Summary
Amphiphilic molecules form various molecular aggregates in water depending on their hydrophilicity and hydrophobicity. Vesicles in which the bilayer membranes are closed like a bag can encapsulate both hydrophilic and hydrophobic compounds because of their characteristic structure. The introduction of transmembrane protein-like functional molecules into the vesicular membrane provides notable properties, such as releasing[1,2,3,4,5] and uptaking compounds from the external and internal phases, respectively, under speci c conditions.[6,7,8] Vesicles are useful as micro reaction elds for analysis in biological systems and as tissue markers.[9,10,11,12] In addition, it is well known that polymersomes of amphipathic polymers are more stable than vesicles composed of low-molecular-weight amphiphiles under various conditions.
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