著者

Toshiaki Taira Yuki Ishizaki Shusei Yamamoto Kenichi Sakai Hideki Sakai Tomohiro Imura

出版者

Japan Oil Chemists' Society

雑誌

Journal of Oleo Science (ISSN:13458957)

巻号頁・発行日

vol.68, no.12, pp.1223-1230, 2019 (Released:2019-12-01)

参考文献数

42

被引用文献数

1 1

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We report the synthesis of amphiphilic dodecenyl phosphonic acid PC12 from vinylphosphonic acid, a reactive phosphonic acid intermediate. The trans-P-C=C moiety enabled PC12 to disperse well in water. Surface tension and dynamic light scattering measurements revealed that PC12 exhibited high surface activity and reduced the surface tension of water from 72.0 to 23.6 mN/m, thereby resulting in the spontaneous formation of aggregates even in a dilute aqueous solution (critical aggregation concentration (CAC) = 4.8 × 10–4 M). In contrast to modern lipids with double-tailed structures, the PC12 of simple singletailed structure spontaneously formed bilayered vesicles, without an external energy supply. Compared with the strength of hydrogen bonds formed by the long, saturated alkyl chain of dodecyl phosphonic acid (DPA), the strength of PC12 intermolecular hydrogen bonds was weaker. The melting point of PC12 was approximately 20°C lower than that of DPA. These results indicate that the trans-P-C=C moiety was considerably important for spontaneous vesicle formation in water. Preliminary modeling of the morphological transitions of the closed bilayer structures in the vesicles was then conducted, by varying the pH and adding an α-helical peptide scaffold.

著者

Masaaki Akamatsu Taiki Suzuki Kazuki Kobayashi Koji Tsuchiya Kenichi Sakai Hideki Sakai

出版者

Japan Oil Chemists' Society

雑誌

Journal of Oleo Science (ISSN:13458957)

巻号頁・発行日

vol.68, no.7, pp.659-664, 2019 (Released:2019-07-01)

参考文献数

21

被引用文献数

3 4

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This report focuses on acceleration of the recombination of lophyl radicals with a lophine dimer derivative by forming molecular assemblies. A newly synthesized cationic amphiphilic lophine dimer formed molecular assemblies with a diameter of ~220 nm in an aqueous medium. When the molecular assemblies were formed, the rate of recombination of lophyl radicals, produced by ultraviolet light irradiation, was accelerated 50,000-fold compared to that in an organic solvent. The rate enhancement is likely derived from the short diffusion distance of the lophyl radicals in the molecular assemblies. These results revealed that accumulation of the lophine dimers via self-assembly remarkably accelerated the recombination of lophyl radicals. This novel photoisomerization system could rapidly control the interfacial properties or morphologies of molecular assemblies when used for applications, such as efficient delivery of drugs or active components.