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Biochim Biophys Acta. 2005 Dec 30;1720(1-2):28-34. Epub 2005 Dec 6.

Photoisomerisable cholesterol derivatives as photo-trigger of liposomes: effect of lipid polarity, temperature, incorporation ratio, and cholesterol.

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  • 1Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.


Three cholesterol derivatives containing an azobenzene moiety with different polarities were designed and synthesized (AB lipids 1 to 3). The effects of structure, temperature and incorporation ratio on liposomes were studied, with the results showing that the polarity in 4-substituent and in some cases, 4'-substituent may be important for their incorporation feasibility and photoisomerizability in liposomes. Liposomes incorporated with AB lipid 3 could release multi-pulsatilely upon UV and visible light irradiation both in gel state and liquid crystal state of liposomes. An increase in the incorporation ratio of AB lipid 3 enhanced the amount of drug released greatly. Unlike other azobenzene photo-triggers reported, AB lipid 3 did not increase the spontaneous release of liposomes. Furthermore, cholesterol suppressed the spontaneous release of liposomes.

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