Journal
DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY
Volume 39, Issue 9, Pages 1457-1463Publisher
TAYLOR & FRANCIS LTD
DOI: 10.3109/03639045.2012.728225
Keywords
Monoolein cubic phase; coumarin-tween 20 conjugate; dimerization; interfacial activity; photo-responsive release
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Funding
- Ministry of Education, Science & Technology (MEST)
- National Research Foundation of Korea (NRF)
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Photo-responsive monoolein (MO) cubic phase was developed by incorporating coumarin-Tween 20 conjugate in the cubic phase. 7-chlorocarbonylmethoxycoumarin was obtained from 7-hydroxycoumarin through three-step reactions with the yield of 19.8% and it was conjugated to the head group of Tween 20. The molar ratio of the coumarin derivative/Tween 20 in the conjugate was about 1/1 on H-1 NMR spectrum. The cubic phase was prepared by melting the mixture of MO/conjugate (100/0.88, w/w) and hydrating the molten mixture with 5(6)-carboxyfluorescein (CF) solution. UV irradiation (254 nm and/or 365 nm) for 3 h resulted in 1.27% to 2.69% reduction in the double bond of MO but the cubic phase was stable in terms of its integrity under the UV irradiation. The release of CF from coumarin-Tween 20 conjugate-incorporated cubic phase was somewhat suppressed by being subjected to the UV irradiation. The head groups of coumarin-Tween 20 conjugate will be cross-linked so the diffusion in the water channel will be suppressed.
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