title: Photo responsive monoolein cubic phase containing coumarin-Tween 20 conjugates.
abstract: 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 ¹H 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.
authors.affiliation: College of Biomedical Science and Institute of Bioscience and Biotechnology, Kangwon National University, Chuncheon, Kangwon-do, Korea.
authors.forename: Jing
authors.initials: J
authors.lastname: Dai
authors.forename: Jin-Chul
authors.initials: JC
authors.lastname: Kim
mesh_terms: D000925:Anticoagulants / Q000737:chemistry* / Q000528:radiation effects; D003374:Coumarins / Q000737:chemistry* / Q000528:radiation effects; D019281:Dimerization; D016503:Drug Delivery Systems; D004355:Drug Stability; D005452:Fluoresceins / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D005989:Glycerides / Q000737:chemistry* / Q000528:radiation effects; D006358:Hot Temperature; D006923:Hymecromone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D014677:Pharmaceutical Vehicles / Q000737:chemistry* / Q000528:radiation effects; D044367:Phase Transition; D055668:Photochemical Processes; D011136:Polysorbates / Q000737:chemistry* / Q000528:radiation effects; D012995:Solubility; D013501:Surface-Active Agents / Q000737:chemistry / Q000528:radiation effects; D014466:Ultraviolet Rays; D014468:Umbelliferones / Q000737:chemistry / Q000528:radiation effects
chemical_list: D000925:Anticoagulants; D003374:Coumarins; D005452:Fluoresceins; D005456:Fluorescent Dyes; D005989:Glycerides; D014677:Pharmaceutical Vehicles; D011136:Polysorbates; D013501:Surface-Active Agents; D014468:Umbelliferones; C024098:6-carboxyfluorescein; D006923:Hymecromone; C031477:7-hydroxycoumarin; C041982:7-(chlorocarbonylmethoxy)-4-methylcoumarin; C030123:coumarin; C005953:monoolein