| Summary: | 碩士 === 義守大學 === 生物技術與化學工程研究所碩士班 === 97 === This research is directed towards the study on the formation and stabilization of lyotropic liquid crystalline phases, particularly reversed cubic and reversed hexagonal phases since these two phases are quite suitable as drug release device.
In order to stabilize lyotropic liquid crystalline phases by polymerization, a polymerizable diene group is incorporated into monoolein, which is well known for the formation of stable reversed cubic phases in excess water at room temperature. The structures of the designed compound and monolein are as follows:
At this point,we have succeeded in the synthesis of (2E,4E,13Z)-2,3-dihydroxypropyl docosa-2,4,13-trienoate. The phase behaviour of this compound is as follows:
Compared with monoolein, the tendency to form reversed cubic and reversed hexagonal phases is reduced probably because the incorporation of diene group in the hydrophilic head group increases the size of the hydrophilic side and decreases the surfactant packing parameter (g).
In the second part of this study, we focus on the preparation of reversed cubic and reversed hexagonal phases of monosaccharides, which are known to be difficult to form reversed phases because of their large head groups. Thus we employ polypropyleneglycol as a hydrophobic chain end since the structure has a methyl side group to increase the size of the hydrophobic side and increase the surfactant packing parameter (g). Furthermore, the ether flexible linkage should be able to facilitate the packing of hydrophobic chain end in the reversed phases. The designed compound is shown in the following:
Compared with monoalkyl glycosides, 1-O-phytanyl-β-D-glucoside and 1,3-di-O-phytanyl-2-O-(β-D-glucosyl)glycerol, the new design has considerably enhanced the possibility of the formation of the reversed phases of monosaccharide compounds.
In a further attempt, the mixing behavior of B with A (N-(tetrahydro-2,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-3-yl)oleamide)is studied to explore the possibility of B to enhance the formation of the reversed phases of other similar compounds. Nevertheless, the effect is mediocre at this moment.
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