Effects of Oligosaccharides Having the Glucuronic Acid Residue on Base-Catalyzed Prostaglandin E_2 Dehydration and Isomerization
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概要
- 論文の詳細を見る
Examination was made of the effects of 2-(trimethylsilyl)ethyl 4-Ο-methyl-β-D-glucopyranosyluronic acid-(1→6)-β-D-galactopyranoside (A), 2-(trimethylsilyl)ethyl 4-Ο-methyl-β-D-glucopyranosyluronic acid-(1→6)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranoside (B) and N, N,N-tri-{5-[4-Ο-methyl-β-D-glucopyranosyluronic acid-(1→6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide (C), each possessing the glucuronic acid residue, on drug degradation. Oligosaccharide mixed micelles containing the nonionic surfactant, heptaethyleneglycol dodecylether (HED), were studied so as to assess oligosaccharides A∼C for drug stabilization potential. The nonionic surfactant was required since oligosaccharides A∼C do not form micelles in single systems. Base-catalyzed dehydration and then isomerization of prostaglandin E2 (PGE2), PGE2→PGA2→PGB2, were conducted as model experiments. The rate of the degradation of PGE2 with base was determined based on concentrations of PGA2 and PGB2 using high-performance liquid chromatography. Mixed oligosaccharide-HED micelles inhibited the dehydration and isomerization of PGE2, possibly owing to suppression of the approach of OH- as catalysis toward PGE2 in mixed oligosaccharide-HED micelles by electrostatic repulsion between negatively charged micellar surfaces and OH-. The clusterized molecular structure of oligosaccharide C was the reason for the inhibition of both these processes. Oligosaccharide C may possibly be situated on the micellar surface and this would lead to greater steric shielding and the above electrostatic repulsion compared to A or B.
- 日本油化学会の論文
- 2001-07-01
著者
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TAKEDA Tadahiro
Kyoritsu University of Pharmacy
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竹田 忠紘
Kyoritsu College Of Pharmacy
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竹田 忠紘
Faculty Of Pharmaceutical Sciences Nagoya City University
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YOKOYAMA Shoko
Kyoritsu College of Pharmacy
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Taguchi Tomiko
Laboratory Of Plant Pathology And Genetic Engineering Faculty Of Agriculture Okayama University
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HADA Noriyasu
Kyoritsu College of Pharmacy
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Hada N
Kyoritsu University Of Pharmacy
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Yokoyama Shoko
Kyushu University Of Health And Welfare
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Takeda T
Kyoritsu University Of Pharmacy
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Takeda Tadahiro
Kyoritsu College Of Pharmacy
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Takeda Tadahiro
Kyoritsu College Of Pharmac
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