Syntheses of Phospholipids Containing 2-Nitrobenzyl Ester Moieties at the Terminals of Alkyl Chains and Properties of Photodegradable Liposomes from the Lipids.

DOI DOI PDF Web Site 被引用文献6件 参考文献130件
  • Yamaguchi Kazuo
    Department of Materials Science, Faculty of Science, Kanagawa University
  • Tsuda Yoshihiro
    Department of Materials Science, Faculty of Science, Kanagawa University
  • Shimakage Taka-aki
    Department of Materials Science, Faculty of Science, Kanagawa University
  • Kusumi Akihiro
    Department of Biological Science, Graduate School of Science, Nagoya University

書誌事項

タイトル別名
  • Syntheses of Phospholipids Containing 2
公開日
1998
DOI
  • 10.1246/bcsj.71.1923
  • 10.1002/chin.199848254
公開者
公益社団法人 日本化学会

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説明

Phospholipid 1a bearing 2-nitrobenzyl ester moieties as a photocleavable group at the terminal of alkyl chains was synthesized from the corresponding terminal carboxy-bearing phospholipid 2 by the reaction with 2-nitrophenyl-substituted diazomethane. Phospholipid, 1b bearing α-methyl-2-nitrobenzyl group, 1c bearing 4,5-dimethoxy-2-nitrobenzyl group, and 1d bearing α-methyl-4,5-dimethoxy-2-nitrobenzyl group were similarly synthesized by the use of the respective diazo compounds. The order of photolysis rates of 2-nitrobenzyl ester linkage of phospholipids by ultrahigh-pressure mercury lamp is 1b ≥ 1d > 1a > 1c. Liposomes of 1a—1d containing calcein in the inner aqueous layer were prepared by vortexing, sonication, and gel-filtration. UV irradiation resulted in fast release of the entrapped fluorescence dye. The order of release rates : 1b ≥ 1d > 1c > 1a is consistent with that of photolysis rates except for 1c, which has poor retention of the dye.

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