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

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Phospholipid <b>1a</b> bearing 2-nitrobenzyl ester moieties as a photocleavable group at the terminal of alkyl chains was synthesized from the corresponding terminal carboxy-bearing phospholipid <b>2</b> by the reaction with 2-nitrophenyl-substituted diazomethane. Phospholipid, <b>1b</b> bearing <i>α</i>-methyl-2-nitrobenzyl group, <b>1c</b> bearing 4,5-dimethoxy-2-nitrobenzyl group, and <b>1d</b> bearing <i>α</i>-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 <b>1b</b> ≥ <b>1d</b> > <b>1a</b> > <b>1c</b>. Liposomes of <b>1a</b>—<b>1d</b> 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 : <b>1b</b> ≥ <b>1d</b> > <b>1c</b> > <b>1a</b> is consistent with that of photolysis rates except for <b>1c</b>, which has poor retention of the dye.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(8), 1923-1929, 1998-08-15

    The Chemical Society of Japan

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