Alkyl Chain Length Dependency in Hydrolysis of Liposomal Phosphatidylcholine by Dialkylphosphate

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概要

• 論文の詳細を見る

• Because an amphiphile with a positive or negative charge, shch as dialkylphosphate or stearylamine, is often added to liposomal phosphatidylcholine (PC) dispersions to prevent aggregation of the liposomes, we investigated the long-term stability of liposomes prepared from saturated PC in the presence of various amphiphiles. On storage of these liposomes at 40℃, PC was gradually hydrolyzed by dialkylphosphate, a negatively charged lipid, while neither stearylamine, a positively charged lipid, nor a non-charged lipid hydrolyzed PC at all. This hydrolysis of PC was examined using dialkylphosphates of various alkyl chain lengths (C10,C12,C14,C16,C18 and C20) and PC with different fatty acyl chain lengths (C14,C16 and C18). The rate of hydrolysis was maximum when the alkyl chain length of dialkylphosphate was almost equal to the fatty acyl chain length of PC. That is, the hydrolysis of dimyristoyl (C14) and dipalmitoyl (C16) acyl chains of PC was accelerated most by the incorporation of dimyristylphosphate (C14) and dipalmitylphosphate (C16), respectively. Distearoyl (C18) acyl chains of PC were hydrolyzed effectively by the incorporation of distearylphosphate (C18) as well as dipalmitylphosphate (C16). The hydrolysis did not occur when methyl dipalmitylphosphate was added instead of dipalmitylphosphate, or when the liposomal structure was decomposed by adding ethanol. These results suggest that dialkylphosphate and PC are aligned head to tail in liposomes and that the phosphate functional group causes the hydrolysis of the esters of PC.The incorporation of cholesterol into PC bilayers suppressed the hydrolysis of PC above the phase transition temperature (T_c) of PC, but increased it below the T_c. The hydrolysis of PC by dialkylphosphate appears to depend on membrane fluidity and to be accelerated with increased membrane fluidity, because cholesterol reduces the fluidity of the liposomal membrane above the T_c and enhances it below the T_c.

• 公益社団法人日本薬学会の論文
• 1995-10-15

著者

• 長野 哲雄

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 広部 雅昭

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 荒金 久美

  Research Laboratory, KOSE Corporation

• 林 喜実江

  Research Laboratory, KOSE Corporation

• 内藤 昇

  Research Laboratory, KOSE Corporation

• 広部 雅昭

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 広部 雅昭

  東京大学薬学部:文部省

• 荒金 久美

  Research Laboratory Kose Corporation

• 内藤 昇

  Research Laboratory Kose Corporation

• Hayashi K

  Graduate School Of Medicine And Pharmaceutical Sciences For Research University Of Toyama

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