Lipase-catalyzed synthesis of novel galactosylated cholesterol

来源 :Chinese Chemical Letters | 被引量 : 0次 | 上传用户:triumphis
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In an organic phase system,an enzymes lipase was used as a catalyst to synthesize galactosylated cholesterol,(5-cholesten-3b-yl)[(4-O-β-D-galactopyranosyl)D-glucitol-6]sebacate(CHS-SE-LA),which contains galactose residues.Its chemical structure was characterized by ESI-MS,and NMR.For HepG2 cells,the cellular fluorescence intensities of liposomes modified with CHS-SE-LA(GAL-FL) were as much as 2.6-fold(p < 0.01) control liposomes(FL).Moreover,the presence of excess galactose significantly inhibited the uptake of GAL-FL suggesting ASGPR mediated uptake.In conclusion,the novel galactosylated ligand CHS-SE-LA was synthesized by lipase-catalyzation and revealed a great potential as drug carrier materials for hepatocyte-selective targeting. In an organic phase system, an enzyme lipase was used as a catalyst to synthesize galactosylated cholesterol, (4-O-β-D-galactopyranosyl) D-glucitol-6] sebacate SE-LA), which contains galactose residues. Its chemical structure was characterized by ESI-MS, and NMR.For HepG2 cells, the cellular fluorescence intensities of liposomes modified with CHS-SE-LA -fold (p <0.01) control liposomes (FL). More over, the presence of excess galactose significantly inhibited the uptake of GAL-FL suggesting ASGPR mediated uptake. In conclusion, the novel galactosylated ligand CHS-SE- LA was synthesized by lipase- catalyzation and revealed a great potential as drug carrier materials for hepatocyte-selective targeting.
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