Lipase-catalyzed synthesis of novel galactosylated cholesterol

In an organic phase system, an enzymes lipase was used as a catalyst to synthesize galactosylated cholesterol, （5-cholesten-3b-yl）[（4-O-/%u-galactopyranosyl）u-glucitol-6] sebacate （CHS-SE-LA）, which contains galactose residues. Its chemical structure was characterized by ESI-MS, and NMR. For HepG2 c...

Full description

Saved in:
Bibliographic Details
Published in:Chinese chemical letters 2015-05, Vol.26 (5), p.543-546
Main Authors: Nie, Hua, Cheng, Yi, Zheng, Pin-Jing, Luo, Li-Hua, Zhang, Sheng-Yuan
Format: Article
Language:English
Subjects:
Asialoglycoprotein receptor
Cholesterol derivative
HepG2细胞
Lipase-catalyzed
Liposomes
半乳糖基
电喷雾质谱
糖化
胆固醇
脂肪酶
药物载体材料
酶催化合成
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In an organic phase system, an enzymes lipase was used as a catalyst to synthesize galactosylated cholesterol, （5-cholesten-3b-yl）[（4-O-/%u-galactopyranosyl）u-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.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2015.01.005