Citation: Hua Nie, Yi Cheng, Pin-Jing Zheng, Li-Hua Luo, Sheng-Yuan Zhang. Lipase-catalyzed synthesis of novel galactosylated cholesterol[J]. Chinese Chemical Letters, ;2015, 26(5): 543-546. doi: 10.1016/j.cclet.2015.01.005 shu

Lipase-catalyzed synthesis of novel galactosylated cholesterol

1.
a College of Traditional Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China;
2.
b Medical College of Jiaying University, Meizhou 514031, China

Corresponding author: Yi Cheng,
Received Date: 31 January 2014
Available Online: 19 December 2014
Fund Project: This work was financially supported by the Ph.D. Programs FoundationofMinistry ofEducationofChina (No.20134425110010) (No.20134425110010)

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.
- Cholesterol derivative,
- Liposomes,
- Asialoglycoprotein receptor,
- Lipase-catalyzed
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沈阳化工大学材料科学与工程学院沈阳 110142