Design, synthesis and preliminary bio-evaluation of glucose-cholesterol derivatives as ligands for brain targeting liposomes

A series of glucose-cholesterol derivatives 8a-8e as ligands for brain targeting liposomes were synthesized. The preparation of compound 6 involved temporary protection of glucose with chlorotrimethylsilicane and hexamethyldisilazane followed by selectively hydrolyzed. The known cholesteryl tosylate...

Full description

Saved in:
Bibliographic Details
Published in:Chinese chemical letters 2011-07, Vol.22 (7), p.831-834
Main Authors: Lei, Fan, Fan, Wei, Li, Xian Kun, Wang, Shan, Hai, Li, Wu, Yong
Format: Article
Language:English
Subjects:
Brain target
GLUT 1 transporter
Liposome ligands
Synthesis
Tegafur
合成
生物评价
生物配体
胆固醇
葡萄糖
血脑屏障
衍生物
靶向脂质体
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:A series of glucose-cholesterol derivatives 8a-8e as ligands for brain targeting liposomes were synthesized. The preparation of compound 6 involved temporary protection of glucose with chlorotrimethylsilicane and hexamethyldisilazane followed by selectively hydrolyzed. The known cholesteryl tosylate 1 were coupled to ethylene glycols to afford alcohol 2a-2e. Substitution and deprotection of alcohol 2a-2e furnished the acids 4a-4e, which was condensed with compound 6 to get compounds 7a-7e, and then was deprotected in tetrahydrofuran with TFA to obtain the title compounds. As a model drug, tegafur was entrapped by liposomes coupled with 8b, and preliminary in vivo evaluation shown 8b could enhance the ability of liposomes delivering tegafur across the blood brain barrier.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2010.12.056