Citation: Fan Lei, Wei Fan, Xian Kun Li, Shan Wang, Li Hai, Yong Wu. Design, synthesis and preliminary bio-evaluation of glucose-cholesterol derivatives as ligands for brain targeting liposomes[J]. Chinese Chemical Letters, ;2011, 22(7): 831-834. doi: 10.1016/j.cclet.2010.12.056 shu

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

Key Laboratory of Drug Targeting and Drug Delivery Systems, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

Received Date: 1 November 2010

Fund Project: This work was supported by the National Natural Science Foundation of China (No.81072532).

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 TEA 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.
- Liposome ligands,
- Brain target,
- GLUT₁ transporter,
- Tegafur,
- Synthesis
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