引用本文:
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
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
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
Design, synthesis and preliminary bio-evaluation of glucose-cholesterol derivatives as ligands for brain targeting liposomes
摘要:
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.
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关键词:
- Liposome ligands
- / Brain target
- / GLUT1 transporter
- / Tegafur
- / Synthesis
English
Design, synthesis and preliminary bio-evaluation of glucose-cholesterol derivatives as ligands for brain targeting liposomes
Abstract:
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.
-
Key words:
- Liposome ligands
- / Brain target
- / GLUT1 transporter
- / Tegafur
- / Synthesis
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