Synthesis of Archaeal Bipolar Lipid Analogues: A Way to Versatile Drug/Gene Delivery Systems

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• 作者：Micka&euml ; lle Brard ; Cé ; line Lainé ; Gildas Ré ; thoré ; Isabelle Laurent ; Cé ; cile Neveu ; Loï ; c Lemiè ; gre ; Thierry Benvegnu
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 26, 2007
• 年：2007
• 卷：72
• 期：22
• 页码：8267 - 8279
• 全文大小：414K
• 年卷期：v.72,no.22(October 26, 2007)
• ISSN：1520-6904

文摘

A synthetic route for the preparation of symmetrical and unsymmetrical archaeal tetraether-like analogueshas been described. The syntheses are based upon the elaboration of hemimacrocyclic tetraether lipidcores from versatile building blocks followed by simultaneous or sequential introduction of polar headgroups. Functionalizations of the tetraether lipids with neutral lactose or phosphatidylcholine polar headsand cationic glycine betaine moieties were envisaged both to increase membrane stability and to exhibitinteractions with charged nucleic acids. Additionally, mannose and lactose triantennary clusters designedas multivalent ligands for selective interaction with lectin-type receptors were also efficiently synthesizedfor active cell/tissue targeting.