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

• DOI: 10.1021/jo071181r
• Publication Date: 2007-10-03T13:49:57Z
• Authors: Mickaëlle Brard; Céline Lainé,; Gildas Réthoré,; Isabelle Laurent; Cécile Neveu; Loïc Lemiègre; Thierry Benvegnu
• Keywords: Cationic polymerization; Betaine

A synthetic route for the preparation of symmetrical and unsymmetrical archaeal tetraether-like analogues has been described. The syntheses are based upon elaboration hemimacrocyclic tetraether lipid cores from versatile building blocks followed by simultaneous or sequential introduction polar head groups. Functionalizations lipids with neutral lactose phosphatidylcholine heads cationic glycine betaine moieties were envisaged both to increase membrane stability exhibit interactions charged nucleic acids. Additionally, mannose triantennary clusters designed as multivalent ligands selective interaction lectin-type receptors also efficiently synthesized active cell/tissue targeting.