title: Synthesis of archaeal bipolar lipid analogues: a way to versatile drug/gene delivery systems.
abstract: A synthetic route for the preparation of symmetrical and unsymmetrical archaeal tetraether-like analogues has been described. The syntheses are based upon the elaboration of hemimacrocyclic tetraether lipid cores from versatile building blocks followed by simultaneous or sequential introduction of polar head groups. Functionalizations of the tetraether lipids with neutral lactose or phosphatidylcholine polar heads and cationic glycine betaine moieties were envisaged both to increase membrane stability and to exhibit interactions with charged nucleic acids. Additionally, mannose and lactose triantennary clusters designed as multivalent ligands for selective interaction with lectin-type receptors were also efficiently synthesized for active cell/tissue targeting.
authors.affiliation: UMR CNRS 6226 Sciences Chimiques de Rennes, Equipe Chimie Organique et Supramoléculaire, Ecole Nationale Supérieure de Chimie de Rennes, Av. Général Leclerc, 35700 Rennes, France.
authors.forename: Mickaëlle
authors.initials: M
authors.lastname: Brard
authors.forename: Céline
authors.initials: C
authors.lastname: Lainé
authors.forename: Gildas
authors.initials: G
authors.lastname: Réthoré
authors.forename: Isabelle
authors.initials: I
authors.lastname: Laurent
authors.forename: Cécile
authors.initials: C
authors.lastname: Neveu
authors.forename: Loïc
authors.initials: L
authors.lastname: Lemiègre
authors.forename: Thierry
authors.initials: T
authors.lastname: Benvegnu
mesh_terms: D001105:Archaea / Q000737:chemistry* / Q000235:genetics; D045744:Cell Line, Tumor; D016503:Drug Delivery Systems / Q000379:methods; D018014:Gene Transfer Techniques; D006801:Humans; D007785:Lactose / Q000737:chemistry; D008024:Ligands; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008358:Mannose / Q000737:chemistry; D008968:Molecular Conformation; D009696:Nucleic Acids / Q000737:chemistry; D011956:Receptors, Cell Surface / Q000737:chemistry / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D008024:Ligands; D008055:Lipids; D009696:Nucleic Acids; D011956:Receptors, Cell Surface; D007785:Lactose; D008358:Mannose