Synthesis of archaeal bipolar lipid analogues: a way to versatile drug/gene delivery systems.
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.
Brard
Mickaëlle
M
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.
Lainé
Céline
C
Réthoré
Gildas
G
Laurent
Isabelle
I
Neveu
Cécile
C
Lemiègre
Loïc
L
Benvegnu
Thierry
T
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
D008024:Ligands; D008055:Lipids; D009696:Nucleic Acids; D011956:Receptors, Cell Surface; D007785:Lactose; D008358:Mannose