Synthesis of a trimannosylated-equipped archaeal diether lipid for the development of novel glycoliposomes

被引:13
作者
Barbeau, Julie [1 ,4 ]
Lemiegre, Lok [1 ,4 ]
Quelen, Allan [1 ,4 ]
Malard, Virginie [2 ]
Gao, Haifei [2 ]
Goncalves, Cristine [2 ]
Berchel, Mathieu [3 ,4 ]
Jaffres, Paul-Alain [3 ,4 ]
Pichon, Chantal [2 ]
Midoux, Patrick [2 ]
Benvegnu, Thierry [1 ,4 ]
机构
[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6226, 11 Allee Beaulieu,CS 50837, F-35708 Rennes 7, France
[2] Univ Orleans, CNRS, UPR 4301, Ctr Biophys Mol, Rue Charles Sadron,CS 80054, F-45071 Orleans, France
[3] Univ Brest, ScInBioS SFR148, CNRS, UMR 6521,CEMCA, Brest, France
[4] Univ Bretagne Loire, Rennes, France
关键词
Archaeal trimannosyl lipid; Liposomes; Dendritic cell binding; Mannose receptor; DELIVERY-SYSTEMS; DRUG-DELIVERY; RECOGNITION; RECEPTORS; ARCHAEOSOMES; VACCINE; CELLS;
D O I
10.1016/j.carres.2016.10.003
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An archaeal diether lipid possessing a tri-antenna of alpha-D-mannopyranoside linked via an oligoethylene spacer to a (2S)-2-(phytanyloxy)-3-(hexadecyloxy)propanoic acid backbone (TriMan-Diether) was designed and synthesized. This new mannosylated lipid inserted in liposomes would show both DC-targeting and adjuvant properties thanks to the TriMan structure and the diether tail part, respectively. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:142 / 148
页数:7
相关论文
共 31 条
[1]   Optimizing saccharide-directed molecular delivery to biological receptors:: Design, synthesis, and biological evaluation of glycodendrimer -: Cyclodextrin conjugates [J].
Benito, JM ;
Gömez-García, M ;
Mellet, CO ;
Baussanne, I ;
Defaye, J ;
Fernández, JMG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10355-10363
[2]   Archaeosomes based on novel synthetic tetraether-type lipids for the development of oral delivery systems [J].
Benvegnu, T ;
Réthoré, G ;
Brard, M ;
Richter, W ;
Plusquellec, D .
CHEMICAL COMMUNICATIONS, 2005, (44) :5536-5538
[3]   Archaeal lipids:: Innovative materials for biotechnological applications [J].
Benvegnu, Thierry ;
Lemiegre, Loic ;
Cammas-Marion, Sandrine .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (28) :4725-4744
[4]  
Benvegnu T, 2014, SPR CARB CH, V40, P341, DOI 10.1039/9781849739986-00341
[5]  
Benvegnu Thierry, 2009, Recent Pat Drug Deliv Formul, V3, P206
[6]   Modular Construction of Fluorescent Lipophosphoramidates by Click Chemistry [J].
Berchel, Mathieu ;
Haelters, Jean-Pierre ;
Couthon-Gourves, Helene ;
Deschamps, Laure ;
Midoux, Patrick ;
Lehn, Pierre ;
Jaffres, Paul-Alain .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) :6294-6303
[7]   THE PREFERRED CONFORMATION OF OLIGOSACCHARIDES DERIVED FROM THE COMPLEX-TYPE CARBOHYDRATE PORTIONS OF GLYCOPROTEINS [J].
BOCK, K ;
ARNARP, J ;
LONNGREN, J .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1982, 129 (01) :171-178
[8]   Synthesis of archaeal bipolar lipid analogues:: A way to versatile Drug/Gene delivery systems [J].
Brard, Mickaelle ;
Laine, Celine ;
Rethore, Gildas ;
Laurent, Isabelle ;
Neveu, Cecile ;
Lemiegre, Loic ;
Benvegnu, Thierry .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8267-8279
[9]   Influence of Ligand Valency on the Targeting of Immature Human Dendritic Cells by Mannosylated Liposomes [J].
Espuelas, Socorro ;
Thumann, Christine ;
Heurtault, Beatrice ;
Schuber, Francis ;
Frisch, Benoit .
BIOCONJUGATE CHEMISTRY, 2008, 19 (12) :2385-2393
[10]   Interest of glycolipids in drug delivery: from physicochemical properties to drug targeting [J].
Faivre, Vincent ;
Rosilio, Veronique .
EXPERT OPINION ON DRUG DELIVERY, 2010, 7 (09) :1031-1048