Synthesis of Lipid-α-End-Functionalized Chains by RAFT Polymerization. Stabilization of Lipid/Polymer Particle Assemblies

被引:34
作者
Bathfield, Mael [1 ,2 ]
Daviot, Delphine [2 ]
D'Agosto, Franck [1 ]
Spitz, Roger [1 ]
Ladaviere, Catherine [2 ]
Charreyre, Marie-Therese [2 ]
Delair, Thierry [2 ]
机构
[1] Univ Lyon 1, Univ Lyon, CPE Lyon,CNRS UMR 5265,LCPP Team, Lab Chim Catalyse Polymeres & Procedes C2P2, F-69616 Villeurbanne, France
[2] Ecole Normale Super Lyon, Unite Mixte CNRS BioMerieux, F-69364 Lyon, France
关键词
D O I
10.1021/ma801567c
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A functional dithioester including a phospholipid moiety (Lipid-DT) has been synthesized in a high yield (71% after purification) from a precursor chain transfer agent (CTA) and fully characterized. The RAFT polymerization of an acrylamide derivative, N-acryloylmorpholine (NAM), mediated by this Lipid-DT exhibits a prolonged induction period in comparison with a nonfunctional dithioester. This phenomenon is discussed in terms of steric shielding induced by the bulky lipid moiety of the CTA. Moreover, the lipid moiety located at the a-end of the chains has a strong influence on the size exclusion chromatography analyses in THF using a standard-based calibration, with the suspicion of a retention phenomenon. The well-defined structure of the lipid-end-functionalized polymer chains has been evidenced by MALDI-TOF mass spectrometry. Finally, these chains have been successfully incorporated into lipid/polymer particle assemblies (LipoParticles) that resulted in an improved stabilization in aqueous medium at relatively high ionic strength (300 mM).
引用
收藏
页码:8346 / 8353
页数:8
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