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

Maël Bathfield (1, 2) , Delphine Daviot (3) , Franck D’agosto (1) , Roger Spitz (1) , Catherine Ladavière (4) , Marie-Thérèse Charreyre (4) , Thierry Delair (4)

1 C2P2 - Laboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265
2 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
3 SMPH - Systèmes Macromoléculaires et Physiopathologie Humaine
4 IMP - Ingénierie des Matériaux Polymères

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 α-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).

Domaines: Polymères

Maël Bathfield, Delphine Daviot, Franck D’agosto, Roger Spitz, Catherine Ladavière, et al.. Synthesis of Lipid-α-End-Functionalized Chains by RAFT Polymerization. Stabilization of Lipid/Polymer Particle Assemblies. Macromolecules, 2008, 41 (22), pp.8346-8353. ⟨10.1021/ma801567c⟩. ⟨hal-02293454⟩