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Synthesis of Dual‐Sensitive Core Cross‐Linked Mixed Micelles through Thiol–Ene Addition and Subsequent Drug Release Behavior
Author(s) -
Hespel Louise,
Asmar Arlette El,
Morandi Gaëlle,
Lecamp Laurence,
Picton Luc,
Burel Fabrice
Publication year - 2017
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201700016
Subject(s) - micelle , chemistry , polymer chemistry , thiol , acrylic acid , copolymer , lower critical solution temperature , aqueous solution , organic chemistry , polymer
Herein the synthesis of core cross‐linked (CCL) mixed micelles through a UV‐promoted thiol–ene addition onto lipid core unsaturations and the subsequent release of an encapsulated drug depending on the external conditions (pH/temperature) are reported. The thiol–ene addition proceeds even in the absence of a photoinitiator to reach a complete conversion in a few minutes in bulk. The cross‐linking reaction is applied in aqueous media onto lipid‐ b ‐poly(acrylic acid) (lipid‐ b ‐PAA) only and then a mixture of pH‐sensitive lipid‐ b ‐PAA and thermo‐sensitive lipid‐ block ‐poly(2‐isopropyl‐2‐oxazoline) copolymers. Structurally CCL micelles, preserved in any conditions, with a stimuli‐sensitive corona whose swelling depends on the external pH or/and temperature, are successfully prepared. The release of vitamin K1 (VK1) is then investigated from all the previous systems and demonstrates a strong dependency to the external conditions. Indeed, the dual‐sensitive CCL micelles release VK1 only when two triggers (pH 10 and T = 38 °C) are simultaneously activated.