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Synthesis of Dual-Sensitive Core Cross-Linked Mixed Micelles through Thiol–Ene Addition and Subsequent Drug Release Behavior

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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… Click to show full abstract

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.

Keywords: core; ene addition; thiol ene; cross; release

Journal Title: Macromolecular Chemistry and Physics
Year Published: 2017

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