Poly(ε-caprolactone)s (PCL)s are among the most used aliphatic polyesters for biomedical application due to their biodegradability, biocompatibility, and synthetic versatility. The properties of this synthetic polymer can be easily tuned by introducing different functionalities. However, the difficulty in polymerizing functionalized ε-caprolactone (CL) monomers limits further applications. A significant issue is the involvement of these functionalities in the polymerization process, which results in unwanted side reactions. Herein, we utilized post-polymerization reactions as an alternative to introducing redox responsive lipoic acid to the side chain of PCL. We developed an ether-linked γ-propargyl substituted PCL as the hydrophobic block of an amphiphilic diblock copolymer (AmDC). The propargyl group was used to couple the lipoic acid via click chemistry. The hydrophilic block is composed of an ether-linked, thermoresponsive γ-tri(ethylene glycol) substituted PCL. The final AmDC can self-assemble in an aqueous solution to form polymeric micelles with a lipoic acid-functionalized hydrophobic core, and tri(ethylene glycol) functionalized hydrophilic shell. These polymeric micelles can be used as a drug delivery system for delivering the anticancer drug doxorubicin. The tri(ethylene glycol) containing hydrophilic shell is used to enhance the solubility of micelles, their circulation in the bloodstream, and thermoresponsive properties for triggering drug release. At the same time, the lipoic acid containing a hydrophobic core can undergo reversible cross-linking to enhance the micelle's stability and prevent premature drug leakage.

Design and synthesis of <i>γ</i>-functionalized poly(ε-caprolactone)s grafted with lipoic acid

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Design and synthesis of γ-functionalized poly(ε-caprolactone)s grafted with lipoic acid