Synthesis and Evaluation of Novel Functional Polymers Derived from Renewable Jasmine Lactone for Stimuli‐Responsive Drug Delivery
Kuldeep K. Bansal, Ezgi Özliseli, Ari Rosling, Jessica M. Rosenholm
Abstract
Abstract Instances of synthetic polymers obtained from renewable feedstock with the possibility of post‐synthesis functionalization are scarce. Herein, the first ever synthesis and drug delivery application of amphiphilic block copolymer (mPEG‐b‐PJL) derived from renewable jasmine lactone with free allyl groups on the backbone is presented. The polymer is synthesized via facile ring‐opening polymerization and subsequently, UV mediated thiol‐ene click chemistry is utilized for post‐functionalization. The introduction of hydroxyl, carboxyl, and amine functionality to mPEG‐b‐PJL polymer is successfully established. As a proof‐of‐concept demonstration, doxorubicin (DOX) is conjugated on hydroxyl‐terminated polymer (mPEG‐b‐PJL‐OH) via redox responsive disulfide linkage to obtain PJL‐DOX. PJL‐DOX is readily self‐assembled into micelles with an average hydrodynamic size of ≈ 150 nm and demonstrates reduction‐responsive DOX release. Micelles are evaluated in vitro for cytocompatibility and selective drug release in cancer cells (MDA‐MB‐231) using 10 m m glutathione as a reducing agent. Cytotoxicity and microscopy results confirm a redox‐triggered release of DOX, which is further confirmed by flow cytometry. The introduction of these novel functional polymers can pave the way forward in designing polymer‐drug conjugate‐based smart nano‐carriers.