Utilizing Michael Addition Chemistry for the Synthesis of Drug Eluting Gauzes for Oral Wound Applications

Oral wounds are a debilitating side effect from many conditions including oral infections, dental and periodontal surgery, and oral mucositis caused by chemo and radiation therapy. These patients are often treated with corticosteroids to reduce inflammation. When applied as creams, topical steroids possess limited retention time, reducing therapeutic efficacy. This work investigates the potential for using Michael addition chemistry to create an oral drug eluting wound dressing. Michael addition of corticosteroid drugs to chitosan containing gauzes has the potential to offer tunable extended release of drug directly to the wound. The hydroxyl groups of the anesthetic eugenol and the steroid triamcinolone acetonide were each modified with an acrylate group via base catalyzed esterification with acryloyl chloride. Complete conversion was determined via FTIR and HPLC. The modified drug was conjugated with chitosan via surface modification in solution. Drug release profiles were generated for both synthesized gauze with known chitosan capacity and HemCon ChitoGauze Pro. Preliminary results indicate successful conjugation and release of eugenol and triamcinolone acetonide.