Medical adhesives have the potential to eliminate the need for unpleasant mechanical fixations such as sutures, staples, and screws, but face challenges to widespread implementation due to brittleness and cytotoxicity. To overcome these limitations, we designed therapeutic methacrylic (TMA) monomers that impart tunable mechanical properties, decreased formaldehyde release, and covalently-controlled bioactivity to commercial medical adhesives. Small molecule therapeutics including NSAIDs, analgesics, and other cell-instructive compounds have been covalently tethered to the carbonyl of methacrylate using bonds of varying stability to hydrolysis. The resulting TMA monomers are compatible with both cyanoacrylate-based (skin) and methacrylate-based (bone) medical adhesives, co-polymerizing with these adhesives on contact with tissue to form polymers with enhanced adhesive properties. For example, when an anhydride-tether TMA was incorporated into 3M's Vetbond<sup>TM</sup>, a butyl cyanoacrylate (BCA) skin adhesive, the resulting TMA–BCA material delivered therapeutic on the same order of magnitude and time scale as topical medications, where ester- and amide-tether TMA-BCA adhesives could sustain delivery of a lower dose of therapeutic over several weeks. In addition to the hydrolysis-driven controlled release, TMA adhesives also inherit new mechanical properties based on the structure of their therapeutic payloads, enabling specific functionality to be programmed directly into the polymer backbone of adhesives. For example, TMA materials carrying therapeutics capable of hydrogen bonding created stiffer and tougher (less brittle) adhesives, while those carrying bulky therapeutics with flexible segments created adhesives that recapitulate the softness of skin. Overall, TMAs represent a platform technology that can be used to build adaptable, bioactive adhesives through principles of molecular design and polymer chemistry.

Hydrolysis-driven controlled drug delivery and tunable adhesive properties via novel therapeutic methacrylic monomers

255th National Meeting (2018)

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