Our research team has evaluated oxazines that are capable of triggered release of nitroxyl (HNO) and other small molecules in response to either thermal or mechanical impetus. Specifically, We demonstrate concomitant release of HNO and small molecule organics from amphiphilic poly(norbornene)-based copolymers. This key function was achieved by incorporation of thermally-labile oxazine units within random and block copolymer architectures. Upon thermolysis, we observed generation of HNO and release of a small molecule conjugate. Importantly, the release kinetics of HNO and a UV-active small molecule reporter were found to be 1:1, signifying an ability to monitor HNO production indirectly or to simultaneously release organic therapeutics with HNO. We also observed mechanochemical triggering of oxazine moieties contained within polymer main chains and bridging crosslink segments, which were accessed by modifying the sites of attachment within the polymer-oxazine conjugate.

Polymers for thermal and mechanochemical release of nitroxyl (HNO) and other small molecule payloads

253rd National Meeting (2017)

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