Interest in nitroxyl has recently been renewed due to its promise as an important pharmacological agent, especially in cardiovascular treatment. However, due to its instability, HNO must be generated from a donor molecule; a more stable molecule that decomposes under the appropriate conditions to yield HNO. Cycloadducts derived from N-hydroxyureas and an appropriate diene have been shown to release nitroxyl (HNO) upon undergoing a retro Diels-Alder reaction. Previous work has demonstrated dithienylethene photochromic molecules allow for the controlled release of a dienophile via a light-activated retro Diels-Alder reaction. Based on this work, we have developed a photochromic cylcoadduct that should release nitroxyl, via an acyl nitroso dienophile, upon irradiation with visible light. Such a controlled release mechanism should be beneficial in investigating the properties of nitroxyl.

Development of a photochromic drug delivery system: Storage and release of nitroxyl

249th National Meeting (2015)

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