Nitric oxide release from a cucurbituril encapsulated NO-donor

Abstract

Controlling S-nitrosothiol decomposition, with the consequent release of nitric oxide, is a topic of great research interest. The incorporation of nitrosomercaptopyridine (SNO⁺) into the cucurbit[7]uril cavity results in a large increase of its nitrosation equilibrium constant. This effect being a consequence of the preferential stabilization of organic cations by the formation of host : guest complexes with CB7 results in a drastic reduction of the SNO⁺ denitrosation rate constant. Moreover, SNO⁺ encapsulation also prevents its decomposition yielding disulfide and nitric oxide. The expulsion of SNO⁺ from the cucurbituril cavity through the application of a chemical stimulus (competitive binding) results in controlled nitric oxide release as was confirmed by using a NO selective electrode.