Abstract
Phosphines react with nitroso compounds to yield a variety of products. Nitroxyl (HNO), the simplest nitroso compound, reacts with phosphines to give equal amounts of the corresponding phosphine oxide and azaylide. These azaylides react with a properly located internal electrophile through a reductive Staudinger ligation to yield stable and distinct HNO-derived products and release the corresponding alcohol. This chemistry serves as the basis of HNO detection by phosphine derivatives by incorporation of specific colorimetric or fluorometric leaving groups. Over the past few years, several distinct phosphines have been designed and prepared based on this chemistry to detect and quantify HNO. These organophosphines are highly suitable for HNO detection due to their rapid rate of HNO trapping and their lack of cross-reactivity with other physiologically relevant species, especially reducing agents. These fluorescent phosphine probes selectively detect HNO derived from various HNO donors in vitro and in living cells and form a distinct approach to HNO detection in live cells.
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