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Nitroxyl Lights Up Copper Complex

Copper-based fluorescent probe is a selective indicator for HNO in biological systems

by Celia Henry Arnaud
April 12, 2010 | A version of this story appeared in Volume 88, Issue 15

Nitric oxide might be the best known reactive nitrogen species relevant to biology, but it’s not the only one. Nitroxyl (HNO) is the reduced, protonated analog of NO and has several proposed physiological roles. But until now there hasn’t been a good way to detect HNO in biological systems. Stephen J. Lippard and Joel Rosenthal of Massachusetts Institute of Technology are reporting a copper-based fluorescent dye system that is selective for HNO (J. Am. Chem. Soc., DOI: 10.1021/ja909148v). The probe consists of a boron dipyrromethene (BODIPY) fluorescent dye connected to a copper(II) metal center. The copper’s ligand is made up of a tertiary nitrogen with two 2-pyridylmethyl substituents and a triazole substituent; the triazole serves as a bridge to the BODIPY group. This design minimizes the distance between the fluorescent reporter and the copper, ensuring the metal quenches the fluorescence in the system’s “off” state. When HNO is present, it reduces the copper, and the BODIPY group lights up. The researchers exposed the new complex to the nitroxyl anion donor Angeli’s salt (Na2N2O3), which generates HNO, and observed a rapid fourfold increase in fluorescence emission. The probe also responds to HNO in cell culture.


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