Issue Date: April 12, 2010
Nitroxyl Lights Up Copper Complex
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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