Visualization of Nitroxyl in Living Cells by a Chelated Copper(II) Coumarin Complex

Zhou, Yi; Liu, Ke; Li, Juying; Yuan, Fang; Zhao, Tianchu; Yang, Cheng

doi:10.1021/ol103077q

Cited by 140 publications

(84 citation statements)

References 49 publications

(24 reference statements)

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“…Triazolylcoumarins, obtained from azidocoumarins by the Meldal-Sharpless reaction (catalytic analog of the Huisgen reaction, 1,3-dipolar cycloaddition of azides and alkynes), are used as fluorescent markers for marking biologically important molecules and nanoparticles [59][60][61][62][63][64][65][66].…”

Section: Functionalization and Modification Of The Coumarin Skeletonmentioning

confidence: 99%

Catalytic methods of creation and functionalization of the coumarin skeleton

Fedorov

Nyuchev

Beletskaya

2012

Chem Heterocycl Comp

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Section: Functionalization and Modification Of The Coumarin Skeletonmentioning

confidence: 99%

Catalytic methods of creation and functionalization of the coumarin skeleton

Fedorov

Nyuchev

Beletskaya

2012

Chem Heterocycl Comp

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“…6 This mechanism is further supported by electron paramagnetic resonance (EPR) studies of both CuBOT1 and CuCOT1, which reveal that the signal of the Cu(II) complex is abolished upon reaction with Angeli's salt under anaerobic conditions, confirming reduction to the diamagnetic ion Cu(I). 6,9 The selectivity of CuBOT1 and CuCOT1 toward HNO is similar. Both probes detect HNO selectively over NO and S-nitrosothiols such as S-nitroso cysteine (SNOC).…”

Section: Fluorescent Sensors Based On Copper Complexes Of Triazolyl(dmentioning

confidence: 89%

“…6,9 In the case of CuBOT1, cysteine An important conclusion that can be drawn from this mechanistic study is that, by increasing the basicity of the triazolyl fragment, it might be possible to enhance the rate of PCET. Amine-based ligands that are more basic than triazole might therefore provide sensors that are faster and more sensitive, and perhaps such a structural modification will help establish a kinetic preference for the oxidation of HNO over other biological reducing agents.…”

Section: Fluorescent Sensors Based On Copper Complexes Of Triazolyl(dmentioning

confidence: 91%

“…Ligand COT1 displays photophysical properties that are also suitable for live-cell optical microscopy. 9 In the metal-free state, COT1 displays an absorption maximum at λ abs = 400 nm Both CuBOT1 and CuCOT1 seem to detect HNO based on the same mechanism. The reaction between these Cu(II) complexes and HNO resembles the reversible interconversion of HNO and NO mediated by the enzyme superoxide dismutase 1 (SOD1).…”

Section: Fluorescent Sensors Based On Copper Complexes Of Triazolyl(dmentioning

confidence: 96%

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Metal-Based Optical Probes for Live Cell Imaging of Nitroxyl (HNO)

Rivera‐Fuentes

Lippard

2015

Acc. Chem. Res.

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Conspectus: Nitroxyl (HNO) is a biological signaling agent that displays distinctive reactivity compared to nitric oxide (NO). As a consequence, these two reactive nitrogen species trigger different physiological responses. Selective detection of HNO over NO has been a challenge for chemists, and several fluorogenic molecular probes have been recently developed with that goal in mind. Common constructs take advantage of the HNO-induced reduction of Cu(II) to Cu(I).The sensing mechanism of such probes relies on the ability of the unpaired electron in a d orbital of the Cu(II) center to quench the fluorescence of a photoemissive ligand by either an electron or energy transfer mechanism. Experimental and theoretical mechanistic studies suggest that proton-coupled electron transfer mediates this process, and careful tuning of the copper coordination environment has led to sensors with optimized selectivity and kinetics.The current optical probes cover the visible and near-infrared regions of the spectrum. This palette of sensors comprises structurally and functionally diverse fluorophores such as coumarin 2 (blue/green emission), boron dipyrromethane (BODIPY, green emission), benzoresorufin (red emission), and dihydroxanthenes (near-infrared emission). Many of these sensors have been successfully applied to detect HNO production in live cells. For example, copper-based optical probes have been used to detect HNO production in live mammalian cells that have been treated with H 2 S and various nitrosating agents. These studies have established a link between HSNO, the smallest S-nitrosothiol, and HNO. In addition, a near-infrared HNO sensor has been used to perform multicolor/multianalyte microscopy, revealing that exogenously applied HNO elevates the concentration of intracellular mobile zinc. This mobilization of zinc ions is presumably a consequence of nitrosation of cysteine residues in zinc-chelating proteins such as metallothionein.Future challenges for the optical imaging of HNO include devising probes that can detect HNO reversibly, especially because ratiometric imaging can only report equilibrium concentrations when the sensing event is reversible. Another important aspect that needs to be addressed is the creation of probes that can sense HNO in specific subcellular locations. These tools would be useful to identify the organelles in which HNO is produced in mammalian cells and probe the intracellular signaling networks in which this reactive nitrogen species is involved. In addition, near-infrared emitting probes might be applied to detect HNO in thicker specimens, such as acute tissue slices and even live animals, enabling the investigation of the roles of HNO in physiological or pathological conditions in multicellular systems.

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“…Nevertheless, few fluorescent probes for HNO detection were reported, and were mostly based on the reduction of Cu 2+ [10][11][12] . These fluorescent probes were susceptible to interferences from cellular reductants such as glutathione (GSH) and ascorbate.…”

Section: Liu Ping Et Al / Chinese Journal Of Analyticalmentioning

confidence: 99%