Donors of HNO

Miranda, Katrina M.; Nagasawa, Hiromichi; Toscano, John P.

doi:10.2174/1568026054679290

Cited by 84 publications

(99 citation statements)

References 131 publications

(216 reference statements)

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“…1 (84,89) The two most commonly used donors of HNO are Angeli's salt (sodium trioxodinitrate, Na 2 N 2 O 3 ) and derivatives of sulfohydroxamic acid, particularly Piloty's acid (benzenesulfohydroxamic acid, C 6 H 5 SO 2 NHOH). Several clinically used compounds such as cyanamide and hydroxyurea can also be bioactivated to HNO [for reviews on HNO donors, see (70,79,80,110)]. …”

Section: Donors Of Hnomentioning

confidence: 99%

“…Such reactions have often been invoked as the basis for the vasoactive properties of HNO donors. In fact, detection of NO in the presence of oxidants, particularly ferricyanide, has long been used as an indirect indicator of HNO production (110). Two-electron oxidants such as flavin adenine dinucleotide (FAD) can also oxidize HNO to NO (52).…”

Section: Hno Reactivitymentioning

confidence: 99%

See 1 more Smart Citation

The Specificity of Nitroxyl Chemistry Is Unique Among Nitrogen Oxides in Biological Systems

Flores-Santana

Salmon

Donzelli

et al. 2011

Antioxidants & Redox Signaling

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The importance of nitric oxide in mammalian physiology has been known for nearly 30 years. Similar attention for other nitrogen oxides such as nitroxyl (HNO) has been more recent. While there has been speculation as to the biosynthesis of HNO, its pharmacological benefits have been demonstrated in several pathophysiological settings such as cardiovascular disorders, cancer, and alcoholism. The chemical biology of HNO has been identified as related to, but unique from, that of its redox congener nitric oxide. A summary of these findings as well as a discussion of possible endogenous sources of HNO is presented in this review.

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Section: Donors Of Hnomentioning

confidence: 99%

Section: Hno Reactivitymentioning

confidence: 99%

The Specificity of Nitroxyl Chemistry Is Unique Among Nitrogen Oxides in Biological Systems

Flores-Santana

Salmon

Donzelli

et al. 2011

Antioxidants & Redox Signaling

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“…28 For the experimental conditions employed herein (25 °C, pH 7.4, 10 −4 DTPA, aerobic), k 1 was calculated at 8.1 × 10 −4 s −1 . After determination of k on via Angeli's salt calibration, the observed rates of Mn II (NO)TPPS formation were used to calculate HNO concentrations according to: (8) where [Mn II (NO)TPPS] and [Mn III TPPS] concentrations in the film were monitored spectroscopically at 432 and 467 nm, respectively. Considering xerogel film thicknesses (~29 µm) as the optical path length, the extinction coefficient of Mn III TPPS encapsulated in AEMP/MTMOS was calculated to be 90000 M −1 cm −1 at 467 nm via Beer's law.…”

Section: Kinetic Hno Quantificationmentioning

confidence: 99%

Xerogel Optical Sensor Films for Quantitative Detection of Nitroxyl

2008

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Xerogel films were synthesized via sol-gel chemistry to fabricate optical nitroxyl (HNO) sensors. Selective detection of HNO in solution was achieved by monitoring the rates of manganese(III) meso-tetrakis(4-sulfonatophenyl) porphyrinate (Mn III TPPS) reductive nitrosylation in the anaerobic interior of aminoalkoxysilane-derived xerogel films. Nitroxyl permeability in sensor films deposited in round-bottom 96-well plates was enhanced via incorporation of trimethoxysilylterminated poly(amidoamine-organosilicon) (PAMAMOS) dendrimers in the xerogel network. The selectivity of Mn III TPPS for HNO, the overall sensitivity, and the working dynamic range of the resulting sensors were characterized. The HNO-sensing microtitre plates were used to quantify pH-dependent HNO generation by the recently described HNO-donor sodium-1-(isopropylamino)diazene-1-ium-1,2-diolate (IPA/NO), and compare HNO-production efficiency between IPA/NO and Angeli's salt, a traditional HNO-donor.

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“…Although the direct observation of endogenously produced HNO in mammalian cells has remained elusive, CuBOT1 was also used to investigate the generation of HNO from the S-nitrosothiol GSNO and H 2 S. 17 Human umbilical vein endothelial cells (HUVECs) were incubated with 10 µM CuBOT1 In related work, Ivanović-Burmazović and co-workers showed that sodium nitroprusside (Na 2 [Fe(CN) 5 (NO)]; SNP) reacts in live cells to produce HNO. 18 In this study, the authors employed CuBOT1-loaded HUVECs to show that treatment of these cells with either SNP or H 2 S alone did not elicit a significant fluorescence turn-on.…”

Section: Biological Applications Of Cubot1mentioning

confidence: 99%

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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Donors of HNO

Cited by 84 publications

References 131 publications

The Specificity of Nitroxyl Chemistry Is Unique Among Nitrogen Oxides in Biological Systems

The Specificity of Nitroxyl Chemistry Is Unique Among Nitrogen Oxides in Biological Systems

Xerogel Optical Sensor Films for Quantitative Detection of Nitroxyl

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

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