Discriminating formation of HNO from other reactive nitrogen oxide species

Donzelli, Sonia; Espey, Michael Graham; Thomas, Douglas D.; Mancardi, Daniele; Tocchetti, Carlo G.; Ridnour, Lisa A.; Paolocci, Nazareno; King, S. Bruce; Miranda, Katrina M.; Lazzarino, Giuseppe; Fukuto, Jon M.; Wink, David A.

doi:10.1016/j.freeradbiomed.2005.10.058

Cited by 103 publications

(113 citation statements)

References 82 publications

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“…We have previously shown that GS(O)NH 2 , formed from the association of HNO with GSH (Eq. 1), is a reproducible and selective marker for HNO [33].…”

Section: Resultsmentioning

confidence: 99%

“…Joseph Saavedra and Larry Keefer (Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick). Sulfinamide was synthesized as previously described [33,35]. Stock solutions of NO were prepared by sparging argon-deaerated 100 mM phosphate buffer (pH 7.4) with hydroxide scrubbed NO (>99%; Matheson, Montgomeryville, PA).…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

“…The reaction was terminated by removal of protein by centrifugal filtration (14,000 rpm for 30 min at 4°C, Microcon 3 kDa centrifugal filter device, Millipore). The deproteinized ultrafiltrate was injected directly onto a C-18 HPLC column to characterize the reaction products as previously described [33].…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

“…Production of HNO from oxidation of NH 2 OH and NOHA was evaluated with a recently developed, selective assay in which formation of sulfinamide (GS(O)NH 2 ) from the association of HNO with reduced glutathione (GSH) was quantified by HPLC [33]. The reaction of HNO with GSH was further investigated in real-time by both chemiluminescence and fluorometric assays.…”

Section: Introductionmentioning

confidence: 99%

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Generation of nitroxyl by heme protein-mediated peroxidation of hydroxylamine but not N-hydroxy-L-arginine

Donzelli

Espey

Flores-Santana

et al. 2008

Free Radical Biology and Medicine

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The chemical reactivity, toxicology and pharmacological responses to nitroxyl (HNO) are often distinctly different from those of nitric oxide (NO). The discovery that HNO donors may have pharmacological utility for treatment of cardiovascular disorders such as heart failure and ischemia reperfusion has led to increased speculation of potential endogenous pathways for HNO biosynthesis. Here, the ability of heme proteins to utilize H 2 O 2 to oxidize hydroxylamine (NH 2 OH) or N-hydroxy-L-arginine (NOHA) to HNO was examined. Formation of HNO was evaluated with a recently developed selective assay in which the reaction products in the presence of reduced glutathione (GSH) were quantified by HPLC. Release of HNO from the heme pocket was indicated by formation of sulfinamide (GS(O)NH 2 ), while the yields of nitrite and nitrate signified the degree of intramolecular recombination of HNO with the heme. Formation of GS(O)NH 2 was observed upon oxidation of NH 2 OH, whereas NOHA, the primary intermediate in oxidation of L-arginine by NO synthase, was apparently resistant to oxidation by the heme proteins utilized. In the presence of NH 2 OH, the highest yields of GS(O)NH 2 were observed with proteins in which the heme was coordinated to a histidine (horseradish peroxidase, lactoperoxidase, myeloperoxidase, myoglobin and hemoglobin) in contrast to a tyrosine (catalase) or cysteine (cytochrome P450). That peroxidation of NH 2 OH by horseradish peroxidase produced free HNO, which was able to affect intracellular targets, was verified by conversion of 4,5-diaminofluorescein to the corresponding fluorophore within intact cells.

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“…We have previously shown that GS(O)NH 2 , formed from the association of HNO with GSH (Eq. 1), is a reproducible and selective marker for HNO [33].…”

Section: Resultsmentioning

confidence: 99%

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Generation of nitroxyl by heme protein-mediated peroxidation of hydroxylamine but not N-hydroxy-L-arginine

Donzelli

Espey

Flores-Santana

et al. 2008

Free Radical Biology and Medicine

Self Cite

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“…15,16 A more selective strategy reported by Donzelli et al employed the rapid reaction of HNO with thiols as a marker of HNO generation in biological systems. 17 Treatment of HNO producing systems with glutathione resulted in the formation of a sulfinamide reaction product that was subsequently detected via HPLC. Another commonly employed strategy involves reaction of HNO with ferric heme-containing proteins such as metmyoglobin.…”

Section: Introductionmentioning

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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