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The Physiological Chemistry And Biological Activity Of Nitroxyl (HNO): The Neglected, Misunderstood, And Enigmatic Nitrogen Oxide.

J. Fukuto, M. D. Bartberger, A. Dutton, N. Paolocci, D. Wink, K. Houk
Published 2005 · Chemistry, Medicine

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10.1021/JA00749A003
Ab initio molecular orbital study of the hydrogen, lithium, and fluorine derivatives of nitric oxide
J. Peslak (1971)
10.1016/J.BBRC.2004.01.081
Xanthine oxidase converts nitric oxide to nitroxyl that inactivates the enzyme.
M. Saleem (2004)
10.1016/B978-012370420-7/50042-3
Role of Nitric Oxide in Myocardial Ischemia-Reperfusion Injury
J. Vinten-Johansen (2000)
10.1073/PNAS.96.25.14617
Opposite effects of nitric oxide and nitroxyl on postischemic myocardial injury.
X. Ma (1999)
10.1006/BBRC.1994.1668
Bioassay discrimination between nitric oxide (NO.) and nitroxyl (NO-) using L-cysteine.
R. Pino (1994)
10.1016/S0891-5849(03)00111-4
The mode of decomposition of Angeli's salt (Na2N2O3) and the effects thereon of oxygen, nitrite, superoxide dismutase, and glutathione.
S. Liochev (2003)
10.1016/S0891-5849(01)00480-4
Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple.
F. Q. Schafer (2001)
10.1074/JBC.M006174200
Unique Oxidative Mechanisms for the Reactive Nitrogen Oxide Species, Nitroxyl Anion*
K. Miranda (2001)
10.1152/ajpregu.1999.276.1.R259
Ca2+-induced Ca2+ release involved in positive inotropic effect mediated by CGRP in ventricular myocytes.
Ming-He Huang (1999)
10.1021/JA0376184
Efficient trapping of HNO by deoxymyoglobin.
Filip Sulc (2004)
10.1021/JA990318V
Decomposition of Sodium Trioxodinitrate (Angeli's Salt) To Hydroxyl Radical: An ESR Spin-Trapping Study
D. Stoyanovsky (1999)
10.1080/10715760410001659764
Angeli's Salt and Spinal Motor Neuron Injury
A. Väänänen (2004)
10.1016/0304-4165(94)00181-V
Direct measurement of the accumulation and mitochondrial conversion of nitric oxide within Chinese hamster ovary cells using an intracellular electron paramagnetic resonance technique.
R. Clarkson (1995)
10.1038/327524A0
Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor
R. M. Palmer (1987)
10.1021/JA034378J
Spin-forbidden deprotonation of aqueous nitroxyl (HNO).
V. Shafirovich (2003)
10.1021/JA00210A047
Oxidation and reduction of hemoproteins by trioxodinitrate(II). The role of nitrosyl hydride and nitrite
M. Doyle (1988)
10.1146/ANNUREV.PH.57.030195.003423
Nitric oxide synthases: properties and catalytic mechanism.
O. Griffith (1995)
10.1006/BBRC.1995.2076
Cytochrome c oxidase catalysis of the reduction of nitric oxide to nitrous oxide.
X. Zhao (1995)
10.1016/S0003-9861(03)00335-7
Oxidation of N-hydroxyguanidines by copper(II): model systems for elucidating the physiological chemistry of the nitric oxide biosynthetic intermediate N-hydroxyl-L-arginine.
J. Cho (2003)
10.1021/TX010102I
Mechanisms of nitrogen oxide-mediated disruption of metalloprotein function: an examination of the copper-responsive yeast transcription factor Ace1.
M. Shinyashiki (2001)
10.1042/BJ3320009
Reactions of nitric oxide with mitochondrial cytochrome c: a novel mechanism for the formation of nitroxyl anion and peroxynitrite.
M. Sharpe (1998)
10.1073/pnas.1031571100
Nitroxyl gets to the heart of the matter
M. Feelisch (2003)
10.1139/V73-166
Pulse Radiolysis of Nitric Oxide in Aqueous Solution
W. Seddon (1970)
10.1016/0301-0104(95)00092-3
A theoretical analysis of the lowest excited states in HNO/NOH and HPO/POH
A. Luna (1995)
10.1016/0014-2999(95)00046-N
Increase in serum NG-hydroxy-L-arginine in rats treated with bacterial lipopolysaccharide.
M. Hecker (1995)
10.1021/JP992511H
Direct Observation of Spin Forbidden Proton-Transfer Reactions: 3NO-+ HA →1HNO + A-
G. Janaway (2000)
10.1073/PNAS.88.23.10860
Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase.
M. E. Murphy (1991)
10.1006/NIOX.1998.0166
The reaction of nitroxyl (HNO) with nitrosobenzene gives cupferron (N-nitrosophenylhydroxylamine).
D. Shoeman (1998)
10.1080/02603598808072309
The Aqueous Solution Chemistry of Nitrogen in Low Positive Oxidation States
F. T. Bonner (1988)
10.1016/S0891-5849(01)00477-4
Nitroxyl oxidizes NADPH in a superoxide dismutase inhibitable manner.
A. Reif (2001)
10.1021/JM00174A001
Evidence for nitroxyl in the catalase-mediated bioactivation of the alcohol deterrent agent cyanamide.
H. Nagasawa (1990)
10.1016/S0896-6273(00)80859-4
Attenuation of NMDA Receptor Activity and Neurotoxicity by Nitroxyl Anion, NO−
W. Kim (1999)
10.1073/pnas.041481598
On the acidity and reactivity of HNO in aqueous solution and biological systems
M. D. Bartberger (2001)
10.1088/0022-3700/8/7/021
Resonant vibrational excitation of the NO ground state by electron impact in the 0.1-3 eV energy range
M. Tronc (1975)
10.1016/S0891-5849(98)00277-9
The reaction of nitric oxide with ubiquinol: kinetic properties and biological significance.
J. Poderoso (1999)
10.1088/0022-3700/19/23/020
Low-energy electron scattering by the NO molecule
J. Tennyson (1986)
10.1016/S0891-5849(02)01179-6
Nitroxyl affords thiol-sensitive myocardial protective effects akin to early preconditioning.
P. Pagliaro (2003)
10.1021/IC00236A004
Photolysis of the nitrogen-nitrogen double bond in trioxodinitrate: reaction between triplet oxonitrate(1-) and molecular oxygen to form peroxonitrite
C. E. Donald (1986)
10.1016/S0003-9861(02)00031-0
Further evidence for distinct reactive intermediates from nitroxyl and peroxynitrite: effects of buffer composition on the chemistry of Angeli's salt and synthetic peroxynitrite.
K. Miranda (2002)
10.1016/S0891-5849(98)00327-X
Induction of DNA strand breakage and base oxidation by nitroxyl anion through hydroxyl radical production.
H. Ohshima (1999)
10.1016/0006-2952(95)02098-5
Oxidation of N-hydroxyguanidine by nitric oxide and the possible generation of vasoactive species.
J. Yoo (1995)
10.1016/S0165-6147(97)01137-1
Soluble guanylate cyclase: the forgotten sibling.
A. Hobbs (1997)
10.1016/S0006-2952(98)00080-X
Mechanisms of inhibition of aldehyde dehydrogenase by nitroxyl, the active metabolite of the alcohol deterrent agent cyanamide.
E. Demaster (1998)
10.1016/S0741-8329(99)00056-7
Reaction of nitroxyl, an aldehyde dehydrogenase inhibitor, with N-acetyl-L-cysteine.
D. Shoeman (2000)
10.1016/S0022-0728(68)80144-5
Electrochemistry of nitric oxide and of nitrous acid at a mercury electrode
D. Ehman (1968)
10.1021/JP037996V
Solvent and structural effects in the N-H bond homolytic dissociation energy
José R. B. Gomes (2004)
10.1021/BI9813936
Reactions catalyzed by tetrahydrobiopterin-free nitric oxide synthase.
Kristin M. Rusche (1998)
10.1006/ABBI.1997.0565
The cytotoxicity of nitroxyl: possible implications for the pathophysiological role of NO.
D. Wink (1998)
10.1073/PNAS.93.25.14492
No .NO from NO synthase.
H. Schmidt (1996)
10.1016/S0165-6147(00)01555-8
The molecular pharmacology of CGRP and related peptide receptor subtypes.
C. Juaneda (2000)
10.1146/ANNUREV.PHARMTOX.42.092501.104328
The biochemistry and physiology of S-nitrosothiols.
N. Hogg (2002)
10.1016/S0898-8838(08)60194-4
Reduction potentials involving inorganic free radicals in aqueous solution
D. Stanbury (1989)
10.1007/0-306-46806-9_10
The Chemical Biology of Nitric Oxide
D. Wink (2002)
10.1006/ABBI.1995.1231
NO+, NO, and NO- donation by S-nitrosothiols: implications for regulation of physiological functions by S-nitrosylation and acceleration of disulfide formation.
D. Arnelle (1995)
10.1016/0006-2952(92)90584-6
Chemical oxidation of N-hydroxyguanidine compounds. Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation.
J. Fukuto (1992)
10.1016/S0003-9861(02)00074-7
Nitroxyl (NO-): a substrate for superoxide dismutase.
S. Liochev (2002)
10.1074/JBC.M108079200
Formation of Peroxynitrite from Reaction of Nitroxyl Anion with Molecular Oxygen*
M. Kirsch (2002)
10.1021/JA036370F
Fast nitroxyl trapping by ferric porphyrins.
S. Bari (2003)
NEW NO DIECTIONS
E. Wilson (2004)
10.1006/BBRC.1993.2307
Conversion of nitroxyl (HNO) to nitric oxide (NO) in biological systems: the role of physiological oxidants and relevance to the biological activity of HNO.
J. Fukuto (1993)
Nitric oxide : biology and pathobiology
L. Ignarro (2000)
10.1021/JA038042L
Hyponitrite radical, a stable adduct of nitric oxide and nitroxyl.
G. A. Poskrebyshev (2004)
10.1152/AJPHEART.1996.271.5.H1988
Arginase activity in endothelial cells: inhibition by NG-hydroxy-L-arginine during high-output NO production.
G. Buga (1996)
10.1016/S0003-9861(02)00656-2
Nitroxyl-mediated disruption of thiol proteins: inhibition of the yeast transcription factor Ace1.
N. M. Cook (2003)
10.1002/CHIN.197521002
SELF-CONSISTENT FIELD CALCULATION OF NITROSYL HYDRIDE AND NITROGEN HYDROXIDE
G. A. Gallup (1975)
The pharmacological activity of nitroxyl: a potent vasodilator with activity similar to nitric oxide and/or endothelium-derived relaxing factor.
J. Fukuto (1992)
10.1073/pnas.181191198
Nitroxyl anion exerts redox-sensitive positive cardiac inotropy in vivo by calcitonin gene-related peptide signaling
N. Paolocci (2001)
10.1074/jbc.M104237200
Copper,Zinc Superoxide Dismutase as a Univalent NO−Oxidoreductase and as a Dichlorofluorescin Peroxidase*
S. Liochev (2001)
10.1074/jbc.M004337200
Arginine Conversion to Nitroxide by Tetrahydrobiopterin-free Neuronal Nitric-oxide Synthase
S. Adak (2000)
10.1016/J.JINORGBIO.2004.11.005
Coordination chemistry of the HNO ligand with hemes and synthetic coordination complexes.
P. Farmer (2005)
10.1021/BI973153G
Reaction between S-nitrosothiols and thiols: generation of nitroxyl (HNO) and subsequent chemistry.
P. Wong (1998)
10.1021/JM00098A008
Prodrugs of nitroxyl as inhibitors of aldehyde dehydrogenase.
M. J. Lee (1992)
10.1074/jbc.M305544200
Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate
Juliana Ivanova (2003)
10.1046/j.1471-4159.2001.00509.x
Nitroxyl anion regulation of the NMDA receptor
C. Colton (2001)
10.1016/S0076-6879(96)68004-5
Say NO to nitric oxide: nomenclature for nitrogen- and oxygen-containing compounds.
W. Koppenol (1996)
10.1073/pnas.162095599
The reduction potential of nitric oxide (NO) and its importance to NO biochemistry
M. D. Bartberger (2002)
10.1073/pnas.1430507100
A biochemical rationale for the discrete behavior of nitroxyl and nitric oxide in the cardiovascular system
K. Miranda (2003)
10.1073/pnas.0937302100
Positive inotropic and lusitropic effects of HNO/NO− in failing hearts: Independence from β-adrenergic signaling
N. Paolocci (2003)
10.1021/JA994079N
The HNO Adduct of Myoglobin: Synthesis and Characterization
Rong Lin and (2000)
10.1021/JA00888A004
The Decomposition of Hyponitrous Acid. I. The Non-chain Reaction
J. R. Buchholz (1963)
10.1021/IC00219A017
Evidence from the reaction between trioxodinitrate(II) and nitrogen-15-labeled nitric oxide that trioxodinitrate(II) decomposes into nitrosyl hydride and nitrite in neutral aqueous solution
D. Bazylinski (1985)
10.1016/S0891-5849(98)00256-1
Exposure of Mn and FeSODs, but not Cu/ZnSOD, to NO leads to nitrosonium and nitroxyl ions generation which cause enzyme modification and inactivation: an in vitro study.
V. Niketić (1999)
10.1073/pnas.112202099
Nitroxyl and its anion in aqueous solutions: Spin states, protic equilibria, and reactivities toward oxygen and nitric oxide
V. Shafirovich (2002)



This paper is referenced by
10.1089/ars.2010.3327
Nitroxyl (HNO) as a vasoprotective signaling molecule.
Michelle L. Bullen (2011)
Redox variants of NO ( NO and HNO ) elicit vasorelaxation of resistance arteries via distinct mechanisms
J. Favaloro (2009)
10.1021/ja909148v
Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex.
Joel Rosenthal (2010)
10.1016/J.NIOX.2007.06.005
Reduction and S-nitrosation of the neuropeptide oxytocin: implications for its biological function.
Jean-François Roy (2007)
10.1152/ajpheart.00008.2009
Redox variants of NO (NO{middle dot} and HNO) elicit vasorelaxation of resistance arteries via distinct mechanisms.
J. Favaloro (2009)
Etude du mécanisme d’activation de l’oxygène par les NO-Synthases
A. Brunel (2012)
10.1039/c4cc00980k
A fast-response, highly sensitive and selective fluorescent probe for the ratiometric imaging of nitroxyl in living cells.
C. Liu (2014)
10.1016/j.freeradbiomed.2016.05.013
The chemical biology of protein hydropersulfides: Studies of a possible protective function of biological hydropersulfide generation.
R. Millikin (2016)
10.1002/POC.1871
Detection of nitroxyl (HNO) by a prefluorescent probe
Meredith R. Cline (2011)
10.1016/j.vph.2015.03.004
Gender specific generation of nitroxyl (HNO) from rat endothelium.
K. Hamilton (2015)
10.1016/j.niox.2010.12.004
Photocontrollable nitric oxide (NO) and nitroxyl (HNO) donors and their release mechanisms.
H. Nakagawa (2011)
10.1021/acs.inorgchem.5b01252
Solution Dynamics of Redox Noninnocent Nitrosoarene Ligands: Mapping the Electronic Criteria for the Formation of Persistent Metal-Coordinated Nitroxide Radicals.
Brandon R. Barnett (2015)
10.1016/B978-0-12-800934-5.00013-X
Detection of HNO by Membrane Inlet Mass Spectrometry
T. A. Chavez (2017)
10.1039/B713377B
Generation, basic chemistry, and detection of N-nitrosotryptophan derivatives.
M. Kirsch (2007)
10.1016/J.PHARMTHERA.2006.11.002
The pharmacology of nitroxyl (HNO) and its therapeutic potential: not just the Janus face of NO.
N. Paolocci (2007)
MECHANISTIC STUDIES ON THE REACTIONS OF VITAMIN B12 COMPLEXES WITH THE NITROXYL (HNO) DONORS ANGELI'S SALT AND PILOTY'S ACID
Harishchandra Subedi (2014)
10.1016/j.ica.2020.119567
Unusual monodentate binding of a C-NONOate ligand in the nitrosyl complex (OEP)Ru(NO)(η1-ONN(t-Bu)O)
N. Xu (2020)
10.1039/c9cc04060a
A nitroxyl-responsive near-infrared fluorescent chemosensor for visualizing H2S/NO crosstalk in biological systems.
Mingwang Yang (2019)
10.1016/J.SNB.2012.08.067
Nitroxyl induced fluorescence enhancement via reduction of a copper(II) coumarin-ester complex: Its application for bioimaging in vivo
Y. Zhou (2012)
10.1016/j.bmcl.2013.02.062
Piloty's acid derivative with improved nitroxyl-releasing characteristics.
Kazuyuki Aizawa (2013)
10.3109/10799893.2010.497152
Hydroxamic acids (therapeutics and mechanism): chemistry, acyl nitroso, nitroxyl, reactive oxygen species, and cell signaling
P. Kovačič (2011)
Effect of Inhibition of S-Nitrosoglutathione Reductase on the NF-κB Pathway
Sharry L. Fears (2009)
10.1021/acschembio.7b00901
Reaction-Based Fluorescent Probes for the Imaging of Nitroxyl (HNO) in Biological Systems.
Baoli Dong (2018)
10.1016/j.phrs.2011.07.002
Aorta from angiotensin II hypertensive mice exhibit preserved nitroxyl anion mediated relaxation responses.
B. Wynne (2012)
10.1089/ars.2010.3852
Nitroxyl in the central nervous system.
C. Choe (2011)
10.1039/c001502d
Alternative photoinduced release of HNO or NO from an acyl nitroso compound, depending on environmental polarity.
K. Matsuo (2010)
10.1021/ja404757s
A reductant-resistant and metal-free fluorescent probe for nitroxyl applicable to living cells.
Kodai Kawai (2013)
10.2991/meep-15.2016.51
Construction and Functional Analysis of Luciferase Reporter Plasmid Containing GSNOR Gene Promoter
Zheng Deliang (2016)
10.1016/J.FREERADBIOMED.2006.11.015
Antioxidant actions of nitroxyl (HNO).
B. Lopez (2007)
10.1021/jz5002902
HNO/NO Conversion Mechanisms of Cu-Based HNO Probes with Implications for Cu,Zn-SOD
Matthew A. Michael (2014)
10.1089/ars.2010.3855
HNO signaling mechanisms.
J. Fukuto (2011)
10.1093/jxb/erz375
Insights to Nitric oxide-Melatonin Crosstalk and N-nitrosomelatonin Functioning in Plants: Where do We Stand?
Soumya Mukherjee (2019)
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