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Chemical Oxidation Of N-hydroxyguanidine Compounds. Release Of Nitric Oxide, Nitroxyl And Possible Relationship To The Mechanism Of Biological Nitric Oxide Generation.
J. Fukuto, G. C. Wallace, R. Hszieh, G. Chaudhuri
Published 1992 · Chemistry, Medicine
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N omega-Hydroxy-L-arginine was found to cause vasodilation in arginine-depleted rabbit aorta. It is, therefore, likely to be a biosynthetic intermediate in the conversion of arginine to nitric oxide in this tissue. N-Hydroxyalkylguanidine compounds, including N omega-hydroxy-L-arginine were oxidized with various oxidizing agents and examined for their ability to release nitric oxide. All oxidizing agents tested were capable of oxidizing the N-hydroxyguanidine function but only lead tetra-acetate (Pb(OAc)4) and potassium ferricyanide/hydrogen peroxide (K3FeCN6/H2O2) were capable of generating significant amounts of nitric oxide. Oxidation with K3FeCN6, lead oxide (PbO2) and silver carbonate (Ag2CO3) resulted instead in the release of nitrous oxide (N2O) presumably through the initial release of nitroxyl (HNO).
This paper references
Purification of a soluble isoform of guanylyl cyclase-activating-factor synthase.
H. Schmidt (1991)
Synthesis and bioactivity of N omega-hydroxyarginine: a possible intermediate in the biosynthesis of nitric oxide from arginine.
G. C. Wallace (1991)
Vascular endothelial cells synthesize nitric oxide from L-arginine
R. M. Palmer (1988)
Comparison of the inhibitory potencies of N(G)-methyl-, N(G)-nitro- and N(G)-amino-L-arginine on EDRF function in the rat: evidence for continuous basal EDRF release.
H. Vargas (1991)
The Synthetic Application and Mechanism of the Nef Reaction
E. E. Tamelen (1952)
Macrophage oxidation of L-arginine to nitrite and nitrate: nitric oxide is an intermediate.
M. Marletta (1988)
The Alleged Role of Nitroxyl in Certain Reactions of Aldehydes and Alkyl Halides1
P. A. Smith (1960)
N omega-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine.
D. Stuehr (1991)
Comparative studies of N-hydroxylation and N-demethylation by microsomal cytochrome P-450.
J. Burstyn (1991)
The oxidation of organic nitrogen compounds with lead tetra-acetate
J. Aylward (1971)
New Class of Antihypertensive Agents
A. A. Rubin (1961)
N omega-hydroxy-L-arginine: a novel arginine analog capable of causing vasorelaxation in bovine intrapulmonary artery.
G. C. Wallace (1991)
aci-Nitroalkanes. II. The Mechanism of the Nef Reaction1
M. Hawthorne (1957)
This paper is referenced by
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J. Fukuto (2005)
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B. Kemp-Harper (2016)
Microsomal formation of nitric oxide and cyanamides from non-physiological N-hydroxyguanidines: N-hydroxydebrisoquine as a model substrate.
B. Clement (1999)
Plasmodium-Induced Nitrosative Stress in Anopheles stephensi: The Cost of Host Defense
T. Marie (2005)
Nitric Oxide in the Autonomic and Enteric Nervous Systems
M. Rand (1995)
Inducible nitric oxide synthase and inflammation
A. Hobbs (1999)
Cardiac anaphylaxis: Pathophysiology and therapeutic perspectives
D. Bani (2006)
Signal Transduction and the Gasotransmitters
R. Wang (2004)
Formation of nitrogen oxides including NO from oxidative cleavage of CN(OH) bonds: A general cytochrome P450-dependent reaction.
A. Jousserandot (1995)
Exogenous donors of nitric oxide (a chemical aspect)
V. G. Granik (2002)
Nitric oxide in acute and chronic inflammation
M. Paul-Clark (2002)
Differential actions of L‐cysteine on responses to nitric oxide, nitroxyl anions and EDRF in the rat aorta
A. Ellis (2000)
Nitrite reduction mediated by heme models. Routes to NO and HNO?
Julie L Heinecke (2013)
Quinone-enhanced Ascorbate Reduction of Nitric Oxide: Role of Quinone Redox Potential
A. E. Alegría (2004)
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Jing Xiang (2017)
Oxidation of arylamidoximes by various chemical and biomimetic systems: comparison with their oxidations by hemeproteins
S. V. Goff (2000)
Quinone-enhanced reduction of nitric oxide by xanthine/xanthine oxidase.
Pedro Sánchez-Cruz (2009)
The Peptidylglycine α‐Amidating Monooxygenase (PAM): A Novel Prodrug Strategy for Amidoximes and N‐Hydroxyguanidines?
D. Schade (2009)
Advances in Breast Cancer Therapy Using Nitric Oxide and Nitroxyl Donor Agents
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Generation of nitroxyl by heme protein-mediated peroxidation of hydroxylamine but not N-hydroxy-L-arginine.
Sonia Donzelli (2008)
Nitric oxide and cell signaling; modulation of redox tone and protein modification
A. Landar (2003)
A recent history of nitroxyl chemistry, pharmacology and therapeutic potential
J. Fukuto (2019)
Chapter 9. The Enzymology and Manipulation of Nitric Oxide Synthase
J. Fukuto (1994)
Nitric Oxide Generation from Hydroxyurea via Copper‐catalyzed Peroxidation and Implications for Pharmacological Actions of Hydroxyurea
Keizo Sato (1997)
The Chemistry and Tumoricidal Activity of Nitric Oxide/Hydrogen Peroxide and the Implications to Cell Resistance/Susceptibility (*)
R. Farias-Eisner (1996)
Ingress and reactive chemistry of nitroxyl-derived species within human cells.
M. Espey (2002)
QM–MM investigation of the reaction products between nitroxyl and O2 in aqueous solution
Carlos M. A. Guardia (2008)
Signaling and stress: The redox landscape in NOS2 biology.
D. Thomas (2015)
A role for nitroxyl (HNO) as an endothelium‐derived relaxing and hyperpolarizing factor in resistance arteries
K. Andrews (2009)
The chemistry of nitroxyl (HNO) and implications in biology
K. Miranda (2005)
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Gail M Johnson (2013)
The role of glutathione in the transport and catabolism of nitric oxide
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