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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
10.1073/PNAS.88.2.365
Purification of a soluble isoform of guanylyl cyclase-activating-factor synthase.
H. Schmidt (1991)
10.1021/JM00109A032
Synthesis and bioactivity of N omega-hydroxyarginine: a possible intermediate in the biosynthesis of nitric oxide from arginine.
G. C. Wallace (1991)
10.1038/333664A0
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)
10.1021/JA01130A044
The Synthetic Application and Mechanism of the Nef Reaction
E. E. Tamelen (1952)
10.1021/BI00424A003
Macrophage oxidation of L-arginine to nitrite and nitrate: nitric oxide is an intermediate.
M. Marletta (1988)
10.1021/JA01506A043
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)
10.1021/TX00019A009
Comparative studies of N-hydroxylation and N-demethylation by microsomal cytochrome P-450.
J. Burstyn (1991)
10.1039/QR9712500407
The oxidation of organic nitrogen compounds with lead tetra-acetate
J. Aylward (1971)
10.1126/science.133.3470.2067
New Class of Antihypertensive Agents
A. A. Rubin (1961)
10.1016/0006-291X(91)90957-9
N omega-hydroxy-L-arginine: a novel arginine analog capable of causing vasorelaxation in bovine intrapulmonary artery.
G. C. Wallace (1991)
10.1021/JA01567A042
aci-Nitroalkanes. II. The Mechanism of the Nef Reaction1
M. Hawthorne (1957)



This paper is referenced by
10.1146/ANNUREV.PHARMTOX.45.120403.095959
Nitroxyl (HNO): chemistry, biochemistry, and pharmacology.
J. Fukuto (2005)
10.1007/s40265-016-0631-y
Therapeutic Potential of Nitroxyl (HNO) Donors in the Management of Acute Decompensated Heart Failure
B. Kemp-Harper (2016)
10.1016/S0006-2952(99)00102-1
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)
10.1016/B978-012721985-1/50014-9
Nitric Oxide in the Autonomic and Enteric Nervous Systems
M. Rand (1995)
10.1007/978-3-0348-8747-2_2
Inducible nitric oxide synthase and inflammation
A. Hobbs (1999)
10.1007/S11882-006-0004-9
Cardiac anaphylaxis: Pathophysiology and therapeutic perspectives
D. Bani (2006)
10.1007/978-1-59259-806-9
Signal Transduction and the Gasotransmitters
R. Wang (2004)
10.1016/0960-894X(95)00048-X
Formation of nitrogen oxides including NO from oxidative cleavage of CN(OH) bonds: A general cytochrome P450-dependent reaction.
A. Jousserandot (1995)
10.1023/A:1020994402835
Exogenous donors of nitric oxide (a chemical aspect)
V. G. Granik (2002)
Nitric oxide in acute and chronic inflammation
M. Paul-Clark (2002)
10.1038/sj.bjp.0703058
Differential actions of L‐cysteine on responses to nitric oxide, nitroxyl anions and EDRF in the rat aorta
A. Ellis (2000)
10.1021/ja312092x
Nitrite reduction mediated by heme models. Routes to NO and HNO?
Julie L Heinecke (2013)
10.1080/10715760400009852
Quinone-enhanced Ascorbate Reduction of Nitric Oxide: Role of Quinone Redox Potential
A. E. Alegría (2004)
10.1021/acs.inorgchem.6b02645
Dual Pathways in the Oxidation of an Osmium(III) Guanidine Complex. Formation of Osmium(VI) Nitrido and Osmium Nitrosyl Complex.
Jing Xiang (2017)
10.1016/S1387-1609(00)01178-6
Oxidation of arylamidoximes by various chemical and biomimetic systems: comparison with their oxidations by hemeproteins
S. V. Goff (2000)
10.1021/tx800392j
Quinone-enhanced reduction of nitric oxide by xanthine/xanthine oxidase.
Pedro Sánchez-Cruz (2009)
10.1002/cmdc.200900233
The Peptidylglycine α‐Amidating Monooxygenase (PAM): A Novel Prodrug Strategy for Amidoximes and N‐Hydroxyguanidines?
D. Schade (2009)
10.1007/978-3-319-30705-3_15
Advances in Breast Cancer Therapy Using Nitric Oxide and Nitroxyl Donor Agents
Debashree Basudhar (2016)
10.1016/j.freeradbiomed.2008.04.036
Generation of nitroxyl by heme protein-mediated peroxidation of hydroxylamine but not N-hydroxy-L-arginine.
Sonia Donzelli (2008)
10.1007/s00726-003-0019-7
Nitric oxide and cell signaling; modulation of redox tone and protein modification
A. Landar (2003)
10.1111/bph.14384
A recent history of nitroxyl chemistry, pharmacology and therapeutic potential
J. Fukuto (2019)
10.1016/S0065-7743(08)60722-8
Chapter 9. The Enzymology and Manipulation of Nitric Oxide Synthase
J. Fukuto (1994)
10.1111/j.1349-7006.1997.tb00349.x
Nitric Oxide Generation from Hydroxyurea via Copper‐catalyzed Peroxidation and Implications for Pharmacological Actions of Hydroxyurea
Keizo Sato (1997)
10.1074/JBC.271.11.6144
The Chemistry and Tumoricidal Activity of Nitric Oxide/Hydrogen Peroxide and the Implications to Cell Resistance/Susceptibility (*)
R. Farias-Eisner (1996)
10.1016/S0891-5849(02)00978-4
Ingress and reactive chemistry of nitroxyl-derived species within human cells.
M. Espey (2002)
10.1016/J.CPLETT.2008.08.064
QM–MM investigation of the reaction products between nitroxyl and O2 in aqueous solution
Carlos M. A. Guardia (2008)
10.1016/j.freeradbiomed.2015.06.002
Signaling and stress: The redox landscape in NOS2 biology.
D. Thomas (2015)
10.1111/j.1476-5381.2009.00150.x
A role for nitroxyl (HNO) as an endothelium‐derived relaxing and hyperpolarizing factor in resistance arteries
K. Andrews (2009)
10.1016/J.CCR.2004.08.010
The chemistry of nitroxyl (HNO) and implications in biology
K. Miranda (2005)
Developing Detection Methods for Nitroxyl
Gail M Johnson (2013)
10.1016/0014-5793(96)00086-5
The role of glutathione in the transport and catabolism of nitric oxide
N. Hogg (1996)
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