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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, A. Dutton, T. Miller, K. Houk, J. Fukuto
Published 2003 · Chemistry, Medicine

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The redox chemistry of models of N-hydroxy-L-arginine, the biosynthetic intermediate in the synthesis of NO by the family of nitric oxide synthase enzymes, has been explored experimentally and theoretically. The oxidation of N-hydroxyguanidine model compounds by Cu(II) was studied as a means of establishing possible metabolic fates and intermediates of this important functional group. These studies indicate than an iminoxyl intermediate is formed and may be an important biological species generated from N-hydroxyguanidines including N-hydroxy-L-arginine.
This paper references
10.1016/S0014-5793(96)01451-2
Oxidation of N G‐hydroxyl‐l‐arginine to nitric oxide mediated by respiratory burst: an alternative pathway to NO synthesis
M. Modolell (1997)
10.1021/JM00070A010
Peracid oxidation of an N-hydroxyguanidine compound: a chemical model for the oxidation of N omega-hydroxyl-L-arginine by nitric oxide synthase.
J. Fukuto (1993)
10.1016/0040-4039(95)01242-A
Superoxide anion efficiently performs the oxidative cleavage of CNOH bonds of amidoximes and N-hydroxyguanidines with formation of nitrogen oxides
N. Sennequier (1995)
Nitroxide metabolites from alkylhydroxylamines and N-hydroxyurea derivatives resulting from reductive inhibition of soybean lipoxygenase.
W. Chamulitrat (1992)
10.1073/PNAS.050586597
The interaction of nitric oxide (NO) with the yeast transcription factor Ace1: A model system for NO-protein thiol interactions with implications to metal metabolism.
M. Shinyashiki (2000)
10.1136/ard.56.5.330
Increased serum NG-hydroxy-l-arginine in patients with rheumatoid arthritis and systemic lupus erythematosus as an index of an increased nitric oxide synthase activity
R. Wigand (1997)
10.1021/BI973153G
Reaction between S-nitrosothiols and thiols: generation of nitroxyl (HNO) and subsequent chemistry.
P. Wong (1998)
10.1016/0014-4800(68)90051-8
Effect of hydroxyurea analogues in regenerating rat liver.
R. Hill (1968)
10.1016/0006-2952(95)02098-5
Oxidation of N-hydroxyguanidine by nitric oxide and the possible generation of vasoactive species.
J. Yoo (1995)
10.1016/0006-2952(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)
10.1073/pnas.041481598
On the acidity and reactivity of HNO in aqueous solution and biological systems
M. D. Bartberger (2001)
10.1111/J.1432-1033.1982.TB06653.X
Characterization of the active site of ribonucleotide reductase of Escherichia coli, bacteriophage T4 and mammalian cells by inhibition studies with hydroxyurea analogues.
I. Larsen (1982)
10.1021/TX950109Y
Evidence that nitric oxide enhances cadmium toxicity by displacing the metal from metallothionein.
R. Misra (1996)
10.1006/NIOX.1998.0187
Nitrogen oxides and hydroxyguanidines: formation of donors of nitric and nitrous oxides and possible relevance to nitrous oxide formation by nitric oxide synthase.
G. Southan (1998)
10.1021/JM00368A024
Novel N-hydroxyguanidine derivatives as anticancer and antiviral agents.
A. Tai (1984)
10.1063/1.467306
A complete basis set model chemistry. IV. An improved atomic pair natural orbital method
J. A. Montgomery (1994)
On the mechanism of the nitric oxide synthase-catalyzed conversion of N omega-hydroxyl-L-arginine to citrulline and nitric oxide.
H. Korth (1994)
10.1002/CHEM.19970030417
Biosynthesis of Nitric Oxide—Quantum Chemical Modelling of Nω‐Hydroxy‐l‐arginine Formation
E. Wasielewska (1997)
10.1021/BI981175C
Microsomal cytochrome P450 dependent oxidation of N-hydroxyguanidines, amidoximes, and ketoximes: mechanism of the oxidative cleavage of their C=N(OH) bond with formation of nitrogen oxides.
A. Jousserandot (1998)
10.1039/A901539F
New strategies for new organic molecules with large second order hyperpolarizabilities
M. Magnoni (1999)
10.1039/P29860001765
σI Values for heterocycles
P. J. Taylor (1986)
10.1021/JA991876C
Theoretical Studies on NG-Hydroxy-l-arginine and Derived Radicals: Implications for the Mechanism of Nitric Oxide Synthase
D. Tantillo (2000)
10.1021/JP960311P
Amidine N−C(N)−N Skeleton: Its Structure in Isolated and Hydrogen-Bonded Guanidines from ab Initio Calculations
R. Caminiti (1996)
10.1016/0014-2999(95)00046-N
Increase in serum NG-hydroxy-L-arginine in rats treated with bacterial lipopolysaccharide.
M. Hecker (1995)
10.1074/JBC.275.12.8582
Unusual Oxidative Chemistry ofN ω-Hydroxyarginine and N-Hydroxyguanidine Catalyzed at an Engineered Cavity in a Heme Peroxidase*
J. Hirst (2000)
10.1096/fasebj.14.1.166
Inactivation of zinc finger transcription factors provides a mechanism for a gene regulatory role of nitric oxide
K. Kröncke (2000)
10.1146/ANNUREV.PH.57.030195.003423
Nitric oxide synthases: properties and catalytic mechanism.
O. Griffith (1995)
10.1016/S0741-8329(99)00056-7
Reaction of nitroxyl, an aldehyde dehydrogenase inhibitor, with N-acetyl-L-cysteine.
D. Shoeman (2000)
10.1016/0076-6879(91)05122-C
Ligand substitution and sulfhydryl reactivity of metallothionein.
C. F. Shaw (1991)
10.1021/JA01506A043
The Alleged Role of Nitroxyl in Certain Reactions of Aldehydes and Alkyl Halides1
P. A. Smith (1960)
10.1042/BJ3170017
Oxidative denitrification of N omega-hydroxy-L-arginine by the superoxide radical anion.
S. Everett (1996)
10.1016/S0891-5849(97)00203-7
Oxidative denitrification of the antitumour drug hydroxyguanidine.
S. Everett (1998)
Arginase activity in human breast cancer cell lines: N(omega)-hydroxy-L-arginine selectively inhibits cell proliferation and induces apoptosis in MDA-MB-468 cells.
R. Singh (2000)
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)
10.1006/BBRC.1994.1909
Inhibition of rat liver arginase by an intermediate in NO biosynthesis, NG-hydroxy-L-arginine: implications for the regulation of nitric oxide biosynthesis by arginase.
F. Daghigh (1994)
10.1006/BBRC.1994.1668
Bioassay discrimination between nitric oxide (NO.) and nitroxyl (NO-) using L-cysteine.
R. Pino (1994)
10.1080/02603598808072309
The Aqueous Solution Chemistry of Nitrogen in Low Positive Oxidation States
F. T. Bonner (1988)
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)
10.1038/236400A0
Biological Sciences: Hydroxyguanidine—a New Antitumour Drug
R. Adamson (1972)
10.1016/S0006-291X(05)80004-X
Formation of nitrogen oxides and citrulline upon oxidation of N omega-hydroxy-L-arginine by hemeproteins.
J. L. Boucher (1992)
10.1073/pnas.162095599
The reduction potential of nitric oxide (NO) and its importance to NO biochemistry
M. D. Bartberger (2002)
10.1016/S0891-5849(02)00969-3
Metabolism of carcinogenic urethane to nitric oxide is involved in oxidative DNA damage.
K. Sakano (2002)
10.1006/BBRC.1994.2371
N omega-hydroxyl-L-arginine, an intermediate in the L-arginine to nitric oxide pathway, is a strong inhibitor of liver and macrophage arginase.
J. L. Boucher (1994)
10.1007/s000180050355
Nitrosative and oxidative modulation of iron regulatory proteins
C. Bouton (1999)
10.1016/S0891-5849(98)00120-8
Hydroxyguanidines inhibit peroxynitrite-induced oxidation.
G. Southan (1998)
10.1016/S0960-894X(02)00185-3
Electrochemical and peroxidase oxidation study of N'-hydroxyguanidine derivatives as NO donors.
T. Cai (2002)
10.1016/0300-9084(96)88181-8
On the mechanism of nitric oxide formation upon oxidative cleavage of C = N(OH) bonds by NO-synthases and cytochromes P450.
D. Mansuy (1995)
10.1016/0168-1702(89)90069-5
Inhibition of murine coronavirus RNA synthesis by hydroxyguanidine derivatives
J. Keck (1989)
10.5860/choice.37-0940
Advanced Inorganic Chemistry
F. Cotton (1999)



This paper is referenced by
10.1016/J.CRVI.2004.12.002
Production of NA by endothelial NO-synthase: an in vitro versus in vivo study.
A. Meulemans (2005)
10.1016/j.cbi.2013.09.019
Cytotoxicity of nitroxyl (HNO/NO-) against normal and cancer human cells.
Aleksandra Augustyniak (2013)
10.1016/J.JCHROMB.2005.07.002
Capillary electrophoresis of the electrochemical oxidation products of Ng-hydroxy-l-arginine at physiological pH.
A. Meulemans (2005)
10.1002/cmdc.200900233
The Peptidylglycine α‐Amidating Monooxygenase (PAM): A Novel Prodrug Strategy for Amidoximes and N‐Hydroxyguanidines?
D. Schade (2009)
10.1016/j.jinorgbio.2008.12.012
N-Hydroxyguanidines oxidation by a N3S copper-complex mimicking the reactivity of Dopamine beta-Hydroxylase.
P. Slama (2009)
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)
Mechanism(s) of ischaemia/reperfusion injury and cardioprotection
K. Chin (2015)
10.1146/ANNUREV.PHARMTOX.45.120403.095959
Nitroxyl (HNO): chemistry, biochemistry, and pharmacology.
J. Fukuto (2005)
10.1155/2016/4867124
Nitroxyl (HNO): A Reduced Form of Nitric Oxide with Distinct Chemical, Pharmacological, and Therapeutic Properties
Mai E. Shoman (2016)
10.1021/ja203652z
Rapid and selective nitroxyl (HNO) trapping by phosphines: kinetics and new aqueous ligations for HNO detection and quantitation.
J. Reisz (2011)
10.3109/10715762.2012.746460
Discriminative EPR detection of NO and HNO by encapsulated nitronyl nitroxides
A. Bobko (2013)
10.1016/j.ajpath.2015.10.001
Exocytosis of Endothelial Lysosome-Related Organelles Hair-Triggers a Patchy Loss of Glycocalyx at the Onset of Sepsis.
J. Zullo (2016)
10.1016/J.BBRC.2004.02.163
Aromatic N-hydroxyguanidines as new reduction cosubstrates for dopamine beta-hydroxylase.
P. Slama (2004)
10.1562/2005-04-23-RA-496
Quinone-sensitized Steady-state Photolysis of Acetophenone Oximes Under Aerobic Conditions: Kinetics and Product Studies†
A. Park (2006)
10.1016/B978-0-12-800934-5.00013-X
Detection of HNO by Membrane Inlet Mass Spectrometry
T. A. Chavez (2017)
10.1016/S0076-6879(05)96003-5
Quantum mechanical determinations of reaction mechanisms, acid base, and redox properties of nitrogen oxides and their donors.
A. Dutton (2005)
10.1016/j.jinorgbio.2012.09.024
Oxidation of N-hydroxy-l-arginine by hypochlorous acid to form nitroxyl (HNO).
Meredith R. Cline (2013)
10.1021/acs.inorgchem.6b00652
Aerobic Oxidation of an Osmium(III) N-Hydroxyguanidine Complex To Give Nitric Oxide.
Jing Xiang (2016)
10.1021/TX0496800
The physiological chemistry and biological activity of nitroxyl (HNO): the neglected, misunderstood, and enigmatic nitrogen oxide.
J. Fukuto (2005)
10.1039/c7dt01960b
Metal-mediated reactions between dialkylcyanamides and acetamidoxime generate unusual (nitrosoguanidinate)nickel(ii) complexes.
Zarina M Bikbaeva (2017)
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)
10.1002/cbic.200400271
The Chemistry and Biology of Nitroxyl (HNO): A Chemically Unique Species with Novel and Important Biological Activity
J. Fukuto (2005)
10.1016/j.pharmthera.2010.02.005
Modulating the NO generating system from a medicinal chemistry perspective: current trends and therapeutic options in cardiovascular disease.
D. Schade (2010)
10.1021/jo300449n
Synthesis of phidianidines A and B.
H. Lin (2012)
10.1039/c0ob01117g
Prodrug design for the potent cardiovascular agent Nω-hydroxy-L-arginine (NOHA): synthetic approaches and physicochemical characterization.
D. Schade (2011)
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