3.5.3.18: dimethylargininase
This is an abbreviated version!
For detailed information about dimethylargininase, go to the full flat file.
Word Map on EC 3.5.3.18
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3.5.3.18
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endothelial
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cardiovascular
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artery
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hypertension
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angiotensin
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l-citrulline
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aortic
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umbilical
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vasodilation
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vein
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endothelium-dependent
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dimethylamine
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atherosclerosis
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coronary
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methylarginines
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ng,ng-dimethylarginine
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homocysteine
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medicine
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huvecs
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endothelium-derived
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hyperhomocysteinemia
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nnos
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l-nmma
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ii-induced
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ng-monomethyl-l-arginine
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monomethylarginine
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ox-ldl
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analysis
- 3.5.3.18
- endothelial
- cardiovascular
- artery
- hypertension
- angiotensin
- l-citrulline
- aortic
-
umbilical
-
vasodilation
- vein
-
endothelium-dependent
- dimethylamine
- atherosclerosis
- coronary
-
methylarginines
- ng,ng-dimethylarginine
- homocysteine
- medicine
- huvecs
-
endothelium-derived
- hyperhomocysteinemia
- nnos
-
l-nmma
-
ii-induced
- ng-monomethyl-l-arginine
-
monomethylarginine
-
ox-ldl
- analysis
Reaction
Synonyms
Adv-DDAH, DDAH, DDAH-1, DDAH-2, DDAH-I, DDAH1, DDAH2, DDAHI, DDAHII, dimethlarginine dimethylaminohydrolase, dimethylaminohydrolase, Dimethylargininase, dimethylarginine dimethylamino-hydrolase, dimethylarginine dimethylaminohydrolase, dimethylarginine dimethylaminohydrolase 1, dimethylarginine dimethylaminohydrolase isoform 1, dimethylarginine dimethylaminohydrolase-2, dimethylarginine dimethylaminohydrolase1, dimethylarginine-dimethylaminohydrolase, G6a, hDDAH-1, human DDAH-1, human dimethylarginine dimethylaminohydrolase-1, Nomega,Nomega-dimethyl-L-arginine dimethylaminohydrolase-1, PA1195, PaDDAH
ECTree
3.5.3.18 dimethylargininaseAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 3.5.3.18 - dimethylargininase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
2-chloroacetamidine
irreversible inhibition in a time- and concentration-dependent manner
2-hydroxymethyl-4-chloropyridine
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solution studies support an inactivation mechanismin in which the active site Asp66 residue stabilizes the pyridinium form of the inactivator, which has enhanced reactivity toward the active site Cys, resulting in covalent bond formation, loss of the halide, and irreversible inactivation
4-hydroxy-nonenal
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dose-dependently inhibits DDAH activity with 15% inhibition at 0.01 mM and complete inhibition at 0.5 mM
angiotensin II
1 microM, about 55% relative activity; 1 microM, about 55% relative activity
aprotinin inhibitor
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NG,NG-dimethyl-L-arginine release from freeze-thaw whole blood 34% inhibited
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darbepoetin alpha
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inhibits DDAH in a dose dependent manner, inhibition of DDAH is abolished by incubation with EPO antibody or with antioxidant pyrrolidine dithiocarbamate
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epoetin beta
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inhibits DDAH in a dose dependent manner, inhibition of DDAH is abolished by incubation with EPO antibody or with antioxidant pyrrolidine dithiocarbamate
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erythropoetin
200 units/ml, about 75% relative activity; 200 units/ml, about 75% relative activity
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iodoacetamide
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pH dependent DDAH inactivation, addition of 2.5 mM NG-methyl-L-arginine at pH 8.5 can prevent inactivation by idoacetamide, inactivation may be due to modification at the active site of DDAH, inactivation increases at higher pH values
leupeptin
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NG,NG-dimethyl-L-arginine release from freeze-thaw whole blood 55% inhibited
lipopolysaccharide
1 microg/ml, 24 h, about 55% relative activity; 1 microg/ml, about 55% relative activity
monocrotaline
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DDAH activity and DDAH1, but not DDAH2, protein expression are significantly reduced after 60mg/kg monocrotaline treatment
N-(2-methoxyethyl)-L-arginine
complete inhibition at 100 microM; complete inhibition at 100 microM
N-(but-3-yn-1-yl)-2-chloroethanimidamide
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click chemistry mediated in vivo activity probe that labels the active fraction of DDAH-1 in intact mammalian cells and that can be blocked by the presence of competitive reversible and irreversible inhibitors
N5-(1-iminopropyl)-L-ornithine
crystallization data. Reversible competitive inhibition, consistent with a reversible covalent mode of DDAH inhibition by alkylamidine inhibitors
nitroglycerine
10 microM, 16 h, about 55% relative activity; 10 microM, about 55% relative activity
PD 404182
i.e. 6H-6-imino-(2,3,4,5-tetrahydropyrimido)[1,2-c]-[1,3]benzothiazine, potent active-site competitive inhibitor, about 75% inhibition at 0.05 mM
pentafluorophenyl sulfonates
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between 30-76% DDAH inhibition depending on molecular structure of the pentafluoropenyl sulfonate
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PMSF
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NG,NG-dimethyl-L-arginine release from freeze-thaw whole blood 57% inhibited
protease inhibitor
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NG,NG-dimethyl-L-arginine release from freeze-thaw whole blood 25-85% inhibited
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S-2-amino-4-[N-(2-methoxyethyl)guanidino]butanoic acid benzyl ester
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S-nitroso-L-cysteine
9-15% inhibition of the zinc-free enzyme at 0.5 mM, S-nitrosylation of the active site Cys273 in DDAH-1
2-(N,N-dimethylamino)-diazenolate-2-oxide
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S-nitrosylation of apo-enzyme, holo-enzyme resists, reaction with two of five Cys-residues
2-(N,N-dimethylamino)-diazenolate-2-oxide
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i.e. DEANONOate, inhibition by S-nitrosylation, reversed by dithiothreitol
2-(N,N-dimethylamino)-diazenolate-2-oxide
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i.e. DEANONOate, inhibition by S-nitrosylation, reversed by dithiothreitol
2-(N,N-dimethylamino)diazenolate-2-oxide
1 mM, 50% inhibition of DDAH-1
2-(N,N-dimethylamino)diazenolate-2-oxide
1 mM, 50% inhibition of DDAH-1; 1 mM, 50% inhibition of DDAH-1
2-(N,N-dimethylamino)diazenolate-2-oxide
1 mM, 50% inhibition of DDAH-1
2-amino-4-(NG-methyl-guanidino)butanoic acid
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incubation of lysed red blood cells, dose dependent inhibition of NG,NG-dimethyl-L-arginine degradation with the highest dose (1 mM) reversing the pattern to a net increase in NG,NG-dimethyl-L-arginine concentration for the 1- and 3h time points
2-amino-4-(NG-methyl-guanidino)butanoic acid
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a series of analogues designed, reversible DDAH inhibitors
homocysteine
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inhibition of the expression of DDAH-2 reduces the NO production induced by IL-1beta
L-arginine
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0.1 mM L-arginine competitively inhibits DDAH enzyme activity to 5.6%
lysophosphatidylcholine
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activity is significantly decreased in cells treated with lysophosphatidylcholine (0.005 mg/ml) for 48 h, 0.001-0.005 mM probucol or 0.001 mM pyrrolidindithiocarbamate significantly attenuate inhibition of DDAH activity by lysophosphatidylcholine
N-nitro-L-arginine methylester
1 mM, 1 h, 47.1% relative activity; 1mM, 1 h, 47.1% relative activity
oxidized-low density lipoprotein
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activity is significantly decreased in cells treated with oxidized-low density lipoprotein (0.1 mg/ml) for 48 h, 0.001-0.005 mM probucol or 0.001 mM pyrrolidindithiocarbamat significantly attenuate inhibition of DDAH activity by oxidized-low density lipoprotein
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peroxynitrite
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inhibition of 15% after exposure to peroxynitrite at concentrations ranging from 0.01-0.1 mM, 25% inhibition at 1 mM
S-nitroso-L-homocysteine
96% inhibition of the zinc-free enzyme at 0.5 mM, leads to the unique formation of an N-thiosulfoximide
Zn2+
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one mol per mol of enzyme, apo-enzyme is active, holoenzyme is activated by removal of Zn2+
Zn2+
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incubation of lysed red blood cells, diminished hydrolyis of NG,NG-dimethyl-L-arginine by addition of physiologically relevant concentrations (0.02 mM)
additional information
5 mM of L-cysteine, L-homocysteine, glutathione, dithiothreitol, or Tris(2-carboxyethyl)phosphine-HCl for 30 min at 37°C cannot restore inhibited activity, suggesting that the covalent product N-thiosulfoximide will remain stable under the reducing conditions present in the cytosol
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additional information
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exposure to pathophysiological levels of reactive oxygen has little to no effect on the activity of the enzyme
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additional information
S-ethyl-2-thiopseudourea, S-ethyl-N-phenylisothiourea and phenylene-1,3-bis(ethane-2-isothiourea) do not inhibit DDAH-1 at concentrations below 1 mM
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additional information
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S-ethyl-2-thiopseudourea, S-ethyl-N-phenylisothiourea and phenylene-1,3-bis(ethane-2-isothiourea) do not inhibit DDAH-1 at concentrations below 1 mM
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additional information
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tissue-specific decrease of levels of Ddah1 and Ddah2 RNA after feeding a high-methionine/low-folate diet for 5 to 11 month
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additional information
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incubation of lysed red blood cells with EDTA or glucose failed to attenuate the degradation of NG,NG-dimethyl-L-arginine, incubation of whole blood cells with arginine methyltransferase inhibitors does not reduce NG,NG-dimethyl-L-arginine release
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additional information
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probucol or pyrrolidindithiocarbamate itself have no effect on the activity of DDAH
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additional information
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decrease of DDAH-2 mRNA level induced by 10% serum, ionomycin or endothelial growth factors
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