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Information on EC 1.4.3.21 - primary-amine oxidase and Organism(s) Rattus norvegicus and UniProt Accession O08590

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EC Tree
     1 Oxidoreductases
         1.4 Acting on the CH-NH2 group of donors
             1.4.3 With oxygen as acceptor
                1.4.3.21 primary-amine oxidase
IUBMB Comments
A group of enzymes that oxidize primary monoamines but have little or no activity towards diamines, such as histamine, or towards secondary and tertiary amines. They are copper quinoproteins (2,4,5-trihydroxyphenylalanine quinone) and, unlike EC 1.4.3.4, monoamine oxidase, are sensitive to inhibition by carbonyl-group reagents, such as semicarbazide. In some mammalian tissues the enzyme also functions as a vascular-adhesion protein (VAP-1).
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Rattus norvegicus
UNIPROT: O08590
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Word Map
The taxonomic range for the selected organisms is: Rattus norvegicus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
vap-1, vascular adhesion protein-1, copper amine oxidase, benzylamine oxidase, bovine serum amine oxidase, plasma amine oxidase, ssao/vap-1, bovine plasma amine oxidase, copper-containing amine oxidase, primary amine oxidase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
semicarbazide-sensitive amine oxidase
-
copper-dependent amine oxidase
-
-
semicarbazide-sensitive amine oxidase
-
-
semicarbazide-sensitive amine oxidase/vascular adhesion protein-1
-
-
SSAO/VAP-1
-
-
vascular adhesion protein 1
-
-
vascular adhesion protein-1
-
-
SYSTEMATIC NAME
IUBMB Comments
primary-amine:oxygen oxidoreductase (deaminating)
A group of enzymes that oxidize primary monoamines but have little or no activity towards diamines, such as histamine, or towards secondary and tertiary amines. They are copper quinoproteins (2,4,5-trihydroxyphenylalanine quinone) and, unlike EC 1.4.3.4, monoamine oxidase, are sensitive to inhibition by carbonyl-group reagents, such as semicarbazide. In some mammalian tissues the enzyme also functions as a vascular-adhesion protein (VAP-1).
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-methylhistamine + O2 + H2O
?
show the reaction diagram
-
-
-
?
benzylamine + O2 + H2O
benzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
beta-phenylethylamine + O2 + H2O
beta-phenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
?
serotonin + O2 + H2O
(5-hydroxy-1H-indol-3yl)acetaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
?
tyramine + O2 + H2O
4-hydroxyphenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
?
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
hexakis(benzylammonium) decavanadate (V) dihydrate + H2O + O2
?
show the reaction diagram
-
-
-
-
?
methylamine + H2O + O2
methanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
tyramine + H2O + O2
4-hydroxyphenylethanal + NH3 + H2O2
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
docking of substrates to the enzyme, the enzyme shows electrostatic control of the docking process, overview. The active site contains two negatively charged amino acid residues which seem to interact with positively charged groups of the substrate molecules
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Semicarbazide
causes significant decreases in the oxidative deamination activity of four among the five substrates catalyzed by SSAO
(2-phenylprop-2-en-1-yl)hydrazine
-
-
(Z)-3-fluoro-2-(4-methoxybenzyl)allylamine hydrochloride
-
i.e. LJP 1586. Potent, specific, and orally available inhibitor of SSAO activity is an effective anti-inflammatory compound in vivo
1-ethyl-2-[2-(4-fluorophenyl)prop-2-en-1-yl]hydrazine
-
-
1-[2-(4-fluorophenyl)prop-2-en-1-yl]-2-methylhydrazine
-
-
2-amino-N-[2-fluoro-3-(trifluoromethyl)benzyl]acetamide
-
-
2-amino-N-[2-fluoro-5-(trifluoromethyl)benzyl]acetamide
-
-
2-amino-N-[3-fluoro-5-(trifluoromethyl)benzyl]acetamide
-
-
2-amino-N-[4-fluoro-3-(trifluoromethyl)benzyl]acetamide
-
-
3-(4-methoxyphenyl)-N-methyl-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
-
-
3-[2-(3-methoxyphenyl)ethyl]-2,5-dihydro-1H-pyrrole
-
-
aminoguanidine
-
strongly inhibits adipocyte semicarbazide-sensitive amine oxidase and slightly reduces fat deposition in obese Zucker rats. Aminoguanidine may be useful for treating obesity via its SSAO blocking properties
hydroxylamine
-
elicits hypotension in the rat. This effect is due in part to its conversion to nitric oxide and in part to a hydralazine-like action involving SSAO inhibition
MDL 72223
-
-
-
N-allyl-3-(4-methoxyphenyl)-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
-
-
N-ethyl-3-(4-methoxyphenyl)-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
-
-
Phenelzine
-
-
Semicarbazide
[(2E)-3-fluoro-2-phenylprop-2-en-1-yl]hydrazine
-
-
[2-(2-methylphenyl)prop-2-en-1-yl]hydrazine
-
-
[2-(4-chlorophenyl)prop-2-en-1-yl]hydrazine
-
-
[2-(4-fluorophenyl)prop-2-en-1-yl]hydrazine
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
SSAO activity remains unchanged during starvation
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0127
benzylamine
-
37°C
0.014
hexakis(benzylammonium) decavanadate (V) dihydrate
-
37°C
additional information
additional information
-
kinetic analysis at different ionic strength and pH, overview
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.042 - 0.07011
3-(4-methoxyphenyl)-N-methyl-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
0.225 - 0.28
N-allyl-3-(4-methoxyphenyl)-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
0.17 - 0.23
N-ethyl-3-(4-methoxyphenyl)-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
0.0054 - 0.0128
Semicarbazide
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000002
(2-phenylprop-2-en-1-yl)hydrazine
Rattus norvegicus
-
-
0.000009
(Z)-3-fluoro-2-(4-methoxybenzyl)allylamine hydrochloride
Rattus norvegicus
-
-
0.00023
1-ethyl-2-[2-(4-fluorophenyl)prop-2-en-1-yl]hydrazine
Rattus norvegicus
-
-
0.0000017
1-[2-(4-fluorophenyl)prop-2-en-1-yl]-2-methylhydrazine
Rattus norvegicus
-
-
0.000015
2-amino-N-[2-fluoro-3-(trifluoromethyl)benzyl]acetamide
Rattus norvegicus
-
-
0.00001
2-amino-N-[2-fluoro-5-(trifluoromethyl)benzyl]acetamide
Rattus norvegicus
-
-
0.000033
2-amino-N-[3-fluoro-5-(trifluoromethyl)benzyl]acetamide
Rattus norvegicus
-
-
0.00018
2-amino-N-[4-fluoro-3-(trifluoromethyl)benzyl]acetamide
Rattus norvegicus
-
-
0.042
3-(4-methoxyphenyl)-N-methyl-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
Rattus norvegicus
-
-
0.0005
3-[2-(3-methoxyphenyl)ethyl]-2,5-dihydro-1H-pyrrole
Rattus norvegicus
-
-
0.225
N-allyl-3-(4-methoxyphenyl)-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
Rattus norvegicus
-
-
0.17
N-ethyl-3-(4-methoxyphenyl)-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
Rattus norvegicus
-
-
0.000005
[(2E)-3-fluoro-2-phenylprop-2-en-1-yl]hydrazine
Rattus norvegicus
-
-
0.000004
[2-(2-methylphenyl)prop-2-en-1-yl]hydrazine
Rattus norvegicus
-
-
0.000003
[2-(4-chlorophenyl)prop-2-en-1-yl]hydrazine
Rattus norvegicus
-
-
0.000006
[2-(4-fluorophenyl)prop-2-en-1-yl]hydrazine
Rattus norvegicus
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00015
substrate benzylamine, at low substrate concentration
0.00023
substrate beta-phenylethylamine, at low substrate concentration
0.00025
substrate tyramine, at low substrate concentration
0.00078
substrate 1-methylhistamine, at low substrate concentration
0.00108
substrate tyramine, at high substrate concentration
0.00136
substrate beta-phenylethylamine, at high substrate concentration
0.00165
substrate 1-methylhistamine, at high substrate concentration
0.00193
substrate benzylamine, at high substrate concentration
0.00388
substrate serotonin, at high substrate concentration
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.6 - 10.2
-
assay range
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
nine-week-old male Wistar rats
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
treatment with benzylamine + vanadate reduces the elevated serum SSAO activity, decreases the accumulation of advanced-glycation end products and increases the bioavailability of nitric oxide in diabetic animals, similarly to insulin
Manually annotated by BRENDA team
-
very high activity
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
of adipocytes
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
VAP-1 mediates lymphocyte adhesion to endothelia at sites of inflammation in vitro and in vivo. Inhibition of the SSAO activity of the enzyme by semicarbazid significantly decreases inflammatory cell infiltration in liver allografts, but does not influence the luminal expression of VAP-1 in the liver allografts
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
AOC3_RAT
763
1
84981
Swiss-Prot
Secretory Pathway (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
184000
-
non-denaturing PAGE
93000
-
2 * 93000, SDS-PAGE after treatment with 2-mercaptoethanol
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in COS-1 cells
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
-
hexakis(benzylammonium) decavanadate (V) dihydrate acts as a prodrug of peroxovanadate insulin mimetics. SSAO oxidizes hexakis(benzylammonium) decavanadate (V) dihydrate to the same extent as it does benzylamine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ochiai, Y.; Itoh, K.; Sakurai, E.; Adachi, M.; Tanaka, Y.
Substrate selectivity of monoamine oxidase A, monoamine oxidase B, diamine oxidase, and semicarbazide-sensitive amine oxidase in COS-1 expression systems
Biol. Pharm. Bull.
29
2362-2366
2006
Rattus norvegicus (O08590)
Manually annotated by BRENDA team
Yraola, F.; Garcia-Vicente, S.; Marti, L.; Albericio, F.; Zorzano, A.; Royo, M.
Understanding the mechanism of action of the novel SSAO substrate (C7NH10)6(V10O28).2H2O, a prodrug of peroxovanadate insulin mimetics
Chem. Biol. Drug Des.
69
423-428
2007
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Dunkel, P.; Gelain, A.; Barlocco, D.; Haider, N.; Gyires, K.; Sperlagh, B.; Magyar, K.; Maccioni, E.; Fadda, A.; Matyus, P.
Semicarbazide-sensitive amine oxidase/vascular adhesion protein 1: recent developments concerning substrates and inhibitors of a promising therapeutic target
Curr. Med. Chem.
15
1827-1839
2008
Bos taurus, Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Fracassini, L.; Alfarano, C.; Romagnani, B.; Pirisino, R.; Raimondi, L.
Endogenous substrates of the semicarbazide-sensitive amine oxidase increased nitric oxide production in rat white adipocytes
Inflamm. Res.
57
S53-S54
2008
Rattus norvegicus
Manually annotated by BRENDA team
Yabanoglu, S.; Ucar, G.; Gokhan, N.; Salgin, U.; Yesilada, A.; Bilgin, A.A.
Interaction of rat lung SSAO with the novel 1-N-substituted thiocarbamoyl-3-substituted phenyl-5-(2-pyrolyl)-2-pyrazoline derivatives
J. Neural Transm.
114
769-773
2007
Rattus norvegicus
Manually annotated by BRENDA team
Soltesz, Z.; Tabi, T.; Halasz, A.S.; Palfi, M.; Kocsis, E.; Magyar, K.; Toth, M.; Szoekoe, E.
Studies on the insulinomimetic effects of benzylamine, exogenous substrate of semicarbazide-sensitive amine oxidase enzyme in streptozotocin induced diabetic rats
J. Neural Transm.
114
851-855
2007
Rattus norvegicus
Manually annotated by BRENDA team
Vidrio, H.; Medina, M.
Hypotensive effect of hydroxylamine, an endogenous nitric oxide donor and SSAO inhibitor
J. Neural Transm.
114
863-865
2007
Rattus norvegicus
Manually annotated by BRENDA team
Sibon, I.; Mercier, N.; Darret, D.; Lacolley, P.; Lamaziere, J.M.
Association between semicarbazide-sensitive amine oxidase, a regulator of the glucose transporter, and elastic lamellae thinning during experimental cerebral aneurysm development: laboratory investigation
J. Neurosurg.
108
558-566
2008
Rattus norvegicus
Manually annotated by BRENDA team
ORourke, A.M.; Wang, E.Y.; Miller, A.; Podar, E.M.; Scheyhing, K.; Huang, L.; Kessler, C.; Gao, H.; Ton-Nu, H.T.; Macdonald, M.T.; Jones, D.S.; Linnik, M.D.
Anti-inflammatory effects of LJP 1586 [Z-3-fluoro-2-(4-methoxybenzyl)allylamine hydrochloride], an amine-based inhibitor of semicarbazide-sensitive amine oxidase activity
J. Pharmacol. Exp. Ther.
324
867-875
2008
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Carpene, C.; Iffiu-Soltesz, Z.; Bour, S.; Prevot, D.; Valet, P.
Reduction of fat deposition by combined inhibition of monoamine oxidases and semicarbazide-sensitive amine oxidases in obese Zucker rats
Pharmacol. Res.
56
522-530
2007
Rattus norvegicus
Manually annotated by BRENDA team
Prevot, D.; Soltesz, Z.; Abello, V.; Wanecq, E.; Valet, P.; Unzeta, M.; Carpene, C.
Prolonged treatment with aminoguanidine strongly inhibits adipocyte semicarbazide-sensitive amine oxidase and slightly reduces fat deposition in obese Zucker rats
Pharmacol. Res.
56
70-79
2007
Rattus norvegicus
Manually annotated by BRENDA team
Carpene, C.; Abello, V.; Iffiu-Soltesz, Z.; Mercier, N.; Feve, B.; Valet, P.
Limitation of adipose tissue enlargement in rats chronically treated with semicarbazide-sensitive amine oxidase and monoamine oxidase inhibitors
Pharmacol. Res.
57
426-434
2008
Rattus norvegicus
Manually annotated by BRENDA team
Iffiu-Soltesz, Z.; Prevot, D.; Carpene, C.
Influence of prolonged fasting on monoamine oxidase and semicarbazide-sensitive amine oxidase activities in rat white adipose tissue
J. Physiol. Biochem.
65
11-23
2009
Rattus norvegicus
Manually annotated by BRENDA team
Stevanato, R.; Cardillo, S.; Braga, M.; De Iuliis, A.; Battaglia, V.; Toninello, A.; Agostinelli, E.; Vianello, F.
Preliminary kinetic characterization of a copper amine oxidase from rat liver mitochondria matrix
Amino Acids
40
713-720
2011
Rattus norvegicus
Manually annotated by BRENDA team
Martelius, T.; Salmi, M.; Krogerus, L.; Loginov, R.; Schoultz, M.; Karikoski, M.; Miiluniemi, M.; Soots, A.; Hoeckerstedt, K.; Jalkanen, S.; Lautenschlager, I.
Inhibition of semicarbazide-sensitive amine oxidases decreases lymphocyte infiltration in the early phases of rat liver allograft rejection
Int. J. Immunopathol. Pharmacol.
21
911-920
2009
Rattus norvegicus
Manually annotated by BRENDA team