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4-aminomethylpyridine dihydrochloride + H2O + O2
?
8% substrate activity of 1 mM 4-aminomethylpyridine dihydrochloride as percentage of the activity of the best substrate (putrescine, 1 mM) for various amine oxidases
-
-
?
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
-
-
-
?
histamine + H2O + O2
(imidazol-4-yl)acetaldehyde + NH3 + H2O2
-
-
-
?
putrescine + H2O + O2
?
-
-
-
?
1,3-diaminopropane + H2O + O2
3-aminopropanal + NH3 + H2O2
-
30% activity compared to activity with putrescine
-
-
?
1,4-diaminobutane + H2O + O2
4-aminobutanal + NH3 + H2O2
1,5-diaminopentane + H2O + O2
5-aminopentanal + NH3 + H2O2
2-hydroxycadaverine + H2O + O2
?
-
-
-
-
?
2-hydroxyputrescine + H2O + O2
?
-
-
-
-
?
3-hydroxycadaverine + H2O + O2
?
-
-
-
-
?
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
-
-
-
-
?
butylamine + H2O + O2
butanal + NH3 + H2O2
-
-
-
-
r
cadaverine + H2O + O2
5-aminopentanal + NH3 + H2O2
cadaverine + H2O + O2
?
-
-
-
-
?
ethylamine + H2O + O2
acetaldehyde + NH3 + H2O2
-
-
-
-
r
ethylenediamine + H2O + O2
?
-
-
-
-
r
histamine + H2O + O2
(imidazol-4-yl)acetaldehyde + NH3 + H2O2
L-lysine methyl ester + H2O + O2
?
-
-
-
-
?
N-methyl-1,3-diaminopropane + H2O + O2
N-methyl-3-aminopropanal + NH3 + H2O2
-
40% activity compared to activity with putrescine
-
-
?
N-methylputrescine + H2O + O2
4-(methylamino)butanal + NH3 + H2O2
-
75% activity compared to activity with putrescine
-
-
?
p-dimethylaminomethylbenzylamine + H2O + O2
p-dimethylaminomethylbenzaldehyde + NH3 + H2O2
-
-
-
?
propylamine + H2O + O2
propanal + NH3 + H2O2
-
-
-
-
r
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
additional information
?
-
-
low activity with n-butylamine or 1,6-diaminohexane as substrate
-
-
?
1,4-diaminobutane + H2O + O2
4-aminobutanal + NH3 + H2O2
-
-
-
?
1,4-diaminobutane + H2O + O2
4-aminobutanal + NH3 + H2O2
-
-
-
?
1,4-diaminobutane + H2O + O2
4-aminobutanal + NH3 + H2O2
-
best substrate
-
-
?
1,5-diaminopentane + H2O + O2
5-aminopentanal + NH3 + H2O2
-
-
-
?
1,5-diaminopentane + H2O + O2
5-aminopentanal + NH3 + H2O2
-
-
-
?
cadaverine + H2O + O2
5-aminopentanal + NH3 + H2O2
-
-
-
-
?
cadaverine + H2O + O2
5-aminopentanal + NH3 + H2O2
-
80% activity compared to activity with putrescine
-
-
?
histamine + H2O + O2
(imidazol-4-yl)acetaldehyde + NH3 + H2O2
-
-
-
-
?
histamine + H2O + O2
(imidazol-4-yl)acetaldehyde + NH3 + H2O2
-
-
-
?
histamine + H2O + O2
(imidazol-4-yl)acetaldehyde + NH3 + H2O2
-
-
-
?
histamine + H2O + O2
(imidazol-4-yl)acetaldehyde + NH3 + H2O2
-
60% activity compared to activity with putrescine
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
-
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
treatment of diamine oxidase with reducing agents induces ability to catalyze oxidative deamination of substrates of monoamine oxidase EC 1.4.3.4
-
?
RCH2NH2 + H2O + O2
RCHO + NH3 + H2O2
-
enzyme plays a protective role against histamine in diseases such as ischaemic bowel syndrome, mesenteric infarction and ulcerative colitis
-
?
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1-(3,5-diethoxypyridin-4-yl)methanamine dihydrochloride
-
1-[3,5-bis(ethylsulfanyl)pyridin-4-yl]methanamine dihydrochloride
-
1-[3,5-bis(tert-butylsulfanyl)pyridin-4-yl]methanamine dihydrochloride
-
1-[3-(benzyloxy)-5-ethoxypyridin-4-yl]methanamine dihydrochloride
-
2-ethylaminobenzylamine dihydrochloride
-
2-methylaminobenzylamine dihydrochloride
-
3,3'-[[4-(aminomethyl)pyridine-3,5-diyl]bis(oxy)]dipropan-1-ol dihydrochloride
-
3-(1-piperidinyl)-4-aminomethylpyridine dihydrochloride hemihydrate
-
3-amino-4-aminomethylpyridine dihydrochloride
-
3-cycloheptylamino-4-aminomethylpyridine dihydrochloride monohydrate
-
3-cyclohexylamino-4-aminomethylpyridine dihydrochloride monohydrate
-
3-cyclohexylmethylamino-4-aminomethylpyridine dihydrochloride monohydrate
-
3-cyclopentylamino-4-aminomethylpyridine dihydrochloride hemihydrate
-
3-cyclopropylamino-4-aminomethylpyridine dihydrochloride sesquihydrate
-
3-ethylamino-4-aminomethylpyridine dihydrochloride
-
3-methylamino-4-aminomethylpyridine dihydrochloride
-
3-[(1-methylethyl)amino]-4-aminomethylpyridine dihydrochloride
-
4,4'-[[4-(aminomethyl)pyridine-3,5-diyl]bis(oxy)]dibutan-1-ol dihydrochloride
-
4-(aminomethyl)-N,N'-bis(1-methylethyl)pyridine-3,5-diamine dihydrochloride
-
4-(aminomethyl)-N,N'-dibutylpyridine-3,5-diamine dihydrochloride
-
4-(aminomethyl)-N,N'-diethylpyridine-3,5-diamine dihydrochloride
-
4-(aminomethyl)-N,N'-dimethylpyridine-3,5-diamine dihydrochloride
-
4-(aminomethyl)-N-methylpyridine-3,5-diamine dihydrochloride
-
histamine
substrate inhibition at 0.5 mM
1,3-diaminopropane
-
10 mM with 2 mM N-methylputrescine as substrate, 93% relative inhibition
1,4-Diamino-2-butanone
-
potent reversible inhibitors
1,5-Diamino-3-pentanone
-
potent reversible inhibitors
amiloride
-
diuretic drug, competitive vs. agmatine and putrescine oxidation
clonidine
-
antihypertensive drug, competitive vs. agmatine and putrescine oxidation
diaminoacetone
-
0.1 mM, significant inhibition
gabexate mesylate
-
anti coagulant drug, competitive vs. agmatine and putrescine oxidation
H2O2
-
uncompetitive vs. p-dimethylaminomethylbenzylamine
Isonicotinic acid hydrazide
-
-
m-phenylenediamine
-
competitive vs. cadaverine
n-butylamine
-
10 mM with 2 mM N-methylputrescine as substrate, 60% relative inhibition
N-methyl-1,3-diamonopropane
-
10 mM with 2 mM N-methylputrescine as substrate, 61% relative inhibition
N-methylbutylamine
-
10 mM with 2 mM N-methylputrescine as substrate, 19% relative inhibition
N-methylpropylamine
-
10 mM with 2 mM N-methylputrescine as substrate, 22% relative inhibition
n-Propylamine
-
10 mM with 2 mM N-methylputrescine as substrate, 48% relative inhibition
NaN3
-
uncompetitive vs. p-dimethylaminomethylbenzylamine, N3- is equatorially coordinated to a tetragonal Cu(II) center
NH3
-
competitive vs. p-dimethylaminomethylbenzylamine, uncompetitive vs. O2
o-phenylenediamine
-
competitive vs. cadaverine
thiocyanate
-
uncompetitive vs. p-dimethylaminomethylbenzylamine, SCN- is equatorially coordinated to a tetragonal Cu(II) center
aminoguanidine
-
-
aminoguanidine
-
model of inhibition mechanism
additional information
alkylamino derivatives of 4-aminomethylpyridine, substrate-like, reversible inhibitors
-
additional information
-
substrate inhibition with diamines
-
additional information
-
no substrate inhibition with monoamines
-
additional information
-
primary amines inhibit pea and pig kidney DAO activities more strongly than the Hyoscyamus niger. N-methylated amines are stronger inhibitors of the Hyoscyamus enzyme than of the others DAOs
-
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1
1-[3,5-bis(ethylsulfanyl)pyridin-4-yl]methanamine dihydrochloride
Sus scrofa
-
0.00003
3-amino-4-aminomethylpyridine dihydrochloride
Sus scrofa
-
0.018
3-cycloheptylamino-4-aminomethylpyridine dihydrochloride monohydrate
Sus scrofa
-
0.016
3-cyclohexylamino-4-aminomethylpyridine dihydrochloride monohydrate
Sus scrofa
-
0.05
3-cyclohexylmethylamino-4-aminomethylpyridine dihydrochloride monohydrate
Sus scrofa
-
0.019
3-cyclopentylamino-4-aminomethylpyridine dihydrochloride hemihydrate
Sus scrofa
-
0.05
3-cyclopropylamino-4-aminomethylpyridine dihydrochloride sesquihydrate
Sus scrofa
-
0.00005
3-ethylamino-4-aminomethylpyridine dihydrochloride
Sus scrofa
-
0.000016
3-methylamino-4-aminomethylpyridine dihydrochloride
Sus scrofa
-
0.016
3-[(1-methylethyl)amino]-4-aminomethylpyridine dihydrochloride
Sus scrofa
-
0.001
4-(aminomethyl)-N,N'-bis(1-methylethyl)pyridine-3,5-diamine dihydrochloride
Sus scrofa
-
0.01
4-(aminomethyl)-N,N'-dibutylpyridine-3,5-diamine dihydrochloride
Sus scrofa
-
0.0025
4-(aminomethyl)-N,N'-diethylpyridine-3,5-diamine dihydrochloride
Sus scrofa
-
0.000061
4-(aminomethyl)-N,N'-dimethylpyridine-3,5-diamine dihydrochloride
Sus scrofa
-
0.00012
4-(aminomethyl)-N-methylpyridine-3,5-diamine dihydrochloride
Sus scrofa
-
additional information
additional information
Sus scrofa
above 1.0 mM for 1-(3,5-diethoxypyridin-4-yl)methanamine dihydrochloride, 3,3'-[[4-(aminomethyl)pyridine-3,5-diyl]bis(oxy)]dipropan-1-ol dihydrochloride, 4,4'-[[4-(aminomethyl)pyridine-3,5-diyl]bis(oxy)]dibutan-1-ol dihydrochloride, 1-[3-(benzyloxy)-5-ethoxypyridin-4-yl]methanamine dihydrochloride, 1-[3,5-bis(tert-butylsulfanyl)pyridin-4-yl]methanamine dihydrochloride and above 0.1 mM for 3-(1-piperidinyl)-4-aminomethylpyridine dihydrochloride hemihydrate, 2-methylaminobenzylamine dihydrochloride, and 2-ethylaminobenzylamine dihydrochloride
-
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Mondovi, B.; Costa, M.T.; Agro, A.F.; Rotilio, G.
Pyridoxal phosphate as a prosthetic group of pig kidney diamine oxidase
Arch. Biochem. Biophys.
119
373-381
1967
Sus scrofa
brenda
Floris, G.; Fadda, M.B.; Pellegrini, M.; Corda, M.; Agro, A.F.
Purification of pig kidney diamine oxidase by gel-exclusion chromatography
FEBS Lett.
72
179-181
1976
Sus scrofa
brenda
Bardsley, W.G.; Crabbe, M.J.C.; Shindler, J.S.
Kinetics of the diamine oxidase reaction
Biochem. J.
131
459-469
1973
Sus scrofa
brenda
Costa, M.T.; Rotilio, G.; Agro, A.F.; Vallogini, M.P.; Mondovi, B.
On the active site of diamine oxidase: kinetic studies
Arch. Biochem. Biophys.
147
8-13
1971
Sus scrofa
brenda
Stesina, L.N.; Akopyan, Z.I.; Gorkin, V.Z.
Modification of catalytic properties of amine oxidases
FEBS Lett.
16
349-351
1971
Sus scrofa
brenda
Stevanato, R.; Porchia, M.; Befani, O.; Mondovi, B.; Rigo, A.
Characterization of free and immobilized amine oxidases
Biotechnol. Appl. Biochem.
11
266-272
1989
Bos taurus, Sus scrofa
brenda
Bieganski, T.; Kusche, J.; Lorenz, W.; Hesterberg, R.; Stahlknecht, C.D.; Feussner, K.D.
Distribution and properties of human intestinal diamine oxidase and its relevance for the histamine catabolism
Biochim. Biophys. Acta
756
196-203
1983
Canis lupus familiaris, Cavia porcellus, Oryctolagus cuniculus, Homo sapiens, Mus musculus, Rattus norvegicus, Sus scrofa
brenda
Tamura, H.; Horiike, K.; Fukuda, H.; Watanabe, T.
Kinetic studies on the inhibition mechanism of diamine oxidase from porcine kidney by aminoguanidine
J. Biochem.
105
299-306
1989
Sus scrofa
brenda
Dooley, D.M.; Golnik, K.C.
Spectroscopic and kinetics studies of the inhibition of pig kidney diamine oxidase by anions
J. Biol. Chem.
258
4245-4248
1983
Sus scrofa
brenda
Federico, R.; Angelini, R.; Ercolini, L.; Venturini, G.; Mattevi, A.; Ascenzi, P.
Competitive inhibition of swine kidney copper amine oxidase by drugs: amiloride, clonidine, and gabexate mesylate
Biochem. Biophys. Res. Commun.
240
150-152
1997
Sus scrofa
brenda
Bertini, V.; Buffoni, F.; Ignesti, G.; Picci, N.; Trombino, S.; Iemma, F.; Alfei, S.; Pocci, M.; Lucchesini, F.; De Munno, A.
Alkylamino derivatives of 4-aminomethylpyridine as inhibitors of copper-containing amine oxidases
J. Med. Chem.
48
664-670
2005
Sus scrofa (Q9TRC7)
brenda
Mura, A.; Anedda, R.; Pintus, F.; Casu, M.; Padiglia, A.; Floris, G.; Medda, R.
An important lysine residue in copper/quinone-containing amine oxidases
FEBS J.
274
2585-2595
2007
Bos taurus, Euphorbia characias, Lens culinaris, Pisum sativum, Sus scrofa
brenda
Sebela, M.; Tylichova, M.; Pec, P.
Inhibition of diamine oxidases and polyamine oxidases by diamine-based compounds
J. Neural Transm.
114
793-798
2007
Pisum sativum, Sus scrofa
brenda
Nau, W.M.; Ghale, G.; Hennig, A.; Bakirci, H.; Bailey, D.M.
Substrate-selective supramolecular tandem assays: monitoring enzyme inhibition of arginase and diamine oxidase by fluorescent dye displacement from calixarene and cucurbituril macrocycles
J. Am. Chem. Soc.
131
11558-11570
2009
Sus scrofa
brenda
Hashimoto, T.; Mitani, A.; Yamada, Y.
Diamine oxidase from cultured roots of Hyoscyamus niger: its function in tropane alkaloid biosynthesis
Plant Physiol.
93
216-221
1990
Hyoscyamus niger, Pisum sativum, Sus scrofa
brenda
Gludovacz, E.; Maresch, D.; Lopes de Carvalho, L.; Puxbaum, V.; Baier, L.J.; Suetzl, L.; Guedez, G.; Gruenwald-Gruber, C.; Ulm, B.; Pils, S.; Ristl, R.; Altmann, F.; Jilma, B.; Salminen, T.A.; Borth, N.; Boehm, T.
Oligomannosidic glycans at Asn-110 are essential for secretion of human diamine oxidase
J. Biol. Chem.
293
1070-1087
2018
Homo sapiens (P19801), Homo sapiens, Sus scrofa (Q9TRC7)
brenda
Kettner, L.; Seitl, I.; Fischer, L.
Evaluation of porcine diamine oxidase for the conversion of histamine in food-relevant amounts
J. Food Sci.
85
843-852
2020
Sus scrofa (Q9TRC7), Sus scrofa
brenda