Nomenclature
EC number
1.4.3.21
Systematic name
primary-amine:oxygen oxidoreductase (deaminating)
Recommended name
primary-amine oxidase
Synonyms
AGAO <11> [14,15,16,32,33]
AOC2 <24> [59]
AOC3 <2,18> (<2> the major SSAO form expressed in mouse adipocytes is
encoded by the AOC3 gene [42]) [42,59]
BAO <20> [21]
BPAO <7> [13]
BSAO <7> [25]
CAO <9,11> [32,60]
Copper amine oxidase <1,3,9,11> [32,33,37,54,60]
Cu/TPQ amine oxidase <12,15,17,23> [22]
CuAO <1> [37]
ECAO <3> [11]
GPAO <23> [22]
HPAO <10,22> [17,21]
Hansenula polymorpha amine oxidase <22> [21]
LSAO <12> [22]
MAO-N <8> [55,61]
OVAO <15> [22]
PSAO <17,21> [21,22]
RAO <24> [59]
SSAO <2,4,5,7,13,18,19,24> [20,23,24,26,27,28,29,30,34,35,36,38,39,40,41,42,43,44,45,47,48,50,51,52,53,57,58,59,62,63,65,66,67,68]
SSAO/VAP-1 <2,5> [58,62]
TPQ-containing CuAO <11> [56]
VAP-1 <2,4,5,18> [57,58,59,66,67,68]
amine oxidase, copper containing <18,24> [59]
benzylamine oxidase <20> [21]
bovine plasma amine oxidase <7> [13]
bovine serum amine oxidase <7> [25]
copper amine oxidase 1 <9> [60]
copper-containing amine oxidase <11,21> [21,56]
copper-dependent amine oxidase <5> [64]
grass pea amine oxidase <23> [22]
lentil seedling amine oxidase <12> [22]
pea seedling amine oxidase <17> [22]
quinone-containing copper amine oxidase <11> [56]
sainfoin amine oxidase <15> [22]
semicarbazide-sensitive amine oxidase <2,4,5,7,13,18,19,24> [20,24,26,29,30,31,34,35,36,38,39,40,42,43,45,47,50,52,57,58,59,62,63,65,66,67,68]
semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 <5> [44]
semicarbazide-sensitive amine oxidases <2,5> [42,53]
vascular adhesion protein 1 <4,5> [66,67]
vascular adhesion protein-1 <2,4,5,18> [42,57,58,59,62,68]
Additional information <4> (<4> VAP-1 belongs to the semicarbazide-sensitive
amine oxidases, SSAOs [68]) [68]
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References
Yamada, H.; Yasunobu, K.T.: Monoamine oxidase II. Copper, one of the prosthetic groups of plasma monamine oxidase. J. Biol. Chem., 237, 3077-3082 (1962)
Carper, W.R.; Stoddard, D.D.; Martin, D.F.: Pig liver monoamine oxidase I: isolation and characterization. Biochim. Biophys. Acta, 334, 287-296 (1974)
Falk, M.C.; Staton, A.J.; Williams, T.J.: Heterogeneity of pig plasma amine oxidase: molecular and catalytic properties of chromatographically isolated forms. Biochemistry, 22, 3746-3751 (1983)
Lindström, A.; Olsson, B.; Petterson, G.: Effect of azide on some spectral and kinetic properties of pig-plasma benzylamine oxidase. Eur. J. Biochem., 48, 237-243 (1974)
Lindström, A.; Olsson, B.; Petterson, G.: Kinetics of the interaction between pig-plasma benzylamine oxidase and hydrazine derivatives. Eur. J. Biochem., 42, 177-182 (1974)
Barker, R.; Boden, N.; Cayley, G.; Charlton, S.C.; Henson, R.; Holmes, M.C.; Kelly, I.D.; Knowles, P.F.: Properties of cupric ions in benzylamine oxidase from pig plasma as studied by magnetic-resonance and kinetic methods. Biochem. J., 177, 289-302 (1979)
Hysmith, R.M.; Boor, P.J.: Purification of benzylamine oxidase from cultured porcine aortic smooth muscle cells. Biochem. Cell Biol., 66, 821-829 (1988)
Cai, D.; Klinman, J.P.: Copper amine oxidase: heterologous expression, purification, and characterization of an active enzyme in Saccharomyces cerevisiae. Biochemistry, 33, 7647-7653 (1994)
Li, R.; Klinman, J.P.; Mathews, F.S.: Copper amine oxidase from Hansenula polymorpha: the crystal structure determined at 2.4 A resolution reveals the active conformation. Structure, 6, 293-307 (1998)
Mills, S.A.; Klinman, J.P.: Evidence against reduction of Cu2+ to Cu+ during dioxygen activation in a copper amine oxidase from Yeast. J. Am. Chem. Soc., 122, 9897-9904 (2000)
Saysell, C.G.; Tambyrajah, W.S.; Murray, J.M.; Phillips, S.V.; McPherson, M.J.; Knowles, P.F.: Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue. Biochem. J., 365, 809-816 (2002)
Mills, S.A.; Goto, Y.; Su, Q.; Plastino, J.; Klinman, J.P.: Mechanistic comparison of the cobalt-substituted and wild-type copper amine oxidase from Hansenula polymorpha. Biochemistry, 41, 10577-10584 (2002)
Lee, Y.; Ling, K.Q.; Lu, X.; Silverman, R.B.; Shepard, E.M.; Dooley, D.M.; Sayre, L.M.: 3-Pyrrolines are mechanism-based inactivators of the quinone-dependent amine oxidases but only substrates of the flavin-dependent amine oxidases. J. Am. Chem. Soc., 124, 12135-12143 (2002)
Kishishita, S.; Okajima, T.; Kim, M.; Yamaguchi, H.; Hirota, S.; Suzuki, S.; Kuroda, S.; Tanizawa, K.; Mure, M.: Role of copper ion in bacterial copper amine oxidase: spectroscopic and crystallographic studies of metal-substituted enzymes. J. Am. Chem. Soc., 125, 1041-1055 (2003)
Murakawa, T.; Okajima, T.; Kuroda, S.; Nakamoto, T.; Taki, M.; Yamamoto, Y.; Hayashi, H.; Tanizawa, K.: Quantum mechanical hydrogen tunneling in bacterial copper amine oxidase reaction. Biochem. Biophys. Res. Commun., 342, 414-423 (2006)
Okajima, T.; Kishishita, S.; Chiu, Y.C.; Murakawa, T.; Kim, M.; Yamaguchi, H.; Hirota, S.; Kuroda, S.; Tanizawa, K.: Reinvestigation of metal ion specificity for quinone cofactor biogenesis in bacterial copper amine oxidase. Biochemistry, 44, 12041-12048 (2005)
DuBois, J.L.; Klinman, J.P.: Role of a strictly conserved active site tyrosine in cofactor genesis in the copper amine oxidase from Hansenula polymorpha. Biochemistry, 45, 3178-3188 (2006)
Chiu, Y.C.; Okajima, T.; Murakawa, T.; Uchida, M.; Taki, M.; Hirota, S.; Kim, M.; Yamaguchi, H.; Kawano, Y.; Kamiya, N.; Kuroda, S.; Hayashi, H.; Yamamoto, Y.; Tanizawa, K.: Kinetic and structural studies on the catalytic role of the aspartic acid residue conserved in copper amine oxidase. Biochemistry, 45, 4105-4120 (2006)
Takahashi, K.; Klinman, J.P.: Relationship of stopped flow to steady state parameters in the dimeric copper amine oxidase from Hansenula polymorpha and the role of zinc in inhibiting activity at alternate copper-containing subunits. Biochemistry, 45, 4683-4694 (2006)
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)
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)
Longu, S.; Mura, A.; Padiglia, A.; Medda, R.; Floris, G.: Mechanism-based inactivators of plant copper/quinone containing amine oxidases. Phytochemistry, 66, 1751-1758 (2005)
Dai, X.; Ou, X.; Hao, X.; Cao, D.; Tang, Y.; Hu, Y.; Li, X.; Tang, C.: Synthetic liver X receptor agonist T0901317 inhibits semicarbazide-sensitive amine oxidase gene expression and activity in apolipoprotein E knockout mice. Acta Biochim. Biophys. Sin. (Shanghai), 40, 261-268 (2008)
Gokturk, C.; Sugimoto, H.; Blomgren, B.; Roomans, G.M.; Forsberg-Nilsson, K.; Oreland, L.; Sjoquist, M.: Macrovascular changes in mice overexpressing human semicarbazide-sensitive amine oxidase in smooth muscle cells. Am. J. Hypertens., 20, 743-750 (2007)
Di Paolo, M.L.; Pesce, C.; Lunelli, M.; Scarpa, M.; Rigo, A.: N-alkanamines as substrates to probe the hydrophobic region of bovine serum amine oxidase active site: a kinetic and spectroscopic study. Arch. Biochem. Biophys., 465, 50-60 (2007)
Wang, G.J.; Lin, S.Y.; Wu, W.C.; Hou, W.C.: DPPH radical scavenging and semicarbazide-sensitive amine oxidase inhibitory and cytotoxic activities of Taiwanofungus camphoratus (Chang-chih). Biosci. Biotechnol. Biochem., 71, 1873-1878 (2007)
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)
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)
Roessner, V.; Weber, A.; Becker, A.; Beck, G.; Frieling, H.; Bleich, S.: Decreased serum activity of semicarbazide-sensitive amine oxidase (SSAO) in patients treated with second generation antipsychotics: a link to impaired glucose metabolism?. Eur. J. Clin. Pharmacol., 63, 425-429 (2007)
Lin, S.Y.; Wang, C.C.; Lu, Y.L.; Wu, W.C.; Hou, W.C.: Antioxidant, anti-semi-carbazide-sensitive amine oxidase, and anti-hypertensive activities of geraniin isolated from Phyllanthus urinaria. Food Chem. Toxicol., 46, 2485-2492 (2008)
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)
Moore, R.H.; Spies, M.A.; Culpepper, M.B.; Murakawa, T.; Hirota, S.; Okajima, T.; Tanizawa, K.; Mure, M.: Trapping of a dopaquinone intermediate in the TPQ cofactor biogenesis in a copper-containing amine oxidase from Arthrobacter globiformis. J. Am. Chem. Soc., 129, 11524-11534 (2007)
Langley, D.B.; Brown, D.E.; Cheruzel, L.E.; Contakes, S.M.; Duff, A.P.; Hilmer, K.M.; Dooley, D.M.; Gray, H.B.; Guss, J.M.; Freeman, H.C.: Enantiomer-specific binding of ruthenium(II) molecular wires by the amine oxidase of Arthrobacter globiformis. J. Am. Chem. Soc., 130, 8069-8078 (2008)
Hernandez-Guillamon, M.; Bolea, I.; Sole, M.; Boada, M.; Tipton, K.F.; Unzeta, M.: Sodium bicarbonate enhances membrane-bound and soluble human semicarbazide-sensitive amine oxidase activity in vitro. J. Biochem., 142, 571-576 (2007)
Lee, H.I.; Kim, Y.M.; Ro, Y.T.: Purification and characterization of a copper-containing amine oxidase from Mycobacterium sp. strain JC1 DSM 3803 grown on benzylamine. J. Biochem., 144, 107-114 (2008)
Wiwanitkit, V.: Synergistic interaction between semicarbazide-sensitive amine oxidase and angiotensin-converting enzyme in diabetes: functional analysis by gene ontology. J. Diabetes Complicat., 22, 413-419 (2008)
An, Z.; Jing, W.; Liu, Y.; Zhang, W.: Hydrogen peroxide generated by copper amine oxidase is involved in abscisic acid-induced stomatal closure in Vicia faba. J. Exp. Bot., 59, 815-825 (2008)
Leonetti, F.; Capaldi, C.; Pisani, L.; Nicolotti, O.; Muncipinto, G.; Stefanachi, A.; Cellamare, S.; Caccia, C.; Carotti, A.: Solid-phase synthesis and insights into structure-activity relationships of safinamide analogues as potent and selective inhibitors of type B monoamine oxidase. J. Med. Chem., 50, 49094916 (2007)
Olivieri, A.; Tipton, K.; O’Sullivan, J.: L-lysine as a recognition molecule for the VAP-1 function of SSAO. J. Neural Transm., 114, 747-749 (2007)
O’Sullivan, J.; Davey, G.; OSullivan, M.; Tipton, K.F.: Hydrogen peroxide derived from amine oxidation mediates the interaction between aminosugars and semicarbazide-sensitive amine oxidase. J. Neural Transm., 114, 751-756 (2007)
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)
Bour, S.; Prevot, D.; Guigne, C.; Stolen, C.; Jalkanen, S.; Valet, P.; Carpene, C.: Semicarbazide-sensitive amine oxidase substrates fail to induce insulinlike effects in fat cells from AOC3 knockout mice. J. Neural Transm., 114, 829-833 (2007)
Nemcsik, J.; Szoekoe, E.; Soltesz, Z.; Fodor, E.; Toth, L.; Egresits, J.; Tabi, T.; Magyar, K.; Kiss, I.: Alteration of serum semicarbazide-sensitive amine oxidase activity in chronic renal failure. J. Neural Transm., 114, 841-843 (2007)
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)
Unzeta, M.; Sole, M.; Boada, M.; Hernandez, M.: Semicarbazide-sensitive amine oxidase (SSAO) and its possible contribution to vascular damage in Alzheimers disease. J. Neural Transm., 114, 857-862 (2007)
Vidrio, H.; Medina, M.: Hypotensive effect of hydroxylamine, an endogenous nitric oxide donor and SSAO inhibitor. J. Neural Transm., 114, 863-865 (2007)
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)
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)
Takahashi, K.; Kakuta, I.; Sugimoto, H.; Obata, T.; Oreland, L.; Kinemuchi, H.: Absence of tissue-bound semicarbazide-sensitive amine oxidase activity in carp tissues. Life Sci., 80, 1094-1099 (2007)
Jiang, Z.J.; Richardson, J.S.; Yu, P.H.: The contribution of cerebral vascular semicarbazide-sensitive amine oxidase to cerebral amyloid angiopathy in Alzheimers disease. Neuropathol. Appl. Neurobiol., 34, 194-204 (2008)
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)
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)
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)
Pirrat, P.; Smith, M.A.; Pearson, A.R.; McPherson, M.J.; Phillips, S.E.: Structure of a xenon derivative of Escherichia coli copper amine oxidase: confirmation of the proposed oxygen-entry pathway. Acta Crystallogr. Sect. F, 64, 1105-1109 (2008)
Atkin, K.E.; Reiss, R.; Turner, N.J.; Brzozowski, A.M.; Grogan, G.: Cloning, expression, purification, crystallization and preliminary X-ray diffraction analysis of variants of monoamine oxidase from Aspergillus niger. Acta Crystallogr. Sect. F, 64, 182-185 (2008)
Langley, D.B.; Trambaiolo, D.M.; Duff, A.P.; Dooley, D.M.; Freeman, H.C.; Guss, J.M.: Complexes of the copper-containing amine oxidase from Arthrobacter globiformis with the inhibitors benzylhydrazine and tranylcypromine. Acta Crystallogr. Sect. F, 64, 577-583 (2008)
Nunes, S.F.; Figueiredo, I.V.; Soares, P.J.; Costa, N.E.; Lopes, M.C.; Caramona, M.M.: Semicarbazide-sensitive amine oxidase activity and total nitrite and nitrate concentrations in serum: novel biochemical markers for type 2 diabetes?. Acta Diabetol., 46, 135-140 (2009)
Bour, S.; Caspar-Bauguil, S.; Iffiu-Soltesz, Z.; Nibbelink, M.; Cousin, B.; Miiluniemi, M.; Salmi, M.; Stolen, C.; Jalkanen, S.; Casteilla, L.; Penicaud, L.; Valet, P.; Carpene, C.: Semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 deficiency reduces leukocyte infiltration into adipose tissue and favors fat deposition. Am. J. Pathol., 174, 1075-1083 (2009)
Kaitaniemi, S.; Elovaara, H.; Groen, K.; Kidron, H.; Liukkonen, J.; Salminen, T.; Salmi, M.; Jalkanen, S.; Elima, K.: The unique substrate specificity of human AOC2, a semicarbazide-sensitive amine oxidase. Cell. Mol. Life Sci., 66, 2743-2757 (2009)
Peter, C.; Laliberte, J.; Beaudoin, J.; Labbe, S.: Copper distributed by Atxl is available to copper amine oxidase 1 in Schizosaccharomyces pombe. Eukaryot. Cell, 7, 1781-1794 (2008)
Atkin, K.E.; Reiss, R.; Koehler, V.; Bailey, K.R.; Hart, S.; Turkenburg, J.P.; Turner, N.J.; Brzozowski, A.M.; Grogan, G.: The structure of monoamine oxidase from Aspergillus niger provides a molecular context for improvements in activity obtained by directed evolution. J. Mol. Biol., 384, 12181231 (2008)
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)
Vavilova, T.; Ostrovskaya, I.; Axenova, L.; Buneeva, O.; Medvedev, A.: Monoamine oxidase and semicarbazide sensitive amine oxidase activities in normal and inflamed human dental pulp. Med. Sci. Monit., 15, BR289-BR292 (2009)
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 (2010)
Liang, G.; Choi-Sledeski, Y.M.; Poli, G.; Chen, X.; Shum, P.; Minnich, A.; Wang, Q.; Tsay, J.; Sides, K.; Cairns, J.; Stoklosa, G.; Nieduzak, T.; Zhao, Z.; Wang, J.; Vaz, R.J.: A conformationally constrained inhibitor with an enhanced potency for β-tryptase and stability against semicarbazide-sensitive amine oxidase (SSAO). Bioorg. Med. Chem. Lett., 20, 6721-6724 (2010)
Haider, N.; Hochholdinger, I.; Matyus, P.; Wobus, A.: Synthesis of ortho-functionalized 4-aminomethylpyridazines as substrate-like semicarbazide-sensitive amine oxidase inhibitors. Chem. Pharm. Bull., 58, 964-970 (2010)
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)
Nurminen, E.M.; Pihlavisto, M.; Lazar, L.; Szakonyi, Z.; Pentikaeinen, U.; Fueloep, F.; Pentikaeinen, O.T.: Synthesis, in vitro activity, and three-dimensional quantitative structure-activity relationship of novel hydrazine inhibitors of human vascular adhesion protein-1. J. Med. Chem., 53, 63016315 (2010)
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Schomburg, D., Schomburg, I. (2013). primary-amine oxidase 1.4.3.21. In: Schomburg, D., Schomburg, I. (eds) Class 1 Oxidoreductases. Springer Handbook of Enzymes. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-36265-1_51
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