Protein Information

Name amine oxidase
Synonyms AOC 3; DAO; Diamine oxidase; Histaminase; Amine oxidase; AOC3; AOC3 Human placenta amine oxidase; Copper amine oxidase…

Compound Information

Name acrolein
CAS 2-propenal

Reference List

PubMed Abstract RScore(About this table)
10048142 Conklin DJ, Langford SD, Boor PJ: Contribution of serum and cellular semicarbazide-sensitive amine oxidase to amine metabolism and cardiovascular toxicity. Toxicol Sci. 1998 Dec;46(2):386-92.

Smooth muscle cells and beating cardiac myocytes were grown in 96-well plates and exposed to various concentrations and combinations of FCS in medium, amines (allylamine, AA; benzylamine, BZA; and methylamine, MA), and amine metabolites (aldehydes: acrolein, benzaldehyde, and formaldehyde; hydrogen peroxide, H2O2; ammonia, NH3).
5(0,0,0,5) Details
8068243 Averill-Bates DA, Agostinelli E, Przybytkowski E, Mondovi B: Aldehyde dehydrogenase and cytotoxicity of purified bovine serum amine oxidase and spermine in Chinese hamster ovary cells. Biochem Cell Biol. 1994 Jan-Feb;72(1-2):36-42.

It has been suggested that the dialdehyde produced during the oxidation of spermine subsequently undergoes spontaneous beta-elimination to form acrolein.
5(0,0,0,5) Details
10406932 He N, Singhal SS, Awasthi S, Zhao T, Boor PJ: Role of glutathione S-transferase 8-8 in allylamine resistance of vascular smooth muscle cells in vitro. Toxicol Appl Pharmacol. 1999 Jul 15;158(2):177-85.

AA's toxic effects are thought to be exerted through its conversion to acrolein (AC), a potent electrophilic alkylating agent and atherogen.
Semicarbazide sensitive amine oxidase (SSAO) catalyzes the oxidation of AA to AC.
4(0,0,0,4) Details
9677370 Lee Y, Sayre LM: Reaffirmation that metabolism of polyamines by bovine plasma amine oxidase occurs strictly at the primary amino termini. J Biol Chem. 1998 Jul 31;273(31):19490-4.

3(0,0,0,3) Details
10593505 Conklin DJ, Trent MB, Boor PJ: The role of plasma semicarbazide-sensitive amine oxidase in allylamine and beta-aminopropionitrile cardiovascular toxicity: mechanisms of myocardial protection and aortic medial injury in rats. Toxicology. 1999 Nov 15;138(3):137-54.

BetaAPN offered substantial protection against AA cytotoxicity in cultured vascular smooth muscle cells and beating myocytes, but did not alter the cytotoxicity of AA metabolites (i.e. acrolein, H2O2, or ammonia) in vascular smooth muscle cells as determined by the MTT viability assay.
3(0,0,0,3) Details
2842890 Ramos K, Grossman SL, Cox LR: Allylamine-induced vascular toxicity in vitro: prevention by semicarbazide-sensitive amine oxidase inhibitors. Toxicol Appl Pharmacol. 1988 Aug;95(1):61-71.

Single cell suspensions of VEC or SMC formed acrolein (ACR) when incubated in the presence of AAM.
3(0,0,0,3) Details
7945412 Agostinelli E, Przybytkowski E, Mondovi B, Averill-Bates DA: Heat enhancement of cytotoxicity induced by oxidation products of spermine in Chinese hamster ovary cells. Biochem Pharmacol. 1994 Sep 15;48(6):1181-6.

This study investigates the potential of using polyamines as thermosensitizers, in the presence of bovine serum amine oxidase (BSAO), as a new anticancer strategy.
Heat also increased the individual cytotoxicity of both exogenous H2O2 and the exogenous aldehyde acrolein.
2(0,0,0,2) Details
15863005 Houen G, Struve C, Sondergaard R, Friis T, Anthoni U, Nielsen PH, Christophersen C, Petersen BO, Duus JO: Substrate specificity of the bovine serum amine oxidase and in situ characterisation of aminoaldehydes by NMR spectroscopy. Bioorg Med Chem. 2005 Jun 1;13(11):3783-96.

No acrolein was observed at any time during the oxidation showing that it reacts very fast with available amino groups forming a variety of derivatives.
2(0,0,0,2) Details
8130014 Houen G, Bock K, Jensen AL: HPLC and NMR investigation of the serum amine oxidase catalyzed oxidation of polyamines. Acta Chem Scand. 1994 Jan;48(1):52-60.

These findings were further substantiated by analysis of the reaction products by ion-exchange chromatography and by analysis of the products formed by oxidation of polyamines by the cofactor of Cu amine oxidases, 6-hydroxydopa. 3-Aminopropanal is unstable and can give rise to acrolein by beta-elimination.
2(0,0,0,2) Details
16225993 Toninello A, Pietrangeli P, De Marchi U, Salvi M, Mondovi B: Amine oxidases in apoptosis and cancer. Biochim Biophys Acta. 2006 Jan;1765(1):1-13. Epub 2005 Sep 29.

A primary involvement of amine oxidases in cancer growth inhibition and progression, especially by means of aldehydes, H (2) O (2) and other reactive oxygen species, the amine oxidase-mediated products of biogenic amines oxidation, has been demonstrated.
The oxidation products of biogenic amines appears to be also carcinogenic, while acrolein, produced from the oxidation of spermine and spermidine, should be a key compound both carcinogenic and cytotoxic.
1(0,0,0,1) Details
17429570 Bachrach U: Antiviral activity of oxidized polyamines. Amino Acids. 2007 Aug;33(2):267-72. Epub 2007 Apr 12.

Polyamines, oxidized by serum amine oxidase, yield aminoaldehydes and hydrogen peroxide.
Acrolein may be formed from the aminoaldehydes by a spontaneous beta-elimination process.
1(0,0,0,1) Details
19639169 Agostinelli E, Condello M, Molinari A, Tempera G, Viceconte N, Arancia G: Cytotoxicity of spermine oxidation products to multidrug resistant melanoma M14 ADR2 cells: sensitization by the MDL 72527 lysosomotropic compound. Int J Oncol. 2009 Sep;35(3):485-98.

It has been confirmed that multidrug resistant (MDR) human melanoma cells are more sensitive than their wild-type counterparts to H2O2 and aldehydes, the products of bovine serum amine oxidase (BSAO)-catalyzed oxidation of spermine.
The metabolites formed by BSAO and spermine are more toxic than exogenous H2O2 and acrolein, even though their concentration is lower during the initial phase of incubation due to their more gradual release than the exogenous products.
1(0,0,0,1) Details
11543647 Conklin DJ, Boyce CL, Trent MB, Boor PJ: Amine metabolism: a novel path to coronary artery vasospasm. . Toxicol Appl Pharmacol. 2001 Sep 1;175(2):149-59.

We tested whether AA or acrolein (1, 10, 100, and 1000 microM), a highly reactive product of AA metabolism by SSAO, could contract CA or thoracic aorta (TA) in vitro and if the AA effects involved SSAO.
114(1,2,2,4) Details
10892891 Meszaros Z, Karadi I, Csanyi A, Szombathy T, Romics L, Magyar K: Determination of human serum semicarbazide-sensitive amine oxidase activity: a possible clinical marker of atherosclerosis. Eur J Drug Metab Pharmacokinet. 1999 Oct-Dec;24(4):299-302.

Some previous studies on cultured endothelial cells indicate that cytotoxic metabolites (e.g. hydrogen peroxide, formaldehyde, acrolein) formed by serum SSAO may cause endothelial injury and subsequently induce atherosclerosis.
87(1,1,1,7) Details
8920635 Lyles GA: Mammalian plasma and tissue-bound semicarbazide-sensitive amine oxidases: biochemical, pharmacological and toxicological aspects. Int J Biochem Cell Biol. 1996 Mar;28(3):259-74.

Vascular SSAO can metabolize the xenobiotic aliphatic amine, allylamine, to the cytotoxic aldehyde acrolein and this has been linked to the ability of allylamine administration to produce cardiovascular lesions in experimental animals, sometimes mimicking features of atherosclerotic disease.
85(1,1,1,5) Details
2104785 Boor PJ, Hysmith RM, Sanduja R: A role for a new vascular enzyme in the metabolism of xenobiotic amines. Circ Res. 1990 Jan;66(1):249-52.

Oxidative deamination of allylamine to a highly toxic aldehyde, acrolein, was blocked through enzyme inhibition by semicarbazide-sensitive amine oxidase suggests that this vascular enzyme's physiological role may include metabolism of exogenous amines.
82(1,1,1,2) Details
18203133 Stevens JF, Maier CS: Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease. Mol Nutr Food Res. 2008 Jan;52(1):7-25.

The main endogenous sources of acrolein are myeloperoxidase-mediated degradation of threonine and amine oxidase-mediated degradation of spermine and spermidine, which may constitute a significant source of acrolein in situations of oxidative stress and inflammation.
81(1,1,1,1) Details
12653641 Sakata K, Kashiwagi K, Sharmin S, Ueda S, Igarashi K: Acrolein produced from polyamines as one of the uraemic toxins. Biochem Soc Trans. 2003 Apr;31(2):371-4.

Among the products, we found that acrolein is a major toxic compound produced from spermine and spermidine by amine oxidase.
40(0,1,2,5) Details
16019149 Takano K, Ogura M, Yoneda Y, Nakamura Y: Oxidative metabolites are involved in polyamine-induced microglial cell death. Neuroscience. 2005;134(4):1123-31.

These results suggest that polyamine-induced apoptotic cell death of microglia is triggered by an oxidative stress with acrolein, which is produced by amine oxidase from polyamine.
38(0,1,2,3) Details
12732208 Sakata K, Kashiwagi K, Sharmin S, Ueda S, Irie Y, Murotani N, Igarashi K: Increase in putrescine, amine oxidase, and acrolein in plasma of renal failure patients. Biochem Biophys Res Commun. 2003 May 23;305(1):143-9.

Since polyamines have been suggested to be one of the uremic "toxins," the levels of each polyamine, its oxidized product, acrolein, and amine oxidase in plasma of patients with renal failure were investigated.
38(0,1,2,3) Details
8584666 Lyles GA: Substrate-specificity of mammalian tissue-bound semicarbazide-sensitive amine oxidase. Prog Brain Res. 1995;106:293-303.

Indeed, SSAO has been implicated in experimental models of cardiovascular toxicity involving conversion of the industrial aliphatic amine allylamine to acrolein.
36(0,1,1,6) Details
17095030 Conklin DJ, Bhatnagar A, Cowley HR, Johnson GH, Wiechmann RJ, Sayre LM, Trent MB, Boor PJ: Acrolein generation stimulates hypercontraction in isolated human blood vessels. Toxicol Appl Pharmacol. 2006 Dec 15;217(3):277-88. Epub 2006 Sep 29.

Isolated human CABG blood vessels (internal mammary artery, radial artery, saphenous vein) were used to determine: (1) vessel responses and sensitivity to acrolein, allylamine, and H (2) O (2) exposure (1 microM-1 mM), (2) SSAO dependence of allylamine-induced effects using SSAO inhibitors (semicarbazide, 1 mM; MDL 72274-E, active isomer; MDL 72274-Z, inactive isomer; 100 microM), (3) the vasoactive effects of two other SSAO amine substrates, benzylamine and methylamine, and (4) the contribution of extracellular Ca (2+) to hypercontraction.
32(0,1,1,2) Details
8584667 Callingham BA, Crosbie AE, Rous BA: Some aspects of the pathophysiology of semicarbazide-sensitive amine oxidase enzymes. Prog Brain Res. 1995;106:305-21.

The possibility that SSAO enzymes can convert amine substrates to highly toxic metabolites is illustrated by the production of acrolein from the xenobiotic amine, allylamine and formaldehyde and methylglyoxal from methylamine and aminoacetone, respectively.
36(0,1,1,6) Details
8430435 Awasthi S, Boor PJ: Semicarbazide protection from in vivo oxidant injury of vascular tissue by allylamine. Toxicol Lett. 1993 Feb;66(2):157-63.

Previous studies showed that allylamine-induced chronic lesions are markedly reduced by semicarbazide, an inhibitor of semicarbazide-sensitive amine oxidase (SSAO), and that allylamine is metabolized to the aldehyde, acrolein, by SSAO.
34(0,1,1,4) Details
7931255 Lyles GA: Properties of mammalian tissue-bound semicarbazide-sensitive amine oxidase: possible clues to its physiological function?. J Neural Transm Suppl. 1994;41:387-96.

Also the xenobiotic aliphatic amine allylamine produces cardiovascular damage in experimental animals by a mechanism which involves its deamination by SSAO to acrolein.
34(0,1,1,4) Details
9503571 Pino R, Lyles GA: [Effect of activity of semicarbazide-sensitive aminooxidases and cellular glutathione on the cytotoxic effect of allylamine, acrolein, and formaldehyde in human cultured endothelial cells]. Vopr Med Khim. 1997 Nov-Dec;43(6):537-47.

The ability of allylamine (AA) administration to produce vascular lesions resembling atherosclerotic disease in animals, has been linked to metabolism of AA to the toxic aldehyde acrolein (ACR) by a semicarbazide-sensitive amine oxidase (SSAO) found in plasma and in vascular smooth muscle.
33(0,1,1,3) Details
12763045 Kwak MK, Kensler TW, Casero RA Jr: Induction of phase 2 enzymes by serum oxidized polyamines through activation of Nrf2: effect of the polyamine metabolite acrolein. Biochem Biophys Res Commun. 2003 Jun 6;305(3):662-70.

The ARE from the mouse GST A1 promoter was activated about 9-fold by spermine and 5-fold by spermidine treatment, but could be inhibited by the amine oxidase inhibitor, aminoguanidine, suggesting that acrolein or hydrogen peroxide generated from polyamines by serum amine oxidase may be mediators for phase 2 enzyme induction.
32(0,1,1,2) Details
11263996 Sharmin S, Sakata K, Kashiwagi K, Ueda S, Iwasaki S, Shirahata A, Igarashi K: Polyamine cytotoxicity in the presence of bovine serum amine oxidase. . Biochem Biophys Res Commun. 2001 Mar 23;282(1):228-35.

Amine oxidase in fetal calf serum produces aminodialdehyde generating acrolein spontaneously, H (2) O (2), and ammonia from spermine.
13(0,0,2,3) Details
15843039 Tanel A, Averill-Bates DA: The aldehyde acrolein induces apoptosis via activation of the mitochondrial pathway. Biochim Biophys Acta. 2005 Apr 15;1743(3):255-67. Epub 2005 Jan 5.

Acrolein is produced by the enzymatic oxidative deamination of spermine by amine oxidase.
6(0,0,1,1) Details
7577467 Fernandez C, Sharrard RM, Talbot M, Reed BD, Monks N: Evaluation of the significance of polyamines and their oxidases in the aetiology of human cervical carcinoma. Br J Cancer. 1995 Nov;72(5):1194-9.

These amines are oxidised by polyamine oxidase (PAO) and diamine oxidase (DAO) to generate oxygen radicals and hydrogen peroxide, reactive aldehydes and acrolein, which are likely to exert local mutagenic, cytotoxic and immunosuppressive effects in vivo.
6(0,0,1,1) Details