Primary-amine oxidase explained

Primary-amine oxidase
Ec Number:1.4.3.21
Width:270

Primary-amine oxidase, also known as semicarbazide-sensitive amine oxidase (SSAO),[1] [2] is an enzyme with the systematic name primary-amine:oxygen oxidoreductase (deaminating).[3] [4] [5] [6] [7] [8] [9] [10] [11] [12] This enzyme catalyses the following chemical reaction

RCH2NH2 + H2O + O2

\rightleftharpoons

RCHO + NH3 + H2O2

These enzymes are copper quinoproteins (2,4,5-trihydroxyphenylalanine quinone).

Like monoamine oxidase (MAO), SSAO can deaminate short-chain primary amines, but is insensitive to MAO inhibitors. Semicarbazide inhibits the enzyme, in addition to other hydrazines, hydroxylamine and propargylamine. However, hydrazines are weak inhibitors and stronger inhibitors have been developed.

SSAO is found in the smooth muscle of blood vessels and various other tissues. The physiological function of SSAO is not well understood. Development of blood vessels, lipolysis regulation, and detoxication are suggested. It may function as a scavenger enzyme to assist MAO. However, the oxidation process generates harmful products that may be involved in causing atherosclerosis and vascular damage in diabetes. Elevation of SSAO activity is observed in atherosclerosis, diabetes mellitus, obesity, carotid plaque cases and varicosities.

There are SSAO inhibitors in development.[13] [14]

Human proteins containing this domain

Bacterial proteins containing this domain

Notes and References

  1. Web site: Andrew McDonald. Primary-amine oxidase. ExplorEnz – The Enzyme Database. International Union of Biochemistry and Molecular Biology. 30 December 2015.
  2. Solé M, Unzeta M . Vascular cell lines expressing SSAO/VAP-1: a new experimental tool to study its involvement in vascular diseases . Biology of the Cell . 103 . 11 . 543–57 . Nov 2011 . 21819380 . 10.1042/BC20110049 . 4598444 .
  3. Haywood GW, Large PJ . Microbial oxidation of amines. Distribution, purification and properties of two primary-amine oxidases from the yeast Candida boidinii grown on amines as sole nitrogen source . The Biochemical Journal . 199 . 1 . 187–201 . Oct 1981 . 7337701 . 1163349 . 10.1042/bj1990187.
  4. Tipping AJ, McPherson MJ . Cloning and molecular analysis of the pea seedling copper amine oxidase . The Journal of Biological Chemistry . 270 . 28 . 16939–46 . Jul 1995 . 7622512 . 10.1074/jbc.270.28.16939 . free .
  5. Lyles GA . Mammalian plasma and tissue-bound semicarbazide-sensitive amine oxidases: biochemical, pharmacological and toxicological aspects . The International Journal of Biochemistry & Cell Biology . 28 . 3 . 259–74 . Mar 1996 . 8920635 . 10.1016/1357-2725(95)00130-1 .
  6. Wilce MC, Dooley DM, Freeman HC, Guss JM, Matsunami H, McIntire WS, Ruggiero CE, Tanizawa K, Yamaguchi H . Crystal structures of the copper-containing amine oxidase from Arthrobacter globiformis in the holo and apo forms: implications for the biogenesis of topaquinone . Biochemistry . 36 . 51 . 16116–33 . Dec 1997 . 9405045 . 10.1021/bi971797i .
  7. Lee Y, Sayre LM . Reaffirmation that metabolism of polyamines by bovine plasma amine oxidase occurs strictly at the primary amino termini . The Journal of Biological Chemistry . 273 . 31 . 19490–4 . Jul 1998 . 9677370 . 10.1074/jbc.273.31.19490 . free .
  8. Houen G . Mammalian Cu-containing amine oxidases (CAOs): new methods of analysis, structural relationships, and possible functions . . 107 . S96 . 1–46 . 1999 . 10668504 . 10.1111/apm.1999.107.s96.5 . 34224347 .
  9. Andrés N, Lizcano JM, Rodríguez MJ, Romera M, Unzeta M, Mahy N . Tissue activity and cellular localization of human semicarbazide-sensitive amine oxidase . The Journal of Histochemistry and Cytochemistry . 49 . 2 . 209–17 . Feb 2001 . 11156689 . 10.1177/002215540104900208 . free .
  10. Saysell CG, Tambyrajah WS, Murray JM, Wilmot CM, Phillips SE, McPherson MJ, Knowles PF . Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue . The Biochemical Journal . 365 . Pt 3 . 809–16 . Aug 2002 . 11985492 . 1222726 . 10.1042/BJ20011435 .
  11. O'Sullivan J, Unzeta M, Healy J, O'Sullivan MI, Davey G, Tipton KF . Semicarbazide-sensitive amine oxidases: enzymes with quite a lot to do . Neurotoxicology . 25 . 1–2 . 303–15 . Jan 2004 . 14697905 . 10.1016/S0161-813X(03)00117-7 .
  12. Airenne TT, Nymalm Y, Kidron H, Smith DJ, Pihlavisto M, Salmi M, Jalkanen S, Johnson MS, Salminen TA . Crystal structure of the human vascular adhesion protein-1: unique structural features with functional implications . Protein Science . 14 . 8 . 1964–74 . Aug 2005 . 16046623 . 2279308 . 10.1110/ps.051438105 .
  13. O'Rourke AM, Wang EY, Miller A, etal. 5217225 . Anti-inflammatory effects of LJP 1586 [Z-3-fluoro-2-(4-methoxybenzyl)allylamine hydrochloride], an amine-based inhibitor of semicarbazide-sensitive amine oxidase activity . The Journal of Pharmacology and Experimental Therapeutics . 324 . 2 . 867–75 . 2008 . 17993604 . 10.1124/jpet.107.131672 .
  14. Wang EY, Gao H, Salter-Cid L, etal. Design, synthesis, and biological evaluation of semicarbazide-sensitive amine oxidase (SSAO) inhibitors with anti-inflammatory activity . Journal of Medicinal Chemistry . 49 . 7 . 2166–73 . 2006 . 16570912 . 10.1021/jm050538l .
  15. Web site: EC 1.4.3.21 – primary-amine oxidase and Organism(s) Escherichia coli, Escherichia coli K-12. BRENDA. Technische Universität Braunschweig. 8 August 2019.
  16. Elovaara H, Huusko T, Maksimow M, Elima K, Yegutkin GG, Skurnik M, Dobrindt U, Siitonen A, McPherson MJ, Salmi M, Jalkanen S . Primary Amine Oxidase of Escherichia coli Is a Metabolic Enzyme that Can Use a Human Leukocyte Molecule as a Substrate . PLOS ONE . 10 . 11 . e0142367 . 2015 . 26556595 . 4640556 . 10.1371/journal.pone.0142367 . 2015PLoSO..1042367E . free .

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