Physiological and pathological implications of semicarbazide-sensitive amine oxidase

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1647, Issue 1-2, 2003, Pages 193-199

  Yu, Peter H ^a   Wright, Shannon ^a   Fan, Ellen H ^a   Lun, Zhao Rong ^a   Gubisne Harberle, Diana ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Diabetes; Formaldehyde; Methylamine; Methylglyoxal; SSAO; VAP 1

Indexed keywords

ALDEHYDE; AMINE OXIDASE (COPPER CONTAINING); AMINOACETONITRILE; AMINOGUANIDINE; AMMONIA; CARBON 14; FORMALDEHYDE; HYDROGEN PEROXIDE; METHYLAMINE; METHYLGLYOXAL; VASCULAR ADHESION PROTEIN 1; ACETONE; AMINOACETONE; AOC3 PROTEIN, HUMAN; CELL ADHESION MOLECULE; DRUG DERIVATIVE; GLUCOSE; SEMICARBAZIDE DERIVATIVE;

ADIPOSE TISSUE CELL; ALZHEIMER DISEASE; ATHEROGENESIS; CATALYSIS; CHOLESTEROL DIET; CONFERENCE PAPER; DEAMINATION; DIABETES MELLITUS; ENDOTHELIUM INJURY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; GLUCOSE TRANSPORT; GLYCATION; LEUKOCYTE MIGRATION; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN CROSS LINKING; PROTEIN SYNTHESIS REGULATION; STREPTOZOCIN DIABETES; VASCULAR DISEASE; ADIPOCYTE; ANIMAL; BLOOD; HUMAN; INFLAMMATION; METABOLISM; OXIDATION REDUCTION REACTION; PHYSIOLOGY; REVIEW;

ANIMALIA; RODENTIA;

ACETONE; ADIPOCYTES; AMINE OXIDASE (COPPER-CONTAINING); ANIMALS; CATALYSIS; CELL ADHESION MOLECULES; DEAMINATION; FORMALDEHYDE; GLUCOSE; HUMANS; HYDROGEN PEROXIDE; INFLAMMATION; METHYLAMINES; OXIDATION-REDUCTION; SEMICARBAZIDES;

EID: 0038549049     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1570-9639(03)00101-8     Document Type: Conference Paper

References (90)

1. Callingham B.A., Crosbie A.E., Rous B.A. Some aspects of the pathophysiology of semicarbazide-sensitive amine oxidase enzymes. Yu P.H., Tipton K.F., Boulton A.A. Current Neurochemical and Pharmacological Aspects of Biogenic Amines: Their Function, Oxidative Deamination and Inhibition. 1995;305-321 Elsevier, Amsterdam.
2. Elliott J., Callingham B.A., Sharman D.F. The influence of amine metabolizing enzymes on the pharmacology of tyramine in the isolated perfused mesenteric arterial bed of rat. Br. J. Pharmacol. 98:1989;515-522.
3. Enrique-Tarancon G., Marti L., Morin N., Lizcano J.M., Unzeta M., Sevilla L., Camps M., Palacin M., Testar X., Carpene C., Zorzano A. Role of semicarbazide-sensitive amine oxidase on glucose transport and GLUT4 recruitment to the cell surface in adipose cells. J. Biol. Chem. 273:1998;8025-8032.
4. Salmi M., Hellman J., Jalkanen S. The role of two distinct endothelial molecules, vascular adhesion protein-1 and peripheral lymph node addressin, in the binding of lymphocyte subsets to human lymph nodes. J. Immunol. 160:1998;5629-5636.
5. Langford S.D., Trent M.B., Balakumaran A., Boor P.J. Developmental vasculotoxicity associated with inhibition of semicarbazide-sensitive amine oxidase. Toxicol. Appl. Pharmacol. 155:1999;237-244.
6. Tryding N., Nilsson S.E., Tufvesson G., Berg R., Carlstrom S., Elmfors B., Nilsson J.E. Physiological and pathological influences on serum monoamine oxidase level. Scand. J. Clin. Lab. Invest. 23:1969;79-84.
7. Nilsson S.E., Tryding N., Tufvesson G. Serum monoamine oxidase in diabetes mellitus and some other internal diseases. Acta Med. Scand. 184:1968;105-108.
8. Yuen C.T., Easton D., Misch K., Rhodes E.L. Increased activity of serum amine oxidase in granuloma annulare, necrobiosis lipoidics and diabetes. Br. J. Dermatol. 11:1987;643-649.
9. Boomsma F., Derks F.H.M., van den Meiracker A.H., Man in'tVeld A., Schalekamp M.A.D.H. Plasma semicarbazide-sensitive amine oxidase activity is elevated in diabetes mellitus and correlates with glycosylated haemoglobin. Clin. Sci. 88:1995;675-679.
10. Garpenstrand H., Ekblom J., Backlund L.B., Oreland L., Rosenqvist U. Elevated plasma semicarbazide-sensitive amine oxidase (SSAO) activity in Type 2 diabetes mellitus complicated by retinopathy. Diabet. Med. 16:1999;514-521.
11. Mészáros Z., Szombathy T., Raimondi L., Karadi I., Romics L., Magyar K. Elevated serum semicarbazide-sensitive amine oxidase activity in non-insulin-dependent diabetes mellitus: correlation with BMI and serum triglyceride. Metab. Clin. Exp. 48:1999;113-117.
12. Boomsma F., van Veldhuisen D.J., de Kam P.J., in't Veld A.J.M., Mosterd A., Lie K.I., Schalekamp M.A.D.H. Plasma semicarbazide-sensitive amine oxidase is elevated in patients with congestive heart failure. Cardiovasc. Res. 33:1997;387-391.
13. Ishizaki F. Plasma benzylamine oxidase activity in cerebrovascular disease. Eur. Neurol. 30:1990;104-107.
14. Yu P.H. Deamination of methylamine and angiopathy; toxicity of formaldehyde, oxidative stress and relevance to protein glycoxidation in diabetes. J. Neural Transm., Suppl. 52:1996;201-216.
15. Precious E., Gunn C.E., Lyles G.A. Deamination of methylamine by semicarbazide-sensitive amine oxidase in human umbilical artery and rat aorta. Biochem. Pharmacol. 37:1988;707-713.
16. Yu P.H. Oxidative deamination of aliphatic amines by rat aorta semicarbazide-sensitive amine oxidase. J. Pharm. Pharmacol. 42:1990;882-884.
17. Boor P.J., Trent M.B., Lyles G.A., Tao M., Ansari G.A.S. Methylamine metabolism to formaldehyde by vascular semicarbazide-sensitive amine oxidase. Toxicology. 73:1992;251-258.
18. Kalapos N.P., Garzo T., Antoni F., Mardl S. Accumulation of S-D-lactolylglutathione and transient decrease of glutathione level caused by methylglyoxal load in isolated hepatocytes. Biochim. Biophys. Acta. 1135:1992;159-164.
19. Lyles G.A., Chalmers J. The metabolism of aminoacetone to methylglyoxal by semicarbazide-sensitive amine oxidase in human umbilical artery. Biochem. Pharmacol. 31:1992;1417-1424.
20. Lyles G.A. Substrate-specificity of mammalian tissue-bound semicarbazide-sensitive amine oxidase. Prog. Brain Res. 106:1995;293-303.
21. Blau K. Chromatographic methods for the study of amines from biological material. Biochem. J. 80:1961;193-200.
22. Yu P.H., Dyck R.F. Impairment of methylamine clearance in uremic patients and its nephropathological implications. Clin. Nephrol. 49:1998;299-302.
23. Asatoor A.M., Kerr D.N.S. Amines in blood and urine in relation to liver disease. Clin. Chim. Acta. 6:1961;149-156.
24. Baba S., Watanabe Y., Gejyo F., Arakwa M. High-performance liquid chromatographic determination of serum aliphatic amines in chronic renal failure. Clin. Chim. Acta. 136:1984;49-56.
25. Smith A.D., Jepson J.B. Chromatography of urinary and tissue amines and amino alcohols as 2,4-dinitrophenyl derivatives prepared with 2-nitrobenzene-sulfonic acid. Anal. Biochem. 18:1967;36-45.
26. Nixon R. Volatile amines in mouse brain: a radioassay with picogram sensitivity. Anal. Biochem. 48:1972;460-470.
27. Lyles G.A., McDougall S.A. The enhanced daily excretion of urinary methylamine in rats treated with semicarbazide or hydralazine may be related to the inhibition of semicarbazide-sensitive amine oxidase activities. J. Pharm. Pharmacol. 41:1989;97-100.
28. Schayer R.W., Smiley L.R., Kaplan H.E. The metabolism of epinephrine containing isotopic carbon. J. Biol. Chem. 198:1952;545-551.
29. Dar M.S., Morselli P.L., Bowman E.R. The enzymatic systems involved in the mammalian metabolism of methylamine. Gen. Pharmacol. 16:1985;557-560.
30. Yu P.H., Lai C.T., Zuo D.M. Formation of formaldehyde from adrenaline in vivo; a potential risk factor endothelial damage. Neurochem. Res. 22:1997;615-620.
31. Jones J.D., Burnett P.C. Creatinine metabolism and toxicity. Kidney Int. 7:1975;S294-S298.
32. Yu P.H., Deng Y.L. Potential cytotoxic effect of chronic administration of creatine, a nutrition supplement to augment athletic performance. Med. Hypotheses. 54:1999;726-728.
33. Zeisel S.H., Wishnok J.S., Blusztajn J.K. Formation of methylamines from ingested choline and lecithin. J. Pharmacol. Exp. Ther. 225:1983;320-324.
34. US Dept Health and Human Services, Constituents of tobacco smoke, USPHS Publication No. 82-50179 (1982) 322.
35. Yu P.H., Zuo D.M. Aminoguanidine inhibits semicarbazide-sensitive amine oxidase activity; implication for advanced glycation and angiopathy in diabetes. Diabetologia. 363:1997;1243-1250.
36. Yu P.H., Zuo D.M. Formaldehyde produced endogenously via deamination of methylamine; a potential risk factor for initiation of endothelial injury. Atherosclerosis. 120:1996;189-197.
37. Bird M.I., Nunn P.B., Lord L.A.J. Formation of glycine and aminoacetone from L-threonine by rat liver mitochondria. Biochim. Biophys. Acta. 802:1984;229-236.
38. Deng Y.L., Yu P.H. Assessment of the deamination of aminoacetone, an endogenous substrate for semicarbazide-sensitive amine oxidase. Anal. Biochem. 270:1999;97-102.
39. Thornalley P.J. Methylglyoxal, glyoxalases and the development of diabetic complications. Amino Acids. 6:1994;15-23.
40. Westwood E.W., McLellan A.C., Thornalley P.J. Receptor-mediated endocytic uptake of methylglyoxal-modified serum albumin. J. Biol. Chem. 269:1994;32293-32298.
41. Bolt H.M. Experimental toxicology of formaldehyde. J. Cancer Res. Clin. Oncol. 13:1987;305-309.
42. Heck H.D., Casanova M., Starr T.B. Formaldehyde toxicity - new understanding. Toxicology. 20:1990;397-426.
43. Gibson J.E. Formaldehyde Toxicity. 1983;Hemisphere Publ. Washington.
44. Cooper J.R., Kini M.M. Editorial biochemical aspects of methanol poisoning. Biochem. Pharmacol. 11:1962;405-416.
45. Tsuboi S., Kawase M., Takaka A., Hirmatus M., Wada Y., Kawakami Y., Ikeka M., Ohmori S. Purification and characterization of formaldehyde dehydrogenase from rat liver cytosol. J. Biochem. 111:1992;465-471.
46. 14C]-formaldehyde in the rat nasal mucosa. Toxicol. Appl. Pharmacol. 89:1987;123-130.
47. Helander A., Tottmar O. Metabolism of biogenic aldehydes in isolated human blood cells, platelets and in plasma. Biochem. Pharmacol. 36:1987;1077-1082.
48. Malorny G.N., Rietbrock N., Schneider M. The oxidation of formaldehyde to formic acid in the blood and contribution to the metabolism of formaldehyde. Naunyn-Schmiedeberg's Arch. Exp. Pathol. Pharmakol. 250:1965;419-436.
49. Egyud L.G., Szent-Gyorgyi A. Cancer static action of methylglyoxal. Science. 160:1968;1140.
50. Nagaraj R.H., Shipanova I.N., Faust F.M. Protein cross-linking by the Mailard reaction. Isolation, characterization and in vivo detection of a lysine-lysine cross-link derived from methylglyoxal. J. Biol. Chem. 271:1996;19338-19345.
51. Sies H. Oxidative Stress; Oxidants and Antioxidants. 1991;Academic Press, London.
52. Lichszteld K., Kruk L. Singlet molecular oxygen in formaldehyde oxidation. Z. Phys. Chem. (N. F.). 108:1977;167-172.
53. Trézl L., Pipek J. Formation of exited formaldehyde in model reactions simulating real biological system. J. Mol. Struct. 170:1988;213-223.
54. Boor P.J., Hysmith R.M. Allylamine cardiovascular toxicity. Toxicology. 44:1987;129-144.
55. Nelson T.J., Boor P.J. Allylamine cardiotoxicity: IV. Metabolism to acrolein by cardiovascular tissues. Biochem. Pharmacol. 31:1982;509-514.
56. Boor P.J., Nelson T.J. Allylamine cardiotoxicity: III. Protection by semicarbazide and in vivo derangements of monoamine oxidase. Toxicology. 18:1980;87-102.
57. Yu P.H., Zuo D.M. Methylamine, a potential endogenous toxin for vascular tissues: formation of formaldehyde via enzymatic deamination and the cytotoxic effects on endothelial cells. Diabetes. 42:1993;594-603.
58. Hayes B.E., Clarke D.E. Semicarbazide-sensitive amine oxidase activity in streptozotocin diabetic rats. Res. Commun. Chem. Pathol. Pharmacol. 69:1990;71-83.
59. Elliott J., Fowden A.L., Callingham B.A., Sharman D.F., Silver M. Physiological and pathological influences on sheep blood plasma amine oxidase: effect of pregnancy and experimental alloxan-induced diabetes mellitus. Res. Vet. Sci. 50:1991;334-339.
60. Breslow J.L. Mouse models of atherosclerosis. Science. 272:1996;685-688.
61. Ross R. The pathogenesis of atherosclerosis - an update. N. Engl. J. Med. 314:1986;488-500.
62. Ross R., Harker L. Hyperlipidemia and atherosclerosis; chronic hyperlipidemia initiates and maintains lesion by endothelial cell desquamation and lipid accumulation. Science. 193:1976;1094-1100.
63. Sanders M. Molecular and cellular concepts in atherosclerosis. Pharmacol. Ther. 61:1994;109153.
64. Paigen B., Morrow A., Brandon C., Mitchell D., Holmes P.A. Variation in susceptibility to atherosclerosis among inbred strains of mice. Atherosclerosis. 57:1985;65-73.
65. Paigen B., Ishida B.Y., Verstuyft J., Winter R.B., Albee D. Atherosclerosis susceptibility differences among progenitors of recombinant inbred strains of mice. Arteriosclerosis. 10:1990;316-323.
66. Yu P.H., Deng Y.L. Endogenous formaldehyde and vulnerability of atherosclerosis: involvement of semicarbazide-sensitive amine oxidase-mediated methylamine turnover. Atherosclerosis. 140:1999;357-363.
67. Yu P.H., Wang M., Deng Y.L., Fan H., Shira-Bock L. Effect of semicarbazide-sensitive amine oxidase inhibitor on atherogenesis in KKAy diabetic mice fed with high cholesterol diet. Diabetologia. 45:2002;1255-1262.
68. Wibo M., Duong A.T., Godfraind T. Subcellular location of semicarbazide-sensitive amine oxidase in rat aorta. Eur. J. Biochem. 112:1980;87-94.
69. Lewinsohn R. Amine oxidase in human blood vessels and non-vascular smooth muscle. J. Pharm. Pharmacol. 33:1981;569-575.
70. Lyles G.A., Singh I. Vascular smooth muscle cells: a major source of the semicarbazide-sensitive amine oxidase of the rat aorta. J. Pharm. Pharmacol. 37:1985;637-643.
71. Zuo D.M., Yu P.H. Semicarbazide-sensitive amine oxidase and monoamine oxidase in rat brain microvessels, meninges, retina and eye sclera. Brain Res. Bull. 33:1994;307-311.
72. Lyles G.A., Bertie K.H. Properties of a semicarbazide-sensitive amine oxidase in rat articular cartilage. Pharmacol. Toxicol. (Suppl.). 1:1987;33.
73. Kurkijarvi R., Adams D.H., Leino R., Mottonen T., Jalkanen S., Salmi M. Circulating form of human vascular adhesion protein-1 (VAP-1): increased serum levels in inflammatory liver diseases. J. Immunol. 161:1998;1549-1557.
74. McLellan A.C., Phillips S.A., Thornalley P.J. The assay of methylglyoxal in biological systems by derivatization with diamno-4,5-dimethoxybenzene. Anal. Biochem. 206:1992;17-23.
75. Lo T.W.C., Westwood M.E., McLellan A.C., Selwood T., Thornalley P.J. Binding and modification of proteins by methylglyoxal under physiological conditions. J. Biol. Chem. 269:1994;32299-32305.
76. Lo T.W.C., Selwood T., Thornalley P.J. The reaction of methylglyoxal with aminoguanidine under physiological conditions and prevention of methylglyoxal binding to plasma proteins. Biochem. Pharmacol. 48:1994;1865-1870.
77. McLellan A.C., Thornalley P.J., Benn J., Sonksen P.H. Glyoxalase system in clinical diabetes mellitus and correlation with diabetic complications. Clin. Sci. Colch. 87:1994;21-29.
78. Yu P.H. Increase of formation of methylamine and formaldehyde in vivo after administration of nicotine and potential cytotoxicity. Neurochem. Res. 23:1998;1207-1212.
79. Morris N.J., Durett A., Aebersold R., Ross S.A., Keller S.R., Lienhard G.E. Membrane amine oxidase cloning and identification as a major protein in the adipocyte plasma membrane. J. Biol. Chem. 272:1997;9388-9392.
80. Zhang X., McIntire W.S. Cloning and sequencing of a copper-containing, topa quinone-containing monoamine oxidase from human placenta. Gene. 179:1996;279-286.
81. Smith D.J., Salmi M., Bono P., Hellman J., Leu T., Jalkanen S. Cloning of vascular adhesion protein-1; reveals a novel multifunctional adhesion molecule. J. Exp. Med. 188:1998;17-27.
82. Salmi M., Jalkanen S. VAP-1: an adhesin and an enzyme. Trends Immunol. 22:2001;211-216.
83. Tohka S., Laukkanen M., Jalkanen S., Salmi M. Vascular adhesion protein-1 (VAP-1) functions as a molecular brake during granulocyte rolling and mediates recruitment in vivo. FASEB J. 15:2001;373-382.
84. Fontana E., Boucher J., Marti L., Lizcano J.M., Testar X., Zorzano A., Carpene C. Amine oxidase substrates mimic several of the insulin effects on adipocyte differentiation in 3T3 F442A cells. Biochem. J. 356:2001;769-777.
85. Enrique-Tarancon G., Castan I., Morin N., Marti L., Abella A., Camps M., Casamitjana R., Palacin M., Testar X., Degerman E., Carpene C., Zorzano A. Substrates of semicarbazide-sensitive amine oxidase co-operate with vanadate to stimulate tyrosine phosphorylation of insulin-receptor-substrate proteins, phosphoinositide 3-kinase activity and GLUT4 translocation in adipose cells. Biochem. J. 350:2000;171-180.
86. Morin N., Lizcano J.M., Fontana E., Marti L., Smih F., Rouet P., Prevot D., Zorzano A., Unzeta M., Carpene C. Semicarbazide-sensitive amine oxidase substrates stimulate glucose transport and inhibit lipolysis in human adipocytes. J. Pharmacol. Exp. Ther. 297:2001;563-572.
87. Mercier N., Moldes M., El-Hadri K., Feve B. Semicarbazide-sensitive amine oxidase activation promotes adipose conversion of 3T3-L1 cells. Biochem. J. 358:2001;335-342.
88. Morin N., Lizcano J.M., Fontana E., Marti L., Smih F., Rouet P., Prevot D., Zorzano A., Unzeta M., Carpene C. Semicarbazide-sensitive amine oxidase substrates stimulate glucose transport and inhibit lipolysis in human adipocytes. J. Pharmacol. Exp. Ther. 297:2001;563-572.
89. El-Hadri K., Moldes M., Mercier N., Andreani M., Pairault J., Feve B. Semicarbazide-sensitive amine oxidase in vascular smooth muscle cells: differentiation-dependent expression and role in glucose uptake. Arterioscler. Thromb. Vasc. Biol. 22:2002;89-94.
90. Marti L., Abella A., Carpene C., Palacin M., Testar X., Zorzano A. Combined treatment with benzylamine and low dosages of vanadate enhances glucose tolerance and reduces hyperglycemia in streptozotocin-induced diabetic rats. Diabetes. 50:2001;2061-2068.