Semicarbazide-sensitive amine oxidase in aortic smooth muscle cells mediates synthesis of a methylglyoxal-AGE: Implications for vascular complications in diabetes

Biochemical and Biophysical Research Communications

Volumn 297, Issue 4, 2002, Pages 863-869

  Mathys, Kenneth C ^a   Ponnampalam, Stephen N ^a   Padival, Simi ^a   Nagaraj, Ram H ^a  

^a CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Dicarbonyls; AGEs; Argpyrimidine; Diabetes; Maillard reaction; Methylamine; Semicarbazide; Smooth muscle cells

Indexed keywords

ACETIC ACID DERIVATIVE; ACETOACETIC ACID; ACETONE; ADVANCED GLYCATION END PRODUCT; AMINE OXIDASE (COPPER CONTAINING); AMINE OXIDASE (FLAVIN CONTAINING); ARGININE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; KETONE DERIVATIVE; METHYLGLYOXAL; PYRIMIDINE DERIVATIVE; SEMICARBAZIDE;

ANIMAL CELL; AORTA; ARTICLE; CATALYSIS; CATTLE; CELL LYSATE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIABETES MELLITUS; DIABETIC ANGIOPATHY; DRUG EFFECT; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SYNTHESIS; IMMUNOHISTOCHEMISTRY; INCUBATION TIME; MALE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; SMOOTH MUSCLE FIBER;

AMINE OXIDASE (COPPER-CONTAINING); ANIMALS; AORTA; CATTLE; CELLS, CULTURED; DIABETIC ANGIOPATHIES; GLUCOSE; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; KINETICS; MUSCLE, SMOOTH, VASCULAR; PYRUVALDEHYDE; SEMICARBAZIDES; STEREOISOMERISM;

ARMORACIA RUSTICANA; BOVINAE;

EID: 0036033536     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-291X(02)02293-3     Document Type: Article

References (55)

1. D.M. Zuo, P.H. Yu, Semicarbazide-sensitive amine oxidase and monoamine oxidase in rat brain microvessels, meninges, retina, and eye sclera, Brain Res. Bull. 33 (1994) 307-311.
2. G.A. Lyles, J. Chalmers, The metabolism of aminoacetone to methylglyoxal by semicarbazide-sensitive amine oxidase in human umbilical artery, Biochem. Pharmacol. 43 (1992) 1409-1414.
3. L. Conforti, R. Pirisino, G. Ignesti, G. Banchelli, L. Raimondi, Semicarbazide-sensitive amine oxidase activity in white adipose tissue of the insulin-deficient rat, J. Pharm. Pharmacol. 47 (1995) 420-424.
4. A. Fernandez de Arriba, D. Balsa, K.F. Tipton, M. Unzeta, Monoamine oxidase and semicarbazide-sensitive amine oxidase activities in bovine eye, J. Neural Transm. Suppl. 32 (1990) 327-330.
5. G.A. Lyles, Mammalian plasma and tissue-bound semicarbazide-sensitive amine oxidases: biochemical, pharmacological, and toxicological aspects, Int. J. Biochem. Cell Biol. 28 (1996) 259-274.
6. J.R. Blicharski, G.A. Lyles, Semicarbazide-sensitive amine oxi-dase activity in rat aortic cultured smooth muscle cells, J. Neural Transm. Suppl. 32 (1990) 337-339.
7. P.H. Yu, D.M. Zuo, B.A. Davis, Characterization of human serum and umbilical artery semicarbazide-sensitive amine oxidase (SSAO). Species heterogeneity and stereoisomeric specificity, Biochem. Pharmacol. 47 (1994) 1055-1059.
8. J. van Dijk, F. Boomsma, Stability of semicarbazide-sensitive amine oxidase in human blood and plasma, Clin. Chim. Acta 270 (1998) 189-194.
9. F. Boomsma, F.H. Derkx, A.H. van den Meiracker, A.J. Man in 't Veld, M.A. Schalekamp, Plasma semicarbazide-sensitive amine oxidase activity is elevated in diabetes mellitus and correlates with glycosylated haemoglobin, Clin. Sci. 88 (1995) 675-679.
10. G.A. Lyles, J. Chalmers, Aminoacetone metabolism by semicarbazide-sensitive amine oxidase in rat aorta, Biochem. Pharmacol. 49 (1995) 416-419.
11. P.J. Boor, M.B. Trent, G.A. Lyles, M. Tao, G.A. Ansari, Methylamine metabolism to formaldehyde by vascular semicarbazide-sensitive amine oxidase, Toxicology 73 (1992) 251-258.
12. Y. Deng, P.H. Yu, Simultaneous determination of formaldehyde and methylglyoxal in urine: involvement of semicarbazide-sensitive amine oxidase-mediated deamination in diabetic complications, J. Chromatogr. Sci. 37 (1999) 317-322.
13. S. Ray, M. Ray, Formation of methylglyoxal from aminoacetone by amine oxidase from goat plasma, J. Biol. Chem. 258 (1983) 3461-3462.
14. F. Boomsma, A.H. van den Meiracker, S. Winkel, H.J. Aanstoot, M.R. Batstra, A.J. Man in 't Veld, G.J. Bruining, Circulating semicarbazide-sensitive amine oxidase is raised both in type I (insulin-dependent), in type II (non-insulin-dependent) diabetes mellitus and even in childhood type I diabetes at first clinical diagnosis, Diabetologia 42 (1999) 233-237.
15. B.E. Hayes, D.E. Clarke, Semicarbazide-sensitive amine oxidase activity in streptozotocin diabetic rats, Res. Commun. Chem. Pathol. Pharmacol. 69 (1990) 71-83.
16. P.J. Thornalley, The glyoxalase system in health and disease, Mol. Aspects Med. 14 (1993) 287-371.
17. A.C. McLellan, P.J. Thornalley, J. Benn, P.H. Sonksen, Glyoxalase system in clinical diabetes mellitus and correlation with diabetic complications, Clin. Sci. 87 (1994) 21-29.
18. S.A. Phillips, D. Mirrlees, P.J. Thornalley, Modification of the glyoxalase system in streptozotocin-induced diabetic rats. Effect of the aldose reductase inhibitor Statil, Biochem. Pharmacol. 46 (1993) 805-811.
19. R. Natarajan, N. Gonzales, L. Xu, J.L. Nadler, Vascular smooth muscle cells exhibit increased growth in response to elevated glucose, Biochem. Biophys. Res. Commun. 187 (1992) 552-560.
20. L.A. Suzuki, M. Poot, R.G. Gerrity, K.E. Bornfeldt, Diabetes accelerates smooth muscle accumulation in lesions of atherosclerosis: lack of direct growth-promoting effects of high glucose levels, Diabetes 50 (2001) 851-860.
21. A. Okado, Y. Kawasaki, Y. Hasuike, M. Takahashi, T. Teshima, J. Fujii, N. Taniguchi, Induction of apoptotic cell death by methylglyoxal and 3-deoxyglucosone in macrophage-derived cell lines, Biochem. Biophys. Res. Commun. 225 (1996) 219-224.
22. S. Kikuchi, K. Shinpo, F. Moriwaka, Z. Makita, T. Miyata, K. Tashiro, Neurotoxicity of methylglyoxal and 3-deoxyglucosone on cultured cortical neurons: synergism between glycation and oxidative stress, possibly involved in neurodegenerative diseases, J. Neurosci. Res. 57 (1999) 280-289.
23. J. Du, H. Suzuki, F. Nagase, A.A. Akhand, T. Yokoyama, T. Miyata, K. Kurokawa, I. Nakashima, Methylglyoxal induces apoptosis in Jurkat leukemia T cells by activating c-Jun N-terminal kinase, J. Cell. Biochem. 77 (2000) 333-344.
24. V.M. Monnier, D.R. Sell, R.H. Nagaraj, S. Miyata, S. Grandhee, P. Odetti, S.A. Ibrahim, Maillard reaction-mediated molecular damage to extracellular matrix and other tissue proteins in diabetes, aging, and uremia, Diabetes 41 (1992) 36-41.
25. M. Brownlee, Negative consequences of glycation, Metabolism 49 (2000) 9-13.
26. M. Brownlee, Lilly Lecture 1993. Glycation and diabetic complications, Diabetes 43 (1994) 836-841.
27. R.H. Nagaraj, D.R. Sell, M. Prabhakaram, B.J. Ortwerth, V.M. Monnier, High correlation between pentosidine protein crosslinks and pigmentation implicates ascorbate oxidation in human lens senescence and cataractogenesis, Proc. Natl. Acad. Sci. USA. 88 (1991) 10257-10261.
28. A.W. Stitt, Advanced glycation: an important pathological event in diabetic and age related ocular disease, Br. J. Ophthalmol. 85 (2001) 746-753.
29. K.M. Biemel, H.P. Buhler, O. Reihl, M.O. Lederer, Identification and quantitative evaluation of the lysine-arginine cross-links GODIC, MODIC, DODIC, and glucosepan in foods, Nahrung 45 (2001) 210-214.
30. F.A. Shamsi, A. Partal, C. Sady, M.A. Glomb, R.H. Nagaraj, Immunological evidence for methylglyoxal-derived modifications in vivo. Determination of antigenic epitopes, J. Biol. Chem. 273 (1998) 6928-6936.
31. T. Oya, N. Hattori, Y. Mizuno, S. Miyata, S. Maeda, T. Osawa, K. Uchida, Methylglyoxal modification of protein. Chemical and immunochemical characterization of methylglyoxal-arginine adducts, J. Biol. Chem. 274 (1999) 18492-18502.
32. R.H. Nagaraj, I.N. Shipanova, F.M. Faust, Protein cross-linking by the Maillard reaction. Isolation, characterization, and in vivo detection of a lysine-lysine cross-link derived from methylglyoxal, J. Biol. Chem. 271 (1996) 19338-19345.
33. P. Chellan, R. Nagaraj, Protein crosslinking by the Maillard reaction: dicarbonyl-derived imidazolium cross-links in aging and diabetes, Arch. Biochem. Biophys. 368 (1999) 98-104.
34. E.B. Frye, T.P. Degenhardt, S.R. Thorpe, J.W. Baynes, Role of the Maillard reaction in aging of tissue proteins. Advanced glycation end product-dependent increase in imidazolium cross-links in human lens proteins, J. Biol. Chem. 273 (1998) 18714-18719.
35. M.U. Ahmed, E. Brinkmann Frye, T.P. Degenhardt, S.R. Thorpe, J.W. Baynes, N-ε-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins, Biochem. J. 324 (1997) 565-570.
36. I.N. Shipanova, M.A. Glomb, R.H. Nagaraj, Protein modification by methylglyoxal: chemical nature and synthetic mechanism of a major fluorescent adduct, Arch. Biochem. Biophys. 344 (1997) 29-36.
37. M.E. Westwood, O.K. Argirov, E.A. Abordo, P.J. Thornalley, Methylglyoxal-modified arginine residues - a signal for receptor-mediated endocytosis and degradation of proteins by monocytic THP-1 cells, Biochim. Biophys. Acta 1356 (1997) 84-94.
38. P.S. Padayatti, A.S. Ng, K. Uchida, M.A. Glomb, R.H. Nagaraj, Argpyrimidine, a blue fluorophore in human lens proteins: high levels in brunescent cataractous lenses, Invest. Ophthalmol. Vis. Sci. 42 (2001) 1299-1304.
39. P.S. Padayatti, C. Jiang, M.A. Glomb, K. Uchida, R.H. Nagaraj, High concentrations of glucose induce synthesis of argpyrimidine in retinal endothelial cells, Curr. Eye Res. 23 (2001) 106-115.
40. R. Wang, M. Kudo, M. Yokoyama, G. Asano, Roles of advanced glycation end products (AGE) and receptor for AGE on vascular smooth muscle cell growth, J. Nippon Med. Sch. 68 (2001) 472-481.
41. P.H. Yu, D.M. Zuo, Aminoguanidine inhibits semicarbazide-sensitive amine oxidase activity: implications for advanced glycation and diabetic complications, Diabetologia 40 (1997) 1243-1250.
42. P.H. Yu, Deamination of methylamine and angiopathy; toxicity of formaldehyde, oxidative stress and relevance to protein glycoxidation in diabetes, J. Neural Transm. Suppl. 52 (1998) 201-216.
43. J.D. Hepworth, in: H.E. Baumgarter (Ed.), Organic Synthesis, Collective vol. 5, John Wiley and Sons, New York, 1973, pp. 27-29.
44. F.A. Shamsi, K. Lin, C. Sady, R.H. Nagaraj, Methylglyoxal-derived modifications in lens aging and cataract formation, Invest. Ophthalmol. Vis. Sci. 39 (1998) 2355-2364.
45. S.C. Wilker, P. Chellan, B.M. Arnold, R.H. Nagaraj, Chromatographic quantification of argpyrimidine, a methylglyoxal-derived product in tissue proteins: comparison with pentosidine, Anal. Biochem. 290 (2001) 353-358.
46. Y. Deng, P.H. Yu, Assessment of the deamination of aminoacetone, an endogenous substrate for semicarbazide-sensitive amine oxidase, Anal. Biochem. 270 (1999) 97-102.
47. R.H. Nagaraj, V.M. Monnier, Isolation and characterization of a blue fluorophore from human eye lens crystallins: in vitro formation from Maillard reaction with ascorbate and ribose, Biochim. Biophys. Acta 1116 (1992) 34-42.
48. Y. Hattori, M. Suzuki, S. Hattori, K. Kasai, Vascular smooth muscle cell activation by glycated albumin (Amadori adducts), Hypertension 39 (2002) 22-28.
49. K. Iino, M. Yoshinari, M. Yamamoto, K. Kaku, Y. Doi, K. Ichikawa, M. Iwase, M. Fujishima, Effect of glycated collagen on proliferation of human smooth muscle cells in vitro, Diabetologia 39 (1996) 800-806.
50. J.L. Wautier, P.J. Guillausseau, Diabetes, advanced glycation end products and vascular disease, Vasc. Med. 3 (1998) 131-137.
51. A.M. Schmidt, O. Hori, J. Brett, S.D. Yan, J.L. Wautier, D. Stern, Cellular receptors for advanced glycation end products. Implications for induction of oxidant stress and cellular dysfunction in the pathogenesis of vascular lesions, Arterioscler. Thromb. 14 (1994) 1521-1528.
52. T. Nishikawa, D. Edelstein, X. Du, S. Yamagishi, T. Matsumura, Y. Kaneda, M. Yorek, D. Beebe, P. Oates, H. Hammes, I. Giardino, M. Brownlee, Normalizing mitochondrial superoxide production blocks three pathways of hyperglycemic damage, Nature 404 (2000) 787-790.
53. S. Kume, M. Takeya, T. Mori, N. Araki, H. Suzuki, S. Horiuchi, T. Kodama, Y. Miyauchi, K. Takahashi, Immunohistochemical and ultrastructural detection of advanced glycation end products in atherosclerotic lesions of human aorta with a novel specific monoclonal antibody, Am. J. Pathol. 147 (1995) 654-667.
54. M.O. Lederer, R.G. Klaiber, Cross-linking of proteins by Maillard processes: characterization and detection of lysine-arginine cross-links derived from glyoxal and methylglyoxal, Bioorg. Med. Chem. 7 (1999) 2499-2507.
55. K.V. Chace, R. Carubelli, R.E. Nordquist, The role of nonenzymatic glycosylation, transition metals, and free radicals in the formation of collagen aggregates, Arch. Biochem. Biophys. 288 (1991) 473-480.