The clinical significance of glycation

Clinical Laboratory

Volumn 45, Issue 5-6, 1999, Pages 263-273

  Thornalley, P J ^a  

^a UNIVERSITY OF ESSEX   (United Kingdom)

Author keywords

Alzheimer's disease; Diabetes; Fructosamine; Glycation; Macrovascular disease; Uraemia

Indexed keywords

CARBOHYDRATE; FRUCTOSAMINE; GLUCOSE; GLYCOSYLATED PROTEIN; GLYOXAL; METHYLGLYOXAL; NUCLEOTIDE; PHOSPHOLIPID; SCLEROPROTEIN;

ALZHEIMER DISEASE; AMYLOIDOSIS; BASEMENT MEMBRANE; CELL ACTIVATION; CONTROLLED STUDY; COVALENT BOND; CROSS LINKING; DIABETES MELLITUS; DISEASE MARKER; GLUCOSE BLOOD LEVEL; GLYCATION; HUMAN; KIDNEY FAILURE; LIPID METABOLISM; LIPID PEROXIDATION; MUTAGENESIS; RECEPTOR BINDING; REVIEW; RISK FACTOR; SMOKING; VASCULAR DISEASE;

EID: 0032980115     PISSN: 14336510     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (97)

1. Thornalley PJ: Advanced glycation and the development of diabetic complications. Unifying the involvement of glucose, methylglyoxal and oxidative stress. Endocrinol & Metabolism 1996; 3: 149-166
2. McCance DR, Dyer DG, Dunn JA, Baiue KE, Thorpe SR, Baynes JW, Lyons TJ: Maillard reaction products and their relation to complications in insulin-dependent diabetes mellitus. J Clin Invest 1993; 91: 2470-2478
3. Hou S-M, Nori P, Fang J-L, Vaca CE: Methylglyoxal induces HPRT mutation and DNA-adducts in human T-lymphocytes in vitro. Environm Molec Mutagen 1995, 26: 286-291
4. Ravandi A, Kuksis A, Marai L, Myher JJ, Steiner G, Lewisa G, Kamido H: Isolation and identification of glycated aminophospholipids from red cells and plasma of diabetic blood. FEBS Lett 1996; 381: 77-81
5. Requena JR, Ahmed MU, Fountain CW, Degenhardt TP, Reddy S, Perez C, Lyons TJ, Jenkins AJ, Baynes JW, Thorpe SR: Carboxymethylethanolamine, a biomarker of phospholipid modification during the Maillard reaction in vivo. J Biol Chem 1997; 272: 17473-17479
6. Namiki M, Hayashi T: A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation. ACS Symp Ser 1983; 215: 21-46
7. Thornalley PJ, Wolff SP, Crabbe J, Stern A: The autoxidation of glyceraldehyde and other simple monosaccharides under physiological conditions catalysed by buffer ions. Biochim Biophys Acta 1984; 797: 276-287
8. 32P-postlabelling technique for the analysis of 2′-deoxyguanosine-3′-monophosphate and DNA of methylglyoxal. Carcinogenesis 1994; 15: 1887-1894
9. 2-(1-carboxyethy1)guanine (CEG) as a guanine advanced glycosylation endproduct. Biochemistry 1995; 34: 648-655
10. Bunn HF, Higgins PJ: Reaction of monosaccharides with proteins' possible evolutionary significance. Science 1981; 213: 222-224
11. Pompliano DL, Peyman A, Knowles JR. Stabilization of a reaction intermediate as a catalytic device: Definition of the functional role of the flexible loop in triosephosphate isomerase. Biochemistry 1990; 29: 3186-3194
12. Thornalley PJ: The glyoxalase system in health and disease. Mol Aspects Med 1993; 14: 287-371
13. Takahashi M, Fujii J, Teshima T, Suzuki K, Shiba T, Taniguchi N: Identity of a major 3-deoxyglucosone-reducing enzyme with aldehyde reductase in rat liver established by amino acid sequencing and cDNA expression. Gene 1993; 127: 249-253
14. Shinohara M, Thomalley PJ, Giardino I, Beisswenger PJ, Thorpe SR, Onorato J, Brownlee M Overexpression of glyoxalase I in bovine endothelial cells inhibits intracellular advanced glycation endproduct formation and prevents hyperglycaemia-induced increases in macromolecular endocytosis. J Clin Invest 1998, 101: 1142-1147
15. Suzuki K, Koh YH, Mizuno H, Hamaoko R, Taniguchi N: Overexpression of aldehyde reductase protects PC12 cells from the cytotoxicity of methylglyoxal or 3-deoxyglucosone. J Biochem 1998; 123: 353-357
16. Thornalley PJ: Cell activation by glycated proteins. AGE receptors, receptor recognition factors and functional classification Of AGEs. Cell Molec Biol 1998; 44: 1013-1023
17. The Diabetes Control and Complications Trial Research Group: The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus New Engl J Med 1993; 327: 977-986
18. Yang C-W, Vlassara H, Peten EP, He C-J, Striker GE. Striker LJ: Advanced glycation end products up-regulate gene expression found in diabetic glomerular disease. Proc Natl Acad Sci USA 1994; 91: 9436-9440
19. Schmidt A-M, Hori O, Chen JX, Li JF, Carndall J, Zhang J, Cao R, Yan DS, Brett J, Stern D Advanced glycation endproducts interacting with their endothelial receptor induce expression of vascular cell adhesion molecule-1 (VCAM-1) in cultured human endothelial cells in mice. J Clin Invest 1995; 96: 1395-1403
20. Vlassara H, Brownlee M, Manogue KR, Dinarello CA, Pas A: Cachectin/TNF and IL-1 induced by glucose-modified proteins. Role in normal tissue remodelling Science 1988; 240: 1546-1548
21. Abordo EA, Westwood ME, Thornalley PJ: Synthesis and secretion of macrophage colony stimulating factor by mature human monocytes and human monocytic THP-1 cells induced by human serum albumin derivatives modified with methyl-glyoxal and glucose-derived advanced glycation endproducts. Immunol Lett 1996; 53: 7-13
22. Kirstein M, Brett J, Radoff S, Ogawa S, Stern D, Vlassara H: Advanced protein glycosylation induces transendothelial human monocyte chemoiaxis and secretion of PDGF: role in vascular disease of diabetes and aging. Proc Natl Acad Sci USA 1990; 87: 9010-9014
23. Kirstein M, Aston C, Hintz R, Vlassara H: Receptor-specific induction of insulin-like growth factor I (IGF-1) in human monocytes by advanced glycosylation end product-modified proteins. J Clin Invest 1992; 90: 439-446
24. Tezuka M, Koyama N, Morisaki N, Salto Y, Yoshida S, Araki N, Horiuchi S: Angiogenic effects of enhanced glycation end products of the Maillard reaction on cultured human umbilical chord vein endothelial cells. Biochem Biophys Res Com 1993; 193: 674-680
25. Yan SD, Schmidt A-M, Anderson GM, Zhang J, Brett J, Zou YS, Pinsky D, Stern D: Enhanced cellular oxidant stress by the interaction of the advanced glycation end products with their receptors/binding proteins. J Biol Chem 1994; 269: 9889-9897
26. Yamagishi S, Hsu C-C, Taniguchi M, Harada S-L, Yamamoto Y, Ohsawa K-S, Kobayashi K, Yamamoto H: Receptor-mediated toxicity to pericytes of advanced glycosylation end products. Biochem Biophys Res Com 1996; 213: 681-687
27. Lyons TJ, Silvestri G, Dunn JA, Dyer DG, Baynes JW: Role of glycation in modification of lens crystallins in diabetic and non-diabetic senile cataracts. Diabetes 1991: 40: 1010-1015
28. Vlassara H, Fuh H, Makita Z, Krungkrai S, Cerami A, Bucala R: Exogenous advanced glycosylation end products induce complex vascular dysfunction in normal animals: A model for diabetic and aging complications. Proc Natl Acad Sci USA 1992; 89: 12043-12047
29. Vitek MP, Bhattyacharya K, Glendening JM, Stopa E, Vlassara H, Bucala R, Manogue K, Cerami A: Advanced glycation end products contribute to amyloidosis in Alzheimer disease. Proc Natl Acad Sci USA 1994; 91: 4766-4770
30. 2-Microglobulin modified with advanced glycation end products is a major component of haemodialysis-associated amyloidosis. J Clin Invest 1993; 92: 1242-1252
31. Wolffenbuttel BHR, Giordano D, Founds HW, Bucala R: Long-term assessment of glucose control by haemoglobin-AGE measurement. Lancet 1996; 347: 513-515
32. Beisswenger PJ, Moore LL, Curphey TJ: Relationship between giycemic control and collagen-linked advanced glycosylation end products in type I diabetes Diabetes Care 1993; 16: 689-694
33. Salmela PI, Oikarinen AI, Ukkola O, Karajalainen A, Unnaluoto M, Puukka R, Ryhanen L: Improved metabolic control in patients with non-insulin-dependent diabetes mellitus is associated with a slower accumulation of glycation products in collagen. Eur J Clin Invest 1995; 25: 494-500
34. Beisswenger PJ, Makita Z, Curphey TJ, Moore LL, Jean S, Brinckjohnsen T, Bucala R, Vlassara H: Formation of immunochemical advanced glycosylation end-products precedes and correlates with early manifestations of renal and retinal disease in diabetes. Diabetes 1995; 44: 824-829
35. Berg TJ, Bangstad HJ, Torjesen, P.A., Osterby R, Bucala R, Hanssen KF: Advanced glycation end products in serum predict changes in the kidney morphology of patients with insulin-dependent diabetes. Metabolism-Clin Exp 1997; 46: 661-665
36. Makita Z, Radoff S, Rayfield EJ, Yang Z, Skolnik E, Delaney V, Friedman E, Cerami A, Vlassara H: Advanced glycosylation end products in patients with diabetic nephropathy. N Engl J Med 1991; 325: 836-842
37. Lee WK, Akyol M, Dominiczak MH, Briggs JD: Kidney transplantation decreases the tissue level of advanced glycosylation end-products. Nephrol Dial Transplant 1995; 10: 103-107
38. Papanastasiou P, Grass L, Rodela H, Patrikarea A, Oreopoulos D, Diamandis EP: Immunological quantification of advanced glycosylation end-products in the serum of patients on hemodialysis or CAPD. Kidney Internat 1994; 46: 216-222
39. Degenhardt TP, Grass L, Reddy S, Thorpe SR, Diamandis EP, Baynes JW: The serum concentration of the advanced glycation end-product Nε-(carboxymethyl)lysine is increased in uraemia. Kidney Internat 1997; 52: 1064-1067
40. Odani H, Shinzato T, Usami J, Matsumoto K, Brinkmann Frye E, Baynes JW, Maeda K: Imidazolium crosslinks derived from reaction of lysine with glyoxal and methylglyoxal are increased in serum proteins of uremic patients: evidence for increased oxidative stress in uremia. FEBS Lett 1998; 427: 381-385
41. Dolhofer-Bliesener R, Lechner B, Gerbitz KD. Possible significance of advanced glycation endproducts in serum in end-stage renal disease and in late complications of diabetes. Eur J Clin Chem Clin Biochem 1996; 34: 355-361
42. Lamb E, Cattell WR, Dawnay A: Glycated albumin in serum and dialysate of patients on continuous ambulatory peritoneal dialysis. Clin Sci 1993; 84: 619-626
43. Descamps-Latscha B, Herbelin A, Nguyen AT, Zingraff J, Jungers P, Chatenoud L: Immune system dysregulation in uraemia Semin Nephrol 1994; 14: 253-260
44. Sies H: "Oxidative stress" London: Academic Press, 1986
45. Abordo EA, Minhas HS, Thomalley PJ: Accumulation of α-oxoaldehydes during oxidative stress. A role in cytotoxicity Biochem Pharmacol 1999; in press
46. Linden T, Forsback G, Deppisch R, Henle T, Wseslander A: 3-Deoxyglucosone, a promoter of advanced glycation end products in fluids for peritoneal dialysis. Peritoneal Dialysis Internat 1998; 18: 290-293
47. 2-microglobulin is modified with imidazolone, a novel advanced glycation end product, in dialysis-related amyloidosis. Kidney International 1997; 51: 187-194
48. ε-(carbaoxymethyl)lysine in dialysis-related amyloidosis. Kidney Internat 1996; 50: 1301-1309
49. 2-microglobulin-containing amyloid fibrils in patients with dialysis-related amyloidosis. Proc Natl Acad Sci USA 1996; 93: 2353-2358
50. 2-Microglobulin amyloidosis. Internat J Exp Clin Invest 1997; 4: 187-211
51. 2-microglobulin in patients with hemodialysis-associated amyloidosis: identification of the glycated sites. Biochemistry 1994; 33: 12215-12221
52. 2-microglobulin modified with advanced glycation endproducts in the pathogenesis of hemodialysis-assisted amyloidosis. J Clin Invest 1994; 93: 521-528
53. Iida Y, Miyata T, Inagi R, Sugiyama S, Maeda K: β2-Microglobulin modified with advanced glycation end products induces interleukin-6 from human macrophages. Biochem Biophys Res Com 1994; 201: 1235-1241
54. Nakamura Y, Horii Y, Nishino T, Shiiki H, Sakaguchi Y, Kagoshima T, Dohi K, Makita Z, Vlassara H, Bucala R: Immunohistochemical localization of advanced glycosylation endproducts in coronary atheroma and cardiac tissue in diabetes mellitus. Amer J Pathol 1993; 143: 1649-1656
55. Kume S, Takeya M, Mon T, Araki N, Suzuki H, Horiuchi S, Kodama T, Miyaudi Y, Takahashi K: Immunohistochemical and ultrastructural detection of advanced glycation end products in atherosclerotic lesions of human aorta with a novel specific monoclonal antibody. Amer J Pathol 1995; 147: 654-667
56. Schleicher E, Wagner E, Nerlich AG: Increased accumulation of the glyoxidation product Nε-(carboxymethyl)lysine in human tissues in diabetes and aging. J Clin Invest 1997; 99: 457-468
57. Stitt A, He C, Friedman S, Scher L, Rossi P, Ong L, Founds H, Li YM, Bucala R, Vlassara H: Elevated AGE-modified ApoB in sera of euglycemic, normolipidemic patients with atherosclerosis: relationship to tissue AGEs. Molecular Medicine 1997; 3: 617-627
58. Bucala R, Makita Z, Vega G, Grundy S, Koschinsky T, Cerami A, Vlassara H: Modification of low-density-lipoprotein by advanced glycation end-products contributes to the dyslipidemia of diabetes and renal insufficiency Proc Natl Acad Sci USA 1994; 91: 9441-9445
59. Schleicher E, Olgemoller B, Schon J, Durst T, Wieland OH: Limited nonenzymatic glucosylation of low density lipoprotein does not alter its catabolism in tissue culture. Biochim Biophys Acta 1985; 846: 226-233
60. Ritthaler U, Deng Y, Zhang J, Greten J, Abel M, Sido B, Allenberg J, Otto G, Roth H, Biehaus A, Ziegler R, Schmidt A-M, Waldherr R, Wahl P, Stern DM, Nawroth PP: Expression of receptors for advanced glycation end products in peripheral occlusive vascular disease. Amer J Pathol 1995, 146: 688-694
61. Matsumoto A, Naito M, Itakura H, Ikemoto S, Asaoka H, Hayakawa H, Kanamori H, Aburatani H, Takaku F, Suzuki H, Kobari Y, Miyai T, Takahashi K, Cohen EH, Wydro R, Housman DE, Kodama T: Human macrophage scavenger receptors-Primary structure, expression, and localisation in atherosclerotic lesions. Proc Natl Acad Sci USA 1990, 87: 9133-9137
62. Westwood ME, Thomalley PJ: Induction of synthesis and secretion of interleukin 1β in the human monocytic leukaemia THP-1 cells by human serum albumins modified with methylglyoxal and advanced glycation endproducts. Immunol Lett 1996; 50: 17-21
63. O'Brien SF, Mori TA, Puddey IB, Stanton KG: Absence of increased susceptibility of LDL to oxidation in type I diabetics. Diabetes Res Clin Pract 1995; 30: 195-203
64. Bowie A, Owens D, Collins P, Johnson A, Tomkin G Glycosylated LDL is more sensitive to oxidation: implications for the diabetic patient? Atherosclerosis 1993; 102: 63-67
65. Hicks M, Delbridge L, Yue DK, Reeve TS: Catalysis of lipid peroxidation by glucose and glycosylated collagen. Biochem Biophys Res Commun 1988; 151: 649-655
66. Dickson DW, Sinicropi S, Yen S-H, Ko L-W, Mattiace LA, Bucala R, Vlassara H: Glycation and microglial reaction of lesions of Alzheimer's disease. Neurobiology of Aging 1996; 17: 733-743
67. Yan S-D, Chen X, Schmidt A-M, Brett J, Godman G, Zou Y-S, Scott CW, Caputo C, Frappier T, Smith MA, Perry G, Yen S-H, Stern D. Glycated tau protein in Alrheimer disease: A mechanism for induction of oxidant stress. Proc Natl Acad Sci USA 1994; 91: 7787-7791
68. Smith MA, Taneda S, Richey PL, Miyata S, Yan S-D, Stem D, Sayre LM, Monnier VM, Perry G. Advanced Maillard reaction end products are associated with Alzheimer disease pathology. Proc Natl Acad Sci USA 1994, 91: 5710-5714
69. Seidel R, Schuller E, Cairns N, Lubec G: Evidence against glycoxidation in patients with Alzheimer's disease. Neurosci Lett 1997; 232: 49-52
70. Tabaton M, Perry G, Smith M, Vitek M, Angelini S, Dapino D, Garibaldi S, Zaccheo D, Odetti P: Is amyloid β-protein glycated in Alzheimer's disease? Neuroreport 1997; 8: 907-909
71. Kimura T, Takamatsu J, Araki N, Goto M, Kondo A, Miyakawa T, Horiuchi S: Are advanced glycation end-products associated with amyloidosis in Alzheimer's disease? Neuroreport 1995; 6: 866-868
72. Yan SD, Chen X, Fu J, Chen M, Zhu H, Roher A, Slattery T, Zhao L, Nagashima M, Morser J, Migheli A, Nawroth P, Stern D, Schmidt A-M: RAGE and amyloid-beta peptide neurotoxicity in Alzheimer's disease. Nature 1996; 382: 685-691
73. Liu Y, Dargusch R, Schubert D: Beta amyloid toxicity does not require RAGE protein. Biochem Biophys Res Com 1997; 237: 37-40
74. Kimura T, Takamatsu J, Ikeda K, Kondo A, Miyakawa T, Horiuchi S: Accumulation of advanced glycation end products of the Maillard reaction with age in human hippocampal neurons. Neurosci Lett 1996; 208: 53-56
75. Horie K, Miyata T, Yasuda T, Takeda A, Yasuda Y, Maeda K, Sobue G, Kurokawa K, Immunochemical localization of advanced glycation end products, pentosidine, and carboxymethyl-lysine in lipofuscin pigments of Alzheimer's disease and aged neurons. Biochem Biophys Res Com 1997; 236: 327-332
76. Good PF, Werner P, Hsu A, Olanow CW, Perl DP: Evidence for neuronal oxidative damage in Alzheimer's disease. Amer J Pathol 1996, 149: 21-28
77. Kaanane A, Labuza TP. The Maillard reaction in food. In: "The Maillard reaction in Aging, Diabetes, and Nutrition." New York, ARLiss, 1989, 301-327
78. Henle T, Walter H, Klostermeyer H: Evaluation of the extent of the early Maillard-reaction in milk products by direct measurement of the Amadori-product lactuloselysine. Z Lebensm Unters Forsch 1991; 193: 119-122
79. Hayashi T, Shibamoto T: Analysis of methylglyoxal in foods and beverages. J Agric Food Chem 19S5; 33. 1090-1093
80. Nagao M, Fujita Y, Sugimura T, Kosuge T: Methylglyoxal in beverages and foods: its mutagenicity and carcinogenicity. IARC Sci Publ 1986; 70: 283-291
81. Thornalley PJ: Modification of the glyoxalase system in human red blood cells by glucose in vitro. Biochem J 1988; 254: 751-755
82. t-carboxymethyllysine: a new Maillard reaction product, in rat urine. J Agric Food Chem 1987; 35: 427-431
83. Cerami C, Hounds H, Nicholl I, Mitsuhashi T, Giordano D, Vanpatten S, Lee A, Al-Abed Y, Vlassara H, Bucala R, Cerami A: Tobacco smoke is a source of toxic reactive glycation products. Proc Natl Acad Sci USA 1997; 94: 13915-13920
84. Moree-Testa P, Saint-Jalm Y: Determination of α-dicarbonyl compounds in cigarette smoke. J Chromatogr 1981; 217: 197-208
85. Roper H, Roper S, Heyns K: N.M.R. spectroscopy of N-(1-deoxy-D-fructos-1-yl)-L-amino acids ("fructose-amino acids"). Carbohydr Res 1983; 116: 183-195
86. Ahmed MU, Thorpe SR, Baynes JW: Identification of Nε-carboxymethyl-lysine as a degradation product of fructoselysine in glycated protein. J Biol Chem 1986; 261: 4889-4894
87. Sell DR, Monnier VM: Structure elucidation of a senescence crosslink from human extracellular matrix. Implication of pentoses in the aging process. J Biol Chem 1989; 264: 21597-21602
88. Portero-Otin M, Nagaraj RH, Monnier VM: Chromatographic evidence for pyrraline formation during protein glycation in vitro and in vivo. Biochim Biophys Acta 1994; 1247: 74-80
89. Hempel SL, Wessels DA: Prostaglandin E2 synthesis after oxidant stress is dependent on cell glutathione content. Am J Physiol 1994; 266: C1392-C1399
90. Shipanova IN, Glomb MA, Nagaraj RH: Protein modification by methylglyoxal: chemical nature and synthetic mechanism of a major fluorescent adduct. Arch Biochem Biphys 1997; 344: 29-36
91. Henle T, Walter A, Haeßner R. Klostermeryer H: Detection and identification of a protein-bound imidazolone resulting from the reaction of arginine residues and methylglyoxal. Z Lebansm Unters Forsch 1994; 199: 55-58
92. α-acetyl-lysine, and bovine serum albumin. J Biol Chem 1994; 269: 32299-32305
93. c-(2-Carboxyeihyl)lysine, a product of chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Biochem J 1997; 324: 565-570
94. Hayase F, Konishi Y, Kato H: Identification of the modified structure of arginine residues in proteins with 3-deoxyglucosone, a Maillard reaction intermediate. Biosci Biotech Biochem 1995; 59: 1407-1411
95. Paul RG, Avery NC, Slatter DA, Sims TJ, Bailey AJ: Isolation and characterization of advanced glycation endproducts derived from the in vitro reaction of ribose and collagen. Biochem J 1998; 330. 1241-1248
96. Skovsted AC, Christensen M, Breinholt J, Mortensen M: Characterization of a novel AGE-compound derived from lysine and 3-deoxyglucosone. Cell Molec Biol 1998; 44: 1159-1164
97. 2-alkylguanines. Biochemistry 1969; 8: 238-245