Immunological Evidence that Non-carboxymethyllysine Advanced Glycation End-products Are Produced from Short Chain Sugars and Dicarbonyl Compounds in vivo

Molecular Medicine

Volumn 6, Issue 2, 2000, Pages 114-125

  Takeuchi, Masayoshi ^a   Makita, Zenji ^b,d   Bucala, Richard ^c   Suzuki, Takako ^a   Koike, Takao ^b   Kameda, Yukihiko ^a  

^a HOKURIKU UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c PICOWER INST FOR MEDICAL RESEARCH   (United States)

^d KURUME UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Dicarbonyl Compounds; Glycolaldehyde; Maillard Reaction; Methylglyoxal; Short chain Sugars

Indexed keywords

ADVANCED GLYCATION END PRODUCT; ANTIBODY; DRUG DERIVATIVE; GLYCERALDEHYDE; GLYOXAL; LYSINE; METHYLGLYOXAL; N(6) CARBOXYMETHYLLYSINE; N(6)-CARBOXYMETHYLLYSINE;

AFFINITY CHROMATOGRAPHY; ANIMAL; ARTICLE; BLOOD; CATTLE; CHEMISTRY; CHRONIC KIDNEY FAILURE; CROSS REACTION; ENZYME LINKED IMMUNOSORBENT ASSAY; GLYCATION; HUMAN; IMMUNOBLOTTING; IMMUNOLOGY; METABOLISM; NON INSULIN DEPENDENT DIABETES MELLITUS; OXIDATION REDUCTION REACTION; RABBIT; RENAL REPLACEMENT THERAPY;

ANIMALS; ANTIBODIES; CATTLE; CHROMATOGRAPHY, AFFINITY; CROSS REACTIONS; DIABETES MELLITUS, TYPE 2; ENZYME-LINKED IMMUNOSORBENT ASSAY; GLYCERALDEHYDE; GLYCOSYLATION END PRODUCTS, ADVANCED; GLYOXAL; HUMANS; IMMUNOBLOTTING; KIDNEY FAILURE, CHRONIC; LYSINE; MAILLARD REACTION; OXIDATION-REDUCTION; PYRUVALDEHYDE; RABBITS; RENAL DIALYSIS;

MLCS; MLOWN;

EID: 0034136370     PISSN: 10761551     EISSN: 15283658     Source Type: Journal    
DOI: 10.1007/BF03401779     Document Type: Article

References (26)

1. Z. Makita R. Bucala E.J. Reyfield et al. Reactive glycosylation endproducts in diabetic uremia and treatment of renal failure Lancet 1994 343 1519 1522 10.1016/S0140-6736(94)92935-1 1:STN:280:DyaK2c3ns1KktA%3D%3D 7911868
2. H. Vlassara R. Bucala L. Striker Pathogenic effects of AGEs: biochemical, biologic, and clinical implications for diabetes and aging Lab. Invest. 1994 70 138 151 1:CAS:528:DyaK2cXksFCksLg%3D 8139257
3. M. Brownlee Advanced protein glycosylation in diabetes and aging Ann. Rev. Med. 1995 46 223 234 10.1146/annurev.med.46.1.223 1:CAS:528:DyaK2MXkvFSks7g%3D 7598459
4. H. Vlassara Recent progress in advanced glycation end products and diabetic complications Diabetes 1997 46 Suppl.2 S19 S25 10.2337/diab.46.2.S19 1:CAS:528:DyaK2sXlvFKgtbs%3D 9285494
5. S.R. Thorpe J.W. Baynes Role of the Maillard reaction in diabetes mellitus and diseases of aging Drugs Aging 1996 9 69 77 10.2165/00002512-199609020-00001 1:STN:280:DyaK28vhvVSjtQ%3D%3D 8820792
6. K.J. Wells-Knecht D.V. Zyzak S.R. Litchfield S.R. Thorpe J.W. Baynes Mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose Biochemistry 1995 34 3702 3709 10.1021/bi00011a027 1:CAS:528:DyaK2MXktFenurk%3D 7893666
7. M.C. Wells-Knecht S.R. Thorpe J.W. Baynes Pathways of formation of glycoxidative products during glycation of collagen Biochemistry 1995 34 15134 15141 10.1021/bi00046a020 1:CAS:528:DyaK2MXovFOju7o%3D 7578127
8. P.J. Thornalley The glyoxalase system: new developments towards functional characterization of a metabolic pathway fundamental to biological life Biochem. J. 1990 269 1 11 10.1042/bj2690001 1:CAS:528:DyaK3cXkslens74%3D 2198020 1131522
9. P.J. Thornalley Pharmacology of methylglyoxalase: formation, modification of proteins and nucleic acids, and enzymatic detoxification- a role in pathogenesis and antiproliferative chemotherapys Gen. Pharmacol. 1996 27 565 573 10.1016/0306-3623(95)02054-3 1:CAS:528:DyaK28Xkt1ClsLo%3D 8853285
10. A.C. McLellan P.J. Thornalley J. Ben P.H. Sonksen Glyoxalase system in clinical diabetes mellitus and correlation with diabetic complication Clin. Sci. 1994 87 21 29 10.1042/cs0870021 1:STN:280:DyaK2czktVyrtQ%3D%3D 8062515
11. A.C. McLellan S.A. Phillips P.J. Thornalley The assay of methylglyoxal in biological systems by derivatization with 1,2-diamino-4,5-dimethoxybenzene Anal. Biochem. 1992 206 17 23 10.1016/S0003-2697(05)80005-3 1:CAS:528:DyaK38XlvVOmsbg%3D 1456430
12. G.M. Haik T.W. Lo P.J. Thornalley Methylglyoxal concentration and glyoxalase activities in the human lens Exp. Eye Res. 1994 59 497 500 10.1006/exer.1994.1135 1:CAS:528:DyaK2MXitFyhtbY%3D 7859825
13. M.A. Glomb V.M. Monnier Mechanism of protein modification by glyoxal and glycolaldehyde, reactive intermediates of the Maillard reaction J. Biol. Chem. 1995 270 10017 10026 10.1074/jbc.270.17.10017 1:CAS:528:DyaK2MXltlWnsrY%3D 7730303
14. M. Takeuchi Z. Makita K. Yanagisawa Y. Kameda T. Koike Detection of noncarboxy-methyllysine and carboxymethyllysine advanced glycation end products (AGE) in serum of diabetic patients Mol. Med. 1999 5 393 405 10415164 2230431 1:CAS:528:DyaK1MXlslymu70%3D 10.1007/BF03402128
15. K. Ikeda T. Higashi H. Sano et al. N-(carboxymethyl)lysine protein adduct is a major immunological epitope in proteins modified with advanced glycation end products of the Maillard reaction Biochemistry 1996 35 8075 8083 10.1021/bi9530550 1:CAS:528:DyaK28XjtF2jt7w%3D 8672512
16. M.U. Ahmed E.B. Frye T.P. Degenhardt S.R. Thorpe J.W. Baynes N-(Carboxyethyl)ly-sine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins Biochem. J. 1997 324 565 570 10.1042/bj3240565 1:CAS:528:DyaK2sXjvFGmtLc%3D 9182719 1218467
17. K.J. Wells-Knecht E. Brinkmann M.C. Wells-Knecht et al. New biomarkers of Maillard reaction damage to proteins Nephrol. Dial. Transplant. 1996 11 Suppl 5 41 47 10.1093/ndt/11.supp5.41 1:CAS:528:DyaK2sXhsFCitb0%3D 9044306
18. J.R. Requena M.-X. Fu M.U. Ahmed A.J. Jenkins T.J. Lyons S.R. Thorpe Lipoxidation products as biomarkers of oxidative damage to proteins during lipid peroxidation reactions Nephrol. Dial. Transplant. 1996 11 Suppl 5 48 53 10.1093/ndt/11.supp5.48 1:CAS:528:DyaK2sXhsFCitbo%3D 9044307
19. H. Odani T. Shinzato Y. Matsumoto J. Usami K. Maeda Increase in three α, β-dicarbonyl compound levels in human uremic plasma: specific in vivo determination of intermediates in advanced Maillard reaction Biochem. Biophys. Res. Commun. 1999 256 89 93 10.1006/bbrc.1999.0221 1:CAS:528:DyaK1MXhsVCksL0%3D 10066428
20. M.M. Anderson S.L. Hazen F.F. Hsu J.W. Heinecke Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to convert hydroxy-amino acids into glycolaldehyde, 2-hydroxypropanal, and acrolein: a mechanism for the generation of highly reactive α-hydroxy and α, β-unsaturated aldehydes by phagocytes at sites of inflammation J. Clin. Invest. 1997 99 424 432 10.1172/JCI119176 1:CAS:528:DyaK2sXhtVKksbg%3D 9022075 507815
21. F.A. Shamsi A. Partal C. Sady M.A. Glomb R.H. Nagaraj Immunological evidence for methylglyoxal-derived modifications in vivo J. Biol. Chem. 1998 273 6928 6936 10.1074/jbc.273.12.6928 1:CAS:528:DyaK1cXitVGit7Y%3D 9506998
22. K. Uchida O.T. Khor T. Oya T. Osawa Y. Yasuda T. Miyata Protein modification by a Maillard reaction intermediate methylglyoxal immunochemical detection of fluorescent 5-methylimidazolone derivatives in vivo FEBS Lett. 1997 410 313 318 10.1016/S0014-5793(97)00610-8 1:CAS:528:DyaK2sXktlCqs7s%3D 9237653
23. T. Oya N. Hattori Y. Mizuno et al. Methylglyoxal modification of protein: chemical and immunochemical characterization of methylglyoxal-arginine adducts J. Biol. Chem. 1999 274 18492 18502 10.1074/jbc.274.26.18492 1:CAS:528:DyaK1MXkt1Siur8%3D 10373458
24. E. Brinkmann 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 crosslinks in human lens proteins J. Biol. Chem. 1998 273 18714 18719 10.1074/jbc.273.30.18714
25. T.P. Degenhardt S.R. Thorpe J.W. Baynes Chemical modification of proteins by methylglyoxal Cell Mol. Biol. 1998 44 1139 1145 9846896 1:CAS:528:DyaK1cXns1SksL4%3D
26. J.W. Baynes S.R. Thorpe Role of oxidative stress in diabetic complications: a new perspective on an old paradigm Diabetes 1999 48 1 9 10.2337/diabetes.48.1.1 1:CAS:528:DyaK1MXhvV2rtA%3D%3D 9892215