Favored and disfavored pathways of protein crosslinking by glucose: Glucose lysine dimer (GLUCOLD) and crossline versus glucosepane

Amino Acids

Volumn 40, Issue 1, 2011, Pages 167-181

  Nemet, Ina ^a   Strauch, Christopher M ^a   Monnier, Vincent M ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

Advanced glycation end product; Crosslink; Diabetes; Glycation; Maillard reaction

Indexed keywords

1,2 PHENYLENEDIAMINE; 1,3 BIS(5 AMINO 5 CARBOXYPENTYL) 4 (1',2',3',4' TETRAHYDROXYBUTYL) 3H IMIDAZOLIUM SALT; 4 GUANIDINOBUTYRIC ACID; ADVANCED GLYCATION END PRODUCT; ARGININE; DIMER; FRUCTOSE; GLUCOSE; PHOSPHATE; UNCLASSIFIED DRUG;

AMADORI REARRANGEMENT; ARTICLE; BINDING SITE; CATALYSIS; CONTROLLED STUDY; GLUCOSE OXIDATION; PRIORITY JOURNAL; PROTEIN CROSS LINKING; PROTEIN FUNCTION; PROTEIN GLYCOSYLATION; PROTEIN ISOLATION; PROTEIN STRUCTURE; SIGNAL TRANSDUCTION;

CROSS-LINKING REAGENTS; GLUCOSE; GLYCOSYLATION END PRODUCTS, ADVANCED; LYSINE; MAILLARD REACTION; PROTEINS;

EID: 78751489575     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0631-2     Document Type: Article

References (42)

1. N Ahmed PJ Thornalley 2007 Advanced glycation endproducts: what is their relevance to diabetic complications? Diabetes Obes Metab 9 233 245 1:CAS:528:DC%2BD2sXlvVSlu7s%3D 10.1111/j.1463-1326.2006.00595.x 17391149
2. N Ahmed OK Argirov HS Minhas CA Cordeiro PJ Thornalley 2002 Assay of advanced glycation endproducts (AGEs): surveying AGEs by chromatographic assay with derivatization by 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and application to Nepsilon-carboxymethyl-lysine- and Nepsilon-(1-carboxyethyl) lysine-modified albumin Biochem J 364 1 14 1:CAS:528:DC%2BD38XktFWiuro%3D 11988070
3. S Aoki G Hasegawa H Shigeta H Obayashi M Fujii F Kimura A Moriwaki N Nakamura K Ienaga K Nakamura M Kondo 2000 Crossline levels in serum and erythrocyte membrane proteins from patients with diabetic nephropathy Diabetes Res Clin Pract 48 119 125 1:CAS:528:DC%2BD3cXivVGiu7g%3D 10.1016/S0168-8227(99) 00148-5 10802149
4. KM Biemel HP Buhler O Reihl MO Lederer 2001 Identification and quantitative evaluation of the lysine-arginine crosslinks GODIC, MODIC, DODIC, and glucosepane in foods Nahrung 45 210 214 1:CAS:528:DC%2BD3MXltFartr8%3D 10.1002/1521-3803(20010601)45:3<210::AID-FOOD210>3.0.CO;2-L 11455790
5. KM Biemel O Reihl J Conrad MO Lederer 2001 Formation pathways for lysine-arginine cross-links derived from hexoses and pentoses by Maillard processes: unraveling the structure of a pentosidine precursor J Biol Chem 276 23405 23412 1:CAS:528:DC%2BD3MXltVWjsb4%3D 10.1074/jbc.M102035200 11279247
6. KM Biemel J Conrad MO Lederer 2002 Unexpected carbonyl mobility in aminoketoses: the key to major Maillard crosslinks Angew Chem Int Ed Engl 41 5 801 804 1:CAS:528:DC%2BD38XisVahs7g%3D 10.1002/1521-3773(20020301)41:5<801:: AID-ANIE801>3.0.CO;2-I 12491341
7. KM Biemel DA Friedl MO Lederer 2002 Identification and quantification of major Maillard cross-links in human serum albumin and lens protein evidence for glucosepane as the dominant compound J Biol Chem 277 24907 24915 1:CAS:528:DC%2BD38XlsVWit78%3D 10.1074/jbc.M202681200 11978796
8. E Brinkmann KJ Wells-Knecht SR Thorpe JW Baynes 1995 Characterization of an imidazolium compound formed by reaction of methylglyoxal and N.alpha.-hyppuryllysine J Chem Soc Perkin Trans 1 2817 2818 10.1039/p19950002817
9. P Chellan RH Nagaraj 1999 Protein crosslinking by the Maillard reaction: dicarbonyl-derived imidazolium crosslinks in aging and diabetes Arch Biochem Biophys 368 1 98 104 1:CAS:528:DyaK1MXksFanuro%3D 10.1006/abbi.1999.1291 10415116
10. Z Dai I Nemet W Shen VM Monnier 2007 Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine Arch Biochem Biophys 463 78 88 1:CAS:528:DC%2BD2sXmt1yhu70%3D 10.1016/j.abb.2007.03.007 17466255
11. Z Dai B Wang G Sun X Fan VE Anderson VM Monnier 2008 Identification of glucose-derived cross-linking sites in ribonuclease A J Proteome Res 7 2756 2768 1:CAS:528:DC%2BD1cXmt1ynt7Y%3D 10.1021/pr700874a 18500835
12. X Fan J Zhang M Theves C Strauch I Nemet X Liu J Qian FJ Giblin VM Monnier 2009 Mechanism of lysine oxidation in human lens crystallins during aging and in diabetes J Biol Chem 284 34618 34627 1:CAS:528:DC%2BD1MXhsFWitLbO 10.1074/jbc.M109.032094 19854833
13. EB Frye TP Degenhardt SR Thorpe JW Baynes 1998 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 18714 18719 1:CAS:528:DyaK1cXltFGrs7k%3D 10.1074/jbc.273.30.18714 9668043
14. MX Fu JR Requena AJ Jenkins TJ Lyons JW Baynes SR Thorpe 1996 The advanced glycation end product, Nepsilon-(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions J Biol Chem 271 9982 9986 1:CAS:528:DyaK28XisFGqtbs%3D 10.1074/jbc.271.33.19641 8626637
15. C Gerhardinger S Taneda MS Marion VM Monnier 1994 Isolation, purification, and characterization of an Amadori product binding protein from a Pseudomonas sp soil strain J Biol Chem 269 27297 27302 1:CAS:528: DyaK2cXmt1Cmtbs%3D 7961640
16. MA Glomb C Pfahler 2001 Amides are novel protein modifications formed by physiological sugars J Biol Chem 276 41638 41647 1:CAS:528:DC%2BD3MXosVGnsLY%3D 10.1074/jbc.M103557200 11493602
17. J Gobert MA Glomb 2009 Degradation of glucose: reinvestigation of reactive alpha-dicarbonyl compounds J Agric Food Chem 57 8591 8597 1:CAS:528:DC%2BD1MXhtVGkur7O 10.1021/jf9019085 19711949
18. A Goldin JA Beckman AM Schmidt MA Creager 2006 Advanced glycation end products: sparking the development of diabetic vascular injury Circulation 114 597 605 1:CAS:528:DC%2BD28Xns1Snu70%3D 10.1161/CIRCULATIONAHA.106.621854 16894049
19. T Kislinger C Fu B Huber W Qu A Taguchi S Du Yan M Hofmann SF Yan M Pischetsrieder D Stern AM Schmidt 1999 N(epsilon)-(carboxymethyl)lysine adducts of proteins are ligands for receptor for advanced glycation end products that activate cell signaling pathways and modulate gene expression J Biol Chem 274 31740 31749 1:CAS:528:DyaK1MXntFOjsLs%3D 10.1074/jbc.274.44.31740 10531386
20. MO Lederer RG Klaiber 1999 Cross-linking of proteins by Maillard processes: characterization and detection of lysine-arginine cross-links derived from glyoxal and methylglyoxal Bioorg Med Chem 7 2499 2507 1:CAS:528: DC%2BD3cXpsVCj 10.1016/S0968-0896(99)00212-6 10632059
21. MO Lederer F Gerum T Severin 1998 Cross-linking of proteins by Maillard processes-model reactions of d-glucose or methylglyoxal with butylamine and guanidine derivatives Bioorg Med Chem 6 993 1002 1:CAS:528:DyaK1cXlsVans7g%3D 10.1016/S0968-0896(98)00058-3 9730235
22. VM Monnier DR Sell RH Nagaraj S Miyata S Grandhee P Odetti SA Ibrahim 1992 Maillard reaction-mediated molecular damage to extracellular matrix and other tissue proteins in diabetes, aging, and uremia Diabetes 41 Suppl 2 36 41 1:CAS:528:DyaK3sXnvVSktg%3D%3D 1526333
23. R Nagai CM Hayashi L Xia M Takeya S Horiuchi 2002 Identification in human atherosclerotic lesions of GA-pyridine, a novel structure derived from glycolaldehyde-modified proteins J Biol Chem 277 48905 48912 1:CAS:528:DC%2BD38Xptlent7c%3D 10.1074/jbc.M205688200 12377783
24. RH Nagaraj VM Monnier 1992 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 34 42 1:STN:280:DyaK387nt12jsQ%3D%3D 1540622
25. RH Nagaraj IN Shipanova FM Faust 1996 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 19338 19345 1:CAS:528:DyaK28XkvFymsrk%3D 10.1074/jbc.271.32.19338 8702619
26. Nakamura K, Hasegawa T, Fukunaga Y, Ienaga K (1992) Crosslines A and B as candidates for the fluorophores in age- and diabetes-related cross-linked proteins, and their diacetates produced by Maillard reaction of N.alpha.-acetyl-lysine with glucose. J Chem Soc Chem Commun 992-994
27. K Nakamura Y Nakazawa K Ienaga 1997 Acid-stable fluorescent advanced glycation end products: vesperlysines A, B, and C are formed as crosslinked products in the Maillard reaction between lysine or proteins with glucose Biochem Biophys Res Commun 232 227 230 1:CAS:528:DyaK2sXhvVyltbg%3D 10.1006/bbrc.1997.6262 9125137
28. H Obayashi K Nakano H Shigeta M Yamaguchi K Yoshimori M Fukui M Fujii Y Kitagawa N Nakamura K Nakamura Y Nakazawa K Ienaga M Ohta M Nishimura I Fukui M Kondo 1996 Formation of crossline as a fluorescent advanced glycation end product in vitro and in vivo Biochem Biophys Res Commun 226 37 41 1:CAS:528:DyaK28XlsVKntL4%3D 10.1006/bbrc.1996.1308 8806589
29. H Odani T Shinzato J Usami Y Matsumoto E Brinkmann Frye JW Baynes K Maeda 1998 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 427 381 385 1:CAS:528: DyaK1cXjtVKitL4%3D 10.1016/S0014-5793(98)00416-5 9637262
30. O Reihl TM Rothenbacher MO Lederer W Schwack 2004 Carbohydrate carbonyl mobility-the key process in the formation of alpha-dicarbonyl intermediates Carbohydr Res 339 1609 1618 1:CAS:528:DC%2BD2cXks1Gltrc%3D 10.1016/j.carres. 2004.03.024 15183735
31. DR Sell VM Monnier 1989 Isolation, purification and partial characterization of novel fluorophores from aging human insoluble collagen-rich tissue Connect Tissue Res 19 77 92 1:STN:280:DyaK3c%2FgsVejsQ%3D%3D 10.3109/03008208909016816 2791558
32. DR Sell KM Biemel O Reihl MO Lederer CM Strauch VM Monnier 2005 Glucosepane is a major protein cross-link of the senescent human extracellular matrix relationship with diabetes J Biol Chem 280 12310 12315 1:CAS:528:DC%2BD2MXislyht7g%3D 10.1074/jbc.M500733200 15677467
33. DR Sell CM Strauch W Shen VM Monnier 2007 2-Aminoadipic acid is a marker of protein carbonyl oxidation in the aging human skin: effects of diabetes, renal failure and sepsis Biochem J 404 269 277 1:CAS:528:DC%2BD2sXlt1ejs7w%3D 10.1042/BJ20061645 17313367
34. IC Skovsted M Christensen J Breinholt SB Mortensen 1998 Characterization of a novel AGE-compound derived from lysine and 3-deoxyglucosone Cell Mol Biol (Noisy-le-grand) 44 1159 1163 1:CAS:528:DyaK1cXns1SksLw%3D
35. D Stern SD Yan SF Yan AM Schmidt 2002 Receptor for advanced glycation endproducts: a multiligand receptor magnifying cell stress in diverse pathologic settings Adv Drug Deliv Rev 54 1615 1625 1:CAS:528:DC%2BD38XovFemtL0%3D 10.1016/S0169-409X(02)00160-6 12453678
36. AL Tan JM Forbes ME Cooper 2007 AGE, RAGE, and ROS in diabetic nephropathy Semin Nephrol 27 130 143 1:CAS:528:DC%2BD2sXlt1KrtL8%3D 10.1016/j.semnephrol.2007.01.006 17418682
37. F Tessier M Obrenovich VM Monnier 1999 Structure and mechanism of formation of human lens fluorophore LM-1 relationship to vesperlysine A and the advanced Maillard reaction in aging, diabetes, and cataractogenesis J Biol Chem 274 20796 20804 1:CAS:528:DyaK1MXkvVKktbc%3D 10.1074/jbc.274.30.20796 10409619
38. PJ Thornalley A Langborg HS Minhas 1999 Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose Biochem J 344 109 116 1:CAS:528:DyaK1MXns1yjtrY%3D 10.1042/0264-6021:3440109 10548540
39. PJ Thornalley S Battah N Ahmed N Karachalias S Agalou R Babaei-Jadidi A Dawnay 2003 Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry Biochem J 375 581 592 1:CAS:528:DC%2BD3sXotlehsrc%3D 10.1042/BJ20030763 12885296
40. NG Watkins CI Neglia-Fisher DG Dyer SR Thorpe JW Baynes 1987 Effect of phosphate on the kinetics and specificity of glycation of protein J Biol Chem 262 7207 7212 1:CAS:528:DyaL2sXktVaru7k%3D 3584112
41. Wells-Knecht KJ, Brinkmann E, Baynes JW (1995) Characterization of an imidazolium salt formed from glyoxal and N.alpha.-Hypuryllysine: a model for Maillard reaction crosslinks in proteins. J Org Chem 6246-6247
42. M Yamaguchi N Nakamura K Nakano Y Kitagawa H Shigeta G Hasegawa K Ienaga K Nakamura Y Nakazawa I Fukui H Obayashi M Kondo 1998 Immunochemical quantification of crossline as a fluorescent advanced glycation endproduct in erythrocyte membrane proteins from diabetic patients with or without retinopathy Diabet Med 15 458 462 1:STN:280:DyaK1c3ptlykuw%3D%3D 10.1002/(SICI)1096- 9136(199806)15:6<458::AID-DIA601>3.0.CO;2-Q 9632118