Characterization of advanced glycation end products for biochemical studies: Side chain modifications and fluorescence characteristics

Analytical Biochemistry

Volumn 338, Issue 2, 2005, Pages 201-215

  Schmitt, Annett ^a   Schmitt, Johannes ^b   Münch, Gerald ^c   Gasic Milencovic, Jovana ^a  

^a UNIVERSITY HOSPITAL LEIPZIG   (Germany)

^b NIMBUS Biotechnologie GmbH   (Germany)

^c JAMES COOK UNIVERSITY   (Australia)

Author keywords

Advanced glycation end products; AGE characterization; Fluorescence; Side chain modifications

Indexed keywords

AMINO ACIDS; GLYCOSYLATION; PROTEINS;

ADVANCED GLYCATION END PRODUCTS; CARBOXYMETHYL LYSINES; CONFORMATIONAL CHANGE; DEGREE OF MODIFICATION; FLUORESCENCE CHARACTERISTICS; HUMAN SERUM ALBUMINS; MODIFIER CONCENTRATION; SIDE CHAIN MODIFICATIONS;

FLUORESCENCE;

ADVANCED GLYCATION END PRODUCT; ARGININE; CARBOXYMETHYLLYSINE; GLUCOSE; GLYOXAL DERIVATIVE; GLYOXYLIC ACID; HUMAN SERUM ALBUMIN; LYSINE; LYSINE DERIVATIVE; METHYLGLYOXAL; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; BIOCHEMISTRY; CONFORMATION; FLUORESCENCE; PRIORITY JOURNAL; PROTEIN MODIFICATION;

EID: 14644397841     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ab.2004.12.003     Document Type: Article

References (35)

1. R. Bucala, Z. Makita, G. Vega, S. Grundy, T. Koschinsky, A. Cerami, and H. Vlassara Modification of low density lipoprotein by advanced glycation end products contributes to the dyslipidemia of diabetes and renal insufficiency Proc. Natl. Acad. Sci. USA 91 1994 9441 9445
2. M.P. Vitek, K. Bhattacharya, J.M. Glendening, E. Stopa, H. Vlassara, R. Bucala, K. Manogue, and A. Cerami Advanced glycation end products contribute to amyloidosis in Alzheimer disease Proc. Natl. Acad. Sci. USA 91 1994 4766 4770
3. J.V. Valencia, S.C. Weldon, D. Quinn, G.H. Kiers, J. DeGroot, J.M. TeKoppele, and T.E. Hughes Advanced glycation end product ligands for the receptor for advanced glycation end products: biochemical characterization and formation kinetics Anal. Biochem. 324 2004 68 78
4. A.J. Furth Methods for assaying nonenzymatic glycosylation Anal. Biochem. 175 1988 347 360
5. S.D. Sharma, B.N. Pandey, K.P. Mishra, and S. Sivakami Amadori product and AGE formation during nonenzymatic glycosylation of bovine serum albumin in vitro J. Biochem. Mol. Biol. Biophys. 6 2002 233 242
6. N. Ahmed, O.K. Argirov, H.S. Minhas, C.A. Cordeiro, and P.J. Thornalley 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 2002 1 14
7. A. Lapolla, D. Fedele, L. Martano, N.C. Arico', M. Garbeglio, P. Traldi, R. Seraglia, and D. Favretto Advanced glycation end products: a highly complex set of biologically relevant compounds detected by mass spectrometry J. Mass Spectrom. 36 2001 370 378
8. E. Marotta, A. Lapolla, D. Fedele, A. Senesi, R. Reitano, M. Witt, R. Seraglia, and P. Traldi Accurate mass measurements by Fourier transform mass spectrometry in the study of advanced glycation end products/peptides J. Mass Spectrom. 38 2003 196 205
9. T. Kislinger, A. Humeny, C.C. Peich, X. Zhang, T. Niwa, M. Pischetsrieder, and C.M. Becker Relative quantification of N(epsilon)- (carboxymethyl)lysine, imidazolone A, and the amadori product in glycated lysozyme by MALDI-TOF mass spectrometry J. Agric. Food Chem. 51 2003 51 57
10. B.K. Kilhovd, I. Giardino, P.A. Torjesen, K.I. Birkeland, T.J. Berg, P.J. Thornalley, M. Brownlee, and K.F. Hanssen Increased serum levels of the specific AGE-compound methylglyoxal-derived hydroimidazolone in patients with type 2 diabetes Metabolism 52 2003 163 167
11. M. Takeuchi, Y. Yanase, N. Matsuura, S. Yamagishi Si, Y. Kameda, R. Bucala, and Z. Makita Immunological detection of a novel advanced glycation end-product Mol. Med. 7 2001 783 791
12. R.E. Smith, and R. MacQuarrie A sensitive fluorometric method for the determination of arginine using 9,10-phenanthrenequinone Anal. Biochem. 90 1978 246 255
13. R.N. Johnson, P.A. Metcalf, and J.R. Baker Fructosamine: a new approach to the estimation of serum glycosylprotein. An index of diabetic control Clin. Chim. Acta 127 1983 87 95
14. J. Misselwitz, S. Franke, E. Kauf, U. John, and G. Stein Advanced glycation end products in children with chronic renal failure and type 1 diabetes Pediatr. Nephrol. 2002 316 321
15. H. LeVine III Thioflavine T interaction with synthetic Alzheimer's disease beta-amyloid peptides: detection of amyloid aggregation in solution Protein Sci. 2 1993 404 410
16. H. Naiki, K. Higuchi, K. Matsushima, A. Shimada, W.H. Chen, M. Hosokawa, and T. Takeda Fluorometric examination of tissue amyloid fibrils in murine senile amyloidosis: use of the fluorescent indicator, thioflavine T Lab. Invest. 62 1990 768 773
17. A.D. McCarthy, A.M. Cortizo, G. Gimenez Segura, L. Bruzzone, and S.B. Etcheverry Non-enzymatic glycosylation of alkaline phosphatase alters its biological properties Mol. Cell. Biochem. 181 1998 63 69
18. N.W. Seidler, and C. Kowalewski Methylglyoxal-induced glycation affects protein topography Arch. Biochem. Biophys. 410 2003 149 154
19. P. Ulrich, and A. Cerami Protein glycation, diabetes, and aging Recent Prog. Horm. Res. 56 2001 1 21
20. M.E. Westwood, and P.J. Thornalley Molecular characteristics of methylglyoxal-modified bovine and human serum albumins. Comparison with glucose-derived advanced glycation endproduct-modified serum albumins J. Protein Chem. 14 1995 359 372
21. T.W. Lo, M.E. Westwood, A.C. McLellan, T. Selwood, and P.J. Thornalley Binding and modification of proteins by methylglyoxal under physiological conditions. A kinetic and mechanistic study with N alpha-acetylarginine, N alpha-acetylcysteine, and N alpha-acetyllysine, and bovine serum albumin J. Biol. Chem. 269 1994 32299 32305
22. V.M. Monnier, and A. Cerami Nonenzymatic browning in vivo: possible process for aging of long-lived proteins Science 211 1981 491 493
23. M. Stefek, Z. Trnkova, and L. Krizanova 2,4-dinitrophenylhydrazine carbonyl assay in metal-catalysed protein glycoxidation Redox. Rep. 4 1999 43 48
24. T. Kislinger, C. Fu, B. Huber, W. Qu, A. Taguchi, S. Du Yan, M. Hofmann, S.F. Yan, M. Pischetsrieder, D. Stern, and A.M. Schmidt 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 1999 31740 31749
25. B. Bouma, L.M. Kroon-Batenburg, Y.P. Wu, B. Brunjes, G. Posthuma, O. Kranenburg, P.G. de Groot, E.E. Voest, and M.F. Gebbink Glycation induces formation of amyloid cross-beta structure in albumin J. Biol. Chem 278 2003 41810 41819
26. A.M. Schmidt, S.D. Yan, S.F. Yan, and D.M. Stern The multiligand receptor RAGE as a progression factor amplifying immune and inflammatory responses J. Clin. Invest. 108 2001 949 955
27. A.M. Schmidt, S.D. Yan, S.F. Yan, and D.M. Stern The biology of the receptor for advanced glycation end products and its ligands Biochim. Biophys. Acta 1498 2000 99 111
28. J. Husemann, J.D. Loike, R. Anankov, M. Febbraio, and S.C. Silverstein Scavenger receptors in neurobiology and neuropathology: their role on microglia and other cells of the nervous system Glia 40 2002 195 205
29. Y. Tamura, H. Adachi, J. Osuga, K. Ohashi, N. Yahagi, M. Sekiya, H. Okazaki, S. Tomita, Y. Iizuka, H. Shimano, R. Nagai, S. Kimura, M. Tsujimoto, and S. Ishibashi FEEL-1 and FEEL-2 are endocytic receptors for advanced glycation end products J. Biol. Chem. 278 2003 12613 12617
30. J. Leclere, and I. Birlouez-Aragon The fluorescence of advanced Maillard products is a good indicator of lysine damage during the Maillard reaction J. Agric. Food Chem. 49 2001 4682 4687
31. R. Nagai, K. Matsumoto, X. Ling, H. Suzuki, T. Araki, and S. Horiuchi Glycolaldehyde, a reactive intermediate for advanced glycation end products, plays an important role in the generation of an active ligand for the macrophage scavenger receptor Diabetes 49 2000 1714 1723
32. P.J. Coussons, J. Jacoby, A. McKay, S.M. Kelly, N.C. Price, and J.V. Hunt Glucose modification of human serum albumin: a structural study Free Radic. Biol. Med. 22 1997 1217 1227
33. D.L. Price, P.M. Rhett, S.R. Thorpe, and J.W. Baynes Chelating activity of advanced glycation end-product inhibitors J. Biol. Chem. 276 2001 48967 48972
34. D. Edelstein, and M. Brownlee Mechanistic studies of advanced glycosylation end product inhibition by aminoguanidine Diabetes 41 1992 26 29
35. P.J. Thornalley Use of aminoguanidine (Pimagedine) to prevent the formation of advanced glycation endproducts Arch. Biochem. Biophys. 419 2003 31 40