Characterization of glycation adducts on human serum albumin by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

Clinica Chimica Acta

Volumn 385, Issue 1-2, 2007, Pages 48-60

  Wa, Chunling ^a   Cerny, Ronald L ^a   Clarke, William A ^b   Hage, David S ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Diabetes; Human serum albumin; Matrix assisted laser desorption ionization time of flight mass spectrometry; Non enzymatic glycation

Indexed keywords

6 N CARBOXYMETHYLLYSINE; ARGININE; ARGPYRIMIDINE; FRUCTOSYLLYSINE; GLUTAMINE; HUMAN SERUM ALBUMIN; LYSINE; LYSINE DERIVATIVE; N EPSILON (5 HYDRO 4 IMIDAZOLON 2 YL)ORNITHINE; N EPSILON [5 (2,3,4 TRIHYDROXYBUTYL) 5 HYDRO 4 IMIDAZOLON 2 YL]ORNITHINE; N EPSILON CARBOXYETHYLLYSINE; PYRIMIDINE DERIVATIVE; PYRRALINE DERIVATIVE; TETRAHYDROPYRIMIDINE; TRYPSIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; GLYCATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DEGRADATION; PROTEIN MODIFICATION; PROTEIN STRUCTURE; TIME OF FLIGHT MASS SPECTROMETRY;

AMINO ACID SEQUENCE; CARBOHYDRATE METABOLISM; CARBOHYDRATES; GLUTAMIC ACID; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; LYSINE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PROTEIN STRUCTURE, TERTIARY; SERUM ALBUMIN; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TRYPSIN;

EID: 34548482948     PISSN: 00098981     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cca.2007.06.011     Document Type: Article

References (40)

1. In: Theodore Peters J. (Ed). All about albumin: biochemistry, genetics, and medical applications (1996), Academic Press Limited, San Diego, CA
2. Muller W.A., Fehske K.J., and Schlafer S.A.C. Structure of binding sites on albumin. In: Reidenberg M.M., and Erill S. (Eds). Drug-protein binding (1986), Praeger Publishers, New York
3. Sjoholm I. The specificity of drug binding sites on human serum albumin. In: Reidenberg M.M., and Erill S. (Eds). Drug-protein binding (1986), Praeger Publishers, New York
4. He X.M., and Carter D.C. Structure of human serum albumin. Science 249 (1990) 302-303
5. Gwilt P.R., Nahhas R.R., and Tracewell W.G. The effects of diabetes mellitus on pharmacokinetics and pharmacodynamics in humans. Clin Pharmacokinet 20 (1991) 477-490
6. Ulrich P., and Cerami A. Protein glycation, diabetes, and aging. Recent Prog Horm Res 56 (2001) 1-21
7. Bunk D.M. Characterization of the glycation of albumin in freeze-dried and frozen human serum. Anal Chem 69 (1997) 2457-2463
8. Mereish K.A., Rosenberg H., and Cobby J. Glucosylated albumin and its influence on salicylate binding. J Pharm Sci 71 (1982) 235-238
9. Ahmed N., and Thornalley P.J. Chromatographic assay of glycation adducts in human serum albumin glycated in vitro by derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and intrinsic fluorescence. Biochem J 364 (2002) 15-24
10. Lapolla A., Fedele D., and Traldi P. The role of mass spectrometry in the study of non-enzymatic protein glycation in diabetes. Mass Spectrom Rev 19 (2000) 279-304
11. Ahmed N., Dobler D., Dean M., and Thornalley P.J. Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem 280 (2005) 5724-5732
12. Marotta E., Lapolla A., Fedele D., et al. Accurate mass measurements by Fourier transform mass spectrometry in the study of advanced glycation end products/peptides. J Mass Spectrom 38 (2003) 196-205
13. Thornalley Paul J., Battah S., Ahmed N., et al. Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry. Biochem J 375 (2003) 581-592
14. Lapolla A., Fedele D., Reitano R., et al. Enzymatic digestion and mass spectrometry in the study of advanced glycation end products/peptides. J Am Soc Mass Spectrom 15 (2004) 496-509
15. Zhang Y., Cocklin Ross R., Bidasee Keshore R., and Wang M. Rapid determination of advanced glycation end products of proteins using MALDI-TOF-MS and PERL script peptide searching algorithm. J Biomol Tech 14 (2003) 224-230
16. Kislinger T., Humeny A., Peich C.C., Becker C.-M., and Pischetsrieder M. Analysis of protein glycation products by MALDI-TOF-MS. Ann NY Acad Sci 1043 (2005) 249-259
17. Thornalley P.J., Argirova M., Ahmed N., Mann V.M., Argirov O., and Dawnay A. Mass spectrometric monitoring of albumin in uremia. Kidney Int 58 (2000) 2228-2234
18. Lapolla A., Fedele D., Reitano R., et al. Advanced glycation end products/peptides: an in vivo investigation. Ann NY Acad Sci 1043 (2005) 267-275
19. Gugliucci A., and Bendayan M. Renal fate of circulating advanced glycated end products (AGE): Evidence for reabsorption and catabolism of AGE-peptides by renal proximal tubular cells. Diabetologia 39 (1996) 149-160
20. Gugliucci A., and Menini T. Circulating advanced glycation peptides in streptozotocin-induced diabetic rats: evidence for preferential modification of IgG light chains. Life Sci 62 (1998) 2141-2150
21. Gatti G., Crema F., Attardo-Parrinello G., Fratino P., Aguzzi F., and Perucca E. Serum protein binding of phenytoin and valproic acid in insulin-dependent diabetes mellitus. Ther Drug Monit 9 (1987) 389-391
22. McNamara P.J., Blouin R.A., and Brazzell R.K. The protein binding of phenytoin, propranolol, diazepam, and AL01576 (an aldose reductase inhibitor) in human and rat diabetic serum. Pharm Res 5 (1988) 261-265
23. Bohney J.P., and Feldhoff R.C. Effects of nonenzymatic glycosylation and fatty acids on tryptophan binding to human serum albumin. Biochem Pharmacol 43 (1992) 1829-1834
24. Okabe N., and Nakasaka T. Drug binding properties of glycosylated bovine serum albumin as measured by circular dichroism. Biol Pharm Bull 17 (1994) 1505-1507
25. Wa C., Cerny R., and Hage David S. Obtaining high sequence coverage in matrix-assisted laser desorption time-of-flight mass spectrometry for studies of protein modification: analysis of human serum albumin as a model. Anal Biochem 349 (2006) 229-241
26. Laugesen S., and Roepstorff P. Combination of two matrices results in improved performance of MALDI MS for peptide mass mapping and protein analysis. J Am Soc Mass Spectrom 14 (2003) 992-1002
27. Wilkins M.R., Lindskog I., Gasteiger E., et al. Detailed peptide characterization using PEPTIDEMASS - a World-Wide-Web-accessible tool. Electrophoresis 18 (1997) 403-408
28. Nordhoff E., Egelhofer V., Giavalisco P., et al. Large-gel two-dimensional electrophoresis-matrix assisted laser desorption/ionization-time of flight-mass spectrometry: an analytical challenge for studying complex protein mixtures. Electrophoresis 22 (2001) 2844-2855
29. Jensen O.N., Podtelejnikov A., and Mann M. Delayed extraction improves specificity in database searches by matrix-assisted laser desorption/ionization peptide maps. Rapid Commun Mass Spectrom 10 (1996) 1371-1378
30. a values. Proteins 61 (2005) 704-721
31. Willard L., Ranjan A., Zhang H., et al. VADAR: A web server for quantitative evaluation of protein structure quality. Nucleic Acids Res 31 (2003) 3316-3319
32. Martz E. Protein Explorer: easy yet powerful macromolecular visualization. Trends Biochem Sci 27 (2002) 107-109
33. Ahmed N., Argirov Ognian K., Minhas Harjit S., Cordeiro Carlos A.A., and Thornalley Paul J. Assay of advanced glycation endproducts (AGEs): Surveying AGEs by chromatographic assay with derivatization by 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and application to Nε-carboxymethyl-lysine- and Nε(-(1-carboxyethyl)lysine-modified albumin. Biochem J 364 (2002) 1-14
34. Jing H., and Kitts D.D. Physiological and pharmacological properties of Maillard reaction products. Recent Res Dev Mol Cell Biochem 1 (2003) 59-75
35. Monnier V.M. Intervention against the Maillard reaction in vivo. Arch Biochem Biophys 419 (2003) 1-15
36. Garlick R.L., and Mazer J.S. The principal sites of nonenzymatic glycosylation of human serum albumin in vivo. J Biol Chem 258 (1983) 6142-6146
37. Day J.F., Thorpe S.R., and Baynes J.W. Nonenzymically glucosylated albumin. In vitro preparation and isolation from normal human serum. J Biol Chem 254 (1979) 595-597
38. Iberg N., and Flueckiger R. Nonenzymic glycosylation of albumin in vivo. Identification of multiple glycosylated sites. J Biol Chem 261 (1986) 13542-13545
39. Howard M.J., and Smales C.M. NMR analysis of synthetic human serum albumin α-helix 28 identifies structural distortion upon Amadori modification. J Biol Chem 280 (2005) 22582-22589
40. Shaklai N., Garlick R.L., and Bunn H.F. Nonenzymatic glycosylation of human serum albumin alters its conformation and function. J Biol Chem 259 (1984) 3812-3817