Glycated albumin: An overview of the In Vitro models of an In Vivo potential disease marker

Journal of Diabetes and Metabolic Disorders

Volumn 13, Issue 1, 2014, Pages

  Arasteh, Amir ^a   Farahi, Sara ^b   Habibi Rezaei, Mehran ^b   Moosavi Movahedi, Ali A ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF TEHRAN   (Iran)

Author keywords

Diabetes; Disease marker; Glycation; Human serum albumin

Indexed keywords

ADVANCED GLYCATION END PRODUCT; BOVINE SERUM ALBUMIN; GLUCOSE; GLYCOSYLATED ALBUMIN; HEMOGLOBIN A1C; HUMAN SERUM ALBUMIN;

ALZHEIMER DISEASE; ARTERIOSCLEROSIS; BINDING SITE; CARBOHYDRATE ANALYSIS; CATARACT; DIABETES MELLITUS; DISEASE MARKER; DISEASE MODEL; DRUG PROTEIN BINDING; GLUCOSE BLOOD LEVEL; GLYCEMIC CONTROL; HALF LIFE TIME; HUMAN; IN VITRO STUDY; IN VIVO STUDY; PROTEIN AGGREGATION; PROTEIN GLYCOSYLATION; PROTEIN STRUCTURE; REVIEW;

EID: 84910070220     PISSN: None     EISSN: 22516581     Source Type: Journal    
DOI: 10.1186/2251-6581-13-49     Document Type: Review

References (114)

1. Rondeau P, Navarra G, Militello V, Bourdon E. On the Aggregation of Albumin: Influences of the Protein Glycation. Protein Aggregation 2010, Stein Nova Science Publishers, Inc, Douglas A.
2. Evans T. Review article: albumin as a drug-biological effects of albumin unrelated to oncotic pressure. Aliment Pharmacol Ther 2002, 16:6-11.
3. Peters T. ScienceDirect: All about albumin: biochemistry, genetics, and medical applications 1996, CA: Academic Press San Diego.
4. Foster J, Rosenoer V, Oratz M. Albumin structure, function and uses. 1977, 53-84. Oxford: Pergamon, Rosenoer VM, Oratz M, Rothschild MA.
5. Scatchard G, Batchelder A, Brown A. Chemical, clinical, and immunological studies on the products of human plasma fractionation. VI. The osmotic pressure of plasma and of serum albumin. J Clin Invest 1944, 23:458.
6. Figge J, Rossing T, Fencl V. The role of serum proteins in acid-base equilibria. J Lab Clin Med 1991, 117:453.
7. Waldmann T, Rosenoer V, Oratz M, Rothschild M. Albumin Structure, Function and Uses 1977, New York: Pergamon Press.
8. Wood M. Plasma drug binding: implications for anesthesiologists. Anesth Analg 1986, 65:786.
9. Kratz F. Albumin as a drug carrier: design of prodrugs, drug conjugates and nanoparticles. J Control Release 2008, 132:171-183.
10. Sudlow G, Birkett D, Wade D. Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol 1976, 12:1052.
11. Weber G. Energetics of ligand binding to proteins. Adv Protein Chem 1975, 29:68.
12. Daneshgar P, Moosavi-Movahedi AA, Norouzi P, Ganjali MR, Madadkar-Sobhani A, Saboury AA. Molecular interaction of human serum albumin with paracetamol: Spectroscopic and molecular modeling studies. Int J Biol Macromol 2009, 45:129-134.
13. Petitpas I, Bhattacharya AA, Twine S, East M, Curry S. Crystal structure analysis of warfarin binding to human serum albumin. J Biol Chem 2001, 276:22804.
14. Qiu Y, Burlingame A, Benet L. Mechanisms for covalent binding of benoxaprofen glucuronide to human serum albumin. Drug Metab Dispos 1998, 26:246-256.
15. Oettl K, Stauber R. Physiological and pathological changes in the redox state of human serum albumin critically influence its binding properties. Br J Pharmacol 2007, 151:580-590.
16. Thornalley PJ, Argirova M, Ahmed N, Mann VM, Argirov O, Dawnay A. Mass spectrometric monitoring of albumin in uremia. Kidney Int 2000, 58:2228-2234.
17. Halliwell B, Gutteridge J. The antioxidants of human extracellular fluids. Arch Biochem Biophys 1990, 280:1-8.
18. Bourdon E, Blache D. The importance of proteins in defense against oxidation. Antioxid Redox Signal 2001, 3:293-311.
19. Roche M, Rondeau P, Singh NR, Tarnus E, Bourdon E. The antioxidant properties of serum albumin. FEBS letters 2008, 582:1783-1787.
20. Carballal S, Alvarez B, Turell L, Botti H, Freeman B, Radi R. Sulfenic acid in human serum albumin. Amino Acids 2007, 32:543-551.
21. Lee H, Kim IH. Thioredoxin-linked lipid hydroperoxide peroxidase activity of human serum albumin in the presence of palmitoyl coenzyme A. Free Radic Biol Med 2001, 30:327-333.
22. Levine RL, Berlett BS, Moskovitz J, Mosoni L, Stadtman ER. Methionine residues may protect proteins from critical oxidative damage. Mech Ageing Dev 1999, 107:323-332.
23. Bhonsle HS, Singh SK, Srivastava G, Boppana R, Kulkarni MJ. Albumin competitively inhibits glycation of less abundant proteins. Protein Pept Lett 2008, 15:663-667.
24. Gelamo E, Tabak M. Spectroscopic studies on the interaction of bovine (BSA) and human (HSA) serum albumins with ionic surfactants. Spectrochim Acta A Mol Biomol Spectrosc 2000, 56:2255-2271.
25. Militello V, Vetri V, Leone M. Conformational changes involved in thermal aggregation processes of bovine serum albumin. Biophys Chem 2003, 105:133-141.
26. Arasteh A, Habibi Rezaei M, Ebrahim Habibi A, Moosavi Movahedi Ali A. Bovine serum albumin aggregation: An optimizing approach. Clin Biochem 2011, 44:S136-S137.
27. Brewer SH, Glomm WR, Johnson MC, Magne K, Franzen S. Probing BSA binding to citrate-coated gold nanoparticles and surfaces. Langmuir 2005, 21:9303-9307.
28. Taboada P, Gutiérrez-Pichel M, Mosquera V. Effects of the molecular structure of two amphiphilic antidepressant drugs on the formation of complexes with human serum albumin. Biomacromolecules 2004, 5:1116-1123.
29. Dockal M, Carter DC, Rüker F. Conformational transitions of the three recombinant domains of human serum albumin depending on pH. J Biol Chem 2000, 275:3042-3050.
30. Bouma B, Kroon-Batenburg LMJ, Wu YP, Brünjes B, Posthuma G, Kranenburg O, de Groot PG, Voest EE, Gebbink MFBG. Glycation induces formation of amyloid cross-β structure in albumin. J Biol Chem 2003, 278:41810.
31. Gul A, Rahman MA, Salim A, Simjee SU. Advanced glycation end products in senile diabetic and nondiabetic patients with cataract. J Diabetes Complications 2009, 23:343-348.
32. Tomizawa H, Yamazaki M, Kunika K, Itakura M, Yamashita K. Association of elastin glycation and calcium deposit in diabetic rat aorta. Diabetes Res Clin Pract 1993, 19:1-8.
33. Rondeau P, Bourdon E. The glycation of albumin: Structural and functional impacts. Biochimie 2011, 93:645-658.
34. Suarez G, Rajaram R, Oronsky A, Gawinowicz M. Nonenzymatic glycation of bovine serum albumin by fructose (fructation). Comparison with the Maillard reaction initiated by glucose. J Biol Chem 1989, 264:3674.
35. Sattarahmady N, Moosavi-Movahedi AA, Habibi-Rezaei M, Ahmadian S, Saboury AA, Heli H, Sheibani N. Detergency effects of nanofibrillar amyloid formation on glycation of human serum albumin. Carbohydr Res 2008, 343:2229-2234.
36. Davis LJ, Hakim G, Rossi CA. Kinetics of the glycation of bovine serum albumin by mannose and fucose in vitro. Biochem Biophys Res Commun 1989, 160:362-366.
37. Avigad G, Kniep A, Bailin G. Reaction of rabbit skeletal myosin with D-glucose 6-phosphate. IUBMB Life 1996, 40:273-284.
38. Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T. Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol 2004, 108:189-193.
39. Ravelojaona V, Robert AM, Robert L. Expression of senescence-associated β-galactosidase (SA-β-Gal) by human skin fibroblasts, effect of advanced glycation end-products and fucose or rhamnose-rich polysaccharides. Arch Gerontol Geriatr 2009, 48:151-154.
40. Rondeau P, Navarra G, Cacciabaudo F, Leone M, Bourdon E, Militello V. Thermal aggregation of glycated bovine serum albumin. Biochimica et Biophysica Acta (BBA)-Proteins & Proteomics 2010, 1804:789-798.
41. Zarina S, Zhao HR, Abraham E. Advanced glycation end products in human senile and diabetic cataractous lenses. Mol Cell Biochem 2000, 210:29-34.
42. Chetyrkin S, Mathis M, Ham A, Hachey D, Hudson B, Voziyan P. Propagation of protein glycation damage involves modification of tryptophan residues via reactive oxygen species: inhibition by pyridoxamine. Free Radic Biol Med 2008, 44:1276-1285.
43. Monnier V, Sell D, Nagaraj R, Miyata S, Grandhee S, Odetti P, Ibrahim S. Maillard reaction-mediated molecular damage to extracellular matrix and other tissue proteins in diabetes, aging, and uremia. Diabetes 1992, 41:36.
44. Vlassara H. Advanced glycation in health and disease: role of the modern environment. Ann N Y Acad Sci 2005, 1043:452-460.
45. Ulrich P, Cerami A. Protein glycation, diabetes, and aging. Recent progress in hormone research 2001, 56:1-22.
46. Kikuchi S, Shinpo K, Ogata A, Tsuji S, Takeuchi M, Makita Z, Tashiro K. Detection of Nepsilon-(carboxymethyl) lysine (CML) and non-CML advanced glycation end-products in the anterior horn of amyotrophic lateral sclerosis spinal cord. Amyotroph Lateral Scler 2002, 3:63-68.
47. Vlassara H, Bucala R, Striker L. Pathogenic effects of advanced glycosylation: biochemical, biologic, and clinical implications for diabetes and aging. Lab Invest 1994, 70:138.
48. Fu MX, Requena JR, Jenkins AJ, Lyons TJ, Baynes JW, Thorpe SR. The advanced glycation end product, N-(carboxymethyl) lysine, is a product of both lipid peroxidation and glycoxidation reactions. J Biol Chem 1996, 271:9982.
49. Dyer D, Blackledge J, Thorpe S, Baynes J. Formation of pentosidine during nonenzymatic browning of proteins by glucose. Identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo. J Biol Chem 1991, 266:11654.
50. Nakayama M, Kawaguchi Y, Yamada K, Hasegawa T, Takazoe K, Katoh N, Hayakawa H, Osaka N, Yamamoto H, Ogawa A. Immunohistochemical detection of advanced glycosylation end-products in the peritoneum and its possible pathophysiological role in CAPD. Kidney Int 1997, 51:182-186.
51. Niwa T, Katsuzaki T, Ishizaki Y, Hayase F, Miyazaki T, Uematsu T, Tatemichi N, Takei Y. Imidazolone, a novel advanced glycation end product, is present at high levels in kidneys of rats with streptozotocin-induced diabetes. FEBS letters 1997, 407:297-302.
52. Kikuchi S, Shinpo K, Takeuchi M, Yamagishi S, Makita Z, Sasaki N, Tashiro K. Glycation-a sweet tempter for neuronal death. Brain Res Rev 2003, 41:306-323.
53. Smith MA, Taneda S, Richey PL, Miyata S, Yan SD, Stern D, Sayre LM, Monnier VM, Perry G. Advanced Maillard reaction end products are associated with Alzheimer disease pathology. Proc Natl Acad Sci 1994, 91:5710.
54. Myint T, Hoshi S, Ookawara T, Miyazawa N, Suzuki K, Taniguchi N. Immunological detection of glycated proteins in normal and streptozotocin-induced diabetic rats using anti hexitol-lysine IgG. Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease 1995, 1272:73-79.
55. Ryle C, Leow C, Donaghy M. Nonenzymatic glycation of peripheral and central nervous system proteins in experimental diabetes mellitus. Muscle & Nerve 1997, 20:577-584.
56. Castellani R, Smith M, Richey G, Perry G. Glycoxidation and oxidative stress in Parkinson disease and diffuse Lewy body disease. Brain Res 1996, 737:195-200.
57. Chondrogianni N, Stratford FLL, Trougakos IP, Friguet B, Rivett AJ, Gonos ES. Central role of the proteasome in senescence and survival of human fibroblasts. J Biol Chem 2003, 278:28026-28037.
58. Mary J, Vougier S, Picot CR, Perichon M, Petropoulos I, Friguet B. Enzymatic reactions involved in the repair of oxidized proteins. Exp Gerontol 2004, 39:1117-1123.
59. Chen Q, Ding Q, Thorpe J, Dohmen RJ, Keller JN. RNA interference toward UMP1 induces proteasome inhibition in Saccharomyces cerevisiae: evidence for protein oxidation and autophagic cell death. Free Radic Biol Med 2005, 38:226-234.
60. Rodgers KJ, Hume PM, Dunlop RA, Dean RT. Biosynthesis and turnover of DOPA-containing proteins by human cells. Free Radic Biol Med 2004, 37:1756-1764.
61. Grune T, Merker K, Sandig G, Davies KJA. Selective degradation of oxidatively modified protein substrates by the proteasome. Biochem Biophys Res Commun 2003, 305:709-718.
62. Bulteau AL, Verbeke P, Petropoulos I, Chaffotte AF, Friguet B. Proteasome inhibition in glyoxal-treated fibroblasts and resistance of glycated glucose-6-phosphate dehydrogenase to 20 S proteasome degradation in vitro. J Biol Chem 2001, 276:45662-45668.
63. Stolzing A, Widmer R, Jung T, Voss P, Grune T. Degradation of glycated bovine serum albumin in microglial cells. Free Radic Biol Med 2006, 40:1017-1027.
64. Swamy M, Tsai C, Abraham A, Abraham E. Glycation mediated lens crystallin aggregation and cross-linking by various sugars and sugar phosphates in vitro. Exp Eye Res 1993, 56:177-185.
65. Ortwerth BJ, Slight SH, Prabhakaram M, Sun Y, Smith JB. Site-specific glycation of lens crystallins by ascorbic acid. Biochimica et Biophysica Acta (BBA)-General Subjects 1992, 1117:207-215.
66. Ahmed N, Thornalley PJ, Dawczynski J, Franke S, Strobel J, Stein G, Haik GM. Methylglyoxal-derived hydroimidazolone advanced glycation end-products of human lens proteins. Invest Ophthalmol Vis Sci 2003, 44:5287.
67. Swamy M, Abraham E. Differential glycation of rat [alpha]-,[beta]-and [gamma]-crystallins. Exp Eye Res 1991, 52:439-444.
68. Hotta K, Funahashi T, Arita Y, Takahashi M, Matsuda M, Okamoto Y, Iwahashi H, Kuriyama H, Ouchi N, Maeda K. Plasma concentrations of a novel, adipose-specific protein, adiponectin, in type 2 diabetic patients. Arterioscler Thromb Vasc Biol 2000, 20:1595-1599.
69. Lanzer P. Topographic distribution of peripheral arteriopathy in non-diabetics and type 2 diabetics. Z Kardiol 2001, 90:99-103.
70. Baynes JW. Role of oxidative stress in development of complications in diabetes. Diabetes 1991, 40:405-412.
71. Okada E, Oida K, Tada H, Asazuma K, Eguchi K, Tohda G, Kosaka S, Takahashi S, Miyamori I. Hyperhomocysteinemia is a risk factor for coronary arteriosclerosis in Japanese patients with type 2 diabetes. Diabetes Care 1999, 22:484.
72. Shuvaev VV, Laffont I, Serot JM, Fujii J, Taniguchi N, Siest G. Increased protein glycation in cerebrospinal fluid of Alzheimer's disease. Neurobiology of aging 2001, 22:397-402.
73. Moreira PI, Smith MA, Zhu X, Nunomura A, Castellani RJ, Perry G. Oxidative stress and neurodegeneration. Ann N Y Acad Sci 2005, 1043:545-552.
74. Zhu X, Su B, Wang X, Smith M, Perry G. Causes of oxidative stress in Alzheimer disease. Cellular and molecular life sciences 2007, 64:2202-2210.
75. Münch G, Schinzel R, Loske C, Wong A, Durany N, Li J, Vlassara H, Smith M, Perry G, Riederer P. Alzheimer's disease-synergistic effects of glucose deficit, oxidative stress and advanced glycation endproducts. J Neural Transm 1998, 105:439-461.
76. Wei Y, Chen L, Chen J, Ge L, He R. Rapid glycation with D-ribose induces globular amyloid-like aggregations of BSA with high cytotoxicity to SH-SY5Y cells. BMC cell biology 2009, 10:10.
77. Bourdon E, Loreau N, BLACHE D. Glucose and free radicals impair the antioxidant properties of serum albumin. The FASEB journal 1999, 13:233-244.
78. Szapacs ME, Riggins JN, Zimmerman LJ, Liebler DC. Covalent adduction of human serum albumin by 4-hydroxy-2-nonenal: kinetic analysis of competing alkylation reactions. Biochemistry 2006, 45:10521-10528.
79. Rondeau P, Singh NR, Caillens H, Tallet F, Bourdon E. Oxidative stresses induced by glycoxidized human or bovine serum albumin on human monocytes. Free Radic Biol Med 2008, 45:799-812.
80. Iberg N, Flückiger R. Nonenzymatic glycosylation of albumin in vivo. Identification of multiple glycosylated sites. Identification of multiple glycosylated sites. J Biol Chem 1986, 261:13542-13545.
81. Lapolla A, Fedele D, Reitano R, Aricò NC, Seraglia R, Traldi P, Marotta E, Tonani R. Enzymatic digestion and mass spectrometry in the study of advanced glycation end products/peptides. J Am Soc Mass Spectrom 2004, 15:496-509.
82. Wa C, Cerny RL, Clarke WA, Hage DS. Characterization of glycation adducts on human serum albumin by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clin Chim Acta 2007, 385:48-60.
83. Frolov A, Hoffmann R. Identification and relative quantification of specific glycation sites in human serum albumin. Anal Bioanal Chem 2010, 397:2349-2356.
84. Hinton D, Ames J. Site specificity of glycation and carboxymethylation of bovine serum albumin by fructose. Amino Acids 2006, 30:425-434.
85. Ahmed N, Dobler D, Dean M, Thornalley PJ. Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem 2005, 280:5724.
86. Zeng J, Davies MJ. Evidence for the formation of adducts and S-(carboxymethyl) cysteine on reaction of α-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins. Chem Res Toxicol 2005, 18:1232-1241.
87. Mostafa AA, Randell EW, Vasdev SC, Gill VD, Han Y, Gadag V, Raouf AA, El Said H. Plasma protein advanced glycation end products, carboxymethyl cysteine, and carboxyethyl cysteine, are elevated and related to nephropathy in patients with diabetes. Mol Cell Biochem 2007, 302:35-42.
88. Sattarahmady N, Moosavi-Movahedi AA, Ahmad F, Hakimelahi GH, Habibi-Rezaei M, Saboury AA, Sheibani N. Formation of the molten globule-like state during prolonged glycation of human serum albumin. Biochim Biophys Acta 2007, 1770:933-942.
89. Brownlee M. The pathological implications of protein glycation. Clinical and investigative medicine Medecine clinique et experimentale 1995, 18:275.
90. Chen S, Cohen MP, Ziyadeh FN. Amadori-glycated albumin in diabetic nephropathy: pathophysiologic connections. Kidney Int 2000, 58:S40-S44.
91. HASAN NA. Effects of trace elements on albumin and lipoprotein glycation in diabetic retinopathy. Saudi Med J 2009, 30:1263-1271.
92. Rubenstein DA, Yin W. Glycated albumin modulates platelet susceptibility to flow induced activation and aggregation. Platelets 2009, 20:206-215.
93. Candiloros H, Muller S, Ziegler O, Donner M, Drouin P. Role of albumin glycation on the erythrocyte aggregation: An in vitro study. Diabet Med 1996, 13:646-650.
94. Unoki H, Bujo H, Yamagishi S, Takeuchi M, Imaizumi T, Saito Y. Advanced glycation end products attenuate cellular insulin sensitivity by increasing the generation of intracellular reactive oxygen species in adipocytes. Diabetes research and clinical practice 2007, 76:236-244.
95. Brandt R, Nawka M, Kellermann J, Salazar R, Becher D, Krantz S. Nucleophosmin is a component of the fructoselysine-specific receptor in cell membranes of Mono Mac 6 and U937 monocyte-like cells. Biochimica et Biophysica Acta (BBA)-General Subjects 2004, 1670:132-136.
96. Roohk HV, Zaidi AR. A review of glycated albumin as an intermediate glycation index for controlling diabetes. J Diabetes Sci Technol 2008, 2:1114.
97. Hashimoto K, Osugi T, Noguchi S, Morimoto Y, Wasada K, Imai S, Waguri M, Toyoda R, Fujita T, Kasayama S. A1C but not serum glycated albumin is elevated because of iron deficiency in late pregnancy in diabetic women. Diabetes Care 2010, 33:509.
98. Jeffcoate S. Diabetes control and complications: the role of glycated haemoglobin, 25 years on. Diabetic Med 2004, 21:657-665.
99. Kosecki SM, Rodgers PT, Adams MB. Glycemic monitoring in diabetics with sickle cell plus β-thalassemia hemoglobinopathy. The Annals of pharmacotherapy 2005, 39:1557-1560.
100. Yoshiuchi K, Matsuhisa M, Katakami N, Nakatani Y, Sakamoto K, Matsuoka T, Umayahara Y, Kosugi K, Kaneto H, Yamasaki Y. Glycated albumin is a better indicator for glucose excursion than glycated hemoglobin in type 1 and type 2 diabetes. Endocr J 2008, 55:503-508.
101. Koga M, Murai J, Saito H, Aoki K, Kanehara H, Bando Y, Morita S, Kasayma S. Glycated albumin levels are higher relative to HbA1c levels in patients with autoimmune acute-onset type 1 diabetes mellitus than in patients with type 2 diabetes mellitus at the time of diagnosis. Diabetes Research Clin Pract 2011, 94:12-14.
102. Okumura A, Mitamura Y, Namekata K, Nakamura K, Harada C, Harada T. Glycated albumin induces activation of activator protein-1 in retinal glial cells. Jpn J Ophthalmol 2007, 51:236-237.
103. Nagayama H, Inaba M, Okabe R, Emoto M, Ishimura E, Okazaki S, Nishizawa Y. Glycated albumin as an improved indicator of glycemic control in hemodialysis patients with type 2 diabetes based on fasting plasma glucose and oral glucose tolerance test. Biomed Pharmacother 2009, 63:236-240.
104. Koga M, Murai J, Saito H, Matsumoto S, Kasayama S. Effects of thyroid hormone on serum glycated albumin levels: Study on non-diabetic subjects. Diabetes Research Clin Pract 2009, 84:163-167.
105. Koga M, Matsumoto S, Saito H, Kasayama S. Body mass index negatively influences glycated albumin, but not glycated hemoglobin, in diabetic patients. Endocr J 2006, 53:387-391.
106. Nishimura R, Kanda A, Sano H, Matsudaira T, Miyashita Y, Morimoto A, Shirasawa T, Kawaguchi T, Tajima N. Glycated albumin is low in obese, non-diabetic children. Diabetes Research Clin Pract 2006, 71:334-338.
107. Cohen MP, Ziyadeh FN. Role of Amadori-modified nonenzymatically glycated serum proteins in the pathogenesis of diabetic nephropathy. J Am Soc Nephrol 1996, 7:183-190.
108. Buckow R, Wendorff J, Hemar Y. Conjugation of Bovine Serum Albumin and Glucose under Combined High Pressure and Heat. J Agric Food Chem 2011, 59:3915-3923.
109. Munanairi A, O'Banion SK, Gamble R, Breuer E, Harris AW, Sandwick RK. The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates. Carbohydr Res 2007, 342:2575-2592.
110. Syrový I. Glycation of albumin: reaction with glucose, fructose, galactose, ribose or glyceraldehyde measured using four methods. Journal of biochemical and biophysical methods 1994, 28:115-121.
111. Schmitt A, Schmitt J, Münch G, Gasic-Milencovic J. Characterization of advanced glycation end products for biochemical studies: side chain modifications and fluorescence characteristics. Analytical Biochemistry 2005, 338:201-215.
112. GhoshMoulick R, Bhattacharya J, Roy S, Basak S, Dasgupta AK. Compensatory secondary structure alterations in protein glycation. Biochimica et Biophysica Acta (BBA)-Proteins and Proteomics 2007, 1774:233-242.
113. > 18 > O-labeling and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clin Chim Acta 2010, 411:1102-1110.
114. Holm NK, Jespersen SK, Thomassen LV, Wolff TY, Sehgal P, Thomsen LA, Christiansen G, Andersen CB, Knudsen AD, Otzen DE. Aggregation and fibrillation of bovine serum albumin. Biochimica et Biophysica Acta (BBA)-Proteins & Proteomics 2007, 1774:1128-1138.