Degradation products of proteins damaged by glycation, oxidation and nitration in clinical type 1 diabetes

Diabetologia

Volumn 48, Issue 8, 2005, Pages 1590-1603

  Ahmed, N ^a   Babaei Jadidi, R ^a   Howell, S K ^b   Beisswenger, P J ^b   Thornalley, P J ^a  

^a UNIVERSITY OF ESSEX   (United Kingdom)

^b DARTMOUTH HITCHCOCK MEDICAL CENTER   (United States)

Author keywords

3 Nitrotyrosine; Glycation; HbA1c; Oxidative stress; Type 1 diabetes

Indexed keywords

3 NITROTYROSINE; ANTICOAGULANT AGENT; HEMOGLOBIN; HEPARIN; PENTOSIDINE; PLASMA PROTEIN;

ADULT; ARTICLE; BLOOD SAMPLING; CLINICAL ARTICLE; CONTROLLED STUDY; FEMALE; HUMAN; INSULIN DEPENDENT DIABETES MELLITUS; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; NITRATION; OXIDATION KINETICS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BLOOD LEVEL; PROTEIN DEGRADATION; PROTEIN GLYCOSYLATION; PROTEIN URINE LEVEL; SCREENING; URINALYSIS;

ADULT; BLOOD PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; DIABETES MELLITUS, TYPE 1; FEMALE; GLYCOSYLATION END PRODUCTS, ADVANCED; HEMOGLOBIN A, GLYCOSYLATED; HEMOGLOBINS; HUMANS; MALE; MASS SPECTROMETRY; MIDDLE AGED; NITRATES; OXIDATION-REDUCTION;

EID: 22444447985     PISSN: 0012186X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00125-005-1810-7     Document Type: Article

References (56)

1. Manley S (2003) Haemoglobin A(1c) - A marker for complications of type 2 diabetes: the experience from the UK Prospective Diabetes Study (UKPDS). Clin Chem Lab Med 41:1182-1190
2. Thornalley PJ (1999) Clinical significance of glycation. Clin Lab 45:263-273
3. Baynes JW, Thorpe SR (1999) Role of oxidative stress in diabetic complications: a new perspective on an old paradigm. Diabetes 48:1-9
4. Pennathur S, Heinecke JW (2004) Mechanisms of oxidative stress in diabetes: implications for the pathogenesis of vascular disease and antioxidant therapy. Front Biosci 9:565-574
5. Thornalley PJ, Battah S, Ahmed N et al (2003) Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry. Biochem J 375:581-592
6. Goldberg AL (2003) Protein degradation and protection against misfolded or damaged proteins. Nature 426:895-899
7. Wells-Knecht MC, Lyons TJ, McCance DR, Thorpe SR, Baynes JW (1997) Age-dependent increases in ortho-tyrosine and methionine sulfoxide in human skin collagen is not accelerated in diabetes. J Clin Invest 100:839-846
8. Geibauf A, van Wickern B, Simat T, Steinhart H, Esterbauer H (1996) Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation. FEBS Lett 389:136-140
9. Gaut JP, Byun J, Tran HD, Heinecke JW (2002) Artifact-free quantitation of free 3-chlorotyrosine, 3-bromotyrosine, and 3-nitrotyrosine in human plasma by electron capture-negative chemical ionization gas chromatography mass spectrometry and liquid chromatography-electrospray ionization tandem mass spectrometry. Anal Biochem 300:252-259
10. Beisswenger PJ, Wood ME, Howell SK, Touchette AD, O'Dell RM, Szwergold BS (2001) α-Oxoaldehydes increase in the postprandial period and reflect the degree of hyperglycaemia. Diabetes Care 24:726-732
11. Ahmed N, Argirov OK, Minhas HS, Cordeiro CA, Thornalley PJ (2002) Assay of advanced glycation endproducts (AGEs): surveying AGEs by chromatographic assay with derivatisation by aminoquinolyl-N-hydroxysuccimidyl-carbamate and application to Nε-carboxymethyl-lysine- and Nε-(1-carboxyethyl) lysine-modified albumin. Biochem J 364:1-14
12. Simat T, Meyer K, Steinhart H (1994) Synthesis and analysis of oxidation and carbonyl condensation products of tryptophan. J Chromatogr A 661:93-99
13. HalwachsBaumann G, Katzensteiner S, Schnedl W, Purstner P, Pieber T, WildersTruschnig M (1997) Comparative evaluation of three assay systems for automated determination of hemoglobin A(1c). Clin Chem 43:511-517
14. Russo LM, Bakris GL, Comper WD (2002) Renal handling of albumin: a critical review of basic concepts and perspective. Amer J Kidney Dis 39:899-919
15. Cohen RM, Franco RS, Joiner CH (2004) Is poor glycemic control associated with reduced red blood cell lifespan? Diabetes Care 27:1013-1014
16. Henle T (2003) AGEs in foods: do they play a role in uremia? Kidney Int 63:S145-S147
17. Ahmed N, Thornalley PJ, Luthen R et al (2004) Processing of protein glycation, oxidation and nitrosation adducts in the liver and the effect of cirrhosis. J Hepatol 41:913-919
18. Johnson RN, Easdale RW, Tatnell M, Baker JR (1991) Significance of variation in turnover of glycated albumin on indexes of diabetic control. Clin Chim Acta 198:229-238
19. Sayinalp S, Sozen T, Usman A, Dundar S (1995) Investigation of the effect of poorly controlled diabetes mellitus on erythrocyte life. J Diabetes Complications 9:190-193
20. Yamamoto Y, Tahara Y, Cha T et al (1989) Radioimmunoassay of glycated serum protein using monoclonal antibody to glucitollysine and Coomassie-brilliant blue-coated polystyrene beads. Diabetes Res 11:45-49
21. Yatscoff RW, Tevaarwerk GJM, Macdonald JC (1984) Quantification of nonenzymically glycated albumin and total serum-protein by affinity- chromatography. Clin Chem 30:446-449
22. Baynes JW, Thorpe SR, Murtiashaw MH (1984) Nonenzymatic glycosylation of lysine residues in albumin. Methods Enzymol 106:88-98
23. Roberts NB, Amara AB, Morris M, Green BN (2001) Long-term evaluation of electrospray ionization mass spectrometric analysis of glycated hemoglobin. Clin Chem 47:316-321
24. Zhang X, Medzihradszhy KF, Cunningham J et al (2001) Characterization of glycated hemoglobin in diabetic patients: usefulness of electrospray mass spectrometry in monitoring the extent and distribution of glycation. J Chromatogr B 759:1-15
25. Knecht KJ, Dunn JA, Mcfarland KF et al (1991) Effect of diabetes and aging on carboxymethyllysine levels in human urine. Diabetes 40:190-196
26. Szwergold BS, Howell S, Beisswenger PJ (2001) Human fructosamine-3- kinase. Purification, sequencing, substrate specificity, and evidence of activity in vivo. Diabetes 50:2139-2147
27. Ahmed N, Dobler D, Dean M, Thornalley PJ (2005) Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem 280:5724-5732
28. Schleicher ED, Wagner E, Nerlich AG (1997) Increased accumulation of the glycoxidation product Nε-(carboxymethyl)lysine in human tissues in diabetes and aging. J Clin Invest 99: 457-468
29. Makita Z, Vlassara H, Rayfield E et al (1992) Hemoglobin-AGE: a circulating marker of advanced glycosylation. Science 258:651-653
30. Turk Z, Mesic R, Benko B (1998) Comparison of advanced glycation endproducts on haemoglobin (Hb-AGE) and haemoglobin A(1c) for the assessment of diabetic control. Clin Chim Acta 277:159-170
31. Cai J, Hurst HE (1999) Identification and quantitation of N-(carboxymethyl)valine adducts in hemoglobin by gas chromatography/mass spectrometry. J Mass Spectrom 34:537-543
32. Iwamoto H, Motomiya Y, Miura K, Morisawa M, Yoshimura Y, Maruyama I (2001) Immunochemical assay of hemoglobin with N-epsilon-(carboxymethyl)lysine at lysine 66 of the beta chain. Clin Chem 47:1249-1255
33. Delpierre G, Vertommen D, Communi D, Rider MH, Van Schaftingen E (2004) Identification of fructosamine residues deglycated by fructosamine-3-kinase in human hemoglobin. J Biol Chem 279:27613-27620
34. Lapolla A, Tubaro M, Reitano R et al (2004) The complexity of non-enzymatic glycation product sets of human globins. Diabetologia 47:1712-1715
35. Thornalley PJ, Argirova M, Ahmed N, Mann VM, Argirov OK, Dawnay A (2000) Mass spectrometric monitoring of albumin in uraemia. Kidney Internat 58:2228-2234
36. Karachalias N, Babaei-Jadidi R, Kupich C, Ahmed N, Thornalley PJ (2005) High dose thiamine therapy counters dyslipidemia and advanced glycation of plasma protein in streptozotocin-induced diabetic rats. Ann NY Acad Sci (in press)
37. Raghothama C, Rao P (1994) Increased proteolysis of oxidatively damaged hemoglobin in erythrocyte lysates in diabetes mellitus. Clin Chem Acta 225:65-70
38. Mitch WE, Bailey JL, Wang X, Jurkovitz C, Newby D, Price SR (1999) Evaluation of signals activating ubiquitin-proteasome proteolysis in a model of muscle wasting. Am J Physiol 276:C1132-C1138
39. Portero-Otin M, Pamplona R, Ruiz M, Cabiscol E, Prat J, Bellmunt MJ (1999) Diabetes induces an impairment in the proteolytic activity against oxidized proteins and a heterogeneous effect in nonenzymatic protein modifications in the cytosol of rat liver and kidney. Diabetes 48:2215-2220
40. Thornalley PJ (1988) Modification of the glyoxalase system in human red blood cells by glucose in vitro. Biochem J 254:751-755
41. Phillips SA, Thornalley PJ (1993) Formation of methylglyoxal and D-lactate in human red blood cells in vitro. Biochem Soc Trans 21:163
42. Phillips SA, Thornalley PJ (1993) The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal. Eur J Biochem 212:101-105
43. Brownlee M (2001) Biochemistry and molecular cell biology of diabetic complications. Nature 414:813-820
44. Du X, Matsumara T, Edelsttein D et al (2003) Inhibition of GAPDH activity by poly(ADP-ribose) polymerase activates three major pathways of hyperglycemic damage in endothelial cells. J Clin Invest 112:1049-1057
45. Reichard GA, Skutches CL, Hoeldtke RD, Owen OE (1986) Acetone metabolism in humans during diabetic ketoacidosis. Diabetes 35:668-674
46. McLellan AC, Thornalley PJ, Benn J, Sonksen PH (1994) The glyoxalase system in clinical diabetes mellitus and correlation with diabetic complications. Clin Sci 87:21-29
47. Thomas MC, Tikellis C, Burns WC et al (2003) Reduced tubular cation transport in diabetes: prevented by ACE inhibition. Kidney Int 63:2152-2161
48. Brot N, Weissbach H (1983) Biochemistry and physiological role of methionine sulfoxide reductase in proteins. Arch Biochem Biophys 253:271-281
49. Pabarcus MK, Casida JE (2002) Kynurenine formamidase: determination of primary structure and modeling-based prediction of tertiary structure and catalytic triad. Biochim Biophys Acta 1596:201-211
50. Ohshima H, Friesen M, Brouet I, Bartsch H (1990) Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem Toxicol 28:647-652
51. Ahmed N, Ahmed U, Thornalley PJ, Hager K, Fleischer GA, Munch G (2004) Protein glycation, oxidation and nitration marker residues and free adducts of cerebrospinal fluid in Alzheimer's disease and link to cognitive impairment. J Neurochem 92: 255-263
52. Ivanov VT, Yatskin ON, Kalinina OA, Philippova MM, Karelin AA, Blishchenko EY (2000) Tissue-specific peptide pools. Generation and function. Pure Appl Chem 72:355-363
53. Greive KA, Balazs NDH, Comper WD (2001) Protein fragments in urine have been considerably underestimated by various protein assays. Clin Chem 47:1717-1719
54. Ceriello A, Mercuri F, Quagliaro L et al (2001) Detection of nitrotyrosine in the diabetic plasma: evidence of oxidative stress. Diabetologia 44:834-838
55. Soriano FG, Virag L, Jagtap P et al (2001) Diabetic endothelial dysfunction: the role of poly(ADP-ribose) polymerase activation. Nat Med 7:108-113
56. Gladwin MT, Lancaster JR, Freeman BA, Schechter AN (2003) Nitric oxide's reactions with hemoglobin: a view through the SNO-storm. Nat Med 9:496-500