Perturbation of human coronary artery endothelial cell redox state and NADPH generation by methylglyoxal

PLoS ONE

Volumn 9, Issue 1, 2014, Pages

  Morgan, Philip E ^a,b   Sheahan, Pamela J ^a,b   Davies, Michael J ^a,b  

^a HEART RESEARCH INSTITUTE   (Australia)

^b University of Sydney   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

6 N CARBOXYMETHYLLYSINE; ADVANCED GLYCATION END PRODUCT; ALDEHYDE; DEOXYGLUCOSE 6 PHOSPHATE; DIAMINO ACID; GLUCOSE; GLUCOSE 6 PHOSPHATE; GLUTATHIONE; GLYCOLALDEHYDE; GLYOXAL; HYDROIMIDAZOLONE DERIVATIVE; IMIDAZOLE DERIVATIVE; ISOCITRATE DEHYDROGENASE; MALATE DEHYDROGENASE (DECARBOXYLATING); METHYLGLYOXAL; N EPSILON (CARBOXYETHYL)LYSINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUGAR PHOSPHATE; THIOL; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATHEROGENESIS; ATHEROSCLEROSIS; CELL DEATH; CELL LYSATE; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CORONARY ARTERY ENDOTHELIAL CELL; DIABETES MELLITUS; ENDOTHELIAL DYSFUNCTION; ENDOTHELIUM CELL; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; OXIDATION REDUCTION STATE; PROTEIN DEPLETION; SIGNAL TRANSDUCTION;

ALDEHYDES; ARGININE; CELLS, CULTURED; CORONARY VESSELS; ENDOTHELIAL CELLS; GLUCOSE-6-PHOSPHATE; GLUTATHIONE; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; NADP; OXIDATION-REDUCTION; PYRUVALDEHYDE; SULFHYDRYL COMPOUNDS;

EID: 84904995122     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0086564     Document Type: Article

References (45)

1. Barr ELM, Zimmet PZ, Welborn TA, Jolley D, Magliano DJ, et al. (2007) Risk of cardiovascular and all-cause mortality in individuals with diabetes mellitus, impaired fasting glucose, and impaired glucose tolerance: the Australian Diabetes, Obesity, and Lifestyle Study (AusDiab). Circulation 116: 151-157. (Pubitemid 47057520)
2. Ellis EM (2007) Reactive carbonyls and oxidative stress: Potential for therapeutic intervention. Pharmacology & Therapeutics 115: 13-24.
3. Thorpe S, Baynes J (2003) Maillard reaction products in tissue proteins: new products and new perspectives. Amino Acids 25: 275-281. (Pubitemid 38041265)
4. Kalapos MP (2013) Where does plasma methylglyoxal originate from? Diabetes Res Clin Pract 99: 260-271.
5. Lu JX, Randell E, Han YC, Adeli K, Krahn J, et al. (2011) Increased plasma methylglyoxal level, inflammation, and vascular endothelial dysfunction in diabetic nephropathy. Clin Biochem 44: 307-311.
6. Han Y, Randell E, Vasdev S, Gill V, Gadag V, et al. (2007) Plasma methylglyoxal and glyoxal are elevated and related to early membrane alteration in young, complication-free patients with type 1 diabetes. Mol Cell Biochem 305: 123-131. (Pubitemid 47517175)
7. Lapolla A, Flamini R, Tonus T, Fedele D, Senesi A, et al. (2003) An effective derivatization method for quantitative determination of glyoxal and methylglyoxal in plasma samples by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom 17: 876-878. (Pubitemid 36433174)
8. Nagai R, Matsumoto K, Ling X, Suzuki H, Araki T, et al. (2000) 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: 1714-1723.
9. Rabbani N, Thornalley PJ (2012) Methylglyoxal, glyoxalase 1 and the dicarbonyl proteome. Amino Acids 42: 1133-1142.
10. Nelson DL, Cox MM (2000) Lehninger principles of biochemistry. New York: Worth Publisher.
11. Vander Jagt DL, Hunsaker LA (2003) Methylglyoxal metabolism and diabetic complications: roles of aldose reductase, glyoxalase-I, betaine aldehyde dehydrogenase and 2-oxoaldehyde dehydrogenase. Chem Biol Interact 143-144: 341-351. (Pubitemid 36253593)
12. Ahmed N (2005) Advanced glycation endproducts: role in pathology of diabetic complications. Diabetes Res Clin Pract 67: 3-21.
13. Dyer DG, Dunn JA, Thorpe SR, Bailie KE, Lyons TJ, et al. (1993) Accumulation of Maillard reaction products in skin collagen in diabetes and aging. J Clin Invest 91: 2463-2469. (Pubitemid 23182497)
14. Morgan PE, Dean RT, Davies MJ (2002) Inactivation of cellular enzymes by carbonyls and protein-bound glycation/glycoxidation products. Arch Biochem Biophys 403: 259-269. (Pubitemid 34800207)
15. Moheimani F, Morgan PE, van Reyk DM, Davies MJ (2010) Deleterious effects of reactive aldehydes and glycated proteins on macrophage proteasomal function: possible links between diabetes and atherosclerosis. Biochim Biophys Acta 802: 561-571.
16. Zeng J, Dunlop RA, Rodgers KJ, Davies MJ (2006) Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols. Biochem J 398: 197-206. (Pubitemid 44338476)
17. Jandeleit-Dahm K, Watson A, Soro-Paavonen A (2008) The AGE/RAGE axis in diabetes-accelerated atherosclerosis. Clin Exp Pharmacol Physiol 35: 329-334. (Pubitemid 351260012)
18. Wild R, Ooi L, Srikanth V, Münch G (2012) A quick, convenient and economical method for the reliable determination of methylglyoxal in millimolar concentrations: the N-acetyl-L-cysteine assay. Anal Bioanal Chem 403: 2577-2581.
19. Morgan PE, Sheahan PJ, Pattison DI, Davies MJ (2013) Methylglyoxal- induced modification of arginine residues decreases the activity of NADPH-generating enzymes. Free Radic Biol Med 61: 229-242.
20. Kalapos MP (1999) Methylglyoxal in living organisms: chemistry, biochemistry, toxicology and biological implications. Toxicol Lett 110: 145-175.
21. Morgan PE, Pattison DI, Davies MJ (2012) Quantification of hydroxyl radical-derived oxidation products in peptides containing glycine, alanine, valine, and proline. Free Radic Biol Med 52: 328-339.
22. Hawkins CL, Morgan PE, Davies MJ (2009) Quantification of protein modification by oxidants. Free Radic Biol Med 46: 965-988.
23. Zeng J, Davies MJ (2005) 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 18: 1232-1241. (Pubitemid 41170247)
24. Sell DR, Monnier VM (2004) Conversion of arginine into ornithine by advanced glycation in senescent human collagen and lens crystallins. J Biol Chem 279: 54173-54184. (Pubitemid 40053153)
25. Ahmed N, Argirov O, Minhas H, Cordeiro C, Thornalley P (2002) 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 N ε-(1-carboxyethyl)lysine-modified albumin. Biochem J 364: 1-14.
26. Banhegyi G, Csala M, Benedetti A (2009) Hexose 6-phosphate dehydrogenase: linking endocrinology and metabolism in the endoplasmic reticulum. J Mol Endocrinol 42: 283-289.
27. Lapolla A, Flamini R, Dalla Vedova A, Senesi A, Reitano R, et al. (2003) Glyoxal and methylglyoxal levels in diabetic patients: quantitative determination by a new GC/MS method. Clin Chem Lab Med 41: 1166-1173. (Pubitemid 37265695)
28. Thornalley PJ (1996) Pharmacology of methylglyoxal. Formation, modification of proteins and nucleic acids, and enzymatic detoxification: a role in pathogenesis and antiproliferative chemotherapy. Gen Pharmacol 27: 565-573.
29. Haik G, Lo T, Thornalley P (1994) Methylglyoxal concentration and glyoxalase activities in the human lens. Exp Eye Res 59: 497-500. (Pubitemid 24352084)
30. Lo TWC (1994) Binding and modification of proteins by methylglyoxal under physiological conditions. A kinetic and mechanistic study with Nα-acetylarginine, Nα-acetylcysteine, and Nα-acetyllysine, and bovine serum albumin. J Biol Chem 269: 32299-32305.
31. Oba T, Tatsunami R, Sato K, Takahashi K, Hao ZH, et al. (2012) Methylglyoxal has deleterious effects on thioredoxin in human aortic endothelial cells. Environ Toxicol Pharmacol 34: 117-126.
32. Tatsunami R, Oba T, Takahashi K, Tampo Y (2009) Methylglyoxal causes dysfunction of thioredoxin and thioredoxin reductase in endothelial cells. J Pharmacol Sci 111: 426-432.
33. Frey RS, Ushio-Fukai M, Malik AB (2009) NADPH oxidase-dependent signaling in endothelial cells: role in physiology and pathophysiology. Antioxid Redox Signal 11: 791-810.
34. Zhao W, Devamanoharan P, Varma S (1998) Fructose induced deactivation of glucose 6-phosphate dehydrogenase activity and its prevention by pyruvate: implications in cataract prevention. Free Radic Res 29: 315-320. (Pubitemid 29027451)
35. Diaz-Flores M, Ibanez-Hernandez M, Galvan R, Gutierrez M, Duran-Reyes G, et al. (2006) Glucose 6-phosphate dehydrogenase activity and NADPH/NADP + ratio in liver and pancreas are dependent on the severity of hyperglycemia in rat. Life Sci 78: 2601-2607.
36. Jain M, Brenner DA, Cui L, Lim CC, Wang B, et al. (2003) Glucose 6-phosphate dehydrogenase modulates cytosolic redox status and contractile phenotype in adult cardiomyocytes. Circ Res 93: e9-16.
37. Gupte RS, Ata H, Rawat D, Abe M, Taylor MS, et al. (2011) Glucose 6-phosphate dehydrogenase is a regulator of vascular smooth muscle contraction. Antioxid Redox Signal 14: 543-558.
38. Matsui R, Xu S, Maitland KA, Mastroianni R, Leopold JA, et al. (2006) Glucose 6-phosphate dehydrogenase deficiency decreases vascular superoxide and atherosclerotic lesions in apolipoprotein E-/- mice. Arterioscler Thromb Vasc Biol 26: 910-916. (Pubitemid 43732171)
39. Lee S, Koh H, Park D, Song B, Huh T, et al. (2002) Cytosolic NADP +-dependent isocitrate dehydrogenase status modulates oxidative damage to cells. Free Radic Biol Med 32: 1185-1196.
40. Thornalley P, Battah S, Ahmed N, Karachalias N, Agalou S, et al. (2003) Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry. Biochem J 375: 581-592. (Pubitemid 37433506)
41. Nitenberg A, Cosson E, Pham I (2006) Postprandial endothelial dysfunction: role of glucose, lipids and insulin. Diabetes Metab 32: 2S28-33.
42. Kim KM, Kim YS, Jung DH, Lee J, Kim JS (2012) Increased glyoxalase I levels inhibit accumulation of oxidative stress and an advanced glycation end product in mouse mesangial cells cultured in high glucose. Exp Cell Res 318: 152-159.
43. Barati MT, Merchant ML, Kain AB, Jevans AW, McLeish KR, et al. (2007) Proteomic analysis defines altered cellular redox pathways and advanced glycation end-product metabolism in glomeruli of db/db diabetic mice. Am J Physiol Renal Physiol 293: F1157-F1165. (Pubitemid 47583949)
44. World Health Organization (2004) Diabetes Action Now : An initiative of the World Health Organization and the International Diabetes Federation. Geneva.
45. Schafer FQ, Buettner GR (2004) Redox state and redox environment in biology. In: Forman HJ, Fukuto J, Torres M, editors. Signal transduction by reactive oxygen and nitrogen species: pathways and chemical principles: Springer Netherlands. 1-14.