Protein glycation in Saccharomyces cerevisiae: Argpyrimidine formation and methylglyoxal catabolism

FEBS Journal

Volumn 272, Issue 17, 2005, Pages 4521-4531

  Gomes, Ricardo A ^a   Silva, Marta Sousa ^a   Vicente Miranda, Hugo ^a   Ferreira, António E N ^a   Cordeiro, Carlos A A ^a   Freire, Ana Ponces ^a  

^a UNIVERSITY OF LISBON   (Portugal)

Author keywords

Aldose reductase; Glycation; Glyoxalase I; Methylglyoxal; Yeast

Indexed keywords

ADVANCED GLYCATION END PRODUCT; ALDEHYDE REDUCTASE; ANTIBODY; ARGININE; BIOLOGICAL MARKER; GLUCOSE; GLUTATHIONE; METHYLGLYOXAL; PHOSPHATE; PYRIMIDINE; TRIOSE;

ALZHEIMER DISEASE; ARTICLE; CATABOLISM; DEGENERATIVE DISEASE; DELETION MUTANT; DIABETES MELLITUS; EUKARYOTIC CELL; FAMILIAL AMYLOID POLYNEUROPATHY; FUNGAL STRAIN; GENE DELETION; GLYCOLYSIS; GROWTH CURVE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; NONHUMAN; PARKINSON DISEASE; PRIORITY JOURNAL; PROTEIN GLYCOSYLATION; PROTEIN MODIFICATION; SACCHAROMYCES CEREVISIAE; STEADY STATE;

EUKARYOTA; SACCHAROMYCES CEREVISIAE;

EID: 24644494767     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2005.04872.x     Document Type: Article

References (39)

1. Brownlee M (1995) Advanced protein glycosylation in diabetes and aging. Annu Rev Med 46, 223-234.
2. Bucala R & Cerami A (1992) Advanced glycosylation: chemistry, biology, and implications for diabetes and aging. Adv Pharmacol 23, 1-34.
3. Bouma B, Kroon-Batenburg LM, Wu YP, Brunjes B, Posthuma G, Kranenburg O, de Groot PG, Voest EE & Gebbink MF (2003) Glycation induces formation of amyloid cross-beta structure in albumin. J Biol Chem 278, 41810-41819.
4. Du Yan S, Zhu H, Fu J, Yan SF, Roher A, Tourtellotte WW, Rajavashisth T, Chen X, Godman GC, Stern D & Schmidt AM (1997) Amyloid-beta peptide-receptor for advanced glycation endproduct interaction elicits neuronal expression of macrophage-colony stimulating factor: a proinflammatory pathway in Alzheimer disease. Proc Natl Acad Sci USA 94, 5296-5301.
5. Chen F, Wollmer MA, Hoerndli F, Munch G, Kuhla B, Rogaev EI, Tsolaki M, Papassotiropoulos A & Gotz J (2004) Role for glyoxalase I in Alzheimer's disease. Proc Natl Acad Sci USA 101, 7687-7692.
6. Vitek MP, Bhattacharya K, Glendening JM, Stopa E, Vlassara H, Bucala R, Manogue K & Cerami A (1994) Advanced glycation end products contribute to amyloidosis in Alzheimer disease. Proc Natl Acad Sci USA 91, 4766-4770.
7. Gomes R, Sousa Silva M, Quintas A, Cordeiro C, Freire A, Pereira P, Martins A, Monteiro E, Barroso E & Ponces Freire A (2005) Argpyrimidine, a methylglyoxal-derived advanced glycation end-product in familial amyloidotic polyneuropathy. Biochem J 385, 339-345.
8. Castellani R, Smith MA, Richey PL & Perry G (1996) Glycoxidation and oxidative stress in Parkinson disease and diffuse Lewy body disease. Brain Res 737, 195-200.
9. Yan SD, Chen X, Schmidt AM, Brett J, Godman G, Zou YS, Scott CW, Caputo C, Frappier T & Smith MA (1994) Glycated tau protein in Alzheimer disease: a mechanism for induction of oxidant stress. Proc Natl Acad Sci USA 91, 7787-7791.
10. Richard JP (1993) Mechanism for the formation of methylglyoxal from triosephosphates. Biochem Soc Trans 21, 549-553.
11. Booth AA, Khalifah RG, Todd P & Hudson BG (1997) In vitro kinetic studies of formation of antigenic advanced glycation end products (AGEs). Novel inhibition of post-Amadori glycation pathways. J Biol Chem 272, 5430-5437.
12. Thornalley PJ (1999) Clinical significance of glycation. Clin Laboratory 45, 263-273.
13. Westwood ME & Thornalley PJ (1997) Glycation and advanced glycation endproducts. In: The glycation hypothesis of atherosclerosis (Colaco C, ed), pp. 57-87. RG Landes, Georgetown, USA.
14. Shipanova IN, Glomb MA & Nagaraj RH (1997) Protein modification by methylglyoxal: chemical nature and synthetic mechanism of a major fluorescent adduct. Arch Biochem Biophys 344, 29-36.
15. Oya T, Hattori N, Mizuno Y, Miyata S, Maeda S, Osawa T & Uchida K (1999) Methylglyoxal modification of protein. Chemical and immunochemical characterization of methylglyoxal-arginine adducts. J Biol Chem 274, 18492-18502.
16. Ahmed MU, Brinkmann Frye E, Degenhardt TP, Thorpe SR & Baynes JW (1997) N-epsilon-(carboxyethyl) lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Biochem J 324, 565-570.
17. Padival AK, Crabb JW & Nagaraj RH (2003) Methylglyoxal modifies heat shock protein 27 in glomerular mesangial cells. FEBS Lett 551, 113-118.
18. Sakamoto H, Mashima T, Yamamoto K & Tsuruo T (2002) Modulation of heat-shock protein 27 (Hsp27) anti-apoptotic activity by methylglyoxal modification. J Biol Chem 277, 45770-45775.
19. Racker E (1951) The mechanism of action of glyoxalase. J Biol Chem 190, 685-696.
20. 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.
21. Martins AM, Cordeiro CA & Ponces Freire AM (2001) In situ analysis of methylglyoxal metabolism in Saccharomyces cerevisiae. FEBS Lett 499, 41-44.
22. Moye-Rowley WS (2003) Regulation of the transcriptional response to oxidative stress in fungi: similarities and differences. Eukaryot Cell 2, 381-389.
23. Maeta K, Izawa S, Okazaki S, Kuge S & Inoue Y (2004) Activity of the Yap1 transcription factor in Saccharomyces cerevisiae is modulated by methylglyoxal, a metabolite derived from glycolysis. Mol Cell Biol 24, 8753-8764.
24. Aguilera J & Prieto JA (2001) The Saccharomyces cerevisiae aldose reductase is implied in the metabolism of methylglyoxal in response to stress conditions. Curr Genet 39, 273-283.
25. Aguilera J & Prieto JA (2004) Yeast cells display a regulatory mechanism in response to methylglyoxal. FEMS Yeast Res 4, 633-641.
26. Inoue Y, Tsujimoto Y & Kimura A (1998) Expression of the glyoxalase I gene of Saccharomyces cerevisiae is regulated by high osmolarity glycerol mitogen-activated protein kinase pathway in osmotic stress response. J Biol Chem 273, 2977-2983.
27. Shinohara M, Thornalley PJ, Giardino I, Beisswenger P, Thorpe SR, Onorato J & Brownlee M (1998) Over-expression of glyoxalase-I in bovine endothelial cells inhibits intracellular advanced glycation endproduct formation and prevents hyperglycemia-induced increases in macromolecular endocytosis. J Clin Invest 101, 1142-1147.
28. Vander Jagt DL, Robinson B, Taylor KK & Hunsaker LA (1992) Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications. J Biol Chem 267, 4364-4369.
29. Van Herreweghe F, Mao J, Chaplen FW, Grooten J, Gevaert K, Vandekerckhove J & Vancompernolle K (2002) Tumor necrosis factor-induced modulation of glyoxalase I activities through phosphorylation by PKA results in cell death and is accompanied by the formation of a specific methylglyoxal-derived AGE. Proc Natl Acad Sci USA 99, 949-954.
30. Kellum MW, Oray B & Norton SJ (1978) A convenient quantitative synthesis of methylglyoxal for glyoxalase I assays. Anal Biochem 85, 586-590.
31. McLellan AC, Phillips SA & Thornalley PJ (1992) The assay of methylglyoxal in biological systems by derivatization with 1,2-diamino-4,5- dimethoxybenzene. Anal Biochem 206, 17-23.
32. Cordeiro C & Ponces Freire A (1996) Methylglyoxal assay in cells as 2-methylquinoxaline using 1,2-diamino-benzene as derivatizing reagent. Anal Biochem 234, 221-224.
33. Sousa Silva M, Ferreira AEN, Tomás AM, Cordeiro C & Ponces Freire A (2005) Quantitative assessment of the glyoxalase pathway in Leishmania infantum as a therapeutic target by modelling and computer simulation. FEBS J 272, 2388-2398.
34. Ausubel FM, Brent R, Kingston RE, Moore DD, Seidman JG, Smith JA & Struhl K (1990) Current Protocols in Molecular Biology. John Wiley Sons Inc, New York.
35. Martins AM, Mendes P, Cordeiro C & Freire AP (2001) In situ kinetic analysis of glyoxalase I and glyoxalase II in Saccharomyces cerevisiae. Eur J Biochem 268, 3930-3936.
36. Vaseghi S, Baumeister A, Rizzi M & Reuss M (1999) In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae. Metab Eng 1, 128-140.
37. Hynne F, Dano S & Sorensen PG (2001) Full-scale model of glycolysis in Saccharomyces cerevisiae. Biophys Chem 94, 121-163.
38. Storn R & Price K (1997) Differential evolution - A simple and efficient heuristic for global optimization over continuous spaces. J Global Optimiz 11, 341-359.
39. Abecasis J, Ferreira AEN & Ponces Freire A (2004) Metabolic modelling using evolutionary algorithms. Eur J Biochem 271 (Suppl. 1), 88.