Transglycation - A potential new mechanism for deglycation of Schiff's bases

Annals of the New York Academy of Sciences

Volumn 1043, Issue , 2005, Pages 845-864

  Szwergold, Benjamin S ^a   Howell, Scott K ^a   Beisswenger, Paul J ^a  

^a DARTMOUTH MEDICAL SCHOOL   (United States)

Author keywords

FN3K; Fructosamine 3 kinase; Glucose cysteine; Nonenzymatic glycation; Thiazolidine; Transglycation

Indexed keywords

ABC TRANSPORTER; CYSTEINE; FRUCTOSAMINE 3 KINASE; FRUCTOSAMINE 3 KINASE RELATED PROTEIN; GLUCOSE; GLYCOSYLATED HEMOGLOBIN; ISOENZYME; MULTIDRUG RESISTANCE PROTEIN; PHOSPHOTRANSFERASE; SCHIFF BASE; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CONFERENCE PAPER; DIABETES MELLITUS; ERYTHROCYTE; HUMAN; PROTEIN GLYCOSYLATION; REACTION ANALYSIS; TRANSGLYCATION;

EID: 23744507245     PISSN: 00778923     EISSN: None     Source Type: Book Series    
DOI: 10.1196/annals.1333.097     Document Type: Conference Paper

References (55)

1. BUCALA, R. & A. CERAMI. 1992. Advanced glycosylation: chemistry, biology, and implications for diabetes and aging. Adv. Pharmacol. 23: 1-34.
2. SUN, M., M. YOKOYAMA, T. ISHIWATA & G. ASANO. 1998. Deposition of advanced glycation end products (AGE) and expression of the receptor for AGE in cardiovascular tissue of the diabetic rat. Int. J. Exp. Pathol. 79: 207-222.
3. SOULIS, T. et al. 1997. Advanced glycation end products and their receptors co-localise in rat organs susceptible to diabetic microvascular injury. Diabetologia 40: 619-628.
4. SCHMIDT, A.M. & D.M. STERN. 2001. Receptor for age (RAGE) is a gene within the major histocompatibility class III region: implications for host response mechanisms in homeostasis and chronic disease. Front. Biosci. 6: D1151-1160.
5. BEISSWENGER, P.J., B.S. SZWERGOLD & K.T. YEO. 2001. Glycated proteins in diabetes. Clin. Lab. Med. 21: 53-78.
6. KILHOVD, B.K. et al. 2003. Increased serum levels of the specific AGE-compound methylglyoxal-derived hydroimidazolone in patients with type 2 diabetes. Metabolism 52: 163-167.
7. YIM, M.B. et al. 2001. Protein glycation: creation of catalytic sites for free radical generation. Ann. N.Y. Acad. Sci. 928: 48-53.
8. OAK J., K. NAKAGAWA & T. MIYAZAWA. 2000. Synthetically prepared Amadori-glycated phosphatidylethanolamine can trigger lipid peroxidation via free radical reactions. FEBS Lett. 481: 26-30.
9. SZWERGOLD, B.S., S.K. HOWELL & P.J. BEISSWENGER. 2002. Nonenzymatic glycation/enzymatic deglycation. A novel hypothesis on the etiology of diabetic complications. In Proceedings of the 7th International Symposium on Maillard Reaction. S. Horiuchi, N. Taniguchi, F. Hayase, et al., Eds.: 143-152. Elsevier. Amsterdam.
10. SZWERGOLD, B.S. & P.J. BEISSWENGER. 2003. Nonenzymatic glycation-a new paradigm or an epiphenomenon. Biochem. Soc. Trans. 31: 1428-1432.
11. GUMINSKA, M. & J. STERKOWICZ. 1976. Effect of sodium fluoride on glycolysis in human erythrocytes and Ehrlich ascites tumour cells in vitro. Acta Biochim. Pol. 23: 285-291.
12. SZWERGOLD, B.S. et al. 1997. Identification of a novel protein kinase activity specific for Amadori adducts on glycated proteins. Diabetes 46(Suppl. 1): 108A.
13. DELPIERRE, G. et al. 2000. Identification, cloning, and heterologous expression of a mammalian fructosamine-3-kinase. Diabetes 49: 627-634.
14. SZWERGOLD, B.S., S.K. HOWELL & P.J. BEISSWENGER. 2001. Human fructosamine-3-kinase (FN3K): purification, sequencing, substrate specificity and evidence of activity in vivo. Diabetes 50: 2139-2147.
15. DELPIERRE, G., F. COLLARD, J. FORTPIED & E. VAN SCHAFTINGEN. 2002. Fructosamine-3-kinase is involved in an intracellular deglycation pathway in human erythrocytes. Biochem. J. 365: 801-808.
16. DELPIERRE, G. et al. 2004. Identification of fructosamine residues deglycated by fructosamine-3-kinase in human hemoglobin. J. Biol. Chem. 279: 27613-27620.
17. KATO, H. et al. 1990. Metabolism of 3-deoxyglucosone, an intermediate compound in the Maillard reaction, administered orally or intravenously to rats. Biochem. Biophys. Acta 1035: 71-76.
18. OIMOMI, M. et al. 1989. Purification of alpha-ketoaldehyde dehydrogenase from the human liver and its possible significance in the control of glycation. Experientia 45: 463-466.
19. COLLARD, F. et al. 2003. A mammalian protein homologous to fructosamine-3-kinase is a ketosamine-3-kinase acting on psicosamines and ribulosamines but not on fructosamines. Diabetes 52: 2888-2895.
20. CONNER, J.R., P.J. BEISSWENGER & B.S. SZWERGOLD. 2004. The expression of the genes for fructosamine-3-kinase and fructosamine-3-kinase-related protein appears to be constitutive and unaffected by environmental signals. Biochem. Biophys. Res. Comm. 323: 932-936.
21. DELPLANQUE, J., G. DELPIERRE, F.R. OPPERDOES & E. VAN SCHAFTINOEN. 2004. Tissue distribution and evolution of fructosamine-3-kinase and fructosamine-3-kinase-related protein. J. Biol. Chem. 279: 46606-46613. Epub 2004 Aug 25.
22. CONNER, J.R., P.J. BEISSWENGER & B.S. SZWERGOLD. 2005. Some clues as to the regulation, expression, function, and distribution of fructosamine-3-kinase and fructosamine-3-kinase-related protein. Ann. N.Y. Acad. Sci. 1043: 824-836.
23. ROHLFING, C.L. et al. 2002. Defining the relationship between plasma glucose and HbA(Ic): analysis of glucose profiles and HbA(1c) in the Diabetes Control and Complications Trial. Diabetes Care 25: 275-278
24. MORTENSEN, H.B. & M.O. MARSHAL. 1983. Effect of saline incubation on red cell content of glucosylated haemoglobins studied by iso-electric focusing. Clin. Chim. Acta 132: 213-217.
25. BREITLING-UTZMANN, C.M., A. UNGER, D.A. FRIEDL & M.O. LEDERER. 2001. Identification and quantification of phosphatidylethanolamine-derived glucosylamines and aminoketoses from human erythrocytes-influence of glycation products on lipid peroxidation. Arch. Biochem. Biophys. 391: 245-254.
26. HOLTJE, J.V. 1996. Lytic transglycosylases. EXS 75: 425-429.
27. HOLDEN, J.T. 1962. Amino Acid Pools-Distribution, Formation and Function of Free Amino Acids. Elsevier. Amsterdam.
28. MEDINA, M.A. 2003. et al. Biogenic amines and polyamines: similar biochemistry for different physiological missions and biomedical applications. Crit. Rev. Biochem. Mol. Biol. 38: 23-59.
29. POWIS, G., M. BRIEHL & J. OBLONG. 1995. Redox signalling and the control of cell growth and death. Pharmacol. Ther. 68: 149-173.
30. MEISTER, A. & M.E. ANDERSON. 1983. Glutathione. Ann. Rev. Biochem. 52: 711-760.
31. FREEDMAN, J.C. 1983. Partial requirement of in vitro survival of human red blood cells. J. Membr. Biol. 75: 225-231.
32. ABRAHAM, E.C., R.E. PERRY & M. STALLINGS. 1983. Application of affinity chromatography for separation and quantitation of glycosylated hemoglobins. J. Lab. Clin. Med. 102: 187-197.
33. MOSSINE, V.V., G.V. GLINSKY & M.S. FEATHER. 1994. The preparation and characterization of some Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) derived from a series of aliphatic omega-amino acids. Carbohydr. Res. 262: 257-270.
34. NEGLIA, C.I. et al. 1985. Characterization of glycated proteins by 13C NMR spectroscopy. Identification of specific sites of protein modification by glucose. J. Biol. Chem. 260: 5406-5410.
35. CHOI, B.H., S. YEE & M. ROBLES. 1996. The effects of glutathione glycoside in methyl mercury poisoning. Toxicol Appl. Pharmacol. 141: 357-364.
36. WLODEK, L. 1988. The reaction of sulfhydryl groups with carbonyl compounds. Acta Biochim. Pol. 35: 307-317.
37. YAO, W.B. et al. 1997. Protective effect of glucose-cysteine adduct on the in situ perfused rat liver. Amino Acids 12: 33-40.
38. RAPPA, G., A. LORICO, R.A. FLAVELL & A.C. SARTORELLI. 1997. Evidence that the multidrug resistance protein (MRP) functions as a co-transporter of glutathione and natural product toxins. Cancer Res. 57: 5232-5237.
39. SRIVASTAVA, S. et al. 2001. Identification of biochemical pathways for the metabolism of oxidized low-density lipoprotein derived aldehyde-4-hydroxy trans-2-nonenal in vascular smooth muscle cells. Atherosclerosis 158: 339-350
40. JAIN, S.K. 1998. Glutathione and glucose-6-phosphate dehydrogenase deficiency can increase protein glycosylation. Free Radic. Biol. Med. 24: 197-201.
41. BOBROWSKA-HAGERSTRAND, M. et al. 2001. Monitoring of MRP-like activity in human erythrocytes: inhibitory effects of isoflavones. Blood Cells Mol. Dis. 27: 894-900.
42. BAGRIJ, T., A. KLOKOUZAS, S.B. HLADKY & M.A. BARRAND. 2001. Influences of glutathione on anionic substrate efflux in tumour cells expressing the multidrug resistance-associated protein, MRP-1. Biochem. Pharmacol. 62: 199-206.
43. LEHMANN, T. et al. 2001. Expression of MRP1 and related transporters in human lung cells in culture. Toxicology 167: 59-72.
44. KLOKOUZAS, A., M.A. BARRAND & S.B. HLADKY. 2001. Effect of clotrimazole on transport mediated by multidrug resistance associated proteins (MRP1) in human erythrocytes and tumour cells. Eur. J. Biochem. 268: 6569-6577.
45. MURAKAMI, K. 1991. Glutathione metabolism in erythrocytes from patients with diabetes mellitus. Hokkaido Igaku Zasshi 66: 29-40.
46. THORNALLEY, P.J. et al. 1996. Negative association between erythrocyte reduced glutathione concentrations and diabetic complications. Clin. Sci. 91: 575-582.
47. BEUTLER, E. 2001. Composition of the erythrocyte. In Williams Hematology, 6th edit. E, Beutler et al., Eds; 289-294. McGraw-Hill. New York.
48. BARBEHENN, R.V. 2003. Antioxidants in grasshoppers: higher levels defend the midgut tissues of a polyphagous species than a graminivorous species. J. Chem. Ecol. 29: 683-702.
49. WOODRING, J.P. 1985. In Fundamentals of Insect Physiology. M.S. Blum, Ed.: 46-49. John Wiley & Sons. New York.
50. MANNERVIK, B. et al. 1990. Glutathione-linked enzymes in normal and tumor cells and their role in resistance against genotoxic agents. Princess Takamatsu Symp. 21: 253-262.
51. THORNALLEY, P.J. 1998. Glutathione-dependent detoxification of alpha-oxoaldehydes by the glyoxalase system: involvement in disease mechanisms and antiproliferative activity of glyoxalase I inhibitors. Chem. Biol. Interact. 111-112: 137-151.
52. HOMOLYA, L., A. VARADI & B. SARKADI. 2003. Multidrug resistance-associated proteins: export pumps for conjugates with glutathione, glucuronate or sulfate. Biofactors 17: 103-114.
53. STRANGE, R.C., M.A. SPITERI, S. RAMACHANDRAN & A.A. FRYER 2001. Glutathione-S-transferase family of enzymes. Mutat. Res. 482: 21-26.
54. SHAW, L.M. & D.A. NEWMAN. 1979. Hydrolysis of glutathione by human liver gamma-glutamyltransferase. Clin. Chem. 25: 75-79.
55. JOSCH, C., L.O. KLOTZ & H. SIES. 2003. Identification of cytosolic leucyl aminopeptidase (EC 3.4.11.1) as the major cysteinylglycine-hydrolysing activity in rat liver. Biol. Chem. 384: 213-218.