Sequestering Agents of Intermediate Reactive Aldehydes as Inhibitors of Advanced Lipoxidation End-Products (ALEs)

Redox Proteomics: From Protein Modifications to Cellular Dysfunction and Diseases

Volumn , Issue , 2006, Pages 877-929

  Carini, Marina ^a   Aldini, Giancarlo ^a   Facino, Roberto Maffei ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Advanced lipoxidation end products (ALEs) inhibitors; Lipoxidation (oxidation of polyunsaturated fatty acids, PUFAs); Lipoxidation derived reactive aldehydes

Indexed keywords

EID: 33749003809     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/0471973122.ch27     Document Type: Chapter

References (213)

1. Abe H. (2000). Role of histidine-related compounds as intracellular proton buffering constituents in vertebrate muscle. Biochemistry (Mosc) 65: 757-765.
2. Aberle N.S. 2nd, Picklo M.J. Sr, Amarnath V., Ren J. (2004). Inhibition of cardiac myocyte contraction by 4-hydroxy-trans-2-nonenal. Cardiovasc Toxicol 4: 21-28.
3. Aksenov M.Y., Aksenova M.V., Butterfield D.A., Geddes J.W., Markesbery W.R. (2001). Protein oxidation in the brain in Alzheimer's disease. Neuroscience 103: 373-383.
4. Al-Abed Y., Bucala R. (1997). Efficient scavenging of fatty acid oxidation products by aminoguanidine. Chem Res Toxicol 10: 875-879.
5. Alary J., Gueraud F., Cravedi J.P. (2003). Fate of 4-hydroxynonenal in vivo: Disposition and metabolic pathways. Mol Aspects Med 24: 177-187.
6. Alderson N.L., Chachich M.E. Youssef N.N., Beattie R.J., Nachtigal M., Thorpe S.R., Baynes J.W. (2003). The AGE inhibitor pyridoxamine inhibits lipemia and development of renal and vascular disease in Zucker obese rats. Kidney Int 63: 2123-2133.
7. Alderson N.L., Chachich M.E., Frizzell N., Canning P., Metz T.O., Januszewski A.S., Youssef N.N., Stitt A.W., Baynes J.W., Thorpe S.R. (2004). Effect of antioxidants and ACE inhibition on chemical modification of proteins and progression of nephropathy in the streptozotocin diabetic rat. Diabetologia 47: 1385-1395.
8. Aldini G., Carini M., Beretta G., Bradamante S., Facino R.M. (2002a) Carnosine is a quencher of 4-hydroxy-nonenal: Through what mechanism of reaction? Biochem Biophys Res Commun 298: 699-706.
9. Aldini G., Granata P., Carini M. (2002b). Detoxification of cytotoxic α,β-unsaturated aldehydes by carnosine: Characterization of conjugated adducts by electrospray ionization tandem mass spectrometry and detection by liquid chromatography/mass spectrometry in rat skeletal muscle. J Mass Spectrom 37: 1219-1228.
10. Aldini G., Granata P., Orioli M., Santaniello E., Carini M. (2003). Detoxification of 4-hydroxynonenal (HNE) in keratinocytes: Characterization of conjugated metabolites by liquid chromatography/elecytrospray ionization tandem mass spectrometry. J Mass Spectrom 38: 1160-1168.
11. Aldini G, Orioli M, Carini M, Maffei Facino R. (2004). Profiling histidine-containing dipeptides in rat tissues by liquid chromatography/electrospray ionization tandem mass spectrometry. J Mass Spectrom 39: 1417-1428.
12. Aldini G., Dalle-Donne I., Vistoli G., Maffei Facino R., Carini M. (2005). Covalent modification of actin by 4-hydroxy-trans-2-nonenal (HNE): LC-ESI-MS/MS evidence for cys374 Michael adduction. J Mass Spectrom 40: 946-954.
13. Al-Rawithi S., El-Yazigi A., Ernst P., Al-Fiar F., Nicholls P.J. (1998). Urinary excretion and pharmacokinetics of acrolein and its parent drug cyclophosphamide in bone marrow transplant patients. Bone Marrow Transplant 22: 485-490.
14. Alt N., Carson J.A., Alderson N.L., Wang Y., Nagai R., Henle T., Thorpe S.R., Baynes J.W. (2004). Chemical modification of muscle protein in diabetes. Arch Biochem Biophys 425: 200-206.
15. Amarnath V., Amarnath K., Amarnath K., Davies S., Roberts L.J. 2nd. (2004). Pyridoxamine: An extremely potent scavenger of 1,4-dicarbonyls. Chem Res Toxicol 173: 410-415.
16. Anderson M.M., Hazen S.L., Hsu F.F., Heinecke J.W. (1997). Human neutrophils employ themyeloperoxidase-hydrogen peroxide-chloride system to convert hydroxy-amino acids into glycolaldehyde, 2-hydroxypropanal, and acrolein: A Mechanism for the generation of highly reactive α-hydroxy and α,β-unsaturated aldehydes by phagocytes at sites of inflammation. J Clin Invest 9: 424-432.
17. Arikketh D., Niranjali S., Devaraj H. (2004). Detection of acrolein-lysine adducts in plasma low-density lipoprotein and in aorta of cyclophosphamide-administered rats Arch Toxicol 78: 397-401.
18. Babizhayev M.A., Deyev A.I., Yermakova V.N., Brikman I.V., Bours J. (2004). Lipid peroxidation and cataracts: N-Acetylcarnosine as a therapeutic tool to manage agerelated cataracts in human and in canine eyes. Drugs RD 5: 125-139.
19. Baynes J.W., Thorpe S.R. (1999). Role of oxidative stress in diabetic complications: A new perspective on an old paradigm. Diabetes 48: 1-9.
20. Baynes J.W., Thorpe S.R. (2000). Glycoxidation and lipoxidation in atherogenesis. Free Radic Biol Med 28: 1708-1716.
21. Baynes J.W. (2003). Chemical modification of proteins by lipids in diabetes. Clin Chem Lab Med 41: 1159-1165.
22. Bolton W.K., Cattran D.C., Williams M.E., Adler S.G., Appel G.B., Cartwright K., Foiles P.G., Freedman B.I., Raskin P., Ratner R.E., Spinowitz B.S., Whittier F.C.,Wuerth J.P. (2004). ACTION I Investigator GroupRandomized trial of an inhibitor of formation of advanced glycation end products in diabetic nephropathy. Am J Nephrol 24: 32-40.
23. Bonfanti L., Peretto P., De Marchis S., Fasolo A. (1999). Carnosine-related dipeptides in the mammalian brain. Prog Neurobiol 59: 333-353.
24. Bonnefont-Rousselot D. (2003). Advanced glycation end products: Production and pathophysiological significance. Cahiers de Nutrition et de Dietetique 38: 122-129.
25. Booth A.A., Khalifah R.G., Hudson B.G. (1996). Thiamine pyrophosphate and pyridoxamine inhibit the formation of antigenic advanced glycation end-products: Comparison with aminoguanidine. Biochem Biophys Res Commun 20: 113-119.
26. Booth A.A., Khalifah R.G., Todd P., Hudson B.G. (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.
27. Boscia F., Grattagliano I., Vendemiale G., Micelli-Ferrari T., Altomare E. (2000). Protein oxidation and lens opacity in humans. Invest Ophthalmol Vis Sci 41: 2461-2465.
28. Brownlee M., Vlassara H., Kooney A., Ulrich P., Cerami A. (1986). Aminoguanidine prevents diabetes-induced arterial wall protein cross-linking. Science 232: 1629-1632.
29. Burcham P.C., Kerr P.G., Fontaine F. (2000). The antihypertensive hydralazine is an efficient scavenger of acrolein. Redox Rep 5: 47-49.
30. Burcham P.C., Kaminskas L.M., Fontaine F.R., Petersen D.R., Pyke S.M. (2002). Aldehyde-sequestering drugs: tools for studying protein damage by lipid peroxidation products. Toxicology 181-182: 229-236.
31. Burcham P.C., Fontaine F.R., Kaminskas L.M., Petersen D.R., Pyke S.M. (2004). Protein adduct-trapping by hydrazinophthalazine drugs: Mechanisms of cytoprotection against acrolein-mediated toxicity. Mol Pharmacol 65: 655-664.
32. Burtis C.A., Ashwood E.R. (1999). Tietz Textbook of Clinical Chemistry, 3rd ed., W.B. Saunders, Philadelphia.
33. Calingasan N.Y., Uchida K., Gibson G.E. (1999). Protein-bound acrolein: a novel marker of oxidative stress in Alzheimer's disease. J Neurochem 72: 751-756.
34. Carini M., Aldini G, Maffei Facino R, Bozzetto L, Ghirardini A. (2002). Detoxification of cytotoxic unsaturated aldehydes in keratinocytes is a GSH-dependent pathway: Inhibition by UVB and protective effect of histidine and cysteine-containing peptides. Preprints of the 22nd IFSCC, Edinburgh, 23-26 September 2002, vol.1 pp. 129-143.
35. Carini M., Aldini G., Beretta G., Arlandini E., Facino R.M. (2003). Acrolein-sequestering ability of endogenous dipeptides: Characterization of carnosine and homocarnosine/acrolein adducts by electrospray ionization tandem mass spectrometry. J Mass Spectrom 38: 996-1006.
36. Carini M., Aldini G., Maffei Facino R. (2004). Mass spectrometry for detection of 4-hydroxy-trans-2-nonenal (HNE) adducts with peptides and proteins. Mass Spectrom Rev 23: 281-305.
37. Chang K.C., Hsu K.L., Chou T.F., Lo H.M., Tseng Y.Z. (2004). Aminoguanidine prevents age-related deterioration in left ventricular-arterial coupling in Fisher 344 rats. Br J Pharmacol 142: 1099-1104.
38. Chen A.S., Taguchi T., Aoyama S. Sugiura M., Haruna M., Wang M.W., Miwa I. (2003). Antioxidant activity of a Schiff base of pyridoxal and aminoguanidine. Free Radic Biol Med 35: 1392-1403.
39. Chen A.S., Taguchi T., Sugiura M.,Wakasugi Y., Kamei A.,Wang M.W., Miwa I. (2004). Pyridoxal-aminoguanidine adduct is more effective than aminoguanidine in preventing neuropathy and cataract in diabetic rats. Horm Metab Res 36: 183-187.
40. Cohn J.A., Tsai L., Friguet B., Szweda L.I. (1996). Chemical characterization of a protein-4-hydroxy-2-nonenal cross-link: Immunochemical detection in mitochondria exposed to oxidative stress. Arch Biochem Biophys 328: 158-164.
41. Cotham W.E., Metz T.O., Ferguson P.L., Brock J.W., Hinton D.J., Thorpe S.R., Baynes J.W., Ames J.M. (2004). Proteomic analysis of arginine adducts on glyoxal-modified ribonuclease. Mol Cell Proteomics 3: 1145-1153.
42. Crush K.G. (1970). Carnosine and related substances in animal tissues. Comp Biochem Physiol 34: 3-30.
43. Culbertson S.M., Enright G.D., Ingold K.U. (2003a). Synthesis of a novel radical trapping and carbonyl group trapping anti-AGE agent: A pyridoxamine analogue for inhibiting advanced glycation (AGE) and lipoxidation (ALE) end products. Org Lett 5: 2659-2662.
44. Culbertson S.M., Vassilenko E.I., Morrison L.D., Ingold K.U. (2003b). Paradoxical impact of antioxidants on post-Amadori glycoxidation. J Biol Chem 278: 38384-38394.
45. Davies S.S., Amarnath V., Roberts L.J. 2nd. (2004). Isoketals: highly reactive gammaketoaldehydes formed from the H2-isoprostane pathway. Chem Phys Lipids 128: 85-99.
46. Degenhardt T.P., Alderson N.L., Arrington D.D., Beattie R.J., Basgen J.M., Steffes M.W., Thorpe S.R., Baynes J.W. (2002). Pyridoxamine inhibits early renal disease and dyslipidemia in the streptozotocin-diabetic rat. Kidney Int 61: 939-950.
47. Dei R., Takeda A., Niwa H., Li M., Nakagomi Y., Watanabe M., Inagaki T., Washimi Y., Yasuda Y., Horie K., Miyata T., Sobue G. (2002). Lipid peroxidation and advanced glycation end products in the brain in normal aging and in Alzheimer's disease. Acta Neuropathol 104: 113-122.
48. Doorn J.A., Petersen D.R. (2003). Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal. Chem Biol Interact 143-144: 93-100.
49. Eaton P., Li J.M., Hearse D.J., Shattock M.J. (1999). Formation of 4-hydroxy-2-nonenalmodified proteins in ischemic rat heart. Am J Physiol 276: H935-H943.
50. Esterbauer H., Zollner H., Schaur R.J. (1990). Aldehydes formed by lipid peroxidation: mechanisms of formation, occurrence, and determination. In: Vigo-Pelfrey C. (ed.), Membrane lipid oxidation, Vol. 1, CRC Press, Boca Raton, FL, pp. 239-268.
51. Esterbauer H., Schaur R.J., Zollner H. (1991). Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic Biol Med 11: 81-128.
52. Ferraris R.P., Diamond J., Kwan W.W. (1988). Dietary regulation of intestinal transport of the dipeptide carnosine. Am J Physiol 255: G143-G150.
53. Forbes J.M., Soulis T., Thallas V., Panagiotopoulos S., Long D.M., Vasan S., Wagle D., Jerums G., Cooper M.E. (2001). Renoprotective effects of a novel inhibitor of advanced glycation. Diabetologia 44: 108-114.
54. Forbes J.M., Yee L.T., Thallas V., Lassila M., Candido R., Jandeleit-Dahm K.A., Thomas M.C., Burns W.C., Deemer E.K., Thorpe S.M., Cooper M.E., Allen T.J. (2004). Advanced glycation end product interventions reduce diabetes-accelerated atherosclerosis. Diabetes 53: 1813-1823.
55. Fredrikson G.N., Hedblad B. Berglund G., Alm R., Ares M., Cercek B., Chyu K.Y., Shah P.K., Nilsson J. (2003a). Identification of immune responses against aldehyde-modified peptide sequences in apoB associated with cardiovascular disease. Arterioscler Thromb Vasc Biol 23: 872-878.
56. Fredrikson G.N., Söderberg I., Lindholm M., Dimayuga P., Chyu K.Y., Shah P.K., Nilsson J. (2003b). Inhibition of atherosclerosis in apoE-null mice by immunization with apoB-100 peptide sequences. Arterioscler Thromb Vasc Biol 23: 879-884.
57. Freedman B.I., Wuerth J.P., Cartwright K., Bain R.P., Dippe S., Hershon K., Mooradian A.D., Spinowitz B.S. (1999). Design and baseline characteristics for the Aminoguanidine Clinical Trial in Overt Type 2 Diabetic Nephropathy (ACTION II). Control Clin Trials 20: 493-510.
58. Fu M.X., Requena J.R., Jenkins A.J., Lyons T.J., Baynes J.W., Thorpe S.R. (1996). The advanced glycation end product, Nε-(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions. J Biol Chem 271: 9982-9986.
59. Furuhata A., Ishii T., Kumazawa S., Yamada T., Nakayama T., Uchida K. (2003). Nε-(3-methylpyridinium)lysine, a major antigenic adduct generated in acrolein-modified protein. J Biol Chem 278: 48658-48665.
60. Gallant S., Semyonova M., Yuneva M. (2000). Carnosine as a potential anti-senescence drug. Biochemistry (Mosc) 65: 866-868.
61. Ghilarducci D.P., Tjeerdema R.S. (1995). Fate and effects of acrolein. Rev Environ Contam Toxicol 144: 95-146.
62. Girones X., Guimera A., Cruz-Sanchez C.Z., Ortega A., Sasaki N., Makita Z., Lafuente J.V., Kalaria R., Cruz-Sanchez F.F. (2004). Nε-Carboxymethyllysine in brain aging, diabetes mellitus, and Alzheimer's disease. Free Radic Biol Med 36: 1241-1247.
63. Glomb M.A., Lang G. (2001). Isolation and characterization of glyoxal-arginine modifications. J Agric Food Chem 49: 1493-1501.
64. Haenen G.R., Vermeulen N.P., Tai Tin Tsoi J.N., Ragetli H.M., Timmerman H., Blast A. (1988). Activation of the microsomal glutathione-S-transferase and reduction of the glutathione dependent protection against lipid peroxidation by acrolein. Biochem Pharmacol 37: 1933-1938.
65. Hipkiss A.R., Michaelis J., Syrris P., Kumar S., Lam Y. (1994). Carnosine protects proteins against in vitro glycation and cross-linking. Biochem Soc Trans 22: 399S.
66. Hipkiss A.R., Preston J.E., Himswoth D.T., Worthington V.C., Abbot N.J. (1997). Protective effects of carnosine against malondialdehyde-induced toxicity towards cultured rat brain endothelial cells. Neurosci Lett 238: 135-138.
67. Hipkiss A.R. (1998). Carnosine, a protective, anti-aging peptide? Int J Biochem Cell Biol 30: 863-868.
68. Hipkiss A.R., Chana H. (1998). Carnosine protects proteins against methylglyoxal-mediated modifications. Biochem Biophys Res Commun 248: 28-32.
69. Hipkiss A.R., Brownson C. (2000). A possible new role for the anti-aging peptide carnosine. Cell Mol Life Sci 57: 747-753.
70. Hipkiss A.R., Brownson C., Carrier M.J. (2001). Carnosine, the anti-aging, anti-oxidant dipeptide, may react with protein carbonyl groups. Mech Aging Dev 122: 1431-1445.
71. Hipkiss A.R., Brownson C., Bertani M.F., Ruiz E., Ferro A. (2002). Reaction of carnosine with aged proteins: Another protective process? Ann NY Acad Sci 959: 285-294.
72. Hirsch J., Petrakova E., Feather M.S. (1992). The reaction of some dicarbonyl sugars with aminoguanidine. Carbohydr Res 232: 125-130.
73. Horinishi H., Grillo M., Margolis F.L. (1978). Purification and characterization of carnosine synthetase from mouse olfactory bulbs. J Neurochem 31: 909-919.
74. Hsu C.C., Yen H.F., Yin M.C., Tsai C.M., Hsieh C.H. (2004). Five cysteine-containing compounds delay diabetic deterioration in Balb/cA mice. J Nutr 134: 3245-3249.
75. Itakura K., Furuhata A., Shibata N., Kobayashi M., Uchida K. (2003). Maillard reactionlike lysine modification by a lipid peroxidation product: immunochemical detection of protein-bound 2-hydroxyheptanal in vivo. Biochem Biophys Res Commun 308: 452-457.
76. Januszewski A.S., Alderson N.L., Metz T.O., Thorpe S.R., Baynes J.W. (2003). Role of lipids in chemical modification of proteins and development of complications in diabetes. Biochem Soc Trans 31: 1413-1416.
77. Kaminskas L.M., Pyke S.M., Burcham P.C. (2004a). Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde. Org Biomol Chem 2: 2578-2584.
78. Kaminskas L.M., Pyke S.M., Burcham P.C. (2004b). Strong protein adduct trapping accompanies abolition of acrolein-mediated hepatotoxicity by hydralazine in mice. J Pharmacol Exp Ther 310: 1003-1010.
79. Kehrer J.P., Biswal S.S. (2000). The molecular effects of acrolein. Toxicol Sci 57: 6-15.
80. Kono H., Arteel G.E., Rusyn I., Sies H., Thurman R.G. (2001). Ebselen prevents early alcohol-induced liver injury in rats. Free Radic Biol Med 30: 403-411.
81. Lalich J.J., Paik W.C. (1974). Influence of hydralazine consumption on allylamine induced myocardial fibrosis and hypertrophy in rats. Exp Mol Pathol 21: 29-39.
82. Laurent A., Perdu-Durand E., Alary J., Debrauwer L., Cravedi J.P. (2000). Metabolism of 4-hydroxynonenal, a cytotoxic product of lipid peroxidation, in rat precision-cut liver slices. Toxicol Lett 114: 203-214.
83. Lederer M.O., Klaiber R.G. (1999). Cross-linking of proteins by Maillard processes: Characterization and detection of lysine-arginine cross-links derived from glyoxal and methylglyoxal. Bioorg Med Chem 7: 2499-2507.
84. Lee S.H., Blair I.A. (2000). Characterization of 4-oxo-2-nonenal as novel product of lipid peroxidation. Chem Res Toxicol 13: 698-702.
85. Lee S.H., Oe T., Blair I.A. (2001). Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins. Science 292: 2083-2086.
86. Levy R.S., Fisher M., Alter J.N. (1983). Penicillamine: Review and cutaneous manifestations. J Am Acad Dermatol 8: 548-558.
87. Li C.J., Nanji A.A., Siakotos A.N., Lin R.C. (1997). Acetaldehyde-modified and 4-hydroxynonenal-modified proteins in the livers of rats with alcoholic liver disease. Hepatology 26: 650-657.
88. Liu Q., Raina A.K., Smith M.A., Sayre L.M., Perry G. (2003a). Hydroxynonenal, toxic carbonyls, and Alzheimer disease. Mol Aspects Med 24: 305-313.
89. Liu Z., Minkler P.E., Sayre L.M. (2003b). Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal. Chem Res Toxicol 16: 901-911.
90. Liu Y., Xu G., Sayre L. (2003c). Carnosine inhibits (E)-4-hydroxy-2-nonenal-induced protein cross-linking: Structural characterization of carnosine-HNE adducts. Chem Res Toxicol 16: 1589-1597.
91. Loidl-Stahlhofen A., Spiteller G. (1994). Alpha-hydroxyaldehydes, products of lipid peroxidation. Biochim Biophys Acta 1211: 156-160.
92. Lovell M.A., Xie C., Markesbery W.R. (2001). Acrolein is increased in Alzheimer's disease brain and is toxic to primary hippocampal cultures. Neurobiol Aging 22: 187-194.
93. Lucas D.T., Szweda L.I. (1998). Cardiac reperfusion injury: Aging, lipid peroxidation, and mitochondrial dysfunction. Proc Natl Acad Sci USA 95: 510-514.
94. Mak S., Lehotay D.C., Yazdanpanah M., Azevedo E.R., Liu P.P., Newton G.E. (2000). Unsaturated aldehydes including 4-OH-nonenal are elevated in patients with congestive heart failure. J Card Fail 6: 108-114.
95. Mamputu J.C., Wiernsperger N., Renier G. (2003). Metformin inhibits monocyte adhesion to endothelial cells and foam cell formation. Brit J Diab Vasc Dis 3: 302-310.
96. Margolis F.L. (1974). Carnosine in the primary olfactory pathway. Science 184: 909-911.
97. McArdle F., Rhodes L.E., Parslew R.A., Close G.L., Jack C.I., Friedmann P.S., Jackson M.J. (2004). Effects of oral vitamin E and β-carotene supplementation on ultraviolet radiation-induced oxidative stress in human skin. Am J Clin Nutr 80: 1270-1275.
98. McGrath L.T., McGleenon B.M., Brennan S., McColl D., McILroy S., Passmore A.P. (2001). Increased oxidative stress in Alzheimer's disease as assessed with 4-hydroxynonenal but not malondialdehyde. Q J Med 94: 485-490.
99. Meade S.J., Miller A.G., Gerrard J.A. (2003). The role of dicarbonyl compounds in nonenzymatic crosslinking: a structure-activity study. Bioorg Med Chem 11: 853-862.
100. Metz T.O., Alderson N.L., Chachich M.E., Thorpe S.R., Baynes J.W. (2003a). Pyridoxamine traps intermediates in lipid peroxidation reactions in vivo: Evidence on the role of lipids in chemical modification of protein and development of diabetic complications. J Biol Chem 278: 42012-42019.
101. Metz T.O., Alderson N.L., Thorpe S.R., Baynes J.W. (2003b). Pyridoxamine, an inhibitor of advanced glycation and lipoxidation reactions: A novel therapy for treatment of diabetic complications. Arch Biochem Biophys 419: 41-49.
102. Miller A.G., Meade S.J., Gerrard J.A. (2003). New insights into protein crosslinking via the Maillard reaction: Structural requirements, the effect on enzyme function, and predicted efficacy of crosslinking inhibitors as anti-aging therapeutics. Bioorg Med Chem 11: 843-852.
103. Miyata T., Inagi R., Asahi K., Yamada Y., Horie K., Sakai H., Uchida K., Kurokawa K. (1998a). Generation of protein carbonyls by glycoxidation and lipoxidation reactions with autoxidation products of ascorbic acid and polyunsaturated fatty acids. FEBS Lett 437: 24-28.
104. Miyata T., Ueda Y., Yamada Y., Izuhara Y., Wada T., Jadoul M., Saito A., Kurokawa K., Van Ypersele de Strihou C. (1998b). Accumulation of carbonyls accelerates the formation of pentosidine, an advanced glycation end product: Carbonyl stress in uremia. J Am Soc Nephrol 9: 2349-2356.
105. Miyata T., van Ypersele de Strihou C., Kurokawa K, Baynes J.W. (1999a). Alterations in nonenzymatic biochemistry in uremia: Origin and significance of "carbonyl stress" in long-term uremic complications. Kidney Int 55: 389-399.
106. Miyata T., Ishikawa S., Asahi K., Inagi R., Suzuki D., Horie K., Tatsumi K., Kurokawa K. (1999b). 2-Isopropylidenehydrazono-4-oxo-thiazolidin-5-ylacetanilide (OPB-9195) treatment inhibits the development of intimal thickening after balloon injury of rat carotid artery: Role of glycoxidation and lipoxidation reactions in vascular tissue damage. FEBS Lett 445: 202-206.
107. Miyata T., Kurokawa K., Van Ypersele De Strihou C. (2000a). Advanced glycation and lipoxidation end products: Role of reactive carbonyl compounds generated during carbohydrate and lipid metabolism. J Am Soc Nephrol 11: 1744-1752.
108. Miyata T., Ueda Y., Asahi K., Izuhara Y., Inagi R., Saito A., van Ypersele De Strihou C., Kurokawa K. (2000b). Mechanism of the inhibitory effect of OPB-9195 [(+/-)-2-isopropylidenehydrazono-4-oxo-thiazolidin-5-yla cetanilide] on advanced glycation end product and advanced lipoxidation end product formation. J Am Soc Nephrol 11: 1719-1725.
109. Miyata T., Sugiyama S., Saito A., Kurokawa K. (2001a). Reactive carbonyl compounds related uremic toxicity ("carbonyl stress"). Kidney Int Suppl 78: S25-S31.
110. Miyata T., Saito A., Kurokawa K., Van Ypersele De Strihou C. (2001b). Advanced glycation and lipoxidation end products: Reactive carbonyl compounds-related uraemic toxicity. Nephrol Dial Transplant 16 (Suppl 4): 8-11.
111. Miyata T., van Ypersele de Strihou C. (2003). Angiotensin II receptor blockers and angiotensin converting enzyme inhibitors: Implication of radical scavenging and transition metal chelation in inhibition of advanced glycation end product formation. Arch Biochem Biophys 419: 50-54.
112. Miyoshi H., Taguchi T., Sugiura M., Takeuchi M., Yanagisawa K. Watanabe Y., Miwa I., Makita Z., Koike T. (2002). Aminoguanidine pyridoxal adduct is superior to aminoguanidine for preventing diabetic nephropathy in mice. Horm Metab Res 34: 371-377.
113. Mlakar A., Spiteller G. (1994). Reinvestigation of lipid peroxidation of linolenic acid. Biochim Biophys Acta 1214: 209-220.
114. Moreau R., Heath S.H., Doneanu C.E., Lindsay J.G., Hagen T.M. (2003). Age-related increase in 4-hydroxynonenal adduction to rat heart alpha-ketoglutarate dehydrogenase does not cause loss of its catalytic activity. Antioxid Redox Sign 5: 517-527.
115. Moreau R., Nguyen B.T., Doneanu C.E., Hagen T.M. (2005). Reversal by aminoguanidine of the age-related increase in glycoxidation and lipoxidation in the cardiovascular system of Fischer 344 rats. Biochem Pharmacol 69: 29-40.
116. Munch G., Taneli Y., Schraven E., Schindler U., Schinzel R., Palm D., Riederer P. (1994). The cognition-enhancing drug tenilsetam is an inhibitor of protein crosslinking by advanced glycosylation. J Neural Transm Park Dis Demen Sect 8: 193-208.
117. Munch G., Mayer S., Michaelis J., Hipkiss A.R., Riederer P., Muller R., Neumann A., Schinzel R., Cunningham A.M. (1997). Influence of advanced glycation end-products and AGE-inhibitors on nucleation-dependent polymerization of beta-amyloid peptide. Biochim Biophys Acta 1360: 17-29.
118. Nadkarni D.V., Sayre L.M. (1995). Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal. Chem Res Toxicol 8: 284-291.
119. Nair V., Vietti D.E., Cooper C.S. (1981). Degenerative chemistry of malondialdehyde: Structure, stereochemistry, and kinetics of formation of enaminals from reaction with amino acids. J Am Chem Soc 103: 3030-3096.
120. Nakamura S., Makita Z., Ishikawa S., Yasumura K., Fujii W., Yanagisawa K., Kawata T., Koike T. (1997). Progression of nephropathy in spontaneous diabetic rats is prevented by OPB-9195, a novel inhibitor of advanced glycation. Diabetes 45: 895-899.
121. Nakamura Y., Morimitsu Y., Uzu T., Ohigashi H., Murakami A., Naito Y., Nakagawa Y., Osawa T., Uchida K. (2000). A glutathione S-transferase inducer from papaya: Rapid screening, identification and structure-activity relationship of isothiocyanates. Cancer Lett 157: 193-200.
122. Nakamura S., Tachikawa T., Tobita K., Aoyama I., Takayama F., Enomoto A., Niwa T. (2003). An inhibitor of advanced glycation end product formation reduces Nε-(carboxymethyl) lysine accumulation in glomeruli of diabetic rats. Am J Kidney Dis 41(Suppl 1): S68-S71.
123. Neely M.D., Zimmerman L., Picklo M.J., Ou J.J., Morales C.R., Montine K.S., Amaranth V., Montine T.J. (2000). Congeners of N(alpha)-acetyl-L-cysteine but not aminoguanidine act as neuroprotectants from the lipid peroxidation product 4-hydroxy-2-nonenal. Free Radic Biol Med 29: 1028-1036.
124. Niemela O., Parkkial S., Pasanen M., Viitala K., Vilianueva J.A., Halsted C.H. (1999). Induction of cytochrome P450 enzymes and generation of protein-aldehyde adducts are associated with sex-dependent sensitivity to alcohol-induced liver disease in micropigs. Hepatology 30: 1011-1017.
125. Niemela O., Parkkila S., Worrall S., Emery P.W., Preedy V.R. (2003). Generation of aldehyde-derived protein modifications in ethanol-exposed heart. Alcohol Clin Exp Res 27: 1987-1992.
126. Noiri E., Yamada S., Nakao A., Tsuchiya M., Masaki I., Fujino K. (2002). Serum protein acrolein adducts: Utility in detecting oxidant stress in hemodialysis patients and reversal using a vitamin E-bonded hemodialyzer. Free Radic Biol Med 33: 1651-1656.
127. Oates J.A., Brown N.J. (2001). Antihypertensive agents and the drug therapy of hypertension. In: Hardman J.G. and Limbird L.E. (eds.), Goodman and Gilman's the Pharmacological Basis of Therapeutics, 10th ed., McGraw-Hill, New York, pp. 871-900.
128. Odani H., Shinzato T., Usami J., Matsumoto Y., Brinkmann Frye E., Baynes J.W., Maeda K. (1998). Imidazolium crosslinks derived from reaction of lysine with glyoxal and methylglyoxal are increased in serum proteins of uremic patients: evidence for increased oxidative stress in uremia. FEBS Lett 427: 381-385.
129. Odetti P., Pesce C., Traverso N., Menini S., Maineri E.P., Cosso L., Valentini S., Patriarca S., Cottalasso D., Marinari U.M., Pronzato M.A. (2003). Comparative trial of N-acetyl-cysteine, taurine, and oxerutin on skin and kidney damage in long-term experimental diabetes. Diabetes 52: 499-505.
130. Onorato J.M., Jenkins A.J., Thorpe S.R., Baynes J.W. (2000). Pyridoxamine, an inhibitor of advanced glycation reactions, also inhibits advanced lipoxidation reactions. Mechanism of action of pyridoxamine. J Biol Chem 275: 21177-21184.
131. Orioli M., Aldini G., Beretta G., Maffei Facino R., Carini M. (2005). LC-ESI-MS/MS determination of 4-hydroxy-trans-2-nonenal Michael adducts with cysteine and histidine-containing peptides as early markers of oxidative stress in excitable tissues J Chromatogi B 827: 109-118.
132. Palinski W., Miller E., Witztum J.L. (1995). Immunization of low density lipoprotein (LDL) receptor-deficient rabbits with homologous malondialdehyde-modified LDL reduces atherogenesis. Proc Natl Acad Sci USA 92: 821-825.
133. Paradis V., Kollinger M., Fabre M., Holstege A., Poynard T., Bedossa P. (1997a). In situ detection of lipid peroxidation by-products in chronic liver diseases. Hepatology 26: 135-142.
134. Paradis V., Mathurin P., Kollinger M., Imbert-Bismut F., Piton A., Opolon P., Holstege A., Poynard T., Bedossa P. (1997b). In situ detection of lipid peroxidation in chronic hepatitis C: correlation with pathological features. J Clin Pathol 50: 401-406.
135. Petersen D.R., Doorn J.A. (2004). Reactions of 4-hydroxynonenal with proteins and cellular targets. Free Radic Biol Med 37: 937-945.
136. Petroff O.A., Hyder F., Rothman D.L., Mattson R.H. (2001). Homocarnosine and seizure control in juvenile myoclonic epilepsy and complex partial seizures. Neurology 56: 709-715.
137. Picard S., Parthasarathy S., Fruebis J., Witztum J.L. (1992). Aminoguanidine inhibits oxidative modification of low density lipoprotein protein and the subsequent increase in uptake by macrophage scavenger receptors. Proc Natl Acad Sci USA 89: 6876-6880.
138. Picklo M.J., Montine T.J., Amarnath V., Neely M.D. (2002). Carbonyl toxicology and Alzheimer's disease. Toxicol Appl Pharmacol 184: 187-197.
139. Poli G., Schaur J. (2000). 4-Hydroxynonenal in the pathomechanisms of oxidative stress. IUBMB Life 50: 315-321.
140. Pryor A.W., Stanley P. (1975). A suggested mechanism for the production of malondialdehyde during the autooxidation of polyunsaturated fatty acids: Nonenzymatic production of prostaglandin endoperoxides during autoxidation. J Org Chem 40: 3615-3617.
141. Rahbar S., Natarajan R., Yerneni K., Scott S., Gonzales N., Nadler J.L. (2000). Evidence that pioglitazone, metformin and pentoxifylline are inhibitors of glycation. Clin Chim Acta 301: 65-77.
142. Rahbar S., Figarola J.L. (2003). Novel inhibitors of advanced glycation end products. Arch Biochem Biophys 419: 63-79.
143. Reinheckel T., Nedelev B., Prause J., Augustin W., Schulz H.U., Lippert H., Halangk W. (1998). Occurrence of oxidatively modified proteins: An early event in experimental acute pancreatitis. Free Radic Biol Med 24: 393-400.
144. Rindgen D., Nakajima M., Wehrli S., Xu K., Blair I.A. (1999). Covalent modifications to 2'-deoxyguanosine by 4-oxo-2-nonenal, a novel product of lipid peroxidation. Chem Res Toxicol 12: 1195-1204.
145. Ruggiero-Lopez D., Lecomte M., Moinet G., Patereau G., Lagarde M., Wiernsperger N. (1999). Reaction of metformin with dicarbonyl compounds: Possible implication in the inhibition of advanced glycation end product formation. Biochem Pharmacol 58: 1765-1773.
146. Sakata K., Kashiwagi K., Sharmin S., Ueda S., Irie Y., Murotani N., Igarashi K. (2003a). Increase in putrescine, amine oxidase, and acrolein in plasma of renal failure patients. Biochem Biophys Res Commun 305: 143-149.
147. Sakata K., Kashiwagi K., Sharmin S., Ueda S., Igarashi K. (2003b). Acrolein produced from polyamines as one of the uraemic toxins. Biochem Soc Trans 31: 371-374.
148. Sampey B.P., Korourian S., Ronis M.J., Badger T.M., Petersen D.R. (2003). Immunohistochemical characterization of hepatic malondialdehyde and 4-hydroxynonenal modified proteins during early stages of ethanol-induced liver injury. Alcohol Clin Exp Res 27: 1015-1022.
149. Sayre L.M., Arora P.K., Iyer R.S., Salomon R.G. (1993). Pyrrole formation from 4-hydroxynonenal and primary amines. Chem Res Toxicol 6: 19-22.
150. Sayre L.M., Zelasko D.A., Harris P.L.R., Perry G., Salomon R.G., Smith M.A. (1997). 4-hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease. J Neurochem 68: 2092-2097.
151. Schiopu A., Bengtsson J., Soderberg I., Janciauskiene S., Lindgren S., Ares M., Shah P.K., Carlsson R., Nilsson J., Fredrikson G.N. (2004). Recombinant human antibodies against aldehyde-modified apolipoprotein B-100 peptide sequences inhibit atherosclerosis. Circulation 110: 2047-2052.
152. Schneider C., Tallman K.A., Porter N.A., Brash A.R. (2001). Two distinct pathways of formation of 4-hydroxynonenal: Mechanisms of nonenzymatic transformation of the 9-and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals. J Biol Chem 276: 20831-20838.
153. Selley M.L. (1998). (E)-4-hydroxy-2-nonenal may be involved in the pathogenesis of Parkinson's disease. Free Radic Biol Med 25: 169-174.
154. Selwa L.M. (1999). N-Acetylcysteine therapy for Unverricht-Lundborg disease. Neurology 52: 426-427.
155. Shangari N., Bruce W.R., Poon R., O'Brien P.J. (2003). Toxicity of glyoxals-Role of oxidative stress, metabolic detoxification and thiamine deficiency. Biochem Soc Trans 31: 1390-1393.
156. Shangari N., O'Brien P.J. (2004). The cytotoxicity mechanism of glyoxal involves oxidative stress. Biochem Pharmacol 668: 1433-1442.
157. Shapiro H.K. (1998). Carbonyl-trapping therapeutic strategies. Am J Ther 5: 323-353.
158. Shibata N., Yamada S., Uchida K., Hirano A., Sakoda S., Fujimura H., Sasaki S., Iwata M., Toi S., Kawaguchi M., Yamamoto T., Kobayashi M. (2004). Accumulation of protein-bound 4-hydroxy-2-hexenal in spinal cords from patients with sporadic amyotrophic lateral sclerosis. Brain Res 1019: 170-177.
159. Shoda H., Miyata S., Liu B.F., Yamada H., Ohara T., Suzuki K., Oimomi M., Kasuga M. (1997). Inhibitory effects of tenilsetam on the Maillard reaction. Endocrinology 138: 1886-1892.
160. Siems W., Carluccio F., Grune T., Jakstadt M., Quast S., Hampl H., Sommerburg O. (2002). Elevated serum concentration of cardiotoxic lipid peroxidation products in chronic renal failure in relation to severity of renal anemia. Clin Nephrol 58 (Suppl 1): S20-S25.
161. Siems W., Grune T. (2003). Intracellular metabolism of 4-hydroxynonenal. Mol Aspects Med 24: 167-175.
162. Simpson E.P., Henry Y.K., Henkel J.S., Smith R.G., Appel S.H. (2004). Increased lipid peroxidation in sera of ALS patients. Neurobiol 62: 1758-1765.
163. Singh R., Burden A, Mori T., Bellin L. (2001). Advanced glycation end-products. Diabetologia 44: 129-146.
164. Slatter D.A., Murray M., Bailey A.J. (1998). Formation of a dihydropyridine derivative as a potential cross-link from malondialdehyde in physiological systems. FEBS Letts 421: 180-184.
165. Slatter D.A., Paul R.G., Murray M., Bailey A.J. (1999). Reactions of lipid-derived malondialdehyde with collagen. J Biol Chem 274: 19661-19669.
166. Slatter D.A., Bolton C.H., Bailey A.J. (2000). The importance of lipid-derived malondialdehyde in diabetes mellitus. Diabetologia 43: 550-557.
167. Slatter D.A., Avery N.C., Bailey A.J. (2004). Identification of a new cross-link and unique histidine adduct from bovine serum albumin incubated with malondialdehyde. J Biol Chem 279: 61-69.
168. Solin M.L., Ahola H., Haltia A., Ursini F., Montine T., Roveri A., Kerjaschki D., Holthofer H. (2001). Lipid peroxidation in human proteinuric disease. Kidney Int 59: 481-487.
169. Soulis T., Sastra S., Thallas V., Mortensen S.B., Wilken M., Clausen J.T., Bjerrum O.J., Petersen H., Lau J., Jerums G., Boel E., Cooper M.E. (1999). A novel inhibitor of advanced glycation end-product formation inhibits mesenteric vascular hypertrophy in experimental diabetes. Diabetologia 42: 472-479.
170. Sowell J., Frei B., Stevens J.F. (2004). Vitamin C conjugates of genotoxic lipid peroxidation products: Structural characterization and detection in human plasma. Proc Natl Acad Sci USA 101: 17964-17969.
171. Srivastava S., Dixit B.L., Cai J., Sharma S., Hurst H.E., Bhatnagar A., Srivastava S.K. (2000). Metabolism of lipid peroxidation product, 4-hydroxynonenal (HNE) in rat erythrocytes: Role of aldose reductase. Free Radic Biol Med 29: 642-651.
172. Stitt A., Gardiner T.A., Alderson N.L., Canning P., Frizzell N., Duffy N., Boyle C., Januszewski A.S., Chachich M. Baynes J.W., Thorpe S.R., Anderson N.L. (2002). The AGE inhibitor pyridoxamine inhibits development of retinopathy in experimental diabetes. Diabetes 51: 2826-2832.
173. Stuerenburg H.J. (2000). The roles of carnosine in aging of skeletal muscle and in neuromuscular diseases. Biochemistry (Mosc) 65: 862-865.
174. Stvolinsky S.L., Dobrota D. (2000). Anti-ischemic activity of carnosine. Biochemistry (Mosc) 65: 849-855.
175. Suzuki D., Miyata T. (1999). Carbonyl stress in the pathogenesis of diabetic nephropathy. Intern Med 38: 309-314.
176. Szweda L.I., Uchida K., Tsai L., Statdman E.R. (1993). Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. J Biol Chem 268: 3342-3347.
177. Taguchi T., Sugiura M., Hamada Y., Miwa I. (1998). In vivo formation of a Schiff base of aminoguanidine with pyridoxal phosphate. Biochem Pharmacol 55: 1667-1671.
178. Taguchi T., Sugiura M., Hamada Y., Miwa I. (1999). Inhibition of advanced protein glycation by a Schiff base between aminoguanidine and pyridoxal. Eur J Pharmacol 378: 283-289.
179. Tanaka Y., Iwamoto H., Onuma T., Kawamori R. (1997). Inhibitory effect of metformin on formation of advanced glycation end products. Curr Ther Res 58: 693-697.
180. Tanaka N., Tajima S., Ishibashi A., Uchida K., Shigematsu T. (2001). Immunohistochemical detection of lipid peroxidation products, protein-bound acrolein and 4-hydroxynonenal protein adducts, in actinic elastosis of photodamaged skin. Arch Dermatol Res 293: 363-367.
181. Terman A., Brunk U.T. (2004). Lipofuscin. Int J Biochem Cell Biol 36: 1400-1404.
182. Tessier F., Obrenovich M.,Monnier V.M. (1999). Structure andmechanism of formation of human lens fluorophore LM-1: Relationship to vesperlysine A and the advanced Maillard reaction in aging, diabetes, and cataractogenesis. J Biol Chem 274: 20796-20804.
183. Teufel M., Saudek V., Ledig J.P., Bernhardt A., Boularand S., Carreau A., Cairns N.J., Carter C., Cowley D.J., Duverger D., Ganzhorn A.J., Guenet C., Heintzelmann B., Laucher V., Sauvage C., Smirnova T. (2003). Sequence identification and characterization of human carnosinase and a closely related non-specific dipeptidase. J Biol Chem 278: 6521-6531.
184. Thies F., Garry J.M., Yaqoob P., Rerkasem K.,Williams J., Shearman C.P., Gallagher P.J., Calder P.C., Grimble R.F. (2003). Association of n-3 polyunsaturated fatty acids with stability of atherosclerotic plaques: A randomised controlled trial. Lancet 361: 477-485.
185. Thornalley P.J., Yurek-George A., Argirov O.K. (2000). Kinetics and mechanism of the reaction of aminoguanidine with the alpha-oxoaldehydes glyoxal, methylglyoxal, and 3-deoxyglucosone under physiological conditions. Biochem Pharmacol 60: 55-65.
186. Thornalley P.J. (2003). Use of aminoguanidine (Pimagedine) to prevent the formation of advanced glycation end products. Arch Biochem Biophys 419: 31-40.
187. Thorpe S.R., Baynes J.W. (2003). Maillard reaction products in tissue proteins: New products and new perspectives. Amino Acids 25: 275-281.
188. Toyokuni S., Yamada S., Kashima M., Ihara Y., Yamada Y., Tanaka T., Hiai H., Seino Y., Uchida K. (2000). Serum 4-hydroxy-2-nonenal-modified albumin is elevated in patients with type 2 diabetes mellitus. Antioxid Redox Sign 2: 681-685.
189. Traverso N., Menini S., Cosso L., Odetti P., Albano E., Pronzato M.A., Marinari U.M. (1998). Immunological evidence for increased oxidative stress in diabetic rats. Diabetologia 41: 265-270.
190. Tsakadze N.L., Srivastava S., Awe S.O., Adeagbo A.S., Bhatnagar A., D'Souza S.E. (2003). Acrolein-induced vasomotor responses of rat aorta. Am J Physiol Heart Circ Physiol 285: H727-H734.
191. Tsukahara H., Jiang M.Z.,Ohta N., Sato S., Tamura S., Hiraoka M.,Maeda M., Mayumi M. (2004). Oxidative stress in neonates: Evaluation using specific biomarkers. Life Sci 75: 933-938.
192. Uchida K., Stadtman E.R. (1992). Modification of histidine residues in proteins by reaction with 4-hydroxynonenal. Proc Natl Acad Sci USA 89: 4544-4548.
193. Uchida K., Itakura K., Kawakishi S., Hiai H., Toyokuni S., Stadtman E.R. (1995). Characterization of epitopes recognized by 4-hydroxy-2-nonenal specific antibodies. Arch Biochem Biophys 324: 241-248.
194. Uchida K.,Kanematsu M.,Morimitsu Y., Osawa T., Noguchi N.,Niki E. (1998a). Acrolein is a product of lipid peroxidation reaction. Formation of acrolein and its conjugate with lysine residues in oxidized low-density lipoproteins. J Biol Chem 273: 16058-16066.
195. Uchida K., Kanematsu M., Sakai K., Matsuda T., Hattorisd N., Mizuno Y., Suzuki D., Miyata T., Noguchi N., Niki E. (1998b). Protein-bound acrolein: Potential markers for oxidative stress. Proc Natl Acad Sci USA 95: 4882-4887.
196. Uchida K. (1999). Current status of acrolein as lipid peroxidation product. Trends Cardiovasc Mol 9: 109-113.
197. Uchida K. (2000). Role of reactive aldehyde in cardiovascular diseases. Free Radic Biol Med 28: 1685-1696.
198. Uchida K. (2003). 4-Hydroxy-2-nonenal: A product and mediator of oxidative stress. Prog Lipid Res 42: 318-343.
199. Uchida K., Kumagai T. (2003). 4-hydroxy-2-nonenal as a COX-2 inducer. Mol Aspects Med 24: 213-218.
200. Voziyan P.A., Metz T.O., Baynes J.W., Hudson B.G. (2002). A post-Amadori inhibitor pyridoxamine also inhibits chemical modification of proteins by scavenging carbonyl intermediates of carbohydrate and lipid degradation. J Biol Chem 277: 3397-3403.
201. Voziyan P.A., Khalifah R.G., Thibaudeau C., Yildiz A., Jacob J., Serianni A.S., Hudson B.G. (2003). Modification of proteins in vitro by physiological levels of glucose: Pyridoxamine inhibits conversion of Amadori intermediate to advanced glycation endproducts through binding of redox metal ions. J Biol Chem 278: 46616-46624.
202. Wada R.,Nishizawa Y.,Yagihashi N., Takeuchi M., Ishikawa Y.,Yasumura K.,Nakano M., Yagihashi S. (2001). Effects of OPB-9195, anti-glycation agent, on experimental diabetic neuropathy. Eur J Clin Invest 31: 513-520.
203. Waeg G., Dimsity G., Esterbauer H. (1996). Monoclonal antibodies for detection of 4-hydroxynonenal modified proteins. Free Radic Res 25: 149-159.
204. Wataya T., Nunomura A., Smith M.A., Siedlak S.L., Harris P.L., Shimohama S., Szweda L.I.,Kaminski M.A.,Avila J., Price D.L., Cleveland D.W., Sayre L.M., Perry G. (2002). High molecular weight neurofilament proteins are physiological substrates of adduction by the lipid peroxidation product hydroxynonenal. J Biol Chem 277: 4644-4648.
205. Wells-Knecht K.J., Brinkmann E., Baynes J.W. (1995). Characterization of an imidazolium salt formed from glyoxal and Nα-hippuryllysine: a model for Maillard reaction crosslinks in proteins. J Org Chem 60: 6246-6247.
206. Wilkinson-Berka J.L., Kelly D.J.,Koerner S.M., Jaworski K.,Davis B., Thallas V., Cooper M.E. (2002). ALT-946 and aminoguanidine, inhibitors of advanced glycation, improve severe nephropathy in the diabetic transgenic (mREN-2)27 rat. Diabetes 51: 3283-3289.
207. Wondrak G.T., Cervantes-Laurean D., Roberts M.J., Qasem J.G., Kim M., Jacobson E.L., Jacobson M.K. (2002). Identification of alpha-dicarbonyl scavengers for cellular protection against carbonyl stress. Biochem Pharmacol 63: 361-373.
208. Yamada S., Funada T., Shibata N., Kobayashi M., Kawai Y., Tatsuda E., Furuhata A., Uchida K. (2004). Protein-bound 4-hydroxy-2-hexenal as a marker of oxidized n-3 polyunsaturated fatty acids. J Lipid Res 45: 626-634.
209. Yoritaka A., Hattori N., Uchida K., Tanaka M., Stadtman E.R., Mizuno Y. (1996). Immunohistochemical detection of 4-hydroxynonenal protein adducts in Parkinson disease. Proc Natl Acad Sci USA 93: 2696-2701.
210. Zagorski M.G., Salomon R.G. (1982). Prostaglandin endoperoxide. Carboxylate catalysis and the effects of proton donors on the decomposition of 2,3-dioxabicyclo [2.2.1] heptane. J Am Chem Soc 104: 3498-3503.
211. Zarkovic N. (2003). 4-hydroxynonenal as a bioactive marker of pathophysiological processes. Mol Aspects Med 24: 281-291.
212. Zhang W.H., Liu J., Xu G., Yuan Q., Sayre L.M. (2003). Model studies on protein side chain modification by 4-oxo-2-nonenal. Chem Res Toxicol 16: 512-523.
213. Zhou S., Decker E.A. (1999). Ability of carnosine and other skeletal muscle components to quench unsaturated aldehydic lipid oxidation products. J Agric Food Chem 47: 51-55.