Compounds Blocking Methylglyoxal-induced Protein Modification and Brain Endothelial Injury

Archives of Medical Research

Volumn 45, Issue 8, 2014, Pages 753-764

  Tóth, Andrea E ^a,b   Tóth, András ^a,b   Walter, Fruzsina R ^a   Kiss, Lóránd ^a   Veszelka, Szilvia ^a   Ózsvári, Béla ^a,c   Puskás, László G ^a,c   Heimesaat, Markus M ^d   Dohgu, Shinya ^e   Kataoka, Yasufumi ^e   Rákhely, Gábor ^a,b   Deli, Mária A ^a  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

^c AVIDIN LTD   (Hungary)

^d CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

^e FUKUOKA UNIVERSITY   (Japan)

Author keywords

All trans retinoic acid; Aminoguanidine; Human brain endothelial cell; Methylglyoxal; Protein modification; U0126

Indexed keywords

1,4 DIAMINO 1,4 BIS(2 AMINOPHENYLTHIO) 2,3 DICYANOBUTADIENE; ALBUMIN; AMINOGUANIDINE; ANTIOXIDANT; ASCORBIC ACID; BETA ALANINE; BETA CATENIN; CARBONYL DERIVATIVE; CARNOSINE; CARRIER PROTEIN; FLUORESCEIN ISOTHIOCYANATE DEXTRAN; GAMMA TOCOPHEROL; GW 3333; INDAPAMIDE; MESSENGER RNA; METHYLGLYOXAL; MITOGEN ACTIVATED PROTEIN KINASE; NEUROPROTECTIVE AGENT; PIRACETAM; REACTIVE OXYGEN METABOLITE; RETINOIC ACID; TIGHT JUNCTION PROTEIN; UNCLASSIFIED DRUG; 1,3 BUTADIENE DERIVATIVE; ENZYME INHIBITOR; GUANIDINE DERIVATIVE; NITRILE;

ARTICLE; BLOOD BRAIN BARRIER; BLOOD VESSEL INJURY; BRAIN CAPILLARY ENDOTHELIAL CELL; BRAIN INJURY; CELL FREE SYSTEM; CELL VIABILITY ASSAY; CONTROLLED STUDY; ENDOTHELIUM CELL; ENZYME INHIBITION; GENE EXPRESSION; HUMAN; HUMAN CELL; IMMUNOHISTOCHEMISTRY; IMPEDANCE; INFLAMMATION; MONOLAYER CULTURE; NEUROPROTECTION; PROTEIN MODIFICATION; SIGNAL TRANSDUCTION; ALZHEIMER DISEASE; ANTAGONISTS AND INHIBITORS; CELL LINE; CELL SURVIVAL; CYTOLOGY; DRUG EFFECTS; GENETICS; METABOLISM; PATHOLOGY; VASCULAR ENDOTHELIUM;

ALZHEIMER DISEASE; ANTIOXIDANTS; BETA CATENIN; BLOOD-BRAIN BARRIER; BUTADIENES; CELL LINE; CELL SURVIVAL; ENDOTHELIAL CELLS; ENDOTHELIUM, VASCULAR; ENZYME INHIBITORS; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; GUANIDINES; HUMANS; MAP KINASE SIGNALING SYSTEM; NITRILES; PYRUVALDEHYDE; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION; TIGHT JUNCTION PROTEINS; TRETINOIN;

EID: 84924754843     PISSN: 01884409     EISSN: 18735487     Source Type: Journal    
DOI: 10.1016/j.arcmed.2014.10.009     Document Type: Article

References (73)

1. Phillips S.A., Thornalley P.J. The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal. Eur J Biochem 1993, 212:101-105.
2. Rabbani N., Thornally P.J. Methylglyoxal, glyoxalase 1 and the dicarbonyl proteome. Amino Acids 2012, 42:1133-1142.
3. Ramasamy R., Yan S.F., Schmidt A.M. Methylglyoxal comes of AGE. Cell 2006, 124:258-260.
4. Liu J., Wang R., Desai K., et al. Upregulation of aldolase B and overproduction of methylglyoxal in vascular tissues from rats with metabolic syndrome. Cardiovasc Res 2011, 92:494-503.
5. Lapolla A., Flamini R., Dalla Vedova A., et al. Glyoxal and methylglyoxal levels in diabetic patients: quantitative determination by a new GC/MS method. Clin Chem Lab Med 2003, 41:1166-1173.
6. Vander Jagt D.L., Hunsaker L.A. Methylglyoxal metabolism and diabetic complications: roles of aldose reductase, glyoxalase-I, betaine aldehyde dehydrogenase and 2-oxoaldehyde dehydrogenase. Chem Biol Interact 2003, 143:341-351.
7. Kalapos M.P. Where does plasma methylglyoxal originate from?. Diabetes Res Clin Pract 2013, 99:260-271.
8. Uchida K. Role of reactive aldehyde in cardiovascular diseases. Free Radic Biol Med 2000, 28:1685-1696.
9. Kuhla B., Luth H.J., Haferburg D., et al. Methylglyoxal, glyoxal, and their detoxification in Alzheimer's disease. Ann NY Acad Sci 2005, 1043:211-216.
10. Dukic-Stefanovic S., Schinzel R., Riederer P., et al. AGES in brain ageing: AGE-inhibitors as neuroprotective and anti-dementia drugs?. Biogerontology 2001, 2:19-34.
11. Münch G., Westcott B., Menini T., et al. Advanced glycation endproducts and their pathogenic roles in neurological disorders. Amino Acids 2012, 42:1221-1236.
12. Beeri M.S., Moshier E., Schmeidler J., et al. Serum concentration of an inflammatory glycotoxin, methylglyoxal, is associated with increased cognitive decline in elderly individuals. Mech Ageing Dev 2011, 132:583-587.
13. Zlokovic B.V. The blood-brain barrier in health and chronic neurodegenerative disorders. Neuron 2008, 57:178-201.
14. Okouchi M., Okayama N., Aw T.Y. Preservation of cellular glutathione status and mitochondrial membrane potential by N-acetylcysteine and insulin sensitizers prevent carbonyl stress-induced human brain endothelial cell apoptosis. Curr Neurovasc Res 2009, 6:267-278.
15. Li W., Maloney R.E., Circu M.L., et al. Acute carbonyl stress induces occludin glycation and brain microvascular endothelial barrier dysfunction: role for glutathione-dependent metabolism of methylglyoxal. Free Radic Biol Med 2013, 54:51-61.
16. Li W., Xu H., Hu Y., et al. Edaravone protected human brain microvascular endothelial cells from methylglyoxal-induced injury by inhibiting AGEs/RAGE/oxidative stress. PLoS One 2013, 8:e76025.
17. Li W., Liu J., He P., et al. Hydroxysafflor yellow A protects methylglyoxal-induced injury in the cultured human brain microvascular endothelial cells. Neurosci Lett 2013, 549:146-150.
18. Tóth A.E., Walter F.R., Bocsik A., et al. Edaravone protects against methylglyoxal-induced barrier damage in human brain endothelial cells. PLoS One 2014, 9:e100152.
19. Abbott N.J., Patabendige A.A., Dolman D.E., et al. Structure and function of the blood-brain barrier. Neurobiol Dis 2010, 37:13-25.
20. Lee C., Yim M.B., Chock P.B., et al. Oxidation-reduction properties of methylglyoxal-modified protein in relation to free radical generation. J Biol Chem 1998, 273:25272-25278.
21. Rabbani N., Thornalley P.J. Dicarbonyls linked to damage in the powerhouse: glycation of mitochondrial proteins and oxidative stress. Biochem Soc Trans 2008, 36:1045-1050.
22. Desai K., Wu L. Methylglyoxal and advanced glycated end products: new therapeutical horisons?. Recent Pat Cardiovasc Drug Discov 2007, 2:89-99.
23. Thornalley P.J. Use of aminoguanidine (Pimagedine) to prevent the formation of advanced glycation endproducts. Arch Biochem Biophys 2003, 419:31-40.
24. Brown G.M., Reynolds J.J. Biogenesis of the water-soluble vitamins. Annu Rev Biochem 1963, 32:419-462.
25. Reddy V.P., Garrett M.R., Perry G., Smith M.A. Carnosine: a versatile antioxidant and antiglycating agent. Sci Aging Knowledge Environ 2005, 18:pe12.
26. Tilton R.G., Chang K., Hasan K.S., et al. Prevention of diabetic vascular dysfunction by guanidines. Inhibition of nitric oxide synthase versus advanced glycation end-product formation. Diabetes 1993, 42:221-232.
27. Key K.M., Morgan B.G. The determination of the vitamin C value of ascorbic acid. Biochem J 1933, 27:1030-1035.
28. Aruoma O.I., Laughton M.J., Halliwell B. Carnosine, homocarnosine and anserine: could they act as antioxidants invivo?. Biochem J 1989, 15:863-869.
29. Doggrell S.A. TACE inhibition: a new approach to treating inflammation. Expert Opin Investig Drugs 2002, 11:1003-1006.
30. Campbell D.B., Brackman F. Cardiovascular protective properties of indapamide. Am J Cardiol 1990, 65:11H-27H.
31. Winblad B. Piracetam: a review of pharmacological properties and clinical uses. CNS Drug Rev 2005, 11:169-182.
32. Durston A.J., Timmermans J.P., Hage W.J., et al. Retinoic acid causes an anteroposterior transformation in the developing central nervous system. Nature 1989, 13:140-144.
33. Galli F., Azzi A. Present trends in vitamin E research. Biofactors 2010, 36:33-42.
34. Favata M.F., Horiuchi K.Y., Manos E.J., et al. Identification of a novel inhibitor of mitogen-activated protein kinase kinase. J Biol Chem 1998, 17:18623-18632.
35. Hernández R.H., Armas-Hernández M.J., Velasco M., et al. Calcium antagonists and atherosclerosis protection in hypertension. Am J Ther 2003, 10:409-414.
36. Li W., Ota K., Nakamura J., et al. Antiglycation effect of gliclazide on invitro AGE formation from glucose and methylglyoxal. Exp Biol Med (Maywood) 2008, 233:176-179.
37. Kiho T., Kato M., Usui S., et al. Effect of buformin and metformin on formation of advanced glycation end products by methylglyoxal. Clin Chim Acta 2005, 358:139-145.
38. Weksler B.B., Subileau E.A., Perrière N., et al. Blood-brain barrier-specific properties of a human adult brain endothelial cell line. FASEB J 2005, 19:1872-1874.
39. Paolinelli R.C.M., Ferrarini L., Devraj K., et al. Wnt activation of immortalized brain endothelial cells as a tool for generating a standardized model of the blood brain barrier invitro. PLoS One 2013, 8:e70233.
40. Edelstein D., Brownlee M. Mechanistic studies of advanced glycosylation end product inhibition by aminoguanidine. Diabetes 1992, 41:26-29.
41. Ózsvári B., Puskás L.G., Nagy L.I., et al. A cell-microelectronic sensing technique for the screening of cytoprotective compounds. Int J Mol Med 2010, 25:525-530.
42. Hellinger E., Veszelka S., Tóth A.E., et al. Comparison of brain capillary endothelial cell-based and epithelial (MDCK-MDR1, Caco-2, and VB-Caco-2) cell-based surrogate blood-brain barrier penetration models. Eur J Pharmacol Biopharmacol 2012, 82:340-351.
43. Livak K.J., Schmittgen T.D. Analysis of relative gene expression data using real-time quantitative PCR and the 2(-Delta Delta C(T)) Method. Methods 2001, 25:402-408.
44. Sena C.M., Matafome P., Crisostomo J., et al. Methylglyoxal promotes oxidative stress and endothelial dysfunction. Pharmacol Res 2012, 65:497-506.
45. Weksler B., Romero I.A., Couraud P.O. The hCMEC/D3 cell line as a model of the human blood brain barrier. Fluids Barriers CNS 2013, 10:16.
46. Ohtsuki S., Yamaguchi H., Katsukura Y., et al. mRNA expression levels of tight junction protein genes in mouse brain capillary endothelial cells highly purified by magnetic cell sorting. J Neurochem 2008, 104:147-154.
47. Krause G., Winkler L., Mueller S.L., et al. Structure and function of claudins. Biochim Biophys Acta 2008, 1778:631-645.
48. Redzic Z. Molecular biology of the blood-brain and the blood-cerebrospinal fluid barriers: similarities and differences. Fluids Barriers CNS 2011, 8:3.
49. Erickson M.A., Banks W.A. Blood-brain barrier dysfunction as a cause and consequence of Alzheimer's disease. J Cereb Blood Flow Metab 2013, 33:1500-1513.
50. Uchida Y., Ohtsuki S., Katsukura Y., et al. Quantitative targeted absolute proteomics of human blood-brain barrier transporters and receptors. J Neurochem 2011, 117:333-345.
51. Pahnke J., Fröhlich C., Krohn M., et al. Impaired mitochondrial energy production and ABC transporter function-A crucial interconnection in dementing proteopathies of the brain. Mech Ageing Dev 2013, 134:506-515.
52. Gosselet F., Saint-Pol J., Candela P., et al. Amyloid-β peptides, Alzheimer's disease and the blood-brain barrier. Curr Alzheimer Res 2013, 10:1015-1033.
53. Dauchy S., Miller F., Couraud P.O., et al. Expression and transcriptional regulation of ABC transporters and cytochromes P450 in hCMEC/D3 human cerebral microvascular endothelial cells. Biochem Pharmacol 2009, 77:897-909.
54. Decleves X., Jacob A., Yousif S., et al. Interplay of drug metabolizing CYP450 enzymes and ABC transporters in the blood-brain barrier. Curr Drug Metab 2011, 12:732-741.
55. Bauer B., Hartz A.M., Lucking J.R., et al. Coordinated nuclear receptor regulation of the efflux transporter, Mrp2, and the phase-II metabolizing enzyme, GSTpi, at the blood-brain barrier. J Cereb Blood Flow Metab 2008, 28:1222-1234.
56. Ghosh C., Puvenna V., Gonzalez-Martinez J., et al. Blood-brain barrier P450 enzymes and multidrug transporters in drug resistance: a synergistic role in neurological diseases. Curr Drug Metab 2011, 12:742-749.
57. Boušová I., Průchová Z., Trnková L., et al. Comparison of glycation of glutathione S-transferase by methylglyoxal, glucose or fructose. Mol Cell Biochem 2011, 357:323-330.
58. Sasaki N.A., Garcia-Alvarez M.C., Wang Q., et al. N-Terminal 2,3-diaminopropionic acid (Dap) peptides as efficient methylglyoxal scavengers to inhibit advanced glycation endproduct (AGE) formation. Bioorg Med Chem 2009, 17:2310-2320.
59. Vastag M., Skopál J., Voko Z., et al. Expression of membrane-bound and soluble cell adhesion molecules by human brain microvessel endothelial cells. Microvasc Res 1999, 57:52-60.
60. Schoeff L. Vitamin A. Am J Med Technol 1983, 49:447-452.
61. Mizee M.R., Nijland P.G., van der Pol S.M., et al. Astrocyte-derived retinoic acid: a novel regulator of blood-brain barrier function in multiple sclerosis. Acta Neuropathol 2014, 128:691-703.
62. Kalapos M.P. The tandem of free radicals and methylglyoxal. Chem Biol Interact 2008, 171:251-271.
63. Lee B.H., Hsu W.H., Huang T., et al. Effects of monascin on anti-inflammation mediated by Nrf2 activation in advanced glycation end product-treated THP-1 monocytes and methylglyoxal-treated wistar rats. J Agric Food Chem 2013, 61:1288-1298.
64. Liebner S., Plate K.H. Differentiation of the brain vasculature: the answer came blowing by the Wnt. J Angiogenesis Res 2010, 2:1.
65. Beard R.S., Reynolds J.J., Bearden S.E. Hyperhomocysteinemia increases permeability of the blood-brain barrier by NMDA receptor-dependent regulation of adherens and tight junctions. Blood 2011, 118:2007-2014.
66. Cardoso F.L., Kittel A., Veszelka S., et al. Exposure to lipopolysaccharide and/or unconjugated bilirubin impairs the integrity and function of brain microvascular endothelial cells. PLoS One 2012, 7:e35919.
67. Roe K., Kumar M., Lum S., et al. West Nile virus-induced disruption of the blood-brain barrier in mice is characterized by the degradation of the junctional complex proteins and increase in multiple matrix metalloproteinases. J Gen Virol 2012, 93:1193-1203.
68. Kürti L., Veszelka S., Bocsik A., et al. Retinoic acid and hydrocortisone strengthen the barrier function of human RPMI 2650 cells, a model for nasal epithelial permeability. Cytotechnology 2013, 65:395-406.
69. Lippmann E.S., Al-Ahmad A., Azarin S.M., et al. A retinoic acid-enhanced, multicellular human blood-brain barrier model derived from stem cell sources. Sci Rep 2014, 4:4160.
70. Kitamura M., Ishikawa Y., Moreno-Manzano V., et al. Intervention by retinoic acid in oxidative stress-induced apoptosis. Nephrol Dial Transplant 2002, 9:84-87.
71. Akhand A.A., Hossain K., Mitsui H., et al. Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells. Free Radic Biol Med 2001, 31:20-30.
72. Fischer S., Wiesnet M., Renz D., et al. H2O2 induces paracellular permeability of porcine brain-derived microvascular endothelial cells by activation of the p44/42 MAP kinase pathway. Eur J Cell Biol 2005, 84:687-697.
73. András I.E., Toborek M. HIV-1 stimulates nuclear entry of amyloid beta via dynamin dependent EEA1 and TGF-β/Smad signaling. Exp Cell Res 2014, 323:66-76.