Acridine derivatives inhibit lysozyme aggregation

European Biophysics Journal

Volumn 37, Issue 7, 2008, Pages 1261-1270

  Gazova, Zuzana ^a   Bellova, Andrea ^b   Daxnerova, Zuzana ^b   Imrich, Jan ^b   Kristian, Pavol ^b   Tomascikova, Jana ^b   Bagelova, Jaroslava ^a   Fedunova, Diana ^a   Antalik, Marian ^a,b  

^a INSTITUTE OF EXPERIMENTAL PHYSICS   (Slovakia)

^b P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

Acridine; Amyloid; Lysozyme; Protein aggregation

Indexed keywords

ACRIDINE DERIVATIVE; AMYLOID; LYSOZYME; THIOFLAVINE;

CONFERENCE PAPER; FLUORESCENCE ANALYSIS; IC 50; MOLECULAR INTERACTION; PROTEIN AGGREGATION; TRANSMISSION ELECTRON MICROSCOPY;

ACRIDINES; AMYLOID; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MOLECULAR WEIGHT; MURAMIDASE; PROTEIN BINDING; SMALL MOLECULE LIBRARIES; THIAZOLES; TIME FACTORS;

EID: 50449095894     PISSN: 01757571     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00249-008-0313-0     Document Type: Conference Paper

References (63)

1. S Baglioni F Casamenti M Bucciantini L Luheshi N Taddei F Chiti CM Dobson M Stefani 2006 Prefibrillar amyloid aggregates could be generic toxins in higher organisms J Neurosci 26 31 8160 8167
2. MC Bennett 2005 The role of α-synuclein in neurodegenerative diseases Pharmacol Ther 105 311 331
3. D Booth M Sunde V Bellotti CV Robinson WL Hutchinson PE Fraser PN Hawkins CM Dobson SE Radford CCF Blake MB Pepys 1997 Instability, unfolding and aggregation of human lysozyme variants underlying amyloid fibrillogenesis Nature 385 787 793
4. M Bucciantini E Giannoni F Chiti F Baroni L Formigli J Zurdo N Taddei G Ramponi CM Dobson M Stefani 2002 Inherent toxicity of aggregates implies a common mechanism for protein misfoling disease Nature 416 507 511
5. C Canale S Torrassa P Rispoli A Pelini R Rolandi A Bucciantini M Stefani A Gliozzi 2006 Natively folded HypF-N and its early amyloid aggregates interact with phospholipid monolayers and destabilize supported lipid bilayers Biophys J 91 4675 4588
6. AK Chamberlain CE MacPhee J Zurdo LA Morozova-Roche HA Hill CM Dobson JJ Davis 2000 Ultrastructural organization of amyloid fibrils by atomic force microscopy Biophys J 79 3282 3293
7. D Canet M Sunde AM Last A Miranker A Spencer CV Robinson CM Dobson 1999 Mechanistic studies of the folding of human lysozyme and the origin of amyloidogenic behaviour in its disease related variants Biochemistry 38 6419 6427
8. A Cao D Hu L Lai 2004 Formation of amyloid fibrils from fully reduced hen egg white lysozyme Protein Sci 13 319 324
9. WS Caughey LD Raymond M Horiuchi B Caughey 1998 Inhibition of protease-resistant prion protein formation by porphyrins and phthalocyanines Proc Natl Acad Sci USA 95 21 12117 12122
10. F Chiti P Webster N Taddei A Clark M Stefani G Ramponi CM Dobson 1999 Designing conditions for in vitro formation of amyloid protofilaments and fibrils Proc Natl Acad Sci USA 96 3590 3594
11. KA Conway SJ Lee JC Rochet TT Ding RE Williamson PT Lansbury Jr 2000 Acceleration of oligomerization, not fibrilization, is a shared property of both α-synuclein mutations linked to early-onset Parkinson's disease: implications for pathogenesis and therapy Proc Natl Acad Sci USA 97 571 576
12. JH Cooper 1974 Selective staining as a function of amyloid composition and structure: histochemical analysis of the alkaline Congo Red, standardized toluidine blue and iodine methods Lab Invest 31 232 238
13. FG DeFelice JC Houzel J Garcia-Abreu PRF Louzada RC Afonso NL Meirelles R Lent MV Neto ST Ferreira 2001 Inhibition of Alzheimer's disease β-amyloid aggregation, neurotoxicity, and in vivo deposition by nitrophenols: implications for Alzheimer's theraphy FASEB J 15 1297 1299
14. FG DeFelice PT Velasco MP Lambert K Viola SJ Fernandez ST Ferreira WL Klein 2007 Abeta oligomers induce neuronal oxidative stress through an N-methyl-D-aspartate receptor-dependent mechanism that is blocked by the Alzheimer drug memantine J Biol Chem 282 11590 11601
15. A Demuro E Mina R Kayed SC Milton I Parker CG Glabe 2005 Calcium dysregulation and membrane disruption as a ubiquitous neurotoxic mechanism of soluble amyloid oligomers J Biol Chem 280 17294 17300
16. CM Dobson 1999 Protein misfolding, evolution and disease Trends Biochem Sci 24 329 332
17. CM Dobson 2001 The structural basis of protein folding and its links with human disease Philos Trans Rsoc Lond B Biol Sci 356 133 145
18. M Fandrich MA Fletcher CM Dobson 2001 Amyloid fibrils from muscle myoglobin Nature 410 165 166
19. ST Ferreira MN Vieira FG De Felice 2007 Soluble protein oligomers as emerging toxins in Alzheimer's and other amyloid diseases IUBMB Life 59 332 345
20. J Funahashi K Takano K Ogasahara Y Yamagata K Yutani 1996 The structure, stability, and folding process of amyloidogenic mutant human lysozyme J Biochem 120 1216 1223
21. M Goedert MG Spillantini 2006 A century of Alzheimer's disease Science 314 777 781
22. GK Gouras CG Almeida RH Takahashi 2005 Intraneuronal Abeta accumulation and origin of plaques in Alzheimer's disease Neurobiol Aging 26 1235 1244
23. JII Guijarro M Sunde JA Jones ID Campbell CM Dobson 1998 Amyloid fibril formation by an SH3 domain Proc Natl Acad Sci USA 95 4224 4228
24. C Haass DJ Selkoe 2007 Soluble oligomers in neurodegeneration: lessons from the Alzheimer's amyloid beta-peptide Nat Rev Mol Cell Biol 8 101 112
25. X Hou HC Parkington HA Coleman A Mechler LL Martin MI Aguilar DH Small 2000 Transthyretin oligomers induce calcium influx via voltage-gated calcium channels J Mol Biol 300 5 1033 1039
26. I Khlistunova J Biernat YP Wang M Pickhardt M von Bergen Z Gazova EM Mandelkow E Mandelkow 2006 Inducible expression of Tau repeat domain in cell models of tauopathy: aggregation is toxic to cells but can be reversed by inhibitor drugs J Biol Chem 281 1205 1214
27. WE Klunk JW Pettigrew DJ Abraham 1989 Quantitative evaluation of congo red binding to amyloid-like proteins with a beta-pleated sheet conformation J Histochem. Cytochem 37 8 1273 1281
28. EH Koo PT Lansbury JW Kelly 1999 Amyloid diseases: abnormal protein aggregation in neurodegeneration Proc Natl Acad Sci USA 96 9989 9990
29. C Korth BCH May FE Cohen SB Prusiner 2001 Acridine and phenothiazine derivatives as pharmacotherapeutics for prion disease PNAS 98 9836 9841
30. P Kristian S Hamulakova J Bernat J Imrich G Voss T Busova 1998 Synthesis of acetylcholinesterase inhibitors on the basis of 9-isothiocyanato-1,2,3,4- tetrahydroacridine: 2-[(1,2,3,4-tetrahydroacridin-9-yl)imino]-3-substituted 1,3-thiazolidin-4-ones Heterocycles 49 197 204
31. MP Lambert AK Barlow BA Chromy C Edwards R Freed M Liosatos TE Morgan I Rozovsky B Tromer KL Violc P Wals C Zhang CE GA Finch Krafft WLn Klein 1998 Diffusible, nonfibrillar ligands derived from Abeta1-42 are potent central nervous system neurotoxins Proc Natl Acad Sci USA 95 6448 6453
32. PT Lansbury Jr 1999 Evolution of amyloid: what normal protein folding may tell us about fibrillogenesis and disease Proc Natl Acad Sci USA 96 3342 3344
33. VM Lee M Goedert JQ Trojanowski 2001 Neurodegenerative tauopathies Annu Rev Neurosci 24 1121 1159
34. H LeVine 1993 Thioflavine T interaction with synthetic Alzheimeŕs disease beta-amyloid peptides: detection of amyloid aggregation in solution Protein Sci 2 404 410
35. LF Lue YM Kuo AE Roher L Brachova Y Shen L Sue T Beach JH Kurth RE Rydel J Rogers 1999 Soluble amyloid beta peptide concentration as a predictor of synaptic change in Alzheimeŕs disease Am J Pathol 155 3 853 862
36. BCH May AT Fafarman SB Hong M Rogers LW Deady SB Prusiner FE Cohen 2003 Potent inhibition of scrapie prion replication in cultured cells by bis-acridines PNAS 100 3416 3421
37. G Merlini V Bellotti 2003 Molecular mechanisms of amyloidosis N Engl J Med 349 583 596
38. PI Moreira K Honda Q Liu MS Santos CR Oliviera G Aliev A Nunomura X Zhu MA Smith G Perry 2005 Oxidative stress: the old enemy in Alzheimeŕs disease pathophysiology Curr Alzheimer Res 2 403 408
39. LA Morozova-Roche J Zurdo A Spencer W Noppe V Receveur DB Archer M Joniau CM Dobson 2000 Amyloid fibril formation an seeding by wild-type human lysozyme and its disease-related mutational variants J Struct Biol 130 339 351
40. JT Nguyen H Inouye MA Baldwin RJ FE Fletterick Cohen SB Prusiner DA Kirschner 1995 X-ray diffraction of scrapie prion rods and PrP peptides J Nol Biol 252 412 422
41. K Ono T Hamaguchi H Naiki M Yamada 2006 Anti-amyloidogenic effect of antioxidants: implication for the prevention and therapeutics of Alzheimer's disease Biochim Biophys Acta 1762 575 586
42. MB Pepys PN Hawkins DR Booth DM Vigushin GA Tennent AK Soutar N Totty O Nguyen CCF Blake CJ Terry TG Feest AM Zalin JJ Hsuan 1993 Human lysozyme gene mutations cause hereditary systemic amyloidosis Nature 362 553 557
43. M Pickhardt Z Gazova M von Bergen I Khlistunova Y Wang A Hascher EM Mandelkow J Biernat E Mandelkow 2005 Anthraquinones inhibit tau aggregation and dissolve Alzheimer's paired helical filaments in vitro and in cells J Biol Chem 280 3628 3635
44. M Pickhardt J Biernat I Khlistunova Y-P Wang Z Gazova E-M Mandelkow E Mandelkow 2007 N-Phenylamine derivatives as aggregation inhibitors in cell models of tauopathy Curr Alzheimer Res 4 397 402
45. SA Priola A Raines B Caughey 2000 Porphyrin and phthalocyanine antiscrapie compounds Science 287 5457 1503 1506
46. P Raghu GB Reddy B Sivakumar 2002 Inhibition of transthyretin amyloid fibril formation by 2,4-dinitrophenol through tetramer stabilization Arch Biochem Biophys 400 43 47
47. N Reixach S Deechongkit X Jiang JW Kelly JN Buxbaum 2004 Tissue damage in the amyloidosis: transthyretin monomers and nonnative oligomers are the major cytotoxic species in tissue culture Proc Natl Acad Sci USA 101 2817 2822
48. ED Roberson K Scearce-Levie JJ Palop F Yan IH Cheng T Wu H Gerstein GQ Yu L Mucke 2007 Reducing endogenous tau ameliorates amyloid beta-induced deficits in an Alzheimer's disease mouse model Science 316 5825 750 754
49. LC Serpell M Sunde MD Benson GA Tennent MB Pepys PE Fraser 2000 The protofilament substructure of amyloid fibrils J Mol Biol 300 5 1033 1039
50. Sipse JD (2005) Amyloid Proteins. Wiley-VCH Verlag GmbH and Co. KgaA, Weinheim Germany
51. M Stefani CM Dobson 2003 Protein aggregation and aggregate toxicity: new insights into protein folding, misfolding diseases and biological evolution J Mol Med 81 678 699
52. S Taniguchi N Suzuki M Masuda S Hisanaga T Iwatsubo M Goedert M Hasegawa 2005 Inhibition of heparin-induced tau filament formation by phenotiazines, polyphenols, and porphyrins J Biol Chem 280 9 7614 7623
53. J Tomaščiková J Imrich I Danihel S Böhm P Kristian 2007 Heterocyclization of Acridin-9-yl Thiosemicarbazides with Dimethyl Acetylenedicarboxylate Coll Czech Chem Commun 72 347 362
54. J Tomaščiková I Danihel S Böhm J Imrich P Kristian I Potocnak I Cejka KD Klika 2008 Molecular and solid-state structure of methyl [2-(acridin-9-ylimino)-3-(tert-butylamino)-4-oxothiazolidin-5-ylidene] acetate J Mol Struct 875 419 426
55. S Valleix S Drunat JB Philit D Adoue JC Piette D Droz 2002 Hereditary renal amyloidosis caused by a new variant lysozyme W64R in a French family Kidney Int 61 907 912
56. MNN Vieira JD Figueroa-Villar MNL Meirelles ST Ferreira FG De Felice 2006 Small Molecule Inhibitors of Lysozyme Amyloid Aggregation Cell Biochem Biophys 44 549 553
57. MNN Vieira L Forny-Germano LM Saraiva A Sebollela AMB Martinez J-C Houzel FG De Felice ST Ferreira 2007 Soluble oligomers from a non-disease related protein mimic Aβ-induced tau hyperphosphorylation and neurodegeneration J Neurochem 103 736 748
58. BA Vernaglia J Huang ED Clark 2004 Guanidie hydrochloride can induce amyloid fiblril firmation from hen egg-white lysozyme Biomacromolecules 5 1362 1370
59. DM Walsh I Klyubin JV Fadeeva WK Cullen R Anwyl MS Wolfe MJ Rowan DJ Selkoe 2002 Naturally secreted oligomers of amyloid beta protein potently inhibit hippocampal long-term potentiation in vivo Nature 416 535 539
60. DM Walsh DJ Selkoe 2004 Oligomers on the brain: the emerging role of soluble protein aggregates in neurodegeneration Protein Pept Lett 11 3 213 228
61. J Wang DW Dickson JQ Trojanowski VM Lee 1999 The levels of soluble versus insoluble brain Abeta distinguish Alzheimeŕs disease from normal and pathologic aging Expert Neurol 158 328 337
62. CM Wischik PC Edwards RYK Lai M Roth CR Harrington 1996 Selective inhibition of Alzheimer disease-like tau aggregation by phenothiazines PNAS 93 20 11213 11218
63. M Yazaki SA Farrell MD Benson 2003 A novel lysozyme mutation Phe57Ile associated with hereditary renal amyloidosis Kidney Int 63 1652 1657