Anti-amyloidogenic effects of soybean isoflavones in vitro: Fluorescence spectroscopy demonstrating direct binding to Aβ monomers, oligomers and fibrils

Mie Hirohata1,2, Kenjiro Ono1, Jun-ichi Takasaki1, Ryoichi Takahashi1, Tokuhei Ikeda1, Akiyoshi Morinaga1, Masahito Yamada1
1Department of Neurology and Neurobiology of Aging, Kanazawa University Graduate School of Medical Science, Kanazawa 920‐8640, Japan
2Department of Neurology, National Hospital Organization Nanao National Hospital, Nanao 926‐8531, Japan

Tài liệu tham khảo

Teplow, 1998, Structural and kinetic features of amyloid β-protein fibrillogenesis, Amyloid, 5, 121, 10.3109/13506129808995290 Pike, 1995, Structure-activity analyses of β-amyloid peptides: contributions of the β25–35 region to aggregation and neurotoxicity, J. Neurochem., 64, 253, 10.1046/j.1471-4159.1995.64010253.x Klein, 2004, Small assemblies of unmodified amyloid β-protein are the proximate neurotoxin in Alzheimer's disease, Neurobiol. Aging, 25, 569, 10.1016/j.neurobiolaging.2004.02.010 Klyubin, 2005, Amyloid β protein immunotherapy neutralizes Aβ oligomers that disrupt synaptic plasticity in vivo, Nat. Med., 11, 556, 10.1038/nm1234 Cheng, 2007, Accelerating amyloid-β fibrillization reduces oligomer levels and functional deficits in Alzheimer disease mouse models, J. Biol. Chem., 282, 23818, 10.1074/jbc.M701078200 Haass, 2007, Soluble protein oligomers in neurodegeneration: lessons from the Alzheimer's amyloid β-peptide, Nat. Rev. Mol. Cell Biol., 8, 101, 10.1038/nrm2101 Walsh, 2007, Aβ oligomers—a decade of discovery, J. Neurochem., 101, 1172, 10.1111/j.1471-4159.2006.04426.x Ono, 2003, Potent anti-amyloidogenic and fibril-destabilizing effects of polyphenols in vitro: implications for the prevention and therapeutics of Alzheimer's disease, J. Neurochem., 87, 172, 10.1046/j.1471-4159.2003.01976.x Porat, 2006, Inhibition of amyloid fibril formation by polyphenols: structural similarity and aromatic interactions as a common inhibition mechanism, Chem. Biol. Drug Des., 67, 27, 10.1111/j.1747-0285.2005.00318.x Ono, 2008, Effects of grape seed-derived polyphenols on amyloid β-protein self-assembly and cytotoxicity, J. Biol. Chem., 283, 32176, 10.1074/jbc.M806154200 Oomen, 2009, Resveratrol preserves cerebrovascular density and cognitive function in aging mice, Front. Aging Neurosci., 1, 4, 10.3389/neuro.24.004.2009 Letenneur, 1993, Wine consumption in the elderly, Ann. Intern. Med., 118, 317, 10.7326/0003-4819-118-4-199302150-00028 Truelsen, 2002, Amount and type of alcohol and risk of dementia: the Copenhagen City Heart Study, Neurology, 59, 1313, 10.1212/01.WNL.0000031421.50369.E7 Wang, 2001, The neuroprotective effects of phytoestrogens on amyloid β protein-induced toxicity are mediated by abrogating the activation of caspase cascade in rat cortical neurons, J. Biol. Chem., 276, 5287, 10.1074/jbc.M006406200 Ma, 2010, A large-scale chemical screen for regulators of the arginase 1 promoter identifies the soy isoflavone daidzein as a clinically approved small molecule that can promote neuronal protection or regeneration via a cAMP-independent pathway, J. Neurosci., 30, 739, 10.1523/JNEUROSCI.5266-09.2010 Hirohata, 2007, Anti-amyloidogenic effect against Alzheimer's β-amyloid fibrils in vitro is exerted by preferential and reversible binding of flavonoids to the amyloid fibril structure, Biochemistry, 46, 1888, 10.1021/bi061540x Jarrett, 1993, Seeding “one-dimensional crystallization” of amyloid: a pathogenic mechanism in Alzheimer's disease and scrapie?, Cell, 73, 1055, 10.1016/0092-8674(93)90635-4 Naiki, 1999, Kinetic analysis of amyloid fibril formation, Methods Enzymol., 309, 305, 10.1016/S0076-6879(99)09022-9 Bitan, 2003, Amyloid β-protein (Aβ) assembly: Aβ40 and Aβ42 oligomerize through distinct pathways, Proc. Natl. Acad. Sci. U. S. A., 100, 330, 10.1073/pnas.222681699 Ono, 2010, Effects of the English (H6R) and Tottori (D7N) familial Alzheimer disease mutations on amyloid β-protein assembly and toxicity, J. Biol. Chem., 285, 23186, 10.1074/jbc.M109.086496 Dufour, 2005, Flavonoid-serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy, Biochim. Biophys. Acta, 1721, 164, 10.1016/j.bbagen.2004.10.013 Radović, 2006, Genistein and other soya isoflavones are potent ligands for transthyretin in serum and cerebrospinal fluid, Br. J. Nutr., 95, 1171, 10.1079/BJN20061779 Adlercreutz, 1994, Determination of lignans and isoflavonoids in plasma by isotope dilution gas chromatography–mass spectrometry, Cancer Detect. Prev., 18, 259 Zeleniuch-Jacquotte, 1998, Reliability of serum measurements of lignans and isoflavonoid phytoestrogens over a two-year period, Cancer Epidemiol. Biomarkers Prev., 7, 885 Doerge, 2002, Goitrogenic and estrogenic activity of soy isoflavones, Environ. Health Perspect., 110, 349S, 10.1289/ehp.02110s3349 Manach, 2005, Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies, Am. J. Clin. Nutr., 81, 230S, 10.1093/ajcn/81.1.230S Youdim, 2004, Flavonoids and the brain: interactions at the blood–brain barrier and their physiological effects on the central nervous system, Free Radic. Biol. Med., 37, 1683, 10.1016/j.freeradbiomed.2004.08.002 Wang, 2008, Grape-derived polyphenolics prevent Aβ oligomerization and attenuate cognitive deterioration in a mouse model of Alzheimer's disease, J. Neurosci., 28, 6388, 10.1523/JNEUROSCI.0364-08.2008 Wang, 2012, Brain-targeted proanthocyanidin metabolites for Alzheimer's disease treatment, J. Neurosci., 32, 5144, 10.1523/JNEUROSCI.6437-11.2012 Ma, 2010, Genistein as a neuroprotective antioxidant attenuates redox imbalance induced by β-amyloid peptides 25–35 in PC12 cells, Int. J. Dev. Neurosci., 28, 289, 10.1016/j.ijdevneu.2010.03.003 Vallés, 2008, Oestradiol or genistein rescues neurons from amyloid β-induced cell death by inhibiting activation of p38, Aging Cell, 7, 112, 10.1111/j.1474-9726.2007.00356.x Vallés, 2010, Estradiol or genistein prevent Alzheimer's disease-associated inflammation correlating with an increase PPARγ expression in cultured astrocytes, Brain Res., 1312, 138, 10.1016/j.brainres.2009.11.044 Hsieh, 2009, Soy isoflavones attenuate oxidative stress and improve parameters related to aging and Alzheimer's disease in C57BL/6J mice treated with D-galactose, Food Chem. Toxicol., 47, 625, 10.1016/j.fct.2008.12.026 Gutierrez-Zepeda, 2005, Soy isoflavone glycitein protects against β amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans, BMC Neurosci., 6, 54, 10.1186/1471-2202-6-54