Molecular hairpin: A possible model for inhibition of tau aggregation by tannic acid

Biochemistry

Volumn 52, Issue 11, 2013, Pages 1893-1902

  Yao, Junliang ^a   Gao, Xing ^a   Sun, Wenliang ^a   Yao, Tianming ^a   Shi, Shuo ^a   Ji, Liangnian ^b  

^a TONGJI UNIVERSITY   (China)

^b SUN YAT SEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATION INHIBITORS; CIRCULAR DICHROISM SPECTRA; CONFORMATIONAL TRANSITIONS; ELECTRICAL INTERACTION; ISOTHERMAL TITRATION CALORIMETRY; MICROTUBULE-BINDING DOMAINS; MOLECULAR DOCKING SIMULATIONS; RANDOM-COIL STRUCTURES;

AGGLOMERATION; BINDING ENERGY; ELECTRON MICROSCOPES; ELECTRON MICROSCOPY; HYDROGEN BONDS; MODEL STRUCTURES; TANNINS;

PEPTIDES;

TANNIN; TAU PROTEIN;

ARTICLE; COMPETITIVE INHIBITION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ELECTRON MICROSCOPY; FLUORESCENCE ANALYSIS; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; IN VITRO STUDY; ISOTHERMAL TITRATION CALORIMETRY; MICROTUBULE; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTEIN AGGREGATION; PROTEIN DOMAIN;

ALZHEIMER DISEASE; AMINO ACID SEQUENCE; GALLIC ACID; HUMANS; MOLECULAR DOCKING SIMULATION; MOLECULAR SEQUENCE DATA; PROTEIN CONFORMATION; TANNINS; TAU PROTEINS; THERMODYNAMICS;

EID: 84875431905     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi400240c     Document Type: Article

References (42)

1. Selkoe, D. J. and Schenk, D. (2003) Alzheimer's Disease: Molecular Understanding Predicts Amyloid-Based Therapeutics Annu. Rev. Pharmacol. 43, 545-584
2. Mandelkow, E.-M. and Mandelkow, E. (1998) Tau in Alzheimer's disease Trends Cell Biol. 8, 425-427
3. Lee, V. M.-Y., Goedert, M., and Trojanowski, J. Q. (2001) Neurodegenerative Tauopathies Annu. Rev. Neurosci. 24, 1121-1159
4. Iqbal, K., Liu, F., Gong, C.-X., Alonso, A., and Grundke-Iqbal, I. (2009) Mechanisms of tau-induced neurodegeneration Acta Neuropathol. 118, 53-69
5. Inouye, H., Sharma, D., Goux, W. J., and Kirschner, D. A. (2006) Structure of Core Domain of Fibril-Forming PHF/Tau Fragments Biophys. J. 90, 1774-1789
6. Arriagada, P. V., Growdon, J. H., Hedley-Whyte, E. T., and Hyman, B. T. (1992) Neurofibrillary tangles but not senile plaques parallel duration and severity of Alzheimer's disease Neurology 42, 631
7. Iqbal, K., del C. Alonso, A., Chen, S., Chohan, M. O., El-Akkad, E., Gong, C.-X., Khatoon, S., Li, B., Liu, F., Rahman, A., Tanimukai, H., and Grundke-Iqbal, I. (2005) Tau pathology in Alzheimer disease and other tauopathies Biochim. Biophys. Acta 1739, 198-210
8. Meraz-Ríos, M. A., Lira-De León, K. I., Campos-Peña, V., De Anda-Hernández, M. A., and Mena-López, R. (2010) Tau oligomers and aggregation in Alzheimer's disease J. Neurochem. 112, 1353-1367
9. Berger, Z., Roder, H., Hanna, A., Carlson, A., Rangachari, V., Yue, M., Wszolek, Z., Ashe, K., Knight, J., Dickson, D., Andorfer, C., Rosenberry, T. L., Lewis, J., Hutton, M., and Janus, C. (2007) Accumulation of Pathological Tau Species and Memory Loss in a Conditional Model of Tauopathy J. Neurosci. 27, 3650-3662
10. Maeda, S., Sahara, N., Saito, Y., Murayama, M., Yoshiike, Y., Kim, H., Miyasaka, T., Murayama, S., Ikai, A., and Takashima, A. (2007) Granular Tau Oligomers as Intermediates of Tau Filaments Biochemistry 46, 3856-3861
11. Bulic, B., Pickhardt, M., Khlistunova, I., Biernat, J., Mandelkow, E.-M., Mandelkow, E., and Waldmann, H. (2007) Rhodanine-Based Tau Aggregation Inhibitors in Cell Models of Tauopathy Angew. Chem., Int. Ed. 46, 9215-9219
12. Khlistunova, I., Pickhardt, M., Biernat, J., Wang, Y., Mandelkow, E.-M., and Mandelkow, E. (2007) Inhibition of Tau Aggregation in Cell Models of Tauopathy Curr. Alzheimer Res. 4, 544-546
13. Gregor, L., Marcus, P., David, G. L., Boris, S., and Eckhard, M. (2007) Screening for Inhibitors of Tau Protein Aggregation into Alzheimer Paired Helical Filaments: A Ligand Based Approach Results in Successful Scaffold Hopping Curr. Alzheimer Res. 4, 315-323
14. Pickhardt, M., Bergen, M. v., Gazova, Z., Hascher, A., Biernat, J., Mandelkow, E.-M., and Mandelkow, E. (2005) Screening for Inhibitors of Tau Polymerization Curr. Alzheimer Res. 2, 219-226
15. Pickhardt, M., Biernat, J., Khlistunova, I., Wang, Y. P., Gazova, Z., Mandelkow, E. M., and Mandelkow, E. (2007) N-Phenylamine Derivatives as Aggregation Inhibitors in Cell Models of Tauopathy Curr. Alzheimer Res. 4, 397-402
16. Bulic, B., Pickhardt, M., Mandelkow, E.-M., and Mandelkow, E. (2010) Tau protein and tau aggregation inhibitors Neuropharmacology 59, 276-289
17. Brunden, K. R., Ballatore, C., Crowe, A., Smith, A. B., III, Lee, V. M., and Trojanowski, J. Q. (2010) Tau-directed drug discovery for Alzheimer's disease and related tauopathies: A focus on tau assembly inhibitors Exp. Neurol. 223, 304-310
18. Bulic, B., Pickhardt, M., Schmidt, B., Mandelkow, E.-M., Waldmann, H., and Mandelkow, E. (2009) Development of Tau Aggregation Inhibitors for Alzheimer's Disease Angew. Chem., Int. Ed. 48, 1740-1752
19. Chang, E., Congdon, E. E., Honson, N. S., Duff, K. E., and Kuret, J. (2009) Structure-Activity Relationship of Cyanine Tau Aggregation Inhibitors J. Med. Chem. 52, 3539-3547
20. Zheng, J., Liu, C., Sawaya, M. R., Vadla, B., Khan, S., Woods, R. J., Eisenberg, D., Goux, W. J., and Nowick, J. S. (2011) Macrocyclic β-Sheet Peptides That Inhibit the Aggregation of a Tau-Protein-Derived Hexapeptide J. Am. Chem. Soc. 133, 3144-3157
21. Taniguchi, S., Suzuki, N., Masuda, M., Hisanaga, S.-i., Iwatsubo, T., Goedert, M., and Hasegawa, M. (2005) Inhibition of Heparin-induced Tau Filament Formation by Phenothiazines, Polyphenols, and Porphyrins J. Biol. Chem. 280, 7614-7623
22. Costa, E., Coelho, M., Ilharco, L. M., Aguiar-Ricardo, A., and Hammond, P. T. (2011) Tannic Acid Mediated Suppression of PNIPAAm Microgels Thermoresponsive Behavior Macromolecules 44, 612-621
23. Han, L.-J., Shi, S., Zheng, L.-F., Yang, D.-J., Yao, T.-M., and Ji, L.-N. (2010) Flavonoids Inhibit Heparin-Induced Aggregation of the Third Repeat (R3) of Microtubule-Binding Domain of Alzheimer's Tau Protein Bull. Chem. Soc. Jpn. 83, 911-922
24. Porat, Y., Abramowitz, A., and Gazit, E. (2006) Inhibition of Amyloid Fibril Formation by Polyphenols: Structural Similarity and Aromatic Interactions as a Common Inhibition Mechanism Chem. Biol. Drug Des. 67, 27-37
25. Ono, K., Hasegawa, K., Naiki, H., and Yamada, M. (2004) Anti-amyloidogenic activity of tannic acid and its activity to destabilize Alzheimer's β-amyloid fibrils in vitro Biochim. Biophys. Acta 1690, 193-202
26. Tomoo, K., Yao, T.-M., Minoura, K., Hiraoka, S., Sumida, M., Taniguchi, T., and Ishida, T. (2005) Possible Role of Each Repeat Structure of the Microtubule-Binding Domain of the Tau Protein in In Vitro Aggregation J. Biochem. 138, 413-423
27. Jiang, L.-F., Yao, T.-M., Zhu, Z.-L., Wang, C., and Ji, L.-N. (2007) Impacts of Cd(II) on the conformation and self-aggregation of Alzheimer's tau fragment corresponding to the third repeat of microtubule-binding domain Biochim. Biophys. Acta 1774, 1414-1421
28. 311) forming β structure Proc. Natl. Acad. Sci. U.S.A. 97, 5129-5134
29. Modi, S., Paine, M. J., Sutcliffe, M. J., Lian, L. Y., Primrose, W. U., Wolf, C. R., and Roberts, G. C. K. (1996) A Model for Human Cytochrome P450 2D6 Based on Homology Modeling and NMR Studies of Substrate Binding Biochemistry 35, 4540-4550
30. Frisch, M. J., et al. (2005) Gaussian 03, revision D.01, Gaussian Inc., Wallingford, CT.
31. Trott, O. and Olson, A. J. (2010) AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 31, 455-461
32. Goux, W. J., Kopplin, L., Nguyen, A. D., Leak, K., Rutkofsky, M., Shanmuganandam, V. D., Sharma, D., Inouye, H., and Kirschner, D. A. (2004) The Formation of Straight and Twisted Filaments from Short Tau Peptides J. Biol. Chem. 279, 26868-26875
33. Friedhoff, P., Schneider, A., Mandelkow, E.-M., and Mandelkow, E. (1998) Rapid Assembly of Alzheimer-like Paired Helical Filaments from Microtubule-Associated Protein Tau Monitored by Fluorescence in Solution Biochemistry 37, 10223-10230
34. Friedhoff, P., von Bergen, M., Mandelkow, E.-M., Davies, P., and Mandelkow, E. (1998) A nucleated assembly mechanism of Alzheimer paired helical filaments Proc. Natl. Acad. Sci. U.S.A. 95, 15712-15717
35. von Bergen, M., Barghorn, S., Biernat, J., Mandelkow, E.-M., and Mandelkow, E. (2005) Tau aggregation is driven by a transition from random coil to β sheet structure Biochim. Biophys. Acta 1739, 158-166
36. Minoura, K., Yao, T.-M., Tomoo, K., Sumida, M., Sasaki, M., Taniguchi, T., and Ishida, T. (2004) Different associational and conformational behaviors between the second and third repeat fragments in the tau microtubule-binding domain Eur. J. Biochem. 271, 545-552
37. Mizushima, F., Minoura, K., Tomoo, K., Sumida, M., Taniguchi, T., and Ishida, T. (2006) Fluorescence-coupled CD conformational monitoring of filament formation of tau microtubule-binding repeat domain Biochem. Biophys. Res. Commun. 343, 712-718
38. Miller, Y., Ma, B., and Nussinov, R. (2011) Synergistic Interactions between Repeats in Tau Protein and Aβ Amyloids May Be Responsible for Accelerated Aggregation via Polymorphic States Biochemistry 50, 5172-5181
39. Kabanov, A. V. and Batrakova, E. V. (2004) New Technologies for Drug Delivery across the Blood Brain Barrier Curr. Pharm. Des. 10, 1355-1363
40. Tucker, I. G., Yang, L., and Mujoo, H. (2012) Delivery of drugs to the brain via the blood brain barrier using colloidal carriers J. Microencapsulation 29, 475-486
41. Kreuter, J. (2012) Nanoparticulate systems for brain delivery of drugs Adv. Drug Delivery Rev. 64 (Suppl.) 213-222
42. Hossaina, S., Akaike, T., and Chowdhury, E. H. (2010) Current Approaches for Drug Delivery to Central Nervous System Curr. Drug Delivery 7, 389-397