"Clicked" sugar.curcumin conjugate: Modulator of amyloid-βand tau peptide aggregation at ultralow concentrations

ACS Chemical Neuroscience

Volumn 2, Issue 12, 2011, Pages 694-699

  Dolai, Sukanta ^a   Shi, Wei ^b   Corbo, Christopher ^c   Sun, Chong ^a   Averick, Saadyah ^a   Obeysekera, Dinali ^a   Farid, Mina ^c   Alonso, Alejandra ^c   Banerjee, Probal ^a   Raja, Krishnaswami ^a  

^a Department of Chemistry ^*  (United States)

^b Felician College   (United States)

^c CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

"click" reaction; Alzheimer's disease (AD); amyloid ; antioxidant potential; curcumin; tau peptide

Indexed keywords

AMYLOID BETA PROTEIN; CURCUMIN; TAU PROTEIN;

ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTEIN AGGREGATION; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

" CLICK" REACTION; ALZHEIMER'S DISEASE (AD); AMYLOID-Β; ANTIOXIDANT POTENTIAL; CURCUMIN; TAU PEPTIDE;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; ANTIOXIDANTS; CELLS, CULTURED; CURCUMIN; GALACTOSE; HIPPOCAMPUS; HUMANS; MICE; TAU PROTEINS;

EID: 84555177564     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn200088r     Document Type: Article

References (41)

1. Abbott, A. (2011) Dementia: a problem for our age Nature 475 (7355) S2-S4
2. Fowler, D. M. and Kelly, J. W. (2009) Aggregating knowledge about prions and amyloid Cell 137 (1) 20-22
3. Rauk, A. (2009) The chemistry of Alzheimer's disease Chem Soc Rev. 38 (9) 2698-2715
4. Rostagno, A., Holton, J. L., Lashley, T., Revesz, T., and Ghiso, J. (2010) Cerebral amyloidosis: amyloid subunits, mutants and phenotypes Cell. Mol. Life Sci. 67 (4) 581-600
5. Smith, T. J., Stains, C. I., Meyer, S. C., and Ghosh., I. (2006) Inhibition of beta-amyloid fibrillization by directed evolution of a beta-sheet presenting miniature protein J. Am. Chem. Soc. 128 (45) 14456-14457 (Pubitemid 44749835)
6. Alonso, A. C., Li, B., Grundke-Iqbal, I., and Iqbal, K. (2008) Mechanism of tau-induced neurodegeneration in Alzheimer disease and related tauopathies Curr. Alzheimer Res. 5 (4) 375-384
7. Alonso, A. D., Di-Clerico, J., Li, B., Corbo, C. P., Alaniz, M. E., Grundke-Iqbal, I., and Iqbal., K. (2010) Phosphorylation of tau at Thr212, Thr231, and Ser262 combined causes neurodegeneration J. Biol. Chem. 285 (40) 30851-30860
8. Kayed, R., Head, E., Thompson, J. L., McIntire, T. M., Milton, S. C., Cotman, C. W., and Glabe, C. G (2003) Common structure of soluble amyloid oligomers implies common mechanism of pathogenesis Science 300 (5618) 486-489 (Pubitemid 36444329)
9. Curtain, C. C., Ali, F., Volitakis, I., Cherny, R. A., Norton, R. S., Beyreuther, K., Barrow, C. J., Masters, C. L., Bush, A. I., and Barnham, K. J. (2001) Alzheimer's Disease Amyloid-β Binds Copper and Zinc to Generate an Allosterically Ordered Membrane-penetrating Structure Containing Superoxide Dismutase-like Subunits J. Biol. Chem. 276, 20466-20473
10. Nitsch, R. M. and Hock, C. (2008) Targeting beta-amyloid pathology in Alzheimer's disease with Abeta immunotherapy Neurotherapeutics 5 (3) 415-420 (Pubitemid 351952496)
11. LeVine, H. (2002) The challenge of inhibiting Abeta polymerization Curr. Med. Chem. 9 (11) 1121-1133
12. Walsh, D. M., Townsend, M., Podlisny, M. B., Shankar, G. M., Fadeeva, J. V., El- Agnaf, O., Hartley, D. M., and Selkoe, D. J. (2005) Certain inhibitors of synthetic amyloid beta-peptide (Abeta) fibrillogenesis block oligomerization of natural Abeta and thereby rescue long-term potentiation J. Neurosci. 25 (10) 2455-2462 (Pubitemid 40365155)
13. Goryunov, D. and Liem, R. K. (2007) CHIP-ping away at tau J. Clin. Invest. 117 (3) 590-592 (Pubitemid 46348514)
14. Asuni, A. A., Boutajangout, A., Quartermain, D., and Sigurdsson, E. M. (2007) Immunotherapy targeting pathological tau conformers in a tangle mouse model reduces brain pathology with associated functional improvements J. Neurosci. 27 (34) 9115-9129 (Pubitemid 47312068)
15. Ringman, J. M., Frautschy, S. A., Cole, G. M., Masterman, D. L., and Cummings, J. L. (2005) A potential role of the curry spice curcumin in Alzheimer's disease Curr. Alzheimer Res. 2 (2) 131-136 (Pubitemid 40862872)
16. Raja, K. S., Balambika, R., Dolai, S., and Shi, W. (2009) The Concept of a Green Drug, Curcumin and its derivatives as a model-system Mini-Rev. Org. Chem. 6 (2) 152-158
17. Cole, G. M., Teter, B., and Frautschy, S. A. (2007) Neuroprotective effects of curcumin Adv. Exp. Med. Biol. 595, 197-212
18. Shi, W., Dolai, S., Rizk, S., Hussain, A., Tariq, H., Averick, S., L'Amoreaux, W., El ldrissi, A., Banerjee, P., and Raja, K. (2007) Synthesis of monofunctional curcumin derivatives, clicked curcumin dimer, and a PAMAM dendrimer curcumin conjugate for therapeutic applications Org. Lett. 9 (26) 5461-5464
19. Strimpakos, A. S. and Sharma, R. A. (2008) Curcumin: preventive and therapeutic properties in laboratory studies and clinical trials Antioxid. Redox Signaling 10 (3) 511-545
20. Jagetia, G. C. and Aggarwal, B. B. (2007) "Spicing up" of the immune system by curcumin J. Clin. Immunol. 27 (1) 19-35
21. Lim, G. P., Chu, T., Yang, F., Beech, W., Frautschy, S. A., and Cole, G. M. (2001) The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse J. Neurosci. 21 (21) 8370-8377 (Pubitemid 33051435)
22. Yang, F., Lim, G. P., Begum, A. N., Ubeda, O. J., Simmons, M. R., Ambegaokar, S. S., Chen, P., Kayed, R., Glabe, C. G., Frautschy, S. A., and Cole, G. M. (2005) Curcumin Inhibits Formation of Amyloid β Oligomers and Fibrils, Binds Plaques, and Reduces Amyloid in Vivo J. Biol. Chem. 280 (7) 5892-5901 (Pubitemid 40280072)
23. Ma, Q. L., Yang, F., Calon, F., Ubeda, O. J., Hansen, J. E., Weisbart, R. H., Beech, W., Frautschy, S. A., and Cole, G. M. (2008) P21- activated kinase aberrant activation and translocation in Alzheimer's disease pathogenesis J. Biol. Chem. 283 (20) 14132-14143
24. Rojas, P. M., Shi, W., Davidowitz, E. J., Dolai, S., Moe, J. G., Averick, S., and Raja, K. S. (2008) Targeting tau oligomers with curcumin derivatives for developing therapeutics for Alzheimer's disease and other tauopathies. Neuroscience, Abstract # 2008-S-114182- SfN.
25. Narlawar, R., Pickhardt, M., Leuchtenberger, S., Baumann, K., Krause, S., Dyrks, T., Weggen, S., Mandelkow, E., and Schmidt, B. (2008) Curcumin-Derived Pyrazoles and Isoxazoles: Swiss Army Knives or Blunt Tools for Alzheimer's Disease? ChemMedChem 3 (1) 165-172
26. 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 (1) 27-37 (Pubitemid 43881385)
27. Nakagami, Y., Nishimura, S., Murasugi, T., Kaneko, I., Meguro, M., Marumoto, S., Kogen, H., Koyama, K., and Oda., T. (2002) A novel beta-sheet breaker, RS-0406, reverses amyloid beta-induced cytotoxicity and impairment of long-term potentiation in vitro Br. J. Pharmacol. 137, 676-682 (Pubitemid 35333093)
28. Barik, A., Mishra, B., Shen, L., Mohan, H., Kadam, R. M., Dutta, S., Zhang, H. Y., and Priyadarsini, K. I. (2005) Evaluation of a new copper(II)-curcumin complex as superoxide dismutase mimic and its free radical reactions Free Radical Biol. Med. 39 (6) 811-822 (Pubitemid 41139894)
29. Hung, Y. H., Bush, A. I., and Cherny, R. A. (2010) Copper in the brain and Alzheimer's disease J. Biol. Inorg. Chem. 15 (1) 61-76
30. Cheng, A. L., Hsu, C. H., Lin, J. K., Hsu, M. M., Ho, Y. F., Shen, T. S., Ko, J. Y., Lin, J. T., Lin, B. R., Wu, M. S., Yu, H. S., Jee, S. H., Chen, G. S., Chen, T. M., Chen, C. A., Lai, M. K., Pu, Y. S., Pan, M. H., Wang, Y. J, Tsai, C. C., and Hsieh, C. Y. (2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions Anticancer Res. 21, 2895-2900
31. Anand, P., Kunnumakkara, A. B., Newman, R. A., and Aggarwal, B. B. (2007) Bioavailability of curcumin: problems andn promises Mol. Pharmaceutics 4 (6) 807-818
32. Lapchak, P. A. and McKim, J. M., Jr. (2011) CeeTox Analysis of CNB-001 a Novel Curcumin-Based Neurotrophic/Neuroprotective lead compound to Treat Stroke: Comparison with NXY-059 and Radicut Transl. Stroke Res. 2 (1) 51-59
33. Donaldson, K. and Seaton, A. (2007) The Janus Faces of Nanoparticles J. Nanosci. Nanotechnol. 7 (12) 4607-4611
34. Koziara, J. M., Lockman, P. R., Allen, D. D., and Mumper, R. J. (2006) The Blood-Brain Barrier and Brain Drug Delivery J. Nanosci. Nanotechnol. 6 (9-10) 2712-2735 (Pubitemid 44579941)
35. Lenhart, J. A., Ling, X., Gandhi, R., Guo, T. L., Gerk, P. M., Brunzell, D. H., and Zhang, S. (2010) Clicked" Bivalent Ligands Containing Curcumin and Cholesterol As Multifunctional Aβ Oligomerization Inhibitors: Design, Synthesis, and Biological Characterization J. Med. Chem. 53 (16) 6198-6209
36. Ingolfsson, H. I., Koeppe, R. E., II, and Andersen, O. S. (2007) Curcumin is a Modulator of Bilayer Material Properties Biochemistry 46 (36) 10384-10391 (Pubitemid 350067631)
37. Purkayastha, S., Berliner, A., Fernando, S. S., Ranasinghe, B., Ray, I., Tariq, H., and Banerjee, P. (2009) Curcumin Blocks Brain Tumor Formation Brain Res. 1266C, 130-138
38. von Bergen, M., Friedhoff, P., Biernat, J., Heberle, J., Mandelkow, E. M., and Mandelkow, E. (2000) Proc. Natl. Acad. Sci. U.S.A. 97, 5129-5134
39. Hudson, S. A., Ecroyd, H., Kee, T. W., and Carver, J. A. (2009) FEBS J. 276, 5960-5972
40. Jayaprakasha, G. K., Jaganmohan Rao, L., and Sakariah, K. K. (2006) Antioxidant activities of curcumin, demethoxycurcumin and bisdemethoxycurcumin Food Chem. 98 (4) 720-724
41. Pardridges, W. M., Boado, R. J., and Farrell, C. R. (1990) Brain-type glucose transporter (GLUT-1) is selectively localized to the blood-brain barrier. Studies with quantitative western blotting and in situ hybridization J. Biol. Chem. 265 (29) 18035-18040