N′-benzylidene-benzohydrazides as novel and selective tau-PHF ligands

Journal of Alzheimer's Disease

Volumn 27, Issue 4, 2011, Pages 835-843

  Taghavi, Ali ^a   Nasir, Samir ^a   Pickhardt, Marcus ^b   Haußen, Roland Heyny Von ^c   Mall, Gerhard ^c   Mandelkow, Eckhard ^b   Mandelkow, Eva Maria ^b   Schmidt, Boris ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b MAX PLANCK UNIT FOR STRUCTURAL MOLECULAR BIOLOGY   (Germany)

^c KLINIKUM DARMSTADT   (Germany)

Author keywords

Alzheimer's disease; amphiphilic ligands; amphiphilicity; amyloid ; neurofibrillary tangle; N benzylidene benzohydrazide; paired helical filament; selective tau ligands; tau; tau and PHF proteins

Indexed keywords

AMYLOID BETA PROTEIN[1-42]; LIGAND; N' BENZYLIDENE BENZOHYDRAZIDE; TAU PROTEIN; UNCLASSIFIED DRUG; 1,2 DIBENZOYL TERT BUTYLHYDRAZINE; 1,2-DIBENZOYL-TERT-BUTYLHYDRAZINE; 4',6 DIAMIDINO 2 PHENYLINDOLE; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN (1 42); AMYLOID BETA-PROTEIN (1-42); DIAGNOSTIC AGENT; HYDRAZINE DERIVATIVE; INDOLE DERIVATIVE; PEPTIDE FRAGMENT;

AGED; ALZHEIMER DISEASE; ARTICLE; CASE REPORT; FEMALE; HISTOCHEMISTRY; HUMAN; HUMAN TISSUE; MALE; NEUROFIBRILLARY TANGLE; PAIRED HELICAL FILAMENT; PRIORITY JOURNAL; SENILE PLAQUE; AMYLOID PLAQUE; BRAIN; CHEMISTRY; DRUG EFFECT; IC 50; METABOLISM; PATHOLOGY;

AGED, 80 AND OVER; ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; BRAIN; FEMALE; HUMANS; HYDRAZINES; INDOLES; INHIBITORY CONCENTRATION 50; LIGANDS; MALE; NEUROFIBRILLARY TANGLES; PEPTIDE FRAGMENTS; PLAQUE, AMYLOID; TAU PROTEINS;

EID: 84455173802     PISSN: 13872877     EISSN: 18758908     Source Type: Journal    
DOI: 10.3233/JAD-2011-111238     Document Type: Article

References (17)

1. Pickhardt M, Gazova Z, von Bergen M, Khlistunova I, Wang Y, Hascher A, Mandelkow E-M, Biernat J, Mandelkow E (2005) Anthraquinones inhibit tau aggregation and dissolve Alzheimers paired helical filaments in vitro and in cells. J Biol Chem 280, 3628-3635 (Pubitemid 40223830)
2. Friedhoff P, von Bergen M, Mandelkow EM, Davies P, Mandelkow E (1998) A nucleated assembly mechanism of Alzheimer paired helical filaments. Proc Natl Acad Sci U S A 95, 15712-15717 (Pubitemid 29018765)
3. Mirra SS (1997) The CERAD Neuropathology protocol and consensus recommendations for the postmortem diagnosis of Alzheimers disease: A commentary. Neurobiol Aging 18, S91-S94 (Pubitemid 27454705)
4. Lockhart A, Ye L, Judd DB, Merritt AT, Lowe PN, Morgenstern JL, Hong G, Gee AD, Brown J (2005) Evidence for the presence of three distinct binding sites for the thioflavin t class of Alzheimers disease pet imaging agents on β-amyloid peptide fibrils. J Biol Chem 280, 7677-7684 (Pubitemid 40349660)
5. LaFerla FM, Oddo S (2005) Alzheimers disease: Aβ, tau and synaptic dysfunction. Trends Mol Med 11, 170-176
6. Clark CM, Karlawish JHT (2003) Alzheimer disease: Current concepts and emerging diagnostic and therapeutic strategies. Ann Intern Med 138, 400-410 (Pubitemid 36262651)
7. Nordberg A (2008) Amyloid plaque imaging in vivo: Current achievement and future prospects. Eur J Nucl Med Mol Imaging 35(Suppl 1), S46-S50
8. Klunk WE, Lopresti BJ, Ikonomovic MD, Lefterov IM, Koldamova RP, Abrahamson EE, Debnath ML, Holt DP, Huang G-f, Shao L, DeKosky ST, Price JC, Mathis CA (2005) Binding of the positron emission tomography tracer pittsburgh compound-B reflects the amount of amyloid-beta in Alzheimers disease brain but not in transgenic mouse brain. J Neurosci 25, 10598-10606 (Pubitemid 41681907)
9. Cai L, Cuevas J, Temme S, Herman MM, Dagostin C, Widdowson DA, Innis RB, Pike VW (2007) Synthesis and structure-affinity relationships of new 4-(6-Iodo-Himidazo 1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine derivatives as ligands for human β-amyloid plaques. J Med Chem 50, 4746-4758 (Pubitemid 47463247)
10. Chen X (2006) QSAR and primary docking studies of transstilbene (TSB) series of imaging agents for beta]-amyloid plaques. J Mol Struct-THEOCHEM 763, 83-89
11. Pickhardt M, Larbig G, Khlistunova I, Coksezen A, Meyer B, Mandelkow E-M, Schmidt B, Mandelkow E (2007) Phenylthiazolyl-hydrazide and its derivatives are potent inhibitors of tau aggregation and toxicity in vitro and in cells. Biochemistry 46, 10016-10023 (Pubitemid 47378592)
12. Lee HJ, Lim SJ, Oh SJ, Moon DH, Kim DJ, Tae J, Yoo KH (2008) Isoindol-1,3-dione and isoindol-1-one derivatives with high binding affinity to beta-amyloid fibrils. Bioorg Med Chem Lett 18, 1628-1631 (Pubitemid 351324869)
13. Zhang W, Kung M-P, Oya S, Hou C, Kung HF (2007) 18Flabeled styrylpyridines as PET agents for amyloid plaque imaging. Nucl Med Biol 34, 89-97 (Pubitemid 46038150)
14. Johnson AE, Jeppsson F, Sandell J, Wensbo D, Neelissen JAM, Jureus A, Stroem P, Norman H, Farde L, Svensson SPS (2009) AZD2184:Aradioligand for sensitive detection of beta -amyloid deposits. J Neurochem 108, 1177-1186
15. Landau M, Sawaya MR, Fauli KF, Laganowsky A, Jiang L, Sievers SA, Liu J, Barrio JR, Eisenberg D (2011) Towards a pharmacophore for amyloid. PLOS Biol 9, e1001080
16. Jensen JR, Cisek K, Funk KE, Naphade S, Schafer KN,Kuret J (2011) Research towards tau imaging. In. Handbook of Imaging the Alzheimer Brain. Ashford JW, Rosen A, Adamson M, Bayley P, Sabri O, Furst A, Black SE, Weiner M, eds. IOS Press, Amsterdam, pp. 277-287
17. Narlawar R, Pickhardt M, Leuchtenberger S, Baumann K, Krause S, Dyrks T, Weggen S, Mandelkow E, Schmidt B (2008) Curcumin derived pyrazoles and isoxazoles - Swiss army knives or blunt tools for Alzheimers disease? Chem Med Chem 3, 165-172.