Fluorinated benzofuran derivatives for PET imaging of β-amyloid plaques in alzheimer's disease brains

ACS Medicinal Chemistry Letters

Volumn 1, Issue 7, 2010, Pages 321-325

  Cheng, Yan ^a   Ono, Masahiro ^a   Kimura, Hiroyuki ^a   Kagawa, Shinya ^b   Nishii, Ryuichi ^b   Kawashima, Hidekazu ^a   Saji, Hideo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Shiga Medical Center Research Institute   (Japan)

Author keywords

Alzheimer's disease; benzofuran; fluorine 18; positron emission tomography (PET)

Indexed keywords

AMYLOID BETA PROTEIN[1-42]; BENZOFURAN DERIVATIVE; FLUORINE 18; TRACER;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; DRUG STRUCTURE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; WITTIG REACTION;

MUS;

EID: 77958092259     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100082x     Document Type: Article

References (27)

1. Selkoe, D. J. Alzheimer's Disease: Genes, Proteins, and Therapy Physiol. Rev. 2001, 81, 741-766
2. Hardy, J.; Selkoe, D. J. The Amyloid Hypothesis of Alzheimer's Disease: Progress and Problems on the Road to Therapeutics Science 2002, 297, 353-356
3. Selkoe, D. J. Imaging Alzheimer's Amyloid Nat. Biotechnol. 2000, 18, 823-824
4. Mathis, C. A.; Wang, Y.; Klunk, W. E. Imaging β-Amyloid Plaques and Neurofibrillary Tangles in the Aging Human Brain Curr. Pharm. Des. 2004, 10, 1469-1492
5. Nordberg, A. PET Imaging of Amyloid in Alzheimer's Disease Lancet Neurol. 2004, 3, 519-527
6. 11C-labeled Stilbene Derivatives as Aβ-Aggregate-Specific PET Imaging Agents for Alzheimer's Disease Nucl. Med. Biol. 2003, 30, 565-571
7. 11C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents J. Med. Chem. 2003, 46, 2740-2754
8. Klunk, W. E.; Engler, H.; Nordberg, A.; Wang, Y.; Blomqvist, G.; Holt, D. P. Imaging Brain Amyloid in Alzheimer's Disease with Pittsburgh Compound-B Ann. Neurol. 2004, 55, 306-319 (Pubitemid 38269583)
9. Kudo, Y.; Okamura, N.; Furumoto, S.; Tashiro, M.; Furukawa, K.; Maruyama, M.; Itoh, M.; Iwata, R.; Yanai, K.; Arai, H. 2-(2-[2-Dimethylaminothiazol-5-yl] ethenyl)-6-(2-[fluoro]ethoxy)benzoxazole: A Novel PET Agent for in vivo Detection of Dense Amyloid Plaques in Alzheimer's Disease Patients J. Nucl. Med. 2007, 48, 553-561
10. Small, G. W.; Kepe, V.; Ercoli, L. M.; Siddarth, P.; Bookheimer, S. Y.; Miller, K. J.; Lavretsky, H.; Burggren, A. C.; Cole, G. M.; Vinters, H. V.; Thompson, P. M.; Huang, S. C.; Satyamurthy, N.; Phelps, M. E.; Barrio, J. R. PET of Brain Amyloid and Tau in Mild Cognitive Impairment N. Engl. J. Med. 2006, 355, 2652-2663
11. Shoghi-Jadid, K.; Small, G. W.; Agdeppa, E. D.; Kepe, V.; Ercoli, L. M.; Siddarth, P.; Read, S.; Satyamurthy, N.; Petric, A.; Huang, S. C.; Barrio, J. R. Localization of Neurofibrillary Tangles and β-Amyloid Plaques in the Brains of Living Patients with Alzheimer Disease Am. J. Geriatr. Psychiatry 2002, 10, 24-35
12. 18F-BAY94-9172, A Novel PET Tracer: Proof of Mechanism Lancet Neurol. 2008, 7, 129-135
13. Zhang, W.; Oya, S.; Kung, M. P.; Hou, C.; Maier, D. L.; Kung, H. F. F-18 Polyethyleneglycol Stilbenes as PET Imaging Agents Targeting Aβ aggregates in the Brain Nucl. Med. Biol. 2005, 32, 799-809 (Pubitemid 41505313)
14. 18F-AV-45: A PET Imaging Agent for Aβ Plaques in the Brain J. Nucl. Med. 2009, 50, 1887-1894
15. 18F Stilbenes and Styrylpyridines for PET Imaging of Aβ Plaques in Alzheimer's Disease J. Med. Chem. 2010, 53, 933-941
16. 18F-GE067: A Radioligand for in vivo Brain Amyloid Imaging J. Nucl. Med. 2009, 50 (5) 818-822
17. Ono, M.; Kung, M. P.; Hou, C.; Kung, H. F. Benzofuran Derivatives as Aβ Aggregate Specific Imaging Agents for Alzheimer's Disease Nucl. Med. Biol. 2002, 29, 633-642
18. Ono, M.; Kawashima, H.; Nonaka, A.; Kawai, T.; Haratake, M.; Mori, H.; Kung, M. P.; Kung, H. F.; Saji, H.; Nakayama, M. Novel Benzofuran Derivatives for PET Imaging of β-Amyloid Plaques in Alzheimer's Disease Brains J. Med. Chem. 2006, 49, 2725-2730
19. Zhang, W.; Oya, S.; Kung, M. P.; Hou, C.; Maier, D. L.; Kung, H. F. F-18 Stilbenes as PET Imaging Agents for Detecting β-Amyloid Plaques in the Brain J. Med. Chem. 2005, 48, 5980-5988 (Pubitemid 41324608)
20. Yuan, W.; Berman, R. J.; Gelb, M. H. Synthesis and Evaluation of Phospholipid Analogues as Inhibitors of Cobra Venom Phospholipase A2 J. Am. Chem. Soc. 1987, 109, 8071-8081
21. Cox, D. P.; Terpinski, J.; Lawrynowicz, W. "Anhydrousa" Tetrabutylammonium Fluoride: A Mild but Highly Efficient Source of Nucleophilic Fluoride Ion J. Org. Chem. 1984, 49, 3216-3219
22. Xu, B.; Stephens, A.; Kirschenheuter, G.; Greslin, A. F.; Cheng, X.; Sennelo, J.; Cattaneo, M.; Zighetti, M. L.; Chen, A.; Kim, S. A.; Kim, H. S.; Bischofberger, N.; Cook, G.; Jacobson, K. A. Acyclic Analogues of Aaenosine Bisphosphates as P2Y Receptor Antagonists: Phosphate Substitution Leads to Multiple Pathways of Inhibition of Platelet Aggregation J. Med. Chem. 2002, 45, 5694-5709
23. Ono, M.; Watanabe, R.; Kawashima, H.; Cheng, Y.; Kimura, H.; Watanabe, H.; Haratake, M.; Saji, H.; Nakayama, M. Fluoro-Pegylated Chalcones as Positron Emission Tomography Probes for in vivo Imaging of β-amyloid Plaques in Alzheimer's Disease J. Med. Chem. 2009, 52, 6394-6401
24. Kung, M. P.; Hou, C.; Zhuang, Z. P.; Skovronsky, D.; Kung, H. F. Binding of Two Potential Imaging Agents Targeting Amyloid Plaques in Postmortem Brain Tissues of Patients with Alzheimer's Disease Brain Res. 2004, 1025, 98-105
25. Kung, M. P.; Hou, C.; Zhuang, Z. P.; Cross, A. J.; Maier, D. L.; Kung, H. F. Characterization of IMPY as a Potential Imaging Agent for β-Amyloid Plaques in Double Transgenic PSAPP Mice Eur. J. Nucl. Med. Mol. Imaging 2004, 31, 1136-1145
26. Stephenson, K. A.; Chandra, R.; Zhuang, Z. P.; Hou, C.; Oya, S.; Kung, M. P.; Kung, H. F. Fluoro-Pegylated (FPEG) Imaging Agents Targeting Aβ Aggregates Bioconjugate Chem. 2007, 18, 238-246
27. Hsiao, K.; Chapman, P.; Nilsen, S.; Eckman, C.; Harigaya, Y.; Younkin, S.; Yang, F.; Cole, G. Correlative Memory Deficits, Aβ Elevation, and Amyloid Plaques in Transgenic Mice Science 1996, 274, 99-102