F-18 stilbenes as PET imaging agents for detecting β-amyloid plaques in the brain

Journal of Medicinal Chemistry

Volumn 48, Issue 19, 2005, Pages 5980-5988

  Zhang, Wei ^a   Oya, Shunichi ^a   Kung, Mei Ping ^a   Hou, Catherine ^a   Maier, Donna L ^b   Kung, Hank F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUOROMETHYL 3 [4 [2 (4 METHYLAMINOPHENYL)VINYL]PHENOXY]PROPAN 1 OL; 3 [4 [2 (4 DIMETHYLAMINOPHENYL)VINYL]PHENOXY] 2 FLUOROMETHYLPROPAN 1 OL; AMYLOID BETA PROTEIN; FLUORINE 18; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BRAIN HOMOGENATE; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DIAGNOSTIC VALUE; DRUG PENETRATION; FLUORINATION; IN VIVO STUDY; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY;

ALZHEIMER DISEASE; AMYLOID BETA-PROTEIN; ANIMALS; BRAIN; FLUORINE RADIOISOTOPES; HUMANS; MICE; MICE, INBRED ICR; MICE, TRANSGENIC; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 24944586305     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050166g     Document Type: Article

References (34)

1. 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.
2. Ginsberg, S. D.; Schmidt, M. L.; Crino, P. B.; Eberwine, J. H.; Lee, V. M.-Y.; Trojanowski, J. Q. Molecular pathology of Alzheimer's disease and related disorders. Cerebral cortex: neurodegenerative and age-related changes in structure and function of cerebral cortex; Kluwer Academic/Plenum: New York, 1999; pp 603-654.
3. Selkoe, D. J. Imaging Alzheimer's amyloid. Nature Biotechnol. 2000, 18, 823-824.
4. Wolfe, M. S. Therapeutic strategies for Alzheimer's disease. Nat. Rev. Drug Discovery 2002, 1, 859-866.
5. Bachurin, S. O. Medicinal chemistry approaches for the treatment and prevention of Alzheimer's disease. Med. Res. Rev. 2003, 23, 48-88.
6. Klunk, W. E.; Engler, H.; Nordberg, A.; Wang, Y.; Blomqvist, G.; Holt, D. P.; Bergstrom, M.; Savitcheva, I.; Huang, G.-f; Estrada, S.; Ausen, B.; Debnath, M. L.; Barletta, J.; Price, J. C.; Sandell, J.; Lopresti, B. J.; Wall, A.; Koivisto, P.; Antoni, G.; Mathis, C. A.; Langstrom, B. Imaging Brain Amyloid in Alzheimer's Disease with Pittsburgh Compound-B. Ann. Neurol. 2004, 55, 306-319.
7. Verhoeff, N. P.; Wilson, A. A.; Takeshita, S.; Trop, L.; Hussey, D.; Singh, K.; Kung, H. F.; Kung, M.-P.; Houle, S. In vivo imaging of Alzheimer disease beta-amyloid with [11C]SB-13 PET. Am. J. Geriatr. Psychiatry 2004, 12, 584-595.
8. Okamura, N.; Suemoto, T.; Shimadzu, H.; Suzuki, M.; Shiomitsu, T.; Akatsu, H.; Yamamoto, T.; Staufenbiel, M.; Yanai, K.; Arai, H.; Sasaki, H.; Kudo, Y.; Sawada, T. Styrylbenzoxazole derivatives for in vivo imaging of amyloid plaques in the brain. J. Neurosci. 2004, 24, 2535-2541.
9. 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.; Liu, J.; Flores-Torres, S.; Cole, G. M. Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease: Binding characteristics of radiofluorinated 6-dialkylamino-2-naphthyl- ethylidene derivatives as positron emission tomography imaging probes for beta-amyloid plaques in Alzheimer disease. Am. J. Geriatr. Psychiatry 2002, 10, 24-35.
10. Mathis, C. A.; Wang, Y.; Klunk, W. E. Imaging b-amyloid plaques and neurofibrillary tangles in the aging human brain. Curr. Pharm. Des. 2004, 10, 1469-1492.
11. 11C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents. J. Med. Chem. 2003, 46, 2740-2754.
12. Wang, Y.; Klunk, W. E.; Debnath, M. L.; Huang, G. F.; Holt, D. P.; Shao, L.; Mathis, C. A. Development of a PET/SPECT agent for amyloid imaging in Alzheimer's disease. J. Mol. Neurosci. 2004, 24, 55-62.
13. Agdeppa, E. D.; Kepe, V.; Liu, J.; Flores-Torres, S.; Satyamurthy, N.; Petric, A.; Cole, G. M.; Small, G. W.; Huang, S. C.; Barrio, J. R. Binding characteristics of radiofluorinated 6-dialkylamino-2-naphthylethylidene derivatives as positron emission tomography imaging probes for β-amyloid plaques in Alzheimer's disease. J. Neurosci. 2001, 21, RC189.
14. Nordberg, A. PET imaging of amyloid in Alzheimer's disease. Lancet Neurol. 2004, 3, 519-527.
15. 11C-Labeled Stilbene Derivatives as Aβ-aggregate-specific PET Imaging Agents for Alzheimer's Disease. Nucl. Med. Biol. 2003, 30, 565-571.
16. Zhuang, Z. P.; Kung, M. P.; Wilson, A.; Lee, C. W.; Plossl, K.; Hou, C.; Holtzman, D. M.; Kung, H. F. Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting beta-amyloid plaques in the brain. J. Med. Chem. 2003, 46, 237-243.
17. Kung, M. P.; Hou, C.; Zhuang, Z.-P.; Zhang, B.; Skovronsky, D. M.; Gur, T.; Lee, V. M.-Y.; Trojanowski, J. Q.; Kung, H. F. IMPY: An improved thioflavin-T derivative for in vivo Labeling of β-amyloid plaques. Brain Res. 2002, 956, 202-210.
18. 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. Imag. 2004, 31, 1136-1145.
19. 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, 89-105.
20. 18F-Labeled 6-Iodo-2-(4′-N,N-dimethylamino)phenylimidazo[1,2-a]pyridine Derivatives as Prospective Radioligands for β-Amyloid in Alzheimer's Disease. J. Med. Chem. 2004, 47, 2208-2218.
21. Lee, C.-W.; Kung, M.-P.; Hou, C.; Rung, H. F. Dimethylaminofluorenes: Ligands for Detecting β-Amyloid Plaques in the Brain. Nucl. Med. Biol. 2003, 30, 573-580.
22. Suemoto, T.; Okamura, N.; Shiomitsu, T.; Suzuki, M.; Shimadzu, H.; Akatsu, H.; Yamamoto, T.; Kudo, Y.; Sawada, T. In vivo labeling of amyloid with BF-108. Neurosci. Res. (Amsterdam) 2004, 48, 65-74.
23. Kung, H. F.; Lee, C.-W.; Zhuang, Z. P.; Kung, M. P.; Hou, C.; Plossl, K. Novel stilbenes as probes for amyloid plaques. J. Am. Chem. Soc. 2001, 123, 12740-12741.
24. 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.
25. Cox, D. P.; Terpinski, J.; Lawrynowicz, W. "Anhydrous" tetrabutylammonium fluoride: a mild but highly efficient source of nucleophilic fluoride ion. J. Org. Chem. 1984, 49, 3216-3219.
26. Miyashita, N.; Yoshikoshi, A.; Grieco, A. P. Pyridinium p-toluenesulfonate and efficient catalyst for the tetrahydropyranylation of alcohols. J. Org. Chem. 1977, 42, 3772-3774.
27. Musso, D. L.; Cochran, F. R.; Kelley, J. L.; McLean, E. W.; Selph, J. L. Indanylidenes.1. Design and Synthesis of (E)-2-(4,6-Difluoro-1-indanylidene) acetamide, a Potent, Centrally Acting Muscle Relaxant with Antiinflammatory and Analgesic Activity. J. Med. Chem. 2003, 46, 399-408.
28. McGowan, E.; Sanders, S.; Iwatsubo, T.; Takeuchi, A.; Saido, T.; Zehr, C.; Yu, X.; Uljon, S.; Wang, R.; Mann, D.; Dickson, D.; Duff, K. Amyloid phenotype characterization of transgenic mice overexpressing both mutant amyloid precursor protein and mutant presenilin 1 transgenes. Neurobiol. Dis. 1999, 6, 231-244.
29. Westerman, M. A.; Cooper-Blacketer, D.; Mariash, A.; Kotilinek, L.; Kawarabayashi, T.; Younkin, L. H.; Carlson, G. A.; Younkin, S. G.; Ashe, K. H. The relationship between Abeta and memory in the Tg2576 mouse model of Alzheimer's disease. J. Neurosci. 2002, 22, 1858-1867.
30. van Dooren, T.; Dewachter, I.; Borghgraef, P.; van Leuven, F. Transgenic mouse models for APP processing and Alzheimer's disease: early and late defects. Subcell Biochem. 2005, 38, 45-63.
31. 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.
32. Cleary, J. P.; Walsh, D. M.; Hofmeister, J. J.; Shankar, G. M.; Kuskowski, M. A.; Selkoe, D. J.; Ashe, K. H. Natural oligomers of the amyloid-beta protein specifically disrupt cognitive function. Nat. Neurosci. 2005, 8, 79-84.
33. Bitan, G.; Kirkitadze, M. D.; Lomakin, A.; Vollere, S. S.; Benedek, G. B.; Teplow, D. B. Amyloid beta -protein (Abeta) assembly: Abeta 40 and Abeta 42 oligomerize through distinct pathways. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 330-335.
34. Serpell, L. C.; Sunde, M.; Benson, M. D.; Tennent, G. A.; Pepys, M. B.; Fraser, P. E. The protofilament substructure of amyloid fibrils. J. Mol. Biol. 2000, 300, 1033-1039.