Trifluoromethoxy-benzylated ligands improve amyloid detection in the brain using 19F magnetic resonance imaging

Neuroscience Research

Volumn 63, Issue 1, 2009, Pages 76-81

  Amatsubo, Tomone ^a,d   Morikawa, Shigehiro ^a   Inubushi, Toshio ^a   Urushitani, Makoto ^a   Taguchi, Hiroyasu ^a   Shirai, Nobuaki ^b   Hirao, Koichi ^b   Kato, Masanari ^c   Morino, Kyuya ^c   Kimura, Hirohiko ^c   Nakano, Ichiro ^c   Yoshida, Chikako ^c   Okada, Takashi ^c   Sano, Mitsuo ^c   Tooyama, Ikuo ^a  

^a SHIGA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

^b INDUSTRIAL RESEARCH CENTER OF SHIGA PREFECTURE   (Japan)

^c ISHIHARA SANGYO KAISHA LTD   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alzheimer's disease; Amyloid imaging; Brain; Fluorinated compounds; Magnetic resonance; Molecular imaging

Indexed keywords

2 (4' DIMETHYLAMINOSTYRYL) 6 [2 [(3' TRIFLUOROMETHOXY)BENZYLAMINO]ETHOXYETHOXY]BENZOXAZOLE; 2 (4' DIMETHYLAMINOSTYRYL) 6 [2 [(3' TRIFLUOROMETHOXY)BENZYLAMINO]ETHOXYETHOXYETHOXY]BENZOXAZOLE; AMYLOID; BENZOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD BRAIN BARRIER; BRAIN TISSUE; CONTROLLED STUDY; DRUG BINDING; DRUG PENETRATION; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE MICROSCOPY; FLUORINE NUCLEAR MAGNETIC RESONANCE; HYDROPHILICITY; HYDROPHOBICITY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; SENILE PLAQUE; TEMPORALIS MUSCLE;

ALZHEIMER DISEASE; AMYLOID; ANIMALS; BENZOXAZOLES; BLOOD-BRAIN BARRIER; BRAIN; FLUORINE COMPOUNDS; LIGANDS; MAGNETIC RESONANCE IMAGING; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; SENILE PLAQUES;

EID: 57649198094     PISSN: 01680102     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neures.2008.10.006     Document Type: Article

References (14)

1. Bouzide A., and Sauve G. Silver(I) oxide mediated highly selective monotosylation of symmetrical diols. Application to the synthesis of polysubstituted cyclic ethers. Org. Lett. 4 (2002) 2329-2332
2. Dzik-Jurasz A.S., Leach M.O., and Rowland I.J. Investigation of microenvironmental factors influencing the longitudinal relaxation times of drugs and other compounds. Magn. Reson. Imaging 22 (2004) 973-982
3. Flaherty D.P., Walsh S.M., Kiyota T., Dong Y., Ikezu T., and Vennerstrom J.L. Polyfluorinated bis-styrylbenzen β-amyloid plaque binding ligands. J. Med. Chem. 50 (2007) 4986-4992
4. Fujita S., Koyama K., and Inagaki Y. The Beckmann rearrangement by means of phosphoryl chloride/N,N-dimethylacetamide. A novel and convenient method of preparing benzoxazoles. Synthesis (1982) 68-69
5. Furumoto S., Okamura N., Iwata R., Yanai K., Arai H., and Kudo Y. Recent advances in the development of amyloid imaging agents. Curr. Top. Med. Chem. 7 (2007) 1773-1789
6. Hardy J.A., and Higgins G.A. Alzheimer's disease: the amyloid cascade hypothesis. Science 256 (1992) 184-185
7. Hardy J.A., and Selkoe D.J. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 297 (2002) 353-356
8. 1H MRI detection of amyloid beta plaques in vivo. Nat. Neurosci. 8 (2005) 527-533
9. Huddleston D.E., and Small S.A. Technology insight: imaging amyloid plaques in the living brain with positron emission tomography and MRI. Nat. Clin. Pract. Neurol. 1 (2005) 96-105
10. 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., and Langstrom B. Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. Ann. Neurol. 55 (2004) 306-319
11. Kudo Y., Okamura N., Furumoto S., Tashiro M., Furukawa K., Maruyama M., Itoh M., Iwata R., Yanai K., and 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. 48 (2007) 553-561
12. Shimadzu H., Suemoto T., Suzuki M., Shiomitsu T., Okamura N., Kudo Y., and Sawada T. Novel probes for imaging amyloid-β: F-18 and C-11 labeling of 2-(4-aminostyryl)benzoxazole derivatives. J. Labell. Comp. Radiopharm. 47 (2004) 181-190
13. 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., and Barrio J.R. Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease. Am. J. Geriatr. Psychiatry 10 (2002) 24-53
14. Thal L.J., Kantarci K., Reiman E.M., Klunk W.E., Weiner M.W., Zetterberg H., Galasko D., Pratico D., Griffin S., Schenk D., and Siemers E. The role of biomarkers in clinical trials for Alzheimer disease. Alzheimer Dis. Assoc. Disord. 20 (2006) 6-15