Radioiodinated benzimidazole derivatives as single photon emission computed tomography probes for imaging of α-amyloid plaques in Alzheimer's disease

Nuclear Medicine and Biology

Volumn 38, Issue 3, 2011, Pages 313-320

  Cui, Mengchao ^a,b   Ono, Masahiro ^a   Kimura, Hiroyuki ^a   Kawashima, Hidekazu ^a   Liu, Bo Li ^b   Saji, Hideo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b BEIJING NORMAL UNIVERSITY   (China)

Author keywords

Amyloid; Alzheimer's disease; Imaging agent; Single photon emission computed tomography (SPECT)

Indexed keywords

4 (6 IODO 1H BENZO[D]IMIDAZOLE 2 YL) N METHYLANILINE; 4 (6 IODO 1H BENZO[D]IMIDAZOLE 2 YL) N,N DIMETHYLANILINE; 4 (6 IODO 1H BENZO[D]IMIDAZOLE 2 YL) N,N DIMETHYLANILINE I 125; 4 (6 IODO 1H BENZO[D]IMIDAZOLE 2 YL)ANILINE; 4 (6 IODO 1H BENZO[D]IMIDAZOLE 2 YL)PHENOL; 6 IODO 2 (4 METHOXYPHENYL) 1H BENZO[D]IMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; DIAGNOSTIC AGENT; IODINE 125; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

AGED; ALZHEIMER DISEASE; AMYLOID PLAQUE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG UPTAKE; FEMALE; HUMAN; HUMAN TISSUE; MALE; MOUSE; NONHUMAN; RADIOIODINATION; SIGNAL NOISE RATIO; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; TRANSGENIC MOUSE;

AGED; ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; BENZIMIDAZOLES; BRAIN; FEMALE; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IODINE RADIOISOTOPES; MALE; MICE; PLAQUE, AMYLOID; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON; YOUNG ADULT;

EID: 79954422352     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.09.012     Document Type: Article

References (28)

1. Hardy J.A., Higgins G.A. Alzheimer's disease: the amyloid cascade hypothesis. Science 1992, 256:184-185.
2. Selkoe D.J. The origins of Alzheimer disease: A is for amyloid. JAMA 2000, 283:1615-1617.
3. Hardy J.A., Selkoe D.J. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 2002, 297:353-356.
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. Cai L.S., Innis R.B., Pike V.W. Radioligand development for PET imaging of β-amyloid (Aβ)-current status. Curr Med Chem 2007, 14:19-52.
6. Klunk W.E., Engler H., Nordberg A., Wang Y., Blomqvist G., Holt D.P., et al. Imaging brain amyloid in Alzheimer's disease with Pittsburgh compound-B. Ann Neurol 2004, 55:306-319.
7. Mathis C.A., Wang Y., Holt D.P., Huang G.F., Debnath M.L., Klunk W.E. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem 2003, 46:2740-2754.
8. Verhoeff N.P., Wilson A.A., Takeshita S., Trop L., Hussey D., Singh K., et al. In vivo imaging of Alzheimer disease β-amyloid with [11C]SB-13 PET. Am J Geriatr Psychiatry 2004, 12:584-595.
9. Ono M., Wilson A., Nobrega J., Westaway D., Verhoeff P., Zhuang Z.P., et al. 11C-Labeled stilbene derivatives as Aβ-aggregate-specific PET imaging agents for Alzheimer's disease. Nucl Med Biol 2003, 30:565-571.
10. Kudo Y., Okamura N., Furumoto S., Tashiro M., Furukawa K., Maruyama M., et al. 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, 48:553-556.
11. Agdeppa E.D., Kepe V., Liu J., Flores-Torres S., Satyamurthy N., Petric A., et al. 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.
12. Shoghi-Jadid K., Small G.W., Agdeppa E.D., Kepe V., Ercoli L.M., Siddarth P., et al. 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.
13. Small G.W., Kepe V., Ercoli L.M., Siddarth P., Bookheimer S.Y., Miller K.J., et al. PET of brain amyloid and tau in mild cognitive impairment. N Engl J Med 2006, 355:2652-2663.
14. Rowe C.C., Ackerman U., Browne W., Mulligan R., Pike K.L., O'Keefe G., et al. Imaging of amyloid β in Alzheimer's disease with 18F-BAY94-9172, a novel PET tracer: proof of mechanism. Lancet Neurol 2008, 7:129-135.
15. Choi S.R., Golding G., Zhuang Z.P., Zhang W., Lim N., Hefti F., et al. Preclinical properties of 18F-AV-45: a PET agent for Aβ plaques in the brain. J Nucl Med 2009, 50:1887-1894.
16. Kung H.F., Choi S.R., Qu W.C., Zhang W., Skovronsky D. 18F Stilbenes and styrylpyridines for PET imaging of Aβ plaques in Alzheimer's disease: a miniperspective. J Med Chem 2010, 53:933-941.
17. Zhuang Z.P., Kung M.P., Hou C., Skovronsky D.M., Gur T.L., Plossl K., et al. Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. J Med Chem 2001, 44:1905-1914.
18. 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.
19. Zhuang Z.P., Kung M.P., Hou C., Plossl K., Skovronsky D., Gur T.L., et al. IBOX(2-(4'-dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain. Nucl Med Biol 2001, 28:887-894.
20. Qu W.C., Kung M.P., Hou C., Benedum T.E., Kung H.F. Novel styrylpyridines as probes for SPECT imaging of amyloid plaques. J Med Chem 2007, 50:2157-2165.
21. Kung M.P., Hou C., Zhuang Z.P., Zhang B., Skovronsky D., Trojanowski J.Q., et al. IMPY: an improved thioflavin-T derivative for in vivo labeling of beta-amyloid plaques. Brain Res 2002, 956:202-210.
22. Zhuang Z.P., Kung M.P., Wilson A., Lee C.W., Plossl K., Hou C., et al. Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting β-amyloid plaques in the brain. J Med Chem 2003, 46:237-243.
23. Newberg A.B., Wintering N.A., Plossl K., Hochold J., Stabin M.G., Watson M., et al. Safety, biodistribution, and dosimetry of 123I-IMPY: a novel amyloid plague-imaging agent for the diagnosis of Alzheimer's disease. J Nucl Med 2006, 47:748-754.
24. Cheng Y., Prusoff W. Biochem Pharmacol 1973, 1973:3099.
25. Maya Y., Ono M., Watanabe H., Haratake M., Saji H., Nakayama M. Novel radioiodinated aurones as probes for SPECT imaging of β-amyloid plaques in the brain. Bioconjugate Chem 2009, 20:95-101.
26. Wu C.Y., Wei J.J., Gao K.Q., Wang Y.M. Dibenzothiazoles as novel amyloid-imaging agents. Bioorg Med Chem 2007, 15:2789-2796.
27. Cai L.S., Cuevas J., Temme S., Herman M.M., Dagostin C., Widdowson D.A., et al. Synthesis and structure affinity relationships of new 4-(6-Iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine derivatives as ligands for human β-amyloid plaques. J Med Chem 2007, 50:4746-4758.
28. 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.