Molecular imaging of β-amyloid plaques with near-infrared boron dipyrromethane (BODIPY)-based fluorescent probes

Molecular Imaging

Volumn 12, Issue 5, 2013, Pages 338-347

  Watanabe, Hiroyuki ^a   Ono, Masahiro ^a   Matsumura, Kenji ^a   Yoshimura, Masashi ^a   Kimura, Hiroyuki ^a   Saji, Hideo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALZHEIMER DISEASE; FLUORESCENT PROBES; FLUORESCENT STAINING; NEAR-INFRARED FLUORESCENCE IMAGING; NEAR-INFRARED FLUORESCENT; NEURODEGENERATIVE; NON-SPECIFIC BINDING; SELECTIVE BINDING;

BORON; FLUORESCENCE; GLYCOPROTEINS; MAMMALS; MOLECULAR IMAGING;

INFRARED DEVICES;

4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; DIAGNOSTIC AGENT; FLUORESCENT DYE;

AMYLOID PLAQUE; ANIMAL; ARTICLE; BRAIN; FEMALE; FLUORESCENCE; KINETICS; METHODOLOGY; MOLECULAR IMAGING; MOUSE; NEAR INFRARED SPECTROSCOPY; PATHOLOGY; STAINING; TISSUE DISTRIBUTION; TRANSGENIC MOUSE; DIAGNOSTIC USE; PLAQUE, AMYLOID; PROCEDURES;

ANIMALS; BORON COMPOUNDS; BRAIN; FEMALE; FLUORESCENCE; FLUORESCENT DYES; KINETICS; MICE; MICE, TRANSGENIC; MOLECULAR IMAGING; PLAQUE, AMYLOID; SPECTROSCOPY, NEAR-INFRARED; STAINING AND LABELING; TISSUE DISTRIBUTION;

EID: 84879345111     PISSN: 15353508     EISSN: None     Source Type: Journal    
DOI: 10.2310/7290.2013.00049     Document Type: Article

References (43)

1. Klunk WE. Biological markers of Alzheimer's disease. Neurobiol Aging 1998;19:145-7, doi:10.1016/S0197-4580(98)00013-X. (Pubitemid 28167755)
2. Selkoe DJ. Imaging Alzheimer's amyloid. Nat Biotechnol 2000;18: 823-4, doi:10.1038/78422. (Pubitemid 30640902)
3. 18F-AZD4694, an amyloid-b-specific PET radioligand. J Nucl Med 2012;53:415-24, doi:10.2967/jnumed.111.094029.
4. Clark CM, Schneider JA, Bedell BJ, et al. Use of florbetapir-PET for imaging b-amyloid pathology. JAMA 2011;305:275-83, doi:10.1001/jama.2010.2008.
5. Jureus A, Swahn BM, Sandell J, et al. Characterization of AZD4694, a novel fluorinated Ab plaque neuroimaging PET radioligand. J Neurochem 2010;114:784-94, doi:10.1111/j.1471-4159.2010.06812.x.
6. 18F-AV-45: a PET agent for Ab plaques in the brain. J Nucl Med 2009; 50:1887-94, doi:10.2967/jnumed.109.065284.
7. 18F-BAY94-9172, a novel PET tracer: proof of mechanism Lancet Neurol 2008;7:129-35, doi:10.1016/S1474-4422(08)70001-2.
8. Zhang W, Oya S, Kung MP, et al. F-18 Polyethyleneglycol stilbenes as PET imaging agents targeting Ab aggregates in the brain. Nucl Med Biol 2005;32:799-809, doi:10.1016/j.nucmedbio.2005.06.001. (Pubitemid 41505313)
9. Klunk WE, Engler H, Nordberg A, et al. Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. Ann Neurol 2004;55:306-19, doi:10.1002/ana.20009. (Pubitemid 38269583)
10. 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem 2003;46:2740-54, doi:10.1021/jm030026b. (Pubitemid 36702542)
11. 123I-IMPY: a novel amyloid plaque-imaging agent for the diagnosis of Alzheimer's disease. J Nucl Med 2006;47:748-54. (Pubitemid 46768436)
12. Maya Y, Ono M, Watanabe H, et al. Novel radioiodinated aurones as probes for SPECT imaging of b-amyloid plaques in the brain. Bioconjug Chem 2009;20:95-101, doi:10.1021/bc8003292.
13. Cui M, Ono M, Kimura H, et al. Radioiodinated benzimidazole derivatives as single photon emission computed tomography probes for imaging of b-amyloid plaques in Alzheimer's disease. Nucl Med Biol 2011;38:313-20, doi:10.1016/j.nucmedbio.2010.09.012.
14. Kung MP, Hou C, Zhuang ZP, et al. IMPY: an improved thioflavin-T derivative for in vivo labeling of b-amyloid plaques. Brain Res 2002;956:202-10, doi:10.1016/S0006-8993(02)03436-4. (Pubitemid 35351385)
15. 1H MRI detection of amyloid b plaques in vivo. Nat Neurosci 2005;8:527-33, doi: 10.1038/nn1422. (Pubitemid 41007572)
16. 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques. Eur J Med Chem 2004;39:573-8, doi:10.1016/j.ejmech.2004.02.013. (Pubitemid 38962492)
17. 19F-containing curcumin derivative in a mouse model of Alzheimer's disease. Neuroscience 2011;184:120-7, doi:10.1016/j. neuroscience.2011.03.071.
18. Amatsubo T, Yanagisawa D, Morikawa S, et al. Amyloid imaging using high-field magnetic resonance. Magn Reson Med Sci 2010;9: 95-9, doi:10.2463/mrms.9.95.
19. Aslund A, Sigurdson CJ, Klingstedt T, et al. Novel pentameric thiophene derivatives for in vitro and in vivo optical imaging of a plethora of protein aggregates in cerebral amyloidoses. ACS Chem Biol 2009;4:673-84, doi:10.1021/cb900112v.
20. Chang WM, Dakanali M, Capule CC, et al. ANCA: a family of fluorescent probes that bind and stain amyloid plaques in human tissue. ACS Chem Neurosci 2011;2:249-55, doi:10.1021/cn200018v.
21. Hintersteiner M, Enz A, Frey P, et al. In vivo detection of amyloid-β deposits by near-infrared imaging using an oxazine-derivative probe. Nat Biotechnol 2005;23:577-83, doi:10.1038/nbt1085. (Pubitemid 41724896)
22. Nesterov EE, Skoch J, Hyman BT, et al. In vivo optical imaging of amyloid aggregates in brain: design of fluorescent markers. Angew Chem Int Ed Engl 2005;44:5452-6, doi:10.1002/anie.200500845. (Pubitemid 41273293)
23. Nilsson KP, Aslund A, Berg I, et al. Imaging distinct conformational states of amyloid-b fibrils in Alzheimer's disease using novel luminescent probes. ACS Chem Biol 2007;2:553-60, doi:10.1021/cb700116u. (Pubitemid 350011326)
24. Okamura N, Mori M, Furumoto S, et al. In vivo detection of amyloid plaques in the mouse brain using the near-infrared fluorescence probe THK-265. J Alzheimers Dis 2011;23:37-48.
25. Ran C, Moore A. Spectral unmixing imaging of wavelength-responsive fluorescent probes: an application for the real-time report of amyloid β species in Alzheimer's disease. Mol Imaging Biol 2011;14:293-300, doi:10.1007/s11307-011-0501-7.
26. Ran C, Xu X, Raymond SB, et al. Design, synthesis, and testing of difluoroboron-derivatized curcumins as near-infrared probes for in vivo detection of amyloid-β deposits. J Am Chem Soc 2009;131: 15257-61, doi:10.1021/ja9047043.
27. Ran C, Zhao W, Moir RD, et al. Non-conjugated small molecule FRET for differentiating monomers from higher molecular weight amyloid β species. PLoS One 2011;6:e19362, doi:10.1371/journal. pone.0019362.
28. Raymond SB, Skoch J, Hills ID, et al. Smart optical probes for near-infrared fluorescence imaging of Alzheimer's disease pathology. Eur J Nucl Med Mol Imaging 2008;35 Suppl 1:S93-8, doi:10.1007/s00259-007-0708-7.
29. Ono M, Hayashi S, Kimura H, et al. Push-pull benzothiazole derivatives as probes for detecting β-amyloid plaques in Alzheimer's brains. Bioorg Med Chem 2009;17:7002-7, doi:10. 1016/j.bmc.2009.08.032.
30. Ono M, Ishikawa M, Kimura H, et al. Development of dual functional SPECT/fluorescent probes for imaging cerebral β-amyloid plaques. Bioorg Med Chem Lett 2010;20:3885-8, doi:10. 1016/j.bmcl.2010.05.027.
31. Massoud TF, Gambhir SS. Molecular imaging in living subjects: seeing fundamental biological processes in a new light. Genes Dev 2003;17:545-80, doi:10.1101/gad.1047403. (Pubitemid 36307540)
32. Willmann JK, van Bruggen N, Dinkelborg LM, et al. Molecular imaging in drug development. Nat Rev Drug Discov 2008;7:591-607, doi:10.1038/nrd2290. (Pubitemid 351927724)
33. Weissleder R. A clearer vision for in vivo imaging. Nat Biotechnol 2001;19:316-7, doi:10.1038/86684.
34. Ojida A, Sakamoto T, Inoue MA, et al. Fluorescent BODIPY-based Zn(II) complex as a molecular probe for selective detection of neurofibrillary tangles in the brains of Alzheimer's disease patients. J Am Chem Soc 2009;131:6543-8, doi:10.1021/ja9008369.
35. Lee JS, Kang NY, Kim YK, et al. Synthesis of a BODIPY library and its application to the development of live cell glucagon imaging probe. J Am Chem Soc 2009;131:10077-82, doi:10. 1021/ja9011657.
36. Bozdemir OA, Erbas-Cakmak S, Ekiz OO, et al. Towards unimolecular luminescent solar concentrators: BODIPY-based dendritic energy-transfer cascade with panchromatic absorption and monochromatized emission. Angew Chem Int Ed Engl 2011; 50:10907-12, doi:10.1002/anie.201104846.
37. Komatsu T, Urano Y, Fujikawa Y, et al. Development of 2,6-carboxy-substituted boron dipyrromethene (BODIPY) as a novel scaffold of ratiometric fluorescent probes for live cell imaging. Chem Commun (Camb) 2009;45:7015-7, doi:10.1039/b917209b.
38. Ono M, Watanabe H, Kimura H, et al. BODIPY-based molecular probe for imaging of cerebral β-amyloid plaques. ACS Chem Neurosci 2012;3:319-24, doi:10.1021/cn3000058.
39. Cui M, Ono M, Kimura H, et al. Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for β-amyloid plaques. J Med Chem 2011;54:2225-40, doi:10.1021/jm101404k.
40. Ono M, Hori M, Haratake M, et al. Structure-activity relationship of chalcones and related derivatives as ligands for detecting of β-amyloid plaques in the brain. Bioorg Med Chem 2007;15:6388-96, doi:10.1016/j.bmc.2007. 06.055. (Pubitemid 47212733)
41. Cui MC, Li ZJ, Tang RK, et al. Synthesis and evaluation of novel benzothiazole derivatives based on the bithiophene structure as potential radiotracers for β-amyloid plaques in Alzheimer's disease. Bioorg Med Chem 2010;18:2777-84, doi:10.1016/j.bmc.2010.02.002.
42. Prim D, Kirsch G, Nicoud JF. Efficient synthesis of N,N-disubstituted 5-aminothiophene-2-carboxaldehydes by nucleophi-lic aromatic substitution in water. Synlett 1998;4:383-4, doi:10. 1055/s-1998-1657. (Pubitemid 128693799)
43. 18F-labeled benzofuran derivatives with improved properties for positron emission tomography (PET) imaging of β-amyloid plaques in Alzheimer's brains. J Med Chem 2011;54:2971-9, doi:10.1021/jm200057u.