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<title>18F-Labeled fluoropegylated 6-fluoroethoxy-4'-dimethylaminoflavone, 6-(2-(2-fluoro-ethoxy)-ethoxy)-4'-dimethylaminoflavone, and 6-(2-(2-(2-fluoro-ethoxy)-ethoxy)ethoxy)-4'-dimethylaminoflavone - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<div class="pre-content"><div><div class="bk_prnt"><p class="small">NCBI Bookshelf. A service of the National Library of Medicine, National Institutes of Health.</p><p>Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. </p></div><div class="iconblock clearfix whole_rhythm no_top_margin bk_noprnt"><a class="img_link icnblk_img" title="Table of Contents Page" href="/books/n/micad/"><img class="source-thumb" src="/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" alt="Cover of Molecular Imaging and Contrast Agent Database (MICAD)" height="100px" width="80px" /></a><div class="icnblk_cntnt eight_col"><h2>Molecular Imaging and Contrast Agent Database (MICAD) [Internet].</h2><a data-jig="ncbitoggler" href="#__NBK82962_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK82962_dtls__"><div>Bethesda (MD): <a href="https://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>; 2004-2013.</div></div><div class="half_rhythm"><ul class="inline_list"><li style="margin-right:1em"><a class="bk_cntns" href="/books/n/micad/">Contents</a></li></ul></div><div class="bk_noprnt"><form method="get" action="/books/n/micad/" id="bk_srch"><div class="bk_search"><label for="bk_term" class="offscreen_noflow">Search term</label><input type="text" title="Search this book" id="bk_term" name="term" value="" data-jig="ncbiclearbutton" /> <input type="submit" class="jig-ncbibutton" value="Search this book" submit="false" style="padding: 0.1em 0.4em;" /></div></form></div></div><div class="icnblk_cntnt two_col"><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/micad/Exe9-3918F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/F18_3f/" title="Next page in this title">Next ></a></div></div></div></div></div>
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<div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><h1 id="_NBK82962_"><span class="title" itemprop="name"><sup>18</sup>F-Labeled fluoropegylated 6-fluoroethoxy-4'-dimethylaminoflavone, 6-(2-(2-fluoro-ethoxy)-ethoxy)-4'-dimethylaminoflavone, and 6-(2-(2-(2-fluoro-ethoxy)-ethoxy)ethoxy)-4'-dimethylaminoflavone</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>18</sup>F]8(a–c)</div><p class="contrib-group"><span itemprop="author">Liang Shan</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK82962_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK82962_ai__"><div class="contrib half_rhythm"><span itemprop="author">Liang Shan</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a></div></div><div class="small">Corresponding author.</div></div></div><p class="small">Created: <span itemprop="datePublished">November 30, 2011</span>; Last Update: <span itemprop="dateModified">December 28, 2011</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="F18-8a-c.T.nc_chemical_name18flabeled_fl" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK82962/table/F18-8a-c.T.nc_chemical_name18flabeled_fl/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__F18-8a-c.T.nc_chemical_name18flabeled_fl_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>18</sup>F-Labeled fluoropegylated 6-fluoroethoxy-4'-dimethylaminoflavone, 6-(2-(2-fluoro-ethoxy)-ethoxy)-4'-dimethylaminoflavone, and 6-(2-(2-(2-fluoro-ethoxy)-ethoxy)ethoxy)-4'-dimethylaminoflavone</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<span class="graphic"><img src="/books/NBK82962/bin/F188ac.jpg" alt="Image F188ac.jpg" /></span>
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</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]8(a–c)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Synonym:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]8a, [<sup>18</sup>F]8b, [<sup>18</sup>F]8c</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Compounds</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">β-amyloid (Aβ)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Accepters</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Positron emission tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal / contrast:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>18</sup>F</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Structure of [<sup>18</sup>F]8(a–c) by Ono et al. (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>).</td></tr></tbody></table></div></div><div id="F18-8a-c.Background"><h2 id="_F18-8a-c_Background_">Background</h2><p>[<a href="/pubmed/?term=molecular%20imaging%20and%20Alzheimer%u2019s%20disease%20and%20%u03B2-amyloid%20" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><sup>18</sup>F-Labeled fluoropegylated 6-fluoroethoxy-4'-dimethylaminoflavone (compound 8a), 6-(2-(2-fluoro-ethoxy)-ethoxy)-4'-dimethylaminoflavone (compound 8b), and 6-(2-(2-(2-fluoro-ethoxy)-ethoxy)ethoxy)-4'-dimethylaminoflavone (compound 8c), abbreviated as [<sup>18</sup>F]8a, [<sup>18</sup>F]8b, and [<sup>18</sup>F]8c, respectively, are flavone derivatives synthesized by Ono et al. for positron emission tomography (PET) of Alzheimer’s disease (AD) by targeting β-amyloid (Aβ) (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>).</p><p>AD is characterized in pathology by the presence of extracellular Aβ plaques, intraneuronal neurofibrillary tangles, and neuronal loss in the cerebral cortex (<a class="bk_pop" href="#F18-8a-c.REF.2" data-bk-pop-others="F18-8a-c.REF.3">2, 3</a>). Of them, Aβ deposit is the earliest neuropathological marker and is relatively specific to AD and closely related disorders. Aβ plaques are composed of abnormal paired helical filaments 5–10 nm in size. These filaments are largely made of insoluble Aβ peptides that are 40 or 42 amino acids in length (<a class="bk_pop" href="#F18-8a-c.REF.4">4</a>).</p><p>In recent years, molecular imaging by targeting the extracellular Aβ has been intensively investigated in attempts to detect early AD, assess Aβ content <i>in vivo</i>, determine the timing of anti-plaque therapy, and evaluate the therapeutic efficacy (<a class="bk_pop" href="#F18-8a-c.REF.4">4</a>). Radiolabeled Aβ40 peptides were tested first, but they showed poor penetration ability to cross the blood–brain barrier (BBB) (<a class="bk_pop" href="#F18-8a-c.REF.4">4</a>). Based on the fact that Aβ can be specifically stained <i>in vitro</i> with dyes of Congo red, chrysamine G, and thioflavin-T, an effort was made to develop imaging agents with these dyes. This effort, however, was in general unsuccessful because the bulky ionic groups of heteroatoms in these dyes prevent them from crossing the BBB (<a class="bk_pop" href="#F18-8a-c.REF.2">2</a>). Importantly, a large class of derivatives (e.g., aminonaphthalenes, benzothiazoles, stilbenes, and imidazopyridines) was synthesized with these dyes as templates (<a class="bk_pop" href="#F18-8a-c.REF.4">4</a>). Clinical and preclinical studies have shown that these derivatives not only possess a high binding affinity with Aβ plaques as their parent compounds, but also exhibit good penetration ability through the BBB and rapid washout from brain with low to no plaque deposits.</p><p>Ono et al. first synthesized a class of radioiodinated flavone derivatives that present a high binding affinity with Aβ plaques and good penetration ability through the BBB (<a class="bk_pop" href="#F18-8a-c.REF.5">5</a>). However, these flavone derivatives display poor clearance from the brain, which leads to a high brain background. The investigators then explored another class of flavonoids with aurone as the core structure (<a class="bk_pop" href="#F18-8a-c.REF.1" data-bk-pop-others="F18-8a-c.REF.6">1, 6</a>). Aurone is a heterocyclic chemical compound that contains a benzofuran element associated with a benzylidene linked in position 2 and a chalcone-like group being closed into a five-member ring. The aurone derivatives possess a nucleophilic group (NH<sub>2</sub>, NHMe, or NMe<sub>2</sub>) at the 4' position and a radioiodine at the 5 position. Although these aurone derivatives exhibit a strong binding affinity with Aβ (inhibition constant (<i>K</i><sub>i</sub>) = 1.2–6.8 nM), high penetration ability through the BBB (1.9%−4.6% injected dose per gram tissue (ID/g) at 2 min), and a fast washout from the brain (0.3%−0.5% ID/g at 30 min), the pharmacokinetics of these compounds are less favorable for brain imaging than the pharmacokinetics of the agent [<sup>123</sup>I]IMPY (6-iodo-2-(4'-dimethylamino)phenyl-imidazo[1,2]pyridine), which is the only SPECT agent to be tested in humans to date (<a class="bk_pop" href="#F18-8a-c.REF.7" data-bk-pop-others="F18-8a-c.REF.8 F18-8a-c.REF.9">7-9</a>). The investigators also modified the flavone and aurone derivatives by pegylating them with 1–3 units of ethylene glycol at the 4' position or by conjugating them with the chelating agent bis-amino-bis-thiol (BAT). Favorable pharmacokinetics for brain imaging was observed for the pegylated derivatives ([<sup>18</sup>F]8(a–c)) but not for the BAT-chelated derivatives ([<sup>99m</sup>Tc]BAT-FL and [<sup>99m</sup>Tc]BAT-AR) (<a class="bk_pop" href="#F18-8a-c.REF.1" data-bk-pop-others="F18-8a-c.REF.6">1, 6</a>).</p><p>This series of chapters summarizes the data obtained with flavone and aurone derivatives, including [<sup>125</sup>I]15, [<sup>125</sup>I]9, [<sup>125</sup>I]14, [<sup>125</sup>I]16, [<sup>125</sup>I]17, [<sup>99m</sup>Tc]BAT-FL, [<sup>99m</sup>Tc]BAT-AR, [<sup>18</sup>F]8(a–c), [<sup>125</sup>I]3, and [<sup>18</sup>F]3 (<a class="bk_pop" href="#F18-8a-c.REF.1" data-bk-pop-others="F18-8a-c.REF.6 F18-8a-c.REF.7 F18-8a-c.REF.8">1, 6-8</a>). This chapter presents the data obtained with [<sup>18</sup>F]8(a–c) (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>).</p><div id="F18-8a-c.Related_Resource_Links"><h3>Related Resource Links:</h3><ul><li class="half_rhythm"><div>
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<a href="/books/?term=amyloid+AND+micad%5bbook%5d&view=chapter&p%24a=&p%24l=PBooksLayout&p%24st=books" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amyloid-targeted imaging agents in MICAD</a>
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</div></li><li class="half_rhythm"><div>
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<a href="http://clinicaltrials.gov/ct2/results?term=amyloid" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amyloid-targeted imaging clinical trials in ClinicalTrials.gov</a>
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</div></li><li class="half_rhythm"><div>
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<a href="/pcsubstance/?term=amyloid" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Structures and other information of amyloid peptides in PubChem</a>
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</div></li><li class="half_rhythm"><div>
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<a href="/omim/?term=Alzheimer%27s%20disease" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Alzheimer’s disease articles in Online Mendelian Inheritance in Man</a>
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||
</div></li></ul></div></div><div id="F18-8a-c.Synthesis"><h2 id="_F18-8a-c_Synthesis_">Synthesis</h2><p>[<a href="/pubmed/?term=19201614" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The synthesis of the compound precursors with chemical yields was described in detail by Ono et al. (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>). [<sup>18</sup>F]8(a–c) was obtained with the reaction of the corresponding tosylate precursors with [<sup>18</sup>F]fluoride. The reaction mixture was purified with reversed phase high-performance liquid chromatography. The radiochemical purities of the final products were >99%; radiochemical yields ranged from 5% to 13%; total synthesis times were 70 min; and specific activities were 33.3–55.5 GBq/mmol (900–1,500 mCi/mmol) at the end of synthesis.</p><p>[<sup>125</sup>I]6-Iodo-4'-dimethylaminoflavone ([<sup>125</sup>I]DMFV, <i>K</i><sub>d</sub> = 12.3 nM) was prepared as the radioligand in binding assays using the standard iododestannylation reaction (<a class="bk_pop" href="#F18-8a-c.REF.10">10</a>). The specific activity and radiochemical purity of [<sup>125</sup>I]DMFV were 81.4 TBq/mmol (2.2 kCi/mmol) and >95%, respectively.</p></div><div id="F18-8a-c.In_Vitro_Studies_Testing_in_Cel"><h2 id="_F18-8a-c_In_Vitro_Studies_Testing_in_Cel_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed/?term=19201614" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The binding of [<sup>18</sup>F]8(a–c) with Aβ aggregates was carried out with [<sup>125</sup>I]DMFV in solutions (<a class="bk_pop" href="#F18-8a-c.REF.1" data-bk-pop-others="F18-8a-c.REF.10">1, 10</a>). The <i>K</i><sub>i</sub> values were measured to be 5.3, 14.4, and 19.3 for [<sup>18</sup>F]8a, [<sup>18</sup>F]8b, and [<sup>18</sup>F]8c, respectively. The results of <i>K</i><sub>i</sub> measurement for [<sup>18</sup>F]8(a–c) and other derivatives indicate that the affinities of flavone derivatives for Aβ(1–42) aggregates were affected by the group substituted at the 4' position in the flavone structure, not by the length of ethylene glycol introduced into the flavone backbone (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>).</p><p>The affinity of [<sup>18</sup>F]8(a–c) for brain Aβ plaques was analyzed with brain sections of <i>Tg2576</i> transgenic mice with fluorescence staining (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>). Many fluorescent spots were observed, and these findings were consistent with those obtained with immunohistochemical labeling with an antibody specific for Aβ. No spots were observed in the brain sections of wild-type mice (data not shown). These results indicate that [<sup>18</sup>F]8(a–c) can bind specifically with Aβ plaques in the mouse brain.</p></div><div id="F18-8a-c.Animal_Studies"><h2 id="_F18-8a-c_Animal_Studies_">Animal Studies</h2><div id="F18-8a-c.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed/?term=19201614" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of [<sup>18</sup>F]8(a–c) was examined in normal mice (<i>n</i> = 4–5/time point for each agent) (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>). All three ligands displayed high radioactivity in the brain at 2 min after injection (2.89%–4.17% ID/g). Low radioactivity was observed at 30 min after injection (1.89%, 2.00%, and 1.31% ID/g for [<sup>18</sup>F]8a, [<sup>18</sup>F]8b, and [<sup>18</sup>F]8c, respectively). These values were equal to 45.3%, 56.5%, and 45.3% of the initial uptake peak for [<sup>18</sup>F]8a, [<sup>18</sup>F]8b, and [<sup>18</sup>F]8c, respectively, indicating a rapid initial uptake in normal brain tissue coupled with a fast washout, which is highly desirable for Aβ imaging. [<sup>18</sup>F]8(a–c) also showed high bone uptake (3.74%–6.21% ID/g) at 60 min after injection, suggesting there may be <i>in vivo</i> defluorination. However, the interference from this free fluoride is expected to be relatively low for brain imaging because the free fluorine was not taken up by brain tissue (<a class="bk_pop" href="#F18-8a-c.REF.1">1</a>).</p></div><div id="F18-8a-c.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28dog%20OR%20rabbit%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="F18-8a-c.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="F18-8a-c.Human_Studies"><h2 id="_F18-8a-c_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="F18-8a-c.References"><h2 id="_F18-8a-c_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.1">Ono M., Watanabe R., Kawashima H., Kawai T., Watanabe H., Haratake M., Saji H., Nakayama M.
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<em>18F-labeled flavones for in vivo imaging of beta-amyloid plaques in Alzheimer's brains.</em>
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<span><span class="ref-journal">Bioorg Med Chem. </span>2009;<span class="ref-vol">17</span>(5):2069–76.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19201614" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19201614</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.2">Ono M.
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<em>Development of positron-emission tomography/single-photon emission computed tomography imaging probes for in vivo detection of beta-amyloid plaques in Alzheimer's brains.</em>
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||
<span><span class="ref-journal">Chem Pharm Bull (Tokyo). </span>2009;<span class="ref-vol">57</span>(10):1029–39.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19801854" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19801854</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.3">Mathis C.A., Wang Y., Klunk W.E.
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<em>Imaging beta-amyloid plaques and neurofibrillary tangles in the aging human brain.</em>
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||
<span><span class="ref-journal">Curr Pharm Des. </span>2004;<span class="ref-vol">10</span>(13):1469–92.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15134570" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15134570</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.4">Vallabhajosula S.
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<em>Positron emission tomography radiopharmaceuticals for imaging brain Beta-amyloid.</em>
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||
<span><span class="ref-journal">Semin Nucl Med. </span>2011;<span class="ref-vol">41</span>(4):283–99.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21624562" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21624562</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.5">Ono M., Maya Y., Haratake M., Ito K., Mori H., Nakayama M.
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<em>Aurones serve as probes of beta-amyloid plaques in Alzheimer's disease.</em>
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<span><span class="ref-journal">Biochem Biophys Res Commun. </span>2007;<span class="ref-vol">361</span>(1):116–21.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17644062" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17644062</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.6">Ono M., Ikeoka R., Watanabe H., Kimura H., Fuchigami T., Haratake M., Saji H., Nakayama M.
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<em>99mTc/Re complexes based on flavone and aurone as SPECT probes for imaging cerebral beta-amyloid plaques.</em>
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<span><span class="ref-journal">Bioorg Med Chem Lett. </span>2010;<span class="ref-vol">20</span>(19):5743–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/20797860" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20797860</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.7">Maya Y., Ono M., Watanabe H., Haratake M., Saji H., Nakayama M.
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<em>Novel radioiodinated aurones as probes for SPECT imaging of beta-amyloid plaques in the brain.</em>
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<span><span class="ref-journal">Bioconjug Chem. </span>2009;<span class="ref-vol">20</span>(1):95–101.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19072219" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19072219</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.8">Watanabe H., Ono M., Kimura H., Kagawa S., Nishii R., Fuchigami T., Haratake M., Nakayama M., Saji H.
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<em>A dual fluorinated and iodinated radiotracer for PET and SPECT imaging of beta-amyloid plaques in the brain.</em>
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<span><span class="ref-journal">Bioorg Med Chem Lett. </span>2011;<span class="ref-vol">21</span>(21):6519–22.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21920750" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21920750</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.9">Newberg A.B., Wintering N.A., Plossl K., Hochold J., Stabin M.G., Watson M., Skovronsky D., Clark C.M., Kung M.P., Kung H.F.
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<em>Safety, biodistribution, and dosimetry of 123I-IMPY: a novel amyloid plaque-imaging agent for the diagnosis of Alzheimer's disease.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2006;<span class="ref-vol">47</span>(5):748–54.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16644743" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16644743</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="F18-8a-c.REF.10">Ono M., Yoshida N., Ishibashi K., Haratake M., Arano Y., Mori H., Nakayama M.
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<em>Radioiodinated flavones for in vivo imaging of beta-amyloid plaques in the brain.</em>
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<span><span class="ref-journal">J Med Chem. </span>2005;<span class="ref-vol">48</span>(23):7253–60.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16279784" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16279784</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></div></div></div>
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<div class="post-content"><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div><div class="small"><span class="label">Bookshelf ID: NBK82962</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/22220313" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">22220313</a></span></div><div style="margin-top:2em" class="bk_noprnt"><a class="bk_cntns" href="/books/n/micad/">Contents</a><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/micad/Exe9-3918F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/F18_3f/" title="Next page in this title">Next ></a></div></div></div></div>
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<div xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Views</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PDF_download" id="Shutter"></a></div><div class="portlet_content"><ul xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="simple-list"><li><a href="/books/NBK82962/?report=reader">PubReader</a></li><li><a href="/books/NBK82962/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK82962" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK82962" style="display:none" title="Cite this Page"><div class="bk_tt">Shan L. 18F-Labeled fluoropegylated 6-fluoroethoxy-4'-dimethylaminoflavone, 6-(2-(2-fluoro-ethoxy)-ethoxy)-4'-dimethylaminoflavone, and 6-(2-(2-(2-fluoro-ethoxy)-ethoxy)ethoxy)-4'-dimethylaminoflavone. 2011 Nov 30 [Updated 2011 Dec 28]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></div></div></li><li><a href="/books/NBK82962/pdf/Bookshelf_NBK82962.pdf">PDF version of this page</a> (164K)</li><li><a href="/books/n/micad/toc/bin/micad.csv">MICAD summary (CSV file)</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>In this page</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="page-toc" id="Shutter"></a></div><div class="portlet_content"><ul xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="simple-list"><li><a href="#F18-8a-c.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#F18-8a-c.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#F18-8a-c.In_Vitro_Studies_Testing_in_Cel" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#F18-8a-c.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#F18-8a-c.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#F18-8a-c.References" ref="log$=inpage&link_id=inpage">References</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Search MICAD</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="source-application" id="Shutter"></a></div><div class="portlet_content"><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmSearch" method="get" action="/books/NBK5330/" id="frmSearch"><script type="text/javascript" src="/corehtml/pmc//js/bookshelf/micad.js">/**/</script><label class="offscreen_noflow" for="txtfield">Search term</label><input id="txtfield" type="text" name="f1_term" size="22" onKeyPress="KeyPress('micad',event,'/books/NBK5330/','')" /><button name="f1_search" type="submit">Go</button><button onclick="this.form.reset();" type="reset">Clear</button><p><b>Limit my Search:</b></p><div class="clearfix"><label for="detection">Method of detection:</label><div class="right"><select name="detection" id="detection" style="width:200px"><option value="" selected="selected">Any</option><option value="(MRI OR "Magnetic resonance imaging" OR MRS)">MRI</option><option value="Multimodal">Multimodal imaging</option><option value="Optical">Optical imaging</option><option value="PET">PET</option><option value="Photoacoustic">Photoacoustic imaging</option><option value="(SPECT OR planar)">SPECT</option><option value="Ultrasound">Ultrasound</option><option value="(x-ray OR ct)">X-ray, CT</option></select></div></div><div class="clearfix"><label for="signal">Source of signal/contrast:</label><div class="right"><select name="signal" id="signal" style="width:200px"><option value="" selected="selected">Any</option><optgroup label="MRI agents"><option value="(Copper OR Cu)">Copper</option><option value="(Europium OR Eu3+)">Europium</option><option value="(Fluorine OR 19F)">Fluorine</option><option value="(Gadolinium OR Gd3+)">Gadolinium</option><option value=""Hyperpolarized 13C"">Hyperpolarized 13C</option><option value=""Iron oxide"">Iron oxide</option><option value=""Nitroxide radicals"">Nitroxide radicals</option><option value="(Oxygen OR 17O)">Oxygen</option><option value="Thulium">Thulium</option></optgroup><optgroup label="Multimodal agents"><option value="((Gadolinium OR Gd3+) AND Optical)">Gadolinium and optical</option><option value="((Gadolinium OR Gd3+) AND (Gold OR Au))">Gadolinium and Gold</option><option value="("Iron oxide" AND (64Cu OR 124I OR 111In))">Iron oxide and
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europium</option><option value="(166Ho OR 67Ga OR 68Ga OR 123I OR 124I OR 125I)">Radionuclides</option></optgroup><optgroup label="Optical agents"><option value="("Fluorescent dyes" OR protein)">Fluorescent dyes or proteins</option><option value=""Luminescent agents"">Luminescent agents</option><option value="(Metals OR Metal OR Gold OR Au)">Metals (Au)</option><option value="Nanotubes">Nanotubes</option><option value=""Quantum dots"">Quantum dots</option></optgroup><optgroup label="PET radionuclides"><option value="("Arsenic 74" OR 74As)">Arsenic-74</option><option value="("Bromine 76" OR 76Br)">Bromine-76</option><option value="("Carbon 11" OR 11C)">Carbon-11</option><option value="(Copper-60 OR Copper-61 OR Copper-62 OR Copper-64 OR 60Cu OR 61Cu OR 62Cu OR 64Cu)">Copper-60, 61, 62, 64</option><option value="("Fluorine 18" OR 18F)">Fluorine-18</option><option value="(Gallium-68 OR 68Ga)">Gallium-68</option><option value="("Iodine 124" OR 124I)">Iodine-124</option><option 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value="Nanobubbles">Nanobubbles</option></optgroup><optgroup label="X-ray and CT agents"><option value="(Bismuth OR Bi)">Bismuth</option><option value="(Gold OR Au)">Gold</option><option value="Iodine">Iodine</option></optgroup></select></div></div><div class="clearfix"><label for="agent">Agent Category:</label><div class="right"><select name="agent" id="agent" style="width:200px"><option value="" selected="selected">Any</option><option value="(antibody OR trastuzumab OR immunoglobulin)">Antibodies</option><option value="(bacteria OR bacteriophage OR coli)">Bacteria</option><option value="cell">Cells</option><option value="(compound OR "amino acid" OR "folic acid" OR "cage molecule" OR carbohydrate OR copolymers OR polymer OR "small molecule" OR macromolecule OR triiodobenzoate OR estradiol OR glycosaminoglycan)">Compounds</option><option value="ligand">Ligands</option><option value="(lipid OR liposome OR liposomes">Lipids</option><option value="metal">Metal</option><option value="(nanoparticle OR nanoparticles OR nanotubes OR "iron oxide")">Nanoparticles</option><option value="(siRNA OR "nucleic acid" OR oligonucleotide)">Nucleic acids</option><option value="peptide">Peptides</option><option value="polyeptide">Polyeptides</option><option value="(protein OR albumin OR chemokin OR immunoprotein OR luciferase OR albumin)">Proteins</option><option value="(virus OR adenovirus)">Viruses</option></select></div></div><div class="clearfix"><label for="target">Target Category:</label><div class="right"><select name="target" id="target" style="width:200px"><option value="" selected="selected">Any</option><option value="acceptor">Acceptors</option><option value=""adhesion molecule"">Adhesion molecules</option><option value="(antigen OR antibody-antigen)">Antigens</option><option value="(enzyme OR enzymes OR enzyme-substrate)">Enzymes</option><option value="(lipids OR lipophilic cation)">Lipids</option><option value="(receptor OR receptors OR receptor-ligand OR receptor-antibody OR antibody-receptor)">Receptors</option><option value="transporter">Transporters</option><option value="non-targeted">Non-targeted</option><option value=""nucleic acid"">Nucleic acids</option><option value="(non-targeted OR "unknown binding site")">Others</option></select></div></div><div><input id="__micad_btn_1" type="radio" name="stage" value="vitro" /><label for="__micad_btn_1"><i>In vitro</i></label><input id="__micad_btn_2" type="radio" name="stage" value="rodents" /><label for="__micad_btn_2">Rodents</label><input id="__micad_btn_3" type="radio" name="stage" value="mammals" /><label for="__micad_btn_3">Non-primate non-rodent mammals</label><br /><input id="__micad_btn_4" type="radio" name="stage" value="primates" /><label for="__micad_btn_4">Non-human primates</label><input id="__micad_btn_5" type="radio" name="stage" value="humans" /><label for="__micad_btn_5">Humans</label><input id="__micad_btn_6" type="radio" name="stage" value="any" checked="checked" /><label for="__micad_btn_6">Any</label></div></form><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmGo" method="get" action="javascript:alert('frmGo:_@action_was_not_set')" id="frmGo"><input name="term" value="." type="hidden" /></form></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Related information</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="discovery_db_links" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=2744244" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/22220317" ref="ordinalpos=1&linkpos=1&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Bis-amino-bis-thiol-conjugated 6-(3-bromopropoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one and (Z)-5-(3-bromopropoxy)-2-(4-(dimethylamino)benzylidene)benzofuran-3(2H)-one.</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> 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