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id="jr-fip-info-p"><a id="jr-fip-prev" class="wsprkl btn" title="Jump to previuos match">◀</a><button id="jr-fip-matches">no matches yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK23474_"><span class="title" itemprop="name">6-Iodo-2-[4'-<i>N</i>-(2-[<sup>18</sup>F]fluoroethyl)methylamino]phenylimidazo[1,2-<i>a</i>]pyridine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>18</sup>F]FEM-IMPY</div><p class="contribs">The MICAD Research Team.</p><p class="fm-aai"><a href="#_NBK23474_pubdet_">Publication Details</a></p></div></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figFEMIMPY18FT1"><a href="/books/NBK23474/table/FEMIMPY18F.T1/?report=objectonly" target="object" title="Table" class="img_link icnblk_img" rid-ob="figobFEMIMPY18FT1"><img class="small-thumb" src="/corehtml/pmc/css/bookshelf/2.26/img/table-icon.gif" alt="Table Icon" /></a><div class="icnblk_cntnt"><h4 id="FEMIMPY18F.T1"><a href="/books/NBK23474/table/FEMIMPY18F.T1/?report=objectonly" target="object" rid-ob="figobFEMIMPY18FT1">Table</a></h4><p class="float-caption no_bottom_margin">
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<i>In vitro</i>
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Rodents
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</p></div></div><div id="FEMIMPY18F.Background"><h2 id="_FEMIMPY18F_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%226-iodo-2-%284%27-N-%282-fluoroethyl%29methylamino%29phenylimidazo%281%2C2-a%29pyridine%22%5BSubstance%20Name%5D%20OR%20FEM-IMPY%5BText%20Word%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Alzheimer’s disease (AD) is a major neurodegenerative disease associated with an irreversible decline of mental functions and with cognitive impairment (<a class="bibr" href="#FEMIMPY18F.EXTYLES.1" rid="FEMIMPY18F.EXTYLES.1">1</a>). It is characterized by the presence in the brain of senile plaques of β-amyloid (Aβ) peptides with intracellular neurofibrillary tangles of filaments that contain the hyperphosphorylated protein tau (<a class="bibr" href="#FEMIMPY18F.EXTYLES.2" rid="FEMIMPY18F.EXTYLES.2">2</a>, <a class="bibr" href="#FEMIMPY18F.EXTYLES.3" rid="FEMIMPY18F.EXTYLES.3">3</a>). Accelerated deposition of Aβ deposits seems to be a key risk factor associated with AD, and although the mechanisms of the disease are still not fully understood, reducing the deposition of amyloid plaques seems to benefit patients.</p><p>Several radioligands for positron emission tomography (PET) have been developed (<a href="#FEMIMPY18F.EXTYLES.4">4-6</a>) and tested in humans as <i>in vivo</i> diagnostic tools for imaging and measuring the formation of Aβ deposits (<a class="bibr" href="#FEMIMPY18F.EXTYLES.6" rid="FEMIMPY18F.EXTYLES.6">6</a>). The first agent successfully used in human studies was <a href="/books/n/micad/FDDNP18F/?report=reader">[<sup>18</sup>F]FDDNP</a> (<a class="bibr" href="#FEMIMPY18F.EXTYLES.7" rid="FEMIMPY18F.EXTYLES.7">7</a>), a malonitrile derivative found to bind to both neurofibrillary tangles and Aβ plaques. The second successful attempt was made with <a href="/books/n/micad/PIB11C/?report=reader">[<sup>11</sup>C]PIB</a> (<a class="bibr" href="#FEMIMPY18F.EXTYLES.8" rid="FEMIMPY18F.EXTYLES.8">8</a>), also known as Pittsburgh Compound B or [<sup>11</sup>C]6-OH-BTA-1, which showed marked retention in areas of the cortex known to contain substantial amounts of Aβ deposits. The third PET radioligand successfully tested in humans was [<sup>11</sup>C]4-<i>N</i>-methylamino-4´-hydroxystilbene, a stilbene derivative commonly named <a href="/books/n/micad/SB1311C/?report=reader">[<sup>11</sup>C]SB-13</a> that exhibited good binding affinities for Aβ aggregates <i>in vitro</i>, moderate lipophilicity, high initial brain uptake in the normal rat cortex, and a rapid washout (<a class="bibr" href="#FEMIMPY18F.EXTYLES.9" rid="FEMIMPY18F.EXTYLES.9">9</a>).</p><p>Benzofuran derivatives labeled with radioactive iodine have shown very good binding affinities for Aβ aggregates and good brain penetration (<a class="bibr" href="#FEMIMPY18F.EXTYLES.10" rid="FEMIMPY18F.EXTYLES.10">10</a>). Unfortunately, their level of nonspecific binding was found to be very high, which makes them unsuitable for <i>in vivo</i> plaque imaging. However, <a href="/books/n/micad/IMPY/?report=reader">[<sup>125</sup>I]IMPY</a> displayed a good initial brain uptake and rapid washout from normal mouse brain and postmortem AD brain sections (<a class="bibr" href="#FEMIMPY18F.EXTYLES.11" rid="FEMIMPY18F.EXTYLES.11">11</a>). Its desirable pharmacokinetics makes [<sup>125</sup>I]IMPY an attractive agent for mapping Aβ plaques. More recently, the <sup>18</sup>F-labeled analog of IMPY in which the <i>N</i>-methyl group is replaced with [<sup>18</sup>F]2-fluoroethyl ([<sup>18</sup>F]FEM-IMPY) has been synthesized and is currently under investigation as a prospective PET radioligand for Aβ plaques (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>).</p></div><div id="FEMIMPY18F.Synthesis"><h2 id="_FEMIMPY18F_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FEM-IMPY%20AND%20synthesis%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>A one-pot radiosynthesis of [<sup>18</sup>F]FEM-IMPY using HM-IMPY as the precursor was developed by Cai et al. (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>). In this method, HM-IMPY reacted with ethyleneglycol bis-tosylate at 130–150°C under microwave conditions. This slow reaction (5% complete after 10 min) could be enhanced by the addition of [K-(Kryptofix 222)]<sup>+</sup>[F]<sup>–</sup>, which accelerated the alkylation to generate FEM-IMPY with a 70–80% yield under anhydrous conditions. At the end of the synthesis, the radiochemical purity of the radiotracer was >93% and its specific radioactivity was 85–662 GBq/µmol (2.3–17.9 Ci/µmol).</p><p>The synthesis of the precursor HM-IMPY could be achieved in one step under mild conditions by bromination of the secondary amine 4-methylaminocetaphenone using tetra<i>-n</i>-butylammonium tribromide in MeOH (<a class="bibr" href="#FEMIMPY18F.EXTYLES.13" rid="FEMIMPY18F.EXTYLES.13">13</a>). This bromination was regioselective (only on the methyl group) and did not produce any byproducts on the ring from bromination.</p><p>An alternative synthesis of HM-IMPY is to follow one of the methods reported in the literature for the demethylation of <i>N,N</i>-dimethylanilines to perform a monodemethylation of the imidazopyridine IMPY (<a class="bibr" href="#FEMIMPY18F.EXTYLES.14" rid="FEMIMPY18F.EXTYLES.14">14</a>). One of the approaches used TiCl<sub>4</sub>/CH<sub>2</sub>Cl<sub>2</sub> and only produced polymerized compounds (<a class="bibr" href="#FEMIMPY18F.EXTYLES.15" rid="FEMIMPY18F.EXTYLES.15">15</a>). In the other approach, tetra<i>-n</i>-butylammonium periodate, a potent oxygen donor, was used to hydroxylate one of the methyl groups in the presence of a metalloporphyrin catalyst. Those two methods were not very successful: the first produced polymerized products only and the second led to low yields with many side reactions and had to be abandoned.</p></div><div id="FEMIMPY18F.In_Vitro_Studies_Tes"><h2 id="_FEMIMPY18F_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FEM-IMPY%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>FEM-IMPY was found to compete well with [<sup>125</sup>I]TZDM, a probe selective for Aβ plaques previously reported in the literature (<a class="bibr" href="#FEMIMPY18F.EXTYLES.16" rid="FEMIMPY18F.EXTYLES.16">16</a>). Studies of binding to Aβ-40 aggregates in solution and AD brain homogenates led to an inhibition constant (<i>K</i><sub>i</sub>) of 27 ± 8 nM. The high lipophilicity (Log D value of 4.41 ± 0.10 at pH 7.4) of FEM-IMPY might explain the relatively high nonspecific binding of [<sup>18</sup>F]FEM-IMPY to human AD brain homogenates (~50% of the total binding) (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>).</p><p>Incubation of mouse brain homogenates with [<sup>18</sup>F]FEM-IMPY at 37°C for various lengths of time resulted in radioactive polar and lipophilic metabolites and parent [<sup>18</sup>F]FEM-IMPY (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>). A mass spectrum analysis of the metabolites showed the presence of a dealkylated aromatic amino group, consistent with the fact that tertiary amino groups are unstable in an oxidative environment. Complete N-dealkylation of [<sup>18</sup>F]FEM-IMPY was not observed <i>in vitro</i>; the metabolism ended after the radioligand was degraded to ~10% conversion.</p></div><div id="FEMIMPY18F.Animal_Studies"><h2 id="_FEMIMPY18F_Animal_Studies_">Animal Studies</h2><div id="FEMIMPY18F.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FEM-IMPY%20AND%20rodentia%5BMeSH%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Cai et al. (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>) performed <i>in vivo</i> biodistribution studies on 4 normal male ICR mice (2–3 months-old) injected intravenously with a saline solution of [<sup>18</sup>F]FEM-IMPY [14.8–16.5 MBq (0.4–0.5 mCi)]. Results showed that the radiotracer easily penetrated the blood–brain barrier, and a peak of the brain uptake [~6.4% injected dose/g (% ID/g)] was observed at 0.5 min after injection. This value compared well with [<sup>123,125</sup>I]IMPY (7.2% ID/g in 2 min). However, the washout of radioactivity for [<sup>18</sup>F]FEM-IMPY in normal mice was found to be biphasic (rapid over the first 20 min and much slower thereafter), whereas a single-exponential washout was observed for [<sup>123,125</sup>I]IMPY. Residual brain radioactivity was 4.5% ID/g for [<sup>18</sup>F]FEM-IMPY at 2 h after injection.</p><p>A high-performance liquid chromatography analysis of homogenates of <i>ex vivo</i> mouse brain after injection of the radioligand showed that the residual activity represented polar metabolites (presumably a fluoride ion or a related small-molecule ionic species such as [<sup>18</sup>F]FCH<sub>2</sub>CO<sub>2</sub><sup>–</sup>) and was not the result of nonspecific binding. Lipophilicity of the ligands did not seem to play a role, and the contribution of the lipophilic intermediate was unclear at the time of the study. Given its low concentration observed both <i>in vivo</i> and <i>in vitro</i>, it might not have contributed significantly to the TACs.</p><p>Substantial bone uptake of [<sup>18</sup>F]FEM-IMPY was observed in the skull. Substitution of the 4-ethylene protons by deuterium led to a 34% reduction of the radioactivity in the skull, while there was no effect on brain uptake or clearance of the radiotracer.</p></div><div id="FEMIMPY18F.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FEM-IMPY%20AND%20%28dog%20OR%20sheep%20OR%20pig%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FEMIMPY18F.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FEM-IMPY%20AND%20%28%28primate%20NOT%20human%29%20OR%20baboon%20OR%20monkey%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Cai et al. (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>) performed brain PET scans on a male rhesus monkey (7.12 kg) after intravenous administration of 107.3 MBq (2.9 mCi) of [<sup>18</sup>F]FEM-IMPY. The experiment involved acquiring dynamic transaxial images over a period of 120 min with scan duration ranging from 30 s to 5 min.</p><p>Results showed a rapid increase of brain activity, with peak values of 0.26–0.35% ID/g at 3–6 min after injection. [<sup>18</sup>F]FEM-IMPY appeared to be washed out of all brain regions in a similar fashion, with a monoexponential washout rate of 0.05–0.09 min<sup>-1</sup> (0.0488 ± 0.0020 min<sup>-1</sup> for the brain stem, 0.0606 ± 0.0024 min<sup>-1</sup> for the frontal cortex, 0.0859 ± 0.0037 min<sup>-1</sup> for the striatum, and 0.0488 ± 0.0020 min<sup>-1</sup> for the cerebellum), which corresponds to a half-life (<i>t</i><sub>1/2</sub>) of 8–14 min. Activity in bone increased exponentially and reached levels of ~0.1% ID kg/g, which is similar to residual activity in the brain and substantially less than what was observed in mice. The studies by Cai et al. (<a class="bibr" href="#FEMIMPY18F.EXTYLES.12" rid="FEMIMPY18F.EXTYLES.12">12</a>) showed that the metabolism of [<sup>18</sup>F]FEM-IMPY was significantly slower in rhesus monkeys than in mice.</p></div></div><div id="FEMIMPY18F.Human_Studies"><h2 id="_FEMIMPY18F_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FEM-IMPY%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FEMIMPY18F.references"><h2 id="_FEMIMPY18F_references_">References</h2><dl class="temp-labeled-list"><dl class="bkr_refwrap"><dt>1.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.1">Forstl H. , Kurz A.
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Clinical features of Alzheimer's disease. <span><span class="ref-journal">Eur Arch Psychiatry Clin Neurosci. </span>1999;<span class="ref-vol">
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</span>(6):288–90.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10653284" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10653284</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>2.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.2">Hardy J.
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The relationship between amyloid and tau. <span><span class="ref-journal">J Mol Neurosci. </span>2003;<span class="ref-vol">
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</span>(2):203–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12794314" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12794314</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>3.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.3">Brandt R. , Leschik J.
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Functional interactions of tau and their relevance for Alzheimer's disease. <span><span class="ref-journal">Curr Alzheimer Res. </span>2004;<span class="ref-vol">
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</span>(4):255–69.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15975055" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15975055</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>4.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.4">Nordberg A.
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PET imaging of amyloid in Alzheimer's disease. <span><span class="ref-journal">Lancet Neurol. </span>2004;<span class="ref-vol">
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</span>(9):519–27.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15324720" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15324720</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>5.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.5">Bacskai B.J. , Hickey G.A. , Skoch J. , Kajdasz S.T. , Wang Y. , Huang G.F. , Mathis C.A. , Klunk W.E. , Hyman B.T.
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Four-dimensional multiphoton imaging of brain entry, amyloid binding, and clearance of an amyloid-beta ligand in transgenic mice. <span><span class="ref-journal">Proc Natl Acad Sci U S A. </span>2003;<span class="ref-vol">
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</span>(21):12462–7.</span> [<a href="/pmc/articles/PMC218780/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC218780</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/14517353" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14517353</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>6.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.6">Wu C. , Pike V.W. , Wang Y.
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Amyloid imaging: from benchtop to bedside. <span><span class="ref-journal">Curr Top Dev Biol. </span>2005;<span class="ref-vol">
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<strong>70</strong>
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</span>:171–213.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16338342" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16338342</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>7.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.7">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.
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Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease. <span><span class="ref-journal">Am J Geriatr Psychiatry. </span>2002;<span class="ref-vol">
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<strong>10</strong>
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</span>(1):24–35.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11790632" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11790632</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>8.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.8">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.
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Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. <span><span class="ref-journal">Ann Neurol. </span>2004;<span class="ref-vol">
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</span>(3):306–19.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14991808" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14991808</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>9.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.9">Ono M. , Wilson A. , Nobrega J. , Westaway D. , Verhoeff P. , Zhuang Z.P. , Kung M.P. , Kung H.F.
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11C-labeled stilbene derivatives as Abeta-aggregate-specific PET imaging agents for Alzheimer's disease. <span><span class="ref-journal">Nucl Med Biol. </span>2003;<span class="ref-vol">
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</span>(6):565–71.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12900282" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12900282</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>10.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.10">Ono M. , Kung M.P. , Hou C. , Kung H.F.
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Benzofuran derivatives as Abeta-aggregate-specific imaging agents for Alzheimer's disease. <span><span class="ref-journal">Nucl Med Biol. </span>2002;<span class="ref-vol">
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<strong>29</strong>
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</span>(6):633–42.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12234587" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12234587</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>11.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.11">Kung M.P. , Hou C. , Zhuang Z.P. , Zhang B. , Skovronsky D. , Trojanowski J.Q. , Lee V.M. , Kung H.F.
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IMPY: an improved thioflavin-T derivative for in vivo labeling of beta-amyloid plaques. <span><span class="ref-journal">Brain Res. </span>2002;<span class="ref-vol">
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<strong>956</strong>
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</span>(2):202–10.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12445687" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12445687</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>12.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.12">Cai L. , Chin F.T. , Pike V.W. , Toyama H. , Liow J.S. , Zoghbi S.S. , Modell K. , Briard E. , Shetty H.U. , Sinclair K. , Donohue S. , Tipre D. , Kung M.P. , Dagostin C. , Widdowson D.A. , Green M. , Gao W. , Herman M.M. , Ichise M. , Innis R.B.
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Synthesis and evaluation of two 18F-labeled 6-iodo-2-(4'-N,N-dimethylamino)phenylimidazo[1,2-a]pyridine derivatives as prospective radioligands for beta-amyloid in Alzheimer's disease. <span><span class="ref-journal">J Med Chem. </span>2004;<span class="ref-vol">
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<strong>47</strong>
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</span>(9):2208–18.</span> [<a href="/pmc/articles/PMC4137392/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC4137392</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/15084119" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15084119</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>13.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.13">Kajigaeshi S. , Kakinami T. , Okamoto T. , Fujisaki S.
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Synthesis of bromoacetyl derivatives by use of tetrabutylammonium tribromide. <span><span class="ref-journal">Bull. Chem. Soc. Jpn. </span>1987;<span class="ref-vol">
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<strong>60</strong>
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</span>:1159–1160.</span></div></dd></dl><dl class="bkr_refwrap"><dt>14.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.14">Zhuang Z.P. , Kung M.P. , Wilson A. , Lee C.W. , Plossl K. , Hou C. , Holtzman D.M. , Kung H.F.
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Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting beta-amyloid plaques in the brain. <span><span class="ref-journal">J Med Chem. </span>2003;<span class="ref-vol">
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<strong>46</strong>
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</span>(2):237–43.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12519062" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12519062</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>15.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.15">Periasamy M. , Jayakumar K.N. , Bharathi P.
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Aryltitanium species through the reaction of N,N-dialkylarylamines with TiCl(4): oxidative coupling, N-dealkylation, and reaction with electrophiles. <span><span class="ref-journal">J Org Chem. </span>2000;<span class="ref-vol">
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<strong>65</strong>
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</span>(11):3548–50.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10843646" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10843646</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>16.</dt><dd><div class="bk_ref" id="FEMIMPY18F.EXTYLES.16">Zhuang Z.P. , Kung M.P. , Hou C. , Skovronsky D.M. , Gur T.L. , Plossl K. , Trojanowski J.Q. , Lee V.M. , Kung H.F.
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Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. <span><span class="ref-journal">J Med Chem. </span>2001;<span class="ref-vol">
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<strong>44</strong>
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</span>(12):1905–14.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11384236" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11384236</span></a>]</div></dd></dl></dl></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK23474_pubdet_">Publication Details</h2><h3>Author Information and Affiliations</h3><div class="contrib half_rhythm"><span itemprop="author">The MICAD Research Team</span></div><h3>Publication History</h3><p class="small">Created: <span itemprop="datePublished">December 13, 2006</span>; Last Update: <span itemprop="dateModified">December 31, 2006</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="http://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>The MICAD Research Team. 6-Iodo-2-[4'-N-(2-[18F]fluoroethyl)methylamino]phenylimidazo[1,2-a]pyridine. 2006 Dec 13 [Updated 2006 Dec 31]. 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></p></div><div class="small-screen-prev"><a href="/books/n/micad/FDF18F/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/micad/FDPN18F/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobFEMIMPY18FT1"><div id="FEMIMPY18F.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23474/table/FEMIMPY18F.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__FEMIMPY18F.T1_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;">6-Iodo-2-[4'-<i>N</i>-(2-[<sup>18</sup>F]fluoroethyl)methylamino]phenylimidazo[1,2-<i>a</i>]pyridine</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/24420955" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=24420955" alt="image 24420955 in the ncbi pubchem database" /></a>
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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]FEM-IMPY</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;"></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;">Compound</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;">Aggregates of ß-amyloid (Aß) peptides</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;">Acceptor binding</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:</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></ul>
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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" /> Rodents
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</div></li></ul>
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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" /> Non-human primates
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</div></li></ul>
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<br />
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure for additional information in <a href="http://pubchem.ncbi.nlm.nih.gov" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.</td></tr></tbody></table></div></div></article></div><div id="jr-scripts"><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/libs.min.js"> </script><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.min.js"> </script></div></div>
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