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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="#__NBK23464_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23464_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/EF5/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/F18-DCFPyL/" 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="_NBK23464_"><span class="title" itemprop="name">2-(2-Nitroimidazol-1<i>H</i>-yl)-(3-[<sup>18</sup>F]fluoropropyl)acetamide</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>18</sup>F]EF1</div><p class="contrib-group"><span itemprop="author">The MICAD Research Team</span>.</p><p class="small">Created: <span itemprop="datePublished">November 5, 2005</span>; Last Update: <span itemprop="dateModified">November 17, 2005</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="EF-mono.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23464/table/EF-mono.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__EF-mono.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>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">2-(2-Nitroimidazol-1<i>H</i>-yl)-<i>N</i>-(3-[<sup>18</sup>F]fluoropropyl)acetamide</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/7854919" 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=7854919" alt="image 7854919 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]EF1</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]-2-(2-Nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(3-fluoropropyl)acetamide</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;">Hypoxic cells </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;">Intracellular reduction and 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;">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 id="A807" 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 id="A808" 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;">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><div id="EF-mono.Background"><h2 id="_EF-mono_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=18F%5BAll%20Fields%5D%20AND%20EF1%5BAll%20Fields%5D%20AND%20synthesis%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Hypoxia in malignant tumors is thought to be a major factor limiting the efficacy of chemotherapy and radiotherapy, and its accurate diagnosis is considered a very important and urgent problem to address. This has led to the search and development of hypoxia-targeted, non-invasive markers of tumor hypoxia. Among those markers, [<sup>18</sup>F]-labeled nitroimidazoles, used in conjunction with positron emission tomography (PET), offer an alternative that is less invasive and less prone to sampling error than the Eppendorf (oxygen) electrode method (<a class="bk_pop" href="#EF-mono.EXTYLES.1">1</a>, <a class="bk_pop" href="#EF-mono.EXTYLES.2"> 2</a>).</p><p>Fluoromisonidazole (<a href="/books/n/micad/FMISO/">[<sup>18</sup>F]FMISO</a>) is the most widely used nitroimidazole derivate used with PET. Novel 2-nitroimidazoles, such as <a href="/books/n/micad/FETA/">[<sup>18</sup>F]FETA</a> (<a class="bk_pop" href="#EF-mono.EXTYLES.3">3</a>), <a href="/books/n/micad/FETNIM/">[<sup>18</sup>F]FETNIM</a> (<a class="bk_pop" href="#EF-mono.EXTYLES.4">4</a>), <a href="/books/n/micad/BrFPN/">4-Br[<sup>18</sup>F]FPN</a> (<a class="bk_pop" href="#EF-mono.EXTYLES.5">5</a>), [<sup>18</sup>F]EF1, and <a href="/books/n/micad/EF5/">[<sup>18</sup>F]EF5</a> (<a class="bk_pop" href="#EF-mono.EXTYLES.6">6</a>), are currently being investigated as potential markers of tumor hypoxia.</p><p>[<sup>18</sup>F]EF1 is a molecule comparable to [<sup>18</sup>F]FETA, with the exception that [<sup>18</sup>F]EF1 carries an additional carbon on the side chain. [<sup>18</sup>F]EF1 is also a 3-monofluorinated analog of the pentafluorinated molecule EF5 (2-(2-nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,2,3,3,3-[<sup>18</sup>F]pentafluoropropyl)acetamide), which is used for the measurement of hypoxia in immunohistochemistry (<a class="bk_pop" href="#EF-mono.EXTYLES.7">7</a>) and flow cytometry (<a class="bk_pop" href="#EF-mono.EXTYLES.8">8</a>).</p><p>The oxygen-dependent metabolism of nitroimidazoles is an intracellular process consisting of a series of one-electron reductions. The nitro-radical anion produced in the first reduction step is very reactive toward oxygen, leaving no substrate for the second step of the reduction process. In contrast, a low-oxygen environment induces further reductive reactions that ultimately lead to the formation of either reactive products that can covalently bind to cell components or to charged species that diffuse slowly out of the tissues (<a class="bk_pop" href="#EF-mono.EXTYLES.1">1</a>). The reactive products observed during this multi-step process include nitroso (2e-), hydroxylamine (4e-), and amine (6e-) derivatives. When the fragmentation of the imidazole ring occurs, reactive portions of the molecule, such as glyoxal, bind to macromolecular components of cells in tissues and tumors (<a class="bk_pop" href="#EF-mono.EXTYLES.2">2</a>).</p></div><div id="EF-mono.Synthesis"><h2 id="_EF-mono_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=18F%5BAll%20Fields%5D%20AND%20EF1%5BAll%20Fields%5D%20AND%20synthesis%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Two modes of synthesis for [<sup>18</sup>F]EF1 were reported in 1999 by Kachur et al. (<a class="bk_pop" href="#EF-mono.EXTYLES.9">9</a>).</p><p>In the first mode, EF1 is synthesized from EBr1 by a nucleophilic substitution of bromine by fluorine using potassium Kryptofix 222 fluoride in dimethyl sulfoxide (DMSO). EBr1 is prepared from 2-(2-nitroimidazol-1<i>H</i>-yl)-acetic acid and 3-bromopropylamine hydrobromide using the mixed anhydride reaction with isobutyl chloroformate (<a class="bk_pop" href="#EF-mono.EXTYLES.10">10</a>). After dissolution in acetonitrile (MeCN) and storage over molecular sieves, the mixture is cooled to 0ºC under argon and stirred with an addition of isobutylchloroformate. A solution of 3-bromopropylamine hydrobromide (219 mg, 1 mmol) and 140 μl of NEt<sub>3</sub> (1 mmol) in 5 ml of MeCN is then added. After stirring, cooling to 0°C, and centrifugation, the resulting precipitate of NEt<sub>3</sub>H<sup>+</sup>Cl− is extracted and dried at room temperature. The final product, EBr1, is then recrystallized from hexane/EtOAc (10:1 ratio) and dried over molecular sieves. EBr1 is obtained with a yield of approximately 70%.</p><p>In the second mode, EF1 is prepared by following the protocol used for EBr1 described above, except that an equivalent quantity of 3-fluoro- instead of 3-bromopropylamine is used. In this case, the C–F bond in EF1 (which is not hydrolyzed) reacts with an excess of triethylamine (unlike the C–Br bond in EBr1). In this second method, the reaction conditions and separation procedure are different: a 2-fold excess of triethylamine is used in the reaction, and the dried reaction mixture, after centrifugation, is dissolved in dry EtOAc. After evaporation and dissolution of the residue in CHCl<sub>3</sub>, EF1 is extracted by H<sub>2</sub>O, and the aqueous layers are then combined and lyophilized. The yield is approximately 15% pure EF1.</p><p>The preparation of the radioactive carrier is performed by using [<sup>18</sup>F]fluoride, obtained by the <sup>18</sup>O(p,n) <sup>18</sup>F reaction using <sup>18</sup>O-enriched water. Details for this preparation are reported by Kachur et al. (<a class="bk_pop" href="#EF-mono.EXTYLES.9">9</a>).</p></div><div id="EF-mono.In_Vitro_Studies_Tes"><h2 id="_EF-mono_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=18F%5BAll%20Fields%5D%20AND%20EF1%5BAll%20Fields%5D%20AND%20%28%22in%20vitro%22%5BMeSH%20Terms%5D%20OR%20in%20vitro%5BText%20Word%5D%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="EF-mono.Animal_Studies"><h2 id="_EF-mono_Animal_Studies_">Animal Studies</h2><div id="EF-mono.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF1%20AND%20%22rodentia%22%5BMeSH%20Terms%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Evans et al. (<a class="bk_pop" href="#EF-mono.EXTYLES.11">11</a>) showed the ability of [<sup>18</sup>F]EF1 to differentiate hypoxic <i>versus</i> aerobic tumors in rodents, using the hypoxic Morris 7777 (Q7) hepatoma tumor type and the oxic 9LF glioma tumor model. The experimental procedure involved injecting intravenously approximately 1.9 MBq (0.05 mCi) of [<sup>18</sup>F]EF1 (1% of the animal’s weight), 3 m<span class="small-caps">m</span> of the carrier EF1,and 7 m<span class="small-caps">m</span> EF3 (2-(2-nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,2,3,3,3-[<sup>18</sup>F]trifluoropropyl)acetamide). The specific activity of [<sup>18</sup>F]EF1 for injection was 5.6 × 10<sup>4</sup> MBq/mol (1.51 × 10<sup>3</sup> mCi/mol).</p><p>The use of an excess of the carrier drug EF1 and EF3 made it possible to make an independent assessment of the drug biodistribution by more conventional means (e.g., high-performance liquid chromatography (HPLC)), as well as making an immunohistochemical detection of intracellular EF1/EF3 adducts in the tumors using EF3-specific antibodies. Biodistribution of [<sup>18</sup>F]EF1 was also performed in non-tumor-bearing mice, as a reference. After positron emission tomography (PET) studies, the tissues for all animals were removed and analyzed by γ-counting at 1, 5, 90, and 120 min after injection.</p><p>Results showed that for both rat tumor types, low retention of [<sup>18</sup>F]EF1 was obtained in muscle, heart, spleen and brain, whereas significantly higher levels were found in tumor and bone (tibia). γ-counts of excised organs and tissues were measured at 90 min after injection, and their uptake was expressed as a percentage of injected activity per gram of sample (% ID/g). The following results (% ID/g) were found for muscle, heart, spleen, brain, tumor, and bone (tibia), respectively (all values are x 10−<sup>3</sup>): for Q7 tumors, 2.5, 1.5, 3.0, 1.5, 6.5, and 13; for 9LF tumors, 1.5, 1.0, 1.8, 0.6, 2.5, and 12 (<a class="bk_pop" href="#EF-mono.EXTYLES.11">11</a>).</p><p>Studies using normal mice showed a rapid decrease of activity in all organs except bone (tibia), likely reflecting a bone contamination by [<sup>18</sup>F]F<sup>-</sup> and a very substantial increase of urine activity by 90 min after injection (0.6 fraction ID/g). For Q7 tumors, the tumor-to-muscle ratio (T/M) initially decreased (from approximately 2.0 at 10 min after injection to 1.7 at 50 min) and then increased (to approximately 2.4) to reach a plateau 125 min after injection. In contrast, the T/M ratio for 9L tumors never exceeded 1.0, and a steady decrease was observed over time (<a class="bk_pop" href="#EF-mono.EXTYLES.11">11</a>).</p></div><div id="EF-mono.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF1%20AND%20%28dog%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="EF-mono.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF1%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="EF-mono.Human_Studies"><h2 id="_EF-mono_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF1%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="EF-mono.references"><h2 id="_EF-mono_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.1">Nunn A , Linder K , Strauss HW . Nitroimidazoles and imaging hypoxia. <span><span class="ref-journal">Eur J Nucl Med. </span>1995;<span class="ref-vol">22</span>(3):265–280.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7789400" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7789400</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.2">Hodgkiss RJ . Use of 2-nitroimidazoles as bioreductive markers for tumour hypoxia. <span><span class="ref-journal">Anticancer Drug Des. </span>1998;<span class="ref-vol">13</span>(6):687–702.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9755725" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9755725</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.3">Rasey JS , Hofstrand PD , Chin LK , Tewson TJ . Characterization of [18F]fluoroetanidazole, a new radiopharmaceutical for detecting tumor hypoxia. <span><span class="ref-journal">J Nucl Med. </span>1999;<span class="ref-vol">40</span>(6):1072–1079.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10452326" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10452326</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.4">Yang DJ , Wallace S , Cherif A , Li C , Gretzer MB , Kim EE , Podoloff DA . Development of F-18-labeled fluoroerythronitroimidazole as a PET agent for imaging tumor hypoxia. <span><span class="ref-journal">Radiology. </span>1995;<span class="ref-vol">194</span>(3):795–800.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7862981" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7862981</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.5">Yamamoto F , Aoki M , Furusawa Y , Ando K , Kuwabara Y , Masuda K , Sasaki S , Maeda M . Synthesis and evaluation of 4-bromo-1-(3-[18F]fluoropropyl)-2-nitroimidazole with a low energy LUMO orbital designed as brain hypoxia-targeting imaging agent. <span><span class="ref-journal">Biol Pharm Bull. </span>2002;<span class="ref-vol">25</span>(5):616–621.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12033502" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12033502</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.6">Dolbier WR , Li AR , Koch CJ , Shiue CY , Kachur AV . [18F]-EF5, a marker for PET detection of hypoxia: synthesis of precursor and a new fluorination procedure. <span><span class="ref-journal">Appl Radiat Isot. </span>2001;<span class="ref-vol">54</span>(1):73–80.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11144255" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11144255</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.7">Evans SM , Joiner B , Jenkins WT , Laughlin KM , Lord EM , Koch CJ . Identification of hypoxia in cells and tissues of epigastric 9L rat glioma using EF5. <span><span class="ref-journal">Br J Cancer. </span>1995;<span class="ref-vol">72</span>(4):875–882.</span> [<a href="/pmc/articles/PMC2034029/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2034029</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/7547234" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7547234</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.8">Evans SM , Jenkins WT , Joiner B , Lord EM , Koch CJ . 2-Nitroimidazole (EF5) binding predicts radiation resistance in individual 9L s.c. tumors. <span><span class="ref-journal">Cancer Res. </span>1996;<span class="ref-vol">56</span>(2):405–411.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8542599" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8542599</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.9">Kachur AV , Dolbier WR , Evans SM , Shiue CY , Shiue GG , Skov KA , Baird IR , James BR , Li AR , Roche A , Koch CJ . Synthesis of new hypoxia markers EF1 and [18F]-EF1. <span><span class="ref-journal">Appl Radiat Isot. </span>1999;<span class="ref-vol">51</span>(6):643–650.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10581679" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10581679</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.10">Krejcarek GE , Tucker KL . Covalent attachment of chelating groups to macromolecules. <span><span class="ref-journal">Biochem Biophys Res Commun. </span>1977;<span class="ref-vol">77</span>(2):581–585.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/409400" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 409400</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="EF-mono.EXTYLES.11">Evans SM , Kachur AV , Shiue CY , Hustinx R , Jenkins WT , Shive GG , Karp JS , Alavi A , Lord EM , Dolbier WR , Koch CJ . Noninvasive detection of tumor hypoxia using the 2-nitroimidazole [18F]EF1. <span><span class="ref-journal">J Nucl Med. </span>2000;<span class="ref-vol">41</span>(2):327–336.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10688119" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10688119</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: NBK23464</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641663" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641663</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/EF5/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/F18-DCFPyL/" 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/NBK23464/?report=reader">PubReader</a></li><li><a href="/books/NBK23464/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23464" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23464" style="display:none" title="Cite this Page"><div class="bk_tt">The MICAD Research Team. 2-(2-Nitroimidazol-1H-yl)-(3-[18F]fluoropropyl)acetamide. 2005 Nov 5 [Updated 2005 Nov 17]. 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/NBK23464/pdf/Bookshelf_NBK23464.pdf">PDF version of this page</a> (135K)</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="#EF-mono.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#EF-mono.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#EF-mono.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#EF-mono.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#EF-mono.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#EF-mono.references" ref="log$=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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