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<script type="text/javascript" src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.boots.min.js"> </script><title>[18F]Fluoromethyl-d-tyrosine - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]">
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<meta name="citation_title" content="[18F]Fluoromethyl-d-tyrosine">
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<meta name="citation_publisher" content="National Center for Biotechnology Information (US)">
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<meta name="citation_date" content="2009/06/18">
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<meta name="citation_author" content="Arvind Chopra">
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<meta name="citation_pmid" content="20641261">
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<meta name="DC.Title" content="[18F]Fluoromethyl-d-tyrosine">
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<meta name="DC.Contributor" content="Arvind Chopra">
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<meta name="DC.Date" content="2009/06/18">
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<meta name="description" content="Cancerous tumors are formed by characteristically high levels of proliferating cells that have a constant high requirement for basic building blocks such as carbohydrates, nucleotides, and amino acids (AA) to maintain a suitable metabolic rate and to continue the synthesis of macromolecules such as DNA and proteins to sustain their phenotype (1). Because of the high carbohydrate demand of tumor cells, (18F)fluorodeoxy-glucose ((18F)FDG), which is not metabolized by the cells and as a consequence accumulates in neoplastic tumors, was developed to screen for cancers using positron emission tomography (PET) imaging. Although shown to be suitable for the detection of certain cancers (2), the main limitation of using (18F)FDG to detect tumors is that it tends to accumulate in some normal tissues (e.g., brain and heart) and inflamed tissues (3-5). Therefore, several 11C- and 18F-labeled AAs and their analogs, including l- and d-methyl-11C-methionine (l- and d-(11C)MET) and l- and d-O-(18F)fluoromethyl-tyrosine (l- and d-(18F)FMT), were developed as an alternative and have been evaluated for the uptake by and PET imaging of normal and tumor tissues (6, 7).">
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<meta name="og:title" content="[18F]Fluoromethyl-d-tyrosine">
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<meta name="og:description" content="Cancerous tumors are formed by characteristically high levels of proliferating cells that have a constant high requirement for basic building blocks such as carbohydrates, nucleotides, and amino acids (AA) to maintain a suitable metabolic rate and to continue the synthesis of macromolecules such as DNA and proteins to sustain their phenotype (1). Because of the high carbohydrate demand of tumor cells, (18F)fluorodeoxy-glucose ((18F)FDG), which is not metabolized by the cells and as a consequence accumulates in neoplastic tumors, was developed to screen for cancers using positron emission tomography (PET) imaging. Although shown to be suitable for the detection of certain cancers (2), the main limitation of using (18F)FDG to detect tumors is that it tends to accumulate in some normal tissues (e.g., brain and heart) and inflamed tissues (3-5). Therefore, several 11C- and 18F-labeled AAs and their analogs, including l- and d-methyl-11C-methionine (l- and d-(11C)MET) and l- and d-O-(18F)fluoromethyl-tyrosine (l- and d-(18F)FMT), were developed as an alternative and have been evaluated for the uptake by and PET imaging of normal and tumor tissues (6, 7).">
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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="_NBK23055_"><span class="title" itemprop="name">[<sup>18</sup>F]Fluoromethyl-<span class="small-caps">d</span>-tyrosine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"><span class="small-caps">d</span>-[<sup>18</sup>F]FMT</div><p class="contribs">Chopra A.</p><p class="fm-aai"><a href="#_NBK23055_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="figDFMT18FT1"><a href="/books/NBK23055/table/DFMT18F.T1/?report=objectonly" target="object" title="Table" class="img_link icnblk_img" rid-ob="figobDFMT18FT1"><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="DFMT18F.T1"><a href="/books/NBK23055/table/DFMT18F.T1/?report=objectonly" target="object" rid-ob="figobDFMT18FT1">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="DFMT18F.Background"><h2 id="_DFMT18F_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+fluoromethyl+D+tyrosine" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Cancerous tumors are formed by characteristically high levels of proliferating cells that have a constant high requirement for basic building blocks such as carbohydrates, nucleotides, and amino acids (AA) to maintain a suitable metabolic rate and to continue the synthesis of macromolecules such as DNA and proteins to sustain their phenotype (<a class="bibr" href="#DFMT18F.REF.1" rid="DFMT18F.REF.1">1</a>). Because of the high carbohydrate demand of tumor cells, (<sup>18</sup>F)fluorodeoxy-glucose ((<sup>18</sup>F)FDG), which is not metabolized by the cells and as a consequence accumulates in neoplastic tumors, was developed to screen for cancers using positron emission tomography (PET) imaging. Although shown to be suitable for the detection of certain cancers (<a class="bibr" href="#DFMT18F.REF.2" rid="DFMT18F.REF.2">2</a>), the main limitation of using (<sup>18</sup>F)FDG to detect tumors is that it tends to accumulate in some normal tissues (e.g., brain and heart) and inflamed tissues (<a class="bibr" href="#DFMT18F.REF.3" rid="DFMT18F.REF.3 DFMT18F.REF.4 DFMT18F.REF.5">3-5</a>). Therefore, several <sup>11</sup>C- and <sup>18</sup>F-labeled AAs and their analogs, including <span class="small-caps">l</span>- and <span class="small-caps">d</span>-methyl-<sup>11</sup>C-methionine (<span class="small-caps">l</span>- and <span class="small-caps">d</span>-(<sup>11</sup>C)MET) and <span class="small-caps">l</span>- and <span class="small-caps">d-</span><i>O</i>-(<sup>18</sup>F)fluoromethyl-tyrosine (<span class="small-caps">l</span>- and <span class="small-caps">d-</span>(<sup>18</sup>F)FMT), were developed as an alternative and have been evaluated for the uptake by and PET imaging of normal and tumor tissues (<a class="bibr" href="#DFMT18F.REF.6" rid="DFMT18F.REF.6 DFMT18F.REF.7">6, 7</a>).</p><p>Radiolabeled <span class="small-caps">l</span>-isomers of AAs behave like the naturally occurring compounds in a biological system, can be used for protein synthesis, are easily metabolized by mammalian cells, and have been shown to accumulate in non-target tissue in addition to tumors (<a class="bibr" href="#DFMT18F.REF.8" rid="DFMT18F.REF.8">8</a>). In contrast, the <span class="small-caps">d-</span>isomers are unnatural and, compared with the <span class="small-caps">l</span>-isomers, <sup>14</sup>C-labeled <span class="small-caps">d-</span>amino acids have been shown to have a higher tumor accumulation (<a class="bibr" href="#DFMT18F.REF.9" rid="DFMT18F.REF.9 DFMT18F.REF.10 DFMT18F.REF.11 DFMT18F.REF.12">9-12</a>). Although different AA transport systems are involved in the uptake of AAs, the AAs are transported primarily by the <span class="small-caps">l</span> AA transport systems (designated as LAT1 and LAT2), which are not sodium-dependent and can transport both the <span class="small-caps">l</span>- and <span class="small-caps">d-</span>isomers (<a class="bibr" href="#DFMT18F.REF.7" rid="DFMT18F.REF.7 DFMT18F.REF.13">7, 13</a>), including those containing a branched chain or an aromatic moiety (<a class="bibr" href="#DFMT18F.REF.14" rid="DFMT18F.REF.14">14</a>). Also, the LAT1 was reported to be expressed in the brain, spleen, placenta, and the testis (<a class="bibr" href="#DFMT18F.REF.15" rid="DFMT18F.REF.15">15</a>) and was reported to be overexpressed in malignant tumors (<a class="bibr" href="#DFMT18F.REF.16" rid="DFMT18F.REF.16 DFMT18F.REF.17">16, 17</a>). Tsukada et al. reported the tumor/blood uptake of the <span class="small-caps">d-</span>isomers of (<sup>18</sup>F)FMT, (<sup>18</sup>F)fluoroethyl-tyrosine, and (<sup>18</sup>F)fluoropropyl-tyrosine in tumor-bearing mice was 181%, 137%, and 101%, respectively, compared with their <span class="small-caps">l</span> homologs, indicating that the <span class="small-caps">d-</span>isomers could be potential PET imaging agents (<a class="bibr" href="#DFMT18F.REF.13" rid="DFMT18F.REF.13">13</a>). In another study, <span class="small-caps">d-</span>(<sup>18</sup>F)FMT was suggested to be a better PET tracer than the <span class="small-caps">l</span>- and <span class="small-caps">d-</span>isomers of (<sup>11</sup>C)MET because it showed lower accumulation in various normal organs and, compared with (<sup>18</sup>F)FDG, did not accumulate in inflamed tissue (<a class="bibr" href="#DFMT18F.REF.7" rid="DFMT18F.REF.7">7</a>). Urakami et al. studied the uptake of <span class="small-caps">l</span>- and <span class="small-caps">d</span>-(<sup>18</sup>F)FMT in cultured cells under <i>in vitro</i> conditions and evaluated the use of these radiolabeled compounds for the imaging of abdominal and brain tumors in rats and mice, respectively (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>).</p></div><div id="DFMT18F.Synthesis"><h2 id="_DFMT18F_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+FMT+synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The <span class="small-caps">l</span>- and <span class="small-caps">d</span>-isomers of tyrosine were reacted with (<sup>18</sup>F)fluoromethyl bromide to generate (<sup>18</sup>F)FMT as described elsewhere (<a class="bibr" href="#DFMT18F.REF.7" rid="DFMT18F.REF.7 DFMT18F.REF.13">7, 13</a>). Purity of the two enantiomers was determined with high-performance liquid chromatography using a CHIOBIOTIC T column with ethanol:water (1:1) as the eluent. (<sup>18</sup>F)FDG was produced as detailed by Oberdorfer et al. (<a class="bibr" href="#DFMT18F.REF.19" rid="DFMT18F.REF.19">19</a>). The specific activities of <span class="small-caps">d</span>-(<sup>18</sup>F)FMT, <span class="small-caps">l</span>-(<sup>18</sup>F)FMT, and (<sup>18</sup>F)FDG were 115 ± 10, 126 ± 12, and 144 ± 21 GBq/μmol, respectively (3.10 ± 0.27, 3.40 ± 0.32, and 3.89 ± 0.56 Ci/μmol, respectively) (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>). The radiochemical purities of <span class="small-caps">d</span>-(<sup>18</sup>F)FMT, <span class="small-caps">l</span>-(<sup>18</sup>F)FMT, and (<sup>18</sup>F)FDG were 99.6 ± 0.4%, 99.8 ± 0.3%, and 100.0 ± 0.0%, respectively (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>). The average time of radiochemical synthesis and the yield of these labeled compounds were not reported.</p></div><div id="DFMT18F.In_Vitro_Studies_Tes"><h2 id="_DFMT18F_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+FMT+in+vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Urakami et al. studied the uptake of d-(18F)FMT and l-(18F)FMT in rat C6 glioma and HeLa cells at select time points for up to 30 min after exposure to the radiochemicals (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>). Both cell lines were reported to show a higher uptake of the l-isomer, and the uptake was not saturated even at 60 min. The release of both labeled isomers was studied using HeLa cells loaded with the l- and d-isomers, respectively, in AA-free medium and in presence or absence of excess l-leucine (100 μM) (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>). Presence of l-leucine was reported to accelerate the release of both labeled isomers from the loaded HeLa cells. The uptake and release study indicated that the transport of the labeled d-isomer was lower than the transport of the l-isomer under in vitro conditions. In another study, the uptake of both labeled isomers in C6 glioma cells was reported to be inhibited by the presence of excess (1 mM) l-isomers of methionine, phenylalanine, and tyrosine. Uptake of the two labeled isomers was also inhibited by 2-aminobicyclo-(2,2,1)-heptane-2-carboxylic acid, a selective inhibitor of the l AA transport system, but no inhibition was observed with l-glycine. These results indicated that both the labeled isomers were transported by the l AA transport system (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>). This observation was confirmed with a reverse-transcriptase polymerase chain reaction analysis of the C6 glioma and HeLa cells, and it was observed that only the LAT1 mRNA was expressed in both the cell lines.</p></div><div id="DFMT18F.Animal_Studies"><h2 id="_DFMT18F_Animal_Studies_">Animal Studies</h2><div id="DFMT18F.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+FMT+rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Urakami et al. evaluated the use of <span class="small-caps">d</span>-(<sup>18</sup>F)FMT, <span class="small-caps">l</span>-(<sup>18</sup>F)FMT, and (<sup>18</sup>F)FDG, respectively, for PET imaging in normal tissue (left leg) and HeLa cell xenograft tumors (right leg) in mice (<i>n</i> > 3 animals for each radiocompound) (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>). The standard uptake values (SUV) for <span class="small-caps">d</span>-(<sup>18</sup>F)FMT and <span class="small-caps">l</span>-(<sup>18</sup>F)FMT in the tumor tissue were 1.33 and 1.642, respectively, but these values were 0.488 and 0.874, respectively, in the normal tissue. Therefore, among these labeled compounds, <span class="small-caps">d</span>-(<sup>18</sup>F)FMT was reported to show a more clear difference between the normal tissue and tumor tissue. Under the same experimental conditions, (<sup>18</sup>F)FDG was reported to have a lower accumulation in the tumor compared with either (<sup>18</sup>F)FMT isomer, and an uptake of the labeled carbohydrate derivative was also observed in the normal brain and heart of the animals.</p><p>Another study performed to image C6 glioma tumors in mouse brain (<i>n</i> = 5 animals per labeled compound) also showed that <span class="small-caps">d</span>-(<sup>18</sup>F)FMT was a superior PET imaging agent compared with either <span class="small-caps">l</span>-(<sup>18</sup>F)FMT or (<sup>18</sup>F)FDG (<a class="bibr" href="#DFMT18F.REF.18" rid="DFMT18F.REF.18">18</a>).</p><p>Tsukada et al. compared the use of <span class="small-caps">d</span>-(<sup>18</sup>F)FMT to the use of <i>O</i>-<sup>11</sup>C-methyl-<span class="small-caps">d</span>-tyrosine (<span class="small-caps">d</span>-(<sup>11</sup>C)CMT) and to <span class="small-caps">d</span>- and <span class="small-caps">l</span>-(<sup>11</sup>C)MET for the PET imaging of HeLa tumors in mice (<i>n</i> = 5 animals per labeled AA) (<a class="bibr" href="#DFMT18F.REF.7" rid="DFMT18F.REF.7">7</a>). Although the tumor SUV levels of <span class="small-caps">d</span>-isomers of (<sup>11</sup>C)MET, (<sup>11</sup>C)CMT, and (<sup>18</sup>F)FMT were 261%, 72%, and 95%, respectively, of the corresponding <span class="small-caps">l</span>-isomer of the AAs at 60 min after administration, the tumor/blood ratios of the <span class="small-caps">d</span>-isomers were reported to be 130%, 140%, and 182%, respectively, of the <span class="small-caps">l</span>-isomers. Also, the <span class="small-caps">d</span>-isomers of the various labeled AAs had a much lower uptake in the abdominal organs compared with <span class="small-caps">l</span>-isomers of AAs. The investigators also compared the uptake of <span class="small-caps">d</span>- and <span class="small-caps">l</span>-(<sup>11</sup>C)MET, <span class="small-caps">d</span>-(<sup>11</sup>C)CMT, and <span class="small-caps">d</span>-(<sup>18</sup>F)FMT to (<sup>18</sup>F)FDG for the visualization of turpentine-induced inflammatory tissue in these animals (<i>n</i> = 5 mice per labeled AA) (<a class="bibr" href="#DFMT18F.REF.7" rid="DFMT18F.REF.7">7</a>). Among these labeled compounds, only (<sup>18</sup>F)FDG was reported to show a high accumulation in the inflamed tissue. From these studies the investigators concluded that the <span class="small-caps">d</span>-isomers of (<sup>11</sup>C)CMT and (<sup>18</sup>F)FMT were probably superior to <span class="small-caps">l</span>- and <span class="small-caps">d</span>-(<sup>11</sup>C)MET for tumor imaging using PET.</p></div><div id="DFMT18F.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+FMT+Non-Primate+Mammals" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="DFMT18F.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+FMT+Non-Human+Primates" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="DFMT18F.Human_Studies"><h2 id="_DFMT18F_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F+FMT+Human+Studies" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="DFMT18F.Supplemental_Informa"><h2 id="_DFMT18F_Supplemental_Informa_">Supplemental Information</h2><p>
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<a href="/books/n/micad/disclaimer/?report=reader">[Disclaimer]</a>
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</p></div><div id="DFMT18F.References"><h2 id="_DFMT18F_References_">References</h2><dl class="temp-labeled-list"><dl class="bkr_refwrap"><dt>1.</dt><dd><div class="bk_ref" id="DFMT18F.REF.1">Ganapathy V., Thangaraju M., Prasad P.D.
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<em>Nutrient transporters in cancer: relevance to Warburg hypothesis and beyond.</em>
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<span><span class="ref-journal">Pharmacol Ther. </span>2009;<span class="ref-vol">121</span>(1):29–40.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18992769" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18992769</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>2.</dt><dd><div class="bk_ref" id="DFMT18F.REF.2">Yamazaki Y., Saitoh M., Notani K., Tei K., Totsuka Y., Takinami S., Kanegae K., Inubushi M., Tamaki N., Kitagawa Y.
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<em>Assessment of cervical lymph node metastases using FDG-PET in patients with head and neck cancer.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2008;<span class="ref-vol">22</span>(3):177–84.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18498032" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18498032</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>3.</dt><dd><div class="bk_ref" id="DFMT18F.REF.3">Miyamoto J., Tatsuzawa K., Owada K., Kawabe T., Sasajima H., Mineura K.
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<em>Usefulness and limitations of fluorine-18-fluorodeoxyglucose positron emission tomography for the detection of malignancy of orbital tumors.</em>
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<span><span class="ref-journal">Neurol Med Chir (Tokyo). </span>2008;<span class="ref-vol">48</span>(11):495–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19029776" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19029776</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>4.</dt><dd><div class="bk_ref" id="DFMT18F.REF.4">Suzuki H., Hasegawa Y., Terada A., Ogawa T., Hyodo I., Suzuki M., Nakashima T., Tamaki T., Nishio M.
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<em>Limitations of FDG-PET and FDG-PET with computed tomography for detecting synchronous cancer in pharyngeal cancer.</em>
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<span><span class="ref-journal">Arch Otolaryngol Head Neck Surg. </span>2008;<span class="ref-vol">134</span>(11):1191–5.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19015450" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19015450</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>5.</dt><dd><div class="bk_ref" id="DFMT18F.REF.5">Terauchi T., Murano T., Daisaki H., Kanou D., Shoda H., Kakinuma R., Hamashima C., Moriyama N., Kakizoe T.
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<em>Evaluation of whole-body cancer screening using 18F-2-deoxy-2-fluoro-D-glucose positron emission tomography: a preliminary report.</em>
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<span><span class="ref-journal">Ann Nucl Med. </span>2008;<span class="ref-vol">22</span>(5):379–85.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18600415" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18600415</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>6.</dt><dd><div class="bk_ref" id="DFMT18F.REF.6">Ishiwata K., Kawamura K., Wang W.F., Furumoto S., Kubota K., Pascali C., Bogni A., Iwata R.
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<em>Evaluation of O-[11C]methyl-L-tyrosine and O-[18F]fluoromethyl-L-tyrosine as tumor imaging tracers by PET.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2004;<span class="ref-vol">31</span>(2):191–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15013484" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15013484</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>7.</dt><dd><div class="bk_ref" id="DFMT18F.REF.7">Tsukada H., Sato K., Fukumoto D., Nishiyama S., Harada N., Kakiuchi T.
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<em>Evaluation of D-isomers of O-11C-methyl tyrosine and O-18F-fluoromethyl tyrosine as tumor-imaging agents in tumor-bearing mice: comparison with L- and D-11C-methionine.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2006;<span class="ref-vol">47</span>(4):679–88.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16595503" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16595503</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>8.</dt><dd><div class="bk_ref" id="DFMT18F.REF.8">Bauwens M., Keyaerts M., Lahoutte T., Kersemans K., Caveliers V., Bossuyt A., Mertens J.
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<em>Intra-individual comparison of the human biodistribution and dosimetry of the D and L isomers of 2-[123I]iodo-phenylalanine.</em>
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<span><span class="ref-journal">Nucl Med Commun. </span>2007;<span class="ref-vol">28</span>(10):823–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17728613" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17728613</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>9.</dt><dd><div class="bk_ref" id="DFMT18F.REF.9">Bauwens M., Lahoutte T., Kersemans K., Gallez C., Bossuyt A., Mertens J.
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<em>Comparison of the uptake of [123/125I]-2-iodo-D-tyrosine and [123/125I]-2-iodo-L-tyrosine in R1M rhabdomyosarcoma cells in vitro and in R1M tumor-bearing Wag/Rij rats in vivo.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2006;<span class="ref-vol">33</span>(6):735–41.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16934692" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16934692</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>10.</dt><dd><div class="bk_ref" id="DFMT18F.REF.10">Kersemans V., Cornelissen B., Bacher K., Kersemans K., Thierens H., Dierckx R.A., De Spiegeleer B., Slegers G., Mertens J.
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<em>In vivo evaluation and dosimetry of 123I-2-iodo-D-phenylalanine, a new potential tumor-specific tracer for SPECT, in an R1M rhabdomyosarcoma athymic mouse model.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2005;<span class="ref-vol">46</span>(12):2104–11.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16330577" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16330577</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>11.</dt><dd><div class="bk_ref" id="DFMT18F.REF.11">Kersemans V., Cornelissen B., Kersemans K., Bauwens M., Achten E., Dierckx R.A., Mertens J., Slegers G.
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<em>In vivo characterization of 123/125I-2-iodo-L-phenylalanine in an R1M rhabdomyosarcoma athymic mouse model as a potential tumor tracer for SPECT.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2005;<span class="ref-vol">46</span>(3):532–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15750170" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15750170</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>12.</dt><dd><div class="bk_ref" id="DFMT18F.REF.12">Foulon C.F., Reist C.J., Bigner D.D., Zalutsky M.R.
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<em>Radioiodination via D-amino acid peptide enhances cellular retention and tumor xenograft targeting of an internalizing anti-epidermal growth factor receptor variant III monoclonal antibody.</em>
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<span><span class="ref-journal">Cancer Res. </span>2000;<span class="ref-vol">60</span>(16):4453–60.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10969792" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10969792</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>13.</dt><dd><div class="bk_ref" id="DFMT18F.REF.13">Tsukada H., Sato K., Fukumoto D., Kakiuchi T.
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<em>Evaluation of D-isomers of O-18F-fluoromethyl, O-18F-fluoroethyl and O-18F-fluoropropyl tyrosine as tumour imaging agents in mice.</em>
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<span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2006;<span class="ref-vol">33</span>(9):1017–24.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16699766" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16699766</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>14.</dt><dd><div class="bk_ref" id="DFMT18F.REF.14">Kanai Y., Endou H.
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<em>Heterodimeric amino acid transporters: molecular biology and pathological and pharmacological relevance.</em>
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<span><span class="ref-journal">Curr Drug Metab. </span>2001;<span class="ref-vol">2</span>(4):339–54.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11766986" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11766986</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>15.</dt><dd><div class="bk_ref" id="DFMT18F.REF.15">Prasad P.D., Wang H., Huang W., Kekuda R., Rajan D.P., Leibach F.H., Ganapathy V.
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<em>Human LAT1, a subunit of system L amino acid transporter: molecular cloning and transport function.</em>
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<span><span class="ref-journal">Biochem Biophys Res Commun. </span>1999;<span class="ref-vol">255</span>(2):283–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10049700" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10049700</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>16.</dt><dd><div class="bk_ref" id="DFMT18F.REF.16">Kim D.K., Kim I.J., Hwang S., Kook J.H., Lee M.C., Shin B.A., Bae C.S., Yoon J.H., Ahn S.G., Kim S.A., Kanai Y., Endou H., Kim J.K.
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<em>System L-amino acid transporters are differently expressed in rat astrocyte and C6 glioma cells.</em>
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<span><span class="ref-journal">Neurosci Res. </span>2004;<span class="ref-vol">50</span>(4):437–46.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15567481" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15567481</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>17.</dt><dd><div class="bk_ref" id="DFMT18F.REF.17">Yanagida O., Kanai Y., Chairoungdua A., Kim D.K., Segawa H., Nii T., Cha S.H., Matsuo H., Fukushima J., Fukasawa Y., Tani Y., Taketani Y., Uchino H., Kim J.Y., Inatomi J., Okayasu I., Miyamoto K., Takeda E., Goya T., Endou H.
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<em>Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines.</em>
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<span><span class="ref-journal">Biochim Biophys Acta. </span>2001;<span class="ref-vol">1514</span>(2):291–302.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11557028" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11557028</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>18.</dt><dd><div class="bk_ref" id="DFMT18F.REF.18">Urakami T., Sakai K., Asai T., Fukumoto D., Tsukada H., Oku N.
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<em>Evaluation of O-[(18)F]fluoromethyl-d-tyrosine as a radiotracer for tumor imaging with positron emission tomography.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2009;<span class="ref-vol">36</span>(3):295–303.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19324275" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19324275</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>19.</dt><dd><div class="bk_ref" id="DFMT18F.REF.19">Oberdorfer F., Hull W.E., Traving B.C., Maier-Borst W.
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<em>Synthesis and purification of 2-deoxy-2-[18F]fluoro-D-glucose and 2-deoxy-2-[18F]fluoro-D-mannose: characterization of products by 1H- and 19F-NMR spectroscopy.</em>
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<span><span class="ref-journal">Int J Rad Appl Instrum [A] </span>1986;<span class="ref-vol">37</span>(8):695–701.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/3021670" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 3021670</span></a>]</div></dd></dl></dl></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK23055_pubdet_">Publication Details</h2><h3>Author Information and Affiliations</h3><div class="contrib half_rhythm"><span itemprop="author">Arvind Chopra</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH, Bethesda, MD 20894<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><h3>Publication History</h3><p class="small">Created: <span itemprop="datePublished">May 7, 2009</span>; Last Update: <span itemprop="dateModified">June 18, 2009</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>Chopra A. [18F]Fluoromethyl-d-tyrosine. 2009 May 7 [Updated 2009 Jun 18]. 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/IL-1ra-18F/?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/FMISO/?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="figobDFMT18FT1"><div id="DFMT18F.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23055/table/DFMT18F.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__DFMT18F.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;">[<sup>18</sup>F]Fluoromethyl- <span class="small-caps">d</span>-tyrosine<br /></td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;"></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;"><span class="small-caps">d</span>-[<sup>18</sup>F]FMT<br /></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;">L-amino acid transporter 1</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;">Transporter</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 not available 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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