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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]" /><meta name="citation_title" content="L- and D-S-(3-[18F]fluoropropyl)homocysteine" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2012/02/16" /><meta name="citation_author" content="Arvind Chopra" /><meta name="citation_pmid" content="21994969" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK65018/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="L- and D-S-(3-[18F]fluoropropyl)homocysteine" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Arvind Chopra" /><meta name="DC.Date" content="2012/02/16" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK65018/" /><meta name="description" content="High energy consumption and constant proliferation are the hallmarks of all cells with a malignant phenotype. 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To accommodate the increased demand for aa, the malignant cells overexpress the aa transporters (phenylalanine and tyrosine use the l-type transporter), and this phenomenon promotes the rapid uptake and accumulation of the radiolabeled aa in the tumors. Therefore, noninvasive imaging with a radiolabeled aa can be used to detect cancerous lesions within a short time after administration of an aa tracer. Among the various radiolabeled aa tracers, [18F]-α-methyl-tyrosine is often used in the clinic, but the low yield of the final labeled product prohibits the use of this labeled compound in most oncology centers (1)." /><meta name="og:title" content="L- and D-S-(3-[18F]fluoropropyl)homocysteine" /><meta name="og:type" content="book" /><meta name="og:description" content="High energy consumption and constant proliferation are the hallmarks of all cells with a malignant phenotype. To maintain a high pace of protein and DNA synthesis, such cells have an increased demand for various nutrients, glucose, and amino acids (aa). Therefore, radiotracers such as 18F-labeled fluorodeoxyglucose, which is taken up by the cell through the glucose transporter, are often used with positron emission tomography (PET) to detect cancerous tumors. This agent, however, is not able to distinguish between malignant tissue, inflammation, and tissues that normally have high glucose consumption, such as the brain (1). As an alternative, radiolabeled aa and their derivatives, such as those of phenylalanine and tyrosine, have been used to detect neoplastic tumors because these lesions show increased utilization of aa for the synthesis of proteins and other cellular components (2, 3). To accommodate the increased demand for aa, the malignant cells overexpress the aa transporters (phenylalanine and tyrosine use the l-type transporter), and this phenomenon promotes the rapid uptake and accumulation of the radiolabeled aa in the tumors. Therefore, noninvasive imaging with a radiolabeled aa can be used to detect cancerous lesions within a short time after administration of an aa tracer. 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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="#__NBK65018_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK65018_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/FDOPA/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CNPFH18F/" 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="_NBK65018_"><span class="title" itemprop="name">L- and D-<i>S</i>-(3-[<sup>18</sup>F]fluoropropyl)homocysteine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"><span class="small-caps">l</span>- and <span class="small-caps">d</span>-[<sup>18</sup>F]FPHCys</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK65018_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK65018_ai__"><div class="contrib half_rhythm"><span itemprop="author">Arvind Chopra</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, 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></div><p class="small">Created: <span itemprop="datePublished">January 10, 2012</span>; Last Update: <span itemprop="dateModified">February 16, 2012</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="FPHCys18F.T.nc_chemical_namel_and_ds318f" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK65018/table/FPHCys18F.T.nc_chemical_namel_and_ds318f/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__FPHCys18F.T.nc_chemical_namel_and_ds318f_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;"><span class="small-caps">l</span>- and <span class="small-caps">d</span>-<i>S</i>-(3-[<sup>18</sup>F]fluoropropyl)homocysteine<br /></td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<span class="graphic"><img src="/books/NBK65018/bin/FPHCys18F.jpg" alt="Image FPHCys18F.jpg" /></span>
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</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><span class="small-caps">l</span>- and <span class="small-caps">d</span>-[<sup>18</sup>F]FPHCys<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;">LAT1 amino acid transporter</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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<br />
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Structures of L- and D-[<sup>18</sup>F]FPHCys</td></tr></tbody></table></div></div><div id="FPHCys18F.Background"><h2 id="_FPHCys18F_Background_">Background</h2><p>[<a href="/pubmed?term=%22SUBSTANCENAME%22%5BSubstance%5D%20AND%20Background%5BAll%20Fields%5D&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>High energy consumption and constant proliferation are the hallmarks of all cells with a malignant phenotype. To maintain a high pace of protein and DNA synthesis, such cells have an increased demand for various nutrients, glucose, and amino acids (aa). Therefore, radiotracers such as <sup>18</sup>F-labeled fluorodeoxyglucose, which is taken up by the cell through the glucose transporter, are often used with positron emission tomography (PET) to detect cancerous tumors. This agent, however, is not able to distinguish between malignant tissue, inflammation, and tissues that normally have high glucose consumption, such as the brain (<a class="bk_pop" href="#FPHCys18F.REF.1">1</a>). As an alternative, radiolabeled aa and their derivatives, such as those of phenylalanine and tyrosine, have been used to detect neoplastic tumors because these lesions show increased utilization of aa for the synthesis of proteins and other cellular components (<a class="bk_pop" href="#FPHCys18F.REF.2" data-bk-pop-others="FPHCys18F.REF.3">2, 3</a>). To accommodate the increased demand for aa, the malignant cells overexpress the aa transporters (phenylalanine and tyrosine use the <span class="small-caps">l</span>-type transporter), and this phenomenon promotes the rapid uptake and accumulation of the radiolabeled aa in the tumors. Therefore, noninvasive imaging with a radiolabeled aa can be used to detect cancerous lesions within a short time after administration of an aa tracer. Among the various radiolabeled aa tracers, [<sup>18</sup>F]-α-methyl-tyrosine is often used in the clinic, but the low yield of the final labeled product prohibits the use of this labeled compound in most oncology centers (<a class="bk_pop" href="#FPHCys18F.REF.1">1</a>).</p><p><i>S</i>-(2-[<sup>11</sup>C]methyl)-<span class="small-caps">l</span>-methionine ([<sup>11</sup>C]MET; half-life of <sup>11</sup>C = ~20 min) is another aa derivative that is widely used for the PET imaging of tumors, but because MET contributes to a diverse array of biosynthetic reactions such as DNA synthesis, protein synthesis, etc., the radiolabeled macromolecules derived from [<sup>11</sup>C]MET along with the biodegradation products of the labeled molecules generate a high background signal in the tissues (<a class="bk_pop" href="#FPHCys18F.REF.4">4</a>). As a consequence, the imaging of tumors with [<sup>11</sup>C]MET has limited utility in the clinic and this tracer has been used primarily for the noninvasive visualization of <a href="http://www.cedars-sinai.edu/Patients/Health-Conditions/Gliomas.aspx" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">gliomas</a> in the brain, and very little information is available to indicate that labeled MET is suitable for the detection of tumors in other parts of the body (<a class="bk_pop" href="#FPHCys18F.REF.3" data-bk-pop-others="FPHCys18F.REF.4">3, 4</a>). Investigators developed <i>S</i>-(2-[<sup>18</sup>F]fluoroethyl)-L-homocysteine, an analog of MET, as a possible agent for the imaging of cancerous tumors, but this agent was unstable in aqueous media and could be used for the detection of these lesions (<a class="bk_pop" href="#FPHCys18F.REF.5">5</a>). In a continued effort to develop an aa derivative that can be used for the imaging of non-glioma tumors, the <span class="small-caps">d</span> and <span class="small-caps">l</span> enantiomers of <i>S</i>-(3-[<sup>18</sup>F]fluoropropyl)homocysteine ([<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys and [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys) were synthesized, and the biodistribution and tumor imaging properties of these compounds in nude mice bearing xenograft tumors derived from different non-glioma human cancer cell lines was investigated (<a class="bk_pop" href="#FPHCys18F.REF.4" data-bk-pop-others="FPHCys18F.REF.6">4, 6</a>).</p><div id="FPHCys18F.Related_Resource_Links"><h3>Related Resource Links</h3><p>Amino acid transporter related chapters in <a href="/books/?term=amino+acid+transporters+AND+micad%5Bbook%5D&view=chapter&p%24a=&p%24l=PBooksLayout&p%24st=books" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">MICAD</a></p><p><a href="http://clinicaltrials.gov/ct2/results?term=Amino+acid+transporters" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Clinical trials</a> related to amino acid transporters</p><p><a href="http://clinicaltrials.gov/ct2/results?term=Amino+acid+as+imaging+compound" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Clinical trials</a> using amino acids as imaging agents</p><p><a href="/omim?Db=omim&Cmd=DetailsSearch&Term=amino%5BAll+Fields%5D+AND+acid%5BAll+Fields%5D+AND+transporter%5BAll+Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporters</a> in Online Mendelian Inheritance in Man (OMIM)</p><p>Gene information regarding <a href="/gene/23428" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"><span class="small-caps">l</span>- type amino acid transporters</a></p><p><a href="http://www.cystinuria.org/resources/education/molecular_basics/" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Cystinuria</a> – an inherited defect of amino acid transport</p><p>Human amino acid transport disorders [<a href="/pubmed?term=amino%20acid%20transport%20disorders&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Human amino acid metabolism disorders [<a href="/pubmed?term=Human%20amino%20acid%20metabolism%20disorders&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p></div></div><div id="FPHCys18F.Synthesis"><h2 id="_FPHCys18F_Synthesis_">Synthesis</h2><p>[<a href="/pubmed?term=S-%283-%5B18F%5Dfluoropropyl%29homocysteine%20synthesis&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The synthesis of <span class="small-caps">d</span>-FPHCys and <span class="small-caps">l</span>-FPHCys and their labeling with <sup>18</sup>F have been described by Bourdier et al. (<a class="bk_pop" href="#FPHCys18F.REF.4">4</a>). The enantiomeric purity, radiochemical purity, and radiochemical yield of both enantiomers of [<sup>18</sup>F]FPHCys were typically >98%, >98%, and 20 ± 5%, respectively. The total time to prepare both tracers, from purification with high-performance liquid chromatography (HPLC), formulation, and sterile filtration through a 0.22-μm filter (for biological studies), was ~65 min. Both <sup>18</sup>F-labeled compounds had a specific activity of >185 GBq/μmol (~5 Ci/μmol). The stability of the two enantiomers was not reported.</p></div><div id="FPHCys18F.In_Vitro_Studies_Testing_in_Ce"><h2 id="_FPHCys18F_In_Vitro_Studies_Testing_in_Ce_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed?term=S-%283-%5B18F%5Dfluoropropyl%29homocysteine%20in%20vitro&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The uptake of [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys and [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys was studied in <a href="https://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CRL-1619&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">A375</a> (human malignant melanoma cell line) and <a href="https://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=HTB-38&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">HT29</a> (human colorectal adenocarcinoma cell line) cells (<a class="bk_pop" href="#FPHCys18F.REF.4">4</a>). Radioactivity from [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys was rapidly taken up by the A375 cells (with 50% of total accumulation within the initial 2 min after exposure); accumulation peaked at 60 min (9% of total dose/10<sup>5</sup> cells) and gradually decreased to ~4.5% of total dose by 240 min. A similar uptake profile was observed with [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys in the A375 cells; however, the initial uptake was more gradual compared to that of [<sup>18</sup>F]-<span class="small-caps">L</span>-FPHCys, and the maximum accumulation of label was 6.8% of total dose/10<sup>5</sup> cells at 60 min after exposure, which was followed by a gradual decrease in uptake up to 240 min (~3% of total dose). The maximum uptake of [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys and [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys by the HT29 cells was 2% and 1.6% of total dose, respectively, at 15 min, and the accumulation decreased to ~1% of total dose for both tracers at 240 min.</p><p>From competitive inhibition experiments it was determined that the D and L labeled enantiomers of FPHCys were transported in the two cells types by the <span class="small-caps">l</span> aa transporter (LAT) system (<a class="bk_pop" href="#FPHCys18F.REF.4">4</a>). In another study, [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys was shown to be transported into <a href="https://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CRL-2592&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">A431</a> (human epidermoid carcinoma cell line) and <a href="https://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CCL-222&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Colo 205</a> (human colorectal adenocarcinoma cell line) cells by the LAT1 subtype of the LAT (<a class="bk_pop" href="#FPHCys18F.REF.6">6</a>). In this study, HT29 and <a href="https://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CRL-1435&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PC3</a> (a human prostate adenocarcinoma cell line) cells showed a low uptake of the tracer, and both cell types were determined to have a low expression of LAT1 (as assessed with quantitative polymerase chain reaction of LAT1 mRNA). The uptake of [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys by the four cell lines was shown to correlate well (<i>R</i><sup>2</sup> = 0.85) with the expression of LAT1 in these cells.</p></div><div id="FPHCys18F.Animal_Studies"><h2 id="_FPHCys18F_Animal_Studies_">Animal Studies</h2><div id="FPHCys18F.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed?term=S-%283-%5B18F%5Dfluoropropyl%29homocysteine%20rodentia&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys and [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys was studied in nude mice bearing A375 cell xenograft tumors (<i>n</i> = 3 animals/group) as described by Bourdier et al. (<a class="bk_pop" href="#FPHCys18F.REF.4">4</a>). Results obtained from this study were presented as percent of injected dose per gram tissue (% ID/g). The amounts of tracer in the blood from [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys and [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys were 5.17 ± 0.18% ID/g and 3.51 ± 0.68% ID/g, 4.44 ± 0.54% ID/g and 2.51 ± 0.35% ID/g, 2.32 ± 0.33% ID/g and 0.89 ± 0.10% ID/g, and 1.38 ± 0.37% ID/g at 15, 30, 60, and 120 min postinjection (p.i.), respectively. The accumulation of radioactivity from [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys in the tumor was 9.41 ± 1.21% ID/g, 8.28 ± 0.81% ID/g, 5.64 ± 0.95% ID/g, and 4.40 ± 0.67% ID/g at 15, 30, 60, and 120 min p.i., respectively. With [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys, the uptake of label in the tumor was 6.01 ± 0.77% ID/g, 5.87 ± 1.14% ID/g, 3.91 ± 0.32% ID/g, and 1.68 ± 0.27% ID/g at 15, 30, 60, and 120 min p.i., respectively. The tumor/blood ratios for [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys and [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys at 60–120 min p.i. were ~4–5 and ~2–3, respectively. HPLC analysis showed that 90% and 80% of [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys remained intact in the pancreas and urine at 60 min, respectively; however, only 30% (pancreas) and 10% (urine) of [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys remained intact at the same time point. At 120 min p.i., a very low percentage (<3%) of both labeled enantiomers was incorporated into proteins of the brain, pancreas, plasma, and the tumors, indicating that the tracers had low incorporation in the macromolecules. No blocking studies were reported.</p><p>Whole-body PET images were acquired over a period of 120 min after intravenous injection of either [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys or [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys in nude mice bearing A375 tumors (<i>n</i> = 3 animals) (<a class="bk_pop" href="#FPHCys18F.REF.4">4</a>). Images acquired at 60 min p.i. showed that the kidneys, followed by the tumors, had the maximum accumulation of radioactivity with both labeled compounds. Bladders of mice injected with [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys showed a higher retention of radioactivity than those injected with [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys. In addition, compared with [<sup>18</sup>F]-<span class="small-caps">l</span>-FPHCys, a lower background uptake of label from [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys was observed in the liver and the muscles. No blocking studies were reported.</p><p>In another study, whole-body PET imaging was performed on nude mice bearing A431, Colo 205, PC3, or HT29 cell tumors (<i>n</i> = 6–10 animals/cell type) at 90 min p.i. of [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys (<a class="bk_pop" href="#FPHCys18F.REF.6">6</a>). From the images it was determined that the amount of radioactivity in the A431and Colo 205 cell tumors was ~3-fold higher than background, and accumulated radioactivity in the PC3 and HT29 cell tumors was ~2-fold higher than background, indicating that uptake of the label in these lesions had a high correlation (<i>R</i><sup>2</sup> = 0.99) with expression of the LAT1 transporter in these cells (see <i>In Vitro</i> Studies section for details).</p><p>From these studies, the investigators concluded that [<sup>18</sup>F]-<span class="small-caps">d</span>-FPHCys can be a suitable imaging agent for the detection of tumors in mice, although more work is necessary before it can be used in the clinic (<a class="bk_pop" href="#FPHCys18F.REF.4" data-bk-pop-others="FPHCys18F.REF.6">4, 6</a>).</p></div><div id="FPHCys18F.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed?term=S-%283-%5B18F%5Dfluoropropyl%29homocysteine%20Other%20Non-Primate%20Mammals&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FPHCys18F.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed?term=S-%283-%5B18F%5Dfluoropropyl%29homocysteine%20Non-Human%20Primates&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="FPHCys18F.Human_Studies"><h2 id="_FPHCys18F_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed?term=S-%283-%5B18F%5Dfluoropropyl%29homocysteine%20Human%20Studies&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FPHCys18F.Supplemental_Information"><h2 id="_FPHCys18F_Supplemental_Information_">Supplemental Information</h2><p>[<a href="/books/n/micad/disclaimer/">Disclaimers</a>]</p><p>No information is currently available.</p></div><div id="FPHCys18F.References"><h2 id="_FPHCys18F_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="FPHCys18F.REF.1">Kong F.L., Ali M.S., Zhang Y., Oh C.S., Yu D.F., Chanda M., Yang D.J.
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<em>Synthesis and evaluation of amino acid-based radiotracer 99mTc-N4-AMT for breast cancer imaging.</em>
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<span><span class="ref-journal">J Biomed Biotechnol. </span>2011;<span class="ref-vol">2011</span>:276907.</span> [<a href="/pmc/articles/PMC3085329/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3085329</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/21541217" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21541217</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="FPHCys18F.REF.2">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><dt>3.</dt><dd><div class="bk_ref" id="FPHCys18F.REF.3">la Fougere C., Suchorska B., Bartenstein P., Kreth F.W., Tonn J.C.
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<em>Molecular imaging of gliomas with PET: opportunities and limitations.</em>
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<span><span class="ref-journal">Neuro Oncol. </span>2011;<span class="ref-vol">13</span>(8):806–19.</span> [<a href="/pmc/articles/PMC3145468/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3145468</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/21757446" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21757446</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="FPHCys18F.REF.4">Bourdier T., Shepherd R., Berghofer P., Jackson T., Fookes C.J., Denoyer D., Dorow D.S., Greguric I., Gregoire M.C., Hicks R.J., Katsifis A.
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<em>Radiosynthesis and biological evaluation of L- and D-S-(3-[18F]fluoropropyl)homocysteine for tumor imaging using positron emission tomography.</em>
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<span><span class="ref-journal">J Med Chem. </span>2011;<span class="ref-vol">54</span>(6):1860–70.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21351733" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21351733</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="FPHCys18F.REF.5">Bourdier T., Fookes C.J.R., Pham T.Q., Greguric I., Katsifis A.
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<em>Synthesis and stability of S-(2-[18F]fluoroethyl)-L-homocysteine for potential tumour imaging.</em>
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<span><span class="ref-journal">Journal of Labelled Compounds and Radiopharmaceuticals. </span>2008;<span class="ref-vol">51</span>(11):369–373.</span></div></dd><dt>6.</dt><dd><div class="bk_ref" id="FPHCys18F.REF.6">Denoyer, D., L. Kirby, K. Waldeck, P. Roselt, O.C. Neels, T. Bourdier, R. Shepherd, A. Katsifis, and R.J. Hicks, <em>Preclinical characterization of (18)F-D-FPHCys, a new amino acid-based PET tracer.</em> Eur J Nucl Med Mol Imaging, 2011. [<a href="https://pubmed.ncbi.nlm.nih.gov/22160176" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 22160176</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: NBK65018</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/21994969" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">21994969</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/FDOPA/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CNPFH18F/" 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/NBK65018/?report=reader">PubReader</a></li><li><a href="/books/NBK65018/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK65018" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK65018" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. L- and D-S-(3-[18F]fluoropropyl)homocysteine. 2012 Jan 10 [Updated 2012 Feb 16]. 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/NBK65018/pdf/Bookshelf_NBK65018.pdf">PDF version of this page</a> (146K)</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="#FPHCys18F.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#FPHCys18F.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#FPHCys18F.In_Vitro_Studies_Testing_in_Ce" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#FPHCys18F.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#FPHCys18F.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#FPHCys18F.Supplemental_Information" ref="log$=inpage&link_id=inpage">Supplemental Information</a></li><li><a href="#FPHCys18F.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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