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<meta name="ncbi_db" content="books" /><meta name="ncbi_pdid" content="book-part" /><meta name="ncbi_acc" content="NBK51970" /><meta name="ncbi_domain" content="micad" /><meta name="ncbi_report" content="record" /><meta name="ncbi_type" content="fulltext" /><meta name="ncbi_objectid" content="" /><meta name="ncbi_pcid" content="/NBK51970/" /><meta name="ncbi_pagename" content="(R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf" /><meta name="ncbi_bookparttype" content="chapter" /><meta name="ncbi_app" content="bookshelf" />
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<title>(R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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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="(R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2011/02/10" /><meta name="citation_author" content="Kam Leung" /><meta name="citation_pmid" content="21328729" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK51970/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="(R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Kam Leung" /><meta name="DC.Date" content="2011/02/10" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK51970/" /><meta name="description" content="A variety of 11C- and 18F-labeled amino acids have been studied for potential use in positron emission tomography (PET) oncology (1, 2). Most brain tumors show an increased uptake of amino acids as compared with normal brain tissue (3). These amino acids are composed of naturally occurring amino acids, such as l-[11C]leucine, l-[11C]methionine, and l-[11C]tyrosine, and non-natural amino acids, such as [11C]aminoisobutyric acid, [11C]1-aminocyclopentane-1-carboxylic acid ([11C]ACPC), and [11C]1-aminocyclobutane-1-carboxylic acid. 123I-Labeled amino acids are also used in imaging in oncology (4-6). The natural amino acids are taken up by tumor cells through an energy-independent l-type amino acid transporter system and retained in tumor cells because of their higher than normal metabolic pathways, including incorporation into proteins (4). l-[11C]Methionine and [18F]fluorotyrosine have been widely used in the detection of tumors, but are not approved by the FDA. On the other hand, the non-natural amino acids are not metabolized but are taken up through both the l-type transporter and the energy-dependent A-type transporter (7). Therefore, they can accumulate intracellularly in high concentrations. In this chapter, (R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid (anti-2-[18F]FACPC), a fluorinated analog of [11C]ACPC, was shown to have a high tumor/brain ratio in mice (8). However, anti-2-[18F]FACPC exhibited unfavorable imaging characteristics for detection of pelvic recurrent prostate carcinoma in five patients because of high blood level at 5 min and high urinary bladder level at 20 min (9)." /><meta name="og:title" content="(R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid" /><meta name="og:type" content="book" /><meta name="og:description" content="A variety of 11C- and 18F-labeled amino acids have been studied for potential use in positron emission tomography (PET) oncology (1, 2). Most brain tumors show an increased uptake of amino acids as compared with normal brain tissue (3). These amino acids are composed of naturally occurring amino acids, such as l-[11C]leucine, l-[11C]methionine, and l-[11C]tyrosine, and non-natural amino acids, such as [11C]aminoisobutyric acid, [11C]1-aminocyclopentane-1-carboxylic acid ([11C]ACPC), and [11C]1-aminocyclobutane-1-carboxylic acid. 123I-Labeled amino acids are also used in imaging in oncology (4-6). The natural amino acids are taken up by tumor cells through an energy-independent l-type amino acid transporter system and retained in tumor cells because of their higher than normal metabolic pathways, including incorporation into proteins (4). l-[11C]Methionine and [18F]fluorotyrosine have been widely used in the detection of tumors, but are not approved by the FDA. On the other hand, the non-natural amino acids are not metabolized but are taken up through both the l-type transporter and the energy-dependent A-type transporter (7). Therefore, they can accumulate intracellularly in high concentrations. In this chapter, (R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid (anti-2-[18F]FACPC), a fluorinated analog of [11C]ACPC, was shown to have a high tumor/brain ratio in mice (8). However, anti-2-[18F]FACPC exhibited unfavorable imaging characteristics for detection of pelvic recurrent prostate carcinoma in five patients because of high blood level at 5 min and high urinary bladder level at 20 min (9)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK51970/" /><meta name="og:site_name" content="NCBI Bookshelf" /><meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" /><meta name="twitter:card" content="summary" /><meta name="twitter:site" content="@ncbibooks" /><meta name="bk-non-canon-loc" content="/books/n/micad/FACPC18F/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK51970/" /><link rel="stylesheet" href="/corehtml/pmc/css/figpopup.css" type="text/css" media="screen" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_print.min.css" type="text/css" media="print" /><style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} .body-content h2, .body-content .h2 {border-bottom: 1px solid #97B0C8} .body-content h2.inline {border-bottom: none} a.page-toc-label , .jig-ncbismoothscroll a {text-decoration:none;border:0 !important} .temp-labeled-list .graphic {display:inline-block !important} .temp-labeled-list img{width:100%}</style><script type="text/javascript" src="/corehtml/pmc/js/jquery.hoverIntent.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/common.min.js?_=3.18"> </script><script type="text/javascript" src="/corehtml/pmc/js/large-obj-scrollbars.min.js"> </script><script type="text/javascript">window.name="mainwindow";</script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/book-toc.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/books.min.js"> </script><meta name="book-collection" content="NONE" />
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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="#__NBK51970_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK51970_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/FPPAT18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MMP-1f18F/" 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="_NBK51970_"><span class="title" itemprop="name"><i>(R,S)-anti</i>-1-Amino-2-[<sup>18</sup>F]fluorocyclopentyl-1-carboxylic acid</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"><i>anti</i>-2-[<sup>18</sup>F]FACPC</div><p class="contrib-group"><span itemprop="author">Kam Leung</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK51970_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK51970_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kam Leung</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH, Bethesda, MD<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a></div></div><div class="small">Corresponding author.</div></div></div><p class="small">Created: <span itemprop="datePublished">November 18, 2010</span>; Last Update: <span itemprop="dateModified">February 10, 2011</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="FACPC18F.T.nc_chemical_namersanti1amino2" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK51970/table/FACPC18F.T.nc_chemical_namersanti1amino2/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__FACPC18F.T.nc_chemical_namersanti1amino2_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;"><i>(R,S)-anti</i>-1-Amino-2-[<sup>18</sup>F]fluorocyclopentyl-1-carboxylic acid</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/104170237" 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=104170237" alt="image 104170237 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;"><i>anti</i>-2-[<sup>18</sup>F]FACPC, [<sup>18</sup>F]FACPC</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;"><span class="small-caps">L</span>-type and A-type amino acid transporters</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;">Amino acid transporters</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Positron emission tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>18</sup>F</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><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><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Humans
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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="FACPC18F.Background"><h2 id="_FACPC18F_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=facpc%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>A variety of <sup>11</sup>C- and <sup>18</sup>F-labeled amino acids have been studied for potential use in positron emission tomography (PET) oncology (<a class="bk_pop" href="#FACPC18F.REF.1" data-bk-pop-others="FACPC18F.REF.2">1, 2</a>). Most brain tumors show an increased uptake of amino acids as compared with normal brain tissue (<a class="bk_pop" href="#FACPC18F.REF.3">3</a>). These amino acids are composed of naturally occurring amino acids, such as <span class="small-caps">l</span>-[<sup>11</sup>C]leucine, <span class="small-caps">l</span>-[<sup>11</sup>C]methionine, and <span class="small-caps">l</span>-[<sup>11</sup>C]tyrosine, and non-natural amino acids, such as [<sup>11</sup>C]aminoisobutyric acid, [<sup>11</sup>C]1-aminocyclopentane-1-carboxylic acid ([<sup>11</sup>C]ACPC), and [<sup>11</sup>C]1-aminocyclobutane-1-carboxylic acid. <sup>123</sup>I-Labeled amino acids are also used in imaging in oncology (<a class="bk_pop" href="#FACPC18F.REF.4" data-bk-pop-others="FACPC18F.REF.5 FACPC18F.REF.6">4-6</a>). The natural amino acids are taken up by tumor cells through an energy-independent <span class="small-caps">l</span>-type amino acid transporter system and retained in tumor cells because of their higher than normal metabolic pathways, including incorporation into proteins (<a class="bk_pop" href="#FACPC18F.REF.4">4</a>). <a href="/books/bv.fcgi?rid=micad.chapter.MET11C" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"><span class="small-caps">l</span>-[<sup>11</sup>C]Methionine</a> and <a href="/books/bv.fcgi?rid=micad.chapter.FMT18F" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">[<sup>18</sup>F]fluorotyrosine</a> have been widely used in the detection of tumors, but are not approved by the FDA. On the other hand, the non-natural amino acids are not metabolized but are taken up through both the <span class="small-caps">l</span>-type transporter and the energy-dependent A-type transporter (<a class="bk_pop" href="#FACPC18F.REF.7">7</a>). Therefore, they can accumulate intracellularly in high concentrations. In this chapter, <i>(R,S)-anti</i>-1-Amino-2-[<sup>18</sup>F]fluorocyclopentyl-1-carboxylic acid (<i>anti</i>-2-[<sup>18</sup>F]FACPC), a fluorinated analog of [<sup>11</sup>C]ACPC, was shown to have a high tumor/brain ratio in mice (<a class="bk_pop" href="#FACPC18F.REF.8">8</a>). However, <i>anti</i>-2-[<sup>18</sup>F]FACPC exhibited unfavorable imaging characteristics for detection of pelvic recurrent prostate carcinoma in five patients because of high blood level at 5 min and high urinary bladder level at 20 min (<a class="bk_pop" href="#FACPC18F.REF.9">9</a>).</p><div id="FACPC18F.Related_Resource_Links"><h3>Related Resource Links:</h3><ul><li class="half_rhythm"><div>
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<a href="/sites/entrez?Db=books&Cmd=DetailsSearch&Term=amino%20acid%20(transporter%20OR%20transporters)+AND+micad%5Bbook%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Chapters in MICAD</a>
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</div></li><li class="half_rhythm"><div>Gene information in NCBI (<a href="/gene/23428" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">L-type amino acid transporter</a>, <a href="/gene/54407" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">A-type amino acid transporter</a>)</div></li><li class="half_rhythm"><div>Articles in Online Mendelian Inheritance in Man <b>(</b>OMIM) (<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>)</div></li><li class="half_rhythm"><div>Clinical trials (<a href="http://www.clinicaltrials.gov/ct2/results?term=amino+acid+transporters" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporters</a>)</div></li><li class="half_rhythm"><div>Drug information in FDA (<a href="http://google2.fda.gov/search?q=amino+acid+transporters&client=FDAgov&site=FDAgov&lr=&proxystylesheet=FDAgov&output=xml_no_dtd&getfields=*&x=13&y=15" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporters</a>)</div></li></ul></div></div><div id="FACPC18F.Synthesis"><h2 id="_FACPC18F_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=FACPC+and+synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Nucleophilic fluorination of <i>syn</i>-3-(<i>N</i>-(tert-butoxycarbonyl)amino)-4-cyclopentane-1,2,3-oxathiazolidine-4-carboxylic acid tert-butyl ester 2,2-dioxide with K[<sup>18</sup>F]F/Kryptofix2.2.2 was performed for 10 min at 110°C (<a class="bk_pop" href="#FACPC18F.REF.8">8</a>). Subsequent acid hydrolysis for 10 min at 110°C and purification provided a radiosynthesis yield of 39 ± 8% (decay-corrected, <i>n</i> = 4) of <i>anti</i>-2-[<sup>18</sup>F]FACPC at the end of synthesis. A radiochemical purity of 99% was obtained. The total synthesis time was 60 min from the end of bombardment. The specific activity of <i>anti</i>-2-[<sup>18</sup>F]FACPC was not reported.</p></div><div id="FACPC18F.In_Vitro_Studies_Testing_in_Cel"><h2 id="_FACPC18F_In_Vitro_Studies_Testing_in_Cel_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=FACPC+and+in+vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><i>anti</i>-2-[<sup>18</sup>F]FACPC showed a fast uptake into rat 9L gliosarcoma tumor cells in culture with 6.33 ± 0.47% injected dose (<a class="bk_pop" href="#FACPC18F.REF.10">10</a>)/5 × 10<sup>5</sup> cells (<i>n</i> = 3) at 30 min of incubation (<a class="bk_pop" href="#FACPC18F.REF.8">8</a>). The uptake was reduced by 71%, 38%, and 65% by the presence of 10 mM 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid (<span class="small-caps">l</span>-type transporter inhibitor), <i>N</i>-methyl-α-aminoisobutyric acid (A-type transporter inhibitor), and a mixture of alanine, cysteine, and serine (ACS), respectively. The data suggest that <i>anti</i>-2-[<sup>18</sup>F]FACPC is a predominantly <span class="small-caps">l</span>-type transporter substrate with some affinity to the A-type transporter.</p></div><div id="FACPC18F.Animal_Studies"><h2 id="_FACPC18F_Animal_Studies_">Animal Studies</h2><div id="FACPC18F.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=FACPC+and+rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><i>Ex vivo</i> biodistribution studies of <i>anti</i>-2-[<sup>18</sup>F]FACPC were performed in rats (<i>n</i> = 5/group) implanted intracerebrally with 9L gliosarcoma (<a class="bk_pop" href="#FACPC18F.REF.8">8</a>). Accumulation of <i>anti</i>-2-[<sup>18</sup>F]FACPC in the tumors was 0.57, 1.68, 1.24, and 0.98% ID/g at 15, 30, 60, and 120 min after injection, respectively. The accumulation in the contralateral brain tissue was ~0.11% ID/g at these time points. The tissue with the highest accumulation at 30 min after injection was the kidney (3.44% ID/g), followed by the pancreas (2.91% ID/g), lung (1.13% ID/g), and liver (0.63% ID/g). The accumulation in other tissues (heart, spleen, muscle, bone) was low (<0.5% ID/g). The tumor/brain and tumor/muscle ratios were 10–13 and ~5 at 30 min and 120 min, respectively. [<sup>18</sup>F]FDG exhibited a tumor/brain ratio of 0.84 at 60 min in the same tumor model (<a class="bk_pop" href="#FACPC18F.REF.11">11</a>). No blocking studies were performed.</p></div><div id="FACPC18F.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=FACPC+and+(dog+or+pig+or+sheep+or+rabbit)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FACPC18F.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=FACPC+and+(primate+not+human)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="FACPC18F.Human_Studies"><h2 id="_FACPC18F_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=facpc%5BAll%20Fields%5D%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Savir-Baruch et al. (<a class="bk_pop" href="#FACPC18F.REF.9">9</a>) studied five patients with elevated PSA after curative therapy for prostate carcinoma underwent 60-min dynamic PET/CT of the pelvis after injection of 193-340 MBq (5.2-9.3 mCi) <i>anti</i>-2-[<sup>18</sup>F]FACPC. Average standard uptake value (SUV) of malignant lesions was 4.1 ± 1.3 and 2.6 ± 1.0 at 5 and 20 min, respectively. The lesion/blood ratios were 1.4 ± 0.5 at 5 min, whereas lesions/urinary bladder ratio was 0.3 ± 0.8 at 20 min. It was concluded that <i>anti</i>-2-[<sup>18</sup>F]FACPC exhibited unfavorable imaging characteristics for detection of pelvic recurrent prostate carcinoma because of high blood level at 5 min and high urinary bladder level at 20 min. On the other hand, <i>anti</i>-[<sup>18</sup>F]FACBC exhibited the lesion/blood and lesion/urinary bladder ratios of 3.0 ± 0.9 at 5 min and 2.3 ± 1.4 at 20 min, respectively.</p></div><div id="FACPC18F.NIH_Support"><h2 id="_FACPC18F_NIH_Support_">NIH Support</h2><p>R01 CA129356</p></div><div id="FACPC18F.References"><h2 id="_FACPC18F_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="FACPC18F.REF.1">Coleman R.E., Hoffman J.M., Hanson M.W., Sostman H.D., Schold S.C.
|
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<em>Clinical application of PET for the evaluation of brain tumors.</em>
|
||
<span><span class="ref-journal">J Nucl Med. </span>1991;<span class="ref-vol">32</span>(4):616–22.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2013802" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2013802</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="FACPC18F.REF.2">Kaschten B., Stevenaert A., Sadzot B., Deprez M., Degueldre C., Del Fiore G., Luxen A., Reznik M.
|
||
<em>Preoperative evaluation of 54 gliomas by PET with fluorine-18-fluorodeoxyglucose and/or carbon-11-methionine.</em>
|
||
<span><span class="ref-journal">J Nucl Med. </span>1998;<span class="ref-vol">39</span>(5):778–85.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9591574" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9591574</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="FACPC18F.REF.3">Herholz K., Heiss W.D.
|
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<em>Positron emission tomography in clinical neurology.</em>
|
||
<span><span class="ref-journal">Mol Imaging Biol. </span>2004;<span class="ref-vol">6</span>(4):239–69.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15262239" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15262239</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="FACPC18F.REF.4">Jager P.L., Vaalburg W., Pruim J., de Vries E.G., Langen K.J., Piers D.A.
|
||
<em>Radiolabeled amino acids: basic aspects and clinical applications in oncology.</em>
|
||
<span><span class="ref-journal">J Nucl Med. </span>2001;<span class="ref-vol">42</span>(3):432–45.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11337520" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11337520</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="FACPC18F.REF.5">Langen K.J., Pauleit D., Coenen H.H.
|
||
<em>3-[(123)I]Iodo-alpha-methyl-L-tyrosine: uptake mechanisms and clinical applications.</em>
|
||
<span><span class="ref-journal">Nucl Med Biol. </span>2002;<span class="ref-vol">29</span>(6):625–31.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12234586" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12234586</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="FACPC18F.REF.6">Lahoutte T., Caveliers V., Camargo S.M., Franca R., Ramadan T., Veljkovic E., Mertens J., Bossuyt A., Verrey F.
|
||
<em>SPECT and PET amino acid tracer influx via system L (h4F2hc-hLAT1) and its transstimulation.</em>
|
||
<span><span class="ref-journal">J Nucl Med. </span>2004;<span class="ref-vol">45</span>(9):1591–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15347729" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15347729</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="FACPC18F.REF.7">Palacin M., Estevez R., Bertran J., Zorzano A.
|
||
<em>Molecular biology of mammalian plasma membrane amino acid transporters.</em>
|
||
<span><span class="ref-journal">Physiol Rev. </span>1998;<span class="ref-vol">78</span>(4):969–1054.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9790568" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9790568</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="FACPC18F.REF.8">Jarkas N., Voll R.J., Williams L., Camp V.M., Goodman M.M.
|
||
<em>(R,S)-anti-1-amino-2-[18F]fluorocyclopentyl-1-carboxylic acid: synthesis from racemic 2-benzyloxycyclopentanone and biological evaluation for brain tumor imaging with positron emission tomography.</em>
|
||
<span><span class="ref-journal">J Med Chem. </span>2010;<span class="ref-vol">53</span>(18):6603–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/20718421" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20718421</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="FACPC18F.REF.9">Savir-Baruch, B., D.M. Schuster, N. Jarkas, V.A. Master, P.T. Nieh, R.K. Halkar, J.A. Nye, M.M. Lewis, R.J. Crowe, R.J. Voll, V.M. Camp, L.M. Bellamy, D.L. Roberts, and M.M. Goodman, <em>Pilot Evaluation of Anti-1-amino-2-[(18)F] fluorocyclopentane-1-carboxylic acid (anti-2-[(18)F] FACPC) PET-CT in Recurrent Prostate Carcinoma.</em> Mol Imaging Biol, 2010. [<a href="/pmc/articles/PMC3139806/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3139806</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20976627" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20976627</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="FACPC18F.REF.10">Oka S., Hattori R., Kurosaki F., Toyama M., Williams L.A., Yu W., Votaw J.R., Yoshida Y., Goodman M.M., Ito O.
|
||
<em>A preliminary study of anti-1-amino-3-18F-fluorocyclobutyl-1-carboxylic acid for the detection of prostate cancer.</em>
|
||
<span><span class="ref-journal">J Nucl Med. </span>2007;<span class="ref-vol">48</span>(1):46–55.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17204698" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17204698</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="FACPC18F.REF.11">Shoup T.M., Olson J., Hoffman J.M., Votaw J., Eshima D., Eshima L., Camp V.M., Stabin M., Votaw D., Goodman M.M.
|
||
<em>Synthesis and evaluation of [18F]1-amino-3-fluorocyclobutane-1-carboxylic acid to image brain tumors.</em>
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||
<span><span class="ref-journal">J Nucl Med. </span>1999;<span class="ref-vol">40</span>(2):331–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10025843" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10025843</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: NBK51970</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/21328729" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">21328729</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/FPPAT18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MMP-1f18F/" 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/NBK51970/?report=reader">PubReader</a></li><li><a href="/books/NBK51970/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK51970" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK51970" style="display:none" title="Cite this Page"><div class="bk_tt">Leung K. (R,S)-anti-1-Amino-2-[18F]fluorocyclopentyl-1-carboxylic acid. 2010 Nov 18 [Updated 2011 Feb 10]. 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/NBK51970/pdf/Bookshelf_NBK51970.pdf">PDF version of this page</a> (148K)</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="#FACPC18F.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#FACPC18F.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#FACPC18F.In_Vitro_Studies_Testing_in_Cel" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#FACPC18F.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#FACPC18F.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#FACPC18F.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#FACPC18F.References" ref="log$=inpage&link_id=inpage">References</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Search MICAD</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="source-application" id="Shutter"></a></div><div class="portlet_content"><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmSearch" method="get" action="/books/NBK5330/" id="frmSearch"><script type="text/javascript" src="/corehtml/pmc//js/bookshelf/micad.js">/**/</script><label class="offscreen_noflow" for="txtfield">Search term</label><input id="txtfield" type="text" name="f1_term" size="22" onKeyPress="KeyPress('micad',event,'/books/NBK5330/','')" /><button name="f1_search" type="submit">Go</button><button onclick="this.form.reset();" type="reset">Clear</button><p><b>Limit my Search:</b></p><div class="clearfix"><label for="detection">Method of detection:</label><div class="right"><select name="detection" id="detection" style="width:200px"><option value="" selected="selected">Any</option><option value="(MRI OR "Magnetic resonance imaging" OR MRS)">MRI</option><option value="Multimodal">Multimodal imaging</option><option value="Optical">Optical imaging</option><option value="PET">PET</option><option value="Photoacoustic">Photoacoustic imaging</option><option value="(SPECT OR planar)">SPECT</option><option value="Ultrasound">Ultrasound</option><option value="(x-ray OR ct)">X-ray, CT</option></select></div></div><div class="clearfix"><label for="signal">Source of signal/contrast:</label><div class="right"><select name="signal" id="signal" style="width:200px"><option value="" selected="selected">Any</option><optgroup label="MRI agents"><option value="(Copper OR Cu)">Copper</option><option value="(Europium OR Eu3+)">Europium</option><option value="(Fluorine OR 19F)">Fluorine</option><option value="(Gadolinium OR Gd3+)">Gadolinium</option><option value=""Hyperpolarized 13C"">Hyperpolarized 13C</option><option value=""Iron oxide"">Iron oxide</option><option value=""Nitroxide radicals"">Nitroxide radicals</option><option value="(Oxygen OR 17O)">Oxygen</option><option value="Thulium">Thulium</option></optgroup><optgroup label="Multimodal agents"><option value="((Gadolinium OR Gd3+) AND Optical)">Gadolinium and optical</option><option value="((Gadolinium OR Gd3+) AND (Gold OR Au))">Gadolinium and Gold</option><option value="("Iron oxide" AND (64Cu OR 124I OR 111In))">Iron oxide and
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europium</option><option value="(166Ho OR 67Ga OR 68Ga OR 123I OR 124I OR 125I)">Radionuclides</option></optgroup><optgroup label="Optical agents"><option value="("Fluorescent dyes" OR protein)">Fluorescent dyes or proteins</option><option value=""Luminescent agents"">Luminescent agents</option><option value="(Metals OR Metal OR Gold OR Au)">Metals (Au)</option><option value="Nanotubes">Nanotubes</option><option value=""Quantum dots"">Quantum dots</option></optgroup><optgroup label="PET radionuclides"><option value="("Arsenic 74" OR 74As)">Arsenic-74</option><option value="("Bromine 76" OR 76Br)">Bromine-76</option><option value="("Carbon 11" OR 11C)">Carbon-11</option><option value="(Copper-60 OR Copper-61 OR Copper-62 OR Copper-64 OR 60Cu OR 61Cu OR 62Cu OR 64Cu)">Copper-60, 61, 62, 64</option><option value="("Fluorine 18" OR 18F)">Fluorine-18</option><option value="(Gallium-68 OR 68Ga)">Gallium-68</option><option value="("Iodine 124" OR 124I)">Iodine-124</option><option 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value="Nanobubbles">Nanobubbles</option></optgroup><optgroup label="X-ray and CT agents"><option value="(Bismuth OR Bi)">Bismuth</option><option value="(Gold OR Au)">Gold</option><option value="Iodine">Iodine</option></optgroup></select></div></div><div class="clearfix"><label for="agent">Agent Category:</label><div class="right"><select name="agent" id="agent" style="width:200px"><option value="" selected="selected">Any</option><option value="(antibody OR trastuzumab OR immunoglobulin)">Antibodies</option><option value="(bacteria OR bacteriophage OR coli)">Bacteria</option><option value="cell">Cells</option><option value="(compound OR "amino acid" OR "folic acid" OR "cage molecule" OR carbohydrate OR copolymers OR polymer OR "small molecule" OR macromolecule OR triiodobenzoate OR estradiol OR glycosaminoglycan)">Compounds</option><option value="ligand">Ligands</option><option value="(lipid OR liposome OR liposomes">Lipids</option><option value="metal">Metal</option><option value="(nanoparticle OR nanoparticles OR nanotubes OR "iron oxide")">Nanoparticles</option><option value="(siRNA OR "nucleic acid" OR oligonucleotide)">Nucleic acids</option><option value="peptide">Peptides</option><option value="polyeptide">Polyeptides</option><option value="(protein OR albumin OR chemokin OR immunoprotein OR luciferase OR albumin)">Proteins</option><option value="(virus OR adenovirus)">Viruses</option></select></div></div><div class="clearfix"><label for="target">Target Category:</label><div class="right"><select name="target" id="target" style="width:200px"><option value="" selected="selected">Any</option><option value="acceptor">Acceptors</option><option value=""adhesion molecule"">Adhesion molecules</option><option value="(antigen OR antibody-antigen)">Antigens</option><option value="(enzyme OR enzymes OR enzyme-substrate)">Enzymes</option><option value="(lipids OR lipophilic cation)">Lipids</option><option value="(receptor OR receptors OR receptor-ligand OR 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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> anti-1-Amino-2-[(18)F]fluorocyclobutane-1-carboxylic acid.</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> anti-1-Amino-2-[(18)F]fluorocyclobutane-1-carboxylic acid.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Leung K. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/21328730" 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