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<title>2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(4-[18F]-fluorophenyl)carbonylamino] carbamoyl}butanoic 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="2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(4-[18F]-fluorophenyl)carbonylamino] carbamoyl}butanoic acid" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2011/12/26" /><meta name="citation_author" content="Arvind Chopra" /><meta name="citation_pmid" content="22238799" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK83149/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(4-[18F]-fluorophenyl)carbonylamino] carbamoyl}butanoic acid" /><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="2011/12/26" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK83149/" /><meta name="description" content="Folic acid (FA; also known as folate or vitamin B9) is a water-soluble vitamin that is required for the synthesis and repair of cellular DNA. FA also acts as a cofactor for many biological reactions and has an important role in cell maintenance and proliferation. Although the folate receptor (FR) is expressed at low levels in normal cells, this receptor is known to be upregulated in cancers such as those of the ovary, lung, breast, brain, colon, and the hematopoietic lineage cells (1). Therefore, the FR system has been targeted with radiolabeled folate and its derivatives, such as 67Ga-deferoxamine (DF)-folate, 111In-diethylenetriamine pentaacetic acid-folate, 99mTc-mercaptoacetyldiglycine-folate-methotrexate, etc., for the noninvasive detection of malignancies with single-photon emission computed tomography (2). Mathias et al. showed that 66/67Ga-DF-folate can be used with positron emission tomography (PET) for the imaging of FR-positive cancerous tumors in mice (3). However, although these tracers could detect the FR-rich tumors, they were deemed unsuitable for imaging lesions in the abdominal regions because high levels of radioactivity were observed to accumulate in the liver and intestines of the animals (4). In addition, 66/67Ga-labeled tracers are known to produce low-resolution images because they generate high positron energy (4.15 MeV and 1.89 MeV for 66Ga and 67Ga, respectively. 67Ga-labeled agents are used for single photon emission computed tomography imaging) compared to 18F (0.64 MeV), which generates superior images and is often used to radiolabel PET imaging agents in the clinic (4). In another study, it was shown that 18F-fluorobenzylamine derivatives of folate could detect tumors that had a high expression of FR, but the radioactivity from these labeled compounds accumulated mainly at the rim of the tumor, and large amounts of the label were retained in the liver and intestines of the animals (4, 5)." /><meta name="og:title" content="2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(4-[18F]-fluorophenyl)carbonylamino] carbamoyl}butanoic acid" /><meta name="og:type" content="book" /><meta name="og:description" content="Folic acid (FA; also known as folate or vitamin B9) is a water-soluble vitamin that is required for the synthesis and repair of cellular DNA. FA also acts as a cofactor for many biological reactions and has an important role in cell maintenance and proliferation. Although the folate receptor (FR) is expressed at low levels in normal cells, this receptor is known to be upregulated in cancers such as those of the ovary, lung, breast, brain, colon, and the hematopoietic lineage cells (1). Therefore, the FR system has been targeted with radiolabeled folate and its derivatives, such as 67Ga-deferoxamine (DF)-folate, 111In-diethylenetriamine pentaacetic acid-folate, 99mTc-mercaptoacetyldiglycine-folate-methotrexate, etc., for the noninvasive detection of malignancies with single-photon emission computed tomography (2). Mathias et al. showed that 66/67Ga-DF-folate can be used with positron emission tomography (PET) for the imaging of FR-positive cancerous tumors in mice (3). However, although these tracers could detect the FR-rich tumors, they were deemed unsuitable for imaging lesions in the abdominal regions because high levels of radioactivity were observed to accumulate in the liver and intestines of the animals (4). In addition, 66/67Ga-labeled tracers are known to produce low-resolution images because they generate high positron energy (4.15 MeV and 1.89 MeV for 66Ga and 67Ga, respectively. 67Ga-labeled agents are used for single photon emission computed tomography imaging) compared to 18F (0.64 MeV), which generates superior images and is often used to radiolabel PET imaging agents in the clinic (4). In another study, it was shown that 18F-fluorobenzylamine derivatives of folate could detect tumors that had a high expression of FR, but the radioactivity from these labeled compounds accumulated mainly at the rim of the tumor, and large amounts of the label were retained in the liver and intestines of the animals (4, 5)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK83149/" /><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/Folate118F/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK83149/" /><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="#__NBK83149_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK83149_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/Folate218F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Nifene18F/" 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="_NBK83149_"><span class="title" itemprop="name">2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{<i>N</i>-[(4-[<sup>18</sup>F]-fluorophenyl)carbonylamino] carbamoyl}butanoic acid</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"> [<sup>18</sup>F]-Folate-1</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK83149_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK83149_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">November 16, 2011</span>; Last Update: <span itemprop="dateModified">December 26, 2011</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="Folate118F.T.nc_chemical_name242amino4ox" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK83149/table/Folate118F.T.nc_chemical_name242amino4ox/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Folate118F.T.nc_chemical_name242amino4ox_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Chemical name:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">2-[(4-{[(2-Amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{<i>N</i>-[(4-[<sup>18</sup>F]fluorophenyl)carbonylamino] carbamoyl}butanoic acid</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/131466117" 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=131466117" alt="image 131466117 in the ncbi pubchem database" /></a>
|
||
</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Abbreviated name:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]-Folate-1<br /></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Synonym:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]-4-fluorobenzenecarbohydrazide-folate; [<sup>18</sup>F]-1; [<sup>18</sup>F]-<b>6</b></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Agent Category:</b>
|
||
</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;">
|
||
<b>Target:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Folate receptor</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Target Category:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Receptor</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Method of detection:</b>
|
||
</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;">
|
||
<b>Source of signal / contrast:</b>
|
||
</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;">
|
||
<b>Activation:</b>
|
||
</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;">
|
||
<b>Studies:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
|
||
<i>In vitro</i>
|
||
|
||
</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
|
||
</div></li></ul>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on above structure for 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="Folate118F.Background"><h2 id="_Folate118F_Background_">Background</h2><p>[<a href="/pubmed?term=folate%20receptor%20imaging&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Folic acid (FA; also known as folate or vitamin B<sub>9</sub>) is a water-soluble vitamin that is required for the synthesis and repair of cellular DNA. FA also acts as a cofactor for many biological reactions and has an important role in cell maintenance and proliferation. Although the folate receptor (FR) is expressed at low levels in normal cells, this receptor is known to be upregulated in cancers such as those of the ovary, lung, breast, brain, colon, and the hematopoietic lineage cells (<a class="bk_pop" href="#Folate118F.REF.1">1</a>). Therefore, the FR system has been targeted with radiolabeled folate and its derivatives, such as <sup>67</sup>Ga-deferoxamine (DF)-folate, <sup>111</sup>In-diethylenetriamine pentaacetic acid-folate, <sup>99m</sup>Tc-mercaptoacetyldiglycine-folate-methotrexate, etc., for the noninvasive detection of malignancies with single-photon emission computed tomography (<a class="bk_pop" href="#Folate118F.REF.2">2</a>). Mathias et al. showed that <sup>66/67</sup>Ga-DF-folate can be used with positron emission tomography (PET) for the imaging of FR-positive cancerous tumors in mice (<a class="bk_pop" href="#Folate118F.REF.3">3</a>). However, although these tracers could detect the FR-rich tumors, they were deemed unsuitable for imaging lesions in the abdominal regions because high levels of radioactivity were observed to accumulate in the liver and intestines of the animals (<a class="bk_pop" href="#Folate118F.REF.4">4</a>). In addition, <sup>66/67</sup>Ga-labeled tracers are known to produce low-resolution images because they generate high positron energy (4.15 MeV and 1.89 MeV for <sup>66</sup>Ga and <sup>67</sup>Ga, respectively. <sup>67</sup>Ga-labeled agents are used for single photon emission computed tomography imaging) compared to <sup>18</sup>F (0.64 MeV), which generates superior images and is often used to radiolabel PET imaging agents in the clinic (<a class="bk_pop" href="#Folate118F.REF.4">4</a>). In another study, it was shown that <sup>18</sup>F-fluorobenzylamine derivatives of folate could detect tumors that had a high expression of FR, but the radioactivity from these labeled compounds accumulated mainly at the rim of the tumor, and large amounts of the label were retained in the liver and intestines of the animals (<a class="bk_pop" href="#Folate118F.REF.4" data-bk-pop-others="Folate118F.REF.5">4, 5</a>).</p><p>In an ongoing effort to generate radiolabeled agents for the imaging of tumors that express high levels of FRs that would be superior to those developed and evaluated earlier, a <sup>18</sup>F-fluorobenzene derivative of folic acid ([<sup>18</sup>F]-folate-1), a pyridinecarbohydrazide-folate derivative of folic acid ([<sup>18</sup>F]-folate-2), a <sup>18</sup>F-fluorobenzene/<a href="http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=78794e3d-f293-4eeb-22ac-8f536d5947eb" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">methotrexate</a> (MTX) conjugate of folic acid ([<sup>18</sup>F]-folate-MTX-8), and a <sup>18</sup>F-pyridinecarbohydrazide-folate/methotrexate conjugate of folic acid ([<sup>18</sup>F]-folate-MTX-9) have been synthesized (<a class="bk_pop" href="#Folate118F.REF.2">2</a>). The biodistribution of these tracers was investigated in healthy mice. On the basis of results obtained from these studies, [<sup>18</sup>F]-folate-1 was evaluated for the PET imaging of human <a href="http://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CCL-17&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">KB cell line</a> xenograft tumors (have a high expression of FR) in mice. This chapter describes the results obtained with [<sup>18</sup>F]-folate-1. Separate chapters in MICAD (<a href="http://www.micad.nih.gov/" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">http://www.micad.nih.gov/</a>) discuss the studies performed with [<sup>18</sup>F]-folate-2 (<a class="bk_pop" href="#Folate118F.REF.6">6</a>), [<sup>18</sup>F]-folate-MTX-8 (<a class="bk_pop" href="#Folate118F.REF.7">7</a>), and [<sup>18</sup>F]-folate-MTX-9 (<a class="bk_pop" href="#Folate118F.REF.8">8</a>).</p><div id="Folate118F.Related_Resource_Links"><h3>Related Resource Links</h3><p>FR-related chapters in <a href="/books/?term=Folate+receptor+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>Adult human FR <a href="/nuccore/NM_016724.2" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">protein and mRNA sequences</a></p><p><a href="/gene/2348" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Human FR gene</a> (Gene ID: 2348)</p><p>FR <a href="http://clinicaltrials.gov/ct2/results?term=folate+receptor+AND+targeted+AND+cancer" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">clinical trials</a></p><p>FR in <a href="/omim/136430" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Online Mendelian Inheritance in Man (OMIM)</a> database</p><p>FR pathway in <a href="http://www.genome.jp/dbget-bin/www_bget?hsa:2348+hsa:2350+hsa:2352+hsa:390243" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Kyoto Encyclopedia of Genes and Genomes (KEGG)</a></p><p>Folic acid information on <a href="http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=ff80ef4d-e04c-9f83-2b56-cccc30028f72" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Dailymed site</a></p></div></div><div id="Folate118F.Synthesis"><h2 id="_Folate118F_Synthesis_">Synthesis</h2><p>[<a href="/pubmed?term=18F-F-1%20synthesis&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Folate-1 was synthesized with hydrazide-folate and 2,5-dioxoazolidinyl 4-fluorobenzoate in presence of triethylamine and the <sup>18</sup>F labeling of folate-1 has been detailed elsewhere (<a class="bk_pop" href="#Folate118F.REF.9">9</a>). The total time of synthesis was ~45 min, and the radiochemical yield and radiochemical purity of the final product were >80% (based on the initial <sup>18</sup>F concentration) and >97% (without high-performance liquid chromatographic purification), respectively. The specific activity of the final product was reported to be >11.11 MBq/μmol (300 mCi/μmol).</p></div><div id="Folate118F.In_Vitro_Studies_Testing_in_C"><h2 id="_Folate118F_In_Vitro_Studies_Testing_in_C_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed?term=18F-F-1%20in%20vitro&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Using an <i>n</i>-octanol-water mixture (pH 7.3), the partition coefficient of [<sup>18</sup>F]-folate-1 was determined to be 0.38 ± 0.02, indicating that the labeled compound had low lipophilicity (<a class="bk_pop" href="#Folate118F.REF.9">9</a>).</p><p>[<sup>18</sup>F]-Folate-1 was reported to be stable in human plasma for at least 4 h at 37°C (data not presented) (<a class="bk_pop" href="#Folate118F.REF.9">9</a>).</p><p>The FR binding affinity of [<sup>18</sup>F]-folate-1 was determined to be 13.08 ± 0.83 nM with a saturation assay using KB cell membranes (<a class="bk_pop" href="#Folate118F.REF.9">9</a>). A cell internalization assay of [<sup>18</sup>F]-folate-1 with KB cells (using an acidic buffer, pH not mentioned) showed that 25.85 ± 0.95% of the tracer was internalized by the cells within 20 min at 37°C.</p></div><div id="Folate118F.Animal_Studies"><h2 id="_Folate118F_Animal_Studies_">Animal Studies</h2><div id="Folate118F.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed?term=18F-F-1%20rodentia&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of [<sup>18</sup>F]-folate-1 was studied in normal Balb/c mice as described by al Jammaz et al. (<a class="bk_pop" href="#Folate118F.REF.2">2</a>). The animals (<i>n</i> = 4 mice/time point) were injected with 749 kBq (20 μCi) of the tracer through the tail vein and euthanized at 10, 60, and 120 min postinjection (p.i.) to determine the amount of radioactivity accumulated in the various organs. All data were presented as percent of injected dose per gram tissue (% ID/g). A rapid clearance of radioactivity from the blood was observed (4.41 ± 0.60% ID/g at 10 min p.i., 2.55 ± 1.50% ID/g at 60 min p.i., and 1.13 ± 0.51% ID/g at 120 min p.i.). High levels of the label were observed in the kidneys (22.50 ± 4.42% ID/g at 10 min p.i. and 17.88 ± 0.10% ID/g at 120 min p.i.) and the intestine (5.95 ± 2.11% ID/g at 10 min p.i. and 5.86 ± 0.26% ID/g at 120 min p.i.) of these animals. In the liver the amount of label decreased from 7.52 ± 1.43% ID/g at 10 min p.i. to 1.02 ± 0.61% ID/g at 60 min p.i. and to 0.32 ± 0.12% ID/g at 120 min p.i. indicating that the tracer was excreted through the urinary and the hepatobiliary routes. A similar trend of tracer uptake in the various organs was also observed with [<sup>18</sup>F]-folate-2 (for details, see Chopra (<a class="bk_pop" href="#Folate118F.REF.6">6</a>)).</p><p>The biodistribution of [<sup>18</sup>F]-folate-1 was also investigated in nude mice (<i>n</i> = 4 animals) bearing KB cell tumors. The animals were injected with the radiotracer as described above and euthanized at 60 min p.i (<a class="bk_pop" href="#Folate118F.REF.2">2</a>). The uptake of radioactivity in the various organs of the mice was similar to that observed earlier (see above), and the amount of label in the tumor was 5.94 ± 1.16% ID/g at 60 min p.i. The tumor/blood (T/B) and tumor/muscle (T/M) ratios at 60 min p.i. were 6.39 and 25.83, respectively. The T/B and T/M ratios at 60 min p.i. with [<sup>18</sup>F]-folate-2 were 14.70 and 28.70, respectively (see Chopra for details (<a class="bk_pop" href="#Folate118F.REF.6">6</a>)). For blocking studies, the mice were injected with 100 μg (0.22 μmol) FA 10 min before the administration of [<sup>18</sup>F]-folate-1, and the rodents were treated as described above (<a class="bk_pop" href="#Folate118F.REF.2">2</a>). Under these conditions, the uptake of radioactivity in the tumors was reduced significantly (0.74 ± 0.17% ID/g, <i>P</i> <0.05); the kidneys, liver, and intestines (among these organs only the kidneys and the liver have an above normal expression of the FR) also showed a significantly (<i>P</i> < 0.05) reduced accumulation of the label. With [<sup>18</sup>F]-folate-2, the uptake in the tumor at 60 min p.i. was reduced to 0.66 ± 0.10% ID/g, and the amount of label in the kidneys, liver, and intestines was also reduced significantly (<i>P</i> < 0.05). This indicated that both [<sup>18</sup>F]-folate-1 and [<sup>18</sup>F]-folate-2 had a high binding specificity for the FR.</p><p>
|
||
<b>Table: Tumor Uptake and Tumor/Blood and Tumor/Muscle Ratios of different </b>
|
||
<sup>
|
||
<b>18</b>
|
||
</sup>
|
||
<b>F-Labeled Folate</b>
|
||
</p><div id="Folate118F.T.nc_tracertumor_uptake__idgr" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK83149/table/Folate118F.T.nc_tracertumor_uptake__idgr/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Folate118F.T.nc_tracertumor_uptake__idgr_lrgtbl__"><table><tbody><tr><td rowspan="2" colspan="1" style="text-align:center;vertical-align:middle;">
|
||
<b>Tracer</b>
|
||
</td><td colspan="2" rowspan="1" style="text-align:center;vertical-align:top;">
|
||
<b>Tumor Uptake (% ID/g)</b>
|
||
</td><td colspan="2" rowspan="1" style="text-align:center;vertical-align:top;">
|
||
<b>Ratio (No Folate Pre-treatment)</b>
|
||
</td></tr><tr><td rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
||
<b>No Folate Pre-treatment</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
||
<b>With Folate (100 μg) Pre-treatment</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
||
<b>Tumor/blood</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
||
<b>Tumor/Muscle</b>
|
||
</td></tr><tr><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">
|
||
<b>[</b>
|
||
<sup>
|
||
<b>18</b>
|
||
</sup>
|
||
<b>F]-Folate-1</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">5.94 ± 1.16</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">0.74 ± 0.17</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">6.39</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">25.83</td></tr><tr><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">
|
||
<b>[</b>
|
||
<sup>
|
||
<b>18</b>
|
||
</sup>
|
||
<b>F]-Folate-2</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">5.74 ± 0.16</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">0.66 ± 0.10</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">14.72</td><td rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">28.70</td></tr></tbody></table></div></div><p>From this study, the investigators concluded that [<sup>18</sup>F]-folate-2 was probably superior to [<sup>18</sup>F]-folate-1 for the imaging of FR-rich tumors (<a class="bk_pop" href="#Folate118F.REF.2">2</a>).</p></div><div id="Folate118F.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed?term=18F-F-1%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="Folate118F.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed?term=18F-F-1%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="Folate118F.Human_Studies"><h2 id="_Folate118F_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed?term=18F-F-1%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="Folate118F.Supplemental_Information"><h2 id="_Folate118F_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="Folate118F.References"><h2 id="_Folate118F_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="Folate118F.REF.1">Xia W., Low P.S.
|
||
<em>Folate-targeted therapies for cancer.</em>
|
||
<span><span class="ref-journal">J Med Chem. </span>2010;<span class="ref-vol">53</span>(19):6811–24.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/20666486" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20666486</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="Folate118F.REF.2">Al Jammaz I., Al-Otaibi B., Amer S., Okarvi S.M.
|
||
<em>Rapid synthesis and in vitro and in vivo evaluation of folic acid derivatives labeled with fluorine-18 for PET imaging of folate receptor-positive tumors.</em>
|
||
<span><span class="ref-journal">Nucl Med Biol. </span>2011;<span class="ref-vol">38</span>(7):1019–28.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21982573" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21982573</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="Folate118F.REF.3">Mathias C.J., Lewis M.R., Reichert D.E., Laforest R., Sharp T.L., Lewis J.S., Yang Z.F., Waters D.J., Snyder P.W., Low P.S., Welch M.J., Green M.A.
|
||
<em>Preparation of 66Ga- and 68Ga-labeled Ga(III)-deferoxamine-folate as potential folate-receptor-targeted PET radiopharmaceuticals.</em>
|
||
<span><span class="ref-journal">Nucl Med Biol. </span>2003;<span class="ref-vol">30</span>(7):725–31.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14499330" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14499330</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="Folate118F.REF.4">Sega E.I., Low P.S.
|
||
<em>Tumor detection using folate receptor-targeted imaging agents.</em>
|
||
<span><span class="ref-journal">Cancer Metastasis Rev. </span>2008;<span class="ref-vol">27</span>(4):655–64.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18523731" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18523731</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="Folate118F.REF.5">Bettio A., Honer M., Muller C., Bruhlmeier M., Muller U., Schibli R., Groehn V., Schubiger A.P., Ametamey S.M.
|
||
<em>Synthesis and preclinical evaluation of a folic acid derivative labeled with 18F for PET imaging of folate receptor-positive tumors.</em>
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||
<span><span class="ref-journal">J Nucl Med. </span>2006;<span class="ref-vol">47</span>(7):1153–60.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16818950" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16818950</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="Folate118F.REF.6">Chopra, A., <em>2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(4-[18F]-fluorophenyl)carbonylamino] carbamoyl}butanoic acid.</em> Molecular Imaging and Contrast agent Database (MICAD) [database online]. National Library of Medicine, NCBI, Bethesda, MD, USA. Available from <a href="http://www.micad.nih.gov/" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">www<wbr style="display:inline-block"></wbr>.micad.nih.gov</a>, 2004 -to current. [<a href="https://pubmed.ncbi.nlm.nih.gov/22238799" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 22238799</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="Folate118F.REF.7">Chopra, A., <em>2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(2-[18F]-fluoro(4-pyridyl))carbonylamino] carbamoyl}butanoic acid.</em> Molecular Imaging and Contrast agent Database (MICAD) [database online]. National Library of Medicine, NCBI, Bethesda, MD, USA. Available from <a href="http://www.micad.nih.gov/" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">www<wbr style="display:inline-block"></wbr>.micad.nih.gov</a>, 2004 -to current. [<a href="https://pubmed.ncbi.nlm.nih.gov/22238794" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 22238794</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="Folate118F.REF.8">Chopra, A., <em>2-[18F]Fluoropyridine-4-carbohydrazide-methotrexate (9).</em> Molecular Imaging and Contrast agent Database (MICAD) [database online]. National Library of Medicine, NCBI, Bethesda, MD, USA. Available from <a href="http://www.micad.nih.gov/" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">www<wbr style="display:inline-block"></wbr>.micad.nih.gov</a>, 2004 -to current.</div></dd><dt>9.</dt><dd><div class="bk_ref" id="Folate118F.REF.9">Jammaz I.A., Otaibi B.A., Okarvi S., Amartey J.K.
|
||
<em>Novel synthesis of [18F]-fluorobenzene and pyridinecarbohydrazide-folates as potential PET radiopharmaceuticals.</em>
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<span><span class="ref-journal">Journal of Labelled Compounds and Radiopharmaceuticals. </span>2006;<span class="ref-vol">49</span>(2):125–37.</span></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: NBK83149</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/22238799" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">22238799</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/Folate218F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Nifene18F/" 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/NBK83149/?report=reader">PubReader</a></li><li><a href="/books/NBK83149/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK83149" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK83149" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. 2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(4-[18F]-fluorophenyl)carbonylamino] carbamoyl}butanoic acid. 2011 Nov 16 [Updated 2011 Dec 26]. 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/NBK83149/pdf/Bookshelf_NBK83149.pdf">PDF version of this page</a> (153K)</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="#Folate118F.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#Folate118F.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#Folate118F.In_Vitro_Studies_Testing_in_C" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#Folate118F.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#Folate118F.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#Folate118F.Supplemental_Information" ref="log$=inpage&link_id=inpage">Supplemental Information</a></li><li><a href="#Folate118F.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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/><label for="__micad_btn_6">Any</label></div></form><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmGo" method="get" action="javascript:alert('frmGo:_@action_was_not_set')" id="frmGo"><input name="term" value="." type="hidden" /></form></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Related information</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="discovery_db_links" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pcsubstance&DbFrom=books&Cmd=Link&LinkName=books_pcsubstance&IdsFromResult=2750796" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=2750796" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/22238794" ref="ordinalpos=1&linkpos=1&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> 2-[(4-{[(2-amino-4-oxohydropteridin-7yl)methyl]amino}phenyl) carbonylamino]-4-{N-[(2-[18F]-fluoro(4-pyridyl))carbonylamino] carbamoyl}butanoic acid.</a><span 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ref="ordinalpos=1&linkpos=4&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> [(149/152/155/161)Tb]-Labeled DOTA-folate conjugated to an albumin-binding entity.</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> [(149/152/155/161)Tb]-Labeled DOTA-folate conjugated to an albumin-binding entity.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Chopra A. </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 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