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<title>68Ga-Labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic 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="68Ga-Labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2011/10/12" /><meta name="citation_author" content="Liang Shan" /><meta name="citation_pmid" content="22013604" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK65093/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="68Ga-Labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Liang Shan" /><meta name="DC.Date" content="2011/10/12" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK65093/" /><meta name="description" content="The 68Ga-labeled â-aminoalanine, ã-aminohomoalanine, and å-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), abbreviated as 68Ga-2a, 68Ga-2b, and 68Ga-2c, respectively, were synthesized by Shetty et al. for positron emission tomography (PET) of tumors (1)." /><meta name="og:title" content="68Ga-Labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid" /><meta name="og:type" content="book" /><meta name="og:description" content="The 68Ga-labeled â-aminoalanine, ã-aminohomoalanine, and å-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), abbreviated as 68Ga-2a, 68Ga-2b, and 68Ga-2c, respectively, were synthesized by Shetty et al. for positron emission tomography (PET) of tumors (1)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK65093/" /><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/Ga68-2a-c/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK65093/" /><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="#__NBK65093_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK65093_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/GhrelinDer68Ga/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Ga68-1a-c/" 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="_NBK65093_"><span class="title" itemprop="name"><sup>68</sup>Ga-Labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"><sup>68</sup>Ga-2a-c</div><p class="contrib-group"><span itemprop="author">Liang Shan</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK65093_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK65093_ai__"><div class="contrib half_rhythm"><span itemprop="author">Liang Shan</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH<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">August 29, 2011</span>; Last Update: <span itemprop="dateModified">October 12, 2011</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="Ga68-2a-c.T.nc_chemical_name68galabeled_" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK65093/table/Ga68-2a-c.T.nc_chemical_name68galabeled_/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Ga68-2a-c.T.nc_chemical_name68galabeled__lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>68</sup>Ga-labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<span class="graphic"><img src="/books/NBK65093/bin/Ga682ac.jpg" alt="Image Ga682ac.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;"><sup>68</sup>Ga-2a-c</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Synonym:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>68</sup>Ga-2a, <sup>68</sup>Ga-2b, <sup>68</sup>Ga-2c</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;">Others (amino acid)</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;">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;">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 / contrast:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Gallium-68 (<sup>68</sup>Ga)</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;">Structure of 2a-c (<i>n</i> = 1, β-aminoalanine; <i>n</i> = 2, γ-aminohomoalanine; and <i>n</i> = 4, ε-aminolysine) by Shetty et al. (1).</td></tr></tbody></table></div></div><div id="Ga68-2a-c.Background"><h2 id="_Ga68-2a-c_Background_">Background</h2><p>[<a href="/pubmed?term=amino%20acid%20and%20imaging%20and%20amino%20acid%20transporters" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The <sup>68</sup>Ga-labeled â-aminoalanine, ã-aminohomoalanine, and å-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), abbreviated as <sup>68</sup>Ga-2a, <sup>68</sup>Ga-2b, and <sup>68</sup>Ga-2c, respectively, were synthesized by Shetty et al. for positron emission tomography (PET) of tumors (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>).</p><p>Radiolabeled amino acids represent a diverse class of tracers that target the increased amino acid transport in cancer cells (<a class="bk_pop" href="#Ga68-2a-c.REF.2" data-bk-pop-others="Ga68-2a-c.REF.3">2, 3</a>). To date, >20 distinct amino acid transporters have been identified in mammalian cells, and these transporters differ in terms of substrate specificity, tissue expression patterns, sodium and other ion dependence, pH sensitivity, and transport mechanism (<a class="bk_pop" href="#Ga68-2a-c.REF.4" data-bk-pop-others="Ga68-2a-c.REF.5">4, 5</a>). Because of increased demand for amino acids in malignant cells, some transporters have been shown to be overexpressed in different types of tumors, and the process of amino acid transport is relatively fast (<a class="bk_pop" href="#Ga68-2a-c.REF.1" data-bk-pop-others="Ga68-2a-c.REF.2 Ga68-2a-c.REF.6">1, 2, 6</a>). These features make tumor imaging with amino acid tracers possible within 20 min. Indeed, there is growing evidence that radiolabeled amino acids have the potential to overcome some of the limitations of 2-deoxy-2-[<sup>18</sup>F]fluoro-<span class="small-caps">d</span>-glucose ([<sup>18</sup>F]FDG) in tumor imaging, especially in the imaging of primary and recurrent brain tumors, neuroendocrine tumors, and prostate cancers (<a class="bk_pop" href="#Ga68-2a-c.REF.2" data-bk-pop-others="Ga68-2a-c.REF.3 Ga68-2a-c.REF.7">2, 3, 7</a>). Different studies also showed that radiotracers that target different amino acid transporters exhibit different imaging properties that may provide unique biological information of tumors (<a class="bk_pop" href="#Ga68-2a-c.REF.1" data-bk-pop-others="Ga68-2a-c.REF.2 Ga68-2a-c.REF.8">1, 2, 8</a>).</p><p>The first group of widely investigated amino acids is the analogs of phenylalanine and tyrosine (<a class="bk_pop" href="#Ga68-2a-c.REF.2" data-bk-pop-others="Ga68-2a-c.REF.3">2, 3</a>). Because of their bulky neutral side chains, these natural amino acids are the substrates of system L transporters and have been proven to be useful for tumor imaging, particularly for brain tumors. The limitation common to most of the natural amino acids is the susceptibility to <i>in vivo</i> metabolism, which decreases tumor specificity and complicates kinetic analysis. Because none of the natural amino acids contain fluorine or iodine, labeling with fluorine-18 or iodine-123 and retaining key biochemical properties are also challenging. These shortcomings associated with natural amino acids can be partially overcome by using non-natural amino acids. Typically, non-natural amino acids are neither metabolized nor readily incorporated into protein <i>in vivo</i> (<a class="bk_pop" href="#Ga68-2a-c.REF.1" data-bk-pop-others="Ga68-2a-c.REF.2 Ga68-2a-c.REF.3">1-3</a>). One group of non-natural amino acids is á,á-dialkyl amino acids, which are generated by substituting the á-carbon hydrogen of natural amino acids with a methyl group or other alkyl chains. These amino acids are primarily the substrates of system A transporters. The second group is alicyclic amino acids, which are á,á-dialkyl amino acids with side chains bonded covalently to each other to form a cyclic ring. These amino acids are the substrates of system L transporters. The third group is the non-natural proline derivatives, which exhibit different transport selectivity. One challenge in developing amino acid radiotracers is to overcome the low selectivity and the decreased recognition after radiolabeling to specific transporters (<a class="bk_pop" href="#Ga68-2a-c.REF.2" data-bk-pop-others="Ga68-2a-c.REF.3 Ga68-2a-c.REF.8">2, 3, 8</a>). Another challenge is the low uptake of amino acid agents in tumors, which leads to less sensitivity for tumor detection than with [<sup>18</sup>F]FDG (<a class="bk_pop" href="#Ga68-2a-c.REF.7">7</a>).</p><p>Shetty et al. synthesized a group of <sup>68</sup>Ga-labled alanine and lysine derivatives of DOTA, 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA), 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid (DO2A), and 1,4,7,10-tetraazacyclododecane-1,4,7,-triacetic acid (DO3A) (<a class="bk_pop" href="#Ga68-2a-c.REF.1" data-bk-pop-others="Ga68-2a-c.REF.8">1, 8</a>). The four bifunctional chelating agents have similar sizes, but they differ in the net charges and stability because of the different numbers of pendent carboxylate arms. The amino acids have been conjugated to one of the carboxylate arms, and the nitrogen atoms in the heterocyclic ring are presumed to coordinate with metals to form chelates. Biodistribution studies and PET imaging indicate the structure–activity relationship of the amino acid derivatives, and the selective uptakes of these compounds by different cancer tissues might provide an insight on the different modes of amino acid uptake by cancer cells (<a class="bk_pop" href="#Ga68-2a-c.REF.1" data-bk-pop-others="Ga68-2a-c.REF.8">1, 8</a>).</p><p>This chapter summarizes the data obtained with <sup>68</sup>Ga-labeled DOTA derivatives: <sup>68</sup>Ga-2a (<sup>68</sup>Ga-DOTA-â-aminoalanine), <sup>68</sup>Ga-2b (<sup>68</sup>Ga-DOTA-ã-aminohomoalanine), and <sup>68</sup>Ga-2c (<sup>68</sup>Ga-DOTA-å-aminolysine). These DOTA derivatives were comparatively analyzed with the corresponding NOTA derivatives (<sup>68</sup>Ga-1a, <sup>68</sup>Ga-1b, and <sup>68</sup>Ga-1c, respectively) (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>).</p><div id="Ga68-2a-c.Related_Resource_Links"><h3>Related Resource Links:</h3><p>
|
||
<a href="/books/?term=amino+acid+transporter+AND+micad%5bbook%5d&view=chapter&p%24a=&p%24l=PBooksLayout&p%24st=books" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporter-targeted imaging agents in MICAD</a>
|
||
</p><p>
|
||
<a href="/omim/?term=amino+acid+transporter" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporter articles in Online Mendelian Inheritance in Man (OMIM)</a>
|
||
</p><p>
|
||
<a href="http://clinicaltrials.gov/ct2/results?term=amino+acid+transporter" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporter related clinical trials in ClinicalTrials.gov</a>
|
||
</p><p>
|
||
<a href="/pcassay/?term=amino+acid+transporter" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Amino acid transporter related bioassays in PubChem BioAssay</a>
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</p></div></div><div id="Ga68-2a-c.Synthesis"><h2 id="_Ga68-2a-c_Synthesis_">Synthesis</h2><p>[<a href="/pubmed/20926300" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The protected â-amino-<span class="small-caps">l</span>-alanine was synthesized from <i>N</i>-<i>tert</i>-butyl-<span class="small-caps">l</span>-serine methyl ester. Conjugation of DOTA with protected â-amino-<span class="small-caps">l</span>-alanine was performed in aqueous solution using 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride as a coupling reagent to obtain the alanine conjugate. Hydrolysis of the protected esters using LiOH, followed by hydrochloric acid, resulted in the formation of compound 2a (DOTA-â-aminoalanine) as a hydrochloride salt.</p><p>The ã-amino-<span class="small-caps">l</span>-homoalanine was purchased, and the å-aminolysine was synthesized from <i>N</i><sup>á</sup>-boc-<i>N</i><sup>å</sup>-benzyloxycarbonyl-lysine by <i>tert</i>-butyl esterification and subsequent deprotection. Conjugation of ã-amino-<span class="small-caps">l</span>-homoalanine and å-aminolysine with DOTA was performed separately with <i>N</i>,<i>N</i>'-dicyclohexylcarbodiimide as a coupling agent and pyridine as a base. Further hydrolysis and deprotection resulted in the formation of compound 2b (DOTA-ã-aminohomoalanine) and compound 2c (DOTA-å-aminolysine), respectively. All final products were purified (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>).</p><p>The DOTA and NOTA derivatives were labeled with <sup>68</sup>Ga either in a boiling water bath or at room temperature (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>). The chelating agents, DOTA and NOTA, were also labeled with <sup>68</sup>Ga as controls for the <i>in vitro</i> protein binding and cell uptake studies. The labeling efficiency was >95% for all agents, and no free <sup>68</sup>Ga was found after purification. The specific activities of the purified agents were in the range 1.94–9.21 GBq/ìmol (52.43–248.92 mCi/µmol). Stability studies at room temperature confirmed the stability of all agents for >4 h.</p></div><div id="Ga68-2a-c.In_Vitro_Studies_Testing_in_Ce"><h2 id="_Ga68-2a-c_In_Vitro_Studies_Testing_in_Ce_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed/20926300" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Shetty et al. performed protein binding studies by incubating the agents with human serum at 37°C for 10 min and 1 h, respectively (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>). <sup>68</sup>Ga-2c showed the lowest level of protein binding (2.44% at 10 min and 5.57% at 1 h), followed by <sup>68</sup>Ga-2b (6.40% at 10 min and 6.60% at 1 h) and <sup>68</sup>Ga-2a (9.87% at 10 min and 9.81% at 1 h). In comparison with the corresponding NOTA derivatives, all DOTA derivatives had higher levels of serum protein binding. Only the DOTA derivatives showed significant increases in protein binding over time. Of all NOTA and DOTA derivatives, <sup>68</sup>Ga-1b showed the lowest level of protein binding (1.71% at 10 min and 1.44% at 1 h) and <sup>68</sup>Ga-2a showed the highest level of binding (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>). NOTA is known to form more stable chelate with <sup>68</sup>Ga than DOTA, and thus, <sup>68</sup>Ga might be transchelated to serum proteins such as transferrin from the less stable chelates of DOTA and its derivatives.</p><p>Cell uptake studies after incubation of the cells with each agent showed that all three agents had significantly higher uptakes than the control compounds (<sup>68</sup>Ga-NOTA and <sup>68</sup>Ga-DOTA) in both Hep3B (a human hepatoma cell line) and CT-26 (a mouse colon cancer cell line) cells (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>). Of the three agents, <sup>68</sup>Ga-2a had the highest uptake in Hep3B cells, while <sup>68</sup>Ga-2b had the highest uptake in CT-26 cells.</p></div><div id="Ga68-2a-c.Animal_Studies"><h2 id="_Ga68-2a-c_Animal_Studies_">Animal Studies</h2><div id="Ga68-2a-c.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed/20926300" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of <sup>68</sup>Ga-2a, <sup>68</sup>Ga-2b, and <sup>68</sup>Ga-2c (10 ìCi/0.1 ml (0.37 MBq/0.1 ml)) was investigated after tail vein injection in mice bearing human colon cancer CT-26 xenografts (<i>n</i> = 4 mice/time point for each agent) (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>). Mice were euthanized at different times (10, 30, 60, and 120 min) after injection, and counts were obtained with a ã-scintillation counter. Tumor uptakes for all three agents were higher than those for most organs, except for the kidneys. Tumor/blood ratios were similar for all agents up to 60 min after injection but differed at 120 min. The tumor/blood ratios for <sup>68</sup>Ga-2a, <sup>68</sup>Ga-2b, and <sup>68</sup>Ga-2c were 0.72, 0.9, and 0.96, respectively, at 60 min after injection, and were 1.02, 1.41, and 1.73, respectively, at 120 min after injection. Tumor/muscle ratios were different among the agents. The highest tumor/muscle ratio was achieved by <sup>68</sup>Ga-2a (2.48), followed by <sup>68</sup>Ga-2b (1.65) and <sup>68</sup>Ga-2c (1.51) at 30 min after injection.</p><p>PET imaging in mice bearing human colon cancer CT-26 xenografts was performed at 30 min after injection of the agents (0.6–0.8 mCi (22.2–29.6 MBq)) through the tail vein (1). High levels of kidney and bladder activity were observed for all agents, indicating rapid renal excretion. Tumor uptakes were visualized by PET with all three agents (<sup>68</sup>Ga-2a, <sup>68</sup>Ga-2b, and <sup>68</sup>Ga-2c), but <sup>68</sup>Ga-2a demonstrated the highest tumor/muscle ratio (5.9).</p><p>In comparison between DOTA and NOTA derivatives, all agents showed fast renal excretion and blood clearance, low nonspecific uptake in normal organs except for kidneys, and relatively high uptake in tumor tissues (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>). In biodistribution studies, the tumor/blood ratios for NOTA-amino acid derivatives were higher than those for DOTA-amino acid derivatives at 2 h, although the ratios were similar for all six agents at 30 min after injection, which might be related to the higher serum protein binding by DOTA derivatives. In PET imaging, <sup>68</sup>Ga-1b demonstrated the highest tumor/muscle ratio (12.3), followed by <sup>68</sup>Ga-2a (5.9) and <sup>68</sup>Ga-2b (4.3). These results suggest that <sup>68</sup>Ga-1b is more favorable than others for use in PET imaging of tumors (<a class="bk_pop" href="#Ga68-2a-c.REF.1">1</a>).</p></div><div id="Ga68-2a-c.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28dog%20OR%20rabbit%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="Ga68-2a-c.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="Ga68-2a-c.Human_Studies"><h2 id="_Ga68-2a-c_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="Ga68-2a-c.References"><h2 id="_Ga68-2a-c_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.1">Shetty D., Jeong J.M., Ju C.H., Kim Y.J., Lee J.Y., Lee Y.S., Lee D.S., Chung J.K., Lee M.C.
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<em>Synthesis and evaluation of macrocyclic amino acid derivatives for tumor imaging by gallium-68 positron emission tomography.</em>
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<span><span class="ref-journal">Bioorg Med Chem. </span>2010;<span class="ref-vol">18</span>(21):7338–47.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/20926300" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20926300</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.2">McConathy, J., W. Yu, N. Jarkas, W. Seo, D.M. Schuster, and M.M. Goodman, <em>Radiohalogenated nonnatural amino acids as PET and SPECT tumor imaging agents.</em> Med Res Rev, 2011. [<a href="https://pubmed.ncbi.nlm.nih.gov/21793016" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21793016</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.3">Laverman P., Boerman O.C., Corstens F.H., Oyen W.J.
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||
<em>Fluorinated amino acids for tumour imaging with positron emission tomography.</em>
|
||
<span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2002;<span class="ref-vol">29</span>(5):681–90.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11976809" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11976809</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.4">Ganapathy V., Thangaraju M., Prasad P.D.
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<em>Nutrient transporters in cancer: relevance to Warburg hypothesis and beyond.</em>
|
||
<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>5.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.5">Goberdhan D.C.
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<em>Intracellular amino acid sensing and mTORC1-regulated growth: new ways to block an old target?</em>
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<span><span class="ref-journal">Curr Opin Investig Drugs. </span>2010;<span class="ref-vol">11</span>(12):1360–7.</span> [<a href="/pmc/articles/PMC3044466/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3044466</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/21154118" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21154118</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.6">Fuchs B.C., Bode B.P.
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<em>Amino acid transporters ASCT2 and LAT1 in cancer: partners in crime?</em>
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<span><span class="ref-journal">Semin Cancer Biol. </span>2005;<span class="ref-vol">15</span>(4):254–66.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15916903" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15916903</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.7">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>8.</dt><dd><div class="bk_ref" id="Ga68-2a-c.REF.8">Shetty D., Jeong J.M., Ju C.H., Lee Y.S., Jeong S.Y., Choi J.Y., Yang B.Y., Lee D.S., Chung J.K., Lee M.C.
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<em>Synthesis of novel 68Ga-labeled amino acid derivatives for positron emission tomography of cancer cells.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2010;<span class="ref-vol">37</span>(8):893–902.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21055619" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21055619</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: NBK65093</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/22013604" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">22013604</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/GhrelinDer68Ga/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Ga68-1a-c/" 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/NBK65093/?report=reader">PubReader</a></li><li><a href="/books/NBK65093/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK65093" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK65093" style="display:none" title="Cite this Page"><div class="bk_tt">Shan L. 68Ga-Labeled β-aminoalanine, γ-aminohomoalanine, and ε-aminolysine conjugates of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid. 2011 Aug 29 [Updated 2011 Oct 12]. 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/NBK65093/pdf/Bookshelf_NBK65093.pdf">PDF version of this page</a> (400K)</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="#Ga68-2a-c.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#Ga68-2a-c.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#Ga68-2a-c.In_Vitro_Studies_Testing_in_Ce" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#Ga68-2a-c.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#Ga68-2a-c.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#Ga68-2a-c.References" ref="log$=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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