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<meta name="ncbi_db" content="books" /><meta name="ncbi_pdid" content="book-part" /><meta name="ncbi_acc" content="NBK51063" /><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="/NBK51063/" /><meta name="ncbi_pagename" content="68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic 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>68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic 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 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2010/12/28" /><meta name="citation_author" content="Arvind Chopra" /><meta name="citation_pmid" content="21290633" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK51063/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic 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="2010/12/28" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK51063/" /><meta name="description" content="The prostate-specific membrane antigen (PSMA) is a type II membrane glycoprotein that is present primarily in the prostate and is overexpressed during all stages of the androgen-insensitive or the metastatic cancer of this organ (1). In addition, PSMA is expressed at lower levels (compared to the prostate) in the neovasculature of some solid tumors (for details, see Elsasser-Beile et al. (1)). Because of its high expression during the development and progression of a malignancy, PSMA is considered to be a good target for the imaging and treatment of prostate cancer (2). Several investigators have reported the use of radio-halogenated (e.g., 18F, 125I, etc.) and 99mTc-labeled small molecule inhibitors for the imaging of PSMA (3). Among these radionuclides, 18F is the most frequently used to label diverse positron emission tomography (PET) agents for diagnostic imaging because its addition to a molecule (usually by the replacement of a hydrogen atom) does not alter its chemical properties; however, due to its short half-life (~110 min), an on-site cyclotron is needed to produce this radio-halogen (4). Recently 68Ga (half-life, ~68 min) has been suggested to be a suitable alternative to the use of 18F for the production of PET imaging probes because 68Ga is easy to produce with a 68Ge/68Ga generator system that does not have to be on-site. However, it is necessary to mention that currently no 68Ge/68Ga generator system has been approved by the United States Food and Drug Administration (Eckelman: personal communication). In addition, 68Ga has been successfully used by some investigators to study cancer and tumor biology (4, 5). On the basis of these observations, and as an extension of their earlier work (for references, see Banerjee et al. (3)), Banerjee et al. developed two 68Ga-labeled, urea-based inhibitors of PSMA ([68Ga]-labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid ([68Ga]3) and [68Ga]-labeled 2-[3-(1-carboxy-5-{7-[5-carboxy-5-(3-phenyl-2-{3-phenyl-2-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]propionylamino}propionylamino)pentylcarbamoyl]heptanoylamino}pentyl)" /><meta name="og:title" content="68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid" /><meta name="og:type" content="book" /><meta name="og:description" content="The prostate-specific membrane antigen (PSMA) is a type II membrane glycoprotein that is present primarily in the prostate and is overexpressed during all stages of the androgen-insensitive or the metastatic cancer of this organ (1). In addition, PSMA is expressed at lower levels (compared to the prostate) in the neovasculature of some solid tumors (for details, see Elsasser-Beile et al. (1)). Because of its high expression during the development and progression of a malignancy, PSMA is considered to be a good target for the imaging and treatment of prostate cancer (2). Several investigators have reported the use of radio-halogenated (e.g., 18F, 125I, etc.) and 99mTc-labeled small molecule inhibitors for the imaging of PSMA (3). Among these radionuclides, 18F is the most frequently used to label diverse positron emission tomography (PET) agents for diagnostic imaging because its addition to a molecule (usually by the replacement of a hydrogen atom) does not alter its chemical properties; however, due to its short half-life (~110 min), an on-site cyclotron is needed to produce this radio-halogen (4). Recently 68Ga (half-life, ~68 min) has been suggested to be a suitable alternative to the use of 18F for the production of PET imaging probes because 68Ga is easy to produce with a 68Ge/68Ga generator system that does not have to be on-site. However, it is necessary to mention that currently no 68Ge/68Ga generator system has been approved by the United States Food and Drug Administration (Eckelman: personal communication). In addition, 68Ga has been successfully used by some investigators to study cancer and tumor biology (4, 5). On the basis of these observations, and as an extension of their earlier work (for references, see Banerjee et al. (3)), Banerjee et al. developed two 68Ga-labeled, urea-based inhibitors of PSMA ([68Ga]-labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid ([68Ga]3) and [68Ga]-labeled 2-[3-(1-carboxy-5-{7-[5-carboxy-5-(3-phenyl-2-{3-phenyl-2-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]propionylamino}propionylamino)pentylcarbamoyl]heptanoylamino}pentyl)" /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK51063/" /><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/PSMA68Ga3/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK51063/" /><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="#__NBK51063_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK51063_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/NOTABP68Ga/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Ga68-21-22/" 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="_NBK51063_"><span class="title" itemprop="name"><sup>68</sup>Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"> [<sup>68</sup>Ga]3</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK51063_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK51063_ai__"><div class="contrib half_rhythm"><span itemprop="author">Arvind Chopra</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH, Bethesda, MD 20894<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a></div></div></div></div><p class="small">Created: <span itemprop="datePublished">September 28, 2010</span>; Last Update: <span itemprop="dateModified">December 28, 2010</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="PSMA68Ga3.T.nc_chemical_name68galabeled_" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK51063/table/PSMA68Ga3.T.nc_chemical_name68galabeled_/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__PSMA68Ga3.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 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic 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/99430927" 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=99430927" alt="image 99430927 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;">[<sup>68</sup>Ga]<b>3</b></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;">Prostate-specific membrane antigen (PSMA)</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;">Antigen</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Positron emission tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal / contrast:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>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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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure for additional information on [<sup>68</sup>Ga]<b>3</b> 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="PSMA68Ga3.Background"><h2 id="_PSMA68Ga3_Background_">Background</h2><p>[<a href="/pubmed?term=psma%20and%20prostate%20cancer&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The prostate-specific membrane antigen (PSMA) is a type II membrane glycoprotein that is present primarily in the prostate and is overexpressed during all stages of the androgen-insensitive or the metastatic cancer of this organ (<a class="bk_pop" href="#PSMA68Ga3.REF.1">1</a>). In addition, PSMA is expressed at lower levels (compared to the prostate) in the neovasculature of some solid tumors (for details, see Elsasser-Beile et al. (<a class="bk_pop" href="#PSMA68Ga3.REF.1">1</a>)). Because of its high expression during the development and progression of a malignancy, PSMA is considered to be a good target for the imaging and treatment of prostate cancer (<a class="bk_pop" href="#PSMA68Ga3.REF.2">2</a>). Several investigators have reported the use of radio-halogenated (e.g., <sup>18</sup>F, <sup>125</sup>I, etc.) and <sup>99m</sup>Tc-labeled small molecule inhibitors for the imaging of PSMA (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). Among these radionuclides, <sup>18</sup>F is the most frequently used to label diverse positron emission tomography (PET) agents for diagnostic imaging because its addition to a molecule (usually by the replacement of a hydrogen atom) does not alter its chemical properties; however, due to its short half-life (~110 min), an on-site cyclotron is needed to produce this radio-halogen (<a class="bk_pop" href="#PSMA68Ga3.REF.4">4</a>). Recently <sup>68</sup>Ga (half-life, ~68 min) has been suggested to be a suitable alternative to the use of <sup>18</sup>F for the production of PET imaging probes because <sup>68</sup>Ga is easy to produce with a <sup>68</sup>Ge/<sup>68</sup>Ga generator system that does not have to be on-site. However, it is necessary to mention that currently no <sup>68</sup>Ge/<sup>68</sup>Ga generator system has been approved by the United States Food and Drug Administration (Eckelman: personal communication). In addition, <sup>68</sup>Ga has been successfully used by some investigators to study cancer and tumor biology (<a class="bk_pop" href="#PSMA68Ga3.REF.4" data-bk-pop-others="PSMA68Ga3.REF.5">4, 5</a>). On the basis of these observations, and as an extension of their earlier work (for references, see Banerjee et al. (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>)), Banerjee et al. developed two <sup>68</sup>Ga-labeled, urea-based inhibitors of PSMA ([<sup>68</sup>Ga]-labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid ([<sup>68</sup>Ga]<b>3</b>) and [<sup>68</sup>Ga]-labeled 2-[3-(1-carboxy-5-{7-[5-carboxy-5-(3-phenyl-2-{3-phenyl-2-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]propionylamino}propionylamino)pentylcarbamoyl]heptanoylamino}pentyl)</p><p>ureido]pentanedioic acid ([<sup>68</sup>Ga]<b>6</b>)) and evaluated them for biodistribution and the imaging of PSMA-expressing tumors in nude mice (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). This chapter details the results obtained with [<sup>68</sup>Ga]<b>3</b>. Results obtained with [<sup>68</sup>Ga]<b>6</b> are presented in a separate chapter of MICAD (<a href="http://www.micad.nih.gov/" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">www.micad.nih.gov</a>) (<a class="bk_pop" href="#PSMA68Ga3.REF.6">6</a>).</p><div id="PSMA68Ga3.Other_Sources_of_Information"><h3>Other Sources of Information</h3><p>PSMA-related chapters in <a href="/sites/entrez?db=Books&cmd=Search&term=PSMA+AND+micad%5bbook%5d&doptcmdl=TOCView&log%24=booksrch&bname=micad" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">MICAD</a>.</p><p>Alternate names and other information regarding PSMA in the <a href="http://www.hprd.org/alternate?hprd_id=02961&isoform_id=02961_1&isoform_name=Isoform_1" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Human Protein Reference Database</a>.</p><p><a href="http://clinicaltrials.gov/ct2/results?term=PSMA" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Clinical trials</a> involving PSMA and PSMA inhibitors.</p><p>Gene information (Gene ID: 2346) for human PSMA in <a href="/protein?Db=gene&Cmd=retrieve&dopt=full_report&list_uids=2346" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Entrez Gene</a>.</p><p>PSMA1 variant 3 <a href="/nuccore/NM_001193471.1" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Protein and mRNA sequence</a>.</p><p>Information on PSMA in Online Mendelian Inheritance in Man <a href="/omim/600934" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">(OMIM)</a>.</p></div></div><div id="PSMA68Ga3.Synthesis"><h2 id="_PSMA68Ga3_Synthesis_">Synthesis</h2><p>[<a href="/pubmed?term=%5B68Ga%5D3%20synthesis&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The synthesis of [<sup>68</sup>Ga]<b>3</b> has been described in detail by Banerjee et al. (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). The radiochemical yield and purity of the labeled compound were reported to be 76.2% and >99.0%, respectively. The retention time of [<sup>68</sup>Ga]<b>3</b> on analytical high-performance liquid chromatography (HPLC) was 25.0 min compared with a retention time of 22.5 min for [<sup>68</sup>Ga]<b>6</b>. The specific activity of [<sup>68</sup>Ga]<b>3</b> was reported to be between 3.0 and 6.0 MBq/nmol (81 and 162 μCi/nmol). After purification, the radiochemical was dried under vacuum and diluted in 0.9% saline to the desired tracer concentration before use in biodistribution and imaging studies. The stability of [<sup>68</sup>Ga]<b>3</b> under <i>in vitro</i> or <i>in vivo</i> conditions was not reported.</p></div><div id="PSMA68Ga3.In_Vitro_Studies_Testing_in_Ce"><h2 id="_PSMA68Ga3_In_Vitro_Studies_Testing_in_Ce_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed?term=68Ga-3%20in%20vitro&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Using unlabeled <b>3</b> and [<sup>68</sup>Ga]<b>3</b> in a fluorescence-based PSMA inhibition assay, the inhibitory concentrations of these compounds were reported to be 2.9 and 29.0 nM, respectively (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). In comparison, the PSMA inhibitory concentrations for unlabeled <b>6</b> and [<sup>68</sup>Ga]<b>6</b> were 1.23 and 0.44 nM, respectively.</p><p>Using a 1-octanol/water system, the partition coefficient of [<sup>68</sup>Ga]<b>3</b> was determined to be −3.9, which was similar to that of [<sup>68</sup>Ga]<b>6</b> (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). This indicated that both radiolabeled compounds were lipophilic (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). On the basis of the HPLC analysis reported above, [<sup>68</sup>Ga]<b>6</b> appeared to have a slightly higher lipophilicity than [<sup>68</sup>Ga]<b>3</b>.</p></div><div id="PSMA68Ga3.Animal_Studies"><h2 id="_PSMA68Ga3_Animal_Studies_">Animal Studies</h2><div id="PSMA68Ga3.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of [<sup>68</sup>Ga]<b>3</b> was studied in severe-combined immunodeficient mice bearing <a href="http://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CRL-1435&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PC-3</a>-PIP (transfected with the PSMA gene and expressing high levels of the antigen) and PC-3-FLU (does not express PSMA) cell xenograft tumors (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). The mice were injected with the tracer through the tail vein and euthanized 30, 60, 120, and 180 min after the injection (<i>n</i> = 4 mice/time point) to determine the amount of radioactivity accumulated in the tumors and major organs. Results obtained from this study were presented as percent of injected dose per gram tissue (% ID/g). At 30 min post-injection (p.i.), the PC-3-PIP tumors had an uptake of 3.78 ± 0.09% ID/g that reduced gradually to 1.10 ± 0.19% ID/g by 3 h p.i.; uptake in the PC-3-FLU tumors was 0.82 ± 0.20% ID/g at 30 min p.i. and 0.39 ± 0.02% ID/g at 3 h p.i. During the same period, the label cleared rapidly from the kidneys, with an uptake of 97.19 ± 16.07% ID/g at 30 min p.i. that decreased to 2.13 ± 0.11% ID/g at 3 h p.i. Except for the bladder, all other organs had <1.0% ID/g incorporation of radioactivity by 3 h p.i. The accumulation of radioactivity in the bladder was 8.96 ± 5.30% ID/g at 30 min p.i., and this increased to 25.29 ± 8.63% ID/g at 60 min p.i. and decreased to 5.39 ± 2.98 at 3 h p.i. This indicated that the tracer was excreted mainly through the urinary route. The PC-3-PIP tumor/muscle uptake ratio (T/M) increased from 8.30 at 30 min p.i. to 20.37 at 3 h p.i. In comparison, the T/M for the PC-3-FLU tumors was 1.80 at 30 min p.i. and increased to 7.34 at 3 h p.i. In mice injected with [<sup>68</sup>Ga]<b>6</b> PC-3-PIP, the T/M ratio was 4.17 at 30 min p.i. and increased to 436.29 at 3 h p.i.; during the same time, the PC-3-FLU T/M ratio increased from 1.67 at 30 min p.i. to 28.70 at 3 h p.i. in these animals (for other details on [<sup>68</sup>Ga]<b>6</b>, see the related chapter in MICAD (<a class="bk_pop" href="#PSMA68Ga3.REF.6">6</a>)).</p><p>For the PET imaging study, a single animal bearing <a href="http://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=CRL-1740&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">LNCaP</a> cell (expressing PSMA) tumors was injected intravenously with either [<sup>68</sup>Ga]<b>3</b> or [<sup>68</sup>Ga]<b>6</b> as described by Banerjee et al. (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). From the PET images it was clear that both tracers accumulated primarily in the PSMA-positive tumors and the kidneys (the kidneys are known to express PSMA in the proximal renal tubules), similar to observations made during the biodistribution study. In a blocking study, the tumor-bearing mice (number of mice used per time point was not reported) were injected with 2-(phosphonomethyl)pentanedioic acid (2-PMPA) (50 mg/kg body weight), a known selective ligand of PSMA, and later the animals were injected with the respective tracers (time elapsed between the pretreatment with 2-PMPA and injection of the tracer was not reported). PET images of the animals were acquired at 30 and 60 min p.i., and it was observed that the PSMA-expressing tumors and the kidneys did not accumulate either tracer, suggesting that both radiochemicals bound specifically to the membrane antigen.</p><p>From these studies, the investigators concluded that both [<sup>68</sup>Ga]<b>3</b> and [<sup>68</sup>Ga]<b>6</b> bind specifically to PSMA and could be used for the imaging of PSMA-positive tumors in rodents (<a class="bk_pop" href="#PSMA68Ga3.REF.3">3</a>). They also mentioned that more animal studies are necessary before these radiochemicals can be evaluated in the clinic.</p></div><div id="PSMA68Ga3.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed?term=68Ga-3%20Non-Primate%20Mammals&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="PSMA68Ga3.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed?term=68Ga-3%20Non-Human%20Primates&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="PSMA68Ga3.Human_Studies"><h2 id="_PSMA68Ga3_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed?term=68Ga-3%20Human%20Studies&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="PSMA68Ga3.Supplemental_Information"><h2 id="_PSMA68Ga3_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="PSMA68Ga3.NIH_Support"><h2 id="_PSMA68Ga3_NIH_Support_">NIH Support</h2><p>These studies were funded by National Institutes of Health grants R01CA134675 and U24 CA92871.</p></div><div id="PSMA68Ga3.References"><h2 id="_PSMA68Ga3_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="PSMA68Ga3.REF.1">Elsasser-Beile U., Buhler P., Wolf P. Targeted therapies for prostate cancer against the prostate specific membrane antigen. <span><span class="ref-journal">Curr Drug Targets. </span>2009;<span class="ref-vol">10</span>(2):118–25.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19199907" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19199907</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="PSMA68Ga3.REF.2">Dijkgraaf I., Boerman O.C. Radionuclide imaging of tumor angiogenesis. <span><span class="ref-journal">Cancer Biother Radiopharm. </span>2009;<span class="ref-vol">24</span>(6):637–47.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/20025543" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20025543</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="PSMA68Ga3.REF.3">Banerjee S.R., Pullambhatla M., Byun Y., Nimmagadda S., Green G., Fox J.J., Horti A., Mease R.C., Pomper M.G. 68Ga-labeled inhibitors of prostate-specific membrane antigen (PSMA) for imaging prostate cancer. <span><span class="ref-journal">J Med Chem. </span>2010;<span class="ref-vol">53</span>(14):5333–41.</span> [<a href="/pmc/articles/PMC3341619/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3341619</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20568777" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20568777</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="PSMA68Ga3.REF.4">Fani M., Andre J.P., Maecke H.R. 68Ga-PET: a powerful generator-based alternative to cyclotron-based PET radiopharmaceuticals. <span><span class="ref-journal">Contrast Media Mol Imaging. </span>2008;<span class="ref-vol">3</span>(2):67–77.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18383558" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18383558</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="PSMA68Ga3.REF.5">Holland J.P., Williamson M.J., Lewis J.S. Unconventional nuclides for radiopharmaceuticals. <span><span class="ref-journal">Mol Imaging. </span>2010;<span class="ref-vol">9</span>(1):1–20.</span> [<a href="/pmc/articles/PMC4962336/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC4962336</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20128994" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20128994</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="PSMA68Ga3.REF.6">Chopra, A., [68Ga]-Labeled 2-[3-(1-Carboxy-5-{7-[5-carboxy-5-(3-phenyl-2-{3-phenyl-2-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]propionylamino}propionylamino)pentylcarbamoyl]heptanoylamino}pentyl)ureido]pentanedioic Acid. 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/21249764" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21249764</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></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/NBK51063/?report=reader">PubReader</a></li><li><a href="/books/NBK51063/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK51063" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK51063" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. 68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid. 2010 Sep 28 [Updated 2010 Dec 28]. 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/NBK51063/pdf/Bookshelf_NBK51063.pdf">PDF version of this page</a> (136K)</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="#PSMA68Ga3.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#PSMA68Ga3.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#PSMA68Ga3.In_Vitro_Studies_Testing_in_Ce" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#PSMA68Ga3.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#PSMA68Ga3.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#PSMA68Ga3.Supplemental_Information" ref="log$=inpage&link_id=inpage">Supplemental Information</a></li><li><a href="#PSMA68Ga3.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#PSMA68Ga3.References" ref="log$=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 value="("Nitrogen 13" OR 13N)">Nitrogen-13</option><option value="("Yttrium 86" OR 86Y)">Yttrium-86</option><option value="("Zirconium 89" OR 89Zr)">Zirconium-89</option></optgroup><optgroup label="Photoacoustic agents"><option value="(Gold OR Au)">Gold</option><option value="("Indocyanine green" OR ICG)">Indocyanine green</option></optgroup><optgroup label="SPECT radionuclides"><option value="(Gallium-67 OR 67Ga)">Gallium-67</option><option value="("Indium 111" OR 111In)">Indium-111</option><option value="("Iodine 123" OR "Iodine 125" OR "Iodine 131" OR 123I OR 125I OR 131I)">Iodine-123, 125, 131</option><option value="("Lutetium 177" OR 177Lu)">Lutetium-177</option><option value="(Rhenium OR 186Re OR 188Re)">Rhenium</option><option value="("Technetium 99m" OR 99mTc)">Technetium-99m</option><option value="("Tellurium 125m" OR 125mTe)">Tellurium-125m</option></optgroup><optgroup label="Ultrasound agents"><option value="Microbubbles">Microbubbles</option><option 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receptor-antibody OR antibody-receptor)">Receptors</option><option value="transporter">Transporters</option><option value="non-targeted">Non-targeted</option><option value=""nucleic acid"">Nucleic acids</option><option value="(non-targeted OR "unknown binding site")">Others</option></select></div></div><div><input id="__micad_btn_1" type="radio" name="stage" value="vitro" /><label for="__micad_btn_1"><i>In vitro</i></label><input id="__micad_btn_2" type="radio" name="stage" value="rodents" /><label for="__micad_btn_2">Rodents</label><input id="__micad_btn_3" type="radio" name="stage" value="mammals" /><label for="__micad_btn_3">Non-primate non-rodent mammals</label><br /><input id="__micad_btn_4" type="radio" name="stage" value="primates" /><label for="__micad_btn_4">Non-human primates</label><input id="__micad_btn_5" type="radio" name="stage" value="humans" /><label for="__micad_btn_5">Humans</label><input id="__micad_btn_6" type="radio" name="stage" value="any" checked="checked" 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(123)I-Labeled (S)-2-(3-((S)-1-carboxy-5-(4-iodobenzylamino)pentyl)ureido)pentanedoic acid.<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 class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/30843003" ref="ordinalpos=1&linkpos=4&log$=relatedarticles&logdbfrom=pubmed">More advantages in detecting bone and soft tissue metastases from prostate cancer using (18)F-PSMA PET/CT.</a><span class="source">[Hell J Nucl Med. 2019]</span><div class="brieflinkpop offscreen_noflow">More advantages in detecting bone and soft tissue metastases from prostate cancer using (18)F-PSMA PET/CT.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Pianou NK, Stavrou PZ, Vlontzou E, Rondogianni P, Exarhos DN, Datseris IE. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Hell J Nucl Med. 2019 Jan-Apr; 22(1):6-9. Epub 2019 Mar 7.</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20662139" ref="ordinalpos=1&linkpos=5&log$=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> IRDye800-2-(3-{5-[7-(5-amino-1-carboxy-pentylcarbamoyl)-heptanoylamino]-1-carboxy-pentyl}-ureido)-pentanedioic 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> IRDye800-2-(3-{5-[7-(5-amino-1-carboxy-pentylcarbamoyl)-heptanoylamino]-1-carboxy-pentyl}-ureido)-pentanedioic 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></ul><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed_reviews&uid=21290633" ref="ordinalpos=1&log$=relatedreviews_seeall&logdbfrom=pubmed">See reviews...</a><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed&uid=21290633" ref="ordinalpos=1&log$=relatedarticles_seeall&logdbfrom=pubmed">See all...</a></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Recent Activity</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="recent_activity" id="Shutter"></a></div><div class="portlet_content"><div xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" id="HTDisplay" class=""><div class="action"><a href="javascript:historyDisplayState('ClearHT')">Clear</a><a href="javascript:historyDisplayState('HTOff')" class="HTOn">Turn Off</a><a href="javascript:historyDisplayState('HTOn')" class="HTOff">Turn On</a></div><ul id="activity"><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=1" href="/portal/utils/pageresolver.fcgi?recordid=67d647ce67c23b31e0361c39">68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4...</a><div class="ralinkpop offscreen_noflow">68Ga-Labeled 2-{3-[5-(7-{1-benzyloxycarbonyl-5-[2-(4,7,10-tris-carboxymethyl-1,4,7,10-tetraazacyclododec-1-l)acetylamino]pentylcarbamoyl}-heptanoylamino)-1-carboxypentyl]ureido}pentanedioic acid - 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