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<title>111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide - 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="111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2008/04/03" /><meta name="citation_author" content="Kenneth T. Cheng" /><meta name="citation_pmid" content="20641278" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK23073/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Kenneth T. Cheng" /><meta name="DC.Date" content="2008/04/03" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK23073/" /><meta name="description" content="111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide (111In-DOTA-H6-Met) is a radiolabeled gastrin analog that can be used for single-photon emission computed tomography (SPECT) imaging of tumors that express the gastrin/cholecystokinin-2 (CCK-2) receptor (1). 111In is a gamma emitter with a physical half-life (t½) of 2.8 days." /><meta name="og:title" content="111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide" /><meta name="og:type" content="book" /><meta name="og:description" content="111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide (111In-DOTA-H6-Met) is a radiolabeled gastrin analog that can be used for single-photon emission computed tomography (SPECT) imaging of tumors that express the gastrin/cholecystokinin-2 (CCK-2) receptor (1). 111In is a gamma emitter with a physical half-life (t½) of 2.8 days." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK23073/" /><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/H6Met111In/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK23073/" /><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="#__NBK23073_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23073_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/H2Met111In/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/tPTP111In/" 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="_NBK23073_"><span class="title" itemprop="name"><sup>111</sup>In-Tetraazacyclododecane-<i>N</i>,<i>N’</i>,<i>N’’</i>,<i>N’’’</i>-tetraacetic acid-HHHHHH-EAYGWMDF-NH<sub>2</sub> peptide </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"><sup>111</sup>In-DOTA-H6-Met</div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23073_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23073_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kenneth T. Cheng</span>, PhD<div class="affiliation small">
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National Center for Biotechnology Information, NLM, NIH, Bethesda, MD,
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<span class="before-email-separator"></span><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>
|
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</div></div></div><p class="small">Created: <span itemprop="datePublished">April 23, 2007</span>; Last Update: <span itemprop="dateModified">April 3, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="H6Met111In.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23073/table/H6Met111In.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__H6Met111In.T1_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>111</sup>In-Tetraazacyclododecane-<i>N</i>,<i>N’</i>,<i>N’’</i>,<i>N’’’</i>-tetraacetic acid-HHHHHH-EAYGWMDF-NH<sub>2</sub> peptide</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;"></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>111</sup>In-DOTA-H6-Met</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;">Radiolabeled minigastrin</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;">Peptide</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;">Gastrin/cholecystokinin-2 (CCK-2, CCK-B) receptor</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;">Receptor binding</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;">Single-photon emission computed tomography (SPECT), planar gamma imaging</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>111</sup>In</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></ul>
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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" /> Rodents
|
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</div></li></ul>
|
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<br />
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on <a href="/entrez/viewer.fcgi?db=protein&id=417029" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">protein</a>, <a href="/entrez/viewer.fcgi?db=nuccore&id=33356159" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">nucleotide</a> (RefSeq), and <a href="/sites/entrez?Db=gene&Cmd=ShowDetailView&TermToSearch=887&ordinalpos=1&itool=EntrezSystem2.PEntrez.Gene.Gene_ResultsPanel.Gene_RVDocSum" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">gene</a> for more information about.the CCK-2 receptor.</td></tr></tbody></table></div></div><div id="H6Met111In.Background"><h2 id="_H6Met111In_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><sup>111</sup>In-Tetraazacyclododecane-<i>N</i>,<i>N’</i>,<i>N’’</i>,<i>N’’’</i>-tetraacetic acid-HHHHHH-EAYGWMDF-NH<sub>2</sub> peptide (<sup>111</sup>In-DOTA-H6-Met) is a radiolabeled gastrin analog that can be used for single-photon emission computed tomography (SPECT) imaging of tumors that express the gastrin/cholecystokinin-2 (CCK-2) receptor (<a class="bk_pop" href="#H6Met111In.REF.1">1</a>). <sup>111</sup>In is a gamma emitter with a physical half-life (<i>t</i><sub>½</sub>) of 2.8 days.</p><p>The gastrointestinal peptides gastrin and CCK have various regulatory functions in the brain and gastrointestinal tract (<a class="bk_pop" href="#H6Met111In.REF.2">2</a>). Gastrin and CCK have the same COOH-terminal pentapeptide amide sequence, which is the biologically active site (<a class="bk_pop" href="#H6Met111In.REF.3">3</a>). Human gastrin is a peptide composed of 34 amino acids and also exists in several C-terminal truncated forms (<a class="bk_pop" href="#H6Met111In.REF.1">1</a>). These C-terminal truncated forms include minigastrin, which is a 13-residue peptide with the sequence of LEEEEEAYGWMDF-NH<sub>2</sub>. CCKs exist in a variety of biologically active molecular forms that are derived from a precursor molecule comprising 115 amino acids (<a class="bk_pop" href="#H6Met111In.REF.4">4</a>). These forms range from 4 to 58 amino acids in length and include sulphated and unsulphated CCK-8, which has the structure DYMGWMDF-NH<sub>2</sub>. They bind to and act through transmembrane G-protein–coupled receptors (<a class="bk_pop" href="#H6Met111In.REF.5">5</a>). Two different CCK receptor subtypes have been identified in normal tissues. CCK-1 (CCK-A, alimentary) receptors have low affinity for gastrin, and CCK-2 (CCK-B, brain) receptors have high affinity for gastrin (<a class="bk_pop" href="#H6Met111In.REF.4">4</a>). They also differ in terms of molecular structure, distribution, and affinity for CCK. These receptors have also been found to be expressed or overexpressed on a multitude of tumor types (<a class="bk_pop" href="#H6Met111In.REF.5">5</a>). CCK-2 receptors have been found most frequently in medullary thyroid carcinoma, small-cell lung cancers, astrocytomas, and stromal ovarian cancers (<a class="bk_pop" href="#H6Met111In.REF.2">2</a>). CCK-1 receptors have been identified in gastroenteropancreatic tumors, meningiomas, and neuroblastoma.</p><p>Reubi et al. (<a class="bk_pop" href="#H6Met111In.REF.6">6</a>) designed a series of radiolabeled CCK-8 peptides that showed high specificity for potential <i>in vivo</i> imaging of tumors expressing CCK-2 receptors. de Jong et al. (<a class="bk_pop" href="#H6Met111In.REF.7">7</a>) developed an <sup>111</sup>In-labeled non-sulfated CCK8 analog that used 1,4,7,10-tetraazacyclododecane-<i>N,N',N'',N'''</i>-tetraacetic acid (DOTA) as a bifunctional chelating agent. The radioligand showed high specific internalization rates in receptor-positive AR42J rat pancreatic tumor cells. von Guggenberg et al. (<a class="bk_pop" href="#H6Met111In.REF.8">8</a>) reported the synthesis of <a href="/books/n/micad/HYNICMG11Tc99m/"><sup>99m</sup>Tc-hydrazinonicotinic acid (HYNIC)-minigastrin</a> complexes and showed high tumor uptake in nude mice bearing AR42J tumors. Nock et al. (<a class="bk_pop" href="#H6Met111In.REF.9">9</a>) prepared <a href="/books/n/micad/HYNICMG0Tc99m/"><sup>99m</sup>Tc-labeled minigastrin</a> analogs and found that they displayed high specific localization in nude mice bearing AR42J tumors. Mather et al. (<a class="bk_pop" href="#H6Met111In.REF.1">1</a>) synthesized a library of different peptide sequences based on the C-terminal sequences of CCK-8 or minigastrin. These peptides were labeled with <sup>111</sup>In by DOTA or diethylenetriamine pentaacetic acid (DTPA) conjugation. Although their ultimate goal was to identify an analog that could be used for radiotherapeutic applications, <sup>111</sup>In-DOTA-H6-Met with a hexahistidine tag was evaluated as a potential molecular probe for CCK-2 receptors.</p></div><div id="H6Met111In.Synthesis"><h2 id="_H6Met111In_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29%29%20AND%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The peptide sequence HHHHHH-EAYGWMDF-amide was obtained by solid-phase peptide synthesis under standard conditions from commercial sources (<a class="bk_pop" href="#H6Met111In.REF.1">1</a>). The N-terminus was capped with a DOTA chelating group to produce DOTA-H6-Met. The identity and purity were confirmed by matrix-assisted laser desorption/ionization mass spectroscopy and reverse-phase high-performance liquid chromatography (HPLC). Radiolabeling was performed by mixing <sup>111</sup>In-chloride in ammonium acetate and 0.04-M monothioglycerol (MTG), an antioxidant, with DOTA-H6-Met in 0.01-M phosphate-buffered saline (pH 7.2). The mixture was heated at 98ºC for 15 min, and 0.1-M ethylenediamine tetraacetic acid (EDTA) was then added to quench the reaction. The labeling yield was >90%. The radiochemical purity and specific activity were not reported.</p></div><div id="H6Met111In.In_Vitro_Studies_Tes"><h2 id="_H6Met111In_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29%29%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>An <i>in vitro</i> receptor affinity assay of <sup>111</sup>In-DOTA-H6-Met was performed by using AGS human gastric tumor cells transfected with the CCK-2 receptor (AGS-CCK2R) and <sup>125</sup>I-G17 as the radioligand. The inhibition constant (<i>K</i><sub>i</sub>) and half of the maximum binding fraction (EC<sub>50</sub>) were 2.1 nM and 3.1 nM, respectively.</p></div><div id="H6Met111In.Animal_Studies"><h2 id="_H6Met111In_Animal_Studies_">Animal Studies</h2><div id="H6Met111In.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29%29%20AND%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Biodistribution studies of <sup>111</sup>In-DOTA-H6-Met were performed in nude mice bearing AR42J rat pancreatic tumors (<a class="bk_pop" href="#H6Met111In.REF.1">1</a>), HT29 human colorectal tumors, or CA20948 rat pancreatic tumors. Both AR42J and CA20948 tumors expressed different levels of gastrin receptors, and HT29 was a cell line transfected with a relatively low level of gastrin receptors. Each mouse received 0.2 μg of <sup>111</sup>In-DOTA-H6-Met by i.v. injection. The tumor radioactivity levels at 4 h (<i>n</i> = 3–4), represented as percent injected dose per g (% ID/g), were 0.59 ± 0.14, 0.55 ± 0.14, and 0.26 ± 0.04 for AR42J, CA20948, and HT29 tumors, respectively. The blood radioactivity levels at 4 h were 0.20 ± 0.03, 0.21 ± 0.01, and 0.26 ± 0.03 for AR42J, CA20948, and HT29 tumors, respectively. The kidney radioactivity levels at 4 h were 2.95 ± 0.60, 3.08 ± 0.77, and 3.47 ± 0.52 for AR42J, CA20948, and HT29 tumors, respectively. No blocking study was performed.</p></div><div id="H6Met111In.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29%29%20AND%20%28dog%20OR%20rabbit%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="H6Met111In.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29%29%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="H6Met111In.Human_Studies"><h2 id="_H6Met111In_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28radiolabeled%20gastrin%20analogs%29%20OR%20%28111in-cck-2%20receptor%20peptide%29%29%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="H6Met111In.references"><h2 id="_H6Met111In_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="H6Met111In.REF.1">Mather S.J. , McKenzie A.J. , Sosabowski J.K. , Morris T.M. , Ellison D. , Watson S.A. Selection of radiolabeled gastrin analogs for Peptide receptor-targeted radionuclide therapy. <span><span class="ref-journal">J Nucl Med. </span>2007;<span class="ref-vol">
|
||
<strong>48</strong>
|
||
</span>(4):615–22.</span> [<a href="/pmc/articles/PMC2246928/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2246928</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17401100" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17401100</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="H6Met111In.REF.2">Reubi J.C. , Schaer J.C. , Waser B. Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors. <span><span class="ref-journal">Cancer Res. </span>1997;<span class="ref-vol">
|
||
<strong>57</strong>
|
||
</span>(7):1377–86.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9102227" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9102227</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="H6Met111In.REF.3">Aly A. , Shulkes A. , Baldwin G.S. Gastrins, cholecystokinins and gastrointestinal cancer. <span><span class="ref-journal">Biochim Biophys Acta. </span>2004;<span class="ref-vol">
|
||
<strong>1704</strong>
|
||
</span>(1):1–10.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15238241" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15238241</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="H6Met111In.REF.4">Wang H. , Wong P.T. , Spiess J. , Zhu Y.Z. Cholecystokinin-2 (CCK2) receptor-mediated anxiety-like behaviors in rats. <span><span class="ref-journal">Neurosci Biobehav Rev. </span>2005;<span class="ref-vol">
|
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<strong>29</strong>
|
||
</span>(8):1361–73.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16120463" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16120463</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="H6Met111In.REF.5">Behr T.M. , Behe M.P. Cholecystokinin-B/Gastrin receptor-targeting peptides for staging and therapy of medullary thyroid cancer and other cholecystokinin-B receptor-expressing malignancies. <span><span class="ref-journal">Semin Nucl Med. </span>2002;<span class="ref-vol">
|
||
<strong>32</strong>
|
||
</span>(2):97–109.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11965605" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11965605</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="H6Met111In.REF.6">Reubi J.C. , Waser B. Unexpected high incidence of cholecystokinin-B/gastrin receptors in human medullary thyroid carcinomas. <span><span class="ref-journal">Int J Cancer. </span>1996;<span class="ref-vol">
|
||
<strong>67</strong>
|
||
</span>(5):644–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8782652" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8782652</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="H6Met111In.REF.7">de Jong M. , Bakker W.H. , Bernard B.F. , Valkema R. , Kwekkeboom D.J. , Reubi J.C. , Srinivasan A. , Schmidt M. , Krenning E.P. Preclinical and initial clinical evaluation of 111In-labeled nonsulfated CCK8 analog: a peptide for CCK-B receptor-targeted scintigraphy and radionuclide therapy. <span><span class="ref-journal">J Nucl Med. </span>1999;<span class="ref-vol">
|
||
<strong>40</strong>
|
||
</span>(12):2081–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10616889" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10616889</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="H6Met111In.REF.8">von Guggenberg E. , Behe M. , Behr T.M. , Saurer M. , Seppi T. , Decristoforo C. 99mTc-labeling and in vitro and in vivo evaluation of HYNIC- and (Nalpha-His)acetic acid-modified [D-Glu1]-minigastrin. <span><span class="ref-journal">Bioconjug Chem. </span>2004;<span class="ref-vol">
|
||
<strong>15</strong>
|
||
</span>(4):864–71.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15264875" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15264875</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="H6Met111In.REF.9">Nock B.A. , Maina T. , Behe M. , Nikolopoulou A. , Gotthardt M. , Schmitt J.S. , Behr T.M. , Macke H.R. CCK-2/gastrin receptor-targeted tumor imaging with (99m)Tc-labeled minigastrin analogs. <span><span class="ref-journal">J Nucl Med. </span>2005;<span class="ref-vol">
|
||
<strong>46</strong>
|
||
</span>(10):1727–36.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16204724" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16204724</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: NBK23073</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641278" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641278</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/H2Met111In/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/tPTP111In/" 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/NBK23073/?report=reader">PubReader</a></li><li><a href="/books/NBK23073/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23073" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23073" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT. 111In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHHHHH-EAYGWMDF-NH2 peptide. 2007 Apr 23 [Updated 2008 Apr 3]. 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/NBK23073/pdf/Bookshelf_NBK23073.pdf">PDF version of this page</a> (132K)</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="#H6Met111In.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#H6Met111In.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#H6Met111In.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#H6Met111In.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#H6Met111In.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#H6Met111In.references" ref="log$=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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href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=1513772" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641328" ref="ordinalpos=1&linkpos=1&log$=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> (111)In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-HHEAYGWMDF-NH(2) peptide.</a><span class="source">[Molecular Imaging and Contrast...]</span><div 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acid-dihistidine-norleucine peptide analog.</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> (111)In-Tetraazacyclododecane-N,N’,N’’,N’’’-tetraacetic acid-dihistidine-norleucine peptide analog.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Cheng KT. </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/20641448" ref="ordinalpos=1&linkpos=3&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" 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