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<title>4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(S)-[N-3-amino-(SCN-Bz-DOTA-111In)-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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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="#__NBK23033_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23033_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/TrastFab111In/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/mIgGtat111In/" 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="_NBK23033_"><span class="title" itemprop="name">4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(<i>S</i>)-[<i>N</i>-3-amino-(SCN-Bz-DOTA-<sup>111</sup>In)-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">IAC-SCN-Bz-DOTA-<sup>111</sup>In</div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD, <span itemprop="author">Chang H. Paik</span>, PhD, and <span itemprop="author">Narasimhan Danthi</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23033_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23033_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 class="contrib half_rhythm"><span itemprop="author">Chang H. Paik</span>, PhD<div class="affiliation small">
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Department of Nuclear Medicine, Warren G. Magnuson Clinical Center, NIH, Bethesda, MD, Corresponding Author,
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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.liam@kiapc" class="oemail">vog.hin.liam@kiapc</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Narasimhan Danthi</span>, PhD<div class="affiliation small">
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Department of Radiology, Warren G. Magnuson Clinical Center, 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.cc@ihtnaDN" class="oemail">vog.hin.cc@ihtnaDN</a>
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</div></div></div><p class="small">Created: <span itemprop="datePublished">July 9, 2007</span>; Last Update: <span itemprop="dateModified">December 18, 2007</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="IAC111In.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23033/table/IAC111In.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__IAC111In.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;">4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(<i>S</i>)-[<i>N</i>-3-amino-(SCN-Bz-DOTA-<sup>111</sup>In)-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/26657387" 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=26657387" alt="image 26657387 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;">IAC-SCN-Bz-DOTA-<sup>111</sup>In</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>111</sup>In-IAC, IAC-2-(<i>p</i>-isothiocyanatobenzyl)-DOTA-<sup>111</sup>In</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;">Integrin α<sub>v</sub>β<sub>3</sub></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:</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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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure for additional information in <a href="http://pubchem.ncbi.nlm.nih.gov" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.<br />Click on <a href="/entrez/viewer.fcgi?db=protein&val=4504763" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">protein</a>, <a href="/entrez/viewer.fcgi?db=nucleotide&val=40217844" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">nucleotide</a> (RefSeq), and <a href="/entrez/query.fcgi?db=gene&cmd=Retrieve&dopt=full_report&list_uids=3685" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">gene</a> for more information about integrin α<sub>v</sub>β<sub>3</sub>.</td></tr></tbody></table></div></div><div id="IAC111In.Background"><h2 id="_IAC111In_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(<i>S</i>)-[<i>N</i>-3-amino-(SCN-Bz-DOTA-<sup>111</sup>In)-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine (IAC-SCN-Bz-DOTA-<sup>111</sup>In) is an integrin-targeted molecular imaging agent conjugated with <sup>111</sup>In that was developed for single-photon emission computed tomography (SPECT) or planar gamma imaging of tumor vasculature and tumor angiogenesis (<a class="bk_pop" href="#IAC111In.EXTYLES.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>Cellular survival, invasion, and migration control embryonic development, angiogenesis, tumor metastasis, and other physiological processes (<a class="bk_pop" href="#IAC111In.EXTYLES.2">2</a>, <a class="bk_pop" href="#IAC111In.EXTYLES.3">3</a>). Among the molecules that regulate angiogenesis are integrins, which comprise a superfamily of cell adhesion proteins that form heterodimeric receptors for extracellular matrix (ECM) molecules (<a class="bk_pop" href="#IAC111In.EXTYLES.4">4</a>, <a class="bk_pop" href="#IAC111In.EXTYLES.5">5</a>). These transmembrane glycoproteins consist of two noncovalently associated subunits, α and β (18 α- and 8 β-subunits in mammals), which are assembled into at least 24 α/β pairs. Several integrins, such as integrin α<sub>v</sub>β<sub>3</sub>, have affinity for the arginine-glycine-aspartic acid (RGD) tripeptide motif, which is found in many ECM proteins. Expression of integrin α<sub>v</sub>β<sub>3</sub> receptors on endothelial cells is stimulated by angiogenic factors and environments. The integrin α<sub>v</sub>β<sub>3</sub> receptor is generally not found in normal tissue, but it is strongly expressed in vessels with increased angiogenesis, such as tumor vasculature. It is significantly upregulated in certain types of tumor cells and in almost all tumor vasculature. Molecular imaging probes carrying the RGD motif that binds to the integrin α<sub>v</sub>β<sub>3</sub> can be used to image tumor vasculature and evaluate angiogenic response to tumor therapy (<a class="bk_pop" href="#IAC111In.EXTYLES.6">6</a>, <a class="bk_pop" href="#IAC111In.EXTYLES.7">7</a>).</p><p>Various RGD peptides in both linear and cyclic forms have been developed for <i>in vivo</i> binding to integrin α<sub>v</sub>β<sub>3</sub> (<a class="bk_pop" href="#IAC111In.EXTYLES.8">8</a>). Non-peptide integrin α<sub>v</sub>β<sub>3</sub>–targeted molecular probes have also been investigated (<a class="bk_pop" href="#IAC111In.EXTYLES.9">9-11</a>). Duggan et al. (<a class="bk_pop" href="#IAC111In.EXTYLES.10">10</a>) modified a potent fibrinogen receptor antagonist from the sulfonamide exo-site class to generate non-peptide compounds with high affinity for the integrin α<sub>v</sub>β<sub>3</sub> receptor. The centrally -constrained benzoylamino-3-propionic acid scaffold appeared to provide optimum spacing between the acidic and basic portions of these ligands for binding. Based on the potent α<sub>v</sub>β<sub>3</sub> inhibitor 4-[2-(3,4,5,6-tetrahydropyrimidine-2-ylamino)ethyloxy]benzoyl-2-(<i>S</i>)-aminoethylsulfonyl-amino-β-alanine (IA) which has a 50% inhibitory concentration (IC<sub>50</sub>) of 0.04 μM and was used by Hood et al. (<a class="bk_pop" href="#IAC111In.EXTYLES.11">11</a>) to covalently couple to a cationic nanoparticle for targeted gene therapy, Burnett et al. (<a class="bk_pop" href="#IAC111In.EXTYLES.9">9</a>) designed and synthesized a series of aliphatic carbamate derivatives with enhanced binding affinity. The peptidomimetic 4-[2-(3,4,5,6-tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(<i>S</i>)-[<i>N</i>-(3-amino-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine hydrochloride (IAC) ligand was conjugated to a fluorescence label (FITC-IAC) as an integrin α<sub>v</sub>β<sub>3</sub> molecular probe for optical imaging of α<sub>v</sub>β<sub>3</sub>-expressing tumors. To develop a radioligand for SPECT imaging, Jang et al. (<a class="bk_pop" href="#IAC111In.EXTYLES.1">1</a>) successfully prepared IAC-SCN-Bz-DOTA-<sup>111</sup>In for studies in nude mice bearing the human M21 melanoma tumor.</p></div><div id="IAC111In.Synthesis"><h2 id="_IAC111In_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Burnett et al. (<a class="bk_pop" href="#IAC111In.EXTYLES.9">9</a>) reported the synthesis of IAC from commercially available amino alcohol. The amine was first protected as the <i>t</i>-butoxycarbonyl (<i>t</i>-Boc) derivative and then activated as 3-(Boc-amino)neopentyl-1-<i>O</i>-carbonylimidazole. The activated alcohol was then coupled to the free amine of IA to provide the Boc carbamate. The Boc carbamate was deprotected with anhydrous hydrochloric acid in dioxane to yield IAC. For radiolabeling, a bifunctional chelate was first conjugated to the amino terminus of IAC. Commercially obtained 2-(<i>p</i>-isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane-<i>N</i>,<i>N'</i>,<i>N''</i>,<i>N'''</i>-tetraacetic acid (SCN-Bz-DOTA) was reacted with IAC in 0.1 M sodium bicarbonate (pH 8.4) for 2 days at room temperature (<a class="bk_pop" href="#IAC111In.EXTYLES.1">1</a>). A 10:1 molar ratio of IAC to SCN-Bz-DOTA appeared to give a quantitative yield of the IAC-SCN-Bz-DOTA conjugate. The authors suggested that the product formed was a 1:1 conjugate because the primary amine was the only reactive functional group at pH 8.4. This conjugate was purified with a Sep-Pak C-18 cartridge and then incubated with <sup>111</sup>In-chloride in an aqueous solution (pH 5) of 0.23 M sodium acetate and 0.015 M sodium ascorbate at 75ºC for 1 h. The final radioligand was purified with a Sep-Pak C-18 cartridge. The labeling yield was >80%. The specific activity was calculated to be >7.5 kBq/pmol (202.7 Ci/mmol). Preparations with >95% radiochemical purity were used for <i>in vitro</i> and <i>in vivo</i> studies.</p></div><div id="IAC111In.In_Vitro_Studies_Tes"><h2 id="_IAC111In_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD))+AND+in+vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Burnett et al. (<a class="bk_pop" href="#IAC111In.EXTYLES.9">9</a>) used the enzyme-linked immunosorbent assay to determine the IC<sub>50</sub> of unlabeled IAC to be 2.94 nM. <i>In vitro</i> binding assays of IAC-SCN-Bz-DOTA-<sup>111</sup>In were performed with purified human α<sub>v</sub>β<sub>3</sub> protein (molecular weight = 237,000) (<a class="bk_pop" href="#IAC111In.EXTYLES.1">1</a>). The binding was assessed by size-exclusion high-performance liquid chromatography to detect the shift to a higher molecular weight peak that was identical to the integrin α<sub>v</sub>β<sub>3</sub> protein. The percent bound of IAC-SCN-Bz-DOTA-<sup>111</sup>In was 6%, 40%, and 72% when incubated with 0.08 μM, 0.4 μM, and 0.8 μM integrin α<sub>v</sub>β<sub>3</sub>, respectively. This binding was completely blocked by a 25-fold molar excess of unlabeled IA. The authors reported that IAC-SCN-Bz-DOTA-<sup>111</sup>In was stable in serum for 18 h at 37ºC.</p></div><div id="IAC111In.Animal_Studies"><h2 id="_IAC111In_Animal_Studies_">Animal Studies</h2><div id="IAC111In.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The <i>in vivo</i> tumor accumulation, distribution, and gamma imaging of IAC-SCN-Bz-DOTA-<sup>111</sup>In were studied in nude mice bearing s.c. human M21 melanomas (~0.5 cm<sup>3</sup>) in the right flanks (<a class="bk_pop" href="#IAC111In.EXTYLES.1">1</a>). Unlabeled IAC was added to the radioligand to achieve the specific activity of 85 kBq/<160 pmol (2.30 μCi/<160 pmol) so that each mouse received 160 pmol of total IAC. The radioligand was rapidly cleared from the circulation <i>via</i> the renal system. The tumor radioactivity levels (<i>n</i> = 4–5) were 5.58 ± 1.43% injected dose per gram (ID/g) (20 min), 5.34 ± 0.60% ID/g (60 min), and 4.47 ± 0.66% ID/g (120 min). In most major organs (except the lung and kidney), the tumor/organ ratios at 20 min were all >1. The tumor/blood ratios were 2.36 ± 0.64 (20 min), 4.69 ± 1.30 (60 min), and 9.74 ± 1.00 (120 min). The tumor/muscle ratios were 4.99 ± 1.46 (20 min), 7.07 ± 1.48 (60 min), and 9.87 ± 1.22 (120 min). The tumor/kidney ratios were 0.19 ± 0.07 (20 min), 0.37 ± 0.07 (60 min), and 0.78 ± 0.12 (120 min). The tumor/liver ratios were 1.58 ± 0.60 (20 min), 1.79 ± 0.31 (60 min), and 2.26 ± 0.35 (120 min). The tumor/intestine ratios were 1.01 ± 0.38 (20 min), 1.00 ± 0.15 (60 min), and 0.92 ± 0.13 (120 min). In a blocking study, 200 μg of unlabeled IA was co-injected with <sup>111</sup>In-SCN-Bz-DOTA-IAC. At 60 min after injection, the tumor radioactivity level was decreased from 5.3 ± 0.6% ID/g to 1.4 ± 0.3% ID/g. The radioactivity levels in most other organs were also significantly decreased. Co-injection of 30 mg <span class="small-caps">l</span>-lysine did not decrease either the tumor or kidney radioactivity level. The static posterior gamma imaging of the mice at 4 h after injection clearly visualized the tumor, and this visualization remained for 72 h. The abdomen and bladder areas were visualized at 4 h but gradually cleared out. With co-injection of 200 μg unlabeled IA, the tumor was not distinguished from the surrounding background radioactivity.</p></div><div id="IAC111In.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD))+AND+(dog+OR+rabbit+OR+pig+OR+sheep)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="IAC111In.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD))+AND+(primate+NOT+human)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="IAC111In.Human_Studies"><h2 id="_IAC111In_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((radiolabeled+IAC)+OR+(peptidomimetic+antagonist+for+imaging+of+RGD))+AND+human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="IAC111In.NIH_Support"><h2 id="_IAC111In_NIH_Support_">NIH Support</h2><p>NIH Intramural Support.</p></div><div id="IAC111In.references"><h2 id="_IAC111In_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.1">Jang B.S. , Lim E. , Hee Park S. , Shin I.S. , Danthi S.N. , Hwang I.S. , Le N. , Yu S. , Xie J. , Li K.C. , Carrasquillo J.A. , Paik C.H. Radiolabeled high affinity peptidomimetic antagonist selectively targets alpha(v)beta(3) receptor-positive tumor in mice. <span><span class="ref-journal">Nucl Med Biol. </span>2007;<span class="ref-vol">
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<strong>34</strong>
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</span>(4):363–70.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17499725" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17499725</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.2">Jin H. , Varner J. Integrins: roles in cancer development and as treatment targets. <span><span class="ref-journal">Br J Cancer. </span>2004;<span class="ref-vol">
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<strong>90</strong>
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||
</span>(3):561–5.</span> [<a href="/pmc/articles/PMC2410157/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2410157</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/14760364" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14760364</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.3">Paulhe F. , Manenti S. , Ysebaert L. , Betous R. , Sultan P. , Racaud-Sultan C. Integrin function and signaling as pharmacological targets in cardiovascular diseases and in cancer. <span><span class="ref-journal">Curr Pharm Des. </span>2005;<span class="ref-vol">
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||
<strong>11</strong>
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||
</span>(16):2119–34.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15974963" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15974963</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.4">Hood J.D. , Cheresh D.A. Role of integrins in cell invasion and migration. <span><span class="ref-journal">Nat Rev Cancer. </span>2002;<span class="ref-vol">
|
||
<strong>2</strong>
|
||
</span>(2):91–100.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12635172" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12635172</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.5">Hwang R. , Varner J. The role of integrins in tumor angiogenesis. <span><span class="ref-journal">Hematol Oncol Clin North Am. </span>2004;<span class="ref-vol">
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||
<strong>18</strong>
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||
</span>(5):991–1006.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15474331" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15474331</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.6">Cai W. , Shin D.W. , Chen K. , Gheysens O. , Cao Q. , Wang S.X. , Gambhir S.S. , Chen X. Peptide-labeled near-infrared quantum dots for imaging tumor vasculature in living subjects. <span><span class="ref-journal">Nano Lett. </span>2006;<span class="ref-vol">
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||
<strong>6</strong>
|
||
</span>(4):669–76.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16608262" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16608262</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.7">Massoud T.F. , Gambhir S.S. Molecular imaging in living subjects: seeing fundamental biological processes in a new light. <span><span class="ref-journal">Genes Dev. </span>2003;<span class="ref-vol">
|
||
<strong>17</strong>
|
||
</span>(5):545–80.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12629038" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12629038</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.8">Haubner R. , Wester H.J. Radiolabeled tracers for imaging of tumor angiogenesis and evaluation of anti-angiogenic therapies. <span><span class="ref-journal">Curr Pharm Des. </span>2004;<span class="ref-vol">
|
||
<strong>10</strong>
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</span>(13):1439–55.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15134568" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15134568</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.9">Burnett C.A. , Xie J. , Quijano J. , Shen Z. , Hunter F. , Bur M. , Li K.C. , Danthi S.N. Synthesis, in vitro, and in vivo characterization of an integrin alpha(v)beta(3)-targeted molecular probe for optical imaging of tumor. <span><span class="ref-journal">Bioorg Med Chem. </span>2005;<span class="ref-vol">
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<strong>13</strong>
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</span>(11):3763–71.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15863003" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15863003</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.10">Duggan M.E. , Duong L.T. , Fisher J.E. , Hamill T.G. , Hoffman W.F. , Huff J.R. , Ihle N.C. , Leu C.T. , Nagy R.M. , Perkins J.J. , Rodan S.B. , Wesolowski G. , Whitman D.B. , Zartman A.E. , Rodan G.A. , Hartman G.D. Nonpeptide alpha(v)beta(3) antagonists. 1. Transformation of a potent, integrin-selective alpha(IIb)beta(3) antagonist into a potent alpha(v)beta(3) antagonist. <span><span class="ref-journal">J Med Chem. </span>2000;<span class="ref-vol">
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<strong>43</strong>
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</span>(20):3736–45.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11020288" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11020288</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="IAC111In.EXTYLES.11">Hood J.D. , Bednarski M. , Frausto R. , Guccione S. , Reisfeld R.A. , Xiang R. , Cheresh D.A. Tumor regression by targeted gene delivery to the neovasculature. <span><span class="ref-journal">Science. </span>2002;<span class="ref-vol">
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<strong>296</strong>
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</span>(5577):2404–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12089446" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12089446</span></a>]</div></dd></dl></div><div><dl class="temp-labeled-list small"><dt></dt><dd><div><p class="no_top_margin"><div>This MICAD chapter is not included in the Open Access Subset, because it was authored / co-authored by one or more investigators who was not a member of the MICAD staff.</div></p></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: NBK23033</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641240" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641240</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/TrastFab111In/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/mIgGtat111In/" 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/NBK23033/?report=reader">PubReader</a></li><li><a href="/books/NBK23033/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23033" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23033" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT, Paik CH, Danthi N. 4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(S)-[N-3-amino-(SCN-Bz-DOTA-111In)-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine. 2007 Jul 9 [Updated 2007 Dec 18]. 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/NBK23033/pdf/Bookshelf_NBK23033.pdf">PDF version of this page</a> (391K)</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="#IAC111In.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#IAC111In.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#IAC111In.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#IAC111In.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#IAC111In.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#IAC111In.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#IAC111In.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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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> 4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(S)-[N-3-amino-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea.</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> 4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(S)-[N-3-amino-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea.<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, Danthi N, Xie J. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" 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<a href="https://www.nlm.nih.gov/careers/careers.html" class="text-white">Careers</a></p>
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