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<title>4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(S)-[N-3-amino-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea - 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="#__NBK23158_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23158_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/sosfluoresceinisothiocy/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Fluorescin-CLT/" 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="_NBK23158_"><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-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">FITC-IAC</div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD, <span itemprop="author">Narasimhan Danthi</span>, PhD, and <span itemprop="author">Jianwu Xie</span>, MD.</p><a data-jig="ncbitoggler" href="#__NBK23158_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23158_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">Narasimhan Danthi</span>, PhD<div class="affiliation small">
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Department of Radiology, 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.cc@ihtnaDN" class="oemail">vog.hin.cc@ihtnaDN</a>
|
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Jianwu Xie</span>, MD<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@eixj" class="oemail">vog.hin.cc@eixj</a>
|
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</div></div></div><p class="small">Created: <span itemprop="datePublished">October 9, 2007</span>; Last Update: <span itemprop="dateModified">January 2, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="FITC-IAC.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23158/table/FITC-IAC.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__FITC-IAC.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-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea</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/46488337" 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=46488337" alt="image 46488337 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>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">FITC-IAC</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
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<b>Synonym:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Fluorescein-IAC</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Agent Category:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Compound</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Target:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Integrin α<sub>v</sub>β<sub>3</sub></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Target Category:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Receptor binding</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Method of detection:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Optical fluorescence imaging</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Source of contrast /signal:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Fluorescein isothiocyanate (FITC)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Activation:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Studies:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
|
||
<i>In vitro</i>
|
||
|
||
</div></li></ul>
|
||
<ul class="simple-list"><li class="half_rhythm"><div>
|
||
<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
|
||
</div></li></ul>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on 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="FITC-IAC.Background"><h2 id="_FITC-IAC_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(FITC-IAC)+OR+(optical+integrin+molecular+probe)&WebEnv=0PS1fLXZBnvnrxKjSnwgcbGF1ahtg1sHgmlU4DnQtSGhFnLeIKjsNo85f5or1goSzsM4vuKLKsfafr%40256128CE704ECD70_0127SID&WebEnvRq=1" 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-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea (FITC-IAC) is an integrin-targeted molecular imaging agent conjugated with fluorescein isothiocyanate (FITC) that was developed for fluorescence imaging of tumor vasculature and tumor angiogenesis (<a class="bk_pop" href="#FITC-IAC.EXTYLES.1">1</a>). FITC is a fluorochrome with a peak excitation wavelength of 495 nm and a peak emission wavelength of 519 nm.</p><p>Cellular survival, invasion, and migration control embryonic development, angiogenesis, tumor metastasis, and other physiological processes (<a class="bk_pop" href="#FITC-IAC.EXTYLES.2">2</a>, <a class="bk_pop" href="#FITC-IAC.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="#FITC-IAC.EXTYLES.4">4</a>, <a class="bk_pop" href="#FITC-IAC.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="#FITC-IAC.EXTYLES.6">6</a>, <a class="bk_pop" href="#FITC-IAC.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="#FITC-IAC.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="#FITC-IAC.EXTYLES.1">1</a>, <a class="bk_pop" href="#FITC-IAC.EXTYLES.9">9</a>, <a class="bk_pop" href="#FITC-IAC.EXTYLES.10">10</a>). Duggan et al. (<a class="bk_pop" href="#FITC-IAC.EXTYLES.9">9</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. Optical imaging is an imaging method that utilizes light photons emitted from bioluminescence and fluorescence probes (<a class="bk_pop" href="#FITC-IAC.EXTYLES.7">7</a>). Depth penetration is a major limiting factor for <i>in vivo</i> optical imaging. Currently, <i>in vivo</i> optical imaging has wide applications in small animal imaging but only limited applications in large animal and human studies (<a class="bk_pop" href="#FITC-IAC.EXTYLES.11">11</a>). Fluorescent dyes conjugated RGD peptides such as <a href="/books/n/micad/RGDyK-Cy55/">Cy5.5-c(RGDyK),</a><a href="/books/n/micad/Cy7TetramericRGD/">Cy7-E{E(c(RGDyK)]<sub>2</sub>}<sub>2</sub></a>, and <a href="/books/n/micad/Cypate-GRD/">Cyp-GRD</a> have been shown to visualize subcutaneously implanted integrin α<sub>v</sub>β<sub>3</sub>−positive tumors (<a class="bk_pop" href="#FITC-IAC.EXTYLES.12">12-15</a>). 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 an inhibition concentration (IC<sub>50</sub>) of 0.04 μM and was used by Hood et al. (<a class="bk_pop" href="#FITC-IAC.EXTYLES.10">10</a>) to covalently couple to a cationic nanoparticle for targeted gene therapy, Burnett et al. (<a class="bk_pop" href="#FITC-IAC.EXTYLES.1">1</a>) designed and synthesized a series of aliphatic carbamate derivatives with enhanced binding affinity. The peptidomimetic <a href="/books/n/micad/IAC111In/">IAC</a> ligand was successfully conjugated to FITC 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.</p></div><div id="FITC-IAC.Synthesis"><h2 id="_FITC-IAC_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((FITC-IAC)+OR+(optical+integrin+molecular+probe))+AND+synthesis&WebEnv=0rwFEHxsYPnbUo9DQ0DdszMOtD8TeQumh5Ni9E6nSiqBBhn0QCKyWZ0TZTkTTCfBYG4LYTx9BokMfe%40256128CE704ECD70_0127SID&WebE" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Burnett et al. (<a class="bk_pop" href="#FITC-IAC.EXTYLES.1">1</a>) reported the synthesis of FITC-IAC from commercially available 3-amino neopentanol. 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 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. <i>N</i>,<i>N</i>-diisopropylethylamine was added to this ligand in anhydrous dimethyl sulfoxide. One molar equivalent of FITC was then added, and the reaction mixture was stirred under argon at 40ºC for 18 h. The final FITC-IAC was purified by high-performance liquid chromatography with a yield of 24%. The identity of FITC-IAC was confirmed by (<sup>1</sup>H and <sup>13</sup>C) nuclear magnetic resonance and high-resolution mass spectrometry.</p></div><div id="FITC-IAC.In_Vitro_Studies_Tes"><h2 id="_FITC-IAC_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=((FITC-IAC)+OR+(optical+integrin+molecular+probe))+AND+in+vitro&WebEnv=0gV_gXuYCuJ9eAFu8yPqkyDK4CC-rnqaaZ0stqrfdwH2JWJ2-zxfMh5z0-Gk87AJm3ScM3SFm5FT66%40256128CE704ECD70_0127SID&WebEn" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>An <i>in vitro</i> binding affinity assay of FITC-IAC was performed with purified human α<sub>v</sub>β<sub>3</sub> integrin in ELISA assays and α<sub>v</sub>β<sub>3</sub>-expressing M21 melanoma cells in cell adhesion assays (<a class="bk_pop" href="#FITC-IAC.EXTYLES.1">1</a>). The natural ligand vitronectin was used as the competing ligand. The IC<sub>50</sub> of FITC-IAC was determined to be 3.4 ± 0.33 nM (<i>n</i> = 3). In comparison, the IA and IAC had IC<sub>50</sub> values of 14.1 ± 1.4 nM and 2.94 ± 0.19 nM, respectively. Inhibition of cell adhesion of FITC-IAC was similar to that of IA. Comparing results with other neopentyl derivatives in the same study, the authors (<a class="bk_pop" href="#FITC-IAC.EXTYLES.1">1</a>) suggested that the geminal methyl groups favored interaction with the receptor. The cellular distribution of FITC-IAC in the M21 cells was also examined by fluorescence microscopy. The study suggested that the fluorescence signal came from the cell membrane surface after 5 min of incubation.</p></div><div id="FITC-IAC.Animal_Studies"><h2 id="_FITC-IAC_Animal_Studies_">Animal Studies</h2><div id="FITC-IAC.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(FITC-IAC)+OR+(optical+integrin+molecular+probe)&WebEnv=0r1FTnf-vTnG5gMST0UR2YcRt5scStCmvUglA86Js-ejohSrROSWWIWglyxTzdUiDy47kdd-_oMp2U%40256128CE704ECD70_0127SID&WebEnvRq=1" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The <i>in vivo</i> tumor accumulation, distribution, and optical imaging of FITC-IAC were studied in mice bearing M21 tumors in the right flanks. Each mouse received 100 μl (6 mg/ml) by i.v. administration. Tumors and various tissues were excised for counting at 30 min and 4 h. The fluorescence signal rapidly showed up in the tumor with marked signal intensity at 30 min compared to other organs. By qualitative analysis, the tumor signal intensity was ~3 times that found in the liver and muscle and ~8 times that found in the heart. The tumor signal intensity decreased but remained pronounced at 4 h when the liver also showed decreased signal intensity. The tumor intensity was ~4 times that found in the liver. Very low signal intensity was observed in the kidney, spleen, and lung at all times. However, the muscle intensity remained high at 4 h, and the tumor signal intensity was only ~1.6 times that of the muscle intensity (extrapolated from Figure 3). No blocking experiments were performed. To further study the exact location of FITC-IAC accumulation, rhodamine-lectin was injected 2 h after FITC-IAC administration to delineate the vessels. Fluorescence microscopy of tumor tissue sections suggested intracellular accumulation of the FITC label in the tumor cells.</p></div><div id="FITC-IAC.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((FITC-IAC)+OR+(optical+integrin+molecular+probe))+AND+(dog+OR+rabbit+OR+pig+OR+sheep)&WebEnv=0n3NU8XMvbGQaEfWvIDUQfbpRlXR9rgTARNiMIyFfKKG2b3KCHAr3CurrQoD1Pm85QF7kT8YxQFeDH%40256128C" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FITC-IAC.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((FITC-IAC)+OR+(optical+integrin+molecular+probe))+AND+(primate+NOT+human)&WebEnv=04Vqr1hip6uLN49s8qxuH3YnMVVGoskEo1ki6UD3qpyxzGfyoLUoOnjMKR5KVcocEsZ6z6L2OMN_kk%40256128CE704ECD70_01" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="FITC-IAC.Human_Studies"><h2 id="_FITC-IAC_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((FITC-IAC)+OR+(optical+integrin+molecular+probe))+AND+human&WebEnv=0xLUUT8XoosP_UiviGM-_f4yQYD1ZBEGyTu5x3H3y6y6oJFvXKY217gaAVcEKMgHVF_IDUHVHI6GHa%40256128CE704ECD70_0127SID&WebEnvRq" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FITC-IAC.NIH_Support"><h2 id="_FITC-IAC_NIH_Support_">NIH Support</h2><p>NIH intramural support.</p></div><div id="FITC-IAC.references"><h2 id="_FITC-IAC_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.1">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">
|
||
<strong>13</strong>
|
||
</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>2.</dt><dd><div class="bk_ref" id="FITC-IAC.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">
|
||
<strong>90</strong>
|
||
</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="FITC-IAC.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">
|
||
<strong>11</strong>
|
||
</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="FITC-IAC.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="FITC-IAC.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">
|
||
<strong>18</strong>
|
||
</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="FITC-IAC.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">
|
||
<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="FITC-IAC.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="FITC-IAC.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>
|
||
</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="FITC-IAC.EXTYLES.9">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">
|
||
<strong>43</strong>
|
||
</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>10.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.10">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">
|
||
<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><dt>11.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.11">Bremer C. , Ntziachristos V. , Weissleder R. Optical-based molecular imaging: contrast agents and potential medical applications. <span><span class="ref-journal">Eur Radiol. </span>2003;<span class="ref-vol">
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<strong>13</strong>
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</span>(2):231–43.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12598985" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12598985</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.12">Wang W. , Ke S. , Wu Q. , Charnsangavej C. , Gurfinkel M. , Gelovani J.G. , Abbruzzese J.L. , Sevick-Muraca E.M. , Li C. Near-infrared optical imaging of integrin alphavbeta3 in human tumor xenografts. <span><span class="ref-journal">Mol Imaging. </span>2004;<span class="ref-vol">
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<strong>3</strong>
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</span>(4):343–51.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15802051" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15802051</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.13">Kwon S. , Ke S. , Houston J.P. , Wang W. , Wu Q. , Li C. , Sevick-Muraca E.M. Imaging dose-dependent pharmacokinetics of an RGD-fluorescent dye conjugate targeted to alpha v beta 3 receptor expressed in Kaposi's sarcoma. <span><span class="ref-journal">Mol Imaging. </span>2005;<span class="ref-vol">
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<strong>4</strong>
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</span>(2):75–87.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16105505" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16105505</span></a>]</div></dd><dt>14.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.14">Achilefu S. , Bloch S. , Markiewicz M.A. , Zhong T. , Ye Y. , Dorshow R.B. , Chance B. , Liang K. Synergistic effects of light-emitting probes and peptides for targeting and monitoring integrin expression. <span><span class="ref-journal">Proc Natl Acad Sci U S A. </span>2005;<span class="ref-vol">
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<strong>102</strong>
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</span>(22):7976–81.</span> [<a href="/pmc/articles/PMC1142399/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1142399</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/15911748" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15911748</span></a>]</div></dd><dt>15.</dt><dd><div class="bk_ref" id="FITC-IAC.EXTYLES.15">Chen X. , Conti P.S. , Moats R.A. In vivo near-infrared fluorescence imaging of integrin alphavbeta3 in brain tumor xenografts. <span><span class="ref-journal">Cancer Res. </span>2004;<span class="ref-vol">
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<strong>64</strong>
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</span>(21):8009–14.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15520209" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15520209</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: NBK23158</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641361" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641361</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/sosfluoresceinisothiocy/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Fluorescin-CLT/" 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/NBK23158/?report=reader">PubReader</a></li><li><a href="/books/NBK23158/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23158" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23158" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT, Danthi N, Xie J. 4-[2-(3,4,5,6-Tetrahydropyrimidin-2-ylamino)ethyloxy]benzoyl-2-(S)-[N-3-amino-neopenta-1-carbamyl)]-aminoethylsulfonylamino-β-alanine fluorescein thiourea. 2007 Oct 9 [Updated 2008 Jan 2]. 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/NBK23158/pdf/Bookshelf_NBK23158.pdf">PDF version of this page</a> (393K)</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="#FITC-IAC.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#FITC-IAC.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#FITC-IAC.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#FITC-IAC.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#FITC-IAC.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#FITC-IAC.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#FITC-IAC.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:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-d-Phe-Lys)](4) peptide.<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, Garanger E, Josserand V, Jin Z, Foillard S, Boturyn D, Favrot PMC, Dumy P, Coll JL. </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/20641993" 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> VivoTag-S680–conjugated 3-aminomethyl α(v)β(3) antagonist derivative for 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