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<title>Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-d-Phe-Lys)]4 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="Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-d-Phe-Lys)]4 peptide" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2007/12/28" /><meta name="citation_author" content="Kenneth T. Cheng" /><meta name="citation_author" content="Elisabeth Garanger" /><meta name="citation_author" content="Veronique Josserand" /><meta name="citation_author" content="Zhaohui Jin" /><meta name="citation_author" content="Stephanie Foillard" /><meta name="citation_author" content="Didier Boturyn" /><meta name="citation_author" content="Pr Marie C. 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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="#__NBK23355_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23355_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/LP-1/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/tAB50-Cy5/" 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="_NBK23355_"><span class="title" itemprop="name">Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-<span class="small-caps">d</span>-Phe-Lys)]<sub>4</sub> peptide </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">Cy5-RAFT-c(-RGDfK-)<sub>4</sub></div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD, <span itemprop="author">Elisabeth Garanger</span>, PhD, <span itemprop="author">Veronique Josserand</span>, PhD, <span itemprop="author">Zhaohui Jin</span>, PhD, <span itemprop="author">Stephanie Foillard</span>, BS, <span itemprop="author">Didier Boturyn</span>, PhD, <span itemprop="author">Pr Marie C. Favrot</span>, PhD, <span itemprop="author">Pascal Dumy</span>, PhD, and <span itemprop="author">Jean-Luc Coll</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23355_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23355_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">Elisabeth Garanger</span>, PhD<div class="affiliation small">
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INSERM U823, Institut Albert Bonniot, 38706 La Tronche, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="moc.liamg@regnarag.e" class="oemail">moc.liamg@regnarag.e</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Veronique Josserand</span>, PhD<div class="affiliation small">
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INSERM U823, Institut Albert Bonniot, 38706 La Tronche, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="rf.elbonerg-fju@dnaressoj.euqinoreV" class="oemail">rf.elbonerg-fju@dnaressoj.euqinoreV</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Zhaohui Jin</span>, PhD<div class="affiliation small">
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INSERM U823, Institut Albert Bonniot, 38706 La Tronche, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="moc.oohay@76iuhoahzniJ" class="oemail">moc.oohay@76iuhoahzniJ</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Stephanie Foillard</span>, BS<div class="affiliation small">
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UMR CNRS 5250, Universite Joseph Fourier, 38041 Grenoble, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="rf.elbonerg-fju@dralliof.einahpetS" class="oemail">rf.elbonerg-fju@dralliof.einahpetS</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Didier Boturyn</span>, PhD<div class="affiliation small">
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UMR CNRS 5250, Universite Joseph Fourier, 38041 Grenoble, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="rf.elbonerg-fju@nyrutob.reidiD" class="oemail">rf.elbonerg-fju@nyrutob.reidiD</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Pr Marie C. Favrot</span>, PhD<div class="affiliation small">
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INSERM U823, Institut Albert Bonniot, 38706, La Tronche, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="rf.elbonerg-uhc@torvaFCM" class="oemail">rf.elbonerg-uhc@torvaFCM</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Pascal Dumy</span>, PhD<div class="affiliation small">
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UMR CNRS 5250, Universite Joseph Fourier, 38041 Grenoble, France,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="rf.elbonerg-fju@ymud.lacsaP" class="oemail">rf.elbonerg-fju@ymud.lacsaP</a>
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</div></div><div class="contrib half_rhythm"><span itemprop="author">Jean-Luc Coll</span>, PhD<div class="affiliation small">
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INSERM U823, Institut Albert Bonniot, 38706 La Tronche, France, 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=".rf.elbonerg-fju@lloC.cuL-naeJ" class="oemail">.rf.elbonerg-fju@lloC.cuL-naeJ</a>
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</div></div></div><p class="small">Created: <span itemprop="datePublished">October 9, 2007</span>; Last Update: <span itemprop="dateModified">December 28, 2007</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="CyRAFTRGD.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23355/table/CyRAFTRGD.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__CyRAFTRGD.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;">Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-<span class="small-caps">d</span>-Phe-Lys)]<sub>4</sub> peptide</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/26744433" 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=26744433" alt="image 26744433 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;">Cy5-RAFT-c(-RGDfK-)<sub>4</sub></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;">Cy5-RAFT-RGD, (Cy5)RAFT(c[-RGDfK-])<sub>4</sub></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;">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;">Optical, near-infrared (NIR) fluorescence 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;">Cyanine-5 (Cy5)</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="CyRAFTRGD.Background"><h2 id="_CyRAFTRGD_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-<span class="small-caps">d</span>-Phe-Lys)]<sub>4</sub> peptide (Cy5-RAFT-c(-RGDfK-)<sub>4</sub>) is an integrin-targeted molecular imaging agent developed for near-infrared (NIR) fluorescence imaging of tumor vasculature and tumor angiogenesis (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.1">1</a>, <a class="bk_pop" href="#CyRAFTRGD.EXTYLES.2">2</a>). Cyanine-5 (Cy5) is a fluorophore with a maximal absorption (Abs<sub>max</sub>) wavelength of 649 nm and a maximal emission (Em<sub>max</sub>) wavelength of 670 nm (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.3">3</a>). The molar extinction coefficient (є) is 250,000 M−<sup>1</sup>cm−<sup>1</sup>, and the quantum yield (QY) is >0.28.</p><p>Cellular survival, invasion, and migration control embryonic development, angiogenesis, tumor metastasis, and other physiologic processes (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.4">4</a>, <a class="bk_pop" href="#CyRAFTRGD.EXTYLES.5">5</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="#CyRAFTRGD.EXTYLES.6">6</a>, <a class="bk_pop" href="#CyRAFTRGD.EXTYLES.7">7</a>). These transmembrane glycoproteins consist of two noncovalently associated subunits, α and β, 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 unregulated in certain types of tumor cells and in almost all tumor vasculature. Molecular imaging probes carrying the RGD motif that binds to 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="#CyRAFTRGD.EXTYLES.8">8</a>, <a class="bk_pop" href="#CyRAFTRGD.EXTYLES.9">9</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="#CyRAFTRGD.EXTYLES.10">10</a>). Optical imaging utilizes light photons emitted from bioluminescence and fluorescence probes (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.9">9</a>). Depth penetration is one major limiting factor in <i>in vivo</i> optical imaging. Currently, <i>in vivo</i> optical imaging has wide applications in small animal studies but only limited applications in large animal and human studies (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.11">11</a>). NIR fluorescence imaging (light range, 650−900 nm) has the advantages of relatively higher tissue penetration and lower autofluorescence from nontarget tissue. NIR fluorescent dyes are conjugated RGD peptides such as <a href="/books/n/micad/RGDyK-Cy55/">Cy5.5-c(RGDyK),</a> Cy5.5-c(RGDfK), and <a href="/books/n/micad/Cypate-GRD/">Cyp-RGD</a>, which have been shown to visualize subcutaneously implanted integrin α<sub>v</sub>β<sub>3</sub>−positive tumors (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.12">12-15</a>). Improved biophysical and pharmacodynamic properties of these RGD peptides appear to greatly augment their performance as molecular imaging probes (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.1">1</a>). Multivalent presentation appears to be one of the possible approaches that can improve these properties. Boturyn et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.16">16</a>) generated a versatile molecular RAFT platform with a cyclic decapeptide [c(-Lys(Boc)-Lys(Alloc)-Lys(Boc)-Pro-Gly-Lys(Boc)-Lys(Alloc)-Lys(Boc)-Pro-Gly-)] that forms a ring with two faces. The RAFT platform is used as a suitable scaffold to independently and separately direct the cyclopentapeptide ligands and the reporter groups. The upper face is linked to four copies of the c(RGDfK) peptide for integrin α<sub>v</sub>β<sub>3</sub> targeting, and the bottom face is linked to Cy5 for NIR imaging. Garanger et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.17">17</a>) reported that Cy5-RAFT-c(-RGDfK-)<sub>4</sub> efficiently accumulated into tumors in nude mice. Jin et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.1">1</a>) showed that Cy5-RAFT-c(-RGDfK-)<sub>4</sub> could allow <i>in vivo</i> optical imaging of subcutaneous and intraperitoneal tumors in nude mice.</p></div><div id="CyRAFTRGD.Synthesis"><h2 id="_CyRAFTRGD_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%29%29%20AND%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Boturyn et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.16">16</a>) described the three-step synthesis of RAFT-c(-RGDfK-)<sub>4</sub>. The first step was the solid-phase peptide synthesis of linear protected peptide fragments by the standard Fmoc/<i>t</i>Bu solid-phase chemistry on an acid-labile Sasrin resin. This was followed by cyclization in solution to provide the corresponding templates and cyclopentapeptides. The head-to-tail cyclization was performed in <i>N</i>,<i>N</i>-dimethylformamide under high dilution with the PyBOP reagent. The second step consisted of the sequential deprotection-functionalization of a lysine side chain with label molecules and subsequently four aminooxy groups on the template’s face, as well as the functionalization of the lysine side chain on the cyclopentapeptides by a glyoxylyl group. The third step was the final oxime ligation of deprotected aminooxy-containing RAFT molecules and <i>N</i>-glyoxylyl-lysyl cyclopentapeptides. Protection of the lysine in position 1, 3, 6, or 8 and of the two lysines in positions 2 and 7 resulted in RAFT molecules that have two orthogonally addressable domains pointing on either side of the cyclopeptide backbone (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.1">1</a>). On the upper face, four copies of the cyclo-(RGD-<span class="small-caps">d</span>-Phe-Lys) [c(RGDfK)] peptide were grafted for recognition of the integrin <i>via</i> chemoselective oxime ligation (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.17">17</a>). The conjugation was achieved from RAFT(ONH<sub>2</sub>)<sub>4</sub>, an aminooxy-functionalized RAFT intermediate, and cyclo-[RGDfK(COCHO)], which are glyoxylyl-functionalized monomers. The four c(RGDfK) motifs were linked on the RAFT using an oxime bond (R1-O-N=C-R2). During synthesis, the chemoselective ligation step followed the covalent attachment of the lower face of the RAFT with one or two reporter groups. The Cy5-<i>N</i>-hydroxysuccinimide ester was used to introduce the Cy5 label at the last step to minimize the loss of fluorochrome. The final product was purified by high-performance liquid chromatography with yields of the reactions ranging from 51% to 95% after purification steps. The peptide conjugate was identified by the mass spectrum (ES-MS, positive mode).</p></div><div id="CyRAFTRGD.In_Vitro_Studies_Tes"><h2 id="_CyRAFTRGD_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%28Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%29%29%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Jin et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.1">1</a>) performed <i>in vitro</i> cell binding studies in human ovarian adenocarcinoma IGROV1 cells. These cells were found to express low to moderate levels of integrin α<sub>v</sub>β<sub>3</sub> and remained integrin α<sub>v</sub>β<sub>3</sub>–positive after inoculation and proliferation in nude mice. Confocal laser scanning microscopy (CLSM) images confirmed the binding of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> to IGROV1 cells after incubation at 37ºC for 30 min. Negligible signals were observed when the cells were pretreated with the unlabeled RAFT-c(-RGDfK-)<sub>4</sub> ligand.</p><p>Jin et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.2">2</a>) studied the <i>in vitro</i> binding of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> to human embryonic kidney HEK293 (β<sub>3</sub>) andHEK293( β<sub>1</sub>) cells which were stable transfectants of human β<sub>3</sub> and β<sub>1</sub> subunit <sub>,</sub> respectively. H293 (β<sub>3</sub>) cells expressed high levels of α<sub>v</sub>β<sub>3</sub> while the HEK293( β<sub>1</sub>) cells expressed only α<sub>v</sub>β<sub>1</sub> but no α<sub>v</sub>β<sub>3</sub>. Cy5-RAFT-c(-RGDfK-)<sub>4</sub> reacted very strongly with HEK293 (β<sub>3</sub>) cells.</p></div><div id="CyRAFTRGD.Animal_Studies"><h2 id="_CyRAFTRGD_Animal_Studies_">Animal Studies</h2><div id="CyRAFTRGD.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%29%29%20AND%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Garanger et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.17">17</a>) reported that Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was able to target tumor angiogenesis. After i.v. injection of 10 nmol of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> in mice bearing s.c. Ts/Apc tumors, the tumors were brightly stained. The Cy5 signal increased during the first hour and then decreased slowly over time. The tumor accumulation was maximal at 1 h and could still be detected during the first 20 h. The conjugated peptide appeared to diffuse rapidly in all tissues and produced an intense background in the skin. There was a rapid clearance of the peptide by the kidneys. No staining came from the liver, lung, heart, or spleen. In nude mice bearing IGROV1 ovarian cancer nodules scattered in the peritoneal cavity, Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was able to detect and bind to disseminated IGROV1 nodules. When these nodules were removed and studied by a two-photon confocal microscope, there was a strong Cy5 signal in the tumor cells and the stromal endothelial cells. The cytoplasm was stained but the nuclei were not. The authors suggested that this staining pattern resembled that of immunostaining of the human integrin α<sub>v</sub>β<sub>3</sub>.</p><p>Jin et al. (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.1">1</a>) studied the <i>in vivo</i> imaging of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> in nude mice bearing s.c. IGROV1 tumors. After i.v. administration of 10 nmol of Cy5-RAFT-c(-RGDfK-)<sub>4</sub>, the probe accumulated strongly in the tumors within 5 min. The whole body also gave strong signal because of the presence of circulating fluorescent molecules. The tumor/skin ratio (<i>n</i> = 3) was improved to 3.24 ± 0.772 between 3 and 6 h and then slowly decreased at 24 h. In comparison, the ratios for the Cy5-labeled non-RGD peptide and Cy5-labeled monovalent RGD peptide were 1.44 ± 0.299 and 2.00 ± 0.179, respectively. For Cy5-RAFT-c(-RGDfK-)<sub>4</sub>, the tumor could still be visualized at 48 h. Strong signals were also observed in the kidney and bladder during the first 6 h. No significant difference was observed when the conjugated peptide was injected by i.p administration. A dose escalation study showed that the 10-nmol dose produced the strongest signal and the highest contrast when compared to doses of 0.2 and 2 nmol. Tumor samples taken 3 h after i.v. administration of 10 nmol Cy5-RAFT-c(-RGDfK-)<sub>4</sub> and analyzed by CLSM showed that the probe stained the endothelial cells of the tumor microvasculature as well as numerous tumor cells. In nude mice induced with deep and small IGROV1/pGL3 peritoneal tumors, the fluorescence signal of 30 nmol of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was colocalized with bioluminescent luciferase-positive nodules. The results were confirmed by CLSM on nodules obtained from the mice. In comparison, no specific signal was observed with the Cy5-labeled monovalent RGD peptide.</p><p>Whole body optical imaging was performed in nude mice bearing s.c. HEK293 (β<sub>1</sub>) tumors and HEK293 (β<sub>3</sub>) tumors (<a class="bk_pop" href="#CyRAFTRGD.EXTYLES.2">2</a>). Each mouse received an i.v. dose of 10 nmol of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> and then imaged for 2 days. The quantitative analysis showed that Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was taken up by the HEK293 (β<sub>3</sub>) tumors and reached a maximal signal level 5-30 min after injection. Between 0.5-3 h, the tumor signal levels remained very elevated from 65472 ± 90 to 61875 ± 3434 photons/pixel (<i>n</i> = 2-4). In comparison, the Cy5-cRGD monomer showed only 63744 ± 3031 to 28349 ± 9727 photons/pixel. The negative control probe RAFT-c(RβADfK-)<sub>4</sub> was rapidly washed out from the tumors. The tumor contrast (tumor/skin) for Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was 15.9 ± 3.6 at 4 h. In comparison, the Cy5-cRGD only showed a S/T value of 5.9 ± 2.0.The HEK293 (β<sub>1</sub>) tumors did not show any signal level with Cy5-RAFT-c(-RGDfK-)<sub>4</sub>. CLSM examination of tumors obtained from the studies at 3 or 24 h after injection showed that Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was massively internalized by HEK293 (β<sub>3</sub>) tumor cells and each tumor cell was strongly labeled at 3 h and still easily detected at 24 h. When a 300 nmol of blocking dose of unlabeled RAFT-c(-RGDfK-)<sub>4</sub> was coinjected with Cy5-RAFT-c(-RGDfK-)<sub>4</sub>, the tumor signal intensities of Cy5-RAFT-c(-RGDfK-)<sub>4</sub> was significantly reduced. At 3 h, the signal intensity was reduced by 80% from 65472 ± 80 to 12894 ± 2504. The kidney signal intensities were not affected by the blocking dose.</p></div><div id="CyRAFTRGD.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%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="CyRAFTRGD.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%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="CyRAFTRGD.Human_Studies"><h2 id="_CyRAFTRGD_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28%28Cy7-tetrameric%20RGD%29%20OR%20%28fluorescence%20imaging%20of%20RGD%29%29%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p><h3 id="NBK23355_footnotes">Footnotes</h3><dl class="temp-labeled-list small"><dt></dt><dd><div id="CyRAFTRGD.AFN9"><p class="no_top_margin"><sup>10</sup>Corresponding Author</p></div></dd></dl></div><div id="CyRAFTRGD.references"><h2 id="_CyRAFTRGD_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.1">Jin Z.H. , Josserand V. , Razkin J. , Garanger E. , Boturyn D. , Favrot M.C. , Dumy P. , Coll J.L. Noninvasive optical imaging of ovarian metastases using Cy5-labeled RAFT-c(-RGDfK-)4. <span><span class="ref-journal">Mol Imaging. </span>2006;<span class="ref-vol">
|
||
<strong>5</strong>
|
||
</span>(3):188–97.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16954034" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16954034</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.2">Jin Z.H. , Josserand V. , Foillard S. , Boturyn D. , Dumy P. , Favrot M.C. , Coll J.L. In vivo optical imaging of integrin alphaV-beta3 in mice using multivalent or monovalent cRGD targeting vectors. <span><span class="ref-journal">Mol Cancer. </span>2007;<span class="ref-vol">
|
||
<strong>6</strong>
|
||
</span>:41.</span> [<a href="/pmc/articles/PMC1906830/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1906830</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17565663" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17565663</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.3">Wohland T. , Friedrich K. , Hovius R. , Vogel H. Study of ligand-receptor interactions by fluorescence correlation spectroscopy with different fluorophores: evidence that the homopentameric 5-hydroxytryptamine type 3As receptor binds only one ligand. <span><span class="ref-journal">Biochemistry. </span>1999;<span class="ref-vol">
|
||
<strong>38</strong>
|
||
</span>(27):8671–81.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10393542" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10393542</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.4">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>5.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.5">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>6.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.6">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>7.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.7">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>8.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.8">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>9.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.9">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>10.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.10">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>11.</dt><dd><div class="bk_ref" id="CyRAFTRGD.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">
|
||
<strong>13</strong>
|
||
</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="CyRAFTRGD.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">
|
||
<strong>3</strong>
|
||
</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="CyRAFTRGD.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">
|
||
<strong>4</strong>
|
||
</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="CyRAFTRGD.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>
|
||
</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="CyRAFTRGD.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">
|
||
<strong>64</strong>
|
||
</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><dt>16.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.16">Boturyn D. , Coll J.L. , Garanger E. , Favrot M.C. , Dumy P. Template assembled cyclopeptides as multimeric system for integrin targeting and endocytosis. <span><span class="ref-journal">J Am Chem Soc. </span>2004;<span class="ref-vol">
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<strong>126</strong>
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||
</span>(18):5730–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15125666" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15125666</span></a>]</div></dd><dt>17.</dt><dd><div class="bk_ref" id="CyRAFTRGD.EXTYLES.17">Garanger E. , Boturyn D. , Jin Z. , Dumy P. , Favrot M.C. , Coll J.L. New multifunctional molecular conjugate vector for targeting, imaging, and therapy of tumors. <span><span class="ref-journal">Mol Ther. </span>2005;<span class="ref-vol">
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||
<strong>12</strong>
|
||
</span>(6):1168–75.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16051524" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16051524</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: NBK23355</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641556" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641556</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/LP-1/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/tAB50-Cy5/" 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/NBK23355/?report=reader">PubReader</a></li><li><a href="/books/NBK23355/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23355" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23355" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT, Garanger E, Josserand V, et al. Cy5-Regioselectively addressable functionalized template-[cyclo-(RGD-d-Phe-Lys)]4 peptide. 2007 Oct 9 [Updated 2007 Dec 28]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></div></div></li><li><a href="/books/NBK23355/pdf/Bookshelf_NBK23355.pdf">PDF version of this page</a> (157K)</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="#CyRAFTRGD.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#CyRAFTRGD.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#CyRAFTRGD.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#CyRAFTRGD.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#CyRAFTRGD.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#CyRAFTRGD.references" ref="log$=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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receptor-antibody OR antibody-receptor)">Receptors</option><option value="transporter">Transporters</option><option value="non-targeted">Non-targeted</option><option value=""nucleic acid"">Nucleic acids</option><option value="(non-targeted OR "unknown binding site")">Others</option></select></div></div><div><input id="__micad_btn_1" type="radio" name="stage" value="vitro" /><label for="__micad_btn_1"><i>In vitro</i></label><input id="__micad_btn_2" type="radio" name="stage" value="rodents" /><label for="__micad_btn_2">Rodents</label><input id="__micad_btn_3" type="radio" name="stage" value="mammals" /><label for="__micad_btn_3">Non-primate non-rodent mammals</label><br /><input id="__micad_btn_4" type="radio" name="stage" value="primates" /><label for="__micad_btn_4">Non-human primates</label><input id="__micad_btn_5" type="radio" name="stage" value="humans" /><label for="__micad_btn_5">Humans</label><input id="__micad_btn_6" type="radio" name="stage" value="any" checked="checked" /><label for="__micad_btn_6">Any</label></div></form><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmGo" method="get" action="javascript:alert('frmGo:_@action_was_not_set')" id="frmGo"><input name="term" value="." type="hidden" /></form></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Related information</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="discovery_db_links" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pmc&DbFrom=books&Cmd=Link&LinkName=books_pmc_refs&IdsFromResult=1505388" ref="log$=recordlinks">PMC</a><div class="brieflinkpop offscreen_noflow">PubMed Central citations</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pcsubstance&DbFrom=books&Cmd=Link&LinkName=books_pcsubstance&IdsFromResult=1505388" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=1505388" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641805" ref="ordinalpos=1&linkpos=1&log$=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> Self-quenched-regioselectively addressable functionalized template-[cyclo-(RGD-d-Phe-Lys)](4) peptide-Cy5-fluorescence quencher QSY21.</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> Self-quenched-regioselectively addressable functionalized template-[cyclo-(RGD-d-Phe-Lys)](4) peptide-Cy5-fluorescence quencher QSY21.<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, Razkin J, 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/20641381" ref="ordinalpos=1&linkpos=2&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Cy7-Tetrameric arginine-glycine-aspartic acid peptide.</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Cy7-Tetrameric arginine-glycine-aspartic acid peptide.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Cheng KT. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/22171395" ref="ordinalpos=1&linkpos=3&log$=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> (64)Cu-1,4,8,11-Tetraazacyclotetradecane-regioselectively addressable functionalized template-[cyclo-(Arg-Gly-Asp-d-Phe-Lys)](4).</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> (64)Cu-1,4,8,11-Tetraazacyclotetradecane-regioselectively addressable functionalized template-[cyclo-(Arg-Gly-Asp-d-Phe-Lys)](4).<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Leung K. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641939" ref="ordinalpos=1&linkpos=4&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Regioselectively addressable functionalized template-[cyclo-(Arg-Gly-Asp-d-Phe-Lys)](4).</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Regioselectively addressable functionalized template-[cyclo-(Arg-Gly-Asp-d-Phe-Lys)](4).<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Leung K. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20641361" ref="ordinalpos=1&linkpos=5&log$=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> 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" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li></ul><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed_reviews&uid=20641556" ref="ordinalpos=1&log$=relatedreviews_seeall&logdbfrom=pubmed">See reviews...</a><a 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