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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="#__NBK23235_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23235_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/NAPamide18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Choline-D4-18F/" 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="_NBK23235_"><span class="title" itemprop="name">[<sup>18</sup>F]FB-NH-mini-PEG-E{E[c(RGDyK)]<sub>2</sub>}<sub>2</sub></span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>18</sup>F]FPRGD4</div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23235_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23235_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kenneth T. Cheng</span>, PhD<div class="affiliation small">
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National Center for Biotechnology Information, NLM, NIH, Bethesda, MD,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a>
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</div></div></div><p class="small">Created: <span itemprop="datePublished">February 20, 2008</span>; Last Update: <span itemprop="dateModified">March 12, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="F18FPRGD4.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23235/table/F18FPRGD4.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__F18FPRGD4.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>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]FB-NH-mini-PEG-E{E(c(RGDyK)]<sub>2</sub>}<sub>2</sub></td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/49649810" 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=49649810" alt="image 49649810 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;">
|
||
<b>Abbreviated name:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]FPRGD4</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Synonym:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>18</sup>F-PEG-RGD, <sup>18</sup>F-labeled PEGylated tetrameric RGD peptide</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;">Peptide</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;">Positron Emission Tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Source of signal /contrast:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>18</sup>F</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 <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="F18FPRGD4.Background"><h2 id="_F18FPRGD4_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=18F-FPRGD4+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>[<sup>18</sup>F]FB-NH-mini-PEG-E{E[c(RGDyK)]<sub>2</sub>}<sub>2</sub> ([<sup>18</sup>F]FPRGD4) is an integrin-targeted molecular imaging agent developed for positron emission tomography (PET) of tumor vasculature and angiogenesis (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). <sup>18</sup>F is a positron emitter with a physical half-life (<i>t</i><sub>½</sub>) of 110 min.</p><p>Cellular survival, invasion, and migration control embryonic development, angiogenesis, tumor metastasis, and other physiologic processes (<a class="bk_pop" href="#F18FPRGD4.REF.2">2</a>, <a class="bk_pop" href="#F18FPRGD4.REF.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="#F18FPRGD4.REF.4">4</a>, <a class="bk_pop" href="#F18FPRGD4.REF.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.</p><p>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="#F18FPRGD4.REF.6">6</a>, <a class="bk_pop" href="#F18FPRGD4.REF.7">7</a>). Various RGD peptides in both linear and cyclic forms (RGDfK or RGDyK) have been developed for <i>in vivo</i> binding to integrin α<sub>v</sub>β<sub>3</sub> (<a class="bk_pop" href="#F18FPRGD4.REF.8">8</a>). To improve the pharmacokinetics and tumor retention of the radiolabeled peptide, a dimer analog was synthesized as <a href="/books/n/micad/FB-RGD2-18F/">[<sup>18</sup>F]FB-[c(RGDyK)]</a><sub>2</sub>, which showed improved tumor localization and predominant renal excretion (<a class="bk_pop" href="#F18FPRGD4.REF.9">9</a>). Alternatively, Chen et al. (<a class="bk_pop" href="#F18FPRGD4.REF.10">10</a>) modified c(RGDyK) with monofunctional methoxy-polyethylene glycol (mPEG; molecular weight = 2,000 kDa) and showed that the modified PEGylated RGD peptide had faster blood clearance, lower kidney uptake, and prolonged tumor uptake. Using the same strategy, Chen et al. (<a class="bk_pop" href="#F18FPRGD4.REF.11">11</a>) inserted a heterofunctional PEG (molecular weight = 3,400 kDa) molecule between the [<sup>18</sup>F]fluorobenzoyl component and the RGD peptide to produce [<sup>18</sup>F]FB-PEG-c(RGDyK) for imaging of brain tumor angiogenesis. The PEGylated [<sup>18</sup>F]FB-c(RGDyK) analog appeared to improve tumor retention and <i>in vivo</i> kinetics compared with [<sup>18</sup>F]FB-c(RGDyK). These improvements might be attributed to a number of possible causes that include shielding of antigenic and immunogenic epitopes, shielding receptor-mediated uptake by the reticuloendothelial systems, preventing the recognition and degradation by proteolytic enzymes, and increasing the apparent size of the peptide. Wu et al. (<a class="bk_pop" href="#F18FPRGD4.REF.12">12</a>) reported that a multimeric RGD peptide with more than two repeating cyclic RGD units would further enhance the affinity of the receptor−ligand interactions through the phenomenon of a polyvalency effect. However, the attempt of synthesis of 18F-labeled tetrameric RGDyK peptiode (<sup>18</sup>F-FRGD4) proved to be difficult and gave very low yield (<2%) because of increased molecular size and steric hindrance (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). On the basis of these observations, Wu et al. (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>) inserted a mini-PEG linker to improve the labeling yield and successfully prepared [<sup>18</sup>F]FPRGD4 by radiolabeling PEGylated tetrameric RGD peptide with reasonable yield. The <i>in vivo</i> kinetics of this PEGylated probe was studied in three different tumor models.</p></div><div id="F18FPRGD4.Synthesis"><h2 id="_F18FPRGD4_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(18F-FPRGD4)+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Wu et al. (<a class="bk_pop" href="#F18FPRGD4.REF.12">12</a>) reported the preparation of cyclic RGD peptide tetramer E{E[c(RGDyK)]<sub>2</sub>}<sub>2</sub> (RGD4) from the cyclic RGD dimer E[c(RGDyK)]<sub>2</sub>. RGD4 was then used to prepare NH<sub>2</sub>-Mini-PEG-E{E[c(RGDyK)]<sub>2</sub>}<sub>2</sub> (PRGD4) (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). Briefly, Boc-11-amino-3,6,9-trioxaundecanoic acid (Boc-NH-mini-PEG-OOH) was mixed with <i>N</i>,<i>N</i>-diisopropylethylamine and <i>O</i>-(<i>N</i>-succinimidyl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). The reaction mixture was stirred at room temperature for 0.5 h. RGD4 in <i>N</i>,<i>N</i>-dimethylformamide was added to the mixture and stirred at room temperature for 2 h to produce Boc-NH-mini-PEG-E{E[c(RGDyK)]<sub>2</sub>}<sub>2</sub>. The yield was 60%. The Boc-group was then removed by treatment with trifluoroacetic acid (TFA) for 5 min at room temperature to yield PRGD4. PRGD4 was purified by high-performance liquid chromatography (HPLC) for radiolabeling. The identify of PRGD4 was confirmed by matrix-assisted laser desorption/ionization mass spectrometry with m/z 3,001.0 for [MH]<sup>+</sup> (the calculated molecular weight of C<sub>131</sub>H<sub>194</sub>N<sub>40</sub>O<sub>42</sub> = 3,001.1).</p><p>The purified product of PRGD4 was labeled with <sup>18</sup>F by coupling with <i>N</i>-succinimidyl 4-[<sup>18</sup>F]fluorobenzoate ([<sup>18</sup>F]SFB) (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>, <a class="bk_pop" href="#F18FPRGD4.REF.13">13</a>). The synthesis was conducted with a commercial synthesis module. The total synthesis time was ~100 min and the decay-corrected yield was 67 ± 11% (<i>n</i> = 10). The purified [<sup>18</sup>F]SFB was added to PRGD4 in dimethyl sulfoxide with DIPEA. This peptide mixture was incubated at 60ºC for 30 min. The final product was then diluted with 1% TFA in water before purified by semipreparative HPLC to yield [<sup>18</sup>F]FPRGD4. The decay-corrected radiochemical yield based on [<sup>18</sup>F]SFB was 22.0 ± 0.8% (<i>n</i> = 4). Analytical HPLC showed that the radiochemical purity was >99%. The specific activity was ~100–200 GBq/μmol (2.7-5.4 Ci/μmol) based on [<sup>18</sup>F]SFB. Starting from <sup>18</sup>F-F<sup>–</sup>, the total synthesis time of [<sup>18</sup>F]FPRGD4 was ~180 min (including HPLC purification), and the overall decay-corrected yield was 15 ± 4%.</p></div><div id="F18FPRGD4.In_Vitro_Studies_Tes"><h2 id="_F18FPRGD4_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=((18F-FPRGD4)+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide))+AND+in+vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The octanol-water partition coefficient (log <i>P</i>) of [<sup>18</sup>F]FPRGD4 was determined to be –2.67 ± 0.22 with the use of phosphate-buffered saline and octanol (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). Wu et al. (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>) conducted an <i>in vitro</i> cell (U87MG human glioblastoma) integrin receptor-binding assays with [<sup>18</sup>F]FPRGD4 by using <sup>125</sup>I-echistatin (integrin α<sub>v</sub>β<sub>3</sub> specific) in displacement studies. The 50% inhibitory concentration IC<sub>50</sub> for [<sup>18</sup>F]FPRGD4 was 37.7 ± 7.0 nM (<i>n</i> = 3). In comparison, the IC<sub>50</sub> values for RGD4 and PRGD4 were 39.1 ± 5.5 and 46.5 ± 5.3, respectively.</p></div><div id="F18FPRGD4.Animal_Studies"><h2 id="_F18FPRGD4_Animal_Studies_">Animal Studies</h2><div id="F18FPRGD4.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((18F-FPRGD4)+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide))+AND+rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>MicroPET imaging of 3.7 MBq (100 μCi) [<sup>18</sup>F]FPRGD4 in nude mice (<i>n</i> = 3) bearing the s.c. U87MG tumor (100-300 mm<sup>3</sup>) as early as 5 min clearly visualized the tumor with a high contrast to contralateral background (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). The radiolabeled peptide was cleared mainly through the kidneys with some hepatic clearance. Using the region-of-interest (ROI) technique, the tumor radioactivity levels (% ID/g) were calculated to be 9.87 ± 0.10 (5 min), 7.80 ± 0.14 (30 min), 6.40 ± 0.27 (60 min), 5.39 ± 0.14 (120 min), and 4.82 ± 0.22 (180 min). When a blocking dose of 10 mg/kg c(RGDyK) was given, more than 80% of the tumor radioactivity was inhibited. Other major organ radioactivity levels were also reduced.</p><p>MicroPET imaging of 3.7 MBq (100 μCi) [<sup>18</sup>F]FPRGD4 was conducted in nude mice (<i>n</i> = 3) bearing the MDA-MB-435 tumor (orthotopic injection into the left mammary fat pad) which had lower integrin expression level than the U87MG tumor (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). The ROI tumor radioactivity levels (% ID/g) were lower that those of U87MG model with 5.07 ± 0.18 (30 min), 4.53 ± 0.36 (60 min), and 3.38 ± 0.48 (150 min). MicroPET imaging of 3.7 MBq (100 μCi) [<sup>18</sup>F]FPRGD4 was also performed in a spontaneous murine mammary carcinoma model grown in c-neu onomice (<i>n</i> = 3) (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). The ROI tumor radioactivity levels (% ID/g) were lower that those of U87MG model with 4.22 ± 0.18 (30 min), 3.56 ± 0.36 (60 min), and 2.36 ± 0.40 (150 min). Immunofluorescence staining of frozen tissue slices from c-neu oncomice confirmed the expression of β<sub>3</sub>-integrin in both tumor cells and endothelial cells of the murine mammary carcinoma (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>). β<sub>3</sub>-integrin was also detected in the liver, lung, kidneys, and glomerulus. No significant difference in organ distribution of [<sup>18</sup>F]FPRGD4 was observed among all three animal models. In a control study, microPET imaging of 3.7 MBq (100 μCi) [<sup>18</sup>F]FPRGD4 in nude mice (<i>n</i> = 3) bearing an integrin-negative s.c. DU145 tumor. The ROI tumor radioactivity levels (%ID/g) were significantly lower with 1.44 ± 0.34 (30 min) and 0.93 ± 0.13 (60 min) (<a class="bk_pop" href="#F18FPRGD4.REF.1">1</a>).</p></div><div id="F18FPRGD4.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((18F-FPRGD4)+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide))+AND+(dog+OR+rabbit+OR+pig+OR+sheep)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="F18FPRGD4.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((18F-FPRGD4)+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide))+AND+(primate+NOT+human)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="F18FPRGD4.Human_Studies"><h2 id="_F18FPRGD4_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=((18F-FPRGD4)+OR+(18F-labeled+PEGylated+tetrameric+RGD+peptide))AND+human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="F18FPRGD4.NIH_Support"><h2 id="_F18FPRGD4_NIH_Support_">NIH Support</h2><p>NIH NIBIB R21 EB001785, NCI CA102123, P50 CA114747, U54 CA119367, R24 CA93862.</p></div><div id="F18FPRGD4.references"><h2 id="_F18FPRGD4_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="F18FPRGD4.REF.1">Wu Z. , Li Z.B. , Chen K. , Cai W. , He L. , Chin F.T. , Li F. , Chen X. microPET of tumor integrin alphavbeta3 expression using 18F-labeled PEGylated tetrameric RGD peptide (18F-FPRGD4). <span><span class="ref-journal">J Nucl Med. </span>2007;<span class="ref-vol">
|
||
<strong>48</strong>
|
||
</span>(9):1536–44.</span> [<a href="/pmc/articles/PMC4183663/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC4183663</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17704249" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17704249</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="F18FPRGD4.REF.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="F18FPRGD4.REF.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="F18FPRGD4.REF.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="F18FPRGD4.REF.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="F18FPRGD4.REF.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="F18FPRGD4.REF.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="F18FPRGD4.REF.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="F18FPRGD4.REF.9">Chen X. , Tohme M. , Park R. , Hou Y. , Bading J.R. , Conti P.S. Micro-PET imaging of alphavbeta3-integrin expression with 18F-labeled dimeric RGD peptide. <span><span class="ref-journal">Mol Imaging. </span>2004;<span class="ref-vol">
|
||
<strong>3</strong>
|
||
</span>(2):96–104.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15296674" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15296674</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="F18FPRGD4.REF.10">Chen X. , Park R. , Shahinian A.H. , Bading J.R. , Conti P.S. Pharmacokinetics and tumor retention of 125I-labeled RGD peptide are improved by PEGylation. <span><span class="ref-journal">Nucl Med Biol. </span>2004;<span class="ref-vol">
|
||
<strong>31</strong>
|
||
</span>(1):11–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14741566" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14741566</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="F18FPRGD4.REF.11">Chen X. , Park R. , Hou Y. , Khankaldyyan V. , Gonzales-Gomez I. , Tohme M. , Bading J.R. , Laug W.E. , Conti P.S. MicroPET imaging of brain tumor angiogenesis with 18F-labeled PEGylated RGD peptide. <span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2004;<span class="ref-vol">
|
||
<strong>31</strong>
|
||
</span>(8):1081–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15118844" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15118844</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="F18FPRGD4.REF.12">Wu Y. , Zhang X. , Xiong Z. , Cheng Z. , Fisher D.R. , Liu S. , Gambhir S.S. , Chen X. microPET imaging of glioma integrin {alpha}v{beta}3 expression using (64)Cu-labeled tetrameric RGD peptide. <span><span class="ref-journal">J Nucl Med. </span>2005;<span class="ref-vol">
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<strong>46</strong>
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</span>(10):1707–18.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16204722" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16204722</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="F18FPRGD4.REF.13">Chen X. , Park R. , Shahinian A.H. , Tohme M. , Khankaldyyan V. , Bozorgzadeh M.H. , Bading J.R. , Moats R. , Laug W.E. , Conti P.S. 18F-labeled RGD peptide: initial evaluation for imaging brain tumor angiogenesis. <span><span class="ref-journal">Nucl Med Biol. </span>2004;<span class="ref-vol">
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<strong>31</strong>
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</span>(2):179–89.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15013483" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15013483</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></div></div></div>
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<div class="post-content"><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div><div class="small"><span class="label">Bookshelf ID: NBK23235</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641437" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641437</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/NAPamide18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/Choline-D4-18F/" 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/NBK23235/?report=reader">PubReader</a></li><li><a href="/books/NBK23235/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23235" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23235" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT. [18F]FB-NH-mini-PEG-E{E[c(RGDyK)]2}2. 2008 Feb 20 [Updated 2008 Mar 12]. 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/NBK23235/pdf/Bookshelf_NBK23235.pdf">PDF version of this page</a> (147K)</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="#F18FPRGD4.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#F18FPRGD4.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#F18FPRGD4.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#F18FPRGD4.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#F18FPRGD4.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#F18FPRGD4.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#F18FPRGD4.references" ref="log$=inpage&link_id=inpage">References</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Search MICAD</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="source-application" id="Shutter"></a></div><div class="portlet_content"><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmSearch" method="get" action="/books/NBK5330/" id="frmSearch"><script type="text/javascript" src="/corehtml/pmc//js/bookshelf/micad.js">/**/</script><label class="offscreen_noflow" for="txtfield">Search term</label><input id="txtfield" type="text" name="f1_term" size="22" onKeyPress="KeyPress('micad',event,'/books/NBK5330/','')" /><button name="f1_search" type="submit">Go</button><button onclick="this.form.reset();" type="reset">Clear</button><p><b>Limit my Search:</b></p><div class="clearfix"><label for="detection">Method of detection:</label><div class="right"><select name="detection" id="detection" style="width:200px"><option value="" selected="selected">Any</option><option value="(MRI OR "Magnetic resonance imaging" OR MRS)">MRI</option><option value="Multimodal">Multimodal imaging</option><option value="Optical">Optical imaging</option><option value="PET">PET</option><option value="Photoacoustic">Photoacoustic imaging</option><option value="(SPECT OR planar)">SPECT</option><option value="Ultrasound">Ultrasound</option><option value="(x-ray OR ct)">X-ray, CT</option></select></div></div><div class="clearfix"><label for="signal">Source of signal/contrast:</label><div class="right"><select name="signal" id="signal" style="width:200px"><option value="" selected="selected">Any</option><optgroup label="MRI agents"><option value="(Copper OR Cu)">Copper</option><option value="(Europium OR Eu3+)">Europium</option><option value="(Fluorine OR 19F)">Fluorine</option><option value="(Gadolinium OR Gd3+)">Gadolinium</option><option value=""Hyperpolarized 13C"">Hyperpolarized 13C</option><option value=""Iron oxide"">Iron oxide</option><option value=""Nitroxide radicals"">Nitroxide radicals</option><option value="(Oxygen OR 17O)">Oxygen</option><option value="Thulium">Thulium</option></optgroup><optgroup label="Multimodal agents"><option value="((Gadolinium OR Gd3+) AND Optical)">Gadolinium and optical</option><option value="((Gadolinium OR Gd3+) AND (Gold OR Au))">Gadolinium and Gold</option><option value="("Iron oxide" AND (64Cu OR 124I OR 111In))">Iron oxide and
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europium</option><option value="(166Ho OR 67Ga OR 68Ga OR 123I OR 124I OR 125I)">Radionuclides</option></optgroup><optgroup label="Optical agents"><option value="("Fluorescent dyes" OR protein)">Fluorescent dyes or proteins</option><option value=""Luminescent agents"">Luminescent agents</option><option value="(Metals OR Metal OR Gold OR Au)">Metals (Au)</option><option value="Nanotubes">Nanotubes</option><option value=""Quantum dots"">Quantum dots</option></optgroup><optgroup label="PET radionuclides"><option value="("Arsenic 74" OR 74As)">Arsenic-74</option><option value="("Bromine 76" OR 76Br)">Bromine-76</option><option value="("Carbon 11" OR 11C)">Carbon-11</option><option value="(Copper-60 OR Copper-61 OR Copper-62 OR Copper-64 OR 60Cu OR 61Cu OR 62Cu OR 64Cu)">Copper-60, 61, 62, 64</option><option value="("Fluorine 18" OR 18F)">Fluorine-18</option><option value="(Gallium-68 OR 68Ga)">Gallium-68</option><option value="("Iodine 124" OR 124I)">Iodine-124</option><option 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value="Nanobubbles">Nanobubbles</option></optgroup><optgroup label="X-ray and CT agents"><option value="(Bismuth OR Bi)">Bismuth</option><option value="(Gold OR Au)">Gold</option><option value="Iodine">Iodine</option></optgroup></select></div></div><div class="clearfix"><label for="agent">Agent Category:</label><div class="right"><select name="agent" id="agent" style="width:200px"><option value="" selected="selected">Any</option><option value="(antibody OR trastuzumab OR immunoglobulin)">Antibodies</option><option value="(bacteria OR bacteriophage OR coli)">Bacteria</option><option value="cell">Cells</option><option value="(compound OR "amino acid" OR "folic acid" OR "cage molecule" OR carbohydrate OR copolymers OR polymer OR "small molecule" OR macromolecule OR triiodobenzoate OR estradiol OR glycosaminoglycan)">Compounds</option><option value="ligand">Ligands</option><option value="(lipid OR liposome OR liposomes">Lipids</option><option value="metal">Metal</option><option value="(nanoparticle OR nanoparticles OR nanotubes OR "iron oxide")">Nanoparticles</option><option value="(siRNA OR "nucleic acid" OR oligonucleotide)">Nucleic acids</option><option value="peptide">Peptides</option><option value="polyeptide">Polyeptides</option><option value="(protein OR albumin OR chemokin OR immunoprotein OR luciferase OR albumin)">Proteins</option><option value="(virus OR adenovirus)">Viruses</option></select></div></div><div class="clearfix"><label for="target">Target Category:</label><div class="right"><select name="target" id="target" style="width:200px"><option value="" selected="selected">Any</option><option value="acceptor">Acceptors</option><option value=""adhesion molecule"">Adhesion molecules</option><option value="(antigen OR antibody-antigen)">Antigens</option><option value="(enzyme OR enzymes OR enzyme-substrate)">Enzymes</option><option value="(lipids OR lipophilic cation)">Lipids</option><option value="(receptor OR receptors OR receptor-ligand OR 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=1506384" 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=1506384" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=1506384" ref="log$=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/20641317" ref="ordinalpos=1&linkpos=1&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> [(18)F]Fluorobenzoyl-PEGylated cyclic arginine-glycine-aspartic acid peptide.</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> [(18)F]Fluorobenzoyl-PEGylated cyclic arginine-glycine-aspartic acid peptide.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Cheng KT, Conti PS. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" 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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (64)Cu-1,4,7,10-Tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid-E(E{E[c(RGDyK)](2)}(2))(2) peptide.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Cheng KT. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li></ul><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed_reviews&uid=20641437" ref="ordinalpos=1&log$=relatedreviews_seeall&logdbfrom=pubmed">See reviews...</a><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed&uid=20641437" ref="ordinalpos=1&log$=relatedarticles_seeall&logdbfrom=pubmed">See all...</a></div></div><div 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