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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="#__NBK23255_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23255_dtls__"><div>Bethesda (MD): <a href="https://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&amp;targetsite=external&amp;targetcat=link&amp;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/RM2-68Ga/" title="Previous page in this title">&lt; Prev</a><a class="active page_link next" href="/books/n/micad/DOTA-Bz-2-NI-68Ga/" title="Next page in this title">Next &gt;</a></div></div></div></div></div>
<div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><h1 id="_NBK23255_"><span class="title" itemprop="name"><sup>68</sup>Ga-Glutamate peptide-3 aminoethyl estradiol</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"><sup>68</sup>Ga-GAP-EDL</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23255_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23255_ai__"><div class="contrib half_rhythm"><span itemprop="author">Arvind Chopra</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH, Bethesda, MD 20894<div><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></div></div></div></div><p class="small">Created: <span itemprop="datePublished">August 23, 2007</span>; Last Update: <span itemprop="dateModified">June 18, 2009</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="GAPEDLGa68.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23255/table/GAPEDLGa68.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__GAPEDLGa68.T1_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
<b>Chemical name:</b>
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>68</sup>Ga-Glutamate peptide-3 aminoethyl estradiol</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
<span class="graphic"><img src="/books/NBK23255/bin/GAPEDL.jpg" alt="Image GAPEDL.jpg" /></span>
</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>68</sup>Ga-GAP-EDL</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;"></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
<b>Backbone:</b>
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Estradiol</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;">Estrogen receptor</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
<b>Mechanism:</b>
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Receptor-ligand 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:</b>
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>68</sup>Ga</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;">Not required</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><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;">Structure of GAP-EDL. The exact location of <sup>68</sup>Ga in the structure is unknown.</td></tr></tbody></table></div></div><div id="GAPEDLGa68.Background"><h2 id="_GAPEDLGa68_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=GAP-EDL" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>Approximately 10% of women of reproductive age are affected by endometriosis, a gynecological disorder (<a class="bk_pop" href="#GAPEDLGa68.REF.1">1</a>). Painful periods, pelvic pain, and infertility are often associated with endometriosis. Although a variety of mechanisms, including the roles of different cytokines, growth factors, and hormones, have been proposed in the development of endometriosis, the exact etiology and epidemiology of this condition is unclear (<a class="bk_pop" href="#GAPEDLGa68.REF.1" data-bk-pop-others="GAPEDLGa68.REF.2 GAPEDLGa68.REF.3">1-3</a>). Menstruation in the opposite direction with spillage of viable endometrial cells into the peritoneum is often observed in cycling women (<a class="bk_pop" href="#GAPEDLGa68.REF.4">4</a>). Adhesion, proliferation, and spread of the shed endometrial cells to the peritoneum are believed to support the development of endometriosis (<a class="bk_pop" href="#GAPEDLGa68.REF.5" data-bk-pop-others="GAPEDLGa68.REF.6 GAPEDLGa68.REF.7">5-7</a>). Endometriosis is usually detected by a surgical technique such as a laparoscopy. Performing such a procedure on patients with infertility is often complex, and it provides information only about the morphological and anatomical changes in the tissue (<a class="bk_pop" href="#GAPEDLGa68.REF.8">8</a>). Moreover, endometriosis usually progresses or recurs after surgery, and any relief to the patient is temporary (<a class="bk_pop" href="#GAPEDLGa68.REF.9">9</a>).</p><p>Because the prevalence and progression of endometriosis cannot be studied in humans without a laparoscopy, non-primate and primate animal models, including rabbits, have been used to investigate this disease (<a class="bk_pop" href="#GAPEDLGa68.REF.10" data-bk-pop-others="GAPEDLGa68.REF.11 GAPEDLGa68.REF.12">10-12</a>). It has also been shown that estrogen receptors (ER) are overexpressed in the uterine endometrium and endometriotic lesions in endometriosis (<a class="bk_pop" href="#GAPEDLGa68.REF.4">4</a>). In an effort to develop a non-invasive method to detect endometriosis, Takahashi et al. explored the use of estrogen, an ER ligand, to image endometriosis induced in rabbits (<a class="bk_pop" href="#GAPEDLGa68.REF.8">8</a>). For this, estradiol (EDL) was conjugated to a glutamate peptide (GAP), which contained 5&#x02013;10 glutamic acid residues, to facilitate the chelation of radioactive gallium (<sup>68</sup>Ga) to obtain <sup>68</sup>Ga-GAP-EDL to image endometriosis.</p></div><div id="GAPEDLGa68.Synthesis"><h2 id="_GAPEDLGa68_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=Ga+GAP+EDL" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>The synthesis of <sup>68</sup>Ga-GAP-EDL was performed as described by Takahashi et al. (<a class="bk_pop" href="#GAPEDLGa68.REF.8" data-bk-pop-others="GAPEDLGa68.REF.13">8, 13</a>). To start, estrone was dissolved in anhydrous ethanol. Sodium ethoxide and bromoacetonitrile were added to the solution and the mixture was heated under reflux for 3 h. The ethanol was allowed to evaporate completely and the residue was dissolved in ethyl acetate. The solution was washed with water and the organic layer was filtered after drying over magnesium sulphate. The ethyl actetate was evaporated under reduced pressure and the remaining solid product, 3-acetonitrile estradiol, was washed with ether. The yield of this reaction was 75%. The solid product was dissolved in tetrahydrofuran, and lithium aluminum hydride was added to the mixture and stirred for 4 h. The solvent was evaporated to yield a solid that was dissolved in ethyl acetate. This solution was washed with water, dried over magnesium sulphate, and filtered. The solvent was evaporated to obtain 3-cyanomethyl estrone (EDL) with a yield of 92%. The structure of EDL was confirmed by nuclear magnetic resonance.</p><p>For the synthesis of GAP-EDL, the sodium salt of GAP was converted to the acid form by the addition of 2 N hydrochloric acid (HCl). This solution was dialyzed to remove all the acid and freeze-dried to obtain the acidic form of GAP. The GAP acid was dissolved in dimethylformamide (DMF), and dicyclohexyl carbodiimide and 4-<i>N,N</i>-dimethyl aminopyridine were added to it. This mixture was stirred at room temperature for 2 days. The DMF was evaporated under reduced pressure; 1 N sodium bicarbonate was added to it and extracted with chloroform. The aqueous solution was dialyzed, filtered, and freeze-dried to obtain GAP-EDL. The percent yield of this reaction was not provided in the publication. The GAP-EDL complex contained 7% (weight/weight) EDL as determined by ultraviolet spectroscopy.</p><p>For the synthesis of <sup>68</sup>Ga-GAP-EDL, <sup>68</sup>Ga was eluted from a <sup>68</sup>Ge/<sup>68</sup>Ga generator with 0.1 N HCl, and the acidic solution was passed through an anion resin cartridge to trap the <sup>68</sup>Ga. The cartridge was washed with 4 N HCl and air-dried. The <sup>68</sup>Ga was eluted as <sup>68</sup>Ga-chloride (<sup>68</sup>GaCl<sub>3</sub>) from the cartridge with water, and the pH was adjusted to 4&#x02013;5 with sodium hydroxide and sodium acetate. GAP-EDL in acetate buffer was added to the <sup>68</sup>GaCl<sub>3</sub> solution, and the reaction was completed by warming at 37&#x000b0;C for 20 min. Radiochemical purity of the product was determined by instant thin-layer chromatography. The Rf values for GAP-EDL and <sup>68</sup>GaCl<sub>3</sub> were reported to be 0.1 and 0.9, respectively. The radiochemical purity of the radiotracer was &#x0003e;95%. Specific activity of the radiotracer was not provided in the publication (<a class="bk_pop" href="#GAPEDLGa68.REF.8">8</a>).</p></div><div id="GAPEDLGa68.In_Vitro_Studies_Tes"><h2 id="_GAPEDLGa68_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=Radiolabeled-GAP-EDL+in+vitro" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>The uptake of <sup>68</sup>Ga-GAP-EDL was studied in the 13762 rat adenocarcinoma cell line (<a class="bk_pop" href="#GAPEDLGa68.REF.8">8</a>), and accumulation of the radiopharmaceutical in these cells was shown to increase with time. Addition of cold estrone (estradiol) inhibited the uptake in a dose-dependent manner. This indicated that the uptake of <sup>68</sup>Ga-GAP-EDL in the cells was an ER-mediated process.</p></div><div id="GAPEDLGa68.Animal_Studies"><h2 id="_GAPEDLGa68_Animal_Studies_">Animal Studies</h2><div id="GAPEDLGa68.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=radiolabeled+gap-edl+rodentia" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div><div id="GAPEDLGa68.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=radiolabeled+gap-edl+non+primate+mammals" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>The uptake of <sup>68</sup>Ga-GAP-EDL was investigated in rabbits with induced endometriosis (<a class="bk_pop" href="#GAPEDLGa68.REF.8">8</a>). Endometrial tissues were implanted in the rabbits, and the implanted endometrial tissue was microscopically visible in the animals after 8 weeks. The uptake of <sup>68</sup>Ga-GAP-EDL by the rabbits was investigated with and without the treatment of tamoxifen, a competitive inhibitor of estrogen for binding to the ER. A cross-sectional review of the coronal and sagittal images taken by positron emission tomography showed that the endometrial implant tissue could be differentiated from the skeletal, hepatobiliary, and urinary uptake of the label. Prior treatment of the animals with tamoxifen resulted in the inhibition of label uptake by the endometrial tissue. This demonstrated that the uptake of <sup>68</sup>Ga-GAP-EDL in the endometrial implants was ER-mediated. From this observation, the investigators suggested that <sup>68</sup>Ga-GAP-EDL can be used as a non-invasive imaging agent for the detection and monitoring of endometriosis and other diseases associated with the overexpression of ER, such as breast cancer .</p></div><div id="GAPEDLGa68.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=radiolabeled+gap-edl+non+human+primates" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div></div><div id="GAPEDLGa68.Human_Studies"><h2 id="_GAPEDLGa68_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&#x00026;Cmd=DetailsSearch&#x00026;Term=Radiolabeled+GAP+EDL+humans" ref="pagearea=body&amp;targetsite=external&amp;targetcat=link&amp;targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div><div id="GAPEDLGa68.References"><h2 id="_GAPEDLGa68_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.1">Lebovic D.I., Mueller M.D., Taylor R.N.
<em>Immunobiology of endometriosis.</em>
<span><span class="ref-journal">Fertil Steril. </span>2001;<span class="ref-vol">75</span>(1):110.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11163805" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 11163805</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.2">Cramer, D.W. and S.A. Missmer<em>The epidemiology of endometriosis.</em> Ann N Y Acad Sci, 2002<strong>955</strong>: p. 11-22; discussion 34-6, 396-406. [<a href="https://pubmed.ncbi.nlm.nih.gov/11949940" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 11949940</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.3">Hever A., Roth R.B., Hevezi P., Marin M.E., Acosta J.A., Acosta H., Rojas J., Herrera R., Grigoriadis D., White E., Conlon P.J., Maki R.A., Zlotnik A.
<em>Human endometriosis is associated with plasma cells and overexpression of B lymphocyte stimulator.</em>
<span><span class="ref-journal">Proc Natl Acad Sci U S A. </span>2007;<span class="ref-vol">104</span>(30):124516.</span> [<a href="/pmc/articles/PMC1941489/" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pmc">PMC free article<span class="bk_prnt">: PMC1941489</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17640886" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 17640886</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.4">Leyendecker G., Herbertz M., Kunz G., Mall G.
<em>Endometriosis results from the dislocation of basal endometrium.</em>
<span><span class="ref-journal">Hum Reprod. </span>2002;<span class="ref-vol">17</span>(10):272536.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12351554" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 12351554</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.5">Halme J., Hammond M.G., Hulka J.F., Raj S.G., Talbert L.M.
<em>Retrograde menstruation in healthy women and in patients with endometriosis.</em>
<span><span class="ref-journal">Obstet Gynecol. </span>1984;<span class="ref-vol">64</span>(2):1514.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6234483" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 6234483</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.6">Kruitwagen R.F., Poels L.G., Willemsen W.N., de Ronde I.J., Jap P.H., Rolland R.
<em>Endometrial epithelial cells in peritoneal fluid during the early follicular phase.</em>
<span><span class="ref-journal">Fertil Steril. </span>1991;<span class="ref-vol">55</span>(2):297303.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/1991528" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 1991528</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.7">Evers J.L.
<em>The defense against endometriosis.</em>
<span><span class="ref-journal">Fertil Steril. </span>1996;<span class="ref-vol">66</span>(3):3513.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8751728" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 8751728</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.8">Takahashi N., Yang D.J., Kurihara H., Borne A., Kohanim S., Oh C.S., Mawlawi O., Kim E.E.
<em>Functional Imaging of Estrogen Receptors with Radiolabeled-GAP-EDL in Rabbit Endometriosis Model.</em>
<span><span class="ref-journal">Acad Radiol. </span>2007;<span class="ref-vol">14</span>(9):10507.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17707312" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 17707312</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.9">DeCherney A.H.
<em>Endometriosis: recurrence and retreatment.</em>
<span><span class="ref-journal">Clin Ther. </span>1992;<span class="ref-vol">14</span>(6):76672.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/1286484" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 1286484</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.10">D'Hooghe T.M., Bambra C.S., Raeymaekers B.M., De Jonge I., Lauweryns J.M., Koninckx P.R.
<em>Intrapelvic injection of menstrual endometrium causes endometriosis in baboons (Papio cynocephalus and Papio anubis).</em>
<span><span class="ref-journal">Am J Obstet Gynecol. </span>1995;<span class="ref-vol">173</span>(1):12534.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7631669" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 7631669</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.11">Schenken R.S., Asch R.H.
<em>Surgical induction of endometriosis in the rabbit: effects on fertility and concentrations of peritoneal fluid prostaglandins.</em>
<span><span class="ref-journal">Fertil Steril. </span>1980;<span class="ref-vol">34</span>(6):5817.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7450077" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 7450077</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.12">Steinleitner A., Lambert H., Suarez M., Serpa N., Roy S.
<em>Immunomodulation in the treatment of endometriosis-associated subfertility: use of pentoxifylline to reverse the inhibition of fertilization by surgically induced endometriosis in a rodent model.</em>
<span><span class="ref-journal">Fertil Steril. </span>1991;<span class="ref-vol">56</span>(5):9759.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/1936333" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 1936333</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="GAPEDLGa68.REF.13">Takahashi N., Yang D.J., Kohanim S., Oh C.S., Yu D.F., Azhdarinia A., Kurihara H., Zhang X., Chang J.Y., Kim E.E.
<em>Targeted functional imaging of estrogen receptors with 99mTc-GAP-EDL.</em>
<span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2007;<span class="ref-vol">34</span>(3):35462.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17021817" ref="pagearea=cite-ref&amp;targetsite=entrez&amp;targetcat=link&amp;targettype=pubmed">PubMed<span class="bk_prnt">: 17021817</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></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/NBK23255/?report=reader">PubReader</a></li><li><a href="/books/NBK23255/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23255" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23255" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. 68Ga-Glutamate peptide-3 aminoethyl estradiol. 2007 Aug 23 [Updated 2009 Jun 18]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></div></div></li><li><a href="/books/NBK23255/pdf/Bookshelf_NBK23255.pdf">PDF version of this page</a> (146K)</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="#GAPEDLGa68.Background" ref="log$=inpage&amp;link_id=inpage">Background</a></li><li><a href="#GAPEDLGa68.Synthesis" ref="log$=inpage&amp;link_id=inpage">Synthesis</a></li><li><a href="#GAPEDLGa68.In_Vitro_Studies_Tes" ref="log$=inpage&amp;link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#GAPEDLGa68.Animal_Studies" ref="log$=inpage&amp;link_id=inpage">Animal Studies</a></li><li><a href="#GAPEDLGa68.Human_Studies" ref="log$=inpage&amp;link_id=inpage">Human Studies</a></li><li><a href="#GAPEDLGa68.References" ref="log$=inpage&amp;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 &quot;Magnetic resonance imaging&quot; 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="&quot;Hyperpolarized 13C&quot;">Hyperpolarized 13C</option><option value="&quot;Iron oxide&quot;">Iron oxide</option><option value="&quot;Nitroxide radicals&quot;">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="(&quot;Iron oxide&quot; AND (64Cu OR 124I OR 111In))">Iron oxide and
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OR 124I)">Iodine-124</option><option value="(&quot;Nitrogen 13&quot; OR 13N)">Nitrogen-13</option><option value="(&quot;Yttrium 86&quot; OR 86Y)">Yttrium-86</option><option value="(&quot;Zirconium 89&quot; OR 89Zr)">Zirconium-89</option></optgroup><optgroup label="Photoacoustic agents"><option value="(Gold OR Au)">Gold</option><option value="(&quot;Indocyanine green&quot; OR ICG)">Indocyanine green</option></optgroup><optgroup label="SPECT radionuclides"><option value="(Gallium-67 OR 67Ga)">Gallium-67</option><option value="(&quot;Indium 111&quot; OR 111In)">Indium-111</option><option value="(&quot;Iodine 123&quot; OR &quot;Iodine 125&quot; OR &quot;Iodine 131&quot; OR 123I OR 125I OR 131I)">Iodine-123, 125, 131</option><option value="(&quot;Lutetium 177&quot; OR 177Lu)">Lutetium-177</option><option value="(Rhenium OR 186Re OR 188Re)">Rhenium</option><option value="(&quot;Technetium 99m&quot; OR 99mTc)">Technetium-99m</option><option value="(&quot;Tellurium 125m&quot; OR 125mTe)">Tellurium-125m</option></optgroup><optgroup label="Ultrasound agents"><option value="Microbubbles">Microbubbles</option><option 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 &quot;amino acid&quot; OR &quot;folic acid&quot; OR &quot;cage molecule&quot; OR carbohydrate OR copolymers OR polymer OR &quot;small molecule&quot; 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 &quot;iron oxide&quot;)">Nanoparticles</option><option value="(siRNA OR &quot;nucleic acid&quot; 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="&quot;adhesion molecule&quot;">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="&quot;nucleic acid&quot;">Nucleic acids</option><option value="(non-targeted OR &quot;unknown binding site&quot;)">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&amp;DbFrom=books&amp;Cmd=Link&amp;LinkName=books_pmc_refs&amp;IdsFromResult=1503010" ref="log$=recordlinks">PMC</a><div class="brieflinkpop offscreen_noflow">PubMed Central citations</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&amp;DbFrom=books&amp;Cmd=Link&amp;LinkName=books_pubmed_refs&amp;IdsFromResult=1503010" ref="log$=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/17707312" ref="ordinalpos=1&amp;linkpos=1&amp;log$=relatedarticles&amp;logdbfrom=pubmed">Functional imaging of estrogen receptors with radiolabeled-GAP-EDL in rabbit endometriosis model.</a><span class="source">[Acad Radiol. 2007]</span><div class="brieflinkpop offscreen_noflow">Functional imaging of estrogen receptors with radiolabeled-GAP-EDL in rabbit endometriosis model.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Takahashi N, Yang DJ, Kurihara H, Borne A, Kohanim S, Oh CS, Mawlawi O, Kim EE. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Acad Radiol. 2007 Sep; 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