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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="#__NBK23350_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23350_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/L-159884-11C/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MP4A11C/" 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="_NBK23350_"><span class="title" itemprop="name"><i>N</i>-[<sup>11</sup>C]Methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2’,2’-diphenylpropionoxymethyl)pyridinium</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>11</sup>C]MDDP</div><p class="contrib-group"><span itemprop="author">The MICAD Research Team</span>.</p><p class="small">Created: <span itemprop="datePublished">June 24, 2006</span>; Last Update: <span itemprop="dateModified">July 25, 2006</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="MDDP11C.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23350/table/MDDP11C.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__MDDP11C.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;"><i>N</i>-[<sup>11</sup>C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2',2'-diphenylpropionoxymethyl)pyridinium</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/24424554" 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=24424554" alt="image 24424554 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;">[<sup>11</sup>C]MDDP</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;"></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Compound</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Acetylcholinerase (AChE)</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;">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;">PET</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>11</sup>C</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 id="A774" 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><li id="A775" 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></tr></tbody></table></div></div><div id="MDDP11C.Background"><h2 id="_MDDP11C_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=11C%5BAll%20Fields%5D%20AND%20MDDP%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Acetylcholinerase (AChE) is an enzyme involved in terminating nerve impulses by hydrolyzing the neurotransmitter acetylcholine (ACh). It plays an important role in heart rate and cardiac contractions, for example, by decreasing the ACh levels associated with cardiac parasympathetic responses (<a class="bk_pop" href="#MDDP11C.EXTYLES.1">1</a>).</p><p>AChE, and more exactly the inhibition of its enzymatic function, also seems to play an important role in poisoning from organophosphorus (OP) agents (<a class="bk_pop" href="#MDDP11C.EXTYLES.2">2</a>). Current treatments consisting of a reversible covalent AChE inhibitor (pyridostigmine (<a class="bk_pop" href="#MDDP11C.EXTYLES.3">3</a>)), a receptor antagonist atropine (ATR), and a AChE reactivator (pralidoxime chloride) have shown good protection against OP intoxication in animals. Research efforts are being made to find drugs with multiple protective functions. For example, Leader et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.4">4</a>) synthesized and evaluated a group of pyridophen analogues, binary pyridogstigmine-aprophen prodrugs with differential inhibition of AChE, butyrylcholinesterase (BChE), and muscarinic receptors (<a class="bk_pop" href="#MDDP11C.EXTYLES.5">5</a>).</p><p>Most of the AChE heart tracers developed for cardiac neurotransmission using positron emission tomography (PET) have shown low selectivity of AChE over BChE, and non-specific binding in AChE enzyme overexpressed regions (<a class="bk_pop" href="#MDDP11C.EXTYLES.6">6</a>). [<sup>11</sup>C]Nedrophonium and [<sup>11</sup>C]Neostigmine, originally developed as potential PET heart imaging agents, have shown either high nonspecific binding or poor myocardial uptake and were therefore unsuitable for PET imaging of the heart vagal system.</p><p>[<sup>11</sup>C]pyridostigmine and its para- and ortho-analogs, as well as <i>N</i>-[<sup>11</sup>C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2',2'-diphenylpropionoxymethyl)pyridinium ([<sup>11</sup>C]MDDP), were synthesized by Wang et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.7">7</a>) as potential PET agents for imaging heart AChE <i>in vivo</i>. Leader et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.4">4</a>) showed that MDDP iodide selectively inhibited AChE more than BChE. However, the first rodent studies performed by Wang et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.7">7</a>) using PET- [<sup>11</sup>C]MDDP did show the presence of nonspecific binding (see the Rodents section for details).</p></div><div id="MDDP11C.Synthesis"><h2 id="_MDDP11C_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2811C%29MDDP%20AND%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]<a href="/entrez/query.fcgi?CMD=search&DB=pubmed" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"></a></p><p>A multi-step synthesis procedure for [<sup>11</sup>C]MDDP was reported by Wang et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.7">7</a>) in 2005. The authors used a modified version of a method by Leader et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.4">4</a>) to obtain the precursor and reference standard. Briefly, the preparation of [<sup>11</sup>C]MDDP involved an acylation of the key intermediate 2-hydroxymethyl-3-dimethylaminocarbonyl-oxypyridine with 2,2-diphenylpropionyl chloride to produce the carbamyl-ester precursor 3-[[(dimethylamino)carbonyl]oxy]-2-(2',2'-diphenylpropionoxymethyl)pyridine in 51% yield.</p><p>The key intermediate used in this synthetic method was obtained in 31% yield from carbamylation of 3-hydroxy-2-hydroxymethylpyridine HCl with dimethylcarbamyl chloride; the acylation agent was produced in 96% yield from 2,2-diphenylpropionic acid with thionyl chloride in 96% yield.</p><p>The tertiary pyridine precursor was labeled with [<sup>11</sup>C]methyl triflate to provide the quaternary pyridinium tracer [<sup>11</sup>C]MDDP in 40–65% radiochemical yield (decay corrected at end of bombardment). The final product [<sup>11</sup>C]MDDP was eluted with an aqueous solution of 2% acetic acid (containing up to 8% ethanol to enhance recovery of some [<sup>11</sup>C-methyl]quaternary cations. The total synthesis time reported by Wang et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.7">7</a>) was 10–15 min. The chemical and radiochemical purities (determined by analytical HPLC) were >95% and >99% respectively. The specific radioactivity of the tracer [<sup>11</sup>C]MDDP was ~0.05 MBq/mol (1.0–1.5 Ci/μmol) at end of the synthesis.</p></div><div id="MDDP11C.In_Vitro_Studies_Tes"><h2 id="_MDDP11C_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=%2811C%29MDDP%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><i>In vitro</i> studies performed by Leader et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.4">4</a>) showed that MDDP iodide preferentially inhibited AChE over BChE, and that the inhibition of both enzymes was at least as strong as that obtained with pyridogstigmine (<a class="bk_pop" href="#MDDP11C.EXTYLES.8">8</a>). The mean values of the affinity constant for the initial reaction obtained for AChE and BChE were 5.62 x 10<sup>-6</sup> M and 3.14 x 10<sup>-6</sup> M respectively. In comparison, for pyridostigmine, those values were 1.97 x 10<sup>-5</sup> M (AChE) and 1.14 x 10<sup>-4</sup> M (BChE).</p></div><div id="MDDP11C.Animal_Studies"><h2 id="_MDDP11C_Animal_Studies_">Animal Studies</h2><div id="MDDP11C.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2811C%29MDDP%20AND%20rodentia%5BMeSH%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Wang et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.7">7</a>) performed <i>in vivo</i> dynamic PET imaging studies using [<sup>11</sup>C]MDDP in 3 young adult female Sprague–Dawley rats for a 60min time period after intravenous injection of 7.4 MBq (0.2 mCi) of the tracer for each animal. Those studies showed a rapid heart uptake of the tracer, and a fast blood clearance in 10 to 20 min. The mean standard uptake value (SUV) for [<sup>11</sup>C]MDDP reported by the authors was 0.125 ± 0.034 (<i>n</i> = 3).</p><p>Competitive inhibition studies were then performed to assess the specificity of the tracer to heart tissue AChE. Animals were pretreated with an injection of the drug neostigmine, used as unlabeled AChE inhibitor. A partial blocking effect was observed. However, a <i>t</i> test comparing the mean SUVs with no blocking agent (0.125 ± 0.034) and with blocker neostigmine (0.128 ± 0.0066) led to a <i>p</i> value of 0.87, indicating no statistically significant difference between the two and therefore the presence of nonspecific binding. Wang et al. (<a class="bk_pop" href="#MDDP11C.EXTYLES.7">7</a>) also suggested the possibility of an insufficient blockade of cholinesterase binding sites, because 2 of 3 rats exhibited actual increases in [<sup>11</sup>C]MDDP retention after administration of neostigmine.</p></div><div id="MDDP11C.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2811C%29MDDP%20AND%20%28dog%20OR%20pig%20OR%20rabbit%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="MDDP11C.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2811C%29MDDP%20AND%20%28primates%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="MDDP11C.Human_Studies"><h2 id="_MDDP11C_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2811C%29MDDP%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available</p></div><div id="MDDP11C.references"><h2 id="_MDDP11C_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.1">Gomez JL , Moral-Naranjo MT , Campoy FJ , Vidal CJ . Characterization of acetylcholinesterase and butyrylcholinesterase forms in normal and dystrophic Lama2dy mouse heart. <span><span class="ref-journal">J Neurosci Res. </span>1999;<span class="ref-vol">56</span>(3):295–306.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10336259" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10336259</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.2">Duysen EG , Li B , Xie W , Schopfer LM , Anderson RS , Broomfield CA , Lockridge O . Evidence for nonacetylcholinesterase targets of organophosphorus nerve agent: supersensitivity of acetylcholinesterase knockout mouse to VX lethality. <span><span class="ref-journal">J Pharmacol Exp Ther. </span>2001;<span class="ref-vol">299</span>(2):528–535.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11602663" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11602663</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.3">Dirnhuber P , French MC , Green DM , Leadbeater L , Stratton JA . The protection of primates against soman poisoning by pretreatment with pyridostigmine. <span><span class="ref-journal">J Pharm Pharmacol. </span>1979;<span class="ref-vol">31</span>(5):295–299.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/37298" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 37298</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.4">Leader H , Wolfe AD , Chiang PK , Gordon RK . Pyridophens: binary pyridostigmine-aprophen prodrugs with differential inhibition of acetylcholinesterase, butyrylcholinesterase, and muscarinic receptors. <span><span class="ref-journal">J Med Chem. </span>2002;<span class="ref-vol">45</span>(4):902–910.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11831902" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11831902</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.5">Leader H , Smejkal RM , Payne CS , Padilla FN , Doctor BP , Gordon RK , Chiang PK . Binary antidotes for organophosphate poisoning: aprophen analogues that are both antimuscarinics and carbamates. <span><span class="ref-journal">J Med Chem. </span>1989;<span class="ref-vol">32</span>(7):1522–1528.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2738887" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2738887</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.6">Ryu EK , Choe YS , Park EY , Paik JY , Kim YR , Lee KH , Choi Y , Kim SE , Kim BT . Synthesis and evaluation of 2-[18F]fluoro-CP-118,954 for the in vivo mapping of acetylcholinesterase. <span><span class="ref-journal">Nucl Med Biol. </span>2005;<span class="ref-vol">32</span>(2):185–191.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15721764" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15721764</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.7">Wang JQ , Miller MA , Mock BH , Lopshire JC , Groh WJ , Zipes DP , Hutchins GD , Zheng QH . Facile synthesis and PET imaging of a novel potential heart acetylcholinesterase tracer N-[11C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2',2'-diphenylpropionoxy methyl)pyridinium. <span><span class="ref-journal">Bioorg Med Chem Lett. </span>2005;<span class="ref-vol">15</span>(20):4510–4514.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16112863" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16112863</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="MDDP11C.EXTYLES.8">Main AR , Hastings FL . Carbamylation and binding constants for the inhibition of acetylcholinesterase by physostigmine (eserine). <span><span class="ref-journal">Science. </span>1966;<span class="ref-vol">154</span>(747):400–402.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/5917090" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 5917090</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/NBK23350/?report=reader">PubReader</a></li><li><a href="/books/NBK23350/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23350" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23350" style="display:none" title="Cite this Page"><div class="bk_tt">The MICAD Research Team. N-[11C]Methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2’,2’-diphenylpropionoxymethyl)pyridinium. 2006 Jun 24 [Updated 2006 Jul 25]. 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/NBK23350/pdf/Bookshelf_NBK23350.pdf">PDF version of this page</a> (130K)</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="#MDDP11C.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#MDDP11C.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#MDDP11C.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#MDDP11C.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#MDDP11C.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#MDDP11C.references" ref="log$=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 value="("Nitrogen 13" OR 13N)">Nitrogen-13</option><option value="("Yttrium 86" OR 86Y)">Yttrium-86</option><option value="("Zirconium 89" OR 89Zr)">Zirconium-89</option></optgroup><optgroup label="Photoacoustic agents"><option value="(Gold OR Au)">Gold</option><option value="("Indocyanine green" OR ICG)">Indocyanine green</option></optgroup><optgroup label="SPECT radionuclides"><option value="(Gallium-67 OR 67Ga)">Gallium-67</option><option value="("Indium 111" OR 111In)">Indium-111</option><option value="("Iodine 123" OR "Iodine 125" OR "Iodine 131" OR 123I OR 125I OR 131I)">Iodine-123, 125, 131</option><option value="("Lutetium 177" OR 177Lu)">Lutetium-177</option><option value="(Rhenium OR 186Re OR 188Re)">Rhenium</option><option value="("Technetium 99m" OR 99mTc)">Technetium-99m</option><option value="("Tellurium 125m" 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 "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 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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=pcsubstance&DbFrom=books&Cmd=Link&LinkName=books_pcsubstance&IdsFromResult=1507716" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" 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and PET imaging of a novel potential heart acetylcholinesterase tracer N-[11C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2',2'-diphenylpropionoxymethyl)pyridinium.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Wang JQ, Miller MA, Mock BH, Lopshire JC, Groh WJ, Zipes DP, Hutchins GD, Zheng QH. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Bioorg Med Chem Lett. 2005 Oct 15; 15(20):4510-4. </em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/11831902" ref="ordinalpos=1&linkpos=2&log$=relatedarticles&logdbfrom=pubmed">Pyridophens: binary pyridostigmine-aprophen prodrugs with differential inhibition of acetylcholinesterase, butyrylcholinesterase, and muscarinic receptors.</a><span class="source">[J Med Chem. 2002]</span><div class="brieflinkpop 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