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<title>Quinolinium, 1,1'-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-methyl-2(3H)-benzothiazolylidene)-1-propen-1-yl]-,iodide (1:4) - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<div class="pre-content"><div><div class="bk_prnt"><p class="small">NCBI Bookshelf. A service of the National Library of Medicine, National Institutes of Health.</p><p>Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. </p></div><div class="iconblock clearfix whole_rhythm no_top_margin bk_noprnt"><a class="img_link icnblk_img" title="Table of Contents Page" href="/books/n/micad/"><img class="source-thumb" src="/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" alt="Cover of Molecular Imaging and Contrast Agent Database (MICAD)" height="100px" width="80px" /></a><div class="icnblk_cntnt eight_col"><h2>Molecular Imaging and Contrast Agent Database (MICAD) [Internet].</h2><a data-jig="ncbitoggler" href="#__NBK92611_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK92611_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/sostoto3/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/sosVT750/" 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="_NBK92611_"><span class="title" itemprop="name">Quinolinium, 1,1'-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-methyl-2(3<i>H</i>)-benzothiazolylidene)-1-propen-1-yl]-,iodide (1:4)</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">TOTO-3</div><p class="contrib-group"><span itemprop="author">Liang Shan</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK92611_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK92611_ai__"><div class="contrib half_rhythm"><span itemprop="author">Liang Shan</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH<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 class="small">Corresponding author.</div></div></div><p class="small">Created: <span itemprop="datePublished">April 2, 2012</span>; Last Update: <span itemprop="dateModified">May 2, 2012</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="TOTO-3.T.nc_chemical_namequinolinium_111" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK92611/table/TOTO-3.T.nc_chemical_namequinolinium_111/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__TOTO-3.T.nc_chemical_namequinolinium_111_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;">Quinolinium, 1,1'-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-methyl-2(3<i>H</i>)-benzothiazolylidene)-1-propen-1-yl]-,iodide (1:4)</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<span class="graphic"><img src="/books/NBK92611/bin/TOTO3.jpg" alt="Image TOTO3.jpg" /></span>
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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;">TOTO-3</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;">Compounds</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;">Nucleic acids (DNA and RNA)</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;">Nucleic acids</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Optical imaging<br /></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal / contrast:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">TOTO-3</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;">Yes</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Structures of TO-PRO-3 and TOTO-3 (<a class="bk_pop" href="#TOTO-3.REF.1">1</a>).</td></tr></tbody></table></div></div><div id="TOTO-3.Background"><h2 id="_TOTO-3_Background_">Background</h2><p>[<a href="/pubmed?term=TOTO-3" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Quinolinium, 1,1'-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-methyl-2(3<i>H</i>)-benzothiazolylidene)-1-propen-1-yl]-,iodide (1:4), abbreviated as TOTO-3, is a cell-impermeable cyanine acid dye that has a high affinity for nucleic acids (<a class="bk_pop" href="#TOTO-3.REF.1" data-bk-pop-others="TOTO-3.REF.2">1, 2</a>). TOTO-3 shows weak fluorescence in solution but generates significantly increased quantum yield (100- to 1,000-fold increase) when binding to DNA or RNA (<a class="bk_pop" href="#TOTO-3.REF.1" data-bk-pop-others="TOTO-3.REF.3 TOTO-3.REF.4">1, 3, 4</a>). Furthermore, TOTO-3 has a relatively long wavelength (maximum excitation/emission, 640/660 nm). These optical properties make it suitable to assess plasma membrane integrity and to detect DNA with optical imaging (<a class="bk_pop" href="#TOTO-3.REF.2" data-bk-pop-others="TOTO-3.REF.5">2, 5</a>). TOTO-3 is the dimeric form of quinolinium, 4-[3-(3-methyl-2(3<i>H</i>)-benzothiazolylidene)-1-propenyl]-1-[3-(trimethylammonio)propyl]-,diiodide (TO-PRO-3).</p><p>To date, chemotherapy remains the treatment of choice for advanced cancer. However, anticancer agents are often much less efficient against tumor cells <i>in vivo</i> compared with their effect <i>in vitro</i>. Several characteristics of tumors cause this inefficiency, such as high interstitial pressure, increased collagen fibers in the extracellular matrix, acidic microenvironment, and cell membrane (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). Ultrasound has been shown to facilitate the penetration of drugs into tumors by several mechanisms, such as ultrasound-induced hyperthermia, which can enhance drug accumulation in tumor tissue and trigger the release of the drug payload from temperature-sensitive carriers, and ultrasound-induced pores in cell membrane, which can improve cell internalization by increasing the membrane permeability (<a class="bk_pop" href="#TOTO-3.REF.6" data-bk-pop-others="TOTO-3.REF.7">6, 7</a>).</p><p>Molecular imaging has been investigated to monitor and quantify the processes of ultrasound-mediated intracellular drug delivery (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). For this purpose, contrast agents have usually been coupled to or loaded into drug carriers. However, coupling contrast agents to small molecules, as with chemotherapeutic drugs, may change their pharmacokinetics and pharmacodynamics (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). An alternative strategy is co-delivery of drug-mimicking contrast agents and small molecule drugs. Deckers et al. tested the feasibility of using a fluorescent nuclear acid staining dye (TOTO-3) as a model drug to monitor ultrasound-mediated delivery in real time (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). <i>I</i>n vivo fluorescence imaging demonstrated that an optical contrast agent with characteristics similar to an anti-cancer drug may be used for in vivo monitoring of the drug delivery process in real time (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). This chapter summarizes the data obtained with TOTO-3.</p></div><div id="TOTO-3.Synthesis"><h2 id="_TOTO-3_Synthesis_">Synthesis</h2><p>[<a href="/pubmed/21861287" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>TOTO-3 is commercially available.</p></div><div id="TOTO-3.In_Vitro_Studies_Testing_in_Cells"><h2 id="_TOTO-3_In_Vitro_Studies_Testing_in_Cells_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed/21861287" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Deckers et al. analyzed the cell internalization of TOTO-3 after incubation with mouse rectal carcinoma line CMT-93 cells without or with preliminary permeabilization with 0.2% Tween (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). When cells were permeabilized before incubation with TOTO-3, strong fluorescent staining of the cytoplasmic RNA and nucleoli was observed. On the contrary, the TOTO-3 fluorescence was not detectable in cells without permeabilization, confirming that TOTO-3 is a cell-impermeable dye.</p></div><div id="TOTO-3.Animal_Studies"><h2 id="_TOTO-3_Animal_Studies_">Animal Studies</h2><div id="TOTO-3.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed/21861287" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Deckers et al. tested the feasibility of TOTO-3 as a smart probe for in vivo monitoring of ultrasound-mediated intracellular drug delivery (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). RAG 2/g_C mice bearing a CMT-93 tumor on both flanks (<i>n</i> = 8 mice) were first co-injected with TOTO-3 and microbubbles directly into both tumors, and ultrasound (1.5 MHz for 1 min) was then applied to one tumor with the second tumor serving as a control. The time course of ultrasound-mediated intracellular delivery of TOTO-3 was measured with fluorescence imaging. A distinct difference in the fluorescence intensity was observed between the ultrasound-treated and control tumors at 2 h and 4 h after ultrasound application. At these time points, two-fold higher mean signal intensity and an even larger difference in the total and maximum intensities were observed in the ultrasound-treated tumor.</p><p>Epifluorescence microscopy was performed on the excised tumor sections to demonstrate the internalization of TOTO-3 (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). Relatively large areas with TOTO-3 signal were observed in the ultrasound-exposed tumor sections. In contrast, control tumor sections typically showed no fluorescence or only single cells with TOTO-3 uptake. The overall signal intensity was quite weak in both cases.</p><p>The investigators hypothesized that phagocytic cells, such as macrophages, caused ultrasound-independent uptake of TOTO-3, which may explain the observed fluorescence in the control tumors (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). Anti-CD68 staining revealed a significant presence of macrophages in both control and ultrasound-treated tumors. However, TOTO-3 signal was strongly associated with macrophages only in the control tumors. Ultrasound-independent uptake was further confirmed with isolated intraperitoneal macrophages from female Rag-gamma mice after incubation of TOTO-3 with the macrophages (<a class="bk_pop" href="#TOTO-3.REF.2">2</a>). Flow cytometry and confocal microscopy confirmed that macrophages could take up TOTO-3 in an ultrasound-independent manner. The peak fluorescent intensity was in the range of 1 × 10<sup>3</sup> to 1 × 10<sup>4</sup>, comparable to the intensity observed for the positive control macrophages (permeabilized with 0.2% Tween before incubation with TOTO-3). The negative control sample (incubation without TOTO-3 and Tween) showed negligible fluorescence signal.</p></div><div id="TOTO-3.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28dog%20OR%20rabbit%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="TOTO-3.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed/?term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="TOTO-3.Human_Studies"><h2 id="_TOTO-3_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed/?term=21417461" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="TOTO-3.References"><h2 id="_TOTO-3_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="TOTO-3.REF.1">Milanovich N. et al.
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<em>Binding of TO-PRO-3 and TOTO-3 to DNA: fluorescence and hole-burning studies.</em>
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<span><span class="ref-journal">Journal of Physical Chemistry. </span>1996;<span class="ref-vol">100</span>:9181–6.</span></div></dd><dt>2.</dt><dd><div class="bk_ref" id="TOTO-3.REF.2">Deckers R. et al.
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<em>A fluorescent chromophore TOTO-3 as a 'smart probe' for the assessment of ultrasound-mediated local drug delivery in vivo.</em>
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<span><span class="ref-journal">Contrast Media Mol Imaging. </span>2011;<span class="ref-vol">6</span>(4):267–74.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21861287" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21861287</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="TOTO-3.REF.3">Martin R.M., Leonhardt H., Cardoso M.C.
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<em>DNA labeling in living cells.</em>
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<span><span class="ref-journal">Cytometry A. </span>2005;<span class="ref-vol">67</span>(1):45–52.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16082711" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16082711</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="TOTO-3.REF.4">Suzuki T. et al.
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<em>DNA staining for fluorescence and laser confocal microscopy.</em>
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<span><span class="ref-journal">J Histochem Cytochem. </span>1997;<span class="ref-vol">45</span>(1):49–53.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9010468" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9010468</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="TOTO-3.REF.5">Zuliani T. et al.
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<em>Sensitive and reliable JC-1 and TOTO-3 double staining to assess mitochondrial transmembrane potential and plasma membrane integrity: interest for cell death investigations.</em>
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<span><span class="ref-journal">Cytometry A. </span>2003;<span class="ref-vol">54</span>(2):100–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12879456" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12879456</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="TOTO-3.REF.6">Frenkel V.
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<em>Ultrasound mediated delivery of drugs and genes to solid tumors.</em>
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<span><span class="ref-journal">Adv Drug Deliv Rev. </span>2008;<span class="ref-vol">60</span>(10):1193–208.</span> [<a href="/pmc/articles/PMC2491332/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2491332</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/18474406" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18474406</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="TOTO-3.REF.7">Khaibullina A. et al.
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<em>Pulsed high-intensity focused ultrasound enhances uptake of radiolabeled monoclonal antibody to human epidermoid tumor in nude mice.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2008;<span class="ref-vol">49</span>(2):295–302.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18199622" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18199622</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: NBK92611</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/22574338" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">22574338</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/sostoto3/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/sosVT750/" 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/NBK92611/?report=reader">PubReader</a></li><li><a href="/books/NBK92611/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK92611" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK92611" style="display:none" title="Cite this Page"><div class="bk_tt">Shan L. Quinolinium, 1,1'-[1,3-propanediylbis[(dimethyliminio)-3,1-propanediyl]]bis[4-[3-(3-methyl-2(3H)-benzothiazolylidene)-1-propen-1-yl]-,iodide (1:4) 2012 Apr 2 [Updated 2012 May 2]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></div></div></li><li><a href="/books/NBK92611/pdf/Bookshelf_NBK92611.pdf">PDF version of this page</a> (144K)</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="#TOTO-3.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#TOTO-3.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#TOTO-3.In_Vitro_Studies_Testing_in_Cells" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#TOTO-3.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#TOTO-3.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#TOTO-3.References" ref="log$=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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radionuclides</option><option value="("Iron oxide" AND Optical)">Gadolinium and optical</option><option value="(Optical AND (64Cu OR 111In OR 177Lu))">Optical and
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radionuclides</option><option value="(Perfluorocarbon AND (Europium OR Eu3+))">Perfluorocarbon 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=pmc&DbFrom=books&Cmd=Link&LinkName=books_pmc_refs&IdsFromResult=2905448" ref="log$=recordlinks">PMC</a><div class="brieflinkpop offscreen_noflow">PubMed Central citations</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=2905448" ref="log$=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/21861287" ref="ordinalpos=1&linkpos=1&log$=relatedarticles&logdbfrom=pubmed">A fluorescent chromophore TOTO-3 as a 'smart probe' for the assessment of ultrasound-mediated local drug delivery in vivo.</a><span class="source">[Contrast Media Mol Imaging. 2011]</span><div class="brieflinkpop offscreen_noflow">A fluorescent chromophore TOTO-3 as a 'smart probe' for the 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