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<title>64Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-N,N',N,N'-tetraacetic acid conjugated hypericin - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]" /><meta name="citation_title" content="64Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-N,N',N,N'-tetraacetic acid conjugated hypericin" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2011/05/26" /><meta name="citation_author" content="Arvind Chopra" /><meta name="citation_pmid" content="21656982" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK55564/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="64Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-N,N',N,N'-tetraacetic acid conjugated hypericin" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Arvind Chopra" /><meta name="DC.Date" content="2011/05/26" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK55564/" /><meta name="description" content="A common problem encountered with the chemotherapy or radiotherapy of cancer is the development of resistance to these treatments resulting in metastasis of the malignancy. 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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="#__NBK55564_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK55564_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/Fab12A864Cu/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CysdEGF64Cu/" 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="_NBK55564_"><span class="title" itemprop="name"><sup>64</sup>Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-<i>N</i>,<i>N</i>',<i>N</i>,<i>N</i>'-tetraacetic acid conjugated hypericin</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"> [<sup>64</sup>Cu]-bis DOTA-hypericin</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK55564_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK55564_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">May 3, 2011</span>; Last Update: <span itemprop="dateModified">May 26, 2011</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="Hypericin64Cu.T.nc_chemical_name64culabe" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK55564/table/Hypericin64Cu.T.nc_chemical_name64culabe/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Hypericin64Cu.T.nc_chemical_name64culabe_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;"><sup>64</sup>Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-<i>N</i>,<i>N</i>',<i>N</i>,<i>N</i>'-tetraacetic acid conjugated hypericin<br /></td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/57269558" 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=57269558" alt="image 57269558 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>64</sup>Cu]-bis DOTA-hypericin<br /></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;">Tumor necrosis (cell membranes and subcellular organelle membranes)</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;">Other</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;">Positron emission tomography (PET)</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;"><sup>64</sup>Cu</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure of Hypericin for additional information in <a href="http://pubchem.ncbi.nlm.nih.gov/" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.</td></tr></tbody></table></div></div><div id="Hypericin64Cu.Background"><h2 id="_Hypericin64Cu_Background_">Background</h2><p>[<a href="/pubmed?term=hypericin&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>A common problem encountered with the chemotherapy or radiotherapy of cancer is the development of resistance to these treatments resulting in metastasis of the malignancy. Therefore, there is an urgent need to develop new anti-cancer treatments that have a unique mechanism of action and are not prone to the development of drug or radiation resistance (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). Photothermal ablation (PTA) therapy is an emerging technique that uses heat produced from absorbed light to destroy cancer cells. PTA therapy can be performed frequently, has no side effects, and does not promote the development of resistance (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). For PTA therapy, near-infrared (NIR) light is used to deliver a predetermined amount of photothermal energy directly into a tumor, which stimulates photochemical and photothermal reactions within the malignant lesion that are fatal for the cancer cells (<a class="bk_pop" href="#Hypericin64Cu.REF.2">2</a>). In addition, the application of PTA in the presence of a light-absorbing nanoparticles (NPs), such as gold NPs (shells, rods, and cages) or copper sulfide (CuS) NPs, has been shown to enhance efficacy of the therapy (<a class="bk_pop" href="#Hypericin64Cu.REF.3">3</a>). However, many parameters, such as the dose of NIR required to maximize the efficacy of PTA therapy, the number of NPs required for optimal ablation, or how to monitor the treatment noninvasively, remain to be worked out (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>).</p><p>Computed tomography, magnetic resonance imaging, and ultrasonography are currently used to monitor morphological changes that occur after PTA therapy, but alterations in the tissue are visible with these techniques for only 2–3 months after initiation of the treatment (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). It is well known that <sup>18</sup>F-labeled fluorodeoxyglucose ([<sup>18</sup>F]-FDG) is often used with positron emission tomography (PET) to assess the response to cancer therapy, but this imaging modality generates reliable results for only 2–3 weeks after initiation of the treatment. In addition, [<sup>18</sup>F]-FDG can generate false-positive results because it also detects <a href="http://dictionary.webmd.com/terms/inflammation" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">inflammation</a>, <a href="http://www.lungusa.org/lung-disease/sarcoidosis/?gclid=CIapzbbzzqgCFUOo4AodlSW-gA" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">sarcoidosis</a>, and <a href="http://www.merckmanuals.com/home/sec17/ch197/ch197a.html" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">fungal</a> and <a href="http://www.webmd.com/lung/tc/tuberculosis-tb-topic-overview" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">tuberculosis</a> infections (lesions from these conditions show an upregulated glucose metabolism similar to that of cancer cells) (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>, <a class="bk_pop" href="#Hypericin64Cu.REF.4">4</a>). Hypericin, a naturally occurring polycyclic quinone that can be isolated from the plant <a href="http://plants.usda.gov/java/profile?symbol=HYPE" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"><i>Hypericum perforatum</i></a> or chemically synthesized, has been investigated for the photodynamic therapy of cancer and other conditions (<a class="bk_pop" href="#Hypericin64Cu.REF.5">5</a>). Although the exact mechanism of action of this compound is not known, several reports suggest that multiple cellular pathways participating in the survival, <a href="http://dictionary.webmd.com/terms/necrosis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">necrosis</a>, or <a href="http://dictionary.webmd.com/terms/apoptosis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">apoptosis</a> of the cell are involved in bringing about the activity of hypericin as discussed elsewhere (<a class="bk_pop" href="#Hypericin64Cu.REF.5">5</a>, <a class="bk_pop" href="#Hypericin64Cu.REF.6">6</a>). Hypericin is considered a nonporphyrin agent that binds to necrotic tissues, and <sup>123</sup>I-labeled hypericin has been shown to detect tissue necrosis in the liver and the heart [<a href="/pubmed?term=123I-hypericin" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]. Song et al. synthesized <sup>64</sup>Cu-labeled bis-1,4,7,10-tetraazacyclododecane-<i>N</i>,<i>N</i>',<i>N</i>,<i>N</i>'-tetraacetic acid (DOTA)-conjugated hypericin ([<sup>64</sup>Cu]-bis-DOTA-hypericin) and used it to evaluate the response of xenograft human <a href="http://www.atcc.org/ATCCAdvancedCatalogSearch/ProductDetails/tabid/452/Default.aspx?ATCCNum=HTB-20&Template=cellBiology" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">BT474 breast carcinoma cell</a> tumors in nude mice subjected to PTA treatment in presence of copper sulfide nanoparticles (CuS NPs) (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). The biodistribution of [<sup>64</sup>Cu]-bis-DOTA-hypericin was also investigated in these animals.</p><div id="Hypericin64Cu.Other_Sources_of_Informati"><h3>Other Sources of Information</h3><p>Related chapters in <a href="/books/?term=Hypericin+AND+micad%5Bbook%5D&view=chapter&p%24a=&p%24l=PBooksLayout&p%24st=books" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">MICAD</a></p><p><a href="http://clinicaltrials.gov/ct2/results?term=Hypericin" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Clinical trials</a> with hypericin</p></div></div><div id="Hypericin64Cu.Synthesis"><h2 id="_Hypericin64Cu_Synthesis_">Synthesis</h2><p>[<a href="/gene?term=64Cu-bis-DOTA-Hypericin%20synthesis&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The synthesis of [<sup>64</sup>Cu]-bis-DOTA-hypericin has been described by Song et al. (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). The radiochemical yield and purity were reported to be 97.7% and >95%, respectively, as determined with radio-high-performance liquid chromatography. The stability and specific activity of the final product were not reported.</p></div><div id="Hypericin64Cu.In_Vitro_Studies_Testing_i"><h2 id="_Hypericin64Cu_In_Vitro_Studies_Testing_i_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed?term=64Cu-bis-DOTA-hypericin&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>A higher number of BT474 cells died when they were exposed to CuS NPs and treated with a NIR laser compared to cells exposed to either the CuS NP alone or the laser alone (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). The PTA-treated cells were reported to have damaged membranes as observed with uptake studies of <a href="http://www.moleculardevices.com/Documents/general-documents/mkt-appnotes/microplate-appnotes/Maxline_AppNote_43%20LIVEDEAD.pdf" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">ethidium homodimer</a>, a red fluorescent dye impermeable to living cells.</p><p>In another study, BT474 cells exposed to CuS NPs and treated with a NIR laser showed a significantly higher (<i>P</i> = 0.04) uptake of [<sup>64</sup>Cu]-bis-DOTA-hypericin compared to cells exposed to the CuS NPs or the NIR laser alone (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). Cell exposed to the CuS NPs and the NIR laser were reported to have a much higher uptake of the red, cell-impermeable EthD-1 dye compared to cells treated with the CuS or the NIR laser alone. This suggested the thermal ablation treatment was more effective (i.e. there was an increased cell death) in presence of the CuS NPs and the CuS NPs or the NIR alone had little effect on the cells. To determine the binding specificity of [<sup>64</sup>Cu]-bis-DOTA-hypericin, cells were treated with CuS NPs and NIR laser and exposed to [<sup>64</sup>Cu]-bis-DOTA-hypericin in the presence of excess non-radioactive hypericin. Binding of the labeled compound to these cells was reduced by 54% (<i>P</i> = 0.007) compared to the binding of cells exposed only to [<sup>64</sup>Cu]-bis-DOTA-hypericin (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). This strongly indicated that the labeled hypericin targeted the same cell membrane components as the native hypericin.</p></div><div id="Hypericin64Cu.Animal_Studies"><h2 id="_Hypericin64Cu_Animal_Studies_">Animal Studies</h2><div id="Hypericin64Cu.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed?term=64Cu-bis-DOTA-hypericin%20rodentia&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of [<sup>64</sup>Cu]-bis-DOTA-hypericin was investigated in nude mice (<i>n</i> = 4–5 animals/time point) bearing BT474 cell tumors as described by Song et al. (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). Animals in the treated group (TG) received an intratumoral injection of CuS NPs (10 μL, 4 × 10<sup>13</sup> NP/mL) and were irradiated with NIR laser 24 h later (808 nm, 12 W/cm<sup>2</sup> for 3 min). Control animals (non-targeted (N-TG)) were not injected with the NPs or irradiated with the NIR laser. Both groups of mice were injected with [<sup>64</sup>Cu]-bis-DOTA-hypericin (5.55–7.4 MBq/0.1 mL (150–200 µCi/0.1 mL)) through the tail vein. Small-animal PET scans were subsequently performed on the mice at 2, 6, and 24 h postinjection (p.i.) while the animals were under anesthesia. After the last scan, the mice were euthanized, and major organs (including tumors) were harvested from the animals to determine the amount of radioactivity accumulated in the various tissues. Data were presented as percent of injected dose per gram tissue (% ID/g).</p><p>Small-animal PET scans of the animals revealed that tumors on the TG mice were clearly visible from 2 h to 24 h p.i., and tumors on the N-TG mice showed little accumulation of the tracer (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). From quantitative imaging analysis, the amount of radioactivity in tumors of the TG group was reported to be 0.80 ± 0.14% ID/g (<i>P</i> = 0.024), 1.19 ± 0.45% ID/g (<i>P</i> = 0.019), and 1.49 ± 0.68% ID/g (<i>P</i> = 0.039), at 2, 6, and 24 h p.i., respectively, compared to 0.57 ± 0.06% ID/g, 0.50 ± 0.63% ID/g, and 0.53 ± 0.18% ID/g at the same time points for animals in the N-TG group.</p><p>Biodistribution data from this study showed that the tumors of the TG and N-TG groups were the only tissues to show a significant difference in the accumulation of radioactivity (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). The uptake of label in tumors of the TG mice (1.71 ± 0.43% ID/g) was significantly higher (<i>P</i> = 0.017) than that observed in tumors of the N-TG mice (0.76 ± 0.19% ID/g). Tissue necrosis and the presence of radioactivity at the tumor site were confirmed with hematoxylin and eosin staining and autoradiography of tumor sections, respectively, as described by Song et al. (<a class="bk_pop" href="#Hypericin64Cu.REF.1">1</a>). All other organs from the animals in both groups showed a comparable uptake of the tracer. This suggests that radioactivity derived from [<sup>64</sup>Cu]-bis-DOTA-hypericin had a binding specificity for necrotic tissue developed in the tumors after the PTA treatment. No blocking studies were reported.</p><p>On the basis of results obtained from this study, the investigators concluded that [<sup>64</sup>Cu]-bis-DOTA-hypericin can be used for the noninvasive assessment of tumor response to CuS NP-mediated PTA in mice.</p></div><div id="Hypericin64Cu.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed?term=64Cu-bis-DOTA-hypericin%20Non-Primate%20Mammals&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div><div id="Hypericin64Cu.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed?term=64Cu-bis-DOTA-hypericin%20Non-Human%20Primates&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div></div><div id="Hypericin64Cu.Human_Studies"><h2 id="_Hypericin64Cu_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed?term=64Cu-bis-DOTA-hypericin%20Human%20Studies&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publications are currently available.</p></div><div id="Hypericin64Cu.Supplemental_Information"><h2 id="_Hypericin64Cu_Supplemental_Information_">Supplemental Information</h2><p>[<a href="/books/n/micad/disclaimer/">Disclaimers</a>]</p><p>No information is currently available.</p></div><div id="Hypericin64Cu.References"><h2 id="_Hypericin64Cu_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="Hypericin64Cu.REF.1">Song, S., C. Xiong, M. Zhou, W. Lu, Q. Huang, G. Ku, J. Zhao, L.G. Flores, Jr., Y. Ni, and C. Li, Small-Animal PET of Tumor Damage Induced by Photothermal Ablation with 64Cu-Bis-DOTA-Hypericin. J Nucl Med, 2011. [<a href="https://pubmed.ncbi.nlm.nih.gov/21498539" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21498539</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="Hypericin64Cu.REF.2">Vogel A., Venugopalan V. Mechanisms of pulsed laser ablation of biological tissues. <span><span class="ref-journal">Chem Rev. </span>2003;<span class="ref-vol">103</span>(2):577–644.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12580643" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12580643</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="Hypericin64Cu.REF.3">Zhou M., Zhang R., Huang M., Lu W., Song S., Melancon M.P., Tian M., Liang D., Li C. A Chelator-Free Multifunctional [64Cu]CuS Nanoparticle Platform for Simultaneous Micro-PET/CT Imaging and Photothermal Ablation Therapy. <span><span class="ref-journal">Journal of the American Chemical Society. </span>2010;<span class="ref-vol">132</span>(43):15351–15358.</span> [<a href="/pmc/articles/PMC2966020/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2966020</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20942456" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20942456</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="Hypericin64Cu.REF.4">Culverwell A.D., Scarsbrook A.F., Chowdhury F.U. False-positive uptake on 2-[(1)F]-fluoro-2-deoxy-D-glucose (FDG) positron-emission tomography/computed tomography (PET/CT) in oncological imaging. <span><span class="ref-journal">Clin Radiol. </span>2011;<span class="ref-vol">66</span>(4):366–82.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21356398" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21356398</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="Hypericin64Cu.REF.5">Karioti A., Bilia A.R. Hypericins as potential leads for new therapeutics. <span><span class="ref-journal">Int J Mol Sci. </span>2010;<span class="ref-vol">11</span>(2):562–94.</span> [<a href="/pmc/articles/PMC2852855/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2852855</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20386655" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20386655</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="Hypericin64Cu.REF.6">Theodossiou T.A., Hothersall J.S., De Witte P.A., Pantos A., Agostinis P. The multifaceted photocytotoxic profile of hypericin. <span><span class="ref-journal">Mol Pharm. </span>2009;<span class="ref-vol">6</span>(6):1775–89.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19739671" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19739671</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/NBK55564/?report=reader">PubReader</a></li><li><a href="/books/NBK55564/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK55564" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK55564" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. 64Cu-Labeled bis-1,4,7,10-tetraazacyclododecane-N,N',N,N'-tetraacetic acid conjugated hypericin. 2011 May 3 [Updated 2011 May 26]. 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/NBK55564/pdf/Bookshelf_NBK55564.pdf">PDF version of this page</a> (138K)</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="#Hypericin64Cu.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#Hypericin64Cu.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#Hypericin64Cu.In_Vitro_Studies_Testing_i" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#Hypericin64Cu.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#Hypericin64Cu.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#Hypericin64Cu.Supplemental_Information" ref="log$=inpage&link_id=inpage">Supplemental Information</a></li><li><a href="#Hypericin64Cu.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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href="/books/?Db=pcsubstance&DbFrom=books&Cmd=Link&LinkName=books_pcsubstance&IdsFromResult=2484824" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=2484824" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/21498539" ref="ordinalpos=1&linkpos=1&log$=relatedarticles&logdbfrom=pubmed">Small-animal PET 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