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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="Cypate-2-Deoxy-d-glucose" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2012/11/15" /><meta name="citation_author" content="Kam Leung" /><meta name="citation_pmid" content="23166963" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK114194/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="Cypate-2-Deoxy-d-glucose" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Kam Leung" /><meta name="DC.Date" content="2012/11/15" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK114194/" /><meta name="description" content="Optical fluorescence imaging is increasingly used to monitor biological functions of specific targets in small animals (1-3). 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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="#__NBK114194_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK114194_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/soscypate/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/cyp-GlcN/" 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="_NBK114194_"><span class="title" itemprop="name">Cypate-2-Deoxy-<span class="small-caps">d</span>-glucose</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">Cypate-2DG</div><p class="contrib-group"><span itemprop="author">Kam Leung</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK114194_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK114194_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kam Leung</span>, PhD<div class="affiliation small">National for Biotechnology Information, NLM, NIH, Bethesda, MD<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">August 18, 2012</span>; Last Update: <span itemprop="dateModified">November 15, 2012</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="Cypate-2DG.T.nc_chemical_namecypate2deox" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK114194/table/Cypate-2DG.T.nc_chemical_namecypate2deox/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Cypate-2DG.T.nc_chemical_namecypate2deox_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:middle;">Cypate-2-Deoxy-<span class="small-caps">d</span>-glucose</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/152146811" 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=152146811" alt="image 152146811 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:middle;">Cypate-2DG</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:middle;"></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;">Glucose transporters, hexokinases</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;">Transporter, enzyme</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:middle;">Optical, near-infrared fluorescence (NIR) imaging</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:middle;">Cypate</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:middle;">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 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="Cypate-2DG.Background"><h2 id="_Cypate-2DG_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Optical fluorescence imaging is increasingly used to monitor biological functions of specific targets in small animals (<a class="bk_pop" href="#Cypate-2DG.REF.1" data-bk-pop-others="Cypate-2DG.REF.2 Cypate-2DG.REF.3">1-3</a>). However, the intrinsic fluorescence of biomolecules poses a problem when fluorophores that absorb visible light (350–650 nm) are used. Near-infrared (NIR) fluorescence (650–900 nm) detection avoids the natural background fluorescence interference of biomolecules, providing a high contrast between target and background tissues. NIR fluorophores have wider dynamic range and minimal background fluorescence as a result of reduced scattering compared with visible fluorescence detection. They also have high sensitivity, resulting from low background fluorescence, and high extinction coefficients, which provide high quantum yields. The NIR region is also compatible with solid-state optical components, such as diode lasers and silicon detectors. NIR fluorescence imaging is a noninvasive complement to radionuclide imaging in small animals or with probes in close proximity to the target in humans (<a class="bk_pop" href="#Cypate-2DG.REF.4">4</a>). Among the various optical imaging agents, only indocyanine green (<a href="http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15096" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">ICG</a>), with NIR fluorescence absorption at 780 nm and emission at 820 nm, is approved by the United States Food and Drug Administration for clinical applications in angiography, blood flow evaluation, and liver function assessment (<a class="bk_pop" href="#Cypate-2DG.REF.5" data-bk-pop-others="Cypate-2DG.REF.6 Cypate-2DG.REF.7 Cypate-2DG.REF.8">5-8</a>). It is also under evaluation in several <a href="http://clinicaltrials.gov/ct2/results?term=indocyanine+green" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">clinical trials</a> for other applications, such as optical imaging and mapping of both the lymphatic vessels and lymph nodes in cancer patients for surgical dissection of tumor cells and endoscopic imaging of the pancreas and colon.</p><p>The phosphorylation of glucose, an initial and important step in cellular metabolism, is catalyzed by hexokinases (HKs) (<a class="bk_pop" href="#Cypate-2DG.REF.9">9</a>). There are four HKs in mammalian tissues (HKI–HKIV). HKI, HKII, and HKIII have molecular weights of ~100,000 each; HKI is found mainly in the brain, and HKII is insulin-sensitive and is found in adipose and muscle cells. HKIV, also known as glucokinase, has a molecular weight of ~50,000 and is specific to the liver and pancreas. Most brain HK is bound to mitochondria, enabling coordination between glucose consumption and oxidation. Tumor cells are known to be highly glycolytic because of increased expression of glycolytic enzymes and HK activity (<a class="bk_pop" href="#Cypate-2DG.REF.10">10</a>), which was detected in tumors from patients with lung, gastrointestinal, and breast cancers. The HKs, by converting glucose to glucose-6-phosphate, help maintain the downhill gradient that results in the transport of glucose into cells through the facilitative glucose transporters (GLUT1–13) (<a class="bk_pop" href="#Cypate-2DG.REF.11">11</a>). GLUT1 is considered to be the main transporter of glucose uptake. GLUT4 and HKII are the major transporter and HK isoform in skeletal muscle, heart, and adipose tissue, wherein insulin promotes glucose utilization. HKIV is associated with GLUT2 in liver and pancreatic β cells.</p><p>2-Deoxy-<span class="small-caps">d</span>-glucose (2DG) was first developed to inhibit glucose utilization by cancer cells (<a class="bk_pop" href="#Cypate-2DG.REF.12">12</a>). HKs phosphorylate 2DG to 2DG-6-phosphate, which inhibits phosphorylation of glucose. 2-[<sup>18</sup>F]Fluoro-2-deoxy-<span class="small-caps">d</span>-glucose (<a href="/books/NBK23335/" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">[<sup>18</sup>F]FDG</a>) was later developed for molecular imaging studies (<a class="bk_pop" href="#Cypate-2DG.REF.13">13</a>). FDG is moved into cells by glucose transporters, where it is phosphorylated by HK to FDG-6-phosphate. FDG-6-phosphate cannot be metabolized further in the glycolytic pathway and remains in the cells. Tumor cells do not contain a sufficient amount of glucose-6-phosphatase to reverse the phosphorylation. The elevated rates of glycolysis and glucose transport in many types of tumor cells and activated cells enhance the uptake of FDG in these cells relative to other normal cells. Positron emission tomography (PET) with [<sup>18</sup>F]FDG has been used to assess alterations in glucose metabolism in brain, cancer, cardiovascular diseases, Alzheimer’s disease and other central nervous system disorders, and infectious, autoimmune, and inflammatory diseases (<a class="bk_pop" href="#Cypate-2DG.REF.14" data-bk-pop-others="Cypate-2DG.REF.15 Cypate-2DG.REF.16 Cypate-2DG.REF.17 Cypate-2DG.REF.18 Cypate-2DG.REF.19">14-19</a>). Various NIR dyes (such as cypate, Cy5.5, and IRDye800CW) were conjugated to 2DG (<a class="bk_pop" href="#Cypate-2DG.REF.20" data-bk-pop-others="Cypate-2DG.REF.21 Cypate-2DG.REF.22">20-22</a>) as optical imaging agents for <i>in vivo</i> imaging of glucose utilization in tumors in mice. Cypate is a reactive carbocyanine dye, which is derived from indocyanine green (ICG) (<a class="bk_pop" href="#Cypate-2DG.REF.23">23</a>). Cypate exhibits an absorbance maximum at 778 nm and an emission maximum at 805 nm, with a high extinction coefficient of 224,000 M−<sup>1</sup>cm−<sup>1</sup>. Cypate is a lipophilic dye and contains two carboxyl functional groups for covalent conjugation to the amino group of biomolecules. Guo et al. (<a class="bk_pop" href="#Cypate-2DG.REF.24">24</a>) evaluated cypate-2DG for <i>in vivo</i> NIR optical imaging in tumor-bearing mice.</p><div id="Cypate-2DG.Related_Resource_Links"><h3>Related Resource Links:</h3><ul><li class="half_rhythm"><div>Chapters in MICAD (<a href="/books?term=(hexokinase%20OR%20hexokinases)%20AND%20micad%5Bbook%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Hexokinase</a>, <a href="/books?term=glucose%20transporters%20%20AND%20micad%5Bbook%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">glucose transporter</a>, <a href="/books?term=ICG%5BAll%20Fields%5D%20AND%20micad%5Bbook%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">ICG</a>, <a href="/books?term=Cypate%5BAll%20Fields%5D%20AND%20micad%5Bbook%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Cypate</a>)</div></li><li class="half_rhythm"><div>Gene information in NCBI (<a href="/gene?term=hexokinase%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Hexokinase</a>, <a href="/gene/6513" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">GLUT1</a>)</div></li><li class="half_rhythm"><div>Articles in Online Mendelian Inheritance in Man (OMIM) (<a href="/omim?Db=omim&Cmd=DetailsSearch&Term=hexokinase%5BAll+Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Hexokinase</a>, <a href="/omim/138140" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">GLUT1</a>)</div></li><li class="half_rhythm"><div>Clinical trials (<a href="http://www.clinicaltrials.gov/ct2/results?term=FDG" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">[<sup>18</sup>F]FDG</a>)</div></li><li class="half_rhythm"><div>Drug information in FDA (<a href="http://google2.fda.gov/search?q=%5B18F%5DFDG&client=FDAgov&site=FDAgov&lr=&proxystylesheet=FDAgov&output=xml_no_dtd&getfields=*&x=3&y=9" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">[<sup>18</sup>F]FDG</a>)</div></li></ul></div></div><div id="Cypate-2DG.Synthesis"><h2 id="_Cypate-2DG_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG+synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Cypate-<i>N</i>-hydroxysuccinimide ester (0.0128 mmol) was reacted with 2-amino-2-DG (0.064 mmol) for 18 h at room temperature in sodium phosphate buffer (pH 9) (<a class="bk_pop" href="#Cypate-2DG.REF.24">24</a>). Cypate-2DG was purified with high-performance liquid chromatography and verified with mass spectroscopy. There were two 2DG molecules per cypate-2DG. The yield of cypate-2DG was ~35%, with 90% purity. Cypate-2DG displayed similar spectral properties as cypate, with maximum absorption at 782 nm and maximum emission at 821 nm.</p></div><div id="Cypate-2DG.In_Vitro_Studies_Testing_in_C"><h2 id="_Cypate-2DG_In_Vitro_Studies_Testing_in_C_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG+in+vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><i>In vitro</i> uptake studies of rhodamine-2DG (RhB-2DG) were performed with MCF-7/estradiol, MDA-MB-435, U87MG, and MCF-7 tumor cells in culture (<a class="bk_pop" href="#Cypate-2DG.REF.24">24</a>). These studies showed that high, medium, and low fluorescence intensity values correlated with the tumors' GLUT1 expression levels, respectively. Fluorescence microscopy showed that RhB-2DG accumulated in the cytoplasm of the tumor cells. Excess 2DG was able to block the NIR fluorescence signal in the cytoplasm.</p></div><div id="Cypate-2DG.Animal_Studies"><h2 id="_Cypate-2DG_Animal_Studies_">Animal Studies</h2><div id="Cypate-2DG.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG+rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Guo et al. (<a class="bk_pop" href="#Cypate-2DG.REF.24">24</a>) performed <i>in vivo</i> NIR fluorescence imaging studies in nude mice (<i>n</i> = 5) bearing GLUT1-expressing MCF-7/estradiol xenografts at 0.5–48 h after intravenous injection of cypate-2DG (10 nmol per mouse). Cypate-2DG accumulated mainly in the tumors, with a peak tumor/muscle ratio of 14.49 ± 0.28 at 24 h; the tumor/muscle ratio gradually decreased to ~13 at 48 h. The kidney and liver exhibited strong and moderate fluorescence signals, respectively. Cypate-2DG is excreted mainly by the renal pathway and partially by the hepatobiliary pathway. <i>Ex vivo</i> NIR fluorescence imaging showed that the tumors exhibited the highest fluorescence intensity (tissue/muscle ratio, ~22), followed by the kidney (~13), liver (~9), lung (~8), intestine (~7), spleen (~4), and heart (~3). No blocking experiment was performed.</p><p>In the next series of experiments, NIR fluorescence imaging studies were performed in nude mice (<i>n</i> = 5) bearing GLUT1-expressing U87MG xenografts at 0.5–48 h after intravenous injection of cypate-2DG or cypate (10 nmol per mouse). Cypate-2DG accumulated mainly in the tumors, with a peak tumor/muscle ratio of 9 at 24 h; the tumor/muscle ratio gradually decreased to 6 at 48 h. The kidneys and liver exhibited strong and moderate fluorescence signals, respectively. On the other hand, little accumulation of cypate was observed in the tumors. The liver and kidneys exhibited strong and moderate fluorescence signals, respectively. The studies of cypate-2DG in different tumors with different expression of GLUT1 showed good correlation of tumor fluorescence intensities and GLUT1 expression levels (<i>P</i> < 0.05–0.001). No blocking experiment was performed.</p></div><div id="Cypate-2DG.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG+and+(dog+or+sheep+or+pig+or+rabbit)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="Cypate-2DG.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG+and+(primate+not+human)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="Cypate-2DG.Human_Studies"><h2 id="_Cypate-2DG_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=Cypate-2DG+human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="Cypate-2DG.References"><h2 id="_Cypate-2DG_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.1">Achilefu S.
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<em>Lighting up tumors with receptor-specific optical molecular probes.</em>
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<span><span class="ref-journal">Technol Cancer Res Treat. </span>2004;<span class="ref-vol">3</span>(4):393–409.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15270591" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15270591</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.2">Becker A., Hessenius C., Licha K., Ebert B., Sukowski U., Semmler W., Wiedenmann B., Grotzinger C.
|
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<em>Receptor-targeted optical imaging of tumors with near-infrared fluorescent ligands.</em>
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<span><span class="ref-journal">Nat Biotechnol. </span>2001;<span class="ref-vol">19</span>(4):327–31.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11283589" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11283589</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.3">Ntziachristos V., Bremer C., Weissleder R.
|
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<em>Fluorescence imaging with near-infrared light: new technological advances that enable in vivo molecular imaging.</em>
|
||
<span><span class="ref-journal">Eur Radiol. </span>2003;<span class="ref-vol">13</span>(1):195–208.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12541130" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12541130</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.4">Tung C.H.
|
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<em>Fluorescent peptide probes for in vivo diagnostic imaging.</em>
|
||
<span><span class="ref-journal">Biopolymers. </span>2004;<span class="ref-vol">76</span>(5):391–403.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15389488" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15389488</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.5">Yannuzzi, L.A., <em>Indocyanine green angiography: a perspective on use in the clinical setting.</em> Am J Ophthalmol, 2011<strong>151</strong>(5): p. 745-751 e1. [<a href="https://pubmed.ncbi.nlm.nih.gov/21501704" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21501704</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.6">Yamamoto M., Sasaguri S., Sato T.
|
||
<em>Assessing intraoperative blood flow in cardiovascular surgery.</em>
|
||
<span><span class="ref-journal">Surg Today. </span>2011;<span class="ref-vol">41</span>(11):1467–74.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21969147" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21969147</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.7">Schaafsma B.E., Mieog J.S., Hutteman M., van der Vorst J.R., Kuppen P.J., Lowik C.W., Frangioni J.V., van de Velde C.J., Vahrmeijer A.L.
|
||
<em>The clinical use of indocyanine green as a near-infrared fluorescent contrast agent for image-guided oncologic surgery.</em>
|
||
<span><span class="ref-journal">J Surg Oncol. </span>2011;<span class="ref-vol">104</span>(3):323–32.</span> [<a href="/pmc/articles/PMC3144993/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3144993</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/21495033" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21495033</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.8">Manizate F., Hiotis S.P., Labow D., Roayaie S., Schwartz M.
|
||
<em>Liver functional reserve estimation: state of the art and relevance for local treatments: the Western perspective.</em>
|
||
<span><span class="ref-journal">J Hepatobiliary Pancreat Sci. </span>2010;<span class="ref-vol">17</span>(4):385–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19936599" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19936599</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.9">Smith T.A.
|
||
<em>Mammalian hexokinases and their abnormal expression in cancer.</em>
|
||
<span><span class="ref-journal">Br J Biomed Sci. </span>2000;<span class="ref-vol">57</span>(2):170–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10912295" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10912295</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.10">Suolinna E.M., Haaparanta M., Paul R., Harkonen P., Solin O., Sipila H.
|
||
<em>Metabolism of 2-[18F]fluoro-2-deoxyglucose in tumor-bearing rats: chromatographic and enzymatic studies.</em>
|
||
<span><span class="ref-journal">Int J Rad Appl Instrum B. </span>1986;<span class="ref-vol">13</span>(5):577–81.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/3818323" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 3818323</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.11">Wood I.S., Trayhurn P.
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<em>Glucose transporters (GLUT and SGLT): expanded families of sugar transport proteins.</em>
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||
<span><span class="ref-journal">Br J Nutr. </span>2003;<span class="ref-vol">89</span>(1):3–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12568659" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12568659</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.12">Laszlo J., Humphreys S.R., Goldin A.
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<em>Effects of glucose analogues (2-deoxy-D-glucose, 2-deoxy-D-galactose) on experimental tumors.</em>
|
||
<span><span class="ref-journal">J Natl Cancer Inst. </span>1960;<span class="ref-vol">24</span>:267–81.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14414406" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14414406</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.13">Fowler J.S., Ido T.
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<em>Initial and subsequent approach for the synthesis of 18FDG.</em>
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<span><span class="ref-journal">Semin Nucl Med. </span>2002;<span class="ref-vol">32</span>(1):6–12.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11839070" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11839070</span></a>]</div></dd><dt>14.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.14">Phelps M.E.
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<em>PET: the merging of biology and imaging into molecular imaging.</em>
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<em>Positron emission tomography: human brain function and biochemistry.</em>
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<span><span class="ref-journal">Science. </span>1985;<span class="ref-vol">228</span>(4701):799–809.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2860723" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2860723</span></a>]</div></dd><dt>16.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.16">Phelps M.E., Mazziotta J.C., Huang S.C.
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<span><span class="ref-journal">J Cereb Blood Flow Metab. </span>1982;<span class="ref-vol">2</span>(2):113–62.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6210701" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 6210701</span></a>]</div></dd><dt>17.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.17">Rohren E.M., Turkington T.G., Coleman R.E.
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<em>Clinical applications of PET in oncology.</em>
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<span><span class="ref-journal">Radiology. </span>2004;<span class="ref-vol">231</span>(2):305–32.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15044750" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15044750</span></a>]</div></dd><dt>18.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.18">Sokoloff L.
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<em>Basic principles in imaging of regional cerebral metabolic rates.</em>
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<span><span class="ref-journal">Res Publ Assoc Res Nerv Ment Dis. </span>1985;<span class="ref-vol">63</span>:21–49.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/2992057" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2992057</span></a>]</div></dd><dt>19.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.19">Spence A.M., Mankoff D.A., Muzi M.
|
||
<em>Positron emission tomography imaging of brain tumors.</em>
|
||
<span><span class="ref-journal">Neuroimaging Clin N Am. </span>2003;<span class="ref-vol">13</span>(4):717–39.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15024957" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15024957</span></a>]</div></dd><dt>20.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.20">Kovar J.L., Volcheck W., Sevick-Muraca E., Simpson M.A., Olive D.M.
|
||
<em>Characterization and performance of a near-infrared 2-deoxyglucose optical imaging agent for mouse cancer models.</em>
|
||
<span><span class="ref-journal">Anal Biochem. </span>2009;<span class="ref-vol">384</span>(2):254–62.</span> [<a href="/pmc/articles/PMC2720560/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2720560</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/18938129" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18938129</span></a>]</div></dd><dt>21.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.21">Cheng Z., Levi J., Xiong Z., Gheysens O., Keren S., Chen X., Gambhir S.S.
|
||
<em>Near-infrared fluorescent deoxyglucose analogue for tumor optical imaging in cell culture and living mice.</em>
|
||
<span><span class="ref-journal">Bioconjug Chem. </span>2006;<span class="ref-vol">17</span>(3):662–9.</span> [<a href="/pmc/articles/PMC3191878/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3191878</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/16704203" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16704203</span></a>]</div></dd><dt>22.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.22">Chen Y., Zheng G., Zhang Z.H., Blessington D., Zhang M., Li H., Liu Q., Zhou L., Intes X., Achilefu S., Chance B.
|
||
<em>Metabolism-enhanced tumor localization by fluorescence imaging: in vivo animal studies.</em>
|
||
<span><span class="ref-journal">Opt Lett. </span>2003;<span class="ref-vol">28</span>(21):2070–2.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14587818" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14587818</span></a>]</div></dd><dt>23.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.23">Ye Y., Bloch S., Kao J., Achilefu S.
|
||
<em>Multivalent carbocyanine molecular probes: synthesis and applications.</em>
|
||
<span><span class="ref-journal">Bioconjug Chem. </span>2005;<span class="ref-vol">16</span>(1):51–61.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15656575" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15656575</span></a>]</div></dd><dt>24.</dt><dd><div class="bk_ref" id="Cypate-2DG.REF.24">Guo J., Du C., Shan L., Zhu H., Xue B., Qian Z., Achilefu S., Gu Y.
|
||
<em>Comparison of near-infrared fluorescent deoxyglucose probes with different dyes for tumor diagnosis in vivo.</em>
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||
<span><span class="ref-journal">Contrast Media Mol Imaging. </span>2012;<span class="ref-vol">7</span>(3):289–301.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/22539399" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 22539399</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: NBK114194</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/23166963" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">23166963</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/soscypate/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/cyp-GlcN/" 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/NBK114194/?report=reader">PubReader</a></li><li><a href="/books/NBK114194/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK114194" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK114194" style="display:none" title="Cite this Page"><div class="bk_tt">Leung K. Cypate-2-Deoxy-d-glucose. 2012 Aug 18 [Updated 2012 Nov 15]. 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/NBK114194/pdf/Bookshelf_NBK114194.pdf">PDF version of this page</a> (152K)</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="#Cypate-2DG.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#Cypate-2DG.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#Cypate-2DG.In_Vitro_Studies_Testing_in_C" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#Cypate-2DG.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#Cypate-2DG.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#Cypate-2DG.References" ref="log$=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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<p class="address_footer text-white">National Library of Medicine<br />
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<a href="https://www.google.com/maps/place/8600+Rockville+Pike,+Bethesda,+MD+20894/@38.9959508,-77.101021,17z/data=!3m1!4b1!4m5!3m4!1s0x89b7c95e25765ddb:0x19156f88b27635b8!8m2!3d38.9959508!4d-77.0988323" class="text-white" target="_blank" rel="noopener noreferrer">8600 Rockville Pike<br />
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Bethesda, MD 20894</a></p>
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<p><a href="https://www.nlm.nih.gov/web_policies.html" class="text-white">Web Policies</a><br />
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<a href="https://www.nih.gov/institutes-nih/nih-office-director/office-communications-public-liaison/freedom-information-act-office" class="text-white">FOIA</a><br />
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<a href="https://www.hhs.gov/vulnerability-disclosure-policy/index.html" class="text-white" id="vdp">HHS Vulnerability Disclosure</a></p>
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<p><a class="supportLink text-white" href="https://support.nlm.nih.gov/">Help</a><br />
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<a href="https://www.nlm.nih.gov/accessibility.html" class="text-white">Accessibility</a><br />
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<a href="https://www.nlm.nih.gov/careers/careers.html" class="text-white">Careers</a></p>
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<a class="text-white" href="//www.nlm.nih.gov/">NLM</a>
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<a class="text-white" href="https://www.nih.gov/">NIH</a>
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<a class="text-white" href="https://www.hhs.gov/">HHS</a>
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<a class="text-white" href="https://www.usa.gov/">USA.gov</a>
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