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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="#__NBK44812_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK44812_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/AB50_Cy5/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CyRAFTRGD/" 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="_NBK44812_"><span class="title" itemprop="name">Cy5-labeled aza-peptidyl Pro-Asn epoxide</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">LP-1</div><p class="contrib-group"><span itemprop="author">Liang Shan</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK44812_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK44812_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">May 12, 2010</span>; Last Update: <span itemprop="dateModified">June 3, 2010</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="LP-1.T.nc_Chemical_nameCy5labeled_azapep" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK44812/table/LP-1.T.nc_Chemical_nameCy5labeled_azapep/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__LP-1.T.nc_Chemical_nameCy5labeled_azapep_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;">Cy5-labeled aza-peptidyl Pro-Asn epoxide</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;"></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;">LP-1</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;">Legumain probe 1</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;">Legumain/Asparaginyl endopeptidase</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;">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:top;">Optical imaging</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;">Cy5</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;">No structure is available.</td></tr></tbody></table></div></div><div id="LP-1.Background"><h2 id="_LP-1_Background_">Background</h2><p>[<a href="/pubmed/?term=cysteine+cathepsins" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Legumain or asparaginyl endopeptidase is a lysosomal cysteine protease that cleaves protein substrates on the C-terminal side of asparagine and, occasionally, aspartic acid residues (<a class="bk_pop" href="#LP-1.REF.1" data-bk-pop-others="LP-1.REF.2 LP-1.REF.3">1-3</a>). Like other proteases, legumain is synthesized as an inactive zymogen and is activated under acidic conditions in an autocatalytic process (<a class="bk_pop" href="#LP-1.REF.4" data-bk-pop-others="LP-1.REF.5">4, 5</a>). Legumain is expressed in diverse cell types and plays a key role in MHC class II–mediated antigen presentation, matrix degradation, and cysteine cathepsin processing (<a class="bk_pop" href="#LP-1.REF.6" data-bk-pop-others="LP-1.REF.7">6, 7</a>). Legumain has also been shown to be implicated in various pathological conditions including parasite infection, atherosclerosis, and tumorigenesis (<a class="bk_pop" href="#LP-1.REF.1" data-bk-pop-others="LP-1.REF.8 LP-1.REF.9 LP-1.REF.10">1, 8-10</a>). In mouse models of cancer, knockdown of legumain expression results in a marked decrease in tumor growth and metastasis, while overexpression of legumain leads to increased tumor migration, invasion, and metastasis (<a class="bk_pop" href="#LP-1.REF.1" data-bk-pop-others="LP-1.REF.11">1, 11</a>). In human tumors such as carcinomas of the breast, colon, and prostate, legumain has been shown to be overexpressed, while in normal organs like the kidney, liver, and spleen, only a limited quantity of legumain is detectable (<a class="bk_pop" href="#LP-1.REF.10" data-bk-pop-others="LP-1.REF.11">10, 11</a>).</p><p>Activity-based probes (ABPs) provide a highly versatile means to monitor <i>in vivo</i> protease function and regulation. ABPs utilize irreversible inhibitors that can covalently modify the active site of a protease in an activity-dependent fashion (<a class="bk_pop" href="#LP-1.REF.3" data-bk-pop-others="LP-1.REF.12 LP-1.REF.13">3, 12, 13</a>). To date, most ABPs have been designed to target cysteine cathepsins and caspases, and only a few legumain-specific probes have been reported in the literature. A typical legumain-specific probe consists of a peptide scaffold, a reactive functional group, and a reporter (<a class="bk_pop" href="#LP-1.REF.1" data-bk-pop-others="LP-1.REF.14 LP-1.REF.15 LP-1.REF.16 LP-1.REF.17 LP-1.REF.18">1, 14-18</a>). The Cbz-Ala-Ala-Asn peptide is commonly applied as a scaffold, which is designed on the basis of the sequence of a known substrate of legumain. Reactive functional groups, such as aza-Asn halomethylketones, aza-Asn epoxides, and aza-Asn Michael acceptors, have been used to make irreversible legumain binding. <i>In vitro</i> studies have shown that these probes have a high potency against legumain, but they also cross-react with cathepsins and caspases. The <i>in vivo</i> potency and specificity of these probes are largely unknown.</p><p>Investigators at Stanford University developed a class of aza-Asn epoxide ABPs with fast kinetic properties and increased selectivity for legumain for use in <i>in vivo</i> imaging studies (<a class="bk_pop" href="#LP-1.REF.1" data-bk-pop-others="LP-1.REF.3 LP-1.REF.16 LP-1.REF.19">1, 3, 16, 19</a>). Some of the probes were also tagged with a series of cell-permeabilizing carriers. These legumain-specific probes showed a high potential for use in imaging active legumain both in normal tissues and solid tumors. In this chapter, legumain probe-1 (LP-1), a Cy5-labeled aza-Pro-Asn epoxide probe, is introduced (<a class="bk_pop" href="#LP-1.REF.1">1</a>).</p><div id="LP-1.Related_Resource_Links"><h3>Related Resource Links:</h3><p>1) <a href="/gene/?term=legumain" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Gene information of legumain</a></p><p> 2) <a href="/omim/?term=legumain" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Legumain-related resource in OMIM</a></p></div></div><div id="LP-1.Synthesis"><h2 id="_LP-1_Synthesis_">Synthesis</h2><p>[<a href="/pubmed/?term=Blum+G" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>For comparative analysis, a group of probes have been synthesized and described in detail in several reports (<a class="bk_pop" href="#LP-1.REF.1" data-bk-pop-others="LP-1.REF.3 LP-1.REF.7 LP-1.REF.16 LP-1.REF.19">1, 3, 7, 16, 19</a>). These probes included LP-1, LP-1 ctrl, legumain probe-0 (LP-0), legumain inhibitor-1 (LI-1), legumain inhibitor-0 (LI-0), tLP-1, r8 LP-1, penetratin LP-1, and cholesterol LP-1. LP-1 ctrl was the control version of LP-1, which lacks the reactive epoxide group and does not covalently bind to legumain. LP-0 was the Cy5-labeled version of the probe Biotin-PD-AOMK which was developed previously in the same laboratory (<a class="bk_pop" href="#LP-1.REF.18">18</a>). LI-1 and LI-0 were the acetyl-capped versions of LP-1 and LP-0, respectively. Therefore, LP-1 and LI-1 were aza-epoxide inhibitors, whereas LP-0 and LI-0 were acyloxymethyl ketone (AOMK) inhibitors. The probes of tLP-1, r8 LP-1, penetratin LP-1, and cholesterol LP-1, were the enhanced versions of LP-1, which were generated by conjugating LP-1 with cell-penetrating carriers of tat peptides, cell-penetrating peptides (octa-arginine (r8) and penetratin), and cholesterol, respectively (<a class="bk_pop" href="#LP-1.REF.1">1</a>). All final products were >97% pure and characterized by either high-resolution mass spectrometry or matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The amounts of impurities were estimated to be minimal (3-7%) (<a class="bk_pop" href="#LP-1.REF.1">1</a>).</p></div><div id="LP-1.In_Vitro_Studies_Testing_in_Cells_a"><h2 id="_LP-1_In_Vitro_Studies_Testing_in_Cells_a_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed/?term=Blum+G" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Lee and Bogyo evaluated the potency and selectivity of LI-1 (as a representative of aza-epoxide inhibitors) and LI-0 (as a representative of AOMK inhibitors) against recombinant legumain, cathepsins B and L, and caspase-3 (<a class="bk_pop" href="#LP-1.REF.1">1</a>). Inhibition studies on the half-maximal inhibitory concentration (IC<sub>50</sub>) showed that LI-1 (IC<sub>50</sub> = 11.5 nmol) was 70-fold more potent than LI-0 (IC<sub>50</sub> = 704 nmol) against legumain, whereas both exhibited very weak activity against cathepsin B (IC<sub>50</sub> = 390 μmol for LI-1 and >1 mmol for LI-0) and cathepsin L (IC<sub>50</sub> = 220 μmol for LI-1 and >1 mmol for LI-0). LI-0 demonstrated a significant inhibitory effect (IC<sub>50</sub> = 2.8 μmol) on caspase-3, whereas LI-1 showed nearly no inhibition (IC<sub>50</sub> = 890 μmol). LI-1 inhibited legumain ~50-fold faster than LI-0 did. These results suggested that incorporation of P1 Asn <i>via</i> an aza-peptidyl scaffold greatly enhanced the efficiency and specificity of aza-epoxide scaffolds compared with that of the P1 Asp AOMK scaffolds. The rapid inhibition kinetics of the aza-Asn epoxide scaffolds may be advantageous for <i>in vivo</i> imaging.</p><p>Lee and Bogyo then verified the labeling of active legumain with LP-1 and LP-0 probes in intact NIH-3T3 and RAW 264.7 cells (<a class="bk_pop" href="#LP-1.REF.1">1</a>). After incubation of the cells with LP-1 and LP-0, SDS-PAGE gel analysis of the cell extracts showed that both probes selectively labeled the active legumain in NIH-3T3 fibroblasts. LP-1 labeled active legumain more efficiently than LP-0, showing an overall stronger labeling signal. However, both probes had some degree of cross-reactivity toward lysosomal cathepsins in RAW 264.7 macrophages. These data suggested that even though probes may have very low potency toward a particular protease target <i>in vitro</i>, when added to cells that actively accumulate the probes in their lysosomes, such as macrophages, they are able to react with other abundant proteases. Furthermore, when RAW 264.7 cells were pretreated with legumain inhibitors, more intense cathepsin labeling was observed. The investigators explained this finding by the fact that cathepsins are substrates of legumain and legumain inhibition could result in increased levels of cathepsins and, therefore, increased nonspecific labeling by the legumain probes.</p><p>On the basis of these results, LP-1 was selected for <i>in vivo</i> imaging studies because it has faster kinetics and overall higher potency, resulting in less background labeling of cathepsins and caspases.</p></div><div id="LP-1.Animal_Studies"><h2 id="_LP-1_Animal_Studies_">Animal Studies</h2><div id="LP-1.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22%20SUBSTANCENAME%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>The feasibility of LP-1 for <i>in vivo</i> imaging of active legumain has been tested with the C2C12/Hras1 tumor xenograft model (<a class="bk_pop" href="#LP-1.REF.1">1</a>). After injection of the LP-1 <i>via</i> tail vein of mice (<i>n</i> = 3), LP-1 rapidly accumulated in tumor tissues, whereas the control probe LP-1 ctrl did not show such accumulation (<i>n</i> = 2 mice). The control probe LP-1 ctrl lacks the reactive epoxide group and therefore does not covalently bind to legumain. The maximum signal/background ratio for LP-1 was reached at ~90 min after injection. The specific legumain signal declined over time but remained significantly higher than the signal observed for LP-1 ctrl, even at the later time points. These data suggested that LP-1 has fast binding and clearance properties. <i>Ex vivo</i> imaging of the tumors and SDS-PAGE analysis of the tumor extracts at the end of the imaging time course confirmed the <i>in vivo</i> selective labeling of legumain by LP-1. The levels of active legumain by imaging directly correlated with the intensity of legumain labeling by SDS-PAGE analysis, which suggests that LP-1 is selective toward legumain <i>in vivo</i> and has virtually no off-target labeling.</p><p>Lee and Bogyo further comparatively analyzed LP-1 and the corresponding versions with cell-penetrating carriers (<a class="bk_pop" href="#LP-1.REF.1">1</a>). In cultured cells, all the carrier-conjugates showed increased cellular uptake and resulted in stronger labeling, but also showed more cross-reactivity with other proteases compared with LP-1. In animal models, enhanced cellular delivery of the conjugates adversely affected their overall circulation, and caused increased association with tissues other than the target tumors, resulting in less useful imaging reagents. These results indicated that legumain ABPs are more effective as free probes that do not contain a carrier peptide.</p><p>Lee and Bogyo concluded that they developed a highly potent and selective probe, LP-1, toward active legumain. The favorable reactivity and clearance of LP-1 could result in a high contrast in tumors soon after probe injection. This probe can be used for noninvasive imaging studies of active legumain in whole tissues or cells (<a class="bk_pop" href="#LP-1.REF.1">1</a>).</p></div><div id="LP-1.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22%20SUBSTANCENAME%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="LP-1.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_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="LP-1.Human_Studies"><h2 id="_LP-1_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="LP-1.References"><h2 id="_LP-1_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="LP-1.REF.1">Lee J., Bogyo M.
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<em>Development of near-infrared fluorophore (NIRF)-labeled activity-based probes for in vivo imaging of legumain.</em>
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||
<span><span class="ref-journal">ACS Chem Biol. </span>2010;<span class="ref-vol">5</span>(2):233–43.</span> [<a href="/pmc/articles/PMC3222276/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3222276</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20017516" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20017516</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="LP-1.REF.2">Berdowska I.
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<em>Cysteine proteases as disease markers.</em>
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||
<span><span class="ref-journal">Clin Chim Acta. </span>2004;<span class="ref-vol">342</span>(1-2):41–69.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15026265" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15026265</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="LP-1.REF.3">Bogyo, M., A. Baruch, D.A. Jeffery, D. Greenbaum, A. Borodovsky, H. Ovaa, and B. Kessler, <em>Applications for chemical probes of proteolytic activity.</em> Curr Protoc Protein Sci, 2004<strong>Chapter 21</strong>: p. Unit 21 17. [<a href="https://pubmed.ncbi.nlm.nih.gov/18429259" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18429259</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="LP-1.REF.4">Mikolajczyk J., Boatright K.M., Stennicke H.R., Nazif T., Potempa J., Bogyo M., Salvesen G.S.
|
||
<em>Sequential autolytic processing activates the zymogen of Arg-gingipain.</em>
|
||
<span><span class="ref-journal">J Biol Chem. </span>2003;<span class="ref-vol">278</span>(12):10458–64.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12533545" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12533545</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="LP-1.REF.5">Ishizaki, T., A. Erickson, E. Kuric, M. Shamloo, I. Hara-Nishimura, A.R. Inacio, T. Wieloch, and K. Ruscher, <em>The asparaginyl endopeptidase legumain after experimental stroke.</em> J Cereb Blood Flow Metab, 2010. [<a href="/pmc/articles/PMC3023405/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3023405</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20234379" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20234379</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="LP-1.REF.6">Colbert J.D., Matthews S.P., Miller G., Watts C.
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<em>Diverse regulatory roles for lysosomal proteases in the immune response.</em>
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||
<span><span class="ref-journal">Eur J Immunol. </span>2009;<span class="ref-vol">39</span>(11):2955–65.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19637232" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19637232</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="LP-1.REF.7">Fonovic M., Bogyo M.
|
||
<em>Activity based probes for proteases: applications to biomarker discovery, molecular imaging and drug screening.</em>
|
||
<span><span class="ref-journal">Curr Pharm Des. </span>2007;<span class="ref-vol">13</span>(3):253–61.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17313359" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17313359</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="LP-1.REF.8">Affara N.I., Andreu P., Coussens L.M.
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||
<em>Delineating protease functions during cancer development.</em>
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||
<span><span class="ref-journal">Methods Mol Biol. </span>2009;<span class="ref-vol">539</span>:1–32.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19377975" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19377975</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="LP-1.REF.9">Blum G.
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||
<em>Use of fluorescent imaging to investigate pathological protease activity.</em>
|
||
<span><span class="ref-journal">Curr Opin Drug Discov Devel. </span>2008;<span class="ref-vol">11</span>(5):708–16.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18729022" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18729022</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="LP-1.REF.10">Gawenda J., Traub F., Luck H.J., Kreipe H., von Wasielewski R.
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||
<em>Legumain expression as a prognostic factor in breast cancer patients.</em>
|
||
<span><span class="ref-journal">Breast Cancer Res Treat. </span>2007;<span class="ref-vol">102</span>(1):1–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17028987" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17028987</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="LP-1.REF.11">Luo Y., Zhou H., Krueger J., Kaplan C., Lee S.H., Dolman C., Markowitz D., Wu W., Liu C., Reisfeld R.A., Xiang R.
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||
<em>Targeting tumor-associated macrophages as a novel strategy against breast cancer.</em>
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||
<span><span class="ref-journal">J Clin Invest. </span>2006;<span class="ref-vol">116</span>(8):2132–2141.</span> [<a href="/pmc/articles/PMC1513049/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1513049</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/16862213" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16862213</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="LP-1.REF.12">Blum G., von Degenfeld G., Merchant M.J., Blau H.M., Bogyo M.
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<em>Noninvasive optical imaging of cysteine protease activity using fluorescently quenched activity-based probes.</em>
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<span><span class="ref-journal">Nat Chem Biol. </span>2007;<span class="ref-vol">3</span>(10):668–77.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17828252" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17828252</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="LP-1.REF.13">Hang H.C., Loureiro J., Spooner E., van der Velden A.W., Kim Y.M., Pollington A.M., Maehr R., Starnbach M.N., Ploegh H.L.
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<em>Mechanism-based probe for the analysis of cathepsin cysteine proteases in living cells.</em>
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<span><span class="ref-journal">ACS Chem Biol. </span>2006;<span class="ref-vol">1</span>(11):713–23.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17184136" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17184136</span></a>]</div></dd><dt>14.</dt><dd><div class="bk_ref" id="LP-1.REF.14">Asgian J.L., James K.E., Li Z.Z., Carter W., Barrett A.J., Mikolajczyk J., Salvesen G.S., Powers J.C.
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||
<em>Aza-peptide epoxides: a new class of inhibitors selective for clan CD cysteine proteases.</em>
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||
<span><span class="ref-journal">J Med Chem. </span>2002;<span class="ref-vol">45</span>(23):4958–60.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12408706" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12408706</span></a>]</div></dd><dt>15.</dt><dd><div class="bk_ref" id="LP-1.REF.15">James K.E., Gotz M.G., Caffrey C.R., Hansell E., Carter W., Barrett A.J., McKerrow J.H., Powers J.C.
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<em>Aza-peptide epoxides: potent and selective inhibitors of Schistosoma mansoni and pig kidney legumains (asparaginyl endopeptidases).</em>
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<span><span class="ref-journal">Biol Chem. </span>2003;<span class="ref-vol">384</span>(12):1613–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14719804" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14719804</span></a>]</div></dd><dt>16.</dt><dd><div class="bk_ref" id="LP-1.REF.16">Kato D., Boatright K.M., Berger A.B., Nazif T., Blum G., Ryan C., Chehade K.A., Salvesen G.S., Bogyo M.
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<em>Activity-based probes that target diverse cysteine protease families.</em>
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||
<span><span class="ref-journal">Nat Chem Biol. </span>2005;<span class="ref-vol">1</span>(1):33–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16407991" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16407991</span></a>]</div></dd><dt>17.</dt><dd><div class="bk_ref" id="LP-1.REF.17">Sexton K.B., Kato D., Berger A.B., Fonovic M., Verhelst S.H., Bogyo M.
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<em>Specificity of aza-peptide electrophile activity-based probes of caspases.</em>
|
||
<span><span class="ref-journal">Cell Death Differ. </span>2007;<span class="ref-vol">14</span>(4):727–32.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17170749" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17170749</span></a>]</div></dd><dt>18.</dt><dd><div class="bk_ref" id="LP-1.REF.18">Sexton K.B., Witte M.D., Blum G., Bogyo M.
|
||
<em>Design of cell-permeable, fluorescent activity-based probes for the lysosomal cysteine protease asparaginyl endopeptidase (AEP)/legumain.</em>
|
||
<span><span class="ref-journal">Bioorg Med Chem Lett. </span>2007;<span class="ref-vol">17</span>(3):649–53.</span> [<a href="/pmc/articles/PMC1832115/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1832115</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17189693" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17189693</span></a>]</div></dd><dt>19.</dt><dd><div class="bk_ref" id="LP-1.REF.19">Kato D., Verhelst S.H., Sexton K.B., Bogyo M.
|
||
<em>A general solid phase method for the preparation of diverse azapeptide probes directed against cysteine proteases.</em>
|
||
<span><span class="ref-journal">Org Lett. </span>2005;<span class="ref-vol">7</span>(25):5649–52.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16321013" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16321013</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: NBK44812</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20642010" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20642010</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/AB50_Cy5/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/CyRAFTRGD/" title="Next page in this title">Next ></a></div></div></div></div>
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<div id="ncbi_share_book"><a href="#" class="ncbi_share" data-ncbi_share_config="popup:false,shorten:true" ref="id=NBK44812&db=books">Share</a></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/NBK44812/?report=reader">PubReader</a></li><li><a href="/books/NBK44812/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK44812" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK44812" style="display:none" title="Cite this Page"><div class="bk_tt">Shan L. Cy5-labeled aza-peptidyl Pro-Asn epoxide. 2010 May 12 [Updated 2010 Jun 3]. 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/NBK44812/pdf/Bookshelf_NBK44812.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="#LP-1.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#LP-1.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#LP-1.In_Vitro_Studies_Testing_in_Cells_a" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#LP-1.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#LP-1.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#LP-1.References" ref="log$=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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/><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=2194600" ref="log$=recordlinks">PMC</a><div class="brieflinkpop offscreen_noflow">PubMed Central citations</div></li><li class="brieflinkpopper"><a class="brieflinkpopperctrl" 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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Lee J, Bogyo M. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Bioorg Med Chem Lett. 2012 Feb 1; 22(3):1340-3. Epub 2011 Dec 21.</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/17170749" ref="ordinalpos=1&linkpos=5&log$=relatedarticles&logdbfrom=pubmed">Specificity of aza-peptide electrophile activity-based probes of caspases.</a><span class="source">[Cell Death Differ. 2007]</span><div class="brieflinkpop offscreen_noflow">Specificity of aza-peptide electrophile activity-based probes of caspases.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Sexton KB, Kato D, Berger AB, Fonovic M, Verhelst SH, Bogyo M. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Cell Death Differ. 2007 Apr; 14(4):727-32. 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</div>
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<div class="row">
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<div class="col-lg-12 centered-lg">
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<nav class="bottom-links">
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<ul class="mt-3">
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<li>
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<a class="text-white" href="//www.nlm.nih.gov/">NLM</a>
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</li>
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<li>
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<a class="text-white" href="https://www.nih.gov/">NIH</a>
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</li>
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<li>
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<a class="text-white" href="https://www.hhs.gov/">HHS</a>
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</li>
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<li>
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<a class="text-white" href="https://www.usa.gov/">USA.gov</a>
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</li>
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</ul>
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</nav>
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</div>
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</div>
|
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</section>
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<script type="text/javascript" src="/portal/portal3rc.fcgi/rlib/js/InstrumentOmnitureBaseJS/InstrumentNCBIConfigJS/InstrumentNCBIBaseJS/InstrumentPageStarterJS.js?v=1"> </script>
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<script type="text/javascript" src="/portal/portal3rc.fcgi/static/js/hfjs2.js"> </script>
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<!--/.page-->
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</div><!-- /.twelve_col -->
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<span class="PAFAppResources"></span>
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<!-- BESelector tab -->
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||
<noscript><img alt="statistics" src="/stat?jsdisabled=true&ncbi_db=books&ncbi_pdid=book-part&ncbi_acc=NBK44812&ncbi_domain=micad&ncbi_report=record&ncbi_type=fulltext&ncbi_objectid=&ncbi_pcid=/NBK44812/&ncbi_pagename=Cy5-labeled aza-peptidyl Pro-Asn epoxide - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf&ncbi_bookparttype=chapter&ncbi_app=bookshelf" /></noscript>
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<script type="text/javascript" src="//static.pubmed.gov/portal/portal3rc.fcgi/4216699/js/3879255/4121861/3501987/4008961/3893018/3821238/4062932/4209313/4212053/4076480/3921943/3400083/3426610.js" snapshot="books"></script></body>
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