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<title>Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3) - 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="Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3)" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2008/07/21" /><meta name="citation_author" content="Huiming Zhang" /><meta name="citation_pmid" content="20641665" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK23466/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3)" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Huiming Zhang" /><meta name="DC.Date" content="2008/07/21" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK23466/" /><meta name="description" content="Photodynamic therapy (PDT), also known as photochemotherapy, uses light-activated photosensitizers (PS) in the presence of oxygen to kill cells (1). PDT has become a promising modality to treat skin, esophagus, and lung cancers, as well as other diseases such as atherosclerosis, macular degeneration, and rheumatoid arthritis (2). In PDT, light excites the singlet state of the PS, followed by intersystem transition from the singlet state to the triplet state; then, the energy is transferred from the triplet state of the PS to the triplet ground state of oxygen 3O2(X3Σg-) (3O2 triplet state quenching) to generate singlet oxygen 1O2(a1Δg) (3). The produced 1O2 is a major cytotoxic agent that has a short life time (<200 ns) and an average diffusion range (~20 nm, which is smaller than the diameter of a cell) (2). Such a short diffusion range requires the delivery of target-specific PS agents into subcellular compartments such as cytoskeletal tubulin, lysosomes, mitochondria, plasma membrane, and the nucleus, where they can generate 1O2 efficiently (2). A novel type of PS agents, called a photodynamic molecular beacon (PMB) or killer beacon, has been developed to meet this requirement (2, 4). A typical PMB consists of four modular components: a fluorescent PS, a quencher, a linker, and a delivery vehicle. The target-specific linkers keep the fluorescent PS and the quencher within the effective distance of the Föster radius (3–6 nm) (2), which allows efficient fluorescence resonance energy transfer between the fluorescent PS and the quencher. As a result, the fluorescent PS is silent until the PMB meets the target, where the enzyme cleaves the linker and activates the fluorescence of the PS (4). Thus, the PS performs two functions by producing 1O2 to kill cells and by illuminating detectable fluorescence to image its own therapeutic outcome (5)." /><meta name="og:title" content="Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3)" /><meta name="og:type" content="book" /><meta name="og:description" content="Photodynamic therapy (PDT), also known as photochemotherapy, uses light-activated photosensitizers (PS) in the presence of oxygen to kill cells (1). PDT has become a promising modality to treat skin, esophagus, and lung cancers, as well as other diseases such as atherosclerosis, macular degeneration, and rheumatoid arthritis (2). In PDT, light excites the singlet state of the PS, followed by intersystem transition from the singlet state to the triplet state; then, the energy is transferred from the triplet state of the PS to the triplet ground state of oxygen 3O2(X3Σg-) (3O2 triplet state quenching) to generate singlet oxygen 1O2(a1Δg) (3). The produced 1O2 is a major cytotoxic agent that has a short life time (<200 ns) and an average diffusion range (~20 nm, which is smaller than the diameter of a cell) (2). Such a short diffusion range requires the delivery of target-specific PS agents into subcellular compartments such as cytoskeletal tubulin, lysosomes, mitochondria, plasma membrane, and the nucleus, where they can generate 1O2 efficiently (2). A novel type of PS agents, called a photodynamic molecular beacon (PMB) or killer beacon, has been developed to meet this requirement (2, 4). A typical PMB consists of four modular components: a fluorescent PS, a quencher, a linker, and a delivery vehicle. The target-specific linkers keep the fluorescent PS and the quencher within the effective distance of the Föster radius (3–6 nm) (2), which allows efficient fluorescence resonance energy transfer between the fluorescent PS and the quencher. As a result, the fluorescent PS is silent until the PMB meets the target, where the enzyme cleaves the linker and activates the fluorescence of the PS (4). Thus, the PS performs two functions by producing 1O2 to kill cells and by illuminating detectable fluorescence to image its own therapeutic outcome (5)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK23466/" /><meta name="og:site_name" content="NCBI Bookshelf" /><meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" /><meta name="twitter:card" content="summary" /><meta name="twitter:site" content="@ncbibooks" /><meta name="bk-non-canon-loc" content="/books/n/micad/PPB/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK23466/" /><link rel="stylesheet" href="/corehtml/pmc/css/figpopup.css" type="text/css" media="screen" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_print.min.css" type="text/css" media="print" /><style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} .body-content h2, .body-content .h2 {border-bottom: 1px solid #97B0C8} .body-content h2.inline {border-bottom: none} a.page-toc-label , .jig-ncbismoothscroll a {text-decoration:none;border:0 !important} .temp-labeled-list .graphic {display:inline-block !important} .temp-labeled-list img{width:100%}</style><script type="text/javascript" src="/corehtml/pmc/js/jquery.hoverIntent.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/common.min.js?_=3.18"> </script><script type="text/javascript" src="/corehtml/pmc/js/large-obj-scrollbars.min.js"> </script><script type="text/javascript">window.name="mainwindow";</script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/book-toc.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/books.min.js"> </script><meta name="book-collection" content="NONE" />
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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="#__NBK23466_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23466_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/sospyropheophorbidepyro/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/PMB/" 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="_NBK23466_"><span class="title" itemprop="name">Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3) </span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">PPB</div><p class="contrib-group"><span itemprop="author">Huiming Zhang</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23466_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23466_ai__"><div class="contrib half_rhythm"><span itemprop="author">Huiming Zhang</span>, PhD<div class="affiliation small">
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National Center for Biotechnology Information, NLM, NIH, Bethesda, MD,
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<span class="before-email-separator"></span><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>
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</div></div></div><p class="small">Created: <span itemprop="datePublished">May 22, 2008</span>; Last Update: <span itemprop="dateModified">July 21, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="PPB.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23466/table/PPB.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__PPB.T1_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3)</td><td rowspan="9" 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>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">PPB</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;">Peptide</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;">Caspase-3</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, near-infrared (NIR) fluorescence</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;">Pyropheophorbide α (Pyro)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Yes</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li></ul>
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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" /> 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 currently available 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="PPB.Background"><h2 id="_PPB_Background_">Background</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=PPB" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Photodynamic therapy (PDT), also known as photochemotherapy, uses light-activated photosensitizers (PS) in the presence of oxygen to kill cells (<a class="bk_pop" href="#PPB.REF.1">1</a>). PDT has become a promising modality to treat skin, esophagus, and lung cancers, as well as other diseases such as atherosclerosis, macular degeneration, and rheumatoid arthritis (<a class="bk_pop" href="#PPB.REF.2">2</a>). In PDT, light excites the singlet state of the PS, followed by intersystem transition from the singlet state to the triplet state; then, the energy is transferred from the triplet state of the PS to the triplet ground state of oxygen <sup>3</sup>O<sub>2</sub>(X<sup>3</sup>Σ<sub>g</sub><sup>-</sup>) (<sup>3</sup>O<sub>2</sub> triplet state quenching) to generate singlet oxygen <sup>1</sup>O<sub>2</sub>(a<sup>1</sup>Δ<sub>g</sub>) (<a class="bk_pop" href="#PPB.REF.3">3</a>). The produced <sup>1</sup>O<sub>2</sub> is a major cytotoxic agent that has a short life time (<200 ns) and an average diffusion range (~20 nm, which is smaller than the diameter of a cell) (<a class="bk_pop" href="#PPB.REF.2">2</a>). Such a short diffusion range requires the delivery of target-specific PS agents into subcellular compartments such as cytoskeletal tubulin, lysosomes, mitochondria, plasma membrane, and the nucleus, where they can generate <sup>1</sup>O<sub>2</sub> efficiently (<a class="bk_pop" href="#PPB.REF.2">2</a>). A novel type of PS agents, called a photodynamic molecular beacon (PMB) or killer beacon, has been developed to meet this requirement (<a class="bk_pop" href="#PPB.REF.2">2</a>, <a class="bk_pop" href="#PPB.REF.4">4</a>). A typical PMB consists of four modular components: a fluorescent PS, a quencher, a linker, and a delivery vehicle. The target-specific linkers keep the fluorescent PS and the quencher within the effective distance of the Föster radius (3–6 nm) (<a class="bk_pop" href="#PPB.REF.2">2</a>), which allows efficient fluorescence resonance energy transfer between the fluorescent PS and the quencher. As a result, the fluorescent PS is silent until the PMB meets the target, where the enzyme cleaves the linker and activates the fluorescence of the PS (<a class="bk_pop" href="#PPB.REF.4">4</a>). Thus, the PS performs two functions by producing <sup>1</sup>O<sub>2</sub> to kill cells and by illuminating detectable fluorescence to image its own therapeutic outcome (<a class="bk_pop" href="#PPB.REF.5">5</a>).</p><p>Caspases are cysteine aspartate proteinases (<a class="bk_pop" href="#PPB.REF.6">6</a>), and they participate in apoptosis through direct disassembly of cell structure, cleavage of several important proteins (gelsolin, focal adhesion kinase, and p21), shutting down DNA replication and repair, disrupting nuclear structure, and disintegrating cells into apoptotic bodies (<a class="bk_pop" href="#PPB.REF.7">7</a>). As a main downstream effector, the caspase subtype-3 (capspase-3) recognizes targets that contain the tetrapeptide sequence Asp-Glu-Val-Asp (<a class="bk_pop" href="#PPB.REF.7">7</a>). Proteins with this recognition motif are cleaved specifically with high efficiency (<i>k</i><sub><i>cat</i></sub><i>/K</i><sub><i>m</i></sub> > 10<sup>6</sup> M<sup>-1</sup>s<sup>-1</sup>). Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3) (PPB) is a PMB specific for caspase-3, and it is detectable with near-infrared (NIR) fluorescence imaging (<a class="bk_pop" href="#PPB.REF.5">5</a>). PPB consists of the infrared fluorescence PS pyropheophorbide α (Pyro), a black hole quencher 3 (BHQ3), and a peptide linker (GDEVDGSGK) (<a class="bk_pop" href="#PPB.REF.5">5</a>). The peptide contains the tetrapeptide motif DEVD for caspase-3 recognition, and the cleavage site is located between the D and G residues. Pyro acts as the intracellular vehicle and as the PS (absorption, 665 nm; emission, 675 nm and 720 nm) with good <sup>1</sup>O<sub>2</sub> production (50%). Pyro lacks dark toxicity (toxicity in absence of ligh) because of its low absorption between 450–600 nm. BHQ3 (absorption, 672 nm) can efficiently quench Pyro fluorescence <i>via</i> fluorescence resonance energy transfer (FRET). The cleavage of PPB by caspase-3 separates the photosensitizer (Pyro) from the quencher (BHQ3) and restores the Pyro fluorescence for detection.</p></div><div id="PPB.Synthesis"><h2 id="_PPB_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(%20PPB)+AND+synthesis%0D%0A" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Stefflova et al. reported the detailed synthesis of PPB (<a class="bk_pop" href="#PPB.REF.5">5</a>). A peptide of Fmoc-GD(Boc)E(Boc)VD(Boc)GS(Boc)GK(Mtt)-Sieber resin (Boc is t-butoxycarbonyl; Mtt is methyltrityl) was synthesized by the manual, Fmoc, solid-phase, peptide synthesis protocol with commercially available N-α-protected amino acids as building blocks, Sieber amide resin as a solid support, and N-hydroxybenzotriazole (HOBt)/2-(benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) as amino acid activators. After the last Fmoc group cleavage, Pyro-acid was coupled to the α-NH<sub>2</sub> group of N-terminal glycine of the peptide-resin at a molar ratio of 3:1. The produced peptide resin was treated with 50% trifluoroacetic acid and 5% triisopropylsilane in dichloromethane to yield Pyro-GDEVDGSGK, followed by coupling of the ε-NH<sub>2</sub> of the C-terminal lysine with BHQ3-NHS to yield PPB. The product was purified with high-performance liquid chromatography and the structure was characterized by UV-vis spectroscopy and matrix-assisted laser desorption/ionization (MALDI)-time of flight mass spectrometry (TOF).</p></div><div id="PPB.In_Vitro_Studies_Tes"><h2 id="_PPB_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(%20PPB)+AND+%22in+vitro%22" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The specificity of PPB to caspapse-3 was tested in aqueous solution (<a class="bk_pop" href="#PPB.REF.5">5</a>). High-performance liquid chromatography was used to examine the cleavage product. PPB (6.3 μM) was cleaved to two pieces after incubation for 50 min with caspase-3 (0.2 μg). An immediate increase of fluorescence was observed, which reached a plateau at 90 min with as much as an 8-fold increase. This increase was not observed for PPB alone, for the presence of PPB (6.3 μM) with caspase-3 inhibitor (Ac-DEVD-CHO, 100 μM), or the presence of scrambled PPB (Pyro-GPLGLAREK-(BHQ3) with caspase-3 (molar ratio of 200:1). Cleavage was prohibited in the presence of caspase-3–specific inhibitor or scrambled PPB, confirming that PPB was specifically cleaved by caspase-3 in solution.</p><p>Stefflova et al. used PPB to study capspase-3–triggered PDT in tumor cells <i>in vitro</i> (<a class="bk_pop" href="#PPB.REF.5">5</a>). Hepatoblastoma G<sub>2</sub> cells (HepG<sub>2</sub>) were incubated with 200 μM PPB for 30 min or 24 h and subsequently treated with a light dose of 5 J/cm<sup>2</sup> at 670 nm. The cleavage of PPB in the cells was monitored with confocal microscopy. The PDT-treated cells exhibited a significant increase of fluorescence intensity. In comparisons, a minimal fluorescence increase was observed for the control cells that were incubated with PPB for 24 h but not exposed to the light, and the cells that were incubated with the scrambled sequence Pyro-GHSSK(BHQ3)LQL followed by exposure to light. These results demonstrate that the peptide linker in the PPB was cleaved within the PDT-treated cells, which induced significant increases in the Pyro fluorescence. To further confirm that this cleavage is apoptosis-related, Apoptag, a terminal <a href="http://en.wikipedia.org/wiki/Nucleotide" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri"><u>deoxynucleotidyl</u></a> transferase–mediated dUTP nick end labeling (TUNEL) assay, was used to examine apoptosis-related DNA cleavage in the HepG<sub>2</sub> cells that were incubated with PPB and treated with PDT. The fluorescence from Pyro (633 nm) as a result of the caspase-3–dependent cleavage of PPB and the fluorescence from fluorescein (488 nm) as a result of Apoptag stain were found in the same cellular compartment, which confirmed that apoptosis induced PPB cleavage <i>in vitro</i>.</p></div><div id="PPB.Animal_Studies"><h2 id="_PPB_Animal_Studies_">Animal Studies</h2><div id="PPB.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(%20PPB)%20+AND++rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Stefflova et al. studied the cleavage of PPB <i>in vivo</i> with fluorescent imaging (<a class="bk_pop" href="#PPB.REF.5">5</a>). Nude mice were subcutaneously inoculated on the upper side of the leg with 10<sup>7</sup> HepG<sub>2</sub> cells, and the tumor was grown for about 20 days. Immediately after subcutaneous injection of 80 nmol PPB into the tumor sites, one mouse received PDT treatment at a light dose of 150 J/cm<sup>2</sup> for the whole tumor area, and the images were collected at 2, 3, and 4 h. Compared with the tumor that was injected with PPB but not treated with PDT, a visible fluorescence increase was found in the tumor treated with PPB followed by PDT treatment.</p></div><div id="PPB.Other_NonPrimate_Mam"><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 publication is currently available.</p></div><div id="PPB.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(%20PPB)%20+AND+(primate+non+human)" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="PPB.Human_Studies"><h2 id="_PPB_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=(%20PPB)%20+AND+human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p><div id="PPB.NIH_Support"><h3>NIH Support</h3><p>CA 105008</p></div></div><div id="PPB.references"><h2 id="_PPB_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="PPB.REF.1">Dougherty T.J. , Gomer C.J. , Henderson B.W. , Jori G. , Kessel D. , Korbelik M. , Moan J. , Peng Q. Photodynamic therapy. <span><span class="ref-journal">J Natl Cancer Inst. </span>1998;<span class="ref-vol">
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<strong>90</strong>
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</span>(12):889–905.</span> [<a href="/pmc/articles/PMC4592754/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC4592754</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/9637138" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9637138</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="PPB.REF.2">Stefflova K. , Chen J. , Zheng G. Killer beacons for combined cancer imaging and therapy. <span><span class="ref-journal">Curr Med Chem. </span>2007;<span class="ref-vol">
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<strong>14</strong>
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</span>(20):2110–25.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17691951" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17691951</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="PPB.REF.3">Clo E. , Snyder J.W. , Voigt N.V. , Ogilby P.R. , Gothelf K.V. DNA-programmed control of photosensitized singlet oxygen production. <span><span class="ref-journal">J Am Chem Soc. </span>2006;<span class="ref-vol">
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<strong>128</strong>
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</span>(13):4200–1.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16568974" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16568974</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="PPB.REF.4">Zheng G. , Chen J. , Stefflova K. , Jarvi M. , Li H. , Wilson B.C. Photodynamic molecular beacon as an activatable photosensitizer based on protease-controlled singlet oxygen quenching and activation. <span><span class="ref-journal">Proc Natl Acad Sci U S A. </span>2007;<span class="ref-vol">
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<strong>104</strong>
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</span>(21):8989–94.</span> [<a href="/pmc/articles/PMC1868591/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC1868591</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/17502620" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17502620</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="PPB.REF.5">Stefflova K. , Chen J. , Marotta D. , Li H. , Zheng G. Photodynamic therapy agent with a built-in apoptosis sensor for evaluating its own therapeutic outcome in situ. <span><span class="ref-journal">J Med Chem. </span>2006;<span class="ref-vol">
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<strong>49</strong>
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</span>(13):3850–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16789741" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16789741</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="PPB.REF.6">Kumar S. , Richards-Kortum R. Optical molecular imaging agents for cancer diagnostics and therapeutics. <span><span class="ref-journal">Nanomed. </span>2006;<span class="ref-vol">
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<strong>1</strong>
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</span>(1):23–30.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17716206" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17716206</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="PPB.REF.7">Thornberry N.A. , Lazebnik Y. Caspases: enemies within. <span><span class="ref-journal">Science. </span>1998;<span class="ref-vol">
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<strong>281</strong>
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</span>(5381):1312–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9721091" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9721091</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: NBK23466</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641665" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641665</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/sospyropheophorbidepyro/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/PMB/" 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/NBK23466/?report=reader">PubReader</a></li><li><a href="/books/NBK23466/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23466" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23466" style="display:none" title="Cite this Page"><div class="bk_tt">Zhang H. Pyro-Gly-Asp-Glu-Val-Asp-Gly-Ser-Gly-Lys(BHQ3) 2008 May 22 [Updated 2008 Jul 21]. 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/NBK23466/pdf/Bookshelf_NBK23466.pdf">PDF version of this page</a> (131K)</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="#PPB.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#PPB.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#PPB.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#PPB.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#PPB.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#PPB.references" ref="log$=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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