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<meta name="ncbi_db" content="books" /><meta name="ncbi_pdid" content="book-part" /><meta name="ncbi_acc" content="NBK44814" /><meta name="ncbi_domain" content="micad" /><meta name="ncbi_report" content="record" /><meta name="ncbi_type" content="fulltext" /><meta name="ncbi_objectid" content="" /><meta name="ncbi_pcid" content="/NBK44814/" /><meta name="ncbi_pagename" content="186Re-Labeled [N-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V) - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf" /><meta name="ncbi_bookparttype" content="chapter" /><meta name="ncbi_app" content="bookshelf" />
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<title>186Re-Labeled [N-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V) - 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="186Re-Labeled [N-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V)" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2010/06/03" /><meta name="citation_author" content="Arvind Chopra" /><meta name="citation_pmid" content="20642012" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK44814/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="186Re-Labeled [N-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V)" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Arvind Chopra" /><meta name="DC.Date" content="2010/06/03" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK44814/" /><meta name="description" content="Bisphosphonates (BPs) or nitrogen-containing bisphosphonates (NBPs) are often used for the management of pain palliation and disorders related to skeletal tissue, including those arising from cancer metastases, because these compounds have a very high affinity for hydroxyapatite (HA), a component of the bone matrix. These phosphonates or their derivatives tend to accumulate in osteoclasts located at areas of increased bone metabolism by inhibiting the enzyme farnesyl diphosphate (or pyrophosphate) synthase, an important regulatory enzyme of the cellular mevalonate pathway, which is involved in protein prenylation (1). The molecular mechanism of action of BPs and the NBPs has been described by Drake et. al. (2). Several BPs and NBPs are commercially available for clinical use to treat different bone disorders, and there are ongoing clinical trials approved by the United States Food and Drug Administration to evaluate these compounds for the treatment of various bone ailments. In addition, BPs are often labeled with 99mTc or 186/188Re and used for the imaging and treatment of pain as a result of bone metastases from cancer such as that of the breast or the prostate (3). However, these compounds have limited efficacy primarily because they exist either as a mixture of anionic compounds with varying properties (e.g., 99mTc- labeled methyl diphosphonate (MDP)) or are unstable (e.g., 86Re-labeled 1-hydroxyethylidene-1,1-diphosphonate) under in vivo conditions, resulting in a reduced uptake at targeted bone areas and an increased accumulation in non-target soft tissue such as the gastric lining of the stomach (4). The limited clinical utility of radiolabeled BPs was suggested to be caused by the dual activities exhibited by the compounds: one phosphonate group acts as a radionuclide chelator, and the other phosphonate group binds to the target(s).Therefore, due to the close proximity of the two groups, one activity may be interfering with the other (4)." /><meta name="og:title" content="186Re-Labeled [N-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V)" /><meta name="og:type" content="book" /><meta name="og:description" content="Bisphosphonates (BPs) or nitrogen-containing bisphosphonates (NBPs) are often used for the management of pain palliation and disorders related to skeletal tissue, including those arising from cancer metastases, because these compounds have a very high affinity for hydroxyapatite (HA), a component of the bone matrix. These phosphonates or their derivatives tend to accumulate in osteoclasts located at areas of increased bone metabolism by inhibiting the enzyme farnesyl diphosphate (or pyrophosphate) synthase, an important regulatory enzyme of the cellular mevalonate pathway, which is involved in protein prenylation (1). The molecular mechanism of action of BPs and the NBPs has been described by Drake et. al. (2). Several BPs and NBPs are commercially available for clinical use to treat different bone disorders, and there are ongoing clinical trials approved by the United States Food and Drug Administration to evaluate these compounds for the treatment of various bone ailments. In addition, BPs are often labeled with 99mTc or 186/188Re and used for the imaging and treatment of pain as a result of bone metastases from cancer such as that of the breast or the prostate (3). However, these compounds have limited efficacy primarily because they exist either as a mixture of anionic compounds with varying properties (e.g., 99mTc- labeled methyl diphosphonate (MDP)) or are unstable (e.g., 86Re-labeled 1-hydroxyethylidene-1,1-diphosphonate) under in vivo conditions, resulting in a reduced uptake at targeted bone areas and an increased accumulation in non-target soft tissue such as the gastric lining of the stomach (4). The limited clinical utility of radiolabeled BPs was suggested to be caused by the dual activities exhibited by the compounds: one phosphonate group acts as a radionuclide chelator, and the other phosphonate group binds to the target(s).Therefore, due to the close proximity of the two groups, one activity may be interfering with the other (4)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK44814/" /><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/MAMABP186Re/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK44814/" /><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="#__NBK44814_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK44814_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/sos186re/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MAMAHBP186Re/" 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="_NBK44814_"><span class="title" itemprop="name"><sup>186</sup>Re-Labeled [<i>N</i>-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V)</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"> [<sup>186</sup>Re]MAMA-BP</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK44814_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK44814_ai__"><div class="contrib half_rhythm"><span itemprop="author">Arvind Chopra</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, NIH, Bethesda, MD 20894<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a></div></div></div></div><p class="small">Created: <span itemprop="datePublished">November 6, 2009</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="MAMABP186Re.T.nc_Chemical_name186ReLabel" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK44814/table/MAMABP186Re.T.nc_Chemical_name186ReLabel/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__MAMABP186Re.T.nc_Chemical_name186ReLabel_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>186</sup>Re-Labeled [<i>N</i>-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V)<br /></td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/85281220" 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=85281220" alt="image 85281220 in the ncbi pubchem database" /></a>
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</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>186</sup>Re]MAMA-BP<br /></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Synonym:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"></td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Compound</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Hydroxyapatite: Bone imaging<br />Molecular target: Farnesyl disphosphate (pyrophosphate) synthase</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;">Single-photon emission computed tomography (SPECT); gamma planar 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;"><sup>186</sup>Re</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure of [<sup>186</sup>Re]MAMA-BP 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="MAMABP186Re.Background"><h2 id="_MAMABP186Re_Background_">Background</h2><p>[<a href="/pubmed?term=dipycolylamine%20alendronate&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Bisphosphonates (BPs) or nitrogen-containing bisphosphonates (NBPs) are often used for the management of pain palliation and disorders related to skeletal tissue, including those arising from cancer metastases, because these compounds have a very high affinity for hydroxyapatite (HA), a component of the bone matrix. These phosphonates or their derivatives tend to accumulate in osteoclasts located at areas of increased bone metabolism by inhibiting the enzyme farnesyl diphosphate (or pyrophosphate) synthase, an important regulatory enzyme of the cellular mevalonate pathway, which is involved in protein prenylation (<a class="bk_pop" href="#MAMABP186Re.REF.1">1</a>). The molecular mechanism of action of BPs and the NBPs has been described by Drake et. al. (<a class="bk_pop" href="#MAMABP186Re.REF.2">2</a>). Several BPs and NBPs are commercially available for clinical use to treat different bone disorders, and there are ongoing <a href="http://clinicaltrials.gov/ct2/results?term=bisphosphonates" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">clinical trials</a> approved by the United States Food and Drug Administration to evaluate these compounds for the treatment of various bone ailments. In addition, BPs are often labeled with <sup>99m</sup>Tc or <sup>186/188</sup>Re and used for the imaging and treatment of pain as a result of bone metastases from cancer such as that of the breast or the prostate (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). However, these compounds have limited efficacy primarily because they exist either as a mixture of anionic compounds with varying properties (e.g., <sup>99m</sup>Tc- labeled methyl diphosphonate (MDP)) or are unstable (e.g., <sup>86</sup>Re-labeled 1-hydroxyethylidene-1,1-diphosphonate) under <i>in vivo</i> conditions, resulting in a reduced uptake at targeted bone areas and an increased accumulation in non-target soft tissue such as the gastric lining of the stomach (<a class="bk_pop" href="#MAMABP186Re.REF.4">4</a>). The limited clinical utility of radiolabeled BPs was suggested to be caused by the dual activities exhibited by the compounds: one phosphonate group acts as a radionuclide chelator, and the other phosphonate group binds to the target(s).Therefore, due to the close proximity of the two groups, one activity may be interfering with the other (<a class="bk_pop" href="#MAMABP186Re.REF.4">4</a>).</p><p>In an effort to solve the stability problems observed with the <sup>186</sup>Re-labeled NBPs, Ogawa et al. developed two new NBPs, <sup>186</sup>Re-[<i>N</i>-[2-[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V) ([<sup>186</sup>Re]MAMA-BP) and its hydroxylated derivative, <sup>186</sup>Re-[<i>N</i>-[2-[[4-[(4-hydroxy-4,4-diphosphonobutyl)amino]-4-oxobutyl]-2-thioethylamino]acetyl]-2-aminoethanethiolate] oxorhenium (V) ([<sup>186</sup>Re]MAMA-HBP) (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). The investigators then compared the two compounds for their affinity to HA under <i>in vitro</i> conditions and studied the biodistribution of the radiochemicals in normal mice. This chapter presents the results obtained with [<sup>186</sup>Re]MAMA-BP. Results obtained with [<sup>186</sup>Re]MAMA-HBP are presented in a separate chapter of MICAD (<a class="bk_pop" href="#MAMABP186Re.REF.5">5</a>).</p></div><div id="MAMABP186Re.Synthesis"><h2 id="_MAMABP186Re_Synthesis_">Synthesis</h2><p>[<a href="/pubmed?term=nitrogen%20containing%20bisphosphonate%20synthesis&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>A <sup>186</sup>Re-glucoheptonate ligand exchange reaction was used for the synthesis of [<sup>186</sup>Re]MAMA-BP and <sup>186</sup>Re-1-hydroxyethylidene-1,1-diphosphonate ([<sup>186</sup>Re]-MAMA-HEDP; used as a control in the various studies) and is detailed elsewhere (<a class="bk_pop" href="#MAMABP186Re.REF.6">6</a>). The radiochemical yield of [<sup>186</sup>Re]MAMA-BP was reported to be between 21.3 ± 4.5 and 32.0 ± 4.1% with a purity of 96.4 ± 1.4%. Specific activity of the radiolabeled compounds was not reported.</p></div><div id="MAMABP186Re.In_Vitro_Studies_Testing_in"><h2 id="_MAMABP186Re_In_Vitro_Studies_Testing_in_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed?term=nitrogen%20containing%20bisphosphonate%20in%20vitro%20stability&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The <i>in vitro</i> stability of [<sup>186</sup>Re]MAMA-BP after a 24-h incubation in 0.1 M phosphate-buffered saline (pH, 7.0) saturated with 95% O<sub>2</sub> and 5% CO<sub>2</sub> at 37°C was reported to be 81.8 ± 1.7% as determined with reversed-phase high-performance liquid chromatography or thin-layer chromatography. Under the same conditions, the stability of [<sup>186</sup>Re]MAMA-HBP was reported to be 75.55 ± 1.57%.</p><p>The HA binding of [<sup>186</sup>Re]MAMA-BP was determined by using different amounts (1–25 mg/mL) of commercially available HA beads suspended in Tris/HCl-buffered saline (pH, 7.4) as described by Ogawa et al. (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). The percent of HA binding was determined with an equation given elsewhere (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). Approximately 40% of [<sup>186</sup>Re]MAMA-BP bound to the HA beads at the lowest concentration (compared with ~70% for [<sup>186</sup>Re]MAMA-HBP) and increased to ~95.0% at the highest concentration (compared with ~97.5% for [<sup>186</sup>Re]MAMA-HBP). Results from this study indicated that [<sup>186</sup>Re]MAMA-HBP had a higher affinity for HA than [<sup>186</sup>Re]MAMA-BP.</p></div><div id="MAMABP186Re.Animal_Studies"><h2 id="_MAMABP186Re_Animal_Studies_">Animal Studies</h2><div id="MAMABP186Re.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed?term=nitrogen%20containing%20bisphosphonate%20rodentia&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of [<sup>186</sup>Re]MAMA-BP and [<sup>186</sup>Re]MAMA-HBP was investigated in normal, male ddY mice after intravenous administration of the respective labeled compounds (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). For this study, another NBP, [<sup>186</sup>Re]HEDP, was used as a control. The animals (<i>n</i> = 5–6 mice per time point) were euthanized at designated time points ranging from 10 min to 24 h postinjection (p.i.). Organs of interest (liver, kidney, blood, intestine, stomach, and the complete left femur) were removed from the cadavers and weighed, and the amount of radioactivity accumulated in the tissues was measured, and the data were presented as percent injected dose per gram tissue (% ID/g).</p><p>The tissue distribution pattern of radioactivity from [<sup>186</sup>Re]MAMA-BP was reported to be similar to that observed with [<sup>186</sup>Re]MAMA-HBP and [<sup>186</sup>Re]MAMA-HEDP (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). Maximum label was deposited on the femur at all time points with the radiochemicals (21.38 ± 3.83% ID/g with [<sup>186</sup>Re]MAMA-BP, 24.80 ± 2.41% ID/g with [<sup>186</sup>Re]MAMA-HBP, and 13.09 ± 2.90% ID/g with [<sup>186</sup>Re]MAMA-HEDP) at 24 h p.i., followed by the kidneys (varying from 2.43 ± 0.53% ID/g with [<sup>186</sup>Re]MAMA-BP to 0.42 ± 0.10% ID/g with [<sup>186</sup>Re]MAMA-HEDP) at the same time point. The femur/blood ratios of radioactivity were ~1,200 with [<sup>186</sup>Re]MAMA-HBP compared with ~800 and ~400 with [<sup>186</sup>Re]MAMA-BP and [<sup>186</sup>Re]MAMA-HEDP, respectively. In addition, the blood clearance of radioactivity from [<sup>186</sup>Re]MAMA-HEDP was slower than that of the other two <sup>186</sup>Re-labeled MAMA-bisphosphonates, and it had a lower accumulation in the liver.</p><p>Ogawa et al. calculated the radiation dose estimates for the three bisphosphonates for adult patients by monoexponential extrapolation of the biodistribution data (<a class="bk_pop" href="#MAMABP186Re.REF.3">3</a>). Although the red-marrow/bone-surface and total-body/bone-surface ratios for all the radiolabeled compounds were the same, the effective-dose/bone-surface ratio of [<sup>186</sup>Re]MAMA-HEDP was higher than that of either [<sup>186</sup>Re]MAMA-BP or [<sup>186</sup>Re]MAMA-HBP.</p></div><div id="MAMABP186Re.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed?term=nitrogen%20containing%20bisphosphonates%20non%20primate%20mammal%20studies&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="MAMABP186Re.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed?term=nitrogen%20containing%20bisphosphonates%20non%20human%20primate%20studies&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="MAMABP186Re.Human_Studies"><h2 id="_MAMABP186Re_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed?term=dipicolylamine-alendronate%20Human%20Studies&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="MAMABP186Re.Supplemental_Information"><h2 id="_MAMABP186Re_Supplemental_Information_">Supplemental Information</h2><p>[<a href="/books/n/micad/disclaimer/">Disclaimers</a>]</p><p>No information is currently available.</p></div><div id="MAMABP186Re.References"><h2 id="_MAMABP186Re_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="MAMABP186Re.REF.1">Kimmel D.B.
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<em>Mechanism of action, pharmacokinetic and pharmacodynamic profile, and clinical applications of nitrogen-containing bisphosphonates.</em>
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<span><span class="ref-journal">J Dent Res. </span>2007;<span class="ref-vol">86</span>(11):1022–33.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17959891" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17959891</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="MAMABP186Re.REF.2">Drake M.T., Clarke B.L., Khosla S.
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<em>Bisphosphonates: mechanism of action and role in clinical practice.</em>
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||
<span><span class="ref-journal">Mayo Clin Proc. </span>2008;<span class="ref-vol">83</span>(9):1032–45.</span> [<a href="/pmc/articles/PMC2667901/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2667901</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/18775204" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18775204</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="MAMABP186Re.REF.3">Ogawa K., Mukai T., Arano Y., Otaka A., Ueda M., Uehara T., Magata Y., Hashimoto K., Saji H.
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<em>Rhemium-186-monoaminemonoamidedithiol-conjugated bisphosphonate derivatives for bone pain palliation.</em>
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||
<span><span class="ref-journal">Nucl Med Biol. </span>2006;<span class="ref-vol">33</span>(4):513–20.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16720243" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16720243</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="MAMABP186Re.REF.4">Torres Martin de Rosales R., Finucane C., Mather S.J., Blower P.J.
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<em>Bifunctional bisphosphonate complexes for the diagnosis and therapy of bone metastases.</em>
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||
<span><span class="ref-journal">Chem Commun (Camb). </span>2009;(32):4847–9.</span> [<a href="/pmc/articles/PMC7116767/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC7116767</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/19652801" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19652801</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="MAMABP186Re.REF.5">Chopra, A., <em>186Re-Labeled [N-2[[4-[(4-hydroxy-4,4-diphosphonobutyl)amino]-4-oxobutyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] conjugated to hydroxyl-bisphosphonate.</em> Molecular Imaging and Contrast agent Database (MICAD) [database online]. National Library of Medicine, NCBI, Bethesda, MD, USA. Available from <a href="http://www.micad.nih.gov/" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">www<wbr style="display:inline-block"></wbr>.micad.nih.gov</a>, 2004 -to current.</div></dd><dt>6.</dt><dd><div class="bk_ref" id="MAMABP186Re.REF.6">Ogawa K., Mukai T., Arano Y., Hanaoka H., Hashimoto K., Nishimura H., Saji H.
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<em>Design of a radiopharmaceutical for the pallation of painful bone metastases: rhenium-186-labeled bisphosphonate derivative.</em>
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<span><span class="ref-journal">J. Label. Compd. Radiopharm. </span>2004;<span class="ref-vol">47</span>:753–761.</span></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: NBK44814</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20642012" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20642012</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/sos186re/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/MAMAHBP186Re/" 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/NBK44814/?report=reader">PubReader</a></li><li><a href="/books/NBK44814/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK44814" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK44814" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. 186Re-Labeled [N-[2[[3-(3,3-diphosphonopropylcarbamoyl)propyl]-2-thioethylamino]acetyl]-2-aminoethylenethiolate] oxorhenium (V) 2009 Nov 6 [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/NBK44814/pdf/Bookshelf_NBK44814.pdf">PDF version of this page</a> (139K)</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="#MAMABP186Re.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#MAMABP186Re.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#MAMABP186Re.In_Vitro_Studies_Testing_in" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#MAMABP186Re.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#MAMABP186Re.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#MAMABP186Re.Supplemental_Information" ref="log$=inpage&link_id=inpage">Supplemental Information</a></li><li><a href="#MAMABP186Re.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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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (186)Re-Labeled [N-[2-[[4-[(4-hydroxy-4,4-diphosphonobutyl)amino]-4-oxobutyl]-2-thioethylamino]acetyl]-2-aminoethanethiolate] oxorhenium (V).</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (186)Re-Labeled [N-[2-[[4-[(4-hydroxy-4,4-diphosphonobutyl)amino]-4-oxobutyl]-2-thioethylamino]acetyl]-2-aminoethanethiolate] oxorhenium (V).<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Chopra A. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/20642002" ref="ordinalpos=1&linkpos=2&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Labeled mercaptoacetylglycylglycylglycine conjugated to hydroxy-bisphosphonate.</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Labeled mercaptoacetylglycylglycylglycine conjugated to hydroxy-bisphosphonate.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Chopra A. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" 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