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<script type="text/javascript" src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.boots.min.js"> </script><title>[99mTc]-1,4,7,10-Tetraazacyclododecane tetramethylenephosphonic acid - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]">
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<meta name="citation_title" content="[99mTc]-1,4,7,10-Tetraazacyclododecane tetramethylenephosphonic acid">
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<meta name="citation_publisher" content="National Center for Biotechnology Information (US)">
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<meta name="citation_date" content="2009/06/09">
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<meta name="citation_author" content="Anupama Datta">
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<meta name="citation_author" content="Puja Panwar">
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<meta name="citation_author" content="Krishna Chuttani">
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<meta name="citation_author" content="Anil Kumar Mishra">
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<meta name="citation_author" content="Arvind Chopra">
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<meta name="citation_pmid" content="20641623">
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<meta name="DC.Title" content="[99mTc]-1,4,7,10-Tetraazacyclododecane tetramethylenephosphonic acid">
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<meta name="DC.Publisher" content="National Center for Biotechnology Information (US)">
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<meta name="DC.Contributor" content="Anupama Datta">
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<meta name="DC.Contributor" content="Puja Panwar">
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<meta name="DC.Contributor" content="Krishna Chuttani">
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<meta name="DC.Contributor" content="Anil Kumar Mishra">
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<meta name="DC.Contributor" content="Arvind Chopra">
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<meta name="DC.Date" content="2009/06/09">
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<meta name="description" content="Pathological conditions such as neoplastic diseases, metabolic disorders, infections, and cancers often result in metastases of the disease to the skeletal system. During the past 50 years, a variety of bone-seeking radiopharmaceuticals have been developed and evaluated to detect skeletal metastases by imaging (1-3) or as pain palliative agents in patients (4). The diagnostic radiochemicals, usually phosphate and phosphonate derivatives of compounds, are particularly useful to detect the metastasis because they localize avidly in the bone (5, 6). Most bone lesions have an elevated concentration of minerals (mostly calcium salts) that form a major part of the matrix surface area, and these lesions have a high affinity for and facilitate the adsorption of the bone imaging agents (1, 7). Compared to phosphates, the phosphonate compounds are more stable under in vivo conditions because the phosphate bond with oxygen in pyrophosphate (P-O-P) is easily cleaved by chemical or enzymatic action, whereas the phosphonate bond in the diphosphonate (P-C-P) is insensitive to enzymatic or chemical action (8). Because of its stability and long retention in the bone, radionuclide-labeled methylene diphosphonate and its derivatives are routinely used for bone imaging to detect fractures or to detect and treat osteomyelitis and cancer metastasis (9-11). Radioactive samarium (153Sm) coupled to a tetraphosphonate (ethylenediamine-tetramethylenephosphonic acid (153Sm-lexidronam)) is approved by the United States Food and Drug Administration for pain palliation as a result of cancer that has metastasized to the bone. Similarly, another tetraphosphonate, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP), was conjugated with radioactive bismuth (212Bi, a γ emitter) and has been shown to be promising for the treatment of bone cancer under preclinical conditions (12).">
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<meta name="og:description" content="Pathological conditions such as neoplastic diseases, metabolic disorders, infections, and cancers often result in metastases of the disease to the skeletal system. During the past 50 years, a variety of bone-seeking radiopharmaceuticals have been developed and evaluated to detect skeletal metastases by imaging (1-3) or as pain palliative agents in patients (4). The diagnostic radiochemicals, usually phosphate and phosphonate derivatives of compounds, are particularly useful to detect the metastasis because they localize avidly in the bone (5, 6). Most bone lesions have an elevated concentration of minerals (mostly calcium salts) that form a major part of the matrix surface area, and these lesions have a high affinity for and facilitate the adsorption of the bone imaging agents (1, 7). Compared to phosphates, the phosphonate compounds are more stable under in vivo conditions because the phosphate bond with oxygen in pyrophosphate (P-O-P) is easily cleaved by chemical or enzymatic action, whereas the phosphonate bond in the diphosphonate (P-C-P) is insensitive to enzymatic or chemical action (8). Because of its stability and long retention in the bone, radionuclide-labeled methylene diphosphonate and its derivatives are routinely used for bone imaging to detect fractures or to detect and treat osteomyelitis and cancer metastasis (9-11). Radioactive samarium (153Sm) coupled to a tetraphosphonate (ethylenediamine-tetramethylenephosphonic acid (153Sm-lexidronam)) is approved by the United States Food and Drug Administration for pain palliation as a result of cancer that has metastasized to the bone. Similarly, another tetraphosphonate, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP), was conjugated with radioactive bismuth (212Bi, a γ emitter) and has been shown to be promising for the treatment of bone cancer under preclinical conditions (12).">
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id="jr-fip-info-p"><a id="jr-fip-prev" class="wsprkl btn" title="Jump to previuos match">◀</a><button id="jr-fip-matches">no matches yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK23424_"><span class="title" itemprop="name">[<sup>99m</sup>Tc]-1,4,7,10-Tetraazacyclododecane tetramethylenephosphonic acid</span></h1><p class="contribs">Datta A, Panwar P, Chuttani K, et al.</p><p class="fm-aai"><a href="#_NBK23424_pubdet_">Publication Details</a></p></div></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figDOTMP99mTcTncchemicalname99mtc14710t"><a href="/books/NBK23424/table/DOTMP99mTc.T.nc_chemical_name99mtc14710t/?report=objectonly" target="object" title="Table" class="img_link icnblk_img figpopup" rid-figpopup="figDOTMP99mTcTncchemicalname99mtc14710t" rid-ob="figobDOTMP99mTcTncchemicalname99mtc14710t"><img class="small-thumb" src="/books/NBK23424/table/DOTMP99mTc.T.nc_chemical_name99mtc14710t/?report=thumb" src-large="/books/NBK23424/table/DOTMP99mTc.T.nc_chemical_name99mtc14710t/?report=previmg" alt="Image " /></a><div class="icnblk_cntnt"><h4 id="DOTMP99mTc.T.nc_chemical_name99mtc14710t"><a href="/books/NBK23424/table/DOTMP99mTc.T.nc_chemical_name99mtc14710t/?report=objectonly" target="object" rid-ob="figobDOTMP99mTcTncchemicalname99mtc14710t">Table</a></h4><p class="float-caption no_bottom_margin">
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<i>In vitro</i>
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Rodents
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</p></div></div><div id="DOTMP99mTc.Background"><h2 id="_DOTMP99mTc_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%22SUBSTANCENAME%22%5BSubstance%20Name%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Pathological conditions such as neoplastic diseases, metabolic disorders, infections, and cancers often result in metastases of the disease to the skeletal system. During the past 50 years, a variety of bone-seeking radiopharmaceuticals have been developed and evaluated to detect skeletal metastases by imaging (<a class="bibr" href="#DOTMP99mTc.REF.1" rid="DOTMP99mTc.REF.1 DOTMP99mTc.REF.2 DOTMP99mTc.REF.3">1-3</a>) or as pain palliative agents in patients (<a class="bibr" href="#DOTMP99mTc.REF.4" rid="DOTMP99mTc.REF.4">4</a>). The diagnostic radiochemicals, usually phosphate and phosphonate derivatives of compounds, are particularly useful to detect the metastasis because they localize avidly in the bone (<a class="bibr" href="#DOTMP99mTc.REF.5" rid="DOTMP99mTc.REF.5 DOTMP99mTc.REF.6">5, 6</a>). Most bone lesions have an elevated concentration of minerals (mostly calcium salts) that form a major part of the matrix surface area, and these lesions have a high affinity for and facilitate the adsorption of the bone imaging agents (<a class="bibr" href="#DOTMP99mTc.REF.1" rid="DOTMP99mTc.REF.1 DOTMP99mTc.REF.7">1, 7</a>). Compared to phosphates, the phosphonate compounds are more stable under <i>in vivo</i> conditions because the phosphate bond with oxygen in pyrophosphate (P-O-P) is easily cleaved by chemical or enzymatic action, whereas the phosphonate bond in the diphosphonate (P-C-P) is insensitive to enzymatic or chemical action (<a class="bibr" href="#DOTMP99mTc.REF.8" rid="DOTMP99mTc.REF.8">8</a>). Because of its stability and long retention in the bone, radionuclide-labeled methylene diphosphonate and its derivatives are routinely used for bone imaging to detect fractures or to detect and treat osteomyelitis and cancer metastasis (<a class="bibr" href="#DOTMP99mTc.REF.9" rid="DOTMP99mTc.REF.9 DOTMP99mTc.REF.10 DOTMP99mTc.REF.11">9-11</a>). Radioactive samarium (<sup>153</sup>Sm) coupled to a tetraphosphonate (ethylenediamine-tetramethylenephosphonic acid (<sup>153</sup>Sm-lexidronam)) is <a href="http://www.cytogen.com/professional/quadramet/pi.php" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">approved</a> by the United States Food and Drug Administration for pain palliation as a result of cancer that has metastasized to the bone. Similarly, another tetraphosphonate, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP), was conjugated with radioactive bismuth (<sup>212</sup>Bi, a γ emitter) and has been shown to be promising for the treatment of bone cancer under preclinical conditions (<a class="bibr" href="#DOTMP99mTc.REF.12" rid="DOTMP99mTc.REF.12">12</a>).</p><p>In an effort to develop an imaging agent, Datta et al. (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>) envisioned that DOTMP conjugated with radioactive technetium (<sup>99m</sup>Tc-DOTMP) could possibly be used for the early detection of bone cancer or metastasis with single-photon emission computed tomography (SPECT). In a preliminary study the radiolabeled compound was evaluated for bone scintigraphy in normal rabbits, and its biodistribution was investigated in normal BALB/c mice.</p></div><div id="DOTMP99mTc.Synthesis"><h2 id="_DOTMP99mTc_Synthesis_">Synthesis</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=99mTc+DOTMP+synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The synthesis of DOTMP was done by a modified method of Myers (<a class="bibr" href="#DOTMP99mTc.REF.14" rid="DOTMP99mTc.REF.14">14</a>) as described by Datta et al. (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>). Briefly, 1,4,7,10-tetraazacyclododecane-<i>N</i>,<i>N</i>’,<i>N</i>’’,<i>N</i>’’’-tetraacetic acid (DOTA) was suspended in toluene, and phosphorous acid was added to the suspension. The reaction mixture was then refluxed with the dropwise addition of phosphorous trichloride for 6 h. Toluene was then evaporated under vacuum, and the crude product was dissolved in a minimum amount of deionized water. The concentrated product was precipitated by the addition of methanol and purified with preparative high-performance liquid chromatography. The yield of this reaction was 90%.</p><p>For radiolabeling DOTMP, the compound was mixed with <sup>99m</sup>Tc-pertechnetate (TcO<sub>4</sub><sup>-</sup>) in the presence of stannous chloride (pH 6.0–6.5), and the mixture was incubated for 30 min at room temperature (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>). The radiochemical yield of <sup>99m</sup>Tc-DOTMP was reported to be >97% as determined with silica gel instant thin-layer chromatography. The radiochemical purity of <sup>99m</sup>Tc-DOTMP was determined as described by Panwar et al. (<a class="bibr" href="#DOTMP99mTc.REF.5" rid="DOTMP99mTc.REF.5">5</a>) and reported to be >97%. The specific activity of <sup>99m</sup>Tc-DOTMP was reported to be 185 MBq/mmol (5 Ci/mmol) (personal communication).</p><p>The stability of <sup>99m</sup>Tc-DOTMP was investigated under physiological conditions (method not described by the investigators), and only 2% detachment of <sup>99m</sup>Tc was reported under these conditions (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>). In another experiment (conditions not described), <sup>99m</sup>Tc-DOTMP was mixed with diethylenetriaminepentaacetic acid, and a 7% transchelation of the radiometal was reported.</p></div><div id="DOTMP99mTc.In_Vitro_Studies_Testing_in_C"><h2 id="_DOTMP99mTc_In_Vitro_Studies_Testing_in_C_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=99mTc+DOTMP+in+vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="DOTMP99mTc.Animal_Studies"><h2 id="_DOTMP99mTc_Animal_Studies_">Animal Studies</h2><div id="DOTMP99mTc.Rodents"><h3>Rodents</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=99mTc+DOTMP+rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The biodistribution of <sup>99m</sup>Tc-DOTMP was studied in BALB/c mice injected intravenously (i.v.) with the radiolabeled compound through the tail vein (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>). All major organs were harvested from the animals (<i>n</i> = 5 mice/time point) at various time points starting at 30 min up to 24 h after administration of the radiopharmaceutical. At 30 min the radioactivity was detected mainly in the kidneys (4.36 ± 0.42% injected dose/gram tissue (% ID/g)), bones (4.74 ± 0.36% ID/g), and blood (1.31 ± 0.40% ID/g). At this time point all other organs showed an accumulation of between 0.11 ± 0.02% ID/g (intestines) and 0.58 ± 0.18% ID/g (lungs) of the radioactivity. By 24 h after injection of <sup>99m</sup>Tc-DOTMP, the amount of radioactivity accumulated in the bones was 3.03 ± 0.26% ID/g, and in the kidneys it was 0.67 ± 0.14% ID/g. At 24 h all other organs had accumulated radioactivity between 0.04 ± 0.09% ID/g (muscles) and 0.16 ± 0.07% ID/g (spleen). Data from this study indicated that there was a rapid accumulation of radioactivity in the bones and kidneys; by 24 h most of the radiolabel remained bound to the bones, but the kidneys lost most of the label by excretion through the urinary route. The investigators concluded that <sup>99m</sup>Tc-DOTMP could probably be used for pretherapeutic diagnostic imaging of bone metastases in animal models.</p></div><div id="DOTMP99mTc.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=99mTc+DOTMP+Non+Primate+Mammals" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Datta et al. performed imaging studies on a normal rabbit after the administration of <sup>99m</sup>Tc-DOTMP by an i.v. injection through the dorsal ear vein (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>). Images were obtained at different time intervals starting at 30 min after injection of the radiolabel for up to 24 h. From the scintigraphic images it was evident that the radioactivity accumulated rapidly, within 30 min of administration, in the entire skeleton of the rabbit. During the same period, little accumulation of radioactivity was observed in the nonosseous tissue of the animal. A high amount of label was visible in the kidneys and the urinary bladder, indicating that the radioactivity was also excreted in this animal through the urinary route.</p><p>In another study on rabbits it was revealed that <sup>99m</sup>Tc-DOTMP had a rapid clearance from the blood (<a class="bibr" href="#DOTMP99mTc.REF.13" rid="DOTMP99mTc.REF.13">13</a>). Approximately 60% of radioactivity was cleared from blood in <5 min after administration of the radiochemical, and the clearance was >90% by 1 h. The biological half-lives of <sup>99m</sup>Tc-DOTMP under these experimental conditions were reported to be 25 min (F) and 6 h 5 min (S).</p></div><div id="DOTMP99mTc.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=99mTc+DOTMP+Non+Human+Primates" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div></div><div id="DOTMP99mTc.Human_Studies"><h2 id="_DOTMP99mTc_Human_Studies_">Human Studies</h2><p>[<a href="/sites/entrez?Db=pubmed&Cmd=DetailsSearch&Term=99mTc+DOTMP+Human+Studies" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No references are currently available.</p></div><div id="DOTMP99mTc.References"><h2 id="_DOTMP99mTc_References_">References</h2><dl class="temp-labeled-list"><dl class="bkr_refwrap"><dt>1.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.1">Ergun E.L., Kiratli P.O., Gunay E.C., Erbas B.
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<em>A report on the incidence of intestinal 99mTc-methylene diphosphonate uptake of bone scans and a review of the literature.</em>
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<span><span class="ref-journal">Nucl Med Commun. </span>2006;<span class="ref-vol">27</span>(11):877–85.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17021428" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17021428</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>2.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.2">Kumar V., Kumar D., Howman-Giles R.B., Little D.G.
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<em>Is (99m)Tc-labelled pamidronate a better agent than (99m)Tc-medronate for bone imaging?</em>
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<span><span class="ref-journal">Nucl Med Commun. </span>2007;<span class="ref-vol">28</span>(2):101–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17198350" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17198350</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>3.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.3">Ogawa K., Mukai T., Inoue Y., Ono M., Saji H.
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<em>Development of a novel 99mTc-chelate-conjugated bisphosphonate with high affinity for bone as a bone scintigraphic agent.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2006;<span class="ref-vol">47</span>(12):2042–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17138748" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17138748</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>4.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.4">Chakraborty S., Das T., Banerjee S., Balogh L., Chaudhari P.R., Sarma H.D., Polyak A., Mathe D., Venkatesh M., Janoki G., Pillai M.R.
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<em>177Lu-EDTMP: a viable bone pain palliative in skeletal metastasis.</em>
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<span><span class="ref-journal">Cancer Biother Radiopharm. </span>2008;<span class="ref-vol">23</span>(2):202–13.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18454689" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18454689</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>5.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.5">Panwar P., Chuttani K., Mishra P., Sharma R., Mondal A., Kumar Mishra A.
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<em>Synthesis of trans-1,2-cyclohexyldinitrilo tetramethylene phosphonic acid and its radiolabelling with 99mTc for the detection of skeletal metastases.</em>
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<span><span class="ref-journal">Nucl Med Commun. </span>2006;<span class="ref-vol">27</span>(8):619–26.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16829762" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16829762</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>6.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.6">Moore A.E., Blake G.M., Fogelman I.
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<em>Quantitative measurements of bone remodeling using 99mTc-methylene diphosphonate bone scans and blood sampling.</em>
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<span><span class="ref-journal">J Nucl Med. </span>2008;<span class="ref-vol">49</span>(3):375–82.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18287266" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18287266</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>7.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.7">Toegel S., Hoffmann O., Wadsak W., Ettlinger D., Mien L.K., Wiesner K., Nguemo J., Viernstein H., Kletter K., Dudczak R., Mitterhauser M.
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<em>Uptake of bone-seekers is solely associated with mineralisation! A study with 99mTc-MDP, 153Sm-EDTMP and 18F-fluoride on osteoblasts.</em>
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<span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2006;<span class="ref-vol">33</span>(4):491–4.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16416330" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16416330</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>8.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.8">Hirabayashi H., Fujisaki J.
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<em>Bone-specific drug delivery systems: approaches via chemical modification of bone-seeking agents.</em>
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<span><span class="ref-journal">Clin Pharmacokinet. </span>2003;<span class="ref-vol">42</span>(15):1319–30.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14674786" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14674786</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>9.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.9">Lenora J., Norrgren K., Thorsson O., Wollmer P., Obrant K.J., Ivaska K.K.
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<em>Bone turnover markers are correlated with total skeletal uptake of 99mTc-methylene diphosphonate (99mTc-MDP).</em>
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<span><span class="ref-journal">BMC Med Phys. </span>2009;<span class="ref-vol">9</span>(1):3.</span> [<a href="/pmc/articles/PMC2674029/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2674029</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/19331678" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19331678</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>10.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.10">Pauwels E.K., Blom J., Camps J.A., Hermans J., Rijke A.M.
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<em>A comparison between the diagnostic efficacy of 99mTc-MDP, 99mTc-DPD and 99mTc-HDP for the detection of bone metastases.</em>
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<span><span class="ref-journal">Eur J Nucl Med. </span>1983;<span class="ref-vol">8</span>(3):118–22.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6220908" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 6220908</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>11.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.11">Vorne M., Vahatalo S., Lantto T.
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<em>A clinical comparison of 99mTc-DPD and two 99mTc-MDP agents.</em>
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<span><span class="ref-journal">Eur J Nucl Med. </span>1983;<span class="ref-vol">8</span>(9):395–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/6226527" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 6226527</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>12.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.12">Hassfjell S.P., Bruland O.S., Hoff P.
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<em>212Bi-DOTMP: an alpha particle emitting bone-seeking agent for targeted radiotherapy.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>1997;<span class="ref-vol">24</span>(3):231–7.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9228657" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9228657</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>13.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.13">Datta A., Panwar P., Chuttani K., Mishra A.K.
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<em>Synthesis of 99mTc-DOTMP and its preclinical evaluation as a multidentate imaging agent for skeletal metastases.</em>
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<span><span class="ref-journal">Cancer Biother Radiopharm. </span>2009;<span class="ref-vol">24</span>(1):123–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19243254" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19243254</span></a>]</div></dd></dl><dl class="bkr_refwrap"><dt>14.</dt><dd><div class="bk_ref" id="DOTMP99mTc.REF.14">Myers H.M.
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<em>Structure-activity relationships (SAR) of hydroxyapatite-binding molecules.</em>
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<span><span class="ref-journal">Calcif Tissue Int. </span>1987;<span class="ref-vol">40</span>(6):344–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/3038282" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 3038282</span></a>]</div></dd></dl></dl></div><div><dl class="temp-labeled-list small"><dl class="bkr_refwrap"><dt></dt><dd><div><p class="no_top_margin"><div>This MICAD chapter is not included in the Open Access Subset, because it was authored / co-authored by one or more investigators who was not a member of the MICAD staff.</div></p></div></dd></dl></dl></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK23424_pubdet_">Publication Details</h2><h3>Author Information and Affiliations</h3><div class="contrib half_rhythm"><span itemprop="author">Anupama Datta</span>, Ph.D<div class="affiliation small">Institute of Nuclear Medicine and Allied Sciences, New Delhi, India<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="moc.liamtoh@ahbauna" class="oemail">moc.liamtoh@ahbauna</a></div></div></div><div class="contrib half_rhythm"><span itemprop="author">Puja Panwar</span>, Ph.D<div class="affiliation small">Institute of Nuclear Medicine and Allied Sciences, New Delhi, India<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="ni.odrd.samni@ajup" class="oemail">ni.odrd.samni@ajup</a></div></div></div><div class="contrib half_rhythm"><span itemprop="author">Krishna Chuttani</span>, MSc<div class="affiliation small">Institute of Nuclear Medicine and Allied Sciences, New Delhi, India<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="moc.oohay@2inattuhcanhsirK" class="oemail">moc.oohay@2inattuhcanhsirK</a></div></div></div><div class="contrib half_rhythm"><span itemprop="author">Anil Kumar Mishra</span>, Ph.D<div class="affiliation small">Institute of Nuclear Medicine and Allied Sciences, New Delhi, India<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="gro.samni@arhsimka" class="oemail">gro.samni@arhsimka</a></div></div></div><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><h3>Publication History</h3><p class="small">Created: <span itemprop="datePublished">March 31, 2009</span>; Last Update: <span itemprop="dateModified">June 9, 2009</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="http://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>Datta A, Panwar P, Chuttani K, et al. [99mTc]-1,4,7,10-Tetraazacyclododecane tetramethylenephosphonic acid. 2009 Mar 31 [Updated 2009 Jun 9]. 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></p></div><div class="small-screen-prev"><a href="/books/n/micad/IMP24599mTc/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/micad/NPNP99mTc/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobDOTMP99mTcTncchemicalname99mtc14710t"><div id="DOTMP99mTc.T.nc_chemical_name99mtc14710t" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23424/table/DOTMP99mTc.T.nc_chemical_name99mtc14710t/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__DOTMP99mTc.T.nc_chemical_name99mtc14710t_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>99m</sup>Tc]-1,4,7,10-Tetraazacyclododecane tetramethylenephosphonic acid<br /></td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<span class="graphic"><img src="/books/NBK23424/bin/DOTMP.jpg" alt="Image DOTMP.jpg" /></span>
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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>99m</sup>Tc]-DOTMP<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;">Bone calcium</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;">Organ</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>99m</sup>Tc</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;">Structure of DOTMP</td></tr></tbody></table></div></div></article></div><div id="jr-scripts"><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/libs.min.js"> </script><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.min.js"> </script></div></div>
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