Rationale of 5-(125)I-iodo-4'-thio-2'-deoxyuridine as a potential iodinated proliferation marker
The aim of this investigation was to synthesize and test a novel metabolically stable iodinated nucleoside as a proliferation-imaging agent for SPECT. 5-Iodo-4'-thio-2'-deoxyuridine (ITdU) and 5-iodo-1-(4-thio-beta-D-arabinofuranosyl)uracil (ITAU) were tested. The radiolabeling of ITdU and...
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| Veröffentlicht in: | The Journal of nuclear medicine (1978) 2002-09, Vol.43 (9), p.1218-1226 |
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| creator | Toyohara, Jun Hayashi, Akio Sato, Mikiko Tanaka, Hiromichi Haraguchi, Kazuhiro Yoshimura, Yuichi Yonekura, Yoshiharu Fujibayashi, Yasuhisa |
| description | The aim of this investigation was to synthesize and test a novel metabolically stable iodinated nucleoside as a proliferation-imaging agent for SPECT.
5-Iodo-4'-thio-2'-deoxyuridine (ITdU) and 5-iodo-1-(4-thio-beta-D-arabinofuranosyl)uracil (ITAU) were tested. The radiolabeling of ITdU and ITAU with (125)I was achieved by a destannylation reaction of the trimethylstannyl precursor of each nucleoside. The products were isolated in high yields and with >99% radiochemical purities.
(125)I-ITdU was effectively phosphorylated by cytosolic nucleoside kinases and specifically incorporated into a thymidine kinase-expressing L-M cell rather than a thymidine kinase-deficient mutant L-M (TK(-)) cell. In addition, an in vitro cell metabolism study of (125)I-ITdU clarified that (125)I-ITdU was effectively and specifically incorporated into a DNA fraction (>90% at 60 min). Therefore, (125)I-ITdU was proven to be an ideal DNA synthesis marker such as 5-(125)I-iodo-2'-deoxyuridine (IUdR). In contrast, (125)I-ITAU was neither remarkably phosphorylated by cytosolic nucleoside kinases nor notably incorporated into an L-M cell rather than an L-M (TK(-)) cell. (125)I-ITdU and (125)I-ITAU showed a higher resistance to phosphorolytic cleavage by recombinant thymidine phosphorylase than did (125)I-IUdR. Furthermore, biodistribution of (125)I-ITdU and (125)I-ITAU revealed better in vivo stability of radioiodination than that of (125)I-IUdR. (125)I-ITdU also displayed a significantly higher uptake in proliferating organs (thymus, spleen, small intestine, and bone) than in nonproliferating organs (brain, muscle, liver, and lung), as did (125)I-IUdR, at 18 h after injection. As indicated by the in vitro study, (125)I-ITAU did not show any significant uptake in proliferating organs.
Radioiodine-labeled ITdU is potentially useful as a proliferation-imaging agent, and further studies should clarify the usefulness of this compound as a tumor-imaging agent. |
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5-Iodo-4'-thio-2'-deoxyuridine (ITdU) and 5-iodo-1-(4-thio-beta-D-arabinofuranosyl)uracil (ITAU) were tested. The radiolabeling of ITdU and ITAU with (125)I was achieved by a destannylation reaction of the trimethylstannyl precursor of each nucleoside. The products were isolated in high yields and with >99% radiochemical purities.
(125)I-ITdU was effectively phosphorylated by cytosolic nucleoside kinases and specifically incorporated into a thymidine kinase-expressing L-M cell rather than a thymidine kinase-deficient mutant L-M (TK(-)) cell. In addition, an in vitro cell metabolism study of (125)I-ITdU clarified that (125)I-ITdU was effectively and specifically incorporated into a DNA fraction (>90% at 60 min). Therefore, (125)I-ITdU was proven to be an ideal DNA synthesis marker such as 5-(125)I-iodo-2'-deoxyuridine (IUdR). In contrast, (125)I-ITAU was neither remarkably phosphorylated by cytosolic nucleoside kinases nor notably incorporated into an L-M cell rather than an L-M (TK(-)) cell. (125)I-ITdU and (125)I-ITAU showed a higher resistance to phosphorolytic cleavage by recombinant thymidine phosphorylase than did (125)I-IUdR. Furthermore, biodistribution of (125)I-ITdU and (125)I-ITAU revealed better in vivo stability of radioiodination than that of (125)I-IUdR. (125)I-ITdU also displayed a significantly higher uptake in proliferating organs (thymus, spleen, small intestine, and bone) than in nonproliferating organs (brain, muscle, liver, and lung), as did (125)I-IUdR, at 18 h after injection. As indicated by the in vitro study, (125)I-ITAU did not show any significant uptake in proliferating organs.
Radioiodine-labeled ITdU is potentially useful as a proliferation-imaging agent, and further studies should clarify the usefulness of this compound as a tumor-imaging agent.</description><identifier>ISSN: 0161-5505</identifier><identifier>EISSN: 1535-5667</identifier><identifier>PMID: 12215562</identifier><identifier>CODEN: JNMEAQ</identifier><language>eng</language><publisher>United States: Society of Nuclear Medicine</publisher><subject>Animals ; Arabinofuranosyluracil ; Cell Division ; Deoxyuridine - analogs & derivatives ; Humans ; Iodine Radioisotopes ; Isotope Labeling ; Mice ; Mice, Inbred C57BL ; Monosaccharides ; Tissue Distribution ; Tomography, Emission-Computed, Single-Photon ; Uracil - analogs & derivatives ; Uridine</subject><ispartof>The Journal of nuclear medicine (1978), 2002-09, Vol.43 (9), p.1218-1226</ispartof><rights>Copyright Society of Nuclear Medicine Sep 2002</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12215562$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Toyohara, Jun</creatorcontrib><creatorcontrib>Hayashi, Akio</creatorcontrib><creatorcontrib>Sato, Mikiko</creatorcontrib><creatorcontrib>Tanaka, Hiromichi</creatorcontrib><creatorcontrib>Haraguchi, Kazuhiro</creatorcontrib><creatorcontrib>Yoshimura, Yuichi</creatorcontrib><creatorcontrib>Yonekura, Yoshiharu</creatorcontrib><creatorcontrib>Fujibayashi, Yasuhisa</creatorcontrib><title>Rationale of 5-(125)I-iodo-4'-thio-2'-deoxyuridine as a potential iodinated proliferation marker</title><title>The Journal of nuclear medicine (1978)</title><addtitle>J Nucl Med</addtitle><description>The aim of this investigation was to synthesize and test a novel metabolically stable iodinated nucleoside as a proliferation-imaging agent for SPECT.
5-Iodo-4'-thio-2'-deoxyuridine (ITdU) and 5-iodo-1-(4-thio-beta-D-arabinofuranosyl)uracil (ITAU) were tested. The radiolabeling of ITdU and ITAU with (125)I was achieved by a destannylation reaction of the trimethylstannyl precursor of each nucleoside. The products were isolated in high yields and with >99% radiochemical purities.
(125)I-ITdU was effectively phosphorylated by cytosolic nucleoside kinases and specifically incorporated into a thymidine kinase-expressing L-M cell rather than a thymidine kinase-deficient mutant L-M (TK(-)) cell. In addition, an in vitro cell metabolism study of (125)I-ITdU clarified that (125)I-ITdU was effectively and specifically incorporated into a DNA fraction (>90% at 60 min). Therefore, (125)I-ITdU was proven to be an ideal DNA synthesis marker such as 5-(125)I-iodo-2'-deoxyuridine (IUdR). In contrast, (125)I-ITAU was neither remarkably phosphorylated by cytosolic nucleoside kinases nor notably incorporated into an L-M cell rather than an L-M (TK(-)) cell. (125)I-ITdU and (125)I-ITAU showed a higher resistance to phosphorolytic cleavage by recombinant thymidine phosphorylase than did (125)I-IUdR. Furthermore, biodistribution of (125)I-ITdU and (125)I-ITAU revealed better in vivo stability of radioiodination than that of (125)I-IUdR. (125)I-ITdU also displayed a significantly higher uptake in proliferating organs (thymus, spleen, small intestine, and bone) than in nonproliferating organs (brain, muscle, liver, and lung), as did (125)I-IUdR, at 18 h after injection. As indicated by the in vitro study, (125)I-ITAU did not show any significant uptake in proliferating organs.
Radioiodine-labeled ITdU is potentially useful as a proliferation-imaging agent, and further studies should clarify the usefulness of this compound as a tumor-imaging agent.</description><subject>Animals</subject><subject>Arabinofuranosyluracil</subject><subject>Cell Division</subject><subject>Deoxyuridine - analogs & derivatives</subject><subject>Humans</subject><subject>Iodine Radioisotopes</subject><subject>Isotope Labeling</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>Monosaccharides</subject><subject>Tissue Distribution</subject><subject>Tomography, Emission-Computed, Single-Photon</subject><subject>Uracil - analogs & derivatives</subject><subject>Uridine</subject><issn>0161-5505</issn><issn>1535-5667</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNpd0EtLxDAUBeAgijOO_gUJLhxdBHLzarMU8TEwIIiua9rcYsZOU5sWnH9v0XHj6m4-DvecAzIHLTXTxmSHZM7BANOa6xk5SWnDOTd5nh-TGQgBWhsxJ2_PbgixdQ3SWFPNrkDo6xUL0Uemlmx4D5GJJfMYv3ZjH3xokbpEHe3igO0QXEMnG1o3oKddH5tQY_8TSbeu_8D-lBzVrkl4tr8L8np_93L7yNZPD6vbmzXrQNmBASCX3koF3ijuK5tJNNzWVlW-Bq9MmSFX9VQBQHLrMxRSlFkmDNSlqnK5IJe_udMTnyOmodiGVGHTuBbjmIpMcGOkhAle_IObOPbTAqkQYMHmINSEzvdoLLfoi64PU51d8Tec_AaJP2fd</recordid><startdate>200209</startdate><enddate>200209</enddate><creator>Toyohara, Jun</creator><creator>Hayashi, Akio</creator><creator>Sato, Mikiko</creator><creator>Tanaka, Hiromichi</creator><creator>Haraguchi, Kazuhiro</creator><creator>Yoshimura, Yuichi</creator><creator>Yonekura, Yoshiharu</creator><creator>Fujibayashi, Yasuhisa</creator><general>Society of Nuclear Medicine</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>3V.</scope><scope>4T-</scope><scope>7RV</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AF</scope><scope>8AO</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB0</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>M7Z</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>S0X</scope><scope>7X8</scope></search><sort><creationdate>200209</creationdate><title>Rationale of 5-(125)I-iodo-4'-thio-2'-deoxyuridine as a potential iodinated proliferation marker</title><author>Toyohara, Jun ; Hayashi, Akio ; Sato, Mikiko ; Tanaka, Hiromichi ; Haraguchi, Kazuhiro ; Yoshimura, Yuichi ; Yonekura, Yoshiharu ; Fujibayashi, Yasuhisa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p149t-11e03d9341d640dc973e609f94cdf1d46b7e04f00011309d7e232b77261fb4c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Animals</topic><topic>Arabinofuranosyluracil</topic><topic>Cell Division</topic><topic>Deoxyuridine - 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Academic</collection><jtitle>The Journal of nuclear medicine (1978)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Toyohara, Jun</au><au>Hayashi, Akio</au><au>Sato, Mikiko</au><au>Tanaka, Hiromichi</au><au>Haraguchi, Kazuhiro</au><au>Yoshimura, Yuichi</au><au>Yonekura, Yoshiharu</au><au>Fujibayashi, Yasuhisa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rationale of 5-(125)I-iodo-4'-thio-2'-deoxyuridine as a potential iodinated proliferation marker</atitle><jtitle>The Journal of nuclear medicine (1978)</jtitle><addtitle>J Nucl Med</addtitle><date>2002-09</date><risdate>2002</risdate><volume>43</volume><issue>9</issue><spage>1218</spage><epage>1226</epage><pages>1218-1226</pages><issn>0161-5505</issn><eissn>1535-5667</eissn><coden>JNMEAQ</coden><abstract>The aim of this investigation was to synthesize and test a novel metabolically stable iodinated nucleoside as a proliferation-imaging agent for SPECT.
5-Iodo-4'-thio-2'-deoxyuridine (ITdU) and 5-iodo-1-(4-thio-beta-D-arabinofuranosyl)uracil (ITAU) were tested. The radiolabeling of ITdU and ITAU with (125)I was achieved by a destannylation reaction of the trimethylstannyl precursor of each nucleoside. The products were isolated in high yields and with >99% radiochemical purities.
(125)I-ITdU was effectively phosphorylated by cytosolic nucleoside kinases and specifically incorporated into a thymidine kinase-expressing L-M cell rather than a thymidine kinase-deficient mutant L-M (TK(-)) cell. In addition, an in vitro cell metabolism study of (125)I-ITdU clarified that (125)I-ITdU was effectively and specifically incorporated into a DNA fraction (>90% at 60 min). Therefore, (125)I-ITdU was proven to be an ideal DNA synthesis marker such as 5-(125)I-iodo-2'-deoxyuridine (IUdR). In contrast, (125)I-ITAU was neither remarkably phosphorylated by cytosolic nucleoside kinases nor notably incorporated into an L-M cell rather than an L-M (TK(-)) cell. (125)I-ITdU and (125)I-ITAU showed a higher resistance to phosphorolytic cleavage by recombinant thymidine phosphorylase than did (125)I-IUdR. Furthermore, biodistribution of (125)I-ITdU and (125)I-ITAU revealed better in vivo stability of radioiodination than that of (125)I-IUdR. (125)I-ITdU also displayed a significantly higher uptake in proliferating organs (thymus, spleen, small intestine, and bone) than in nonproliferating organs (brain, muscle, liver, and lung), as did (125)I-IUdR, at 18 h after injection. As indicated by the in vitro study, (125)I-ITAU did not show any significant uptake in proliferating organs.
Radioiodine-labeled ITdU is potentially useful as a proliferation-imaging agent, and further studies should clarify the usefulness of this compound as a tumor-imaging agent.</abstract><cop>United States</cop><pub>Society of Nuclear Medicine</pub><pmid>12215562</pmid><tpages>9</tpages></addata></record> |
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| subjects | Animals Arabinofuranosyluracil Cell Division Deoxyuridine - analogs & derivatives Humans Iodine Radioisotopes Isotope Labeling Mice Mice, Inbred C57BL Monosaccharides Tissue Distribution Tomography, Emission-Computed, Single-Photon Uracil - analogs & derivatives Uridine |
| title | Rationale of 5-(125)I-iodo-4'-thio-2'-deoxyuridine as a potential iodinated proliferation marker |
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