Synthesis, radiolabeling, and biodistribution of putative metabolites of iodoazomycin arabinoside
Scintigraphic evaluation of patients with advanced oncological disease showed uptake of radioactivity in the brain following administration of the hypoxic imaging agent 123I-iodoazomycin arabinoside ( 123I-IAZA). Three proposed metabolites of IAZA—methyl 5-deoxy-5-iodo-D-arabinofuranoside, methyl 2,...
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| Veröffentlicht in: | Nuclear medicine and biology 2000, Vol.27 (1), p.61-68 |
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| creator | Lee, Herbert C Kumar, Piyush McEwan, Alexander J Wiebe, Leonard I Mercer, John R |
| description | Scintigraphic evaluation of patients with advanced oncological disease showed uptake of radioactivity in the brain following administration of the hypoxic imaging agent
123I-iodoazomycin arabinoside (
123I-IAZA). Three proposed metabolites of IAZA—methyl 5-deoxy-5-iodo-D-arabinofuranoside, methyl 2,3-di-
O-acetyl-5-deoxy-5-iodo-α-D-arabinofuranoside, and 1-(5-deoxy-5-iodo-α-D-arabinofuranosyl)-2-aminoimidazole (IAIA)—were synthesized, radiolabeled with
125I, and investigated in normal and tumor-bearing murine models for their contribution to this unusual phenomenon. The three compounds were readily radiolabeled by melt or solvent exchange procedures. Biodistribution data indicated rapid blood clearance, rapid excretion, and little tissue accumulation in the brain. IAIA showed significant tumor to blood ratios at 4 h (4.3:1) and liver to blood ratios at 24 h (30:1). |
| doi_str_mv | 10.1016/S0969-8051(99)00089-X |
| format | Article |
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123I-iodoazomycin arabinoside (
123I-IAZA). Three proposed metabolites of IAZA—methyl 5-deoxy-5-iodo-D-arabinofuranoside, methyl 2,3-di-
O-acetyl-5-deoxy-5-iodo-α-D-arabinofuranoside, and 1-(5-deoxy-5-iodo-α-D-arabinofuranosyl)-2-aminoimidazole (IAIA)—were synthesized, radiolabeled with
125I, and investigated in normal and tumor-bearing murine models for their contribution to this unusual phenomenon. The three compounds were readily radiolabeled by melt or solvent exchange procedures. Biodistribution data indicated rapid blood clearance, rapid excretion, and little tissue accumulation in the brain. IAIA showed significant tumor to blood ratios at 4 h (4.3:1) and liver to blood ratios at 24 h (30:1).</description><identifier>ISSN: 0969-8051</identifier><identifier>EISSN: 1872-9614</identifier><identifier>DOI: 10.1016/S0969-8051(99)00089-X</identifier><identifier>PMID: 10755647</identifier><language>eng</language><publisher>Amsterdam: Elsevier Inc</publisher><subject>Animals ; Arabinofuranosides ; Biological and medical sciences ; Hypoxia ; Injections, Intravenous ; Investigative techniques, diagnostic techniques (general aspects) ; Iodine Radioisotopes ; Iodoazomycin arabinoside ; Medical sciences ; Metabolic Clearance Rate ; Mice ; Mice, Inbred BALB C ; Neoplasms, Experimental - diagnostic imaging ; Neoplasms, Experimental - metabolism ; Nervous system ; Nitroimidazoles ; Nitroimidazoles - blood ; Nitroimidazoles - chemical synthesis ; Nitroimidazoles - chemistry ; Nitroimidazoles - pharmacokinetics ; Radioiodination ; Radionuclide Imaging ; Radionuclide investigations ; Tissue Distribution ; Tumor imaging</subject><ispartof>Nuclear medicine and biology, 2000, Vol.27 (1), p.61-68</ispartof><rights>2000 Elsevier Science Inc.</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-8f705e579ae39b6e718bb1ed812f95d4ea080969fce2f149d0d9686b4245e2203</citedby><cites>FETCH-LOGICAL-c390t-8f705e579ae39b6e718bb1ed812f95d4ea080969fce2f149d0d9686b4245e2203</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0969-8051(99)00089-X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,4024,27923,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1286059$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10755647$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Herbert C</creatorcontrib><creatorcontrib>Kumar, Piyush</creatorcontrib><creatorcontrib>McEwan, Alexander J</creatorcontrib><creatorcontrib>Wiebe, Leonard I</creatorcontrib><creatorcontrib>Mercer, John R</creatorcontrib><title>Synthesis, radiolabeling, and biodistribution of putative metabolites of iodoazomycin arabinoside</title><title>Nuclear medicine and biology</title><addtitle>Nucl Med Biol</addtitle><description>Scintigraphic evaluation of patients with advanced oncological disease showed uptake of radioactivity in the brain following administration of the hypoxic imaging agent
123I-iodoazomycin arabinoside (
123I-IAZA). Three proposed metabolites of IAZA—methyl 5-deoxy-5-iodo-D-arabinofuranoside, methyl 2,3-di-
O-acetyl-5-deoxy-5-iodo-α-D-arabinofuranoside, and 1-(5-deoxy-5-iodo-α-D-arabinofuranosyl)-2-aminoimidazole (IAIA)—were synthesized, radiolabeled with
125I, and investigated in normal and tumor-bearing murine models for their contribution to this unusual phenomenon. The three compounds were readily radiolabeled by melt or solvent exchange procedures. Biodistribution data indicated rapid blood clearance, rapid excretion, and little tissue accumulation in the brain. IAIA showed significant tumor to blood ratios at 4 h (4.3:1) and liver to blood ratios at 24 h (30:1).</description><subject>Animals</subject><subject>Arabinofuranosides</subject><subject>Biological and medical sciences</subject><subject>Hypoxia</subject><subject>Injections, Intravenous</subject><subject>Investigative techniques, diagnostic techniques (general aspects)</subject><subject>Iodine Radioisotopes</subject><subject>Iodoazomycin arabinoside</subject><subject>Medical sciences</subject><subject>Metabolic Clearance Rate</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Neoplasms, Experimental - diagnostic imaging</subject><subject>Neoplasms, Experimental - metabolism</subject><subject>Nervous system</subject><subject>Nitroimidazoles</subject><subject>Nitroimidazoles - blood</subject><subject>Nitroimidazoles - chemical synthesis</subject><subject>Nitroimidazoles - chemistry</subject><subject>Nitroimidazoles - pharmacokinetics</subject><subject>Radioiodination</subject><subject>Radionuclide Imaging</subject><subject>Radionuclide investigations</subject><subject>Tissue Distribution</subject><subject>Tumor imaging</subject><issn>0969-8051</issn><issn>1872-9614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1rFEEQhhsxmE30JyhzEFHIaPXsdM_0KUiIUQh4iEJuTX_UaMlM99rdE9j8emezi_HmqaB43vp4GHvJ4T0HLj_cgJKq7kHwt0q9A4Be1bdP2Ir3XVMrydunbPUXOWYnOf-CJddyeMaOOXRCyLZbMXOzDeUnZspnVTKe4mgsjhR-nFUm-MpS9JRLIjsXiqGKQ7WZiyl0h9WExdg4UsG86y9kNPdx2joKlUnGUoiZPD5nR4MZM7441FP2_dPlt4vP9fXXqy8XH69rt1ZQ6n7oQKDolMG1shI73lvL0fe8GZTwLRrod_8MDpuBt8qDV7KXtm1agU0D61P2Zj93k-LvGXPRE2WH42gCxjnrjsNaSJALKPagSzHnhIPeJJpM2moOeudWP7jVO3FaKf3gVt8uuVeHBbOd0P-T2stcgNcHwGRnxiGZ4Cg_ck0vQagFO99juNi4I0w6O8Lg0FNCV7SP9J9L_gBSVZfF</recordid><startdate>2000</startdate><enddate>2000</enddate><creator>Lee, Herbert C</creator><creator>Kumar, Piyush</creator><creator>McEwan, Alexander J</creator><creator>Wiebe, Leonard I</creator><creator>Mercer, John R</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>2000</creationdate><title>Synthesis, radiolabeling, and biodistribution of putative metabolites of iodoazomycin arabinoside</title><author>Lee, Herbert C ; Kumar, Piyush ; McEwan, Alexander J ; Wiebe, Leonard I ; Mercer, John R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-8f705e579ae39b6e718bb1ed812f95d4ea080969fce2f149d0d9686b4245e2203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Animals</topic><topic>Arabinofuranosides</topic><topic>Biological and medical sciences</topic><topic>Hypoxia</topic><topic>Injections, Intravenous</topic><topic>Investigative techniques, diagnostic techniques (general aspects)</topic><topic>Iodine Radioisotopes</topic><topic>Iodoazomycin arabinoside</topic><topic>Medical sciences</topic><topic>Metabolic Clearance Rate</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Neoplasms, Experimental - diagnostic imaging</topic><topic>Neoplasms, Experimental - metabolism</topic><topic>Nervous system</topic><topic>Nitroimidazoles</topic><topic>Nitroimidazoles - blood</topic><topic>Nitroimidazoles - chemical synthesis</topic><topic>Nitroimidazoles - chemistry</topic><topic>Nitroimidazoles - pharmacokinetics</topic><topic>Radioiodination</topic><topic>Radionuclide Imaging</topic><topic>Radionuclide investigations</topic><topic>Tissue Distribution</topic><topic>Tumor imaging</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Herbert C</creatorcontrib><creatorcontrib>Kumar, Piyush</creatorcontrib><creatorcontrib>McEwan, Alexander J</creatorcontrib><creatorcontrib>Wiebe, Leonard I</creatorcontrib><creatorcontrib>Mercer, John R</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Nuclear medicine and biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Herbert C</au><au>Kumar, Piyush</au><au>McEwan, Alexander J</au><au>Wiebe, Leonard I</au><au>Mercer, John R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, radiolabeling, and biodistribution of putative metabolites of iodoazomycin arabinoside</atitle><jtitle>Nuclear medicine and biology</jtitle><addtitle>Nucl Med Biol</addtitle><date>2000</date><risdate>2000</risdate><volume>27</volume><issue>1</issue><spage>61</spage><epage>68</epage><pages>61-68</pages><issn>0969-8051</issn><eissn>1872-9614</eissn><abstract>Scintigraphic evaluation of patients with advanced oncological disease showed uptake of radioactivity in the brain following administration of the hypoxic imaging agent
123I-iodoazomycin arabinoside (
123I-IAZA). Three proposed metabolites of IAZA—methyl 5-deoxy-5-iodo-D-arabinofuranoside, methyl 2,3-di-
O-acetyl-5-deoxy-5-iodo-α-D-arabinofuranoside, and 1-(5-deoxy-5-iodo-α-D-arabinofuranosyl)-2-aminoimidazole (IAIA)—were synthesized, radiolabeled with
125I, and investigated in normal and tumor-bearing murine models for their contribution to this unusual phenomenon. The three compounds were readily radiolabeled by melt or solvent exchange procedures. Biodistribution data indicated rapid blood clearance, rapid excretion, and little tissue accumulation in the brain. IAIA showed significant tumor to blood ratios at 4 h (4.3:1) and liver to blood ratios at 24 h (30:1).</abstract><cop>Amsterdam</cop><pub>Elsevier Inc</pub><pmid>10755647</pmid><doi>10.1016/S0969-8051(99)00089-X</doi><tpages>8</tpages></addata></record> |
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| subjects | Animals Arabinofuranosides Biological and medical sciences Hypoxia Injections, Intravenous Investigative techniques, diagnostic techniques (general aspects) Iodine Radioisotopes Iodoazomycin arabinoside Medical sciences Metabolic Clearance Rate Mice Mice, Inbred BALB C Neoplasms, Experimental - diagnostic imaging Neoplasms, Experimental - metabolism Nervous system Nitroimidazoles Nitroimidazoles - blood Nitroimidazoles - chemical synthesis Nitroimidazoles - chemistry Nitroimidazoles - pharmacokinetics Radioiodination Radionuclide Imaging Radionuclide investigations Tissue Distribution Tumor imaging |
| title | Synthesis, radiolabeling, and biodistribution of putative metabolites of iodoazomycin arabinoside |
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