Technetium-99m-Labeled Long Chain Fatty Acid Analogues Metabolized by β-Oxidation in the Heart
The development of 99mTc-labeled fatty acid analogues metabolized by β-oxidation in the myocardium constitutes an unsolved challenge. On the basis of our recent findings that [188Re]tricarbonyl(cyclopentadienylcarbonate)rhenium ([188Re]CpTR-COOH) was recognized as an aromatic compound and was metabo...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 2007-02, Vol.50 (3), p.543-549 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 549 |
|---|---|
| container_issue | 3 |
| container_start_page | 543 |
| container_title | Journal of medicinal chemistry |
| container_volume | 50 |
| creator | Uehara, Tomoya Uemura, Tomoe Hirabayashi, Seiji Adachi, Sayaka Odaka, Kenichi Akizawa, Hiromichi Magata, Yasuhiro Irie, Toshiaki Arano, Yasushi |
| description | The development of 99mTc-labeled fatty acid analogues metabolized by β-oxidation in the myocardium constitutes an unsolved challenge. On the basis of our recent findings that [188Re]tricarbonyl(cyclopentadienylcarbonate)rhenium ([188Re]CpTR-COOH) was recognized as an aromatic compound and was metabolized as such in the body, [99mTc]cyclopentadienyltricarbonyltechnetium ([99mTc]CpTT) was conjugated at the ω-position of pentadecanoic acid to prepare [99mTc]CpTT-PA. When injected into rats, [99mTc]CpTT-PA exhibited the maximum myocardial accumulation and heart-to-blood ratio of 3.85 %ID/g at 1 min and 4.60 at 10 min postinjection, respectively. The metabolic study using isolated Langendorff perfused rat hearts demonstrated that approximately 67% of perfused [99mTc]CpTT-PA was incorporated and [99mTc]CpTT-propionic acid, the metabolite after six cycles of β-oxidation of [99mTc]CpTT-PA, was detected as the major radiometabolite in the perfusate and myocardium. These findings indicate that [99mTc]CpTT-PA was recognized, transported, and metabolized as a long chain fatty acid analogue for energy production in the myocardium. |
| doi_str_mv | 10.1021/jm061017g |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68963149</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68963149</sourcerecordid><originalsourceid>FETCH-LOGICAL-a425t-38138ad83f72a256dec218708fa11d72467bff8a8d2d213e26ef6fa309dc36e43</originalsourceid><addsrcrecordid>eNpt0M1u1DAQB3ALUdGlcOAFUC4gcUixx4njHJeF0qKgIrGcrYk_dr3ko9iO1OWxeJA-E0G76l44zWF-89foT8grRi8ZBfZ-11PBKKs2T8iClUDzQtLiKVlQCpCDAH5Onse4o5RyBvwZOWcVCAFULIhaW70dbPJTn9d1nzfY2s6arBmHTbbaoh-yK0xpny21N9lywG7cTDZmX23Cduz879m2--zhT3577w0mPw7ZfJO2Nru2GNILcuawi_blcV6QH1ef1qvrvLn9fLNaNjkWUKacS8YlGsldBQilMFYDkxWVDhkzFRSiap2TKA0YYNyCsE445LQ2mgtb8Avy9pB7F8Zf84NJ9T5q23U42HGKSshacFbUM3x3gDqMMQbr1F3wPYa9YlT9a1M9tjnb18fQqe2tOcljfTN4cwQYNXYu4KB9PDlZAitLOrv84HxM9v5xj-GnEhWvSrX-9l01q-YLfPjYqOqUizqq3TiFuff4nwf_AkdHlsU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68963149</pqid></control><display><type>article</type><title>Technetium-99m-Labeled Long Chain Fatty Acid Analogues Metabolized by β-Oxidation in the Heart</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Uehara, Tomoya ; Uemura, Tomoe ; Hirabayashi, Seiji ; Adachi, Sayaka ; Odaka, Kenichi ; Akizawa, Hiromichi ; Magata, Yasuhiro ; Irie, Toshiaki ; Arano, Yasushi</creator><creatorcontrib>Uehara, Tomoya ; Uemura, Tomoe ; Hirabayashi, Seiji ; Adachi, Sayaka ; Odaka, Kenichi ; Akizawa, Hiromichi ; Magata, Yasuhiro ; Irie, Toshiaki ; Arano, Yasushi</creatorcontrib><description>The development of 99mTc-labeled fatty acid analogues metabolized by β-oxidation in the myocardium constitutes an unsolved challenge. On the basis of our recent findings that [188Re]tricarbonyl(cyclopentadienylcarbonate)rhenium ([188Re]CpTR-COOH) was recognized as an aromatic compound and was metabolized as such in the body, [99mTc]cyclopentadienyltricarbonyltechnetium ([99mTc]CpTT) was conjugated at the ω-position of pentadecanoic acid to prepare [99mTc]CpTT-PA. When injected into rats, [99mTc]CpTT-PA exhibited the maximum myocardial accumulation and heart-to-blood ratio of 3.85 %ID/g at 1 min and 4.60 at 10 min postinjection, respectively. The metabolic study using isolated Langendorff perfused rat hearts demonstrated that approximately 67% of perfused [99mTc]CpTT-PA was incorporated and [99mTc]CpTT-propionic acid, the metabolite after six cycles of β-oxidation of [99mTc]CpTT-PA, was detected as the major radiometabolite in the perfusate and myocardium. These findings indicate that [99mTc]CpTT-PA was recognized, transported, and metabolized as a long chain fatty acid analogue for energy production in the myocardium.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm061017g</identifier><identifier>PMID: 17266206</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Biological and medical sciences ; Biological Transport ; Contrast media. Radiopharmaceuticals ; Energy Metabolism ; Fatty Acids - chemistry ; In Vitro Techniques ; Iodobenzenes - pharmacokinetics ; Medical sciences ; Myocardium - metabolism ; Organotechnetium Compounds - chemical synthesis ; Organotechnetium Compounds - chemistry ; Organotechnetium Compounds - pharmacokinetics ; Oxidation-Reduction ; Pharmacology. Drug treatments ; Rats ; Technetium ; Tissue Distribution</subject><ispartof>Journal of medicinal chemistry, 2007-02, Vol.50 (3), p.543-549</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a425t-38138ad83f72a256dec218708fa11d72467bff8a8d2d213e26ef6fa309dc36e43</citedby><cites>FETCH-LOGICAL-a425t-38138ad83f72a256dec218708fa11d72467bff8a8d2d213e26ef6fa309dc36e43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm061017g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm061017g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18521550$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17266206$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Uehara, Tomoya</creatorcontrib><creatorcontrib>Uemura, Tomoe</creatorcontrib><creatorcontrib>Hirabayashi, Seiji</creatorcontrib><creatorcontrib>Adachi, Sayaka</creatorcontrib><creatorcontrib>Odaka, Kenichi</creatorcontrib><creatorcontrib>Akizawa, Hiromichi</creatorcontrib><creatorcontrib>Magata, Yasuhiro</creatorcontrib><creatorcontrib>Irie, Toshiaki</creatorcontrib><creatorcontrib>Arano, Yasushi</creatorcontrib><title>Technetium-99m-Labeled Long Chain Fatty Acid Analogues Metabolized by β-Oxidation in the Heart</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The development of 99mTc-labeled fatty acid analogues metabolized by β-oxidation in the myocardium constitutes an unsolved challenge. On the basis of our recent findings that [188Re]tricarbonyl(cyclopentadienylcarbonate)rhenium ([188Re]CpTR-COOH) was recognized as an aromatic compound and was metabolized as such in the body, [99mTc]cyclopentadienyltricarbonyltechnetium ([99mTc]CpTT) was conjugated at the ω-position of pentadecanoic acid to prepare [99mTc]CpTT-PA. When injected into rats, [99mTc]CpTT-PA exhibited the maximum myocardial accumulation and heart-to-blood ratio of 3.85 %ID/g at 1 min and 4.60 at 10 min postinjection, respectively. The metabolic study using isolated Langendorff perfused rat hearts demonstrated that approximately 67% of perfused [99mTc]CpTT-PA was incorporated and [99mTc]CpTT-propionic acid, the metabolite after six cycles of β-oxidation of [99mTc]CpTT-PA, was detected as the major radiometabolite in the perfusate and myocardium. These findings indicate that [99mTc]CpTT-PA was recognized, transported, and metabolized as a long chain fatty acid analogue for energy production in the myocardium.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Biological Transport</subject><subject>Contrast media. Radiopharmaceuticals</subject><subject>Energy Metabolism</subject><subject>Fatty Acids - chemistry</subject><subject>In Vitro Techniques</subject><subject>Iodobenzenes - pharmacokinetics</subject><subject>Medical sciences</subject><subject>Myocardium - metabolism</subject><subject>Organotechnetium Compounds - chemical synthesis</subject><subject>Organotechnetium Compounds - chemistry</subject><subject>Organotechnetium Compounds - pharmacokinetics</subject><subject>Oxidation-Reduction</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Technetium</subject><subject>Tissue Distribution</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M1u1DAQB3ALUdGlcOAFUC4gcUixx4njHJeF0qKgIrGcrYk_dr3ko9iO1OWxeJA-E0G76l44zWF-89foT8grRi8ZBfZ-11PBKKs2T8iClUDzQtLiKVlQCpCDAH5Onse4o5RyBvwZOWcVCAFULIhaW70dbPJTn9d1nzfY2s6arBmHTbbaoh-yK0xpny21N9lywG7cTDZmX23Cduz879m2--zhT3577w0mPw7ZfJO2Nru2GNILcuawi_blcV6QH1ef1qvrvLn9fLNaNjkWUKacS8YlGsldBQilMFYDkxWVDhkzFRSiap2TKA0YYNyCsE445LQ2mgtb8Avy9pB7F8Zf84NJ9T5q23U42HGKSshacFbUM3x3gDqMMQbr1F3wPYa9YlT9a1M9tjnb18fQqe2tOcljfTN4cwQYNXYu4KB9PDlZAitLOrv84HxM9v5xj-GnEhWvSrX-9l01q-YLfPjYqOqUizqq3TiFuff4nwf_AkdHlsU</recordid><startdate>20070208</startdate><enddate>20070208</enddate><creator>Uehara, Tomoya</creator><creator>Uemura, Tomoe</creator><creator>Hirabayashi, Seiji</creator><creator>Adachi, Sayaka</creator><creator>Odaka, Kenichi</creator><creator>Akizawa, Hiromichi</creator><creator>Magata, Yasuhiro</creator><creator>Irie, Toshiaki</creator><creator>Arano, Yasushi</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20070208</creationdate><title>Technetium-99m-Labeled Long Chain Fatty Acid Analogues Metabolized by β-Oxidation in the Heart</title><author>Uehara, Tomoya ; Uemura, Tomoe ; Hirabayashi, Seiji ; Adachi, Sayaka ; Odaka, Kenichi ; Akizawa, Hiromichi ; Magata, Yasuhiro ; Irie, Toshiaki ; Arano, Yasushi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a425t-38138ad83f72a256dec218708fa11d72467bff8a8d2d213e26ef6fa309dc36e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Biological Transport</topic><topic>Contrast media. Radiopharmaceuticals</topic><topic>Energy Metabolism</topic><topic>Fatty Acids - chemistry</topic><topic>In Vitro Techniques</topic><topic>Iodobenzenes - pharmacokinetics</topic><topic>Medical sciences</topic><topic>Myocardium - metabolism</topic><topic>Organotechnetium Compounds - chemical synthesis</topic><topic>Organotechnetium Compounds - chemistry</topic><topic>Organotechnetium Compounds - pharmacokinetics</topic><topic>Oxidation-Reduction</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Technetium</topic><topic>Tissue Distribution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uehara, Tomoya</creatorcontrib><creatorcontrib>Uemura, Tomoe</creatorcontrib><creatorcontrib>Hirabayashi, Seiji</creatorcontrib><creatorcontrib>Adachi, Sayaka</creatorcontrib><creatorcontrib>Odaka, Kenichi</creatorcontrib><creatorcontrib>Akizawa, Hiromichi</creatorcontrib><creatorcontrib>Magata, Yasuhiro</creatorcontrib><creatorcontrib>Irie, Toshiaki</creatorcontrib><creatorcontrib>Arano, Yasushi</creatorcontrib><collection>Istex</collection><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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uehara, Tomoya</au><au>Uemura, Tomoe</au><au>Hirabayashi, Seiji</au><au>Adachi, Sayaka</au><au>Odaka, Kenichi</au><au>Akizawa, Hiromichi</au><au>Magata, Yasuhiro</au><au>Irie, Toshiaki</au><au>Arano, Yasushi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Technetium-99m-Labeled Long Chain Fatty Acid Analogues Metabolized by β-Oxidation in the Heart</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2007-02-08</date><risdate>2007</risdate><volume>50</volume><issue>3</issue><spage>543</spage><epage>549</epage><pages>543-549</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The development of 99mTc-labeled fatty acid analogues metabolized by β-oxidation in the myocardium constitutes an unsolved challenge. On the basis of our recent findings that [188Re]tricarbonyl(cyclopentadienylcarbonate)rhenium ([188Re]CpTR-COOH) was recognized as an aromatic compound and was metabolized as such in the body, [99mTc]cyclopentadienyltricarbonyltechnetium ([99mTc]CpTT) was conjugated at the ω-position of pentadecanoic acid to prepare [99mTc]CpTT-PA. When injected into rats, [99mTc]CpTT-PA exhibited the maximum myocardial accumulation and heart-to-blood ratio of 3.85 %ID/g at 1 min and 4.60 at 10 min postinjection, respectively. The metabolic study using isolated Langendorff perfused rat hearts demonstrated that approximately 67% of perfused [99mTc]CpTT-PA was incorporated and [99mTc]CpTT-propionic acid, the metabolite after six cycles of β-oxidation of [99mTc]CpTT-PA, was detected as the major radiometabolite in the perfusate and myocardium. These findings indicate that [99mTc]CpTT-PA was recognized, transported, and metabolized as a long chain fatty acid analogue for energy production in the myocardium.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17266206</pmid><doi>10.1021/jm061017g</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2007-02, Vol.50 (3), p.543-549 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68963149 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Biological and medical sciences Biological Transport Contrast media. Radiopharmaceuticals Energy Metabolism Fatty Acids - chemistry In Vitro Techniques Iodobenzenes - pharmacokinetics Medical sciences Myocardium - metabolism Organotechnetium Compounds - chemical synthesis Organotechnetium Compounds - chemistry Organotechnetium Compounds - pharmacokinetics Oxidation-Reduction Pharmacology. Drug treatments Rats Technetium Tissue Distribution |
| title | Technetium-99m-Labeled Long Chain Fatty Acid Analogues Metabolized by β-Oxidation in the Heart |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T18%3A32%3A00IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Technetium-99m-Labeled%20Long%20Chain%20Fatty%20Acid%20Analogues%20Metabolized%20by%20%CE%B2-Oxidation%20in%20the%20Heart&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Uehara,%20Tomoya&rft.date=2007-02-08&rft.volume=50&rft.issue=3&rft.spage=543&rft.epage=549&rft.pages=543-549&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm061017g&rft_dat=%3Cproquest_cross%3E68963149%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=68963149&rft_id=info:pmid/17266206&rfr_iscdi=true |