A new single-photon emission computed tomography (SPECT) imaging agent for serotonin transporters: [125I]Flip-IDAM, (2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol
New ligands for in vivo brain imaging of serotonin transporter (SERT) with single photon emission tomography (SPECT) were prepared and evaluated. An efficient synthesis and radiolabeling of a biphenylthiol, FLIP-IDAM, 4, was accomplished. The affinity of FLIP-IDAM was evaluated by an in vitro inhibi...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-02, Vol.23 (3), p.869-872 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 872 |
|---|---|
| container_issue | 3 |
| container_start_page | 869 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 23 |
| creator | Zheng, Pinguan Lieberman, Brian P. Ploessl, Karl Lemoine, Laetitia Miller, Sara Kung, Hank F. |
| description | New ligands for in vivo brain imaging of serotonin transporter (SERT) with single photon emission tomography (SPECT) were prepared and evaluated. An efficient synthesis and radiolabeling of a biphenylthiol, FLIP-IDAM, 4, was accomplished. The affinity of FLIP-IDAM was evaluated by an in vitro inhibitory binding assay using [125I]-IDAM as radioligand in rat brain tissue homogenates (Ki=0.03nM). New [125I]Flip-IDAM exhibited excellent binding affinity to SERT binding sites with a high hypothalamus to cerebellum ratio of 4 at 30min post iv injection. The faster in vivo kinetics for brain uptake and a rapid washout from non-specific regions provide excellent signal to noise ratio. This new agent, when labeled with 123I, may be a useful imaging agent for mapping SERT binding sites in the human brain. |
| doi_str_mv | 10.1016/j.bmcl.2012.11.043 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1285102658</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X12014953</els_id><sourcerecordid>1285102658</sourcerecordid><originalsourceid>FETCH-LOGICAL-c413t-b01fde0dd260d161d5ac4e3fcabbe9c8d234d6ba2cbccc1eda0509f310ec82383</originalsourceid><addsrcrecordid>eNqNkV2LEzEUhoMobq3-AS80ly04NV8zTsWbUne1sKKwuyCIhExypk2ZScYkVfq__IFmbPVSvAg5gec9hPdB6CklC0po9XK_aHrdLRihbEHpggh-D02oqETBBSnvowlZVqSol-LzBXoU454QKogQD9EF46wq65pM0M8VdvADR-u2HRTDzifvMPQ2RpsH7fvhkMDg5Hu_DWrYHfHs5tPl-naOba-2OYXVFlzCrQ84Qhjj1uEUlIuDDwlCfI2_UFZuvl51dig2b1cfXuAZK2a_j7E9pN2xU711fn6a54UorDd-2IHLr7Szfn6eR0A53z1GD1rVRXhyvqfo7urydv2-uP74brNeXRdaUJ6KhtDWADGGVcTQippSaQG81appYKlrw7gwVaOYbrTWFIwiJVm2nBLQNeM1n6LZae8Q_LcDxCRzMRq6Tjnwhygpq0tKxir_A33FyywqS5oidkJ18DEGaOUQcpnhKCmRo1i5l6NYOYqVlMqcyaFn5_2HpgfzN_LHZAaen4BWeam2wUZ5d5M3lNk6pxWrMvHmRECu7LuFIKO24DQYG0Anabz91w9-ARq1v1s</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1273501204</pqid></control><display><type>article</type><title>A new single-photon emission computed tomography (SPECT) imaging agent for serotonin transporters: [125I]Flip-IDAM, (2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Zheng, Pinguan ; Lieberman, Brian P. ; Ploessl, Karl ; Lemoine, Laetitia ; Miller, Sara ; Kung, Hank F.</creator><creatorcontrib>Zheng, Pinguan ; Lieberman, Brian P. ; Ploessl, Karl ; Lemoine, Laetitia ; Miller, Sara ; Kung, Hank F.</creatorcontrib><description>New ligands for in vivo brain imaging of serotonin transporter (SERT) with single photon emission tomography (SPECT) were prepared and evaluated. An efficient synthesis and radiolabeling of a biphenylthiol, FLIP-IDAM, 4, was accomplished. The affinity of FLIP-IDAM was evaluated by an in vitro inhibitory binding assay using [125I]-IDAM as radioligand in rat brain tissue homogenates (Ki=0.03nM). New [125I]Flip-IDAM exhibited excellent binding affinity to SERT binding sites with a high hypothalamus to cerebellum ratio of 4 at 30min post iv injection. The faster in vivo kinetics for brain uptake and a rapid washout from non-specific regions provide excellent signal to noise ratio. This new agent, when labeled with 123I, may be a useful imaging agent for mapping SERT binding sites in the human brain.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.11.043</identifier><identifier>PMID: 23265880</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Benzylamines - chemical synthesis ; Benzylamines - chemistry ; binding capacity ; binding sites ; Brain ; Brain mapping ; Cerebellum ; Chromatography, High Pressure Liquid ; Computed tomography ; Diphenyl sulfide ; humans ; hypothalamus ; image analysis ; intravenous injection ; Iodine Radioisotopes - chemistry ; Kinetics ; methanol ; Molecular Structure ; Neuroimaging ; Protein Binding ; Radioisotopes ; radiolabeling ; Radiopharmaceuticals - chemistry ; Rats ; serotonin ; Serotonin Plasma Membrane Transport Proteins - chemistry ; Serotonin transporter ; Single photon emission computed tomography ; SPECT ; Sulfides - chemical synthesis ; Sulfides - chemistry ; Tomography, Emission-Computed, Single-Photon ; transporters</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-02, Vol.23 (3), p.869-872</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c413t-b01fde0dd260d161d5ac4e3fcabbe9c8d234d6ba2cbccc1eda0509f310ec82383</citedby><cites>FETCH-LOGICAL-c413t-b01fde0dd260d161d5ac4e3fcabbe9c8d234d6ba2cbccc1eda0509f310ec82383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2012.11.043$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23265880$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zheng, Pinguan</creatorcontrib><creatorcontrib>Lieberman, Brian P.</creatorcontrib><creatorcontrib>Ploessl, Karl</creatorcontrib><creatorcontrib>Lemoine, Laetitia</creatorcontrib><creatorcontrib>Miller, Sara</creatorcontrib><creatorcontrib>Kung, Hank F.</creatorcontrib><title>A new single-photon emission computed tomography (SPECT) imaging agent for serotonin transporters: [125I]Flip-IDAM, (2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>New ligands for in vivo brain imaging of serotonin transporter (SERT) with single photon emission tomography (SPECT) were prepared and evaluated. An efficient synthesis and radiolabeling of a biphenylthiol, FLIP-IDAM, 4, was accomplished. The affinity of FLIP-IDAM was evaluated by an in vitro inhibitory binding assay using [125I]-IDAM as radioligand in rat brain tissue homogenates (Ki=0.03nM). New [125I]Flip-IDAM exhibited excellent binding affinity to SERT binding sites with a high hypothalamus to cerebellum ratio of 4 at 30min post iv injection. The faster in vivo kinetics for brain uptake and a rapid washout from non-specific regions provide excellent signal to noise ratio. This new agent, when labeled with 123I, may be a useful imaging agent for mapping SERT binding sites in the human brain.</description><subject>Animals</subject><subject>Benzylamines - chemical synthesis</subject><subject>Benzylamines - chemistry</subject><subject>binding capacity</subject><subject>binding sites</subject><subject>Brain</subject><subject>Brain mapping</subject><subject>Cerebellum</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Computed tomography</subject><subject>Diphenyl sulfide</subject><subject>humans</subject><subject>hypothalamus</subject><subject>image analysis</subject><subject>intravenous injection</subject><subject>Iodine Radioisotopes - chemistry</subject><subject>Kinetics</subject><subject>methanol</subject><subject>Molecular Structure</subject><subject>Neuroimaging</subject><subject>Protein Binding</subject><subject>Radioisotopes</subject><subject>radiolabeling</subject><subject>Radiopharmaceuticals - chemistry</subject><subject>Rats</subject><subject>serotonin</subject><subject>Serotonin Plasma Membrane Transport Proteins - chemistry</subject><subject>Serotonin transporter</subject><subject>Single photon emission computed tomography</subject><subject>SPECT</subject><subject>Sulfides - chemical synthesis</subject><subject>Sulfides - chemistry</subject><subject>Tomography, Emission-Computed, Single-Photon</subject><subject>transporters</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkV2LEzEUhoMobq3-AS80ly04NV8zTsWbUne1sKKwuyCIhExypk2ZScYkVfq__IFmbPVSvAg5gec9hPdB6CklC0po9XK_aHrdLRihbEHpggh-D02oqETBBSnvowlZVqSol-LzBXoU454QKogQD9EF46wq65pM0M8VdvADR-u2HRTDzifvMPQ2RpsH7fvhkMDg5Hu_DWrYHfHs5tPl-naOba-2OYXVFlzCrQ84Qhjj1uEUlIuDDwlCfI2_UFZuvl51dig2b1cfXuAZK2a_j7E9pN2xU711fn6a54UorDd-2IHLr7Szfn6eR0A53z1GD1rVRXhyvqfo7urydv2-uP74brNeXRdaUJ6KhtDWADGGVcTQippSaQG81appYKlrw7gwVaOYbrTWFIwiJVm2nBLQNeM1n6LZae8Q_LcDxCRzMRq6Tjnwhygpq0tKxir_A33FyywqS5oidkJ18DEGaOUQcpnhKCmRo1i5l6NYOYqVlMqcyaFn5_2HpgfzN_LHZAaen4BWeam2wUZ5d5M3lNk6pxWrMvHmRECu7LuFIKO24DQYG0Anabz91w9-ARq1v1s</recordid><startdate>20130201</startdate><enddate>20130201</enddate><creator>Zheng, Pinguan</creator><creator>Lieberman, Brian P.</creator><creator>Ploessl, Karl</creator><creator>Lemoine, Laetitia</creator><creator>Miller, Sara</creator><creator>Kung, Hank F.</creator><general>Elsevier Ltd</general><scope>FBQ</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20130201</creationdate><title>A new single-photon emission computed tomography (SPECT) imaging agent for serotonin transporters: [125I]Flip-IDAM, (2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol</title><author>Zheng, Pinguan ; Lieberman, Brian P. ; Ploessl, Karl ; Lemoine, Laetitia ; Miller, Sara ; Kung, Hank F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c413t-b01fde0dd260d161d5ac4e3fcabbe9c8d234d6ba2cbccc1eda0509f310ec82383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Animals</topic><topic>Benzylamines - chemical synthesis</topic><topic>Benzylamines - chemistry</topic><topic>binding capacity</topic><topic>binding sites</topic><topic>Brain</topic><topic>Brain mapping</topic><topic>Cerebellum</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Computed tomography</topic><topic>Diphenyl sulfide</topic><topic>humans</topic><topic>hypothalamus</topic><topic>image analysis</topic><topic>intravenous injection</topic><topic>Iodine Radioisotopes - chemistry</topic><topic>Kinetics</topic><topic>methanol</topic><topic>Molecular Structure</topic><topic>Neuroimaging</topic><topic>Protein Binding</topic><topic>Radioisotopes</topic><topic>radiolabeling</topic><topic>Radiopharmaceuticals - chemistry</topic><topic>Rats</topic><topic>serotonin</topic><topic>Serotonin Plasma Membrane Transport Proteins - chemistry</topic><topic>Serotonin transporter</topic><topic>Single photon emission computed tomography</topic><topic>SPECT</topic><topic>Sulfides - chemical synthesis</topic><topic>Sulfides - chemistry</topic><topic>Tomography, Emission-Computed, Single-Photon</topic><topic>transporters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Pinguan</creatorcontrib><creatorcontrib>Lieberman, Brian P.</creatorcontrib><creatorcontrib>Ploessl, Karl</creatorcontrib><creatorcontrib>Lemoine, Laetitia</creatorcontrib><creatorcontrib>Miller, Sara</creatorcontrib><creatorcontrib>Kung, Hank F.</creatorcontrib><collection>AGRIS</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zheng, Pinguan</au><au>Lieberman, Brian P.</au><au>Ploessl, Karl</au><au>Lemoine, Laetitia</au><au>Miller, Sara</au><au>Kung, Hank F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new single-photon emission computed tomography (SPECT) imaging agent for serotonin transporters: [125I]Flip-IDAM, (2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-02-01</date><risdate>2013</risdate><volume>23</volume><issue>3</issue><spage>869</spage><epage>872</epage><pages>869-872</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>New ligands for in vivo brain imaging of serotonin transporter (SERT) with single photon emission tomography (SPECT) were prepared and evaluated. An efficient synthesis and radiolabeling of a biphenylthiol, FLIP-IDAM, 4, was accomplished. The affinity of FLIP-IDAM was evaluated by an in vitro inhibitory binding assay using [125I]-IDAM as radioligand in rat brain tissue homogenates (Ki=0.03nM). New [125I]Flip-IDAM exhibited excellent binding affinity to SERT binding sites with a high hypothalamus to cerebellum ratio of 4 at 30min post iv injection. The faster in vivo kinetics for brain uptake and a rapid washout from non-specific regions provide excellent signal to noise ratio. This new agent, when labeled with 123I, may be a useful imaging agent for mapping SERT binding sites in the human brain.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>23265880</pmid><doi>10.1016/j.bmcl.2012.11.043</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2013-02, Vol.23 (3), p.869-872 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1285102658 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Animals Benzylamines - chemical synthesis Benzylamines - chemistry binding capacity binding sites Brain Brain mapping Cerebellum Chromatography, High Pressure Liquid Computed tomography Diphenyl sulfide humans hypothalamus image analysis intravenous injection Iodine Radioisotopes - chemistry Kinetics methanol Molecular Structure Neuroimaging Protein Binding Radioisotopes radiolabeling Radiopharmaceuticals - chemistry Rats serotonin Serotonin Plasma Membrane Transport Proteins - chemistry Serotonin transporter Single photon emission computed tomography SPECT Sulfides - chemical synthesis Sulfides - chemistry Tomography, Emission-Computed, Single-Photon transporters |
| title | A new single-photon emission computed tomography (SPECT) imaging agent for serotonin transporters: [125I]Flip-IDAM, (2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T22%3A53%3A03IST&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=A%20new%20single-photon%20emission%20computed%20tomography%20(SPECT)%20imaging%20agent%20for%20serotonin%20transporters:%20%5B125I%5DFlip-IDAM,%20(2-((2-((dimethylamino)methyl)-4-iodophenyl)thio)phenyl)methanol&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Zheng,%20Pinguan&rft.date=2013-02-01&rft.volume=23&rft.issue=3&rft.spage=869&rft.epage=872&rft.pages=869-872&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2012.11.043&rft_dat=%3Cproquest_cross%3E1285102658%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=1273501204&rft_id=info:pmid/23265880&rft_els_id=S0960894X12014953&rfr_iscdi=true |