Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 3: A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine
3-(3-[18F]Fluoropropyl)-6-nitroquipazine ([18F]FPNQ) as a 5-HT transporter imaging agents was designed, synthesized, and evaluated. FPNQ was selected due to its potent in vitro biological activity (K(i)=0.32 nM) in rat brain cortical membranes. The 18F-labeled FPNQ was prepared by reaction of the pr...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2003-11, Vol.11 (23), p.4949-4958 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | BYOUNG SE LEE SOYOUNG CHU KYO CHUL LEE LEE, Bon-Su DAE YOON CHI YEARN SEONG CHOE SANG EUN KIM YUN SEON SONG CHANGBAE JIN |
| description | 3-(3-[18F]Fluoropropyl)-6-nitroquipazine ([18F]FPNQ) as a 5-HT transporter imaging agents was designed, synthesized, and evaluated. FPNQ was selected due to its potent in vitro biological activity (K(i)=0.32 nM) in rat brain cortical membranes. The 18F-labeled FPNQ was prepared by reaction of the propyl mesylate as a precursor with tetra-n-butylammonium [18F]fluoride generated under NCA conditions. The precursor mesylate was synthesized from commercially available hydrocarbostyril in nine steps in 21% overall yield. The specific activity of the [18F]FPNQ determined by radioreceptor assay was 27.0 GBq/micromol. Tissue distribution studies in mice showed the highest uptake in the frontal cortex (5.79 %ID/g) at 60 min post-injection. |
| doi_str_mv | 10.1016/j.bmc.2003.09.009 |
| format | Article |
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The precursor mesylate was synthesized from commercially available hydrocarbostyril in nine steps in 21% overall yield. The specific activity of the [18F]FPNQ determined by radioreceptor assay was 27.0 GBq/micromol. Tissue distribution studies in mice showed the highest uptake in the frontal cortex (5.79 %ID/g) at 60 min post-injection.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2003.09.009</identifier><identifier>PMID: 14604657</identifier><language>eng</language><publisher>Oxford: Elsevier Science</publisher><subject>Animals ; Biological and medical sciences ; Carrier Proteins - chemical synthesis ; Carrier Proteins - metabolism ; Chromatography, High Pressure Liquid ; Contrast media. Radiopharmaceuticals ; Magnetic Resonance Spectroscopy ; Medical sciences ; Membrane Glycoproteins - chemical synthesis ; Membrane Glycoproteins - metabolism ; Membrane Transport Proteins ; Mice ; Nerve Tissue Proteins - chemical synthesis ; Nerve Tissue Proteins - metabolism ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pharmacology. Drug treatments ; Quipazine - analogs & derivatives ; Quipazine - chemical synthesis ; Quipazine - metabolism ; Serotonin Plasma Membrane Transport Proteins ; Serotoninergic system ; Spectrometry, Mass, Electrospray Ionization ; Spectrometry, Mass, Fast Atom Bombardment ; Tissue Distribution</subject><ispartof>Bioorganic & medicinal chemistry, 2003-11, Vol.11 (23), p.4949-4958</ispartof><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15234761$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14604657$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>BYOUNG SE LEE</creatorcontrib><creatorcontrib>SOYOUNG CHU</creatorcontrib><creatorcontrib>KYO CHUL LEE</creatorcontrib><creatorcontrib>LEE, Bon-Su</creatorcontrib><creatorcontrib>DAE YOON CHI</creatorcontrib><creatorcontrib>YEARN SEONG CHOE</creatorcontrib><creatorcontrib>SANG EUN KIM</creatorcontrib><creatorcontrib>YUN SEON SONG</creatorcontrib><creatorcontrib>CHANGBAE JIN</creatorcontrib><title>Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 3: A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>3-(3-[18F]Fluoropropyl)-6-nitroquipazine ([18F]FPNQ) as a 5-HT transporter imaging agents was designed, synthesized, and evaluated. FPNQ was selected due to its potent in vitro biological activity (K(i)=0.32 nM) in rat brain cortical membranes. The 18F-labeled FPNQ was prepared by reaction of the propyl mesylate as a precursor with tetra-n-butylammonium [18F]fluoride generated under NCA conditions. The precursor mesylate was synthesized from commercially available hydrocarbostyril in nine steps in 21% overall yield. The specific activity of the [18F]FPNQ determined by radioreceptor assay was 27.0 GBq/micromol. Tissue distribution studies in mice showed the highest uptake in the frontal cortex (5.79 %ID/g) at 60 min post-injection.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Carrier Proteins - chemical synthesis</subject><subject>Carrier Proteins - metabolism</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Contrast media. Radiopharmaceuticals</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Membrane Glycoproteins - chemical synthesis</subject><subject>Membrane Glycoproteins - metabolism</subject><subject>Membrane Transport Proteins</subject><subject>Mice</subject><subject>Nerve Tissue Proteins - chemical synthesis</subject><subject>Nerve Tissue Proteins - metabolism</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pharmacology. Drug treatments</subject><subject>Quipazine - analogs & derivatives</subject><subject>Quipazine - chemical synthesis</subject><subject>Quipazine - metabolism</subject><subject>Serotonin Plasma Membrane Transport Proteins</subject><subject>Serotoninergic system</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Tissue Distribution</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0F9LHDEQAPBQLPW0_QB9kbxYKjTr5JLNbvom4j8QFKpPpRzJbnJG9pI1yT5cP5ifz9ieKEIgmeTHzGQQ-kqhokDF4X2lV101B2AVyApAfkAzygUnjEm6hWYgRUuglWIb7aR0DwBzLukntF0QcFE3M_T4a-3znUkmYeV7rJ3vnV9iZa3zLrtyHSwWpJxjeJjcqP46bwpVQ1hO5dWGiJOJIQfvPM5R-TSGmE2s8LWKGbOf-AiPIRufnRpwTc5v3irsVmr5r-CyiB-Yke-M_Kbt6R87TCGGsaz1cEDed_AZfbRqSObLZt9Ft6cnN8fn5PLq7OL46JKMc9ZkoqVVrFG2l62BmmrO6pppylXTSoBOW0lpD6KxQuvWFtGWUPdUdpRb29RsF337n3d8Lm5SXqxc6swwKG_ClBYNZbwWrC1wbwMnvTL9YozlZ3G9eJl0AfsboFKnBltm0Ln06uo5442g7AnqJpC9</recordid><startdate>20031117</startdate><enddate>20031117</enddate><creator>BYOUNG SE LEE</creator><creator>SOYOUNG CHU</creator><creator>KYO CHUL LEE</creator><creator>LEE, Bon-Su</creator><creator>DAE YOON CHI</creator><creator>YEARN SEONG CHOE</creator><creator>SANG EUN KIM</creator><creator>YUN SEON SONG</creator><creator>CHANGBAE JIN</creator><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20031117</creationdate><title>Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 3: A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine</title><author>BYOUNG SE LEE ; SOYOUNG CHU ; KYO CHUL LEE ; LEE, Bon-Su ; DAE YOON CHI ; YEARN SEONG CHOE ; SANG EUN KIM ; YUN SEON SONG ; CHANGBAE JIN</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p237t-b9fa37afd98e051b43553b14a78900cbf911d067f6bb8f05181d0bd19c14ff753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Carrier Proteins - chemical synthesis</topic><topic>Carrier Proteins - metabolism</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Contrast media. Radiopharmaceuticals</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Membrane Glycoproteins - chemical synthesis</topic><topic>Membrane Glycoproteins - metabolism</topic><topic>Membrane Transport Proteins</topic><topic>Mice</topic><topic>Nerve Tissue Proteins - chemical synthesis</topic><topic>Nerve Tissue Proteins - metabolism</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pharmacology. Drug treatments</topic><topic>Quipazine - analogs & derivatives</topic><topic>Quipazine - chemical synthesis</topic><topic>Quipazine - metabolism</topic><topic>Serotonin Plasma Membrane Transport Proteins</topic><topic>Serotoninergic system</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Tissue Distribution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>BYOUNG SE LEE</creatorcontrib><creatorcontrib>SOYOUNG CHU</creatorcontrib><creatorcontrib>KYO CHUL LEE</creatorcontrib><creatorcontrib>LEE, Bon-Su</creatorcontrib><creatorcontrib>DAE YOON CHI</creatorcontrib><creatorcontrib>YEARN SEONG CHOE</creatorcontrib><creatorcontrib>SANG EUN KIM</creatorcontrib><creatorcontrib>YUN SEON SONG</creatorcontrib><creatorcontrib>CHANGBAE JIN</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>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>BYOUNG SE LEE</au><au>SOYOUNG CHU</au><au>KYO CHUL LEE</au><au>LEE, Bon-Su</au><au>DAE YOON CHI</au><au>YEARN SEONG CHOE</au><au>SANG EUN KIM</au><au>YUN SEON SONG</au><au>CHANGBAE JIN</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 3: A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2003-11-17</date><risdate>2003</risdate><volume>11</volume><issue>23</issue><spage>4949</spage><epage>4958</epage><pages>4949-4958</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>3-(3-[18F]Fluoropropyl)-6-nitroquipazine ([18F]FPNQ) as a 5-HT transporter imaging agents was designed, synthesized, and evaluated. FPNQ was selected due to its potent in vitro biological activity (K(i)=0.32 nM) in rat brain cortical membranes. The 18F-labeled FPNQ was prepared by reaction of the propyl mesylate as a precursor with tetra-n-butylammonium [18F]fluoride generated under NCA conditions. The precursor mesylate was synthesized from commercially available hydrocarbostyril in nine steps in 21% overall yield. 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| subjects | Animals Biological and medical sciences Carrier Proteins - chemical synthesis Carrier Proteins - metabolism Chromatography, High Pressure Liquid Contrast media. Radiopharmaceuticals Magnetic Resonance Spectroscopy Medical sciences Membrane Glycoproteins - chemical synthesis Membrane Glycoproteins - metabolism Membrane Transport Proteins Mice Nerve Tissue Proteins - chemical synthesis Nerve Tissue Proteins - metabolism Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pharmacology. Drug treatments Quipazine - analogs & derivatives Quipazine - chemical synthesis Quipazine - metabolism Serotonin Plasma Membrane Transport Proteins Serotoninergic system Spectrometry, Mass, Electrospray Ionization Spectrometry, Mass, Fast Atom Bombardment Tissue Distribution |
| title | Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 3: A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine |
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