Synthesis and in vitro evaluation of novel derivatives of diphenylsulfide as serotonin transporter ligands
A series of diphenylsulfide derivatives was prepared and their binding affinities for monoamine transporters (SERT, DAT, and NET) are reported. As the serotonin transporter (SERT) is involved in several neurodegenerative and psychiatric disorders, radiopharmaceuticals to image the SERT by PET or SPE...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-03, Vol.16 (5), p.1297-1300 |
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| creator | Vercouillie, Johnny Mavel, Sylvie Galineau, Laurent Ragusa, Tiziana Innis, Robert Kassiou, Michael Chalon, Sylvie Dollé, Frédéric Besnard, Jean-Claude Guilloteau, Denis Emond, Patrick |
| description | A series of diphenylsulfide derivatives was prepared and their binding affinities for monoamine transporters (SERT, DAT, and NET) are reported.
As the serotonin transporter (SERT) is involved in several neurodegenerative and psychiatric disorders, radiopharmaceuticals to image the SERT by PET or SPECT would be very valuable in studying these diseases. For the development of imaging agents, we have synthesized novel derivatives of recently reported diphenylsulfide SERT ligands, in which the sulfur atom linking the two phenyl rings was replaced by an oxygen, sulfinyl, sulfonyl, amino or carbon group. Three of these exhibited good to high in vitro affinity (0.5
nM
<
K
i
<
11
nM) and selectivity for the SERT over the other monoamine transporters. |
| doi_str_mv | 10.1016/j.bmcl.2005.11.066 |
| format | Article |
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As the serotonin transporter (SERT) is involved in several neurodegenerative and psychiatric disorders, radiopharmaceuticals to image the SERT by PET or SPECT would be very valuable in studying these diseases. For the development of imaging agents, we have synthesized novel derivatives of recently reported diphenylsulfide SERT ligands, in which the sulfur atom linking the two phenyl rings was replaced by an oxygen, sulfinyl, sulfonyl, amino or carbon group. Three of these exhibited good to high in vitro affinity (0.5
nM
<
K
i
<
11
nM) and selectivity for the SERT over the other monoamine transporters.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.11.066</identifier><identifier>PMID: 16337793</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Biological and medical sciences ; Diphenylsulfide derivatives ; Inhibitory Concentration 50 ; Ligands ; MADAM derivatives ; Medical sciences ; Molecular Structure ; Monoamine transporters ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pharmacology. Drug treatments ; Sensitivity and Specificity ; Serotonin Plasma Membrane Transport Proteins - metabolism ; Serotoninergic system ; SERT ; Structure-Activity Relationship ; Substrate Specificity ; Sulfides - chemical synthesis ; Sulfides - chemistry ; Sulfides - metabolism</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-03, Vol.16 (5), p.1297-1300</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-25d83247a7a7c933d43c9e09f9f018cfb8a57d01c0b09b08ad8d12a35f4dc96d3</citedby><cites>FETCH-LOGICAL-c415t-25d83247a7a7c933d43c9e09f9f018cfb8a57d01c0b09b08ad8d12a35f4dc96d3</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.2005.11.066$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17557276$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16337793$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vercouillie, Johnny</creatorcontrib><creatorcontrib>Mavel, Sylvie</creatorcontrib><creatorcontrib>Galineau, Laurent</creatorcontrib><creatorcontrib>Ragusa, Tiziana</creatorcontrib><creatorcontrib>Innis, Robert</creatorcontrib><creatorcontrib>Kassiou, Michael</creatorcontrib><creatorcontrib>Chalon, Sylvie</creatorcontrib><creatorcontrib>Dollé, Frédéric</creatorcontrib><creatorcontrib>Besnard, Jean-Claude</creatorcontrib><creatorcontrib>Guilloteau, Denis</creatorcontrib><creatorcontrib>Emond, Patrick</creatorcontrib><title>Synthesis and in vitro evaluation of novel derivatives of diphenylsulfide as serotonin transporter ligands</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of diphenylsulfide derivatives was prepared and their binding affinities for monoamine transporters (SERT, DAT, and NET) are reported.
As the serotonin transporter (SERT) is involved in several neurodegenerative and psychiatric disorders, radiopharmaceuticals to image the SERT by PET or SPECT would be very valuable in studying these diseases. For the development of imaging agents, we have synthesized novel derivatives of recently reported diphenylsulfide SERT ligands, in which the sulfur atom linking the two phenyl rings was replaced by an oxygen, sulfinyl, sulfonyl, amino or carbon group. Three of these exhibited good to high in vitro affinity (0.5
nM
<
K
i
<
11
nM) and selectivity for the SERT over the other monoamine transporters.</description><subject>Biological and medical sciences</subject><subject>Diphenylsulfide derivatives</subject><subject>Inhibitory Concentration 50</subject><subject>Ligands</subject><subject>MADAM derivatives</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Monoamine transporters</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pharmacology. Drug treatments</subject><subject>Sensitivity and Specificity</subject><subject>Serotonin Plasma Membrane Transport Proteins - metabolism</subject><subject>Serotoninergic system</subject><subject>SERT</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><subject>Sulfides - chemical synthesis</subject><subject>Sulfides - chemistry</subject><subject>Sulfides - metabolism</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2LFDEQQIMo7rj6BzxILnqbNumkOx3wIotfsOBBBW8hnVS7GTLJmOpumH9vmhnYm-RQULx6hEfIa84aznj__tCMRxeblrGu4bxhff-E7Ljs5V5I1j0lO6Z7th-0_H1DXiAeGOOSSfmc3PBeCKW02JHDj3OaHwADUps8DYmuYS6ZwmrjYueQE80TTXmFSD2UsNbdCrgtfTg9QDpHXOIUPFCLFKHkOadqmYtNeMplhkJj-FPd-JI8m2xEeHWdt-TX508_777u779_-Xb38X7vJO_mfdv5QbRS2fqcFsJL4TQwPemJ8cFN42A75Rl3bGR6ZIP1g-etFd0kvdO9F7fk3cV7KvnvAjibY0AHMdoEeUHDFVNSD6qC7QV0JSMWmMyphKMtZ8OZ2Qqbg9kKm62w4dzUwvXozdW-jEfwjyfXpBV4ewUsOhunGsIFfORU16lWbaIPFw5qizVAMegCJAc-FHCz8Tn87x__AFOanF4</recordid><startdate>20060301</startdate><enddate>20060301</enddate><creator>Vercouillie, Johnny</creator><creator>Mavel, Sylvie</creator><creator>Galineau, Laurent</creator><creator>Ragusa, Tiziana</creator><creator>Innis, Robert</creator><creator>Kassiou, Michael</creator><creator>Chalon, Sylvie</creator><creator>Dollé, Frédéric</creator><creator>Besnard, Jean-Claude</creator><creator>Guilloteau, Denis</creator><creator>Emond, Patrick</creator><general>Elsevier Ltd</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>7QO</scope><scope>7TK</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20060301</creationdate><title>Synthesis and in vitro evaluation of novel derivatives of diphenylsulfide as serotonin transporter ligands</title><author>Vercouillie, Johnny ; Mavel, Sylvie ; Galineau, Laurent ; Ragusa, Tiziana ; Innis, Robert ; Kassiou, Michael ; Chalon, Sylvie ; Dollé, Frédéric ; Besnard, Jean-Claude ; Guilloteau, Denis ; Emond, Patrick</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-25d83247a7a7c933d43c9e09f9f018cfb8a57d01c0b09b08ad8d12a35f4dc96d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Biological and medical sciences</topic><topic>Diphenylsulfide derivatives</topic><topic>Inhibitory Concentration 50</topic><topic>Ligands</topic><topic>MADAM derivatives</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Monoamine transporters</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. 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As the serotonin transporter (SERT) is involved in several neurodegenerative and psychiatric disorders, radiopharmaceuticals to image the SERT by PET or SPECT would be very valuable in studying these diseases. For the development of imaging agents, we have synthesized novel derivatives of recently reported diphenylsulfide SERT ligands, in which the sulfur atom linking the two phenyl rings was replaced by an oxygen, sulfinyl, sulfonyl, amino or carbon group. Three of these exhibited good to high in vitro affinity (0.5
nM
<
K
i
<
11
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2006-03, Vol.16 (5), p.1297-1300 |
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| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Biological and medical sciences Diphenylsulfide derivatives Inhibitory Concentration 50 Ligands MADAM derivatives Medical sciences Molecular Structure Monoamine transporters Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pharmacology. Drug treatments Sensitivity and Specificity Serotonin Plasma Membrane Transport Proteins - metabolism Serotoninergic system SERT Structure-Activity Relationship Substrate Specificity Sulfides - chemical synthesis Sulfides - chemistry Sulfides - metabolism |
| title | Synthesis and in vitro evaluation of novel derivatives of diphenylsulfide as serotonin transporter ligands |
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