Affinity for Dopamine D2, D3, and D4 Receptors of 2-Aminotetralins. Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity
A series of 2-aminotetralins, substituted with a methoxy or a hydroxy group on the 5- or 7-position, and with varying N-alkyl or N-arylalkyl substituents, were prepared and evaluated in binding assays for human dopamine (DA) D2, D3, and D4 receptors. Some members of this series were prepared in form...
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| Veröffentlicht in: | Journal of medicinal chemistry 1996-10, Vol.39 (21), p.4233-4237 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 39 |
| creator | van Vliet, L. Alexander Tepper, Pieter G Dijkstra, Durk Damsma, Geert Wikström, Håkan Pugsley, Thomas A Akunne, Hyacinth C Heffner, Thomas G Glase, Shelly A Wise, Lawrence D |
| description | A series of 2-aminotetralins, substituted with a methoxy or a hydroxy group on the 5- or 7-position, and with varying N-alkyl or N-arylalkyl substituents, were prepared and evaluated in binding assays for human dopamine (DA) D2, D3, and D4 receptors. Some members of this series were prepared in former studies, but were never tested in vitro with single receptor subtypes, and these were examined again. None of the tested 2-aminotetralins showed high affinity for the dopamine D4 receptor. However, a number of the 2-aminotetralins showed high affinity for both the D2 and the D3 DA receptors, as exemplified by compounds 11−15 and 21−26, while some had a reasonable selectivity for the DA D3 receptors. The affinities of the 2-aminotetralins for the D2L receptor depended on the type of radioligand (agonist or antagonist) used. The agonist affinity data, obtained by using the agonist ligand [3H]N-0437, are thought to be more relevant for calculating DA receptor subtype selectivity. |
| doi_str_mv | 10.1021/jm960345l |
| format | Article |
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Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity</title><source>American Chemical Society</source><source>MEDLINE</source><creator>van Vliet, L. Alexander ; Tepper, Pieter G ; Dijkstra, Durk ; Damsma, Geert ; Wikström, Håkan ; Pugsley, Thomas A ; Akunne, Hyacinth C ; Heffner, Thomas G ; Glase, Shelly A ; Wise, Lawrence D</creator><creatorcontrib>van Vliet, L. Alexander ; Tepper, Pieter G ; Dijkstra, Durk ; Damsma, Geert ; Wikström, Håkan ; Pugsley, Thomas A ; Akunne, Hyacinth C ; Heffner, Thomas G ; Glase, Shelly A ; Wise, Lawrence D</creatorcontrib><description>A series of 2-aminotetralins, substituted with a methoxy or a hydroxy group on the 5- or 7-position, and with varying N-alkyl or N-arylalkyl substituents, were prepared and evaluated in binding assays for human dopamine (DA) D2, D3, and D4 receptors. Some members of this series were prepared in former studies, but were never tested in vitro with single receptor subtypes, and these were examined again. None of the tested 2-aminotetralins showed high affinity for the dopamine D4 receptor. However, a number of the 2-aminotetralins showed high affinity for both the D2 and the D3 DA receptors, as exemplified by compounds 11−15 and 21−26, while some had a reasonable selectivity for the DA D3 receptors. The affinities of the 2-aminotetralins for the D2L receptor depended on the type of radioligand (agonist or antagonist) used. The agonist affinity data, obtained by using the agonist ligand [3H]N-0437, are thought to be more relevant for calculating DA receptor subtype selectivity.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm960345l</identifier><identifier>PMID: 8863800</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Biological and medical sciences ; Catecholaminergic system ; Cell Line ; Cricetinae ; Cricetulus ; Female ; Humans ; Kinetics ; Medical sciences ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Ovary - metabolism ; Pharmacology. Drug treatments ; Receptors, Dopamine D2 - agonists ; Receptors, Dopamine D2 - metabolism ; Receptors, Dopamine D3 ; Receptors, Dopamine D4 ; Substrate Specificity ; Tetrahydronaphthalenes - chemistry ; Tetrahydronaphthalenes - metabolism</subject><ispartof>Journal of medicinal chemistry, 1996-10, Vol.39 (21), p.4233-4237</ispartof><rights>Copyright © 1996 American Chemical Society</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm960345l$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm960345l$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3248541$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8863800$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>van Vliet, L. Alexander</creatorcontrib><creatorcontrib>Tepper, Pieter G</creatorcontrib><creatorcontrib>Dijkstra, Durk</creatorcontrib><creatorcontrib>Damsma, Geert</creatorcontrib><creatorcontrib>Wikström, Håkan</creatorcontrib><creatorcontrib>Pugsley, Thomas A</creatorcontrib><creatorcontrib>Akunne, Hyacinth C</creatorcontrib><creatorcontrib>Heffner, Thomas G</creatorcontrib><creatorcontrib>Glase, Shelly A</creatorcontrib><creatorcontrib>Wise, Lawrence D</creatorcontrib><title>Affinity for Dopamine D2, D3, and D4 Receptors of 2-Aminotetralins. Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of 2-aminotetralins, substituted with a methoxy or a hydroxy group on the 5- or 7-position, and with varying N-alkyl or N-arylalkyl substituents, were prepared and evaluated in binding assays for human dopamine (DA) D2, D3, and D4 receptors. Some members of this series were prepared in former studies, but were never tested in vitro with single receptor subtypes, and these were examined again. None of the tested 2-aminotetralins showed high affinity for the dopamine D4 receptor. However, a number of the 2-aminotetralins showed high affinity for both the D2 and the D3 DA receptors, as exemplified by compounds 11−15 and 21−26, while some had a reasonable selectivity for the DA D3 receptors. The affinities of the 2-aminotetralins for the D2L receptor depended on the type of radioligand (agonist or antagonist) used. The agonist affinity data, obtained by using the agonist ligand [3H]N-0437, are thought to be more relevant for calculating DA receptor subtype selectivity.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Catecholaminergic system</subject><subject>Cell Line</subject><subject>Cricetinae</subject><subject>Cricetulus</subject><subject>Female</subject><subject>Humans</subject><subject>Kinetics</subject><subject>Medical sciences</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Ovary - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Receptors, Dopamine D2 - agonists</subject><subject>Receptors, Dopamine D2 - metabolism</subject><subject>Receptors, Dopamine D3</subject><subject>Receptors, Dopamine D4</subject><subject>Substrate Specificity</subject><subject>Tetrahydronaphthalenes - chemistry</subject><subject>Tetrahydronaphthalenes - metabolism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kc1uEzEURi0EKqGw4AGQvABWneK_GU-WSaZQRCQqUtaW7bErh4k9tT0VeRDet44SsrqLc-6nq-8C8B6ja4wI_rLdzRtEWT28ADNcE1SxFrGXYIYQIRVpCH0N3qS0RQhRTOgFuGjbhrYIzcC_hbXOu7yHNkTYhVHunDewI1ewo1dQ-h52DP4y2ow5xASDhaRaFCdkk6McnE_XBQ_mSXptDrgjcPEQvEsZLp3vnX84RptsYtmT2QV_8P5nws2k8n40cFNSdHZP5Zi34JWVQzLvTvMS_P56c7-6rdY_v31fLdaVJLjNFddWW8L4HPWtoraplTJacSIVNpajeUM0Z6TuTc-VrImSvFENV7huteylQvQSfD7mjjE8TiZlsXNJm2GQ3oQpCd4yhjBnRfxwEie1M70Yo9vJuBenHgv_eOIyaTnYWNpw6axRwtqa4aJVR620Y_6esYx_RMMpr8X93UYs79ZotVzdih_F_3T0pU5iG6boSxsCI3H4ujh_nT4DaMicaA</recordid><startdate>19961011</startdate><enddate>19961011</enddate><creator>van Vliet, L. Alexander</creator><creator>Tepper, Pieter G</creator><creator>Dijkstra, Durk</creator><creator>Damsma, Geert</creator><creator>Wikström, Håkan</creator><creator>Pugsley, Thomas A</creator><creator>Akunne, Hyacinth C</creator><creator>Heffner, Thomas G</creator><creator>Glase, Shelly A</creator><creator>Wise, Lawrence D</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>7X8</scope></search><sort><creationdate>19961011</creationdate><title>Affinity for Dopamine D2, D3, and D4 Receptors of 2-Aminotetralins. Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity</title><author>van Vliet, L. Alexander ; Tepper, Pieter G ; Dijkstra, Durk ; Damsma, Geert ; Wikström, Håkan ; Pugsley, Thomas A ; Akunne, Hyacinth C ; Heffner, Thomas G ; Glase, Shelly A ; Wise, Lawrence D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a218t-7cfcf24790d8b3f65bbecb72ab1ef70962c7425ded7ba52ba76b67b158cadab03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Catecholaminergic system</topic><topic>Cell Line</topic><topic>Cricetinae</topic><topic>Cricetulus</topic><topic>Female</topic><topic>Humans</topic><topic>Kinetics</topic><topic>Medical sciences</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Ovary - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>Receptors, Dopamine D2 - agonists</topic><topic>Receptors, Dopamine D2 - metabolism</topic><topic>Receptors, Dopamine D3</topic><topic>Receptors, Dopamine D4</topic><topic>Substrate Specificity</topic><topic>Tetrahydronaphthalenes - chemistry</topic><topic>Tetrahydronaphthalenes - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>van Vliet, L. Alexander</creatorcontrib><creatorcontrib>Tepper, Pieter G</creatorcontrib><creatorcontrib>Dijkstra, Durk</creatorcontrib><creatorcontrib>Damsma, Geert</creatorcontrib><creatorcontrib>Wikström, Håkan</creatorcontrib><creatorcontrib>Pugsley, Thomas A</creatorcontrib><creatorcontrib>Akunne, Hyacinth C</creatorcontrib><creatorcontrib>Heffner, Thomas G</creatorcontrib><creatorcontrib>Glase, Shelly A</creatorcontrib><creatorcontrib>Wise, Lawrence D</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>van Vliet, L. Alexander</au><au>Tepper, Pieter G</au><au>Dijkstra, Durk</au><au>Damsma, Geert</au><au>Wikström, Håkan</au><au>Pugsley, Thomas A</au><au>Akunne, Hyacinth C</au><au>Heffner, Thomas G</au><au>Glase, Shelly A</au><au>Wise, Lawrence D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Affinity for Dopamine D2, D3, and D4 Receptors of 2-Aminotetralins. Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1996-10-11</date><risdate>1996</risdate><volume>39</volume><issue>21</issue><spage>4233</spage><epage>4237</epage><pages>4233-4237</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of 2-aminotetralins, substituted with a methoxy or a hydroxy group on the 5- or 7-position, and with varying N-alkyl or N-arylalkyl substituents, were prepared and evaluated in binding assays for human dopamine (DA) D2, D3, and D4 receptors. Some members of this series were prepared in former studies, but were never tested in vitro with single receptor subtypes, and these were examined again. None of the tested 2-aminotetralins showed high affinity for the dopamine D4 receptor. However, a number of the 2-aminotetralins showed high affinity for both the D2 and the D3 DA receptors, as exemplified by compounds 11−15 and 21−26, while some had a reasonable selectivity for the DA D3 receptors. The affinities of the 2-aminotetralins for the D2L receptor depended on the type of radioligand (agonist or antagonist) used. The agonist affinity data, obtained by using the agonist ligand [3H]N-0437, are thought to be more relevant for calculating DA receptor subtype selectivity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>8863800</pmid><doi>10.1021/jm960345l</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1996-10, Vol.39 (21), p.4233-4237 |
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| source | American Chemical Society; MEDLINE |
| subjects | Animals Biological and medical sciences Catecholaminergic system Cell Line Cricetinae Cricetulus Female Humans Kinetics Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Ovary - metabolism Pharmacology. Drug treatments Receptors, Dopamine D2 - agonists Receptors, Dopamine D2 - metabolism Receptors, Dopamine D3 Receptors, Dopamine D4 Substrate Specificity Tetrahydronaphthalenes - chemistry Tetrahydronaphthalenes - metabolism |
| title | Affinity for Dopamine D2, D3, and D4 Receptors of 2-Aminotetralins. Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity |
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