Inhibition of γ-aminobutyric acid uptake by bicuculline analogues
Enantiomers of norbicuculline, (+)[1 S,9 R] and (−)[1 R,9 S] erythro-1-[1′-(4′,5′-methylenedioxyphthalidyl)]-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and of the N-methyl derivatives {(+)[1 S,9 R] and (−)[1 R,9 S]bicuculline} were found to inhibit the progress of the γ-aminobutyric acid tran...
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| Veröffentlicht in: | European journal of pharmacology 1997-10, Vol.337 (1), p.83-86 |
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| creator | Kardos, Julianna Kovács, Ilona Blandl, Tamás Cash, Derek J Simon-Trompler, Edit Luyen, Nguyen D Dörnyei, Gábor Simonyi, Miklós Blaskó, Gábor Szántay, Csaba |
| description | Enantiomers of
norbicuculline, (+)[1
S,9
R] and (−)[1
R,9
S]
erythro-1-[1′-(4′,5′-methylenedioxyphthalidyl)]-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and of the
N-methyl derivatives {(+)[1
S,9
R] and (−)[1
R,9
S]bicuculline} were found to inhibit the progress of the
γ-aminobutyric acid transporter-mediated uptake of 40 μM [
14
C
]
γ-aminobutyric acid into native plasma membrane vesicles from the rat cerebral cortex at 30°C. The values for the dissociation constants of the reversible inhibition, relative to (+)[1
S,9
R]bicuculline, in order of increasing inhibition, were: (−)[1
R,9
S]bicuculline, 3.3; (+)[1
S,9
R]-bicuculline, 1.0; (−)[1
R,9
S]
norbicuculline, 0.4≈(+)[1
S,9
R]
norbicuculline; guvacine, 0.02. The
norbicucullines have higher potencies than (+)[1
S,9
R]bicuculline for the
γ-aminobutyric acid transporter, in contrast to the relative potencies of these inhibitors for the inhibition of function and
γ-aminobutyric acid binding of the
γ-aminobutyric acid type A receptor. |
| doi_str_mv | 10.1016/S0014-2999(97)01267-3 |
| format | Article |
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norbicuculline, (+)[1
S,9
R] and (−)[1
R,9
S]
erythro-1-[1′-(4′,5′-methylenedioxyphthalidyl)]-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and of the
N-methyl derivatives {(+)[1
S,9
R] and (−)[1
R,9
S]bicuculline} were found to inhibit the progress of the
γ-aminobutyric acid transporter-mediated uptake of 40 μM [
14
C
]
γ-aminobutyric acid into native plasma membrane vesicles from the rat cerebral cortex at 30°C. The values for the dissociation constants of the reversible inhibition, relative to (+)[1
S,9
R]bicuculline, in order of increasing inhibition, were: (−)[1
R,9
S]bicuculline, 3.3; (+)[1
S,9
R]-bicuculline, 1.0; (−)[1
R,9
S]
norbicuculline, 0.4≈(+)[1
S,9
R]
norbicuculline; guvacine, 0.02. The
norbicucullines have higher potencies than (+)[1
S,9
R]bicuculline for the
γ-aminobutyric acid transporter, in contrast to the relative potencies of these inhibitors for the inhibition of function and
γ-aminobutyric acid binding of the
γ-aminobutyric acid type A receptor.</description><identifier>ISSN: 0014-2999</identifier><identifier>EISSN: 1879-0712</identifier><identifier>DOI: 10.1016/S0014-2999(97)01267-3</identifier><identifier>PMID: 9389384</identifier><identifier>CODEN: EJPHAZ</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>[ [formula omitted]]GABA ([ [formula omitted]] γ-aminobutyric acid) ; Animals ; Bicuculline - analogs & derivatives ; Bicuculline - pharmacology ; Bicuculline analogue, enantiomer ; Biochemistry and metabolism ; Biological and medical sciences ; Cell Membrane - drug effects ; Cell Membrane - metabolism ; Central nervous system ; Cerebral Cortex - drug effects ; Cerebral Cortex - metabolism ; Cortex, rat ; Fundamental and applied biological sciences. Psychology ; GABA Antagonists - pharmacology ; gamma-Aminobutyric Acid - metabolism ; In Vitro Techniques ; Rats ; Stereoisomerism ; Uptake, quench flow ; Vertebrates: nervous system and sense organs</subject><ispartof>European journal of pharmacology, 1997-10, Vol.337 (1), p.83-86</ispartof><rights>1997 Elsevier Science B.V.</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-85f5f5afeced5b674f79486479a152561470397bd221780a5b2b43648b9482e3</citedby><cites>FETCH-LOGICAL-c389t-85f5f5afeced5b674f79486479a152561470397bd221780a5b2b43648b9482e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0014299997012673$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2046498$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9389384$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kardos, Julianna</creatorcontrib><creatorcontrib>Kovács, Ilona</creatorcontrib><creatorcontrib>Blandl, Tamás</creatorcontrib><creatorcontrib>Cash, Derek J</creatorcontrib><creatorcontrib>Simon-Trompler, Edit</creatorcontrib><creatorcontrib>Luyen, Nguyen D</creatorcontrib><creatorcontrib>Dörnyei, Gábor</creatorcontrib><creatorcontrib>Simonyi, Miklós</creatorcontrib><creatorcontrib>Blaskó, Gábor</creatorcontrib><creatorcontrib>Szántay, Csaba</creatorcontrib><title>Inhibition of γ-aminobutyric acid uptake by bicuculline analogues</title><title>European journal of pharmacology</title><addtitle>Eur J Pharmacol</addtitle><description>Enantiomers of
norbicuculline, (+)[1
S,9
R] and (−)[1
R,9
S]
erythro-1-[1′-(4′,5′-methylenedioxyphthalidyl)]-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and of the
N-methyl derivatives {(+)[1
S,9
R] and (−)[1
R,9
S]bicuculline} were found to inhibit the progress of the
γ-aminobutyric acid transporter-mediated uptake of 40 μM [
14
C
]
γ-aminobutyric acid into native plasma membrane vesicles from the rat cerebral cortex at 30°C. The values for the dissociation constants of the reversible inhibition, relative to (+)[1
S,9
R]bicuculline, in order of increasing inhibition, were: (−)[1
R,9
S]bicuculline, 3.3; (+)[1
S,9
R]-bicuculline, 1.0; (−)[1
R,9
S]
norbicuculline, 0.4≈(+)[1
S,9
R]
norbicuculline; guvacine, 0.02. The
norbicucullines have higher potencies than (+)[1
S,9
R]bicuculline for the
γ-aminobutyric acid transporter, in contrast to the relative potencies of these inhibitors for the inhibition of function and
γ-aminobutyric acid binding of the
γ-aminobutyric acid type A receptor.</description><subject>[ [formula omitted]]GABA ([ [formula omitted]] γ-aminobutyric acid)</subject><subject>Animals</subject><subject>Bicuculline - analogs & derivatives</subject><subject>Bicuculline - pharmacology</subject><subject>Bicuculline analogue, enantiomer</subject><subject>Biochemistry and metabolism</subject><subject>Biological and medical sciences</subject><subject>Cell Membrane - drug effects</subject><subject>Cell Membrane - metabolism</subject><subject>Central nervous system</subject><subject>Cerebral Cortex - drug effects</subject><subject>Cerebral Cortex - metabolism</subject><subject>Cortex, rat</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>GABA Antagonists - pharmacology</subject><subject>gamma-Aminobutyric Acid - metabolism</subject><subject>In Vitro Techniques</subject><subject>Rats</subject><subject>Stereoisomerism</subject><subject>Uptake, quench flow</subject><subject>Vertebrates: nervous system and sense organs</subject><issn>0014-2999</issn><issn>1879-0712</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkN9OwyAUh4nRzDl9hCW9MEYvqkBpKVdGF_8sWeKFuydAqaItTGhN9ly-h88k25rdGki4ON85v8MHwBTBawRRcfMKISIpZoxdMnoFES5omh2AMSopSyFF-BCM98gxOAnhA0KYM5yPwIhlZbxkDO7n9t1I0xlnE1cnvz-paI11su_W3qhEKFMl_aoTnzqR60Qa1au-aYzVibCicW-9DqfgqBZN0GfDOwHLx4fl7DldvDzNZ3eLVMWwLi3zOh5Ra6WrXBaU1JSRsiCUCZTjvECEwoxRWWGMaAlFLrEkWUFKGTGsswm42I1defcVYzvemqB00wirXR94nBbbsyyC-Q5U3oXgdc1X3rTCrzmCfKOOb9XxjRfOKN-q45u-6RDQy1ZX-67BVayfD3URlGhqL6wyYY9hSArCyojd7jAdXXwb7XlQRtv4a-O16njlzD-L_AH8FIpf</recordid><startdate>19971015</startdate><enddate>19971015</enddate><creator>Kardos, Julianna</creator><creator>Kovács, Ilona</creator><creator>Blandl, Tamás</creator><creator>Cash, Derek J</creator><creator>Simon-Trompler, Edit</creator><creator>Luyen, Nguyen D</creator><creator>Dörnyei, Gábor</creator><creator>Simonyi, Miklós</creator><creator>Blaskó, Gábor</creator><creator>Szántay, Csaba</creator><general>Elsevier B.V</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>7X8</scope></search><sort><creationdate>19971015</creationdate><title>Inhibition of γ-aminobutyric acid uptake by bicuculline analogues</title><author>Kardos, Julianna ; Kovács, Ilona ; Blandl, Tamás ; Cash, Derek J ; Simon-Trompler, Edit ; Luyen, Nguyen D ; Dörnyei, Gábor ; Simonyi, Miklós ; Blaskó, Gábor ; Szántay, Csaba</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-85f5f5afeced5b674f79486479a152561470397bd221780a5b2b43648b9482e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>[ [formula omitted]]GABA ([ [formula omitted]] γ-aminobutyric acid)</topic><topic>Animals</topic><topic>Bicuculline - analogs & derivatives</topic><topic>Bicuculline - pharmacology</topic><topic>Bicuculline analogue, enantiomer</topic><topic>Biochemistry and metabolism</topic><topic>Biological and medical sciences</topic><topic>Cell Membrane - drug effects</topic><topic>Cell Membrane - metabolism</topic><topic>Central nervous system</topic><topic>Cerebral Cortex - drug effects</topic><topic>Cerebral Cortex - metabolism</topic><topic>Cortex, rat</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>GABA Antagonists - pharmacology</topic><topic>gamma-Aminobutyric Acid - metabolism</topic><topic>In Vitro Techniques</topic><topic>Rats</topic><topic>Stereoisomerism</topic><topic>Uptake, quench flow</topic><topic>Vertebrates: nervous system and sense organs</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kardos, Julianna</creatorcontrib><creatorcontrib>Kovács, Ilona</creatorcontrib><creatorcontrib>Blandl, Tamás</creatorcontrib><creatorcontrib>Cash, Derek J</creatorcontrib><creatorcontrib>Simon-Trompler, Edit</creatorcontrib><creatorcontrib>Luyen, Nguyen D</creatorcontrib><creatorcontrib>Dörnyei, Gábor</creatorcontrib><creatorcontrib>Simonyi, Miklós</creatorcontrib><creatorcontrib>Blaskó, Gábor</creatorcontrib><creatorcontrib>Szántay, Csaba</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>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of pharmacology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kardos, Julianna</au><au>Kovács, Ilona</au><au>Blandl, Tamás</au><au>Cash, Derek J</au><au>Simon-Trompler, Edit</au><au>Luyen, Nguyen D</au><au>Dörnyei, Gábor</au><au>Simonyi, Miklós</au><au>Blaskó, Gábor</au><au>Szántay, Csaba</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of γ-aminobutyric acid uptake by bicuculline analogues</atitle><jtitle>European journal of pharmacology</jtitle><addtitle>Eur J Pharmacol</addtitle><date>1997-10-15</date><risdate>1997</risdate><volume>337</volume><issue>1</issue><spage>83</spage><epage>86</epage><pages>83-86</pages><issn>0014-2999</issn><eissn>1879-0712</eissn><coden>EJPHAZ</coden><abstract>Enantiomers of
norbicuculline, (+)[1
S,9
R] and (−)[1
R,9
S]
erythro-1-[1′-(4′,5′-methylenedioxyphthalidyl)]-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline and of the
N-methyl derivatives {(+)[1
S,9
R] and (−)[1
R,9
S]bicuculline} were found to inhibit the progress of the
γ-aminobutyric acid transporter-mediated uptake of 40 μM [
14
C
]
γ-aminobutyric acid into native plasma membrane vesicles from the rat cerebral cortex at 30°C. The values for the dissociation constants of the reversible inhibition, relative to (+)[1
S,9
R]bicuculline, in order of increasing inhibition, were: (−)[1
R,9
S]bicuculline, 3.3; (+)[1
S,9
R]-bicuculline, 1.0; (−)[1
R,9
S]
norbicuculline, 0.4≈(+)[1
S,9
R]
norbicuculline; guvacine, 0.02. The
norbicucullines have higher potencies than (+)[1
S,9
R]bicuculline for the
γ-aminobutyric acid transporter, in contrast to the relative potencies of these inhibitors for the inhibition of function and
γ-aminobutyric acid binding of the
γ-aminobutyric acid type A receptor.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>9389384</pmid><doi>10.1016/S0014-2999(97)01267-3</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0014-2999 |
| ispartof | European journal of pharmacology, 1997-10, Vol.337 (1), p.83-86 |
| issn | 0014-2999 1879-0712 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79439733 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | [ [formula omitted]]GABA ([ [formula omitted]] γ-aminobutyric acid) Animals Bicuculline - analogs & derivatives Bicuculline - pharmacology Bicuculline analogue, enantiomer Biochemistry and metabolism Biological and medical sciences Cell Membrane - drug effects Cell Membrane - metabolism Central nervous system Cerebral Cortex - drug effects Cerebral Cortex - metabolism Cortex, rat Fundamental and applied biological sciences. Psychology GABA Antagonists - pharmacology gamma-Aminobutyric Acid - metabolism In Vitro Techniques Rats Stereoisomerism Uptake, quench flow Vertebrates: nervous system and sense organs |
| title | Inhibition of γ-aminobutyric acid uptake by bicuculline analogues |
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