Synthesis and photoreactivity of caged blockers for glutamate transporters
l-TBOA ( l- threo-β-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized α-CMCM- l-TBOA ( 1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. α-CMCM- l-TBOA ( 1a) is biologically inactive until UV irradiation...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2003-03, Vol.13 (5), p.965-970 |
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| container_issue | 5 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 13 |
| creator | Takaoka, Kiyo Tatsu, Yoshiro Yumoto, Noboru Nakajima, Terumi Shimamoto, Keiko |
| description | l-TBOA (
l-
threo-β-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized α-CMCM-
l-TBOA (
1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. α-CMCM-
l-TBOA (
1a) is biologically inactive until UV irradiation and the photolysis of
1a immediately released
l-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the
o-nitrobenzyl-type caging group.
The photolysis of α-CMCM-
l-TBOA, a caged blocker for glutamate transporters, immediately released
l-TBOA to show glutamate uptake inhibition. |
| doi_str_mv | 10.1016/S0960-894X(02)01042-9 |
| format | Article |
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l-
threo-β-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized α-CMCM-
l-TBOA (
1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. α-CMCM-
l-TBOA (
1a) is biologically inactive until UV irradiation and the photolysis of
1a immediately released
l-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the
o-nitrobenzyl-type caging group.
The photolysis of α-CMCM-
l-TBOA, a caged blocker for glutamate transporters, immediately released
l-TBOA to show glutamate uptake inhibition.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(02)01042-9</identifier><identifier>PMID: 12617931</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amino Acid Transport System X-AG - antagonists & inhibitors ; Animals ; Aspartic Acid - chemistry ; Aspartic Acid - pharmacology ; Biological and medical sciences ; Biological Transport - drug effects ; Cell Line ; Coumarins - chemistry ; Coumarins - pharmacology ; Dogs ; Drug Stability ; Glutamic Acid - metabolism ; Medical sciences ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; Photolysis ; Spectrophotometry, Ultraviolet</subject><ispartof>Bioorganic & medicinal chemistry letters, 2003-03, Vol.13 (5), p.965-970</ispartof><rights>2003 Elsevier Science Ltd</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-4ee699242dee48fb50780abe64a2bc8dbed2fb1c656dd958e8f72a9ac1812bee3</citedby><cites>FETCH-LOGICAL-c457t-4ee699242dee48fb50780abe64a2bc8dbed2fb1c656dd958e8f72a9ac1812bee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0960-894X(02)01042-9$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14552996$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12617931$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Takaoka, Kiyo</creatorcontrib><creatorcontrib>Tatsu, Yoshiro</creatorcontrib><creatorcontrib>Yumoto, Noboru</creatorcontrib><creatorcontrib>Nakajima, Terumi</creatorcontrib><creatorcontrib>Shimamoto, Keiko</creatorcontrib><title>Synthesis and photoreactivity of caged blockers for glutamate transporters</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>l-TBOA (
l-
threo-β-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized α-CMCM-
l-TBOA (
1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. α-CMCM-
l-TBOA (
1a) is biologically inactive until UV irradiation and the photolysis of
1a immediately released
l-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the
o-nitrobenzyl-type caging group.
The photolysis of α-CMCM-
l-TBOA, a caged blocker for glutamate transporters, immediately released
l-TBOA to show glutamate uptake inhibition.</description><subject>Amino Acid Transport System X-AG - antagonists & inhibitors</subject><subject>Animals</subject><subject>Aspartic Acid - chemistry</subject><subject>Aspartic Acid - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Biological Transport - drug effects</subject><subject>Cell Line</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - pharmacology</subject><subject>Dogs</subject><subject>Drug Stability</subject><subject>Glutamic Acid - metabolism</subject><subject>Medical sciences</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Photolysis</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtOwzAQRS0EglL4BFA2IFgEbNdx4hVCFU9VYlGQ2FmOPWkNaVxsp1L_nvQhumQ1izn3zuggdEbwDcGE346x4DgtBPu8wvQaE8xoKvZQjzDO0gHD2T7q_SFH6DiEL4wJw4wdoiNCOcnFgPTQ63jZxCkEGxLVmGQ-ddF5UDrahY3LxFWJVhMwSVk7_Q0-JJXzyaRuo5qpCEn0qglz52O3OkEHlaoDnG5nH308PrwPn9PR29PL8H6UapblMWUAXAjKqAFgRVVmOC-wKoEzRUtdmBIMrUqiecaNEVkBRZVTJZQmBaElwKCPLje9c-9-WghRzmzQUNeqAdcGmQ-6RiFwB2YbUHsXgodKzr2dKb-UBMuVRLmWKFeGJKZyLVGKLne-PdCWMzC71NZaB1xsARW0qqtOgrZhx7Eso0LwjrvbcNDpWFjwMmgLjQZjPegojbP_vPILkwaQrA</recordid><startdate>20030310</startdate><enddate>20030310</enddate><creator>Takaoka, Kiyo</creator><creator>Tatsu, Yoshiro</creator><creator>Yumoto, Noboru</creator><creator>Nakajima, Terumi</creator><creator>Shimamoto, Keiko</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>7X8</scope></search><sort><creationdate>20030310</creationdate><title>Synthesis and photoreactivity of caged blockers for glutamate transporters</title><author>Takaoka, Kiyo ; Tatsu, Yoshiro ; Yumoto, Noboru ; Nakajima, Terumi ; Shimamoto, Keiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-4ee699242dee48fb50780abe64a2bc8dbed2fb1c656dd958e8f72a9ac1812bee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Amino Acid Transport System X-AG - antagonists & inhibitors</topic><topic>Animals</topic><topic>Aspartic Acid - chemistry</topic><topic>Aspartic Acid - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Biological Transport - drug effects</topic><topic>Cell Line</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - pharmacology</topic><topic>Dogs</topic><topic>Drug Stability</topic><topic>Glutamic Acid - metabolism</topic><topic>Medical sciences</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Photolysis</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Takaoka, Kiyo</creatorcontrib><creatorcontrib>Tatsu, Yoshiro</creatorcontrib><creatorcontrib>Yumoto, Noboru</creatorcontrib><creatorcontrib>Nakajima, Terumi</creatorcontrib><creatorcontrib>Shimamoto, Keiko</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Takaoka, Kiyo</au><au>Tatsu, Yoshiro</au><au>Yumoto, Noboru</au><au>Nakajima, Terumi</au><au>Shimamoto, Keiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and photoreactivity of caged blockers for glutamate transporters</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2003-03-10</date><risdate>2003</risdate><volume>13</volume><issue>5</issue><spage>965</spage><epage>970</epage><pages>965-970</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>l-TBOA (
l-
threo-β-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized α-CMCM-
l-TBOA (
1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. α-CMCM-
l-TBOA (
1a) is biologically inactive until UV irradiation and the photolysis of
1a immediately released
l-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the
o-nitrobenzyl-type caging group.
The photolysis of α-CMCM-
l-TBOA, a caged blocker for glutamate transporters, immediately released
l-TBOA to show glutamate uptake inhibition.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>12617931</pmid><doi>10.1016/S0960-894X(02)01042-9</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2003-03, Vol.13 (5), p.965-970 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73078990 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Amino Acid Transport System X-AG - antagonists & inhibitors Animals Aspartic Acid - chemistry Aspartic Acid - pharmacology Biological and medical sciences Biological Transport - drug effects Cell Line Coumarins - chemistry Coumarins - pharmacology Dogs Drug Stability Glutamic Acid - metabolism Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Photolysis Spectrophotometry, Ultraviolet |
| title | Synthesis and photoreactivity of caged blockers for glutamate transporters |
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