3,6-Dibromocarbazole Piperazine Derivatives of 2-Propanol as First Inhibitors of Cytochrome c Release via Bax Channel Modulation
There is compelling evidence that Bax channel activity stimulates cytochrome c release leading ultimately to cell death, which is a key event in ischemic injuries and neurodegenerative diseases. Here 3,6-dibromocarbazole piperazine derivatives of 2-propanol are described as the first small and poten...
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| Veröffentlicht in: | Journal of medicinal chemistry 2003-10, Vol.46 (21), p.4365-4368 |
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| container_end_page | 4368 |
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| container_issue | 21 |
| container_start_page | 4365 |
| container_title | Journal of medicinal chemistry |
| container_volume | 46 |
| creator | Bombrun, Agnes Gerber, Patrick Casi, Giulio Terradillos, Olivier Antonsson, Bruno Halazy, Serge |
| description | There is compelling evidence that Bax channel activity stimulates cytochrome c release leading ultimately to cell death, which is a key event in ischemic injuries and neurodegenerative diseases. Here 3,6-dibromocarbazole piperazine derivatives of 2-propanol are described as the first small and potent modulators of the cytochrome c release triggered by Bid-induced Bax activation in a mitochondrial assay. Furthermore, a mechanism of action is proposed, and fluorescent derivatives allowing the localization of such inhibitors are reported. |
| doi_str_mv | 10.1021/jm034107j |
| format | Article |
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Here 3,6-dibromocarbazole piperazine derivatives of 2-propanol are described as the first small and potent modulators of the cytochrome c release triggered by Bid-induced Bax activation in a mitochondrial assay. Furthermore, a mechanism of action is proposed, and fluorescent derivatives allowing the localization of such inhibitors are reported.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm034107j</identifier><identifier>PMID: 14521400</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Apoptosis - drug effects ; bcl-2-Associated X Protein ; Biological and medical sciences ; Carbazoles - chemical synthesis ; Carbazoles - pharmacology ; Cytochrome c Group - antagonists & inhibitors ; Cytochrome c Group - metabolism ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; Fluorescent Dyes ; HeLa Cells ; Humans ; Indicators and Reagents ; Liposomes ; Medical sciences ; Miscellaneous ; Mitochondria - drug effects ; Mitochondria - enzymology ; Pharmacology. Drug treatments ; Piperazines - chemical synthesis ; Piperazines - pharmacology ; Proto-Oncogene Proteins - antagonists & inhibitors ; Proto-Oncogene Proteins - metabolism ; Proto-Oncogene Proteins c-bcl-2 ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2003-10, Vol.46 (21), p.4365-4368</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-2e2a1974661b71c0e5984db8e9cba837a9afa353b8c46e765036326883eede3d3</citedby><cites>FETCH-LOGICAL-a379t-2e2a1974661b71c0e5984db8e9cba837a9afa353b8c46e765036326883eede3d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm034107j$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm034107j$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15202055$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14521400$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bombrun, Agnes</creatorcontrib><creatorcontrib>Gerber, Patrick</creatorcontrib><creatorcontrib>Casi, Giulio</creatorcontrib><creatorcontrib>Terradillos, Olivier</creatorcontrib><creatorcontrib>Antonsson, Bruno</creatorcontrib><creatorcontrib>Halazy, Serge</creatorcontrib><title>3,6-Dibromocarbazole Piperazine Derivatives of 2-Propanol as First Inhibitors of Cytochrome c Release via Bax Channel Modulation</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>There is compelling evidence that Bax channel activity stimulates cytochrome c release leading ultimately to cell death, which is a key event in ischemic injuries and neurodegenerative diseases. Here 3,6-dibromocarbazole piperazine derivatives of 2-propanol are described as the first small and potent modulators of the cytochrome c release triggered by Bid-induced Bax activation in a mitochondrial assay. Furthermore, a mechanism of action is proposed, and fluorescent derivatives allowing the localization of such inhibitors are reported.</description><subject>Apoptosis - drug effects</subject><subject>bcl-2-Associated X Protein</subject><subject>Biological and medical sciences</subject><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - pharmacology</subject><subject>Cytochrome c Group - antagonists & inhibitors</subject><subject>Cytochrome c Group - metabolism</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Fluorescent Dyes</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Liposomes</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Mitochondria - drug effects</subject><subject>Mitochondria - enzymology</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperazines - chemical synthesis</subject><subject>Piperazines - pharmacology</subject><subject>Proto-Oncogene Proteins - antagonists & inhibitors</subject><subject>Proto-Oncogene Proteins - metabolism</subject><subject>Proto-Oncogene Proteins c-bcl-2</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU2P0zAQQC0EYkvhwB9AvoCEtAF_xU6ObJf9kBZRoJytiTNRXZK42Em1u6f96QRabS-c5jBPT6M3hLzm7ANngn_cdEwqzszmCZnxXLBMFUw9JTPGhMiEFvKEvEhpwxiTXMjn5ISrXHDF2Iw8yFOdnfsqhi44iBXchxbp0m8xwr3vkZ5j9DsY_A4TDQ0V2TKGLfShpZDohY9poNf92ld-CPEfsbgbgltPPqSOfscWISHdeaBncEsXa-h7bOmXUI_tZA39S_KsgTbhq8Ock58Xn1eLq-zm6-X14tNNBtKUQyZQAC-N0ppXhjuGeVmouiqwdBUU0kAJDchcVoVTGo3OmdRS6KKQiDXKWs7Ju713G8PvEdNgO58cti30GMZkTW6kUFOeOXm_B10MKUVs7Db6DuKd5cz-zW0fc0_sm4N0rDqsj-Sh7wS8PQCQHLRNhN75dOSmZwmW5xOX7TmfBrx93EP8ZbWRJrer5Q_7TZwZtboq7eXRCy7ZTRhjP7X7z4F_AGhNonU</recordid><startdate>20031009</startdate><enddate>20031009</enddate><creator>Bombrun, Agnes</creator><creator>Gerber, Patrick</creator><creator>Casi, Giulio</creator><creator>Terradillos, Olivier</creator><creator>Antonsson, Bruno</creator><creator>Halazy, Serge</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20031009</creationdate><title>3,6-Dibromocarbazole Piperazine Derivatives of 2-Propanol as First Inhibitors of Cytochrome c Release via Bax Channel Modulation</title><author>Bombrun, Agnes ; Gerber, Patrick ; Casi, Giulio ; Terradillos, Olivier ; Antonsson, Bruno ; Halazy, Serge</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-2e2a1974661b71c0e5984db8e9cba837a9afa353b8c46e765036326883eede3d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Apoptosis - drug effects</topic><topic>bcl-2-Associated X Protein</topic><topic>Biological and medical sciences</topic><topic>Carbazoles - chemical synthesis</topic><topic>Carbazoles - pharmacology</topic><topic>Cytochrome c Group - antagonists & inhibitors</topic><topic>Cytochrome c Group - metabolism</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Fluorescent Dyes</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Liposomes</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Mitochondria - drug effects</topic><topic>Mitochondria - enzymology</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperazines - chemical synthesis</topic><topic>Piperazines - pharmacology</topic><topic>Proto-Oncogene Proteins - antagonists & inhibitors</topic><topic>Proto-Oncogene Proteins - metabolism</topic><topic>Proto-Oncogene Proteins c-bcl-2</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bombrun, Agnes</creatorcontrib><creatorcontrib>Gerber, Patrick</creatorcontrib><creatorcontrib>Casi, Giulio</creatorcontrib><creatorcontrib>Terradillos, Olivier</creatorcontrib><creatorcontrib>Antonsson, Bruno</creatorcontrib><creatorcontrib>Halazy, Serge</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>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bombrun, Agnes</au><au>Gerber, Patrick</au><au>Casi, Giulio</au><au>Terradillos, Olivier</au><au>Antonsson, Bruno</au><au>Halazy, Serge</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3,6-Dibromocarbazole Piperazine Derivatives of 2-Propanol as First Inhibitors of Cytochrome c Release via Bax Channel Modulation</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2003-10-09</date><risdate>2003</risdate><volume>46</volume><issue>21</issue><spage>4365</spage><epage>4368</epage><pages>4365-4368</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>There is compelling evidence that Bax channel activity stimulates cytochrome c release leading ultimately to cell death, which is a key event in ischemic injuries and neurodegenerative diseases. Here 3,6-dibromocarbazole piperazine derivatives of 2-propanol are described as the first small and potent modulators of the cytochrome c release triggered by Bid-induced Bax activation in a mitochondrial assay. Furthermore, a mechanism of action is proposed, and fluorescent derivatives allowing the localization of such inhibitors are reported.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14521400</pmid><doi>10.1021/jm034107j</doi><tpages>4</tpages></addata></record> |
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| subjects | Apoptosis - drug effects bcl-2-Associated X Protein Biological and medical sciences Carbazoles - chemical synthesis Carbazoles - pharmacology Cytochrome c Group - antagonists & inhibitors Cytochrome c Group - metabolism Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Fluorescent Dyes HeLa Cells Humans Indicators and Reagents Liposomes Medical sciences Miscellaneous Mitochondria - drug effects Mitochondria - enzymology Pharmacology. Drug treatments Piperazines - chemical synthesis Piperazines - pharmacology Proto-Oncogene Proteins - antagonists & inhibitors Proto-Oncogene Proteins - metabolism Proto-Oncogene Proteins c-bcl-2 Structure-Activity Relationship |
| title | 3,6-Dibromocarbazole Piperazine Derivatives of 2-Propanol as First Inhibitors of Cytochrome c Release via Bax Channel Modulation |
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