Inhibitors of Human Histone Deacetylase: Synthesis and Enzyme and Cellular Activity of Straight Chain Hydroxamates
Inhibitors of histone deacetylase (HDAC) have been shown to induce terminal differentiation of human tumor cell lines and to have antitumor effects in vivo. We have prepared analogues of suberoylanilide hydroxamic acid (SAHA) and trichostatin A and have evaluated them in a human HDAC enzyme inhibiti...
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| Veröffentlicht in: | Journal of medicinal chemistry 2002-02, Vol.45 (4), p.753-757 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 45 |
| creator | Remiszewski, Stacy W Sambucetti, Lidia C Atadja, Peter Bair, Kenneth W Cornell, Wendy D Green, Michael A Howell, Kobporn Lulu Jung, Manfred Kwon, Paul Trogani, Nancy Walker, Heather |
| description | Inhibitors of histone deacetylase (HDAC) have been shown to induce terminal differentiation of human tumor cell lines and to have antitumor effects in vivo. We have prepared analogues of suberoylanilide hydroxamic acid (SAHA) and trichostatin A and have evaluated them in a human HDAC enzyme inhibition assay, a p21waf1 (p21) promoter assay, and in monolayer growth inhibition assays. One compound, 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-benzamide, was found to affect the growth of a panel of eight human tumor cell lines differentially. |
| doi_str_mv | 10.1021/jm015568c |
| format | Article |
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We have prepared analogues of suberoylanilide hydroxamic acid (SAHA) and trichostatin A and have evaluated them in a human HDAC enzyme inhibition assay, a p21waf1 (p21) promoter assay, and in monolayer growth inhibition assays. One compound, 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-benzamide, was found to affect the growth of a panel of eight human tumor cell lines differentially.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm015568c</identifier><identifier>PMID: 11831887</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Benzamides - chemical synthesis ; Benzamides - chemistry ; Benzamides - pharmacology ; Biological and medical sciences ; Cyclin-Dependent Kinase Inhibitor p21 ; Cyclins - metabolism ; Drug Screening Assays, Antitumor ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; General aspects ; Histone Deacetylase Inhibitors ; Humans ; Hydroxamic Acids - chemical synthesis ; Hydroxamic Acids - chemistry ; Hydroxamic Acids - pharmacology ; Hydroxylamines - chemical synthesis ; Hydroxylamines - chemistry ; Hydroxylamines - pharmacology ; Medical sciences ; Models, Molecular ; Pharmacology. Drug treatments ; Promoter Regions, Genetic ; Structure-Activity Relationship ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 2002-02, Vol.45 (4), p.753-757</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-e87532126829f1a22f0b8fd75e9de5f43fe9286e34565d3a174c8ad2511ba21e3</citedby><cites>FETCH-LOGICAL-a445t-e87532126829f1a22f0b8fd75e9de5f43fe9286e34565d3a174c8ad2511ba21e3</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/jm015568c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm015568c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13481138$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11831887$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Remiszewski, Stacy W</creatorcontrib><creatorcontrib>Sambucetti, Lidia C</creatorcontrib><creatorcontrib>Atadja, Peter</creatorcontrib><creatorcontrib>Bair, Kenneth W</creatorcontrib><creatorcontrib>Cornell, Wendy D</creatorcontrib><creatorcontrib>Green, Michael A</creatorcontrib><creatorcontrib>Howell, Kobporn Lulu</creatorcontrib><creatorcontrib>Jung, Manfred</creatorcontrib><creatorcontrib>Kwon, Paul</creatorcontrib><creatorcontrib>Trogani, Nancy</creatorcontrib><creatorcontrib>Walker, Heather</creatorcontrib><title>Inhibitors of Human Histone Deacetylase: Synthesis and Enzyme and Cellular Activity of Straight Chain Hydroxamates</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Inhibitors of histone deacetylase (HDAC) have been shown to induce terminal differentiation of human tumor cell lines and to have antitumor effects in vivo. We have prepared analogues of suberoylanilide hydroxamic acid (SAHA) and trichostatin A and have evaluated them in a human HDAC enzyme inhibition assay, a p21waf1 (p21) promoter assay, and in monolayer growth inhibition assays. One compound, 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-benzamide, was found to affect the growth of a panel of eight human tumor cell lines differentially.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Benzamides - chemical synthesis</subject><subject>Benzamides - chemistry</subject><subject>Benzamides - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cyclin-Dependent Kinase Inhibitor p21</subject><subject>Cyclins - metabolism</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>General aspects</subject><subject>Histone Deacetylase Inhibitors</subject><subject>Humans</subject><subject>Hydroxamic Acids - chemical synthesis</subject><subject>Hydroxamic Acids - chemistry</subject><subject>Hydroxamic Acids - pharmacology</subject><subject>Hydroxylamines - chemical synthesis</subject><subject>Hydroxylamines - chemistry</subject><subject>Hydroxylamines - pharmacology</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Promoter Regions, Genetic</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1v00AQQFcIRNPCgT-AfAGpB5ed_bDX3KpQSFFVkFIkbquJPSYb_FF216jmxLV_s7-kLomaC6cZaZ6eRo-xV8BPgAt4t2k5aJ2Z8gmbgRY8VYarp2zGuRCpyIQ8YIchbDjnEoR8zg4AjARj8hkbzru1W7nY-5D0dbIYWuyShQux7yj5QFhSHBsM9P7u722yHLu4puBCgl2VnHV_xpb-rXNqmqFBn5yW0f12cXxwLaNH92Mdk_ka3SQdK9_fYIuRwgv2rMYm0MvdPGLfPp5dzRfpxZdP5_PTixSV0jElk2spQGRGFDWgEDVfmbrKNRUV6VrJmgphMpJKZ7qSCLkqDVZCA6xQAMkj9nbrvfb9r4FCtK0L5fQsdtQPweagFC9ATeDxFix9H4Kn2l5716IfLXD70Ng-Np7Y1zvpsGqp2pO7qBPwZgdgKLGpPXalC3tOKgMgzcSlW27KTTePd_Q_bZbLXNurr0urPl8qKC6_W7H3Yhnsph98N7X7z4P3GqCgCg</recordid><startdate>20020214</startdate><enddate>20020214</enddate><creator>Remiszewski, Stacy W</creator><creator>Sambucetti, Lidia C</creator><creator>Atadja, Peter</creator><creator>Bair, Kenneth W</creator><creator>Cornell, Wendy D</creator><creator>Green, Michael A</creator><creator>Howell, Kobporn Lulu</creator><creator>Jung, Manfred</creator><creator>Kwon, Paul</creator><creator>Trogani, Nancy</creator><creator>Walker, Heather</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>20020214</creationdate><title>Inhibitors of Human Histone Deacetylase: Synthesis and Enzyme and Cellular Activity of Straight Chain Hydroxamates</title><author>Remiszewski, Stacy W ; Sambucetti, Lidia C ; Atadja, Peter ; Bair, Kenneth W ; Cornell, Wendy D ; Green, Michael A ; Howell, Kobporn Lulu ; Jung, Manfred ; Kwon, Paul ; Trogani, Nancy ; Walker, Heather</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-e87532126829f1a22f0b8fd75e9de5f43fe9286e34565d3a174c8ad2511ba21e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Benzamides - chemical synthesis</topic><topic>Benzamides - chemistry</topic><topic>Benzamides - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cyclin-Dependent Kinase Inhibitor p21</topic><topic>Cyclins - metabolism</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>General aspects</topic><topic>Histone Deacetylase Inhibitors</topic><topic>Humans</topic><topic>Hydroxamic Acids - chemical synthesis</topic><topic>Hydroxamic Acids - chemistry</topic><topic>Hydroxamic Acids - pharmacology</topic><topic>Hydroxylamines - chemical synthesis</topic><topic>Hydroxylamines - chemistry</topic><topic>Hydroxylamines - pharmacology</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Promoter Regions, Genetic</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Remiszewski, Stacy W</creatorcontrib><creatorcontrib>Sambucetti, Lidia C</creatorcontrib><creatorcontrib>Atadja, Peter</creatorcontrib><creatorcontrib>Bair, Kenneth W</creatorcontrib><creatorcontrib>Cornell, Wendy D</creatorcontrib><creatorcontrib>Green, Michael A</creatorcontrib><creatorcontrib>Howell, Kobporn Lulu</creatorcontrib><creatorcontrib>Jung, Manfred</creatorcontrib><creatorcontrib>Kwon, Paul</creatorcontrib><creatorcontrib>Trogani, Nancy</creatorcontrib><creatorcontrib>Walker, Heather</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>Remiszewski, Stacy W</au><au>Sambucetti, Lidia C</au><au>Atadja, Peter</au><au>Bair, Kenneth W</au><au>Cornell, Wendy D</au><au>Green, Michael A</au><au>Howell, Kobporn Lulu</au><au>Jung, Manfred</au><au>Kwon, Paul</au><au>Trogani, Nancy</au><au>Walker, Heather</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibitors of Human Histone Deacetylase: Synthesis and Enzyme and Cellular Activity of Straight Chain Hydroxamates</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2002-02-14</date><risdate>2002</risdate><volume>45</volume><issue>4</issue><spage>753</spage><epage>757</epage><pages>753-757</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Inhibitors of histone deacetylase (HDAC) have been shown to induce terminal differentiation of human tumor cell lines and to have antitumor effects in vivo. We have prepared analogues of suberoylanilide hydroxamic acid (SAHA) and trichostatin A and have evaluated them in a human HDAC enzyme inhibition assay, a p21waf1 (p21) promoter assay, and in monolayer growth inhibition assays. One compound, 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-benzamide, was found to affect the growth of a panel of eight human tumor cell lines differentially.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11831887</pmid><doi>10.1021/jm015568c</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2002-02, Vol.45 (4), p.753-757 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Benzamides - chemical synthesis Benzamides - chemistry Benzamides - pharmacology Biological and medical sciences Cyclin-Dependent Kinase Inhibitor p21 Cyclins - metabolism Drug Screening Assays, Antitumor Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology General aspects Histone Deacetylase Inhibitors Humans Hydroxamic Acids - chemical synthesis Hydroxamic Acids - chemistry Hydroxamic Acids - pharmacology Hydroxylamines - chemical synthesis Hydroxylamines - chemistry Hydroxylamines - pharmacology Medical sciences Models, Molecular Pharmacology. Drug treatments Promoter Regions, Genetic Structure-Activity Relationship Tumor Cells, Cultured |
| title | Inhibitors of Human Histone Deacetylase: Synthesis and Enzyme and Cellular Activity of Straight Chain Hydroxamates |
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