Syntheses and Biological Activity of Amamistatin B and Analogs
Amamistatins A and B, natural products isolated from a strain of Nocardia, showed growth inhibition against three human tumor cell lines (IC50 0.24−0.56 μM). Structurally related mycobactins affect the growth of both mycobacterial and human cells through interference with iron chelation. To further...
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| Veröffentlicht in: | Journal of organic chemistry 2008-02, Vol.73 (3), p.1018-1024 |
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| creator | Fennell, Kelley A Möllmann, Ute Miller, Marvin J |
| description | Amamistatins A and B, natural products isolated from a strain of Nocardia, showed growth inhibition against three human tumor cell lines (IC50 0.24−0.56 μM). Structurally related mycobactins affect the growth of both mycobacterial and human cells through interference with iron chelation. To further probe the biological activity of this class of compounds, the total syntheses of amamistatin B and two analogs were completed, and the synthetic samples were screened for tumor cell growth inhibition, HDAC inhibition, and Mycobacterium tuberculosis growth inhibition. Amamistatin B (15) and diastereomer 18 were both active against MCF-7 cells (IC50 0.12−0.20 μM), and less so against PC-3 cells (IC50 8−13 μM). Amamistatin B only moderately inhibited the growth of M. tuberculosis (MIC 47 μM) but showed growth promotion of Mycobacterium smegmatis and other bacteria. |
| doi_str_mv | 10.1021/jo7020532 |
| format | Article |
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Structurally related mycobactins affect the growth of both mycobacterial and human cells through interference with iron chelation. To further probe the biological activity of this class of compounds, the total syntheses of amamistatin B and two analogs were completed, and the synthetic samples were screened for tumor cell growth inhibition, HDAC inhibition, and Mycobacterium tuberculosis growth inhibition. Amamistatin B (15) and diastereomer 18 were both active against MCF-7 cells (IC50 0.12−0.20 μM), and less so against PC-3 cells (IC50 8−13 μM). Amamistatin B only moderately inhibited the growth of M. tuberculosis (MIC 47 μM) but showed growth promotion of Mycobacterium smegmatis and other bacteria.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo7020532</identifier><identifier>PMID: 18173285</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cercopithecus aethiops ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Humans ; Hydroxamic Acids - chemistry ; Inhibitory Concentration 50 ; Microbial Viability - drug effects ; Molecular Structure ; Oligopeptides - chemical synthesis ; Oligopeptides - chemistry ; Oligopeptides - pharmacology ; Organic chemistry ; Oxazoles - chemical synthesis ; Oxazoles - chemistry ; Oxazoles - pharmacology ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2008-02, Vol.73 (3), p.1018-1024</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-33a1d373fbf07b0f95c6b011763675d05e0997f4c1d490a734ec7759214f58303</citedby><cites>FETCH-LOGICAL-a381t-33a1d373fbf07b0f95c6b011763675d05e0997f4c1d490a734ec7759214f58303</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/jo7020532$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo7020532$$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=20047512$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18173285$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fennell, Kelley A</creatorcontrib><creatorcontrib>Möllmann, Ute</creatorcontrib><creatorcontrib>Miller, Marvin J</creatorcontrib><title>Syntheses and Biological Activity of Amamistatin B and Analogs</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Amamistatins A and B, natural products isolated from a strain of Nocardia, showed growth inhibition against three human tumor cell lines (IC50 0.24−0.56 μM). Structurally related mycobactins affect the growth of both mycobacterial and human cells through interference with iron chelation. To further probe the biological activity of this class of compounds, the total syntheses of amamistatin B and two analogs were completed, and the synthetic samples were screened for tumor cell growth inhibition, HDAC inhibition, and Mycobacterium tuberculosis growth inhibition. Amamistatin B (15) and diastereomer 18 were both active against MCF-7 cells (IC50 0.12−0.20 μM), and less so against PC-3 cells (IC50 8−13 μM). Amamistatin B only moderately inhibited the growth of M. tuberculosis (MIC 47 μM) but showed growth promotion of Mycobacterium smegmatis and other bacteria.</description><subject>Animals</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cercopithecus aethiops</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Humans</subject><subject>Hydroxamic Acids - chemistry</subject><subject>Inhibitory Concentration 50</subject><subject>Microbial Viability - drug effects</subject><subject>Molecular Structure</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Oligopeptides - chemistry</subject><subject>Oligopeptides - pharmacology</subject><subject>Organic chemistry</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - chemistry</subject><subject>Oxazoles - pharmacology</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9LwzAYBvAgipvTg19AevHgofomaZrmInTDfzBQ2ATxEtI00cy1HU0n7tububFdzOU95MfD-z4InWO4xkDwzazhQIBRcoD6mBGIUwHJIeoDEBJTktIeOvF-BuExxo5RD2eYU5KxPrqdrOru03jjI1WX0dA18-bDaTWPct25b9etosZGeaUq5zvVuToa_sG8VgH6U3Rk1dybs-0coNf7u-noMR4_PzyN8nGsaIa7mFKFS8qpLSzwAqxgOi0AY57SlLMSmAEhuE00LhMBitPEaM6ZIDixLKNAB-hqk6vbxvvWWLloXaXalcQg1x3IXQfBXmzsYllUptzL7dEBXG6B8uFS26paO79zBCDhDK-D4o0Lp5uf3b9qv2TKKWdy-jKR06FgYxDv8m2fq7QP-yzb0JH_Z8FfnfF72A</recordid><startdate>20080201</startdate><enddate>20080201</enddate><creator>Fennell, Kelley A</creator><creator>Möllmann, Ute</creator><creator>Miller, Marvin J</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></search><sort><creationdate>20080201</creationdate><title>Syntheses and Biological Activity of Amamistatin B and Analogs</title><author>Fennell, Kelley A ; Möllmann, Ute ; Miller, Marvin J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-33a1d373fbf07b0f95c6b011763675d05e0997f4c1d490a734ec7759214f58303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Animals</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cercopithecus aethiops</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Humans</topic><topic>Hydroxamic Acids - chemistry</topic><topic>Inhibitory Concentration 50</topic><topic>Microbial Viability - drug effects</topic><topic>Molecular Structure</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Oligopeptides - chemistry</topic><topic>Oligopeptides - pharmacology</topic><topic>Organic chemistry</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - chemistry</topic><topic>Oxazoles - pharmacology</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fennell, Kelley A</creatorcontrib><creatorcontrib>Möllmann, Ute</creatorcontrib><creatorcontrib>Miller, Marvin J</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><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fennell, Kelley A</au><au>Möllmann, Ute</au><au>Miller, Marvin J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and Biological Activity of Amamistatin B and Analogs</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-02-01</date><risdate>2008</risdate><volume>73</volume><issue>3</issue><spage>1018</spage><epage>1024</epage><pages>1018-1024</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Amamistatins A and B, natural products isolated from a strain of Nocardia, showed growth inhibition against three human tumor cell lines (IC50 0.24−0.56 μM). Structurally related mycobactins affect the growth of both mycobacterial and human cells through interference with iron chelation. To further probe the biological activity of this class of compounds, the total syntheses of amamistatin B and two analogs were completed, and the synthetic samples were screened for tumor cell growth inhibition, HDAC inhibition, and Mycobacterium tuberculosis growth inhibition. Amamistatin B (15) and diastereomer 18 were both active against MCF-7 cells (IC50 0.12−0.20 μM), and less so against PC-3 cells (IC50 8−13 μM). Amamistatin B only moderately inhibited the growth of M. tuberculosis (MIC 47 μM) but showed growth promotion of Mycobacterium smegmatis and other bacteria.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18173285</pmid><doi>10.1021/jo7020532</doi><tpages>7</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Animals Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Cercopithecus aethiops Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Humans Hydroxamic Acids - chemistry Inhibitory Concentration 50 Microbial Viability - drug effects Molecular Structure Oligopeptides - chemical synthesis Oligopeptides - chemistry Oligopeptides - pharmacology Organic chemistry Oxazoles - chemical synthesis Oxazoles - chemistry Oxazoles - pharmacology Preparations and properties |
| title | Syntheses and Biological Activity of Amamistatin B and Analogs |
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