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Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity
Two series of anhydride modified cantharidin analogues were synthesised and screened for their phosphatase inhibition (PP1 and PP2A) and cytotoxicity in various cancer cell lines ( Ovarian A2780, ADDP; Osteosarcoma 143B; and Colon HCT116 and HT29). One series was synthesised by a novel, high yieldin...
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| Published in: | Bioorganic & medicinal chemistry letters 2000-08, Vol.10 (15), p.1687-1690 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c442t-e412e8be7ee662a500bfe3309b60157ce5b1e5d33d89c9eddfc413b664bc81433 |
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| cites | cdi_FETCH-LOGICAL-c442t-e412e8be7ee662a500bfe3309b60157ce5b1e5d33d89c9eddfc413b664bc81433 |
| container_end_page | 1690 |
| container_issue | 15 |
| container_start_page | 1687 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 10 |
| creator | McCluskey, Adam Bowyer, Michael C Collins, Elizabeth Sim, Alistair T.R Sakoff, Jennette A Baldwin, Monique L |
| description | Two series of anhydride modified cantharidin analogues were synthesised and screened for their phosphatase inhibition (PP1 and PP2A) and cytotoxicity in various cancer cell lines (
Ovarian A2780, ADDP;
Osteosarcoma 143B; and
Colon HCT116 and HT29). One series was synthesised by a novel, high yielding one-pot hydrogenation-ring-opening-esterification procedure, the other by acid catalysed acetal formation. Analogues
5–
7 and
9 displayed moderate PP2A selectivity (ca. 5- to 20-fold) and inhibition typically in the low μM range (comparable, in some cases to cantharidin). The anticancer activity of these analogues varied with the cell line under study; however, many of them showed selective cytotoxicity for the colon tumour cell lines. |
| doi_str_mv | 10.1016/S0960-894X(00)00323-1 |
| format | article |
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Ovarian A2780, ADDP;
Osteosarcoma 143B; and
Colon HCT116 and HT29). One series was synthesised by a novel, high yielding one-pot hydrogenation-ring-opening-esterification procedure, the other by acid catalysed acetal formation. Analogues
5–
7 and
9 displayed moderate PP2A selectivity (ca. 5- to 20-fold) and inhibition typically in the low μM range (comparable, in some cases to cantharidin). The anticancer activity of these analogues varied with the cell line under study; however, many of them showed selective cytotoxicity for the colon tumour cell lines.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(00)00323-1</identifier><identifier>PMID: 10937725</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Anhydrides - chemistry ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cantharidin - analogs & derivatives ; Cantharidin - chemical synthesis ; Cantharidin - pharmacology ; Drug Screening Assays, Antitumor ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; General aspects ; Humans ; Isoenzymes - antagonists & inhibitors ; Medical sciences ; Pharmacology. Drug treatments ; Phosphoprotein Phosphatases - antagonists & inhibitors ; Tumor Cells, Cultured</subject><ispartof>Bioorganic & medicinal chemistry letters, 2000-08, Vol.10 (15), p.1687-1690</ispartof><rights>2000 Elsevier Science Ltd</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c442t-e412e8be7ee662a500bfe3309b60157ce5b1e5d33d89c9eddfc413b664bc81433</citedby><cites>FETCH-LOGICAL-c442t-e412e8be7ee662a500bfe3309b60157ce5b1e5d33d89c9eddfc413b664bc81433</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1432714$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10937725$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>McCluskey, Adam</creatorcontrib><creatorcontrib>Bowyer, Michael C</creatorcontrib><creatorcontrib>Collins, Elizabeth</creatorcontrib><creatorcontrib>Sim, Alistair T.R</creatorcontrib><creatorcontrib>Sakoff, Jennette A</creatorcontrib><creatorcontrib>Baldwin, Monique L</creatorcontrib><title>Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Two series of anhydride modified cantharidin analogues were synthesised and screened for their phosphatase inhibition (PP1 and PP2A) and cytotoxicity in various cancer cell lines (
Ovarian A2780, ADDP;
Osteosarcoma 143B; and
Colon HCT116 and HT29). One series was synthesised by a novel, high yielding one-pot hydrogenation-ring-opening-esterification procedure, the other by acid catalysed acetal formation. Analogues
5–
7 and
9 displayed moderate PP2A selectivity (ca. 5- to 20-fold) and inhibition typically in the low μM range (comparable, in some cases to cantharidin). The anticancer activity of these analogues varied with the cell line under study; however, many of them showed selective cytotoxicity for the colon tumour cell lines.</description><subject>Anhydrides - chemistry</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cantharidin - analogs & derivatives</subject><subject>Cantharidin - chemical synthesis</subject><subject>Cantharidin - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>General aspects</subject><subject>Humans</subject><subject>Isoenzymes - antagonists & inhibitors</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Phosphoprotein Phosphatases - antagonists & inhibitors</subject><subject>Tumor Cells, Cultured</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqFkN9rFDEQx0NR2vPsn1DJgxQFVyeb7K--yFH8BQUftNC3kE1m3ZG9zTXJFe-_N7071DdfMjB8vpOZD2MXAt4KEPW7b9DVULSdunsF8BpAlrIQJ2whVK0KqaB6whZ_kDP2LMafAEKBUqfsTEAnm6asFuzXah53LpBDvvaOBkLHrZnTaHKPZm5mM_kfW4xXPO5yGyPFN5zmkXpK5GfuB74JPmFmN6OPm9EkEzFykaOOl6t9yQMpT7UYuLGJHijtnrOng5kinh_rkt1-_PD9-nNx8_XTl-vVTWGVKlOBSpTY9tgg1nVpKoB-QCmh62sQVWOx6gVWTkrXdrZD5warhOzrWvW2FUrKJbs8zM1b3uc7kl5TtDhNZka_jboRjZKqrTJYHUAbfIwBB70JtDZhpwXoR-V6r1w_-tQAeq9ci5x7cfxg26_R_ZM6OM7AyyNgojXTELIIin85JcsmP0v2_oBhtvFAGHS0hNmZo4A2aefpP5v8BsqOn6w</recordid><startdate>20000807</startdate><enddate>20000807</enddate><creator>McCluskey, Adam</creator><creator>Bowyer, Michael C</creator><creator>Collins, Elizabeth</creator><creator>Sim, Alistair T.R</creator><creator>Sakoff, Jennette A</creator><creator>Baldwin, Monique L</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>20000807</creationdate><title>Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity</title><author>McCluskey, Adam ; Bowyer, Michael C ; Collins, Elizabeth ; Sim, Alistair T.R ; Sakoff, Jennette A ; Baldwin, Monique L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c442t-e412e8be7ee662a500bfe3309b60157ce5b1e5d33d89c9eddfc413b664bc81433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Anhydrides - chemistry</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cantharidin - analogs & derivatives</topic><topic>Cantharidin - chemical synthesis</topic><topic>Cantharidin - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>General aspects</topic><topic>Humans</topic><topic>Isoenzymes - antagonists & inhibitors</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Phosphoprotein Phosphatases - antagonists & inhibitors</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McCluskey, Adam</creatorcontrib><creatorcontrib>Bowyer, Michael C</creatorcontrib><creatorcontrib>Collins, Elizabeth</creatorcontrib><creatorcontrib>Sim, Alistair T.R</creatorcontrib><creatorcontrib>Sakoff, Jennette A</creatorcontrib><creatorcontrib>Baldwin, Monique L</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>McCluskey, Adam</au><au>Bowyer, Michael C</au><au>Collins, Elizabeth</au><au>Sim, Alistair T.R</au><au>Sakoff, Jennette A</au><au>Baldwin, Monique L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2000-08-07</date><risdate>2000</risdate><volume>10</volume><issue>15</issue><spage>1687</spage><epage>1690</epage><pages>1687-1690</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Two series of anhydride modified cantharidin analogues were synthesised and screened for their phosphatase inhibition (PP1 and PP2A) and cytotoxicity in various cancer cell lines (
Ovarian A2780, ADDP;
Osteosarcoma 143B; and
Colon HCT116 and HT29). One series was synthesised by a novel, high yielding one-pot hydrogenation-ring-opening-esterification procedure, the other by acid catalysed acetal formation. Analogues
5–
7 and
9 displayed moderate PP2A selectivity (ca. 5- to 20-fold) and inhibition typically in the low μM range (comparable, in some cases to cantharidin). The anticancer activity of these analogues varied with the cell line under study; however, many of them showed selective cytotoxicity for the colon tumour cell lines.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>10937725</pmid><doi>10.1016/S0960-894X(00)00323-1</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2000-08, Vol.10 (15), p.1687-1690 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | Elsevier |
| subjects | Anhydrides - chemistry Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Biological and medical sciences Cantharidin - analogs & derivatives Cantharidin - chemical synthesis Cantharidin - pharmacology Drug Screening Assays, Antitumor Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology General aspects Humans Isoenzymes - antagonists & inhibitors Medical sciences Pharmacology. Drug treatments Phosphoprotein Phosphatases - antagonists & inhibitors Tumor Cells, Cultured |
| title | Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity |
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