Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy
Iron chelators have emerged as a potential anti-cancer treatment strategy. In this study, a series of novel thiosemicarbazone iron chelators containing a quinoline scaffold were synthesized and characterized. A number of analogs show markedly greater anti-cancer activity than the ‘gold-standard’ iro...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2012-09, Vol.22 (17), p.5527-5531 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Serda, Maciej Kalinowski, Danuta S. Mrozek-Wilczkiewicz, Anna Musiol, Robert Szurko, Agnieszka Ratuszna, Alicja Pantarat, Namfon Kovacevic, Zaklina Merlot, Angelica M. Richardson, Des R. Polanski, Jaroslaw |
| description | Iron chelators have emerged as a potential anti-cancer treatment strategy. In this study, a series of novel thiosemicarbazone iron chelators containing a quinoline scaffold were synthesized and characterized. A number of analogs show markedly greater anti-cancer activity than the ‘gold-standard’ iron chelator, desferrioxamine. The anti-proliferative activity and iron chelation efficacy of several of these ligands (especially compound 1b), indicates that further investigation of this class of thiosemicarbazones is worthwhile. |
| doi_str_mv | 10.1016/j.bmcl.2012.07.030 |
| format | Article |
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In this study, a series of novel thiosemicarbazone iron chelators containing a quinoline scaffold were synthesized and characterized. A number of analogs show markedly greater anti-cancer activity than the ‘gold-standard’ iron chelator, desferrioxamine. The anti-proliferative activity and iron chelation efficacy of several of these ligands (especially compound 1b), indicates that further investigation of this class of thiosemicarbazones is worthwhile.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.07.030</identifier><identifier>PMID: 22858101</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anti-tumor activity ; anticarcinogenic activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Chelating agents ; Chelation ; Deferoxamine ; Deferoxamine - pharmacology ; Desferrioxamine ; Humans ; Iron ; Iron - metabolism ; Iron Chelating Agents - chemical synthesis ; Iron Chelating Agents - chemistry ; Iron Chelating Agents - pharmacology ; Iron chelation ; Medical sciences ; Neoplasms - drug therapy ; Neoplasms - metabolism ; Pharmacology. Drug treatments ; quinoline ; Quinolines ; Quinolines - chemical synthesis ; Quinolines - chemistry ; Quinolines - pharmacology ; scaffolds ; Thiosemicarbazones - chemical synthesis ; Thiosemicarbazones - chemistry ; Thiosemicarbazones - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-09, Vol.22 (17), p.5527-5531</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c509t-596e81f401d11b98eea89d54d7341afe52a98cc630ac5f2ad73fa3ab122ee1b63</citedby><cites>FETCH-LOGICAL-c509t-596e81f401d11b98eea89d54d7341afe52a98cc630ac5f2ad73fa3ab122ee1b63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2012.07.030$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27911,27912,45982</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26340366$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22858101$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Serda, Maciej</creatorcontrib><creatorcontrib>Kalinowski, Danuta S.</creatorcontrib><creatorcontrib>Mrozek-Wilczkiewicz, Anna</creatorcontrib><creatorcontrib>Musiol, Robert</creatorcontrib><creatorcontrib>Szurko, Agnieszka</creatorcontrib><creatorcontrib>Ratuszna, Alicja</creatorcontrib><creatorcontrib>Pantarat, Namfon</creatorcontrib><creatorcontrib>Kovacevic, Zaklina</creatorcontrib><creatorcontrib>Merlot, Angelica M.</creatorcontrib><creatorcontrib>Richardson, Des R.</creatorcontrib><creatorcontrib>Polanski, Jaroslaw</creatorcontrib><title>Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Iron chelators have emerged as a potential anti-cancer treatment strategy. In this study, a series of novel thiosemicarbazone iron chelators containing a quinoline scaffold were synthesized and characterized. A number of analogs show markedly greater anti-cancer activity than the ‘gold-standard’ iron chelator, desferrioxamine. The anti-proliferative activity and iron chelation efficacy of several of these ligands (especially compound 1b), indicates that further investigation of this class of thiosemicarbazones is worthwhile.</description><subject>Anti-tumor activity</subject><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Chelating agents</subject><subject>Chelation</subject><subject>Deferoxamine</subject><subject>Deferoxamine - pharmacology</subject><subject>Desferrioxamine</subject><subject>Humans</subject><subject>Iron</subject><subject>Iron - metabolism</subject><subject>Iron Chelating Agents - chemical synthesis</subject><subject>Iron Chelating Agents - chemistry</subject><subject>Iron Chelating Agents - pharmacology</subject><subject>Iron chelation</subject><subject>Medical sciences</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>quinoline</subject><subject>Quinolines</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Quinolines - pharmacology</subject><subject>scaffolds</subject><subject>Thiosemicarbazones - chemical synthesis</subject><subject>Thiosemicarbazones - chemistry</subject><subject>Thiosemicarbazones - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkc2KFDEURoMoTjv6Ai60NsJsqs1fpavAjQyOCgMuxgF34VbqZjpNVTKTpISed_CdTdFtuxNXgcv5vtzkEPKa0TWjTL3frfvJjGtOGV_TzZoK-oSsmFSyFpI2T8mKdorWbSd_nJEXKe0oZZJK-Zyccd42belYkV83e5-3mFyqwA-V2UIEkzG6R8gu-CrY6mF2PozOY91DwqHKWxcSTs5A7OExeDxGQ4w4nlIGx3EeIVYuBl_3zg_O31VobcmZfZVDCWVX53kK8TR-SZ5ZGBO-Op7n5Pbq0_fLL_X1t89fLz9e16ahXa6bTmHLrKRsYKzvWkRou6GRw0ZIBhYbDl1rjBIUTGM5lLkFAT3jHJH1SpyTi0PvfQwPM6asJ5eWjcFjmJNmVLSKCsbk_6CyYYryBeUH1MSQUkSr76ObIO4LpBdjeqcXY3oxpulGF2Ml9ObYP_cTDqfIH0UFeHcEIBkYbQRvXPrLqSJbqOVNbw-chaDhLhbm9qbc1BTtomy5KcSHA4Hla386jDoZh97g4CKarIfg_rXpb9TowJU</recordid><startdate>20120901</startdate><enddate>20120901</enddate><creator>Serda, Maciej</creator><creator>Kalinowski, Danuta S.</creator><creator>Mrozek-Wilczkiewicz, Anna</creator><creator>Musiol, Robert</creator><creator>Szurko, Agnieszka</creator><creator>Ratuszna, Alicja</creator><creator>Pantarat, Namfon</creator><creator>Kovacevic, Zaklina</creator><creator>Merlot, Angelica M.</creator><creator>Richardson, Des R.</creator><creator>Polanski, Jaroslaw</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20120901</creationdate><title>Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy</title><author>Serda, Maciej ; Kalinowski, Danuta S. ; Mrozek-Wilczkiewicz, Anna ; Musiol, Robert ; Szurko, Agnieszka ; Ratuszna, Alicja ; Pantarat, Namfon ; Kovacevic, Zaklina ; Merlot, Angelica M. ; Richardson, Des R. ; Polanski, Jaroslaw</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c509t-596e81f401d11b98eea89d54d7341afe52a98cc630ac5f2ad73fa3ab122ee1b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anti-tumor activity</topic><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Chelating agents</topic><topic>Chelation</topic><topic>Deferoxamine</topic><topic>Deferoxamine - pharmacology</topic><topic>Desferrioxamine</topic><topic>Humans</topic><topic>Iron</topic><topic>Iron - metabolism</topic><topic>Iron Chelating Agents - chemical synthesis</topic><topic>Iron Chelating Agents - chemistry</topic><topic>Iron Chelating Agents - pharmacology</topic><topic>Iron chelation</topic><topic>Medical sciences</topic><topic>Neoplasms - drug therapy</topic><topic>Neoplasms - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>quinoline</topic><topic>Quinolines</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - chemistry</topic><topic>Quinolines - pharmacology</topic><topic>scaffolds</topic><topic>Thiosemicarbazones - chemical synthesis</topic><topic>Thiosemicarbazones - chemistry</topic><topic>Thiosemicarbazones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Serda, Maciej</creatorcontrib><creatorcontrib>Kalinowski, Danuta S.</creatorcontrib><creatorcontrib>Mrozek-Wilczkiewicz, Anna</creatorcontrib><creatorcontrib>Musiol, Robert</creatorcontrib><creatorcontrib>Szurko, Agnieszka</creatorcontrib><creatorcontrib>Ratuszna, Alicja</creatorcontrib><creatorcontrib>Pantarat, Namfon</creatorcontrib><creatorcontrib>Kovacevic, Zaklina</creatorcontrib><creatorcontrib>Merlot, Angelica M.</creatorcontrib><creatorcontrib>Richardson, Des R.</creatorcontrib><creatorcontrib>Polanski, Jaroslaw</creatorcontrib><collection>AGRIS</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Serda, Maciej</au><au>Kalinowski, Danuta S.</au><au>Mrozek-Wilczkiewicz, Anna</au><au>Musiol, Robert</au><au>Szurko, Agnieszka</au><au>Ratuszna, Alicja</au><au>Pantarat, Namfon</au><au>Kovacevic, Zaklina</au><au>Merlot, Angelica M.</au><au>Richardson, Des R.</au><au>Polanski, Jaroslaw</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-09-01</date><risdate>2012</risdate><volume>22</volume><issue>17</issue><spage>5527</spage><epage>5531</epage><pages>5527-5531</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Iron chelators have emerged as a potential anti-cancer treatment strategy. In this study, a series of novel thiosemicarbazone iron chelators containing a quinoline scaffold were synthesized and characterized. A number of analogs show markedly greater anti-cancer activity than the ‘gold-standard’ iron chelator, desferrioxamine. The anti-proliferative activity and iron chelation efficacy of several of these ligands (especially compound 1b), indicates that further investigation of this class of thiosemicarbazones is worthwhile.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22858101</pmid><doi>10.1016/j.bmcl.2012.07.030</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2012-09, Vol.22 (17), p.5527-5531 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1038603114 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Anti-tumor activity anticarcinogenic activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Cell Proliferation - drug effects Chelating agents Chelation Deferoxamine Deferoxamine - pharmacology Desferrioxamine Humans Iron Iron - metabolism Iron Chelating Agents - chemical synthesis Iron Chelating Agents - chemistry Iron Chelating Agents - pharmacology Iron chelation Medical sciences Neoplasms - drug therapy Neoplasms - metabolism Pharmacology. Drug treatments quinoline Quinolines Quinolines - chemical synthesis Quinolines - chemistry Quinolines - pharmacology scaffolds Thiosemicarbazones - chemical synthesis Thiosemicarbazones - chemistry Thiosemicarbazones - pharmacology |
| title | Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy |
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