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Thiocamptothecin
The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Me...
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| Published in: | Journal of medicinal chemistry 2008-05, Vol.51 (10), p.3040-3044 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a381t-a0be6a84c5de67609f7d011d7531c17ed10bf52f6bf9f644888cf1da3de842ed3 |
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| cites | cdi_FETCH-LOGICAL-a381t-a0be6a84c5de67609f7d011d7531c17ed10bf52f6bf9f644888cf1da3de842ed3 |
| container_end_page | 3044 |
| container_issue | 10 |
| container_start_page | 3040 |
| container_title | Journal of medicinal chemistry |
| container_volume | 51 |
| creator | Samorì, Cristian Guerrini, Andrea Varchi, Greta Zunino, Franco Beretta, Giovanni Luca Femoni, Cristina Bombardelli, Ezio Fontana, Gabriele Battaglia, Arturo |
| description | The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound. |
| doi_str_mv | 10.1021/jm8001982 |
| format | article |
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The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm8001982</identifier><identifier>PMID: 18419110</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 ; Biological and medical sciences ; Camptothecin - analogs & derivatives ; Camptothecin - chemical synthesis ; Camptothecin - chemistry ; Camptothecin - pharmacology ; Cell Line, Tumor ; Crystallography, X-Ray ; DNA Damage ; DNA Topoisomerases, Type I - chemistry ; General aspects ; Humans ; Medical sciences ; Models, Molecular ; Pharmacology. Drug treatments ; Thiones - chemical synthesis ; Thiones - chemistry ; Thiones - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2008-05, Vol.51 (10), p.3040-3044</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-a0be6a84c5de67609f7d011d7531c17ed10bf52f6bf9f644888cf1da3de842ed3</citedby><cites>FETCH-LOGICAL-a381t-a0be6a84c5de67609f7d011d7531c17ed10bf52f6bf9f644888cf1da3de842ed3</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=20349464$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18419110$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Samorì, Cristian</creatorcontrib><creatorcontrib>Guerrini, Andrea</creatorcontrib><creatorcontrib>Varchi, Greta</creatorcontrib><creatorcontrib>Zunino, Franco</creatorcontrib><creatorcontrib>Beretta, Giovanni Luca</creatorcontrib><creatorcontrib>Femoni, Cristina</creatorcontrib><creatorcontrib>Bombardelli, Ezio</creatorcontrib><creatorcontrib>Fontana, Gabriele</creatorcontrib><creatorcontrib>Battaglia, Arturo</creatorcontrib><title>Thiocamptothecin</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Camptothecin - analogs & derivatives</subject><subject>Camptothecin - chemical synthesis</subject><subject>Camptothecin - chemistry</subject><subject>Camptothecin - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Crystallography, X-Ray</subject><subject>DNA Damage</subject><subject>DNA Topoisomerases, Type I - chemistry</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. 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Drug treatments</topic><topic>Thiones - chemical synthesis</topic><topic>Thiones - chemistry</topic><topic>Thiones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Samorì, Cristian</creatorcontrib><creatorcontrib>Guerrini, Andrea</creatorcontrib><creatorcontrib>Varchi, Greta</creatorcontrib><creatorcontrib>Zunino, Franco</creatorcontrib><creatorcontrib>Beretta, Giovanni Luca</creatorcontrib><creatorcontrib>Femoni, Cristina</creatorcontrib><creatorcontrib>Bombardelli, Ezio</creatorcontrib><creatorcontrib>Fontana, Gabriele</creatorcontrib><creatorcontrib>Battaglia, Arturo</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>Samorì, Cristian</au><au>Guerrini, Andrea</au><au>Varchi, Greta</au><au>Zunino, Franco</au><au>Beretta, Giovanni Luca</au><au>Femoni, Cristina</au><au>Bombardelli, Ezio</au><au>Fontana, Gabriele</au><au>Battaglia, Arturo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiocamptothecin</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2008-05-22</date><risdate>2008</risdate><volume>51</volume><issue>10</issue><spage>3040</spage><epage>3044</epage><pages>3040-3044</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18419110</pmid><doi>10.1021/jm8001982</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2008-05, Vol.51 (10), p.3040-3044 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Camptothecin - analogs & derivatives Camptothecin - chemical synthesis Camptothecin - chemistry Camptothecin - pharmacology Cell Line, Tumor Crystallography, X-Ray DNA Damage DNA Topoisomerases, Type I - chemistry General aspects Humans Medical sciences Models, Molecular Pharmacology. Drug treatments Thiones - chemical synthesis Thiones - chemistry Thiones - pharmacology |
| title | Thiocamptothecin |
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