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Mimicking the biological activity of diazobenzo[ b]fluorene natural products with electronically tuned diazofluorene analogs
The synthesis, DNA cleaving, and anti-proliferative properties of electronically modulated diazofluorenes are reported. Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cle...
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| Published in: | Bioorganic & medicinal chemistry letters 2006-10, Vol.16 (19), p.5148-5151 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c415t-d3e4a61ddfa6ac970e80fbd6ec3d3e1531a11c095676db3c2d9b98ec5aaced8d3 |
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| cites | cdi_FETCH-LOGICAL-c415t-d3e4a61ddfa6ac970e80fbd6ec3d3e1531a11c095676db3c2d9b98ec5aaced8d3 |
| container_end_page | 5151 |
| container_issue | 19 |
| container_start_page | 5148 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 16 |
| creator | Zeng, Wei Eric Ballard, T. Tkachenko, Alexander G. Burns, Virginia A. Feldheim, Daniel L. Melander, Christian |
| description | The synthesis, DNA cleaving, and anti-proliferative properties of electronically modulated diazofluorenes are reported.
Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells. |
| doi_str_mv | 10.1016/j.bmcl.2006.07.024 |
| format | article |
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Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2006.07.024</identifier><identifier>PMID: 16870443</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Antiproliferative activity ; Biological and medical sciences ; Carbazoles - pharmacology ; Cell Proliferation - drug effects ; Diazofluorenes ; DNA cleavage ; DNA Damage - drug effects ; Fluorenes - chemical synthesis ; Fluorenes - pharmacology ; General aspects ; HeLa Cells ; Humans ; Kinamycins ; Lomaiviticins ; Medical sciences ; Molecular Mimicry ; Pharmacology. Drug treatments ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-10, Vol.16 (19), p.5148-5151</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-d3e4a61ddfa6ac970e80fbd6ec3d3e1531a11c095676db3c2d9b98ec5aaced8d3</citedby><cites>FETCH-LOGICAL-c415t-d3e4a61ddfa6ac970e80fbd6ec3d3e1531a11c095676db3c2d9b98ec5aaced8d3</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=18066692$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16870443$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zeng, Wei</creatorcontrib><creatorcontrib>Eric Ballard, T.</creatorcontrib><creatorcontrib>Tkachenko, Alexander G.</creatorcontrib><creatorcontrib>Burns, Virginia A.</creatorcontrib><creatorcontrib>Feldheim, Daniel L.</creatorcontrib><creatorcontrib>Melander, Christian</creatorcontrib><title>Mimicking the biological activity of diazobenzo[ b]fluorene natural products with electronically tuned diazofluorene analogs</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The synthesis, DNA cleaving, and anti-proliferative properties of electronically modulated diazofluorenes are reported.
Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferative activity</subject><subject>Biological and medical sciences</subject><subject>Carbazoles - pharmacology</subject><subject>Cell Proliferation - drug effects</subject><subject>Diazofluorenes</subject><subject>DNA cleavage</subject><subject>DNA Damage - drug effects</subject><subject>Fluorenes - chemical synthesis</subject><subject>Fluorenes - pharmacology</subject><subject>General aspects</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Kinamycins</subject><subject>Lomaiviticins</subject><subject>Medical sciences</subject><subject>Molecular Mimicry</subject><subject>Pharmacology. 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Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16870443</pmid><doi>10.1016/j.bmcl.2006.07.024</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2006-10, Vol.16 (19), p.5148-5151 |
| issn | 0960-894X 1464-3405 |
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| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Antiproliferative activity Biological and medical sciences Carbazoles - pharmacology Cell Proliferation - drug effects Diazofluorenes DNA cleavage DNA Damage - drug effects Fluorenes - chemical synthesis Fluorenes - pharmacology General aspects HeLa Cells Humans Kinamycins Lomaiviticins Medical sciences Molecular Mimicry Pharmacology. Drug treatments Structure-Activity Relationship |
| title | Mimicking the biological activity of diazobenzo[ b]fluorene natural products with electronically tuned diazofluorene analogs |
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