Design, Synthesis, and Anticancer Properties of Novel Benzophenone-Conjugated Coumarin Analogs
In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a–o) bearing the coumarin...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2013-12, Vol.346 (12), p.901-911 |
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| creator | Lakshmi Ranganatha, V. Zameer, Farhan Meghashri, S. Rekha, N. D. Girish, V. Gurupadaswamy, H. D. Khanum, Shaukath Ara |
| description | In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a–o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation‐7 (MCF‐7) and Ehrlich's ascites tumor (EAT) cell lines and their biomarkers, followed by in silico studies regarding phosphoinositide 3‐kinase (PI3K) and caspase by molecular docking. Benzophenones have been reported as potential drugs targeting tumor angiogenesis; thus, the formation of neovessels in an in vivo model system like CAM, which is angiogenesis dependent, was observed in the presence of compounds 8a–o. The above findings would help in understanding their putative potential as therapeutic agents for cancer patients.
Coumarin‐integrated benzophenone conjugates (8a–o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF‐7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3‐kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system. |
| doi_str_mv | 10.1002/ardp.201300298 |
| format | Article |
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Coumarin‐integrated benzophenone conjugates (8a–o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF‐7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3‐kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.201300298</identifier><identifier>PMID: 24170414</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Angiogenesis ; Angiogenesis Inhibitors - chemical synthesis ; Angiogenesis Inhibitors - pharmacology ; Animals ; Anticancer agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Benzophenone ; Benzophenones - chemical synthesis ; Benzophenones - pharmacology ; CAM ; Cancer ; Carcinoma, Ehrlich Tumor - metabolism ; Carcinoma, Ehrlich Tumor - pathology ; Caspase ; Caspase Inhibitors - chemical synthesis ; Caspase Inhibitors - pharmacology ; Caspases - chemistry ; Caspases - metabolism ; Cell Proliferation - drug effects ; Chick Embryo ; Coumarin ; Coumarins - chemical synthesis ; Coumarins - pharmacology ; Drug Design ; Humans ; Inhibitory Concentration 50 ; MCF-7 Cells ; Medical research ; Mice ; Models, Molecular ; Molecular Docking Simulation ; Molecular Structure ; Neovascularization, Physiologic - drug effects ; Phosphatidylinositol 3-Kinase - chemistry ; Phosphatidylinositol 3-Kinase - metabolism ; PI3K ; Protein Conformation ; Signal Transduction - drug effects ; Structure-activity relation (SAR) ; Structure-Activity Relationship</subject><ispartof>Archiv der Pharmazie (Weinheim), 2013-12, Vol.346 (12), p.901-911</ispartof><rights>2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4118-ead83e3e7235006a7d9310dc42bc4408fcecec666bfbe91c6921945a6ca5e7713</citedby><cites>FETCH-LOGICAL-c4118-ead83e3e7235006a7d9310dc42bc4408fcecec666bfbe91c6921945a6ca5e7713</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.201300298$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.201300298$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24170414$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lakshmi Ranganatha, V.</creatorcontrib><creatorcontrib>Zameer, Farhan</creatorcontrib><creatorcontrib>Meghashri, S.</creatorcontrib><creatorcontrib>Rekha, N. D.</creatorcontrib><creatorcontrib>Girish, V.</creatorcontrib><creatorcontrib>Gurupadaswamy, H. D.</creatorcontrib><creatorcontrib>Khanum, Shaukath Ara</creatorcontrib><title>Design, Synthesis, and Anticancer Properties of Novel Benzophenone-Conjugated Coumarin Analogs</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><description>In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a–o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation‐7 (MCF‐7) and Ehrlich's ascites tumor (EAT) cell lines and their biomarkers, followed by in silico studies regarding phosphoinositide 3‐kinase (PI3K) and caspase by molecular docking. Benzophenones have been reported as potential drugs targeting tumor angiogenesis; thus, the formation of neovessels in an in vivo model system like CAM, which is angiogenesis dependent, was observed in the presence of compounds 8a–o. The above findings would help in understanding their putative potential as therapeutic agents for cancer patients.
Coumarin‐integrated benzophenone conjugates (8a–o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF‐7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3‐kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system.</description><subject>Angiogenesis</subject><subject>Angiogenesis Inhibitors - chemical synthesis</subject><subject>Angiogenesis Inhibitors - pharmacology</subject><subject>Animals</subject><subject>Anticancer agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Benzophenone</subject><subject>Benzophenones - chemical synthesis</subject><subject>Benzophenones - pharmacology</subject><subject>CAM</subject><subject>Cancer</subject><subject>Carcinoma, Ehrlich Tumor - metabolism</subject><subject>Carcinoma, Ehrlich Tumor - pathology</subject><subject>Caspase</subject><subject>Caspase Inhibitors - chemical synthesis</subject><subject>Caspase Inhibitors - pharmacology</subject><subject>Caspases - chemistry</subject><subject>Caspases - metabolism</subject><subject>Cell Proliferation - drug effects</subject><subject>Chick Embryo</subject><subject>Coumarin</subject><subject>Coumarins - chemical synthesis</subject><subject>Coumarins - pharmacology</subject><subject>Drug Design</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>MCF-7 Cells</subject><subject>Medical research</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Neovascularization, Physiologic - drug effects</subject><subject>Phosphatidylinositol 3-Kinase - chemistry</subject><subject>Phosphatidylinositol 3-Kinase - metabolism</subject><subject>PI3K</subject><subject>Protein Conformation</subject><subject>Signal Transduction - drug effects</subject><subject>Structure-activity relation (SAR)</subject><subject>Structure-Activity Relationship</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1v1DAQxS0EokvhyhFF4sKhWcYfsZPjkqWlUlUqPm9YXmeyzZK1g50Ay19fly0rxAXNYWak33uaeYQ8pTCnAOylCc0wZ0B5WqryHpnRgtFc0FLcJzPgssgl4_yIPIpxAwAcWPGQHDFBFQgqZuTLEmO3difZ-50br9McTzLjmmzhxs4aZzFkV8EPGMYOY-bb7NJ_xz57he6XH67ReYd57d1mWpsRm6z209aEziW96f06PiYPWtNHfHLXj8nH09cf6jf5xduz83pxkVtBaZmjaUqOHBXjBYA0qqk4hcYKtrJCQNlaTCWlXLUrrKiVFaOVKIy0pkClKD8mL_a-Q_DfJoyj3nbRYt8bh36KmgpZUKW4lAl9_g-68VNI5_6mOCgOFSRqvqds8DEGbPUQuvTaTlPQt8nr2-T1IfkkeHZnO6222BzwP1EnoNoDP7oed_-x04t3y6u_zfO9tosj_jxoTfiqpeKq0J8vz_Tpp2WtBON6yW8A5iyeQQ</recordid><startdate>201312</startdate><enddate>201312</enddate><creator>Lakshmi Ranganatha, V.</creator><creator>Zameer, Farhan</creator><creator>Meghashri, S.</creator><creator>Rekha, N. D.</creator><creator>Girish, V.</creator><creator>Gurupadaswamy, H. D.</creator><creator>Khanum, Shaukath Ara</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>K9.</scope><scope>7X8</scope></search><sort><creationdate>201312</creationdate><title>Design, Synthesis, and Anticancer Properties of Novel Benzophenone-Conjugated Coumarin Analogs</title><author>Lakshmi Ranganatha, V. ; Zameer, Farhan ; Meghashri, S. ; Rekha, N. D. ; Girish, V. ; Gurupadaswamy, H. D. ; Khanum, Shaukath Ara</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4118-ead83e3e7235006a7d9310dc42bc4408fcecec666bfbe91c6921945a6ca5e7713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Angiogenesis</topic><topic>Angiogenesis Inhibitors - chemical synthesis</topic><topic>Angiogenesis Inhibitors - pharmacology</topic><topic>Animals</topic><topic>Anticancer agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis - drug effects</topic><topic>Benzophenone</topic><topic>Benzophenones - chemical synthesis</topic><topic>Benzophenones - pharmacology</topic><topic>CAM</topic><topic>Cancer</topic><topic>Carcinoma, Ehrlich Tumor - metabolism</topic><topic>Carcinoma, Ehrlich Tumor - pathology</topic><topic>Caspase</topic><topic>Caspase Inhibitors - chemical synthesis</topic><topic>Caspase Inhibitors - pharmacology</topic><topic>Caspases - chemistry</topic><topic>Caspases - metabolism</topic><topic>Cell Proliferation - drug effects</topic><topic>Chick Embryo</topic><topic>Coumarin</topic><topic>Coumarins - chemical synthesis</topic><topic>Coumarins - pharmacology</topic><topic>Drug Design</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>MCF-7 Cells</topic><topic>Medical research</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Neovascularization, Physiologic - drug effects</topic><topic>Phosphatidylinositol 3-Kinase - chemistry</topic><topic>Phosphatidylinositol 3-Kinase - metabolism</topic><topic>PI3K</topic><topic>Protein Conformation</topic><topic>Signal Transduction - drug effects</topic><topic>Structure-activity relation (SAR)</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lakshmi Ranganatha, V.</creatorcontrib><creatorcontrib>Zameer, Farhan</creatorcontrib><creatorcontrib>Meghashri, S.</creatorcontrib><creatorcontrib>Rekha, N. D.</creatorcontrib><creatorcontrib>Girish, V.</creatorcontrib><creatorcontrib>Gurupadaswamy, H. D.</creatorcontrib><creatorcontrib>Khanum, Shaukath Ara</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lakshmi Ranganatha, V.</au><au>Zameer, Farhan</au><au>Meghashri, S.</au><au>Rekha, N. D.</au><au>Girish, V.</au><au>Gurupadaswamy, H. D.</au><au>Khanum, Shaukath Ara</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis, and Anticancer Properties of Novel Benzophenone-Conjugated Coumarin Analogs</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><date>2013-12</date><risdate>2013</risdate><volume>346</volume><issue>12</issue><spage>901</spage><epage>911</epage><pages>901-911</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a–o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation‐7 (MCF‐7) and Ehrlich's ascites tumor (EAT) cell lines and their biomarkers, followed by in silico studies regarding phosphoinositide 3‐kinase (PI3K) and caspase by molecular docking. Benzophenones have been reported as potential drugs targeting tumor angiogenesis; thus, the formation of neovessels in an in vivo model system like CAM, which is angiogenesis dependent, was observed in the presence of compounds 8a–o. The above findings would help in understanding their putative potential as therapeutic agents for cancer patients.
Coumarin‐integrated benzophenone conjugates (8a–o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF‐7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3‐kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>24170414</pmid><doi>10.1002/ardp.201300298</doi><tpages>11</tpages></addata></record> |
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| ispartof | Archiv der Pharmazie (Weinheim), 2013-12, Vol.346 (12), p.901-911 |
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| subjects | Angiogenesis Angiogenesis Inhibitors - chemical synthesis Angiogenesis Inhibitors - pharmacology Animals Anticancer agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Apoptosis - drug effects Benzophenone Benzophenones - chemical synthesis Benzophenones - pharmacology CAM Cancer Carcinoma, Ehrlich Tumor - metabolism Carcinoma, Ehrlich Tumor - pathology Caspase Caspase Inhibitors - chemical synthesis Caspase Inhibitors - pharmacology Caspases - chemistry Caspases - metabolism Cell Proliferation - drug effects Chick Embryo Coumarin Coumarins - chemical synthesis Coumarins - pharmacology Drug Design Humans Inhibitory Concentration 50 MCF-7 Cells Medical research Mice Models, Molecular Molecular Docking Simulation Molecular Structure Neovascularization, Physiologic - drug effects Phosphatidylinositol 3-Kinase - chemistry Phosphatidylinositol 3-Kinase - metabolism PI3K Protein Conformation Signal Transduction - drug effects Structure-activity relation (SAR) Structure-Activity Relationship |
| title | Design, Synthesis, and Anticancer Properties of Novel Benzophenone-Conjugated Coumarin Analogs |
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