Synthesis, anticancer activity and mitochondrial mediated apoptosis inducing ability of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates
New class of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates have been prepared and evaluated for their anticancer activity. Further, some of the biological assays related to mechanism aspects have also been carried out. A series of 2,5-diaryloxadiazole linked pyrrolo[2,1-c][1,4]benzodiazepine...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2010-09, Vol.18 (18), p.6666-6677 |
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| creator | Kamal, Ahmed Dastagiri, D. Ramaiah, M. Janaki Bharathi, E. Vijaya Reddy, J. Surendranadha Balakishan, G. Sarma, Pranjal Pushpavalli, S.N.C.V.L. Pal-Bhadra, Manika Juvekar, Aarti Sen, Subrata Zingde, Surekha |
| description | New class of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates have been prepared and evaluated for their anticancer activity. Further, some of the biological assays related to mechanism aspects have also been carried out.
A series of 2,5-diaryloxadiazole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates have been prepared and evaluated for their anticancer activity. These conjugates have shown promising activity with GI50 values ranging from |
| doi_str_mv | 10.1016/j.bmc.2010.07.067 |
| format | Article |
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A series of 2,5-diaryloxadiazole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates have been prepared and evaluated for their anticancer activity. These conjugates have shown promising activity with GI50 values ranging from <0.1 to 0.29μΜ. It is observed that some of these conjugates particularly 4a, 4d, 4i and 4l exhibit significant anticancer activity. Some detailed biological assays relating to the cell cycle aspects associated to Bax and caspases have been examined with a view to understand the mechanism of action of these conjugates.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2010.07.067</identifier><identifier>PMID: 20732817</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>2,5-Diaryloxadiazoles ; Animals ; Anticancer activity ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - therapeutic use ; Apoptosis ; bcl-2-Associated X Protein - metabolism ; Benzodiazepines - chemical synthesis ; Benzodiazepines - chemistry ; Benzodiazepines - therapeutic use ; Biological and medical sciences ; Caspases ; Caspases - metabolism ; Cell Cycle - drug effects ; Cell Line, Tumor ; Cyclin dependent kinase-2 (CDK-2) ; Cyclin-Dependent Kinase 2 - metabolism ; General aspects ; Humans ; Male ; Medical sciences ; Mice ; Mice, Inbred NOD ; Miscellaneous ; Mitochondria - drug effects ; Neoplasms - drug therapy ; Oxadiazoles - chemical synthesis ; Oxadiazoles - chemistry ; p53 ; Pharmacology. Drug treatments ; Pyrrolobenzodiazepine ; Tumor Suppressor Protein p53 - metabolism ; Xenograft Model Antitumor Assays</subject><ispartof>Bioorganic & medicinal chemistry, 2010-09, Vol.18 (18), p.6666-6677</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright (c) 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c446t-501f8d67b8f97010def73855faca76c9d0f8f75e9e0f38c1b7dfaa967b1bd68a3</citedby><cites>FETCH-LOGICAL-c446t-501f8d67b8f97010def73855faca76c9d0f8f75e9e0f38c1b7dfaa967b1bd68a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2010.07.067$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23248220$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20732817$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kamal, Ahmed</creatorcontrib><creatorcontrib>Dastagiri, D.</creatorcontrib><creatorcontrib>Ramaiah, M. Janaki</creatorcontrib><creatorcontrib>Bharathi, E. Vijaya</creatorcontrib><creatorcontrib>Reddy, J. Surendranadha</creatorcontrib><creatorcontrib>Balakishan, G.</creatorcontrib><creatorcontrib>Sarma, Pranjal</creatorcontrib><creatorcontrib>Pushpavalli, S.N.C.V.L.</creatorcontrib><creatorcontrib>Pal-Bhadra, Manika</creatorcontrib><creatorcontrib>Juvekar, Aarti</creatorcontrib><creatorcontrib>Sen, Subrata</creatorcontrib><creatorcontrib>Zingde, Surekha</creatorcontrib><title>Synthesis, anticancer activity and mitochondrial mediated apoptosis inducing ability of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>New class of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates have been prepared and evaluated for their anticancer activity. Further, some of the biological assays related to mechanism aspects have also been carried out.
A series of 2,5-diaryloxadiazole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates have been prepared and evaluated for their anticancer activity. These conjugates have shown promising activity with GI50 values ranging from <0.1 to 0.29μΜ. It is observed that some of these conjugates particularly 4a, 4d, 4i and 4l exhibit significant anticancer activity. Some detailed biological assays relating to the cell cycle aspects associated to Bax and caspases have been examined with a view to understand the mechanism of action of these conjugates.</description><subject>2,5-Diaryloxadiazoles</subject><subject>Animals</subject><subject>Anticancer activity</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - therapeutic use</subject><subject>Apoptosis</subject><subject>bcl-2-Associated X Protein - metabolism</subject><subject>Benzodiazepines - chemical synthesis</subject><subject>Benzodiazepines - chemistry</subject><subject>Benzodiazepines - therapeutic use</subject><subject>Biological and medical sciences</subject><subject>Caspases</subject><subject>Caspases - metabolism</subject><subject>Cell Cycle - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cyclin dependent kinase-2 (CDK-2)</subject><subject>Cyclin-Dependent Kinase 2 - metabolism</subject><subject>General aspects</subject><subject>Humans</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred NOD</subject><subject>Miscellaneous</subject><subject>Mitochondria - drug effects</subject><subject>Neoplasms - drug therapy</subject><subject>Oxadiazoles - chemical synthesis</subject><subject>Oxadiazoles - chemistry</subject><subject>p53</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrrolobenzodiazepine</subject><subject>Tumor Suppressor Protein p53 - metabolism</subject><subject>Xenograft Model Antitumor Assays</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkbtuFDEUhi0EIkvgAWjQNIgms9ieGV9EhaJwkSJRALXlsY8Tr2bswfZGbCreIAVvyJPg1S7QAZXto-8_Oj4fQk8JXhNM2MvNepzNmuL6xnyNGb-HVqRnfdt1ktxHKyyZaLGQ7AQ9ynmDMaa9JA_RCcW8o4LwFbr7uAvlGrLPZ40OxRsdDKRGm-JvfNnVmm1mX6K5jsEmr6dmBut1AdvoJS4l1mTjg90aH64aPfppn4quoWdDW8G0m-JXXS-3cYIf374vu5TiFEcIt3FfhcUHaEwMm-1V7ZofowdOTxmeHM9T9PnNxafzd-3lh7fvz19ftqbvWWkHTJywjI_CSV7_b8HxTgyD00ZzZqTFTjg-gATsOmHIyK3TWtYAGS0TujtFLw59lxS_bCEXNftsYJp0gLjNSkhJekok-z-SkOHfJB86KRnlspLkQJoUc07g1JL8XJelCFZ7tWqjqlq1V6swV1VtzTw7dt-O1cHvxC-XFXh-BHQ2enKpqvT5D9fRXlCKK_fqwEHd742HpLLxULVbn8AUZaP_yxg_AdBcxlk</recordid><startdate>20100915</startdate><enddate>20100915</enddate><creator>Kamal, Ahmed</creator><creator>Dastagiri, D.</creator><creator>Ramaiah, M. Janaki</creator><creator>Bharathi, E. Vijaya</creator><creator>Reddy, J. Surendranadha</creator><creator>Balakishan, G.</creator><creator>Sarma, Pranjal</creator><creator>Pushpavalli, S.N.C.V.L.</creator><creator>Pal-Bhadra, Manika</creator><creator>Juvekar, Aarti</creator><creator>Sen, Subrata</creator><creator>Zingde, Surekha</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20100915</creationdate><title>Synthesis, anticancer activity and mitochondrial mediated apoptosis inducing ability of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates</title><author>Kamal, Ahmed ; Dastagiri, D. ; Ramaiah, M. Janaki ; Bharathi, E. Vijaya ; Reddy, J. Surendranadha ; Balakishan, G. ; Sarma, Pranjal ; Pushpavalli, S.N.C.V.L. ; Pal-Bhadra, Manika ; Juvekar, Aarti ; Sen, Subrata ; Zingde, Surekha</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c446t-501f8d67b8f97010def73855faca76c9d0f8f75e9e0f38c1b7dfaa967b1bd68a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>2,5-Diaryloxadiazoles</topic><topic>Animals</topic><topic>Anticancer activity</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - therapeutic use</topic><topic>Apoptosis</topic><topic>bcl-2-Associated X Protein - metabolism</topic><topic>Benzodiazepines - chemical synthesis</topic><topic>Benzodiazepines - chemistry</topic><topic>Benzodiazepines - therapeutic use</topic><topic>Biological and medical sciences</topic><topic>Caspases</topic><topic>Caspases - metabolism</topic><topic>Cell Cycle - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cyclin dependent kinase-2 (CDK-2)</topic><topic>Cyclin-Dependent Kinase 2 - metabolism</topic><topic>General aspects</topic><topic>Humans</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred NOD</topic><topic>Miscellaneous</topic><topic>Mitochondria - drug effects</topic><topic>Neoplasms - drug therapy</topic><topic>Oxadiazoles - chemical synthesis</topic><topic>Oxadiazoles - chemistry</topic><topic>p53</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrrolobenzodiazepine</topic><topic>Tumor Suppressor Protein p53 - metabolism</topic><topic>Xenograft Model Antitumor Assays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamal, Ahmed</creatorcontrib><creatorcontrib>Dastagiri, D.</creatorcontrib><creatorcontrib>Ramaiah, M. Janaki</creatorcontrib><creatorcontrib>Bharathi, E. Vijaya</creatorcontrib><creatorcontrib>Reddy, J. 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Janaki</au><au>Bharathi, E. Vijaya</au><au>Reddy, J. Surendranadha</au><au>Balakishan, G.</au><au>Sarma, Pranjal</au><au>Pushpavalli, S.N.C.V.L.</au><au>Pal-Bhadra, Manika</au><au>Juvekar, Aarti</au><au>Sen, Subrata</au><au>Zingde, Surekha</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, anticancer activity and mitochondrial mediated apoptosis inducing ability of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2010-09-15</date><risdate>2010</risdate><volume>18</volume><issue>18</issue><spage>6666</spage><epage>6677</epage><pages>6666-6677</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>New class of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates have been prepared and evaluated for their anticancer activity. Further, some of the biological assays related to mechanism aspects have also been carried out.
A series of 2,5-diaryloxadiazole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates have been prepared and evaluated for their anticancer activity. These conjugates have shown promising activity with GI50 values ranging from <0.1 to 0.29μΜ. It is observed that some of these conjugates particularly 4a, 4d, 4i and 4l exhibit significant anticancer activity. Some detailed biological assays relating to the cell cycle aspects associated to Bax and caspases have been examined with a view to understand the mechanism of action of these conjugates.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20732817</pmid><doi>10.1016/j.bmc.2010.07.067</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2010-09, Vol.18 (18), p.6666-6677 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 2,5-Diaryloxadiazoles Animals Anticancer activity Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - therapeutic use Apoptosis bcl-2-Associated X Protein - metabolism Benzodiazepines - chemical synthesis Benzodiazepines - chemistry Benzodiazepines - therapeutic use Biological and medical sciences Caspases Caspases - metabolism Cell Cycle - drug effects Cell Line, Tumor Cyclin dependent kinase-2 (CDK-2) Cyclin-Dependent Kinase 2 - metabolism General aspects Humans Male Medical sciences Mice Mice, Inbred NOD Miscellaneous Mitochondria - drug effects Neoplasms - drug therapy Oxadiazoles - chemical synthesis Oxadiazoles - chemistry p53 Pharmacology. Drug treatments Pyrrolobenzodiazepine Tumor Suppressor Protein p53 - metabolism Xenograft Model Antitumor Assays |
| title | Synthesis, anticancer activity and mitochondrial mediated apoptosis inducing ability of 2,5-diaryloxadiazole–pyrrolobenzodiazepine conjugates |
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