Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues
A kind of novel bisindolylalkanes analogue is synthesized. Most of them showed antitumor activities in vitro and varying degree topoisomerase II inhibitory activity. In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes an...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2013-12, Vol.21 (24), p.7624-7627 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Song, Ya-Li Dong, Yun-Fang Yang, Tao Zhang, Chao-Chao Su, Li-Min Huang, Xin Zhang, Dong-Nuan Yang, Geng-Liang Liu, Yu-Xin |
| description | A kind of novel bisindolylalkanes analogue is synthesized. Most of them showed antitumor activities in vitro and varying degree topoisomerase II inhibitory activity.
In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes analogues such as 3,3′-(thiochroman-4,4-diyl)bis(1H-indole) are synthesized. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Anti-proliferative activities for all of these compounds are investigated by the method of MTT assay on 7 human cancer lines. Most of them showed antitumor activities in vitro, the half maximal inhibitory concentration (IC50) value is 7.798μg/mL of 3a against MCF7. Compound 3a showed comparable topoisomerase II inhibitory activity to etoposide (VP-16) at 100μM concentration. The rest of the compounds also showed varying degree topoisomerase II inhibitory activity. |
| doi_str_mv | 10.1016/j.bmc.2013.10.034 |
| format | Article |
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In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes analogues such as 3,3′-(thiochroman-4,4-diyl)bis(1H-indole) are synthesized. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Anti-proliferative activities for all of these compounds are investigated by the method of MTT assay on 7 human cancer lines. Most of them showed antitumor activities in vitro, the half maximal inhibitory concentration (IC50) value is 7.798μg/mL of 3a against MCF7. Compound 3a showed comparable topoisomerase II inhibitory activity to etoposide (VP-16) at 100μM concentration. The rest of the compounds also showed varying degree topoisomerase II inhibitory activity.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2013.10.034</identifier><identifier>PMID: 24262885</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anticancer ; anticarcinogenic activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Bisindolylalkane ; Cell Line, Tumor ; Cell Proliferation - drug effects ; chemistry ; chemoprevention ; DNA topoisomerase (ATP-hydrolysing) ; DNA Topoisomerases, Type II - metabolism ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Hep G2 Cells ; Humans ; Indole ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Inhibitory Concentration 50 ; MCF-7 Cells ; Molecular Structure ; nuclear magnetic resonance spectroscopy ; Structure-Activity Relationship ; Thiochroman-4-one ; Topoisomerase II ; Topoisomerase II Inhibitors - chemical synthesis ; Topoisomerase II Inhibitors - chemistry ; Topoisomerase II Inhibitors - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2013-12, Vol.21 (24), p.7624-7627</ispartof><rights>2013 Elsevier Ltd</rights><rights>Copyright © 2013 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c410t-1dac77c9b911cc099247ddf3a9acb423cc7a771b0473e970e0458116e5844433</citedby><cites>FETCH-LOGICAL-c410t-1dac77c9b911cc099247ddf3a9acb423cc7a771b0473e970e0458116e5844433</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.2013.10.034$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24262885$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Song, Ya-Li</creatorcontrib><creatorcontrib>Dong, Yun-Fang</creatorcontrib><creatorcontrib>Yang, Tao</creatorcontrib><creatorcontrib>Zhang, Chao-Chao</creatorcontrib><creatorcontrib>Su, Li-Min</creatorcontrib><creatorcontrib>Huang, Xin</creatorcontrib><creatorcontrib>Zhang, Dong-Nuan</creatorcontrib><creatorcontrib>Yang, Geng-Liang</creatorcontrib><creatorcontrib>Liu, Yu-Xin</creatorcontrib><title>Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A kind of novel bisindolylalkanes analogue is synthesized. Most of them showed antitumor activities in vitro and varying degree topoisomerase II inhibitory activity.
In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes analogues such as 3,3′-(thiochroman-4,4-diyl)bis(1H-indole) are synthesized. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Anti-proliferative activities for all of these compounds are investigated by the method of MTT assay on 7 human cancer lines. Most of them showed antitumor activities in vitro, the half maximal inhibitory concentration (IC50) value is 7.798μg/mL of 3a against MCF7. Compound 3a showed comparable topoisomerase II inhibitory activity to etoposide (VP-16) at 100μM concentration. The rest of the compounds also showed varying degree topoisomerase II inhibitory activity.</description><subject>Anticancer</subject><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bisindolylalkane</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>chemistry</subject><subject>chemoprevention</subject><subject>DNA topoisomerase (ATP-hydrolysing)</subject><subject>DNA Topoisomerases, Type II - metabolism</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Indole</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Inhibitory Concentration 50</subject><subject>MCF-7 Cells</subject><subject>Molecular Structure</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Structure-Activity Relationship</subject><subject>Thiochroman-4-one</subject><subject>Topoisomerase II</subject><subject>Topoisomerase II Inhibitors - chemical synthesis</subject><subject>Topoisomerase II Inhibitors - chemistry</subject><subject>Topoisomerase II Inhibitors - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EokvhB3CBHLlkO2M7cSxOqCofUqse2p6tieO0Xpx4sbMr7b_Hqy0c4WSN9bzvjB7G3iOsEbC92Kz7ya45oCjzGoR8wVYoW1kLofElW4Fuuxo63Z6xNzlvAIBLja_ZGZe85V3XrNjN3WFenlz2uaJ5qLZPlCayMcRHbylUbk9hR4uPcxXHao57F6reZz8PMRwChZ80u2OSSmDn8lv2aqSQ3bvn95zdf726v_xeX99--3H55bq2EmGpcSCrlNW9RrQWtOZSDcMoSJPtJRfWKlIKe5BKOK3AgWw6xNY1nZRSiHP26VS7TfFXWbuYyWfrQijXxF022GCrpOp4-3-06NIIClVB8YTaFHNObjTb5CdKB4Ngjr7NxhTf5uj7-FV8l8yH5_pdP7nhb-KP4AJ8PAEjRUOPyWfzcFcaGgBEbDgU4vOJcEXY3rtksvVutm7wydnFDNH_44DfLUeZOw</recordid><startdate>20131215</startdate><enddate>20131215</enddate><creator>Song, Ya-Li</creator><creator>Dong, Yun-Fang</creator><creator>Yang, Tao</creator><creator>Zhang, Chao-Chao</creator><creator>Su, Li-Min</creator><creator>Huang, Xin</creator><creator>Zhang, Dong-Nuan</creator><creator>Yang, Geng-Liang</creator><creator>Liu, Yu-Xin</creator><general>Elsevier Ltd</general><scope>FBQ</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>20131215</creationdate><title>Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues</title><author>Song, Ya-Li ; Dong, Yun-Fang ; Yang, Tao ; Zhang, Chao-Chao ; Su, Li-Min ; Huang, Xin ; Zhang, Dong-Nuan ; Yang, Geng-Liang ; Liu, Yu-Xin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c410t-1dac77c9b911cc099247ddf3a9acb423cc7a771b0473e970e0458116e5844433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Anticancer</topic><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Bisindolylalkane</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>chemistry</topic><topic>chemoprevention</topic><topic>DNA topoisomerase (ATP-hydrolysing)</topic><topic>DNA Topoisomerases, Type II - metabolism</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Indole</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Inhibitory Concentration 50</topic><topic>MCF-7 Cells</topic><topic>Molecular Structure</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Structure-Activity Relationship</topic><topic>Thiochroman-4-one</topic><topic>Topoisomerase II</topic><topic>Topoisomerase II Inhibitors - chemical synthesis</topic><topic>Topoisomerase II Inhibitors - chemistry</topic><topic>Topoisomerase II Inhibitors - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Ya-Li</creatorcontrib><creatorcontrib>Dong, Yun-Fang</creatorcontrib><creatorcontrib>Yang, Tao</creatorcontrib><creatorcontrib>Zhang, Chao-Chao</creatorcontrib><creatorcontrib>Su, Li-Min</creatorcontrib><creatorcontrib>Huang, Xin</creatorcontrib><creatorcontrib>Zhang, Dong-Nuan</creatorcontrib><creatorcontrib>Yang, Geng-Liang</creatorcontrib><creatorcontrib>Liu, Yu-Xin</creatorcontrib><collection>AGRIS</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</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Song, Ya-Li</au><au>Dong, Yun-Fang</au><au>Yang, Tao</au><au>Zhang, Chao-Chao</au><au>Su, Li-Min</au><au>Huang, Xin</au><au>Zhang, Dong-Nuan</au><au>Yang, Geng-Liang</au><au>Liu, Yu-Xin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2013-12-15</date><risdate>2013</risdate><volume>21</volume><issue>24</issue><spage>7624</spage><epage>7627</epage><pages>7624-7627</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A kind of novel bisindolylalkanes analogue is synthesized. Most of them showed antitumor activities in vitro and varying degree topoisomerase II inhibitory activity.
In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes analogues such as 3,3′-(thiochroman-4,4-diyl)bis(1H-indole) are synthesized. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Anti-proliferative activities for all of these compounds are investigated by the method of MTT assay on 7 human cancer lines. Most of them showed antitumor activities in vitro, the half maximal inhibitory concentration (IC50) value is 7.798μg/mL of 3a against MCF7. Compound 3a showed comparable topoisomerase II inhibitory activity to etoposide (VP-16) at 100μM concentration. The rest of the compounds also showed varying degree topoisomerase II inhibitory activity.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24262885</pmid><doi>10.1016/j.bmc.2013.10.034</doi><tpages>4</tpages></addata></record> |
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| subjects | Anticancer anticarcinogenic activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Bisindolylalkane Cell Line, Tumor Cell Proliferation - drug effects chemistry chemoprevention DNA topoisomerase (ATP-hydrolysing) DNA Topoisomerases, Type II - metabolism Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Hep G2 Cells Humans Indole Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Inhibitory Concentration 50 MCF-7 Cells Molecular Structure nuclear magnetic resonance spectroscopy Structure-Activity Relationship Thiochroman-4-one Topoisomerase II Topoisomerase II Inhibitors - chemical synthesis Topoisomerase II Inhibitors - chemistry Topoisomerase II Inhibitors - pharmacology |
| title | Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues |
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