Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin
Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4′-O-Demethyl-4β-[(...
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| Veröffentlicht in: | European journal of medicinal chemistry 2013-06, Vol.64, p.621-628 |
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| container_title | European journal of medicinal chemistry |
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| creator | Liu, Jian-Fei Sang, Chun-Yan Xu, Xiao-Hui Zhang, Lin-Lin Yang, Xuan Hui, Lin Zhang, Jin-Bang Chen, Shi-Wu |
| description | Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4′-O-Demethyl-4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-deoxypodophyllotoxin cyclopentyl carbamate, the most potent compound, induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells. Furthermore, this compound inhibited the formation of microtubules in A-549 cells and caused the inhibition of DNA topoisomerase-II.
Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin exhibited promising in vitro cytotoxicities. Compound 22 induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells, and inhibited the formation of microtubules and DNA topoisomerase-II. [Display omitted]
•Eleven carbamates of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by click chemistry.•Some carbamates exhibited potent cytotoxic activity compared with VP-16.•Compound 22 arrests cell cycle in the G2/M phase accompanied by apoptosis in A-549 cells.•Compound 22 inhibits the formation of microtubules in A-549 cells.•Compound 22 inhibits DNA topoisomerase-II. |
| doi_str_mv | 10.1016/j.ejmech.2013.03.068 |
| format | Article |
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Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin exhibited promising in vitro cytotoxicities. Compound 22 induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells, and inhibited the formation of microtubules and DNA topoisomerase-II. [Display omitted]
•Eleven carbamates of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by click chemistry.•Some carbamates exhibited potent cytotoxic activity compared with VP-16.•Compound 22 arrests cell cycle in the G2/M phase accompanied by apoptosis in A-549 cells.•Compound 22 inhibits the formation of microtubules in A-549 cells.•Compound 22 inhibits DNA topoisomerase-II.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2013.03.068</identifier><identifier>PMID: 23711769</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Carbamates - chemical synthesis ; Carbamates - chemistry ; Carbamates - pharmacology ; Cell Cycle - drug effects ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; HeLa Cells ; HL-60 Cells ; Humans ; Microtubules ; Molecular Structure ; Podophyllotoxin ; Podophyllotoxin - analogs & derivatives ; Podophyllotoxin - chemistry ; Podophyllotoxin - pharmacology ; Structure-Activity Relationship ; Topoisomerase-II ; Triazole</subject><ispartof>European journal of medicinal chemistry, 2013-06, Vol.64, p.621-628</ispartof><rights>2013 Elsevier Masson SAS</rights><rights>Copyright © 2013 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-ac1206daf68184441922456ed39b3e164d46f17a952b40fa67808671f5e4a3563</citedby><cites>FETCH-LOGICAL-c362t-ac1206daf68184441922456ed39b3e164d46f17a952b40fa67808671f5e4a3563</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2013.03.068$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23711769$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Jian-Fei</creatorcontrib><creatorcontrib>Sang, Chun-Yan</creatorcontrib><creatorcontrib>Xu, Xiao-Hui</creatorcontrib><creatorcontrib>Zhang, Lin-Lin</creatorcontrib><creatorcontrib>Yang, Xuan</creatorcontrib><creatorcontrib>Hui, Lin</creatorcontrib><creatorcontrib>Zhang, Jin-Bang</creatorcontrib><creatorcontrib>Chen, Shi-Wu</creatorcontrib><title>Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4′-O-Demethyl-4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-deoxypodophyllotoxin cyclopentyl carbamate, the most potent compound, induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells. Furthermore, this compound inhibited the formation of microtubules in A-549 cells and caused the inhibition of DNA topoisomerase-II.
Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin exhibited promising in vitro cytotoxicities. Compound 22 induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells, and inhibited the formation of microtubules and DNA topoisomerase-II. [Display omitted]
•Eleven carbamates of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by click chemistry.•Some carbamates exhibited potent cytotoxic activity compared with VP-16.•Compound 22 arrests cell cycle in the G2/M phase accompanied by apoptosis in A-549 cells.•Compound 22 inhibits the formation of microtubules in A-549 cells.•Compound 22 inhibits DNA topoisomerase-II.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Carbamates - chemical synthesis</subject><subject>Carbamates - chemistry</subject><subject>Carbamates - pharmacology</subject><subject>Cell Cycle - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HeLa Cells</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Microtubules</subject><subject>Molecular Structure</subject><subject>Podophyllotoxin</subject><subject>Podophyllotoxin - analogs & derivatives</subject><subject>Podophyllotoxin - chemistry</subject><subject>Podophyllotoxin - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Topoisomerase-II</subject><subject>Triazole</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtqGzEUhkVISdy0bxCKlilErm6j0WwCIfQGgS7aroUsncEyMyNXkk0mj9UH6TNVjpMuCweE0Pfr53wIXTK6ZJSpD5slbEZw6yWnTCxpHaVP0IK1ShPBG3mKFpRzQRou5Dl6nfOGUtooSs_QORctq2C3QI_f56msIYeM7eSxm0ss8SE4bF0J-1BmHCe83o12ws5ODhJ2MAwZx77e08qOtgD2kMLeVh6eHuSf3-SKXfNrQUoK9jEOhJF5eL-NPm7X8zA8VUxv0KveDhnePp8X6Oenjz_uvpD7b5-_3t3eEycUL8Q6xqnytleaaSkl6ziXjQIvupUApqSXqmet7Rq-krS3qtVUq5b1DUgrGiUu0NXx322Kv3aQixlDPmxhJ4i7bJioEc07rSsqj6hLMecEvdmmMNo0G0bNwbrZmKN1c7BuaB11iL17btitRvD_Qi-aK3BzBKDuuQ-QTHYBqk4fErhifAz_b_gLRBaVkw</recordid><startdate>20130601</startdate><enddate>20130601</enddate><creator>Liu, Jian-Fei</creator><creator>Sang, Chun-Yan</creator><creator>Xu, Xiao-Hui</creator><creator>Zhang, Lin-Lin</creator><creator>Yang, Xuan</creator><creator>Hui, Lin</creator><creator>Zhang, Jin-Bang</creator><creator>Chen, Shi-Wu</creator><general>Elsevier Masson SAS</general><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></search><sort><creationdate>20130601</creationdate><title>Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin</title><author>Liu, Jian-Fei ; Sang, Chun-Yan ; Xu, Xiao-Hui ; Zhang, Lin-Lin ; Yang, Xuan ; Hui, Lin ; Zhang, Jin-Bang ; Chen, Shi-Wu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-ac1206daf68184441922456ed39b3e164d46f17a952b40fa67808671f5e4a3563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis - drug effects</topic><topic>Carbamates - chemical synthesis</topic><topic>Carbamates - chemistry</topic><topic>Carbamates - pharmacology</topic><topic>Cell Cycle - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HeLa Cells</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Microtubules</topic><topic>Molecular Structure</topic><topic>Podophyllotoxin</topic><topic>Podophyllotoxin - analogs & derivatives</topic><topic>Podophyllotoxin - chemistry</topic><topic>Podophyllotoxin - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Topoisomerase-II</topic><topic>Triazole</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Jian-Fei</creatorcontrib><creatorcontrib>Sang, Chun-Yan</creatorcontrib><creatorcontrib>Xu, Xiao-Hui</creatorcontrib><creatorcontrib>Zhang, Lin-Lin</creatorcontrib><creatorcontrib>Yang, Xuan</creatorcontrib><creatorcontrib>Hui, Lin</creatorcontrib><creatorcontrib>Zhang, Jin-Bang</creatorcontrib><creatorcontrib>Chen, Shi-Wu</creatorcontrib><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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Jian-Fei</au><au>Sang, Chun-Yan</au><au>Xu, Xiao-Hui</au><au>Zhang, Lin-Lin</au><au>Yang, Xuan</au><au>Hui, Lin</au><au>Zhang, Jin-Bang</au><au>Chen, Shi-Wu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2013-06-01</date><risdate>2013</risdate><volume>64</volume><spage>621</spage><epage>628</epage><pages>621-628</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4′-O-Demethyl-4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-deoxypodophyllotoxin cyclopentyl carbamate, the most potent compound, induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells. Furthermore, this compound inhibited the formation of microtubules in A-549 cells and caused the inhibition of DNA topoisomerase-II.
Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin exhibited promising in vitro cytotoxicities. Compound 22 induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells, and inhibited the formation of microtubules and DNA topoisomerase-II. [Display omitted]
•Eleven carbamates of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by click chemistry.•Some carbamates exhibited potent cytotoxic activity compared with VP-16.•Compound 22 arrests cell cycle in the G2/M phase accompanied by apoptosis in A-549 cells.•Compound 22 inhibits the formation of microtubules in A-549 cells.•Compound 22 inhibits DNA topoisomerase-II.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>23711769</pmid><doi>10.1016/j.ejmech.2013.03.068</doi><tpages>8</tpages></addata></record> |
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| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis - drug effects Carbamates - chemical synthesis Carbamates - chemistry Carbamates - pharmacology Cell Cycle - drug effects Cell Line, Tumor Cell Proliferation - drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor HeLa Cells HL-60 Cells Humans Microtubules Molecular Structure Podophyllotoxin Podophyllotoxin - analogs & derivatives Podophyllotoxin - chemistry Podophyllotoxin - pharmacology Structure-Activity Relationship Topoisomerase-II Triazole |
| title | Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin |
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