Loading…
New Arteannuin B Derivatives and Their Cytotoxic Activity
Previously unknown conjugates of the natural sesquiterpene lactone arteannuin B, which was isolated from Artemisia annua , were synthesized via Michael reactions with pharmacophoric amines and tested in vitro for cytotoxic activity. The compounds were shown to exhibit antiproliferative properties fo...
Saved in:
| Published in: | Chemistry of natural compounds 2020-05, Vol.56 (3), p.445-451 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83 |
| container_end_page | 451 |
| container_issue | 3 |
| container_start_page | 445 |
| container_title | Chemistry of natural compounds |
| container_volume | 56 |
| creator | Klochkov, S. G. Neganova, M. E. Pukhov, S. A. Afanas’eva, S. V. Aleksandrova, Yu. R. Yandulova, E. Yu |
| description | Previously unknown conjugates of the natural sesquiterpene lactone arteannuin B, which was isolated from
Artemisia annua
, were synthesized via Michael reactions with pharmacophoric amines and tested in vitro for cytotoxic activity. The compounds were shown to exhibit antiproliferative properties for various tumor cell lines. The most active derivatives had IC
50
values of 8–36 μM, which exceeded that of starting arteannuin B. Practically all obtained conjugates were found to modulate glycolysis in MCF7 tumor cells. The lead compound was the conjugate with 3-ethoxycarbonylpiperidine, which could be considered a platform for developing antitumor drugs. |
| doi_str_mv | 10.1007/s10600-020-03059-2 |
| format | article |
| fullrecord | <record><control><sourceid>gale_proqu</sourceid><recordid>TN_cdi_proquest_journals_2412166913</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A626344690</galeid><sourcerecordid>A626344690</sourcerecordid><originalsourceid>FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83</originalsourceid><addsrcrecordid>eNp9kVtLwzAYhoMoOKd_wKuCV150fknaNL2s8zQYCjqvQ9omM2NrNUnn9u-NVhgDkZB8JHmeHHgROscwwgDZlcPAAGIgoVNI85gcoAFOMxpzyvkhGgBAHlNM4RidOLcIU84YH6D8UX1GhfVKNk1nmug6ulHWrKU3a-Ui2dTR7E0ZG423vvXtxlRRUYU947en6EjLpVNnv3WIXu9uZ-OHePp0PxkX07hKCPiYJpTLtOIk51mWaColgRJShnVeKggjlYmuw0tlWUudqQwySRkrc5XhWktOh-iiP_fdth-dcl4s2s424UpBEkwwYzmmO2oul0qYRrfeymplXCUKRhhNEpZDoEZ_UKHVamWqtlHahPU94XJPCIxXGz-XnXNi8vK8z5KerWzrnFVavFuzknYrMIjvlESfkggpiZ-UBAkS7SUX4Gau7O53_1hft0SQ8w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2412166913</pqid></control><display><type>article</type><title>New Arteannuin B Derivatives and Their Cytotoxic Activity</title><source>Springer Nature</source><creator>Klochkov, S. G. ; Neganova, M. E. ; Pukhov, S. A. ; Afanas’eva, S. V. ; Aleksandrova, Yu. R. ; Yandulova, E. Yu</creator><creatorcontrib>Klochkov, S. G. ; Neganova, M. E. ; Pukhov, S. A. ; Afanas’eva, S. V. ; Aleksandrova, Yu. R. ; Yandulova, E. Yu</creatorcontrib><description>Previously unknown conjugates of the natural sesquiterpene lactone arteannuin B, which was isolated from
Artemisia annua
, were synthesized via Michael reactions with pharmacophoric amines and tested in vitro for cytotoxic activity. The compounds were shown to exhibit antiproliferative properties for various tumor cell lines. The most active derivatives had IC
50
values of 8–36 μM, which exceeded that of starting arteannuin B. Practically all obtained conjugates were found to modulate glycolysis in MCF7 tumor cells. The lead compound was the conjugate with 3-ethoxycarbonylpiperidine, which could be considered a platform for developing antitumor drugs.</description><identifier>ISSN: 0009-3130</identifier><identifier>EISSN: 1573-8388</identifier><identifier>DOI: 10.1007/s10600-020-03059-2</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Amines ; Chemical synthesis ; Conjugates ; Cytotoxicity ; Derivatives ; Glucose metabolism ; Glycolysis ; Lead compounds ; Medicine ; Organic Chemistry ; Pharmacy ; Physiological aspects ; Plant Sciences</subject><ispartof>Chemistry of natural compounds, 2020-05, Vol.56 (3), p.445-451</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2020</rights><rights>COPYRIGHT 2020 Springer</rights><rights>Springer Science+Business Media, LLC, part of Springer Nature 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83</citedby><cites>FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83</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></links><search><creatorcontrib>Klochkov, S. G.</creatorcontrib><creatorcontrib>Neganova, M. E.</creatorcontrib><creatorcontrib>Pukhov, S. A.</creatorcontrib><creatorcontrib>Afanas’eva, S. V.</creatorcontrib><creatorcontrib>Aleksandrova, Yu. R.</creatorcontrib><creatorcontrib>Yandulova, E. Yu</creatorcontrib><title>New Arteannuin B Derivatives and Their Cytotoxic Activity</title><title>Chemistry of natural compounds</title><addtitle>Chem Nat Compd</addtitle><description>Previously unknown conjugates of the natural sesquiterpene lactone arteannuin B, which was isolated from
Artemisia annua
, were synthesized via Michael reactions with pharmacophoric amines and tested in vitro for cytotoxic activity. The compounds were shown to exhibit antiproliferative properties for various tumor cell lines. The most active derivatives had IC
50
values of 8–36 μM, which exceeded that of starting arteannuin B. Practically all obtained conjugates were found to modulate glycolysis in MCF7 tumor cells. The lead compound was the conjugate with 3-ethoxycarbonylpiperidine, which could be considered a platform for developing antitumor drugs.</description><subject>Amines</subject><subject>Chemical synthesis</subject><subject>Conjugates</subject><subject>Cytotoxicity</subject><subject>Derivatives</subject><subject>Glucose metabolism</subject><subject>Glycolysis</subject><subject>Lead compounds</subject><subject>Medicine</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Physiological aspects</subject><subject>Plant Sciences</subject><issn>0009-3130</issn><issn>1573-8388</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kVtLwzAYhoMoOKd_wKuCV150fknaNL2s8zQYCjqvQ9omM2NrNUnn9u-NVhgDkZB8JHmeHHgROscwwgDZlcPAAGIgoVNI85gcoAFOMxpzyvkhGgBAHlNM4RidOLcIU84YH6D8UX1GhfVKNk1nmug6ulHWrKU3a-Ui2dTR7E0ZG423vvXtxlRRUYU947en6EjLpVNnv3WIXu9uZ-OHePp0PxkX07hKCPiYJpTLtOIk51mWaColgRJShnVeKggjlYmuw0tlWUudqQwySRkrc5XhWktOh-iiP_fdth-dcl4s2s424UpBEkwwYzmmO2oul0qYRrfeymplXCUKRhhNEpZDoEZ_UKHVamWqtlHahPU94XJPCIxXGz-XnXNi8vK8z5KerWzrnFVavFuzknYrMIjvlESfkggpiZ-UBAkS7SUX4Gau7O53_1hft0SQ8w</recordid><startdate>20200501</startdate><enddate>20200501</enddate><creator>Klochkov, S. G.</creator><creator>Neganova, M. E.</creator><creator>Pukhov, S. A.</creator><creator>Afanas’eva, S. V.</creator><creator>Aleksandrova, Yu. R.</creator><creator>Yandulova, E. Yu</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope></search><sort><creationdate>20200501</creationdate><title>New Arteannuin B Derivatives and Their Cytotoxic Activity</title><author>Klochkov, S. G. ; Neganova, M. E. ; Pukhov, S. A. ; Afanas’eva, S. V. ; Aleksandrova, Yu. R. ; Yandulova, E. Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amines</topic><topic>Chemical synthesis</topic><topic>Conjugates</topic><topic>Cytotoxicity</topic><topic>Derivatives</topic><topic>Glucose metabolism</topic><topic>Glycolysis</topic><topic>Lead compounds</topic><topic>Medicine</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Physiological aspects</topic><topic>Plant Sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Klochkov, S. G.</creatorcontrib><creatorcontrib>Neganova, M. E.</creatorcontrib><creatorcontrib>Pukhov, S. A.</creatorcontrib><creatorcontrib>Afanas’eva, S. V.</creatorcontrib><creatorcontrib>Aleksandrova, Yu. R.</creatorcontrib><creatorcontrib>Yandulova, E. Yu</creatorcontrib><collection>CrossRef</collection><collection>Gale In Context: Science</collection><jtitle>Chemistry of natural compounds</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Klochkov, S. G.</au><au>Neganova, M. E.</au><au>Pukhov, S. A.</au><au>Afanas’eva, S. V.</au><au>Aleksandrova, Yu. R.</au><au>Yandulova, E. Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Arteannuin B Derivatives and Their Cytotoxic Activity</atitle><jtitle>Chemistry of natural compounds</jtitle><stitle>Chem Nat Compd</stitle><date>2020-05-01</date><risdate>2020</risdate><volume>56</volume><issue>3</issue><spage>445</spage><epage>451</epage><pages>445-451</pages><issn>0009-3130</issn><eissn>1573-8388</eissn><abstract>Previously unknown conjugates of the natural sesquiterpene lactone arteannuin B, which was isolated from
Artemisia annua
, were synthesized via Michael reactions with pharmacophoric amines and tested in vitro for cytotoxic activity. The compounds were shown to exhibit antiproliferative properties for various tumor cell lines. The most active derivatives had IC
50
values of 8–36 μM, which exceeded that of starting arteannuin B. Practically all obtained conjugates were found to modulate glycolysis in MCF7 tumor cells. The lead compound was the conjugate with 3-ethoxycarbonylpiperidine, which could be considered a platform for developing antitumor drugs.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10600-020-03059-2</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-3130 |
| ispartof | Chemistry of natural compounds, 2020-05, Vol.56 (3), p.445-451 |
| issn | 0009-3130 1573-8388 |
| language | eng |
| recordid | cdi_proquest_journals_2412166913 |
| source | Springer Nature |
| subjects | Amines Chemical synthesis Conjugates Cytotoxicity Derivatives Glucose metabolism Glycolysis Lead compounds Medicine Organic Chemistry Pharmacy Physiological aspects Plant Sciences |
| title | New Arteannuin B Derivatives and Their Cytotoxic Activity |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T20%3A26%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_proqu&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=New%20Arteannuin%20B%20Derivatives%20and%20Their%20Cytotoxic%20Activity&rft.jtitle=Chemistry%20of%20natural%20compounds&rft.au=Klochkov,%20S.%20G.&rft.date=2020-05-01&rft.volume=56&rft.issue=3&rft.spage=445&rft.epage=451&rft.pages=445-451&rft.issn=0009-3130&rft.eissn=1573-8388&rft_id=info:doi/10.1007/s10600-020-03059-2&rft_dat=%3Cgale_proqu%3EA626344690%3C/gale_proqu%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c420t-3438a5c8298774f3aa20b0561f9be01f93a4fd573abdaf7e707a366b9e71dfa83%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2412166913&rft_id=info:pmid/&rft_galeid=A626344690&rfr_iscdi=true |