Synthesis of new indirubin derivatives and their in vitro anticancer activity
The opening of epoxy rings from ( 2′Z )- N -1-(oxiran-2-ylmethyl)indirubin ( 2 ) and ( 2′Z - 3′E )-indirubin-3ʹ-[ O -oxiran-2-ylmethyl)oxime] ( 6 ) with thiols gave 17 new derivatives of indirubin in good yields. Their structures were elucidated by 1D-, 2D-NMR and HRMS spectra. Screening for antican...
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| Veröffentlicht in: | Chemical papers 2019-05, Vol.73 (5), p.1083-1092 |
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| container_title | Chemical papers |
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| creator | Nguyen, Dan Trong Truong, Giang Nguyen Van Vuong, Truong Van, Tai Nguyen Manh, Cuong Nguyen Dao, Cuong To Thuy, Thuy Dinh Thi Van, Chinh Luu Khac, Vu Tran |
| description | The opening of epoxy rings from (
2′Z
)-
N
-1-(oxiran-2-ylmethyl)indirubin (
2
) and (
2′Z
-
3′E
)-indirubin-3ʹ-[
O
-oxiran-2-ylmethyl)oxime] (
6
) with thiols gave 17 new derivatives of indirubin in good yields. Their structures were elucidated by 1D-, 2D-NMR and HRMS spectra. Screening for anticancer activity was performed with four human cancer cell lines: SW480, LU-1, HepG2 and HL-60 in comparison with indirubin, indirubin-3′-oxime and 6-mercaptopurine. The results showed that cytotoxic and anti-proliferative activities of five derivatives were found in the range of 1.35–19.24 µM. Among synthesized derivatives,
4f
showed the strongest activity against all four tested cancer cell lines with IC
50
values of 1.65, 2.21, 1.90 and 1.35 µM, respectively. |
| doi_str_mv | 10.1007/s11696-018-0659-4 |
| format | Article |
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2′Z
)-
N
-1-(oxiran-2-ylmethyl)indirubin (
2
) and (
2′Z
-
3′E
)-indirubin-3ʹ-[
O
-oxiran-2-ylmethyl)oxime] (
6
) with thiols gave 17 new derivatives of indirubin in good yields. Their structures were elucidated by 1D-, 2D-NMR and HRMS spectra. Screening for anticancer activity was performed with four human cancer cell lines: SW480, LU-1, HepG2 and HL-60 in comparison with indirubin, indirubin-3′-oxime and 6-mercaptopurine. The results showed that cytotoxic and anti-proliferative activities of five derivatives were found in the range of 1.35–19.24 µM. Among synthesized derivatives,
4f
showed the strongest activity against all four tested cancer cell lines with IC
50
values of 1.65, 2.21, 1.90 and 1.35 µM, respectively.</description><identifier>ISSN: 2585-7290</identifier><identifier>ISSN: 0366-6352</identifier><identifier>EISSN: 1336-9075</identifier><identifier>DOI: 10.1007/s11696-018-0659-4</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Anticancer properties ; Biochemistry ; Biotechnology ; Cancer ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Derivatives ; Human performance ; Industrial Chemistry/Chemical Engineering ; Materials Science ; Medicinal Chemistry ; NMR ; Nuclear magnetic resonance ; Original Paper ; Thiols</subject><ispartof>Chemical papers, 2019-05, Vol.73 (5), p.1083-1092</ispartof><rights>Institute of Chemistry, Slovak Academy of Sciences 2018</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-d23b3f77d701e9dff9d8e4437a627a55ce4c5b195add09e7cd541934db9996ed3</citedby><cites>FETCH-LOGICAL-c353t-d23b3f77d701e9dff9d8e4437a627a55ce4c5b195add09e7cd541934db9996ed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11696-018-0659-4$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11696-018-0659-4$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Nguyen, Dan Trong</creatorcontrib><creatorcontrib>Truong, Giang Nguyen</creatorcontrib><creatorcontrib>Van Vuong, Truong</creatorcontrib><creatorcontrib>Van, Tai Nguyen</creatorcontrib><creatorcontrib>Manh, Cuong Nguyen</creatorcontrib><creatorcontrib>Dao, Cuong To</creatorcontrib><creatorcontrib>Thuy, Thuy Dinh Thi</creatorcontrib><creatorcontrib>Van, Chinh Luu</creatorcontrib><creatorcontrib>Khac, Vu Tran</creatorcontrib><title>Synthesis of new indirubin derivatives and their in vitro anticancer activity</title><title>Chemical papers</title><addtitle>Chem. Pap</addtitle><description>The opening of epoxy rings from (
2′Z
)-
N
-1-(oxiran-2-ylmethyl)indirubin (
2
) and (
2′Z
-
3′E
)-indirubin-3ʹ-[
O
-oxiran-2-ylmethyl)oxime] (
6
) with thiols gave 17 new derivatives of indirubin in good yields. Their structures were elucidated by 1D-, 2D-NMR and HRMS spectra. Screening for anticancer activity was performed with four human cancer cell lines: SW480, LU-1, HepG2 and HL-60 in comparison with indirubin, indirubin-3′-oxime and 6-mercaptopurine. The results showed that cytotoxic and anti-proliferative activities of five derivatives were found in the range of 1.35–19.24 µM. Among synthesized derivatives,
4f
showed the strongest activity against all four tested cancer cell lines with IC
50
values of 1.65, 2.21, 1.90 and 1.35 µM, respectively.</description><subject>Anticancer properties</subject><subject>Biochemistry</subject><subject>Biotechnology</subject><subject>Cancer</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Derivatives</subject><subject>Human performance</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Original Paper</subject><subject>Thiols</subject><issn>2585-7290</issn><issn>0366-6352</issn><issn>1336-9075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LAzEURYMoWGp_gLuA62i-M1lK8aNQcaGuQybJaEQzNUkr_femjODK1YP3zr0PDgDnBF8SjNVVIURqiTDpEJZCI34EZoQxiTRW4hjMqOgEUlTjU7AoJfaYc8VoJ9UMPDztU30LJRY4DjCFbxiTj3nbxwR9yHFna9yFAm3ysHExtzvcxZrHtqrR2eRChtY1Ktb9GTgZ7EcJi985By-3N8_Le7R-vFstr9fIMcEq8pT1bFDKK0yC9sOgfRc4Z8pKqqwQLnAneqKF9R7roJwXnGjGfa-1lsGzObiYejd5_NqGUs37uM2pvTSUYsEl0bxrFJkol8dSchjMJsdPm_eGYHMQZyZxpokzB3GGtwydMqWx6TXkv-b_Qz-pQXFO</recordid><startdate>20190501</startdate><enddate>20190501</enddate><creator>Nguyen, Dan Trong</creator><creator>Truong, Giang Nguyen</creator><creator>Van Vuong, Truong</creator><creator>Van, Tai Nguyen</creator><creator>Manh, Cuong Nguyen</creator><creator>Dao, Cuong To</creator><creator>Thuy, Thuy Dinh Thi</creator><creator>Van, Chinh Luu</creator><creator>Khac, Vu Tran</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20190501</creationdate><title>Synthesis of new indirubin derivatives and their in vitro anticancer activity</title><author>Nguyen, Dan Trong ; Truong, Giang Nguyen ; Van Vuong, Truong ; Van, Tai Nguyen ; Manh, Cuong Nguyen ; Dao, Cuong To ; Thuy, Thuy Dinh Thi ; Van, Chinh Luu ; Khac, Vu Tran</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-d23b3f77d701e9dff9d8e4437a627a55ce4c5b195add09e7cd541934db9996ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Anticancer properties</topic><topic>Biochemistry</topic><topic>Biotechnology</topic><topic>Cancer</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Derivatives</topic><topic>Human performance</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Original Paper</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen, Dan Trong</creatorcontrib><creatorcontrib>Truong, Giang Nguyen</creatorcontrib><creatorcontrib>Van Vuong, Truong</creatorcontrib><creatorcontrib>Van, Tai Nguyen</creatorcontrib><creatorcontrib>Manh, Cuong Nguyen</creatorcontrib><creatorcontrib>Dao, Cuong To</creatorcontrib><creatorcontrib>Thuy, Thuy Dinh Thi</creatorcontrib><creatorcontrib>Van, Chinh Luu</creatorcontrib><creatorcontrib>Khac, Vu Tran</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen, Dan Trong</au><au>Truong, Giang Nguyen</au><au>Van Vuong, Truong</au><au>Van, Tai Nguyen</au><au>Manh, Cuong Nguyen</au><au>Dao, Cuong To</au><au>Thuy, Thuy Dinh Thi</au><au>Van, Chinh Luu</au><au>Khac, Vu Tran</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of new indirubin derivatives and their in vitro anticancer activity</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2019-05-01</date><risdate>2019</risdate><volume>73</volume><issue>5</issue><spage>1083</spage><epage>1092</epage><pages>1083-1092</pages><issn>2585-7290</issn><issn>0366-6352</issn><eissn>1336-9075</eissn><abstract>The opening of epoxy rings from (
2′Z
)-
N
-1-(oxiran-2-ylmethyl)indirubin (
2
) and (
2′Z
-
3′E
)-indirubin-3ʹ-[
O
-oxiran-2-ylmethyl)oxime] (
6
) with thiols gave 17 new derivatives of indirubin in good yields. Their structures were elucidated by 1D-, 2D-NMR and HRMS spectra. Screening for anticancer activity was performed with four human cancer cell lines: SW480, LU-1, HepG2 and HL-60 in comparison with indirubin, indirubin-3′-oxime and 6-mercaptopurine. The results showed that cytotoxic and anti-proliferative activities of five derivatives were found in the range of 1.35–19.24 µM. Among synthesized derivatives,
4f
showed the strongest activity against all four tested cancer cell lines with IC
50
values of 1.65, 2.21, 1.90 and 1.35 µM, respectively.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1007/s11696-018-0659-4</doi><tpages>10</tpages></addata></record> |
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| issn | 2585-7290 0366-6352 1336-9075 |
| language | eng |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Anticancer properties Biochemistry Biotechnology Cancer Chemistry Chemistry and Materials Science Chemistry/Food Science Derivatives Human performance Industrial Chemistry/Chemical Engineering Materials Science Medicinal Chemistry NMR Nuclear magnetic resonance Original Paper Thiols |
| title | Synthesis of new indirubin derivatives and their in vitro anticancer activity |
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