Syntheses and anticancer activities of novel glucosylated (−)-epigallocatechin-3-gallate derivatives linked via triazole rings
Novel glucosylated (-)-epigallocatechin-3-gallate derivatives 10 – 13 having the EGCG analogs conjugated to the d -glucosyl azide were synthesized by carrying out the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, and were evaluated for their cytotoxicities against a panel of five hum...
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| Veröffentlicht in: | Medicinal chemistry research 2021-06, Vol.30 (6), p.1240-1248 |
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| container_title | Medicinal chemistry research |
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| creator | Shi, Bo-Ya Wang, Ze-Hao Zhang, Ning Xie, Yin-Rong Sun, Xiu-Li Yang, Hao-Nan Wu, Yi-Long Zi, Cheng-Ting Wang, Xuan-Jun Sheng, Jun |
| description | Novel glucosylated (-)-epigallocatechin-3-gallate derivatives
10
–
13
having the EGCG analogs conjugated to the
d
-glucosyl azide were synthesized by carrying out the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, and were evaluated for their cytotoxicities against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) using MTT assays. Compounds
10
and
11
showed the highest levels of cytotoxicity against the HL-60 cells with IC
50
values of 4.57 and 3.78 μM, respectively, and showed moderate selectivity toward cancer cell lines. Compound
11
was also shown to induce apoptosis in HL-60 cells. Most notably, inclusion of the perbutyrylated glucose residue in an EGCG derivative was concluded to lead to increased anticancer activity. |
| doi_str_mv | 10.1007/s00044-021-02726-5 |
| format | Article |
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10
–
13
having the EGCG analogs conjugated to the
d
-glucosyl azide were synthesized by carrying out the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, and were evaluated for their cytotoxicities against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) using MTT assays. Compounds
10
and
11
showed the highest levels of cytotoxicity against the HL-60 cells with IC
50
values of 4.57 and 3.78 μM, respectively, and showed moderate selectivity toward cancer cell lines. Compound
11
was also shown to induce apoptosis in HL-60 cells. Most notably, inclusion of the perbutyrylated glucose residue in an EGCG derivative was concluded to lead to increased anticancer activity.</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-021-02726-5</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Alkynes ; Anticancer properties ; Antitumor activity ; Apoptosis ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Bioorganic Chemistry ; Biotechnology ; Cancer ; Cycloaddition ; Cytotoxicity ; Epigallocatechin-3-gallate ; Inorganic Chemistry ; Medicinal Chemistry ; Original Research ; Pharmacology/Toxicology ; Selectivity ; Toxicity ; Tumor cell lines</subject><ispartof>Medicinal chemistry research, 2021-06, Vol.30 (6), p.1240-1248</ispartof><rights>The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021</rights><rights>The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-8a932fd2ffe7ede26fa800f004a39522323520483762296ccb3224b4cf1cf7363</citedby><cites>FETCH-LOGICAL-c319t-8a932fd2ffe7ede26fa800f004a39522323520483762296ccb3224b4cf1cf7363</cites><orcidid>0000-0002-2367-3617</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00044-021-02726-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00044-021-02726-5$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,778,782,27911,27912,41475,42544,51306</link.rule.ids></links><search><creatorcontrib>Shi, Bo-Ya</creatorcontrib><creatorcontrib>Wang, Ze-Hao</creatorcontrib><creatorcontrib>Zhang, Ning</creatorcontrib><creatorcontrib>Xie, Yin-Rong</creatorcontrib><creatorcontrib>Sun, Xiu-Li</creatorcontrib><creatorcontrib>Yang, Hao-Nan</creatorcontrib><creatorcontrib>Wu, Yi-Long</creatorcontrib><creatorcontrib>Zi, Cheng-Ting</creatorcontrib><creatorcontrib>Wang, Xuan-Jun</creatorcontrib><creatorcontrib>Sheng, Jun</creatorcontrib><title>Syntheses and anticancer activities of novel glucosylated (−)-epigallocatechin-3-gallate derivatives linked via triazole rings</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>Novel glucosylated (-)-epigallocatechin-3-gallate derivatives
10
–
13
having the EGCG analogs conjugated to the
d
-glucosyl azide were synthesized by carrying out the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, and were evaluated for their cytotoxicities against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) using MTT assays. Compounds
10
and
11
showed the highest levels of cytotoxicity against the HL-60 cells with IC
50
values of 4.57 and 3.78 μM, respectively, and showed moderate selectivity toward cancer cell lines. Compound
11
was also shown to induce apoptosis in HL-60 cells. Most notably, inclusion of the perbutyrylated glucose residue in an EGCG derivative was concluded to lead to increased anticancer activity.</description><subject>Alkynes</subject><subject>Anticancer properties</subject><subject>Antitumor activity</subject><subject>Apoptosis</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Biotechnology</subject><subject>Cancer</subject><subject>Cycloaddition</subject><subject>Cytotoxicity</subject><subject>Epigallocatechin-3-gallate</subject><subject>Inorganic Chemistry</subject><subject>Medicinal Chemistry</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Selectivity</subject><subject>Toxicity</subject><subject>Tumor cell lines</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9UD1PwzAQtRBIlMIfYIrEAoPBPsdJOqKKL6kSAzBbrmO3LsYJdhqpTIzM_ER-CS5BYmM43b27e-90D6FjSs4pIeVFJITkOSZAU5RQYL6DRpTzHFcUyG6qSaqBA9tHBzGuCGElyfkIvT9sfLfUUcdM-jpFZ5X0SodMqs72trNp0pjMN7122cKtVRM3Tna6zk6_Pj7PsG7tQjrXqNRTS-sxw1ucUFbrYHuZVJKEs_45cXorsy5Y-dY4nQXrF_EQ7Rnpoj76zWP0dH31OL3Fs_ubu-nlDCtGJx2u5ISBqcEYXepaQ2FkRYhJX0s24QAMGAeSV6wsACaFUnMGkM9zZagyJSvYGJ0Mum1oXtc6dmLVrINPJwVwBpSVvGBpC4YtFZoYgzaiDfZFho2gRGydFoPTIjktfpwWPJHYQIrt9iUd_qT_YX0DX36Dcg</recordid><startdate>20210601</startdate><enddate>20210601</enddate><creator>Shi, Bo-Ya</creator><creator>Wang, Ze-Hao</creator><creator>Zhang, Ning</creator><creator>Xie, Yin-Rong</creator><creator>Sun, Xiu-Li</creator><creator>Yang, Hao-Nan</creator><creator>Wu, Yi-Long</creator><creator>Zi, Cheng-Ting</creator><creator>Wang, Xuan-Jun</creator><creator>Sheng, Jun</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-2367-3617</orcidid></search><sort><creationdate>20210601</creationdate><title>Syntheses and anticancer activities of novel glucosylated (−)-epigallocatechin-3-gallate derivatives linked via triazole rings</title><author>Shi, Bo-Ya ; Wang, Ze-Hao ; Zhang, Ning ; Xie, Yin-Rong ; Sun, Xiu-Li ; Yang, Hao-Nan ; Wu, Yi-Long ; Zi, Cheng-Ting ; Wang, Xuan-Jun ; Sheng, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-8a932fd2ffe7ede26fa800f004a39522323520483762296ccb3224b4cf1cf7363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkynes</topic><topic>Anticancer properties</topic><topic>Antitumor activity</topic><topic>Apoptosis</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Bioorganic Chemistry</topic><topic>Biotechnology</topic><topic>Cancer</topic><topic>Cycloaddition</topic><topic>Cytotoxicity</topic><topic>Epigallocatechin-3-gallate</topic><topic>Inorganic Chemistry</topic><topic>Medicinal Chemistry</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Selectivity</topic><topic>Toxicity</topic><topic>Tumor cell lines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shi, Bo-Ya</creatorcontrib><creatorcontrib>Wang, Ze-Hao</creatorcontrib><creatorcontrib>Zhang, Ning</creatorcontrib><creatorcontrib>Xie, Yin-Rong</creatorcontrib><creatorcontrib>Sun, Xiu-Li</creatorcontrib><creatorcontrib>Yang, Hao-Nan</creatorcontrib><creatorcontrib>Wu, Yi-Long</creatorcontrib><creatorcontrib>Zi, Cheng-Ting</creatorcontrib><creatorcontrib>Wang, Xuan-Jun</creatorcontrib><creatorcontrib>Sheng, Jun</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shi, Bo-Ya</au><au>Wang, Ze-Hao</au><au>Zhang, Ning</au><au>Xie, Yin-Rong</au><au>Sun, Xiu-Li</au><au>Yang, Hao-Nan</au><au>Wu, Yi-Long</au><au>Zi, Cheng-Ting</au><au>Wang, Xuan-Jun</au><au>Sheng, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and anticancer activities of novel glucosylated (−)-epigallocatechin-3-gallate derivatives linked via triazole rings</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2021-06-01</date><risdate>2021</risdate><volume>30</volume><issue>6</issue><spage>1240</spage><epage>1248</epage><pages>1240-1248</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>Novel glucosylated (-)-epigallocatechin-3-gallate derivatives
10
–
13
having the EGCG analogs conjugated to the
d
-glucosyl azide were synthesized by carrying out the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, and were evaluated for their cytotoxicities against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) using MTT assays. Compounds
10
and
11
showed the highest levels of cytotoxicity against the HL-60 cells with IC
50
values of 4.57 and 3.78 μM, respectively, and showed moderate selectivity toward cancer cell lines. Compound
11
was also shown to induce apoptosis in HL-60 cells. Most notably, inclusion of the perbutyrylated glucose residue in an EGCG derivative was concluded to lead to increased anticancer activity.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s00044-021-02726-5</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-2367-3617</orcidid></addata></record> |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Alkynes Anticancer properties Antitumor activity Apoptosis Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Biotechnology Cancer Cycloaddition Cytotoxicity Epigallocatechin-3-gallate Inorganic Chemistry Medicinal Chemistry Original Research Pharmacology/Toxicology Selectivity Toxicity Tumor cell lines |
| title | Syntheses and anticancer activities of novel glucosylated (−)-epigallocatechin-3-gallate derivatives linked via triazole rings |
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