Carbohydrate-based inducers of cellular stress for targeting cancer cells
[Display omitted] Small molecules that block the altered metabolism in cancer or increase the production of reactive oxygen species (ROS) are emerging as potential anti-cancer agents. Considering that various carbohydrates can be used for cellular energetics or protein N-glycosylation of which inter...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2016-03, Vol.26 (5), p.1452-1456 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 26 |
| creator | Ndombera, Fidelis T. VanHecke, Garrett C. Nagi, Shima Ahn, Young-Hoon |
| description | [Display omitted]
Small molecules that block the altered metabolism in cancer or increase the production of reactive oxygen species (ROS) are emerging as potential anti-cancer agents. Considering that various carbohydrates can be used for cellular energetics or protein N-glycosylation of which interruption can lead to cellular stress, we have synthesized and evaluated a library of N-aryl glycosides for induction of ROS and cytotoxicity in H1299 cancer cell line. Two N-aryl glycosides (K8 and H8) were identified that induce about 2-fold induction of ROS and cytotoxicity in H1299 cells. We further showed that the acetylated form of K8 (K8A) activates AMPK, and stabilizes p53 in HEK293 cells, and induce a higher cytotoxicity than 2-deoxy-d-glucose in H1299 cell line. |
| doi_str_mv | 10.1016/j.bmcl.2016.01.063 |
| format | Article |
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Small molecules that block the altered metabolism in cancer or increase the production of reactive oxygen species (ROS) are emerging as potential anti-cancer agents. Considering that various carbohydrates can be used for cellular energetics or protein N-glycosylation of which interruption can lead to cellular stress, we have synthesized and evaluated a library of N-aryl glycosides for induction of ROS and cytotoxicity in H1299 cancer cell line. Two N-aryl glycosides (K8 and H8) were identified that induce about 2-fold induction of ROS and cytotoxicity in H1299 cells. We further showed that the acetylated form of K8 (K8A) activates AMPK, and stabilizes p53 in HEK293 cells, and induce a higher cytotoxicity than 2-deoxy-d-glucose in H1299 cell line.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2016.01.063</identifier><identifier>PMID: 26832785</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>2-Deoxy-d-glucose ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cell Survival - drug effects ; Cytotoxicity ; Dose-Response Relationship, Drug ; Glycosides - chemical synthesis ; Glycosides - chemistry ; Glycosides - pharmacology ; HEK293 Cells ; Humans ; Molecular Structure ; N-Aryl glycoside library ; Reactive Oxygen Species - metabolism ; Reactive oxygen species inducer ; Stress, Physiological - drug effects ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2016-03, Vol.26 (5), p.1452-1456</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-8e7c452b0d826868f16348bc325dd382824e1a193f5c0c322e4533a2fee488b3</citedby><cites>FETCH-LOGICAL-c389t-8e7c452b0d826868f16348bc325dd382824e1a193f5c0c322e4533a2fee488b3</cites><orcidid>0000-0002-4710-2464 ; 0000-0003-0765-3074 ; 0000-0002-3476-1671</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2016.01.063$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26832785$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ndombera, Fidelis T.</creatorcontrib><creatorcontrib>VanHecke, Garrett C.</creatorcontrib><creatorcontrib>Nagi, Shima</creatorcontrib><creatorcontrib>Ahn, Young-Hoon</creatorcontrib><title>Carbohydrate-based inducers of cellular stress for targeting cancer cells</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Small molecules that block the altered metabolism in cancer or increase the production of reactive oxygen species (ROS) are emerging as potential anti-cancer agents. Considering that various carbohydrates can be used for cellular energetics or protein N-glycosylation of which interruption can lead to cellular stress, we have synthesized and evaluated a library of N-aryl glycosides for induction of ROS and cytotoxicity in H1299 cancer cell line. Two N-aryl glycosides (K8 and H8) were identified that induce about 2-fold induction of ROS and cytotoxicity in H1299 cells. We further showed that the acetylated form of K8 (K8A) activates AMPK, and stabilizes p53 in HEK293 cells, and induce a higher cytotoxicity than 2-deoxy-d-glucose in H1299 cell line.</description><subject>2-Deoxy-d-glucose</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cell Survival - drug effects</subject><subject>Cytotoxicity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Glycosides - chemical synthesis</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - pharmacology</subject><subject>HEK293 Cells</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>N-Aryl glycoside library</subject><subject>Reactive Oxygen Species - metabolism</subject><subject>Reactive oxygen species inducer</subject><subject>Stress, Physiological - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkD1PwzAQhi0EoqXwBxhQRpYEf8WxJRZU8VGpEksHNsuxLyVV0hQ7Qeq_x6GFETHd6fS8r04PQtcEZwQTcbfJytY2GY17hkmGBTtBU8IFTxnH-SmaYiVwKhV_m6CLEDYYE445P0cTKiSjhcynaDE3vuze986bHtLSBHBJvXWDBR-SrkosNM3QGJ-E3kMISdX5pDd-DX29XSfWbCP4DYVLdFaZJsDVcc7Q6ulxNX9Jl6_Pi_nDMrVMqj6VUFie0xI7Gb8QsiKCcVlaRnPnmKSSciCGKFblFscrBZ4zZmgFwKUs2QzdHmp3vvsYIPS6rcP4gNlCNwRNCoVVLgql_oGKXFHKCxpRekCt70LwUOmdr1vj95pgPcrWGz3K1qNsjYmOsmPo5tg_lC2438iP3QjcHwCIPj5r8DrYGqIyV3uwvXZd_Vf_Fwkqj1o</recordid><startdate>20160301</startdate><enddate>20160301</enddate><creator>Ndombera, Fidelis T.</creator><creator>VanHecke, Garrett C.</creator><creator>Nagi, Shima</creator><creator>Ahn, Young-Hoon</creator><general>Elsevier Ltd</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-4710-2464</orcidid><orcidid>https://orcid.org/0000-0003-0765-3074</orcidid><orcidid>https://orcid.org/0000-0002-3476-1671</orcidid></search><sort><creationdate>20160301</creationdate><title>Carbohydrate-based inducers of cellular stress for targeting cancer cells</title><author>Ndombera, Fidelis T. ; VanHecke, Garrett C. ; Nagi, Shima ; Ahn, Young-Hoon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-8e7c452b0d826868f16348bc325dd382824e1a193f5c0c322e4533a2fee488b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>2-Deoxy-d-glucose</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cell Survival - drug effects</topic><topic>Cytotoxicity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Glycosides - chemical synthesis</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - pharmacology</topic><topic>HEK293 Cells</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>N-Aryl glycoside library</topic><topic>Reactive Oxygen Species - metabolism</topic><topic>Reactive oxygen species inducer</topic><topic>Stress, Physiological - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ndombera, Fidelis T.</creatorcontrib><creatorcontrib>VanHecke, Garrett C.</creatorcontrib><creatorcontrib>Nagi, Shima</creatorcontrib><creatorcontrib>Ahn, Young-Hoon</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><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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ndombera, Fidelis T.</au><au>VanHecke, Garrett C.</au><au>Nagi, Shima</au><au>Ahn, Young-Hoon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbohydrate-based inducers of cellular stress for targeting cancer cells</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2016-03-01</date><risdate>2016</risdate><volume>26</volume><issue>5</issue><spage>1452</spage><epage>1456</epage><pages>1452-1456</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Small molecules that block the altered metabolism in cancer or increase the production of reactive oxygen species (ROS) are emerging as potential anti-cancer agents. Considering that various carbohydrates can be used for cellular energetics or protein N-glycosylation of which interruption can lead to cellular stress, we have synthesized and evaluated a library of N-aryl glycosides for induction of ROS and cytotoxicity in H1299 cancer cell line. Two N-aryl glycosides (K8 and H8) were identified that induce about 2-fold induction of ROS and cytotoxicity in H1299 cells. We further showed that the acetylated form of K8 (K8A) activates AMPK, and stabilizes p53 in HEK293 cells, and induce a higher cytotoxicity than 2-deoxy-d-glucose in H1299 cell line.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26832785</pmid><doi>10.1016/j.bmcl.2016.01.063</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-4710-2464</orcidid><orcidid>https://orcid.org/0000-0003-0765-3074</orcidid><orcidid>https://orcid.org/0000-0002-3476-1671</orcidid></addata></record> |
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| subjects | 2-Deoxy-d-glucose Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Cell Survival - drug effects Cytotoxicity Dose-Response Relationship, Drug Glycosides - chemical synthesis Glycosides - chemistry Glycosides - pharmacology HEK293 Cells Humans Molecular Structure N-Aryl glycoside library Reactive Oxygen Species - metabolism Reactive oxygen species inducer Stress, Physiological - drug effects Structure-Activity Relationship |
| title | Carbohydrate-based inducers of cellular stress for targeting cancer cells |
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