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Synthesis and Structure activity relationships of EGCG Analogues, A Recently Identified Hsp90 Inhibitor
dc.contributor.author | Khandelwal, Anuj | |
dc.contributor.author | Hall, Jessica Ann | |
dc.contributor.author | Blagg, Brian S. J. | |
dc.date.accessioned | 2017-04-13T15:43:23Z | |
dc.date.available | 2017-04-13T15:43:23Z | |
dc.date.issued | 2013-08-16 | |
dc.identifier.citation | Khandelwal, A., Hall, J., & Blagg, B. S. J. (2013). Synthesis and Structure activity relationships of EGCG Analogues, A Recently Identified Hsp90 Inhibitor. The Journal of Organic Chemistry, 78(16), 7859–7884. http://doi.org/10.1021/jo401027r | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/23681 | |
dc.description.abstract | Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90, however structure-activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure-activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Anti-proliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of four most potent analogues was further evaluated by western blot analyses and degradation of Hsp90-dependent client proteins. Prenyl substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as novel scaffold that exhibit Hsp90 inhibitory activity. | en_US |
dc.publisher | American Chemical Society | en_US |
dc.rights | This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo401027r. | en_US |
dc.title | Synthesis and Structure activity relationships of EGCG Analogues, A Recently Identified Hsp90 Inhibitor | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Khandelwal, Anuj | |
kusw.kuauthor | Hall, Jessica | |
kusw.kuauthor | Blagg, Brian S. J. | |
kusw.kudepartment | Medicinal Chemistry | en_US |
dc.identifier.doi | 10.1021/jo401027r | en_US |
dc.identifier.orcid | https://orcid.org/0000-0003-4492-4400 | |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.rights.accessrights | openAccess |