| Literature DB >> 28465102 |
Guanghui Zong1, Melissa Hirsch1, Collin Mondrik1, Zhijian Hu1, Wei Q Shi2.
Abstract
Ipomoeassin F is a plant-derived macrocyclic glycolipid with single-digit nanomolar IC50 values against cancer cell growth. In previous structure-activity relationship studies, we have demonstrated that certain modifications around the fucoside moiety did not cause significant cytotoxicity loss. To further elucidate the effect of the fucoside moiety on the biological activity, we describe here the design and synthesis of several fucose-truncated monosaccharide analogues of ipomoeassin F. Subsequent biological evaluation strongly suggests that the 6-membered ring of the fucoside moiety is essential to the overall conformation of the molecule, thereby influencing bioactivity.Entities:
Keywords: BVBGTMCKLNYQPX-PDDTYTPCSA-N; CIWXVLPZBJOWOE-SNVBAGLBSA-N; Cytotoxicity; DNGWMNZMRALKSR-IAQQVRHFSA-N; GHFRBGNLAWACRU-VJVLEUCCSA-N; GSKULKPUBPOPEK-WDYNDCKDSA-N; HLKZABNXLHJROG-UHZDTLPASA-N; HRNYGVKDTOFUGG-CEGUSXFXSA-N; IWTUVIHOHSFHOR-MRFULHKYSA-N; Ipomoeassin F; KVGYCBMYWWSTJF-ZEBMQPPJSA-N; LCSGJDKMNRSKBV-GFCCVEGCSA-N; MGRJFGLICMEZQW-UHFFFAOYSA-N; MJYFDKSBTYGFMR-NQYVGIDLSA-N; MQUBXPPFSCCADG-ZWHJMUPSSA-N; Macrolide; Monosaccharide analogues; NDBKVUSDPPZPLV-JJFXFIIRSA-N; NDUPBTSXOSZHON-SECBINFHSA-N; NNASWLXAHWWJHW-LLVKDONJSA-N; ODUVXAVOUUVXHS-OQBDQXSPSA-N; ODWBUFIMGGMMCZ-JLKXFGDHSA-N; Resin glycosides; SUDQQMWMUVLQLI-MHVJIRHVSA-N; VSOPGDDGIMCOHZ-IOQCHWBKSA-N; WOOTYDFHRXXYOH-WSCIJNKFSA-N; ZNKHQZOSZVDWLC-QGLDALQQSA-N
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Year: 2017 PMID： 28465102 PMCID： PMC5502735 DOI： 10.1016/j.bmcl.2017.04.065
Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823