Design, synthesis and biological evaluation of fucose-truncated monosaccharide analogues of ipomoeassin F.
Bioorg Med Chem Lett
; 27(12): 2752-2756, 2017 06 15.
Article
em En
| MEDLINE
| ID: mdl-28465102
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.
Palavras-chave
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
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Glicoconjugados
/
Desenho de Fármacos
/
Fucose
/
Antineoplásicos Fitogênicos
Limite:
Humans
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article