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Alkyne‐Tagged Analogue of Jaspine B: New Tool for Identifying Jaspine B Mode of Action
Author(s) -
Rozié Alexandrine,
Santos Cécile,
Fabing Isabelle,
Calsou Patrick,
Britton Sébastien,
Génisson Yves,
Ballereau Stéphanie
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800496
Subject(s) - enantiomer , alkyne , chemistry , mode of action , cytotoxicity , derivative (finance) , stereochemistry , click chemistry , cyclopropene , combinatorial chemistry , in vitro , biochemistry , organic chemistry , economics , financial economics , catalysis
The first biologically relevant clickable probe related to the antitumor marine lipid jaspine B is reported. The concise synthetic route to both enantiomers relied on the supercritical fluid chromatography (SFC) enantiomeric resolution of racemic materials. The eutomeric dextrogyre derivative represents the first jaspine B analogue with enhanced cytotoxicity with IC 50 down to 30 n m . These enantiomeric probes revealed a chiralitydependent cytoplasmic imaging of U2OS cancer cells by in situ click labeling.