Alkyne‐Tagged Analogue of Jaspine B: New Tool for Identifying Jaspine B Mode of Action | Zendy

Rozié Alexandrine | Zendy; Santos Cécile | Zendy; Fabing Isabelle | Zendy; Calsou Patrick | Zendy; Britton Sébastien | Zendy; Génisson Yves | Zendy; Ballereau Stéphanie | Zendy

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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 , chemistry , alkyne , mode of action , cytotoxicity , derivative (finance) , click chemistry , cyclopropene , stereochemistry , 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.

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