Alkyne-Tagged Analogue of Jaspine B: New Tool for Identifying Jaspine B Mode of Action

Alexandrine Rozié (1) , Cécile Santos (2) , Isabelle Fabing (2) , Patrick Calsou (1) , Sébastien Britton (1) , Yves Génisson (2) , Stéphanie Ballereau (2)

1 IPBS - Institut de pharmacologie et de biologie structurale
2 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique

The first biologically relevant clickable probe related to the antitumor marine lipid jaspine B is reported. Concise synthetic route to both enantiomers relied on the chiral SCF enantiomeric resolution of racemic materials. The eutomeric dextrogyre derivative represents the first jaspine B analogue with enhanced cytotoxicity with IC50 down to 30 nM. These enantiomeric probes revealed a chiralitydependent cytoplasmic imaging of U2OS cancer cells by in situ click labelling.

Domaines: Chimie

Alexandrine Rozié, Cécile Santos, Isabelle Fabing, Patrick Calsou, Sébastien Britton, et al.. Alkyne-Tagged Analogue of Jaspine B: New Tool for Identifying Jaspine B Mode of Action. ChemBioChem, 2018, 19 (23), pp.2438-2442. ⟨10.1002/cbic.201800496⟩. ⟨hal-02059233⟩