Fluorinated analogues of lipidic dialkynylcarbinol pharmacophores: synthesis and cytotoxicity in HCT116 cancer cells

Pauline Rullière (1) , François Lizeaux (1) , Etienne Joly (2) , Stéphanie Ballereau (1) , Hafida Gaspard (1) , Valérie Maraval (3) , Rémi Chauvin (3) , Yves Génisson (1)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 IPBS - Institut de pharmacologie et de biologie structurale
3 LCC - Laboratoire de chimie de coordination

Lipidic alkynylcarbinols (LACs) have been identified as potential antitumor compounds, and a thorough understanding of their pharmacophoric environment is now required to elucidate their biological mode of action. In the dialkynylcarbinol (DAC) series, a specific study of the pharmacophore potential has been undertaken by focusing on the synthesis of three fluorinated derivatives followed by their biological evaluation. This work highlights the requirement of an electron-rich secondary carbinol center as a key structure for cytotoxicity in HCT116 cells.

Mots clés: Alkynylcarbinol; Fluorine; Alkyne; Pharmacophore design; Cytotoxicity

Domaines: Chimie de coordination

Pauline Rullière, François Lizeaux, Etienne Joly, Stéphanie Ballereau, Hafida Gaspard, et al.. Fluorinated analogues of lipidic dialkynylcarbinol pharmacophores: synthesis and cytotoxicity in HCT116 cancer cells. French-Ukrainian Journal of Chemistry, 2019, 7 (1), pp.1-9. ⟨10.17721/fujcV7I1P1-9⟩. ⟨hal-02335107⟩