Oral Comm

Projet
 
Martine DEMEUNYNCK, Isabelle BAUSSANNE,   
Titre
The indolizine: from bioactive heterocycle to fluorescent modular platform for cellular target identification  
Auteurs
Martine Demeunynck*, Isabelle Baussanne, Simon Bonte, Marie Arvin-Berod, Rodica Dinica, Bianca Furdui, Ioana Ottilia-Ghinea
Année
2016
Résumé
Indolizine, or pyrrolo[1,2-a]pyridine, is a fluorescent heterocycle, that may be found both in natural and synthetic bioactive molecules. Among all the synthetic methodologies found in the literature to prepare indolizinic compounds, the [3+2]-cycloaddition between pyridium ylides and alkynes allows the easy and fine modulation of the indolizine core. We have investigated the reactivity of 4-substituted pyridinium salts with various electron-deficient alkynes in mild conditions, and prepared series of mono or bis-indolizines that were successfully evaluated as antioxidants and antibacterial agents. The intrinsic fluorescence of indolizine was used to conceive multipodal plateforms, from easily accessible reactants, that would find applications to functionalize (bio)materials or as tools in molecular biology. As an application in chemical proteomics, a biotine-drug structure was synthesized, immobilized onto avidine agarose and used to capture the proteins of interest as candidate targets of a series of anti-angiogenic agents