Retinoids Molecular Probes by Late-stage Azide Insertion - Functional Tools to Decrypt Retinoid Metabolism.
Fiche publication
Date publication
août 2024
Journal
Chembiochem : a European journal of chemical biology
Auteurs
Membres identifiés du Cancéropôle Est :
Dr ROCHEL-GUIBERTEAU Natacha, Dr WAGNER Alain, Dr KREZEL Wojciech, Dr CHAUBET Guilhem
Tous les auteurs :
Coulleray J, Kindler A, Rima M, Cahuzac H, Rochel N, Chaubet G, Krezel W, Wagner A
Lien Pubmed
Résumé
Studying the complex and intricate retinoids metabolic pathways by chemical biology approaches requires design and synthesis of biologically functional molecular probes. Only few of such molecular retinoid probes could be found in literature, most of them bearing a molecular structure quite different from natural retinoids. To provide close-to-native retinoid probes, we have developed a versatile late-stage method for the insertion of azide function at the C4 position of several retinoids. This one-step process opens straightforward access to different retinoid and carotenoid probes from commercially available precursors. We have further demonstrated that the different molecular probes retain ability of the original compound to activate genes' transcription, despite azide insertion, highlighting biological activities that were further validated in zebrafish in vivo model. The present work paves the way to future studies on vitamin A's metabolism.
Mots clés
Late stage azidation, molecular probes, retinoids, vitamin A
Référence
Chembiochem. 2024 08 2;:e202300689