Tuning Directed Photooxidation Induced Conversion of Pyrrole-based Styryl Coumarins Dual-Color Photoconverters.
Fiche publication
Date publication
janvier 2023
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr KLYMCHENKO Andrey
Tous les auteurs :
Saladin L, Dal Pra O, Klymchenko A, Didier P, Collot M
Lien Pubmed
Résumé
Dual-emissive photoconvertible fluorophores (DPCFs) are powerful tools in bioimaging to unambiguously track labelled cells in bioimaging. We recently introduced a new rational mechanism called directed photooxidation induced conversion (DPIC) enabling to obtain efficient DPCFs by conjugating a coumarin to aromatic singlet oxygen reactive moieties (ASORMs). Pyrrole was found to be a suitable ASORM as it provided a high hypsochromic shift along with a fast and efficient conversion. By synthesizing various pyrrole-based styryl coumarin dyes, we herein show that the photoconversion properties, including the quantum yield of photoconversion and the chemical yield of conversion can be tuned by chemical modification of the pyrrole. These modifications led to an improved dual emissive converter, SCP-Boc, which displayed a high brightness and an enhanced photoconversion yield of 63%. SCP-Boc was successfully used to sequentially photoconvert cells by laser scanning confocal microscopy.
Mots clés
Photoconversion * Photoswitching * Photooxidation * Fluorescent probes * Molecular tuning
Référence
Chemistry. 2023 01 31;: