Tacke Eléonore, Hoang Minh-Duc, Tatoueix Kevin, Keromnes Benoît, Van Eslande Elsa, Durand Philippe, Pieters Gregory, Chevalier Arnaud
Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301 91198 Gif-sur-Yvette France
Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE 91191 Gif-sur-Yvette France.
Chem Sci. 2023 May 3;14(22):6000-6010. doi: 10.1039/d3sc01365k. eCollection 2023 Jun 7.
A simple and easy-to-implement process based on a nucleophilic aromatic substitution reaction with a wide variety of nucleophiles on a fluorinated CinNapht is described. This process has the key advantage of introducing multiple functionalities at a very late stage, thus providing access to new applications including the synthesis of photostable and bioconjugatable large Stokes shift red emitting dyes and selective organelle imaging agents, as well as AIEE-based wash-free lipid droplet imaging in live cells with high signal-to-noise ratio. The synthesis of bench-stable CinNapht-F has been optimized and can be reproduced on a large scale, making it an easy-to-store starting material that can be used at will to prepare new molecular imaging tools.
描述了一种基于亲核芳香取代反应的简单且易于实施的过程,该反应可在氟化的CinNapht上与多种亲核试剂发生反应。此过程的关键优势在于能够在非常后期的阶段引入多种功能,从而为新的应用提供了途径,包括合成光稳定且可生物共轭的大斯托克斯位移红色发射染料和选择性细胞器成像剂,以及在活细胞中基于聚集诱导发光增强效应的无洗涤脂滴成像,且具有高信噪比。稳定的CinNapht-F的合成已得到优化,并且可以大规模重现,使其成为一种易于储存的起始原料,可随意用于制备新的分子成像工具。