Acetoxymethyl-BODIPY dyes: a universal platform for the fluorescent labeling of nucleophiles. Issue 21 (31st August 2022)

• Record Type: Journal Article
• Authors: Blázquez-Moraleja, Alberto; Maierhofer, Larissa; Mann, Enrique; Prieto-Montero, Ruth; Oliden-Sánchez, Ainhoa; Celada, Lucía; Martínez-Martínez, Virginia; Chiara, María-Dolores; Chiara, Jose Luis
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 21(2022)
• Page Start: 5774
• Page End: 5789
• Publication Date: 2022-08-31
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01099b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A general and robust methodology has been developed for the direct incorporation of a wide variety of C -, N -, P -, O -, S -, and halo-nucleophiles into functional BODIPY conjugates in a single reaction step. Abstract : Current methods for the preparation of functional small-molecule fluorophores generally require labor-intensive, multi-step synthetic routes for all the major chromophoric groups. In spite of recent significant contributions from numerous laboratories, the paucity of rapid, straightforward and wide-scope synthetic strategies in this field is limiting the development of advanced probes for bioimaging, sensing and therapeutic applications. We describe herein a general and robust methodology for the one-step fluorescent labeling of a wide variety of molecules having C -, N -, P -, O -, S -, or halide-nucleophilic centers, using stable and readily available acetoxymethyl-BODIPYs as reagents in the presence of an acid catalyst. This modular methodology allows a very facile preparation of mono- and di-functional probes incorporating a broad assortment of biomolecules, enzyme cofactors, natural products, and other chromophores, as well as chemical functionalities for a wide range of applications including bioorthogonal conjugation, polymerization, and supramolecular chemistry, among others. The photophysical properties and preliminary applications of the new probes in live-cell imaging were also studied. The described strategy enables the high-throughput engineering of novel BODIPY dyes with diverse functionalities for basic and applied science with potential for innovative technological applications.