Acetoxymethyl-BODIPY Dyes: A Universal Platform for the Fluorescence Labeling of Nucleophiles

06 July 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Current methods for the preparation of functional small-molecule fluorophores generally require labor-intensive, multi-step synthetic routes for all the major chromophore 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 could enable the high-throughput engineering of novel BODIPY dyes with diverse functionalities for basic and applied research with potential for innovative technological applications.

Keywords

fluorescent dyes
BODIPYs
photophysics
bioimaging
fluorescent cell microscopy
bioconjugation
HaloTag
bioorthogonal chemistry
high-throughput synthesis
acid catalysis
carbohydrates
amino acids
resveratrol
lead tetracetate
acetoxylation
azulene
multichromophores
nucleosides
lipids
fluorescense
tetrazines
azides
alkynes
nucleophilic substitution
click chemistry
C-nucleophiles
O-nucleophiles
S-nucleopjiles
N-nucleophiles
Halo-nucleophiles
DFT
photoinduced electron transfer

Supplementary materials

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Description
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Title
Supporting Information 1
Description
Supplementary tables and figures, complete experimental procedures, X-ray diffraction data of compound 9, computational details (PDF)
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Supporting Information 2
Description
Copies of 1H and 13C NMR spectra of all new compounds
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