Reactions of BODIPY Fluorophore with Cupric Nitrate

Yang, Lijing; Yalagala, Ravi Shekar; Hutton, Stephanie; Lough, Alan J.; Yan, Hongbin

doi:10.1055/s-0034-1379108

Cited by 7 publications

(6 citation statements)

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“…No trace of the alternative O-alkylated derivative or the 4-hydroxyphenyl-regioisomer were detected. The method allowed us to fluorescently label partially protected L-tyrosine (57) and a polyfunctional natural product such as resveratrol (58). The reaction with the tyrosine derivative proceeded with high chemo-and regioselectivity and was fully compatible with the presence of the carbamate and the methyl ester groups.…”

Section: Scheme 6 Reaction With Halogen and Phosphorous Nucleophilesmentioning

confidence: 99%

Acetoxymethyl-BODIPY dyes: a universal platform for the fluorescent labeling of nucleophiles

et al. 2022

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Section: Scheme 6 Reaction With Halogen and Phosphorous Nucleophilesmentioning

confidence: 99%

Acetoxymethyl-BODIPY dyes: a universal platform for the fluorescent labeling of nucleophiles

et al. 2022

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“…No trace of the alternative O-alkylated derivative, nor the 4-hydroxyphenyl-regioisomer could be detected. The method allowed us to fluorescently label partially protected L-tyrosine (57) and a polyfunctional natural product such as resveratrol (58). The reaction with the tyrosine derivative proceeded with high chemo-and regioselectivity, and was fully compatible with the presence of the carbamate and the methyl ester groups.…”

Section: C-nucleophilesmentioning

confidence: 99%

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

Blázquez-Moraleja

Maierhofer

Mann

et al. 2022

Preprint

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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.

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“…Among these, installation of nitro groups into BODIPY core represents a useful approach to functionalize BODIPY (Ulrich et al, 2012;Esnal et al, 2013;Gupta et al, 2013). In this respect, while BODIPY fluorophores with nitro ISSN 2056-9890 groups are poorly fluorescent, their fluorescence is usually restored upon reduction of nitro to amine (Yang et al, 2014;Yang et al, 2017). We previously reported the treatment of fully substituted BODIPY, 4,4-difluoro-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene 1 with cupric nitrate under various conditions (Yang et al, 2014), leading to the introduction of nitro-, nitromethyl-, hydroxymethyl-and carboxyaldehyde into BODIPY (see Scheme below).…”

Section: Chemical Contextmentioning

confidence: 99%