Core remodeling leads to long wavelength fluoro-coumarins

Matikonda, Siddharth S.; Ivanic, Joseph; Gómez, Miguel Ángel Sánchez; Hammersley, Gabrielle; Schnermann, Martin J.

doi:10.1039/d0sc02566f

Cited by 43 publications

(36 citation statements)

References 53 publications

(86 reference statements)

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“…SNAP/Halo-tag fusions) make them an attractive choice for the visualization and interrogation of biomolecular function. [3] Several chemical scaffolds, for instance nitrobenzodioxazoles (NBDs) [4] and coumarins [5] , remain interesting synthetic targets, yet xanthene dyes, which include tetramethylrhodamine (TMR) and silicon rhodamine (SiR), experienced a renaissance in terms of novel modifications to tune and boost important parameters, such as color, brightness, lifetime and reactivity. [6][7][8][9][10] However, and best to our knowledge, isotopic labelling has not been among this repertoire.…”

Section: Main Textmentioning

confidence: 99%

Deuterated rhodamines for protein labelling in nanoscopy

Roßmann

Akkaya

Charbonnier

et al. 2020

Preprint

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Rhodamine molecules are setting benchmarks in fluorescence microscopy. Herein, we report the deuterium (d12) congeners of tetramethyl(silicon)rhodamine, obtained by isotopic labelling of the four methyl groups, which improves photophysical (i.e. brightness, lifetimes) and chemical (i.e. bleaching) properties. We explore this finding for SNAP- and Halo-tag labelling, and highlight enhanced properties in several applications, such as Foerster resonance energy transfer, fluorescence activated cell sorting, fluorescence lifetime microscopy and stimulated emission depletion nanoscopy. We envision deuteration as a generalizable concept to improve existing and develop new Chemical Biology Probes.

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Section: Main Textmentioning

confidence: 99%

Deuterated rhodamines for protein labelling in nanoscopy

Roßmann

Akkaya

Charbonnier

et al. 2020

Preprint

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“…45,46 Additionally, coumarins have been incorporated into other motifs to achieve bright NIR emission. [47][48][49][50][51] The small size of the coumarin core would also likely require only minimal enzyme engineering to identify complementary luciferases. Given the unique structure of the CouLuc-1s, we further anticipated that the analogs could be used for multi-component imaging with other red-emitting probes, including AkaLumine/Akaluc and furimazine/Antares.…”

Section: Introductionmentioning

confidence: 99%

Coumarin luciferins and mutant luciferases for robust multi-component bioluminescence imaging

et al. 2021

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“…4) (18,19) illustrates a significant reduction in the molecular weight of KR-1. Together with their recently described low molecular weight, NIR-emitting fluorocoumarins, this team has established themselves as leaders in the development of low molecular weight red-shifted dyes (33).…”

Section: Photophysical Propertiesmentioning

confidence: 99%

Heteroatom‐Substituted Xanthene Fluorophores Enter the Shortwave‐Infrared Region^†

Brøndsted

Stains

2021

Photochem & Photobiology

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This article is a highlight of the paper by Ivanic and Schnermann et al. in this issue of Photochemistry and Photobiology (Daly et al. Photochem. Photobiol. 2022). The collaborative team utilized computational approaches to investigate the influence of electron-withdrawing groups at the 10 0 position of tetramethylrhodamine (TMR). Leveraging this information, the team was able to extend the emission of the TMR scaffold into the shortwave-infrared region (SWIR, 1000-2500 nm) by incorporation of a ketone functional group at the 10 0 position (Daly et al. Photochem. Photobiol. 2022). This work provides the first example of a TMR derivative with peak SWIR emission (k abs : 862 nm, k em : 1058 nm). The authors utilize the ketone rhodamine scaffold to generate fluorogenic, pH-responsive reporters. This work demonstrates the potential of the classic xanthene scaffold for use as a SWIR reporter, an important step in the ultimate expansion of the repertoire of small-molecule organic fluorophore scaffolds available for deep-tissue imaging applications.

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Core remodeling leads to long wavelength fluoro-coumarins

Abstract:
Fluoro-Coumarins are a novel class of far-red and near-infrared solvent sensitive dyes of exceptionally low molecular weight.

Cited by 43 publications

References 53 publications

Deuterated rhodamines for protein labelling in nanoscopy

Deuterated rhodamines for protein labelling in nanoscopy

Coumarin luciferins and mutant luciferases for robust multi-component bioluminescence imaging

Heteroatom‐Substituted Xanthene Fluorophores Enter the Shortwave‐Infrared Region^†

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Core remodeling leads to long wavelength fluoro-coumarins

Abstract: Fluoro-Coumarins are a novel class of far-red and near-infrared solvent sensitive dyes of exceptionally low molecular weight.

Cited by 43 publications

References 53 publications

Deuterated rhodamines for protein labelling in nanoscopy

Deuterated rhodamines for protein labelling in nanoscopy

Coumarin luciferins and mutant luciferases for robust multi-component bioluminescence imaging

Heteroatom‐Substituted Xanthene Fluorophores Enter the Shortwave‐Infrared Region†

Contact Info

Product

Resources

About

Abstract:
Fluoro-Coumarins are a novel class of far-red and near-infrared solvent sensitive dyes of exceptionally low molecular weight.

Heteroatom‐Substituted Xanthene Fluorophores Enter the Shortwave‐Infrared Region^†