Nebraska Red: a phosphinate-based near-infrared fluorophore scaffold for chemical biology applications

Zhou, Xinqi; Lai, Rui; Beck, Jon R.; Li, Hui; Stains, Cliff I.

doi:10.1039/c6cc05717a

Cited by 129 publications

(145 citation statements)

References 34 publications

(35 reference statements)

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“…With respect to the predecessor 1 c , the performed changes of the molecular structure resulted in a remarkable 12 103 cm 1 (362 nm) bathochromic shift of fluorescence demonstrated by 6 c . It is important to note that the emission characteristics of 5 c and 6 c in organic solvents place them among the most efficient and red shifted organophosphorus dyes reported to date . The photoinduced intramolecular charge transfer leads in turn to large Stokes shifts of approximately 7600 cm −1 (280 nm, 5 c ) and 4700 cm −1 (230 nm, 6 c Figure ), minimizing the reabsorption, which is crucial for practical imaging applications…”

Section: Resultsmentioning

confidence: 99%

Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

Belyaev

Chen

Liu

et al. 2019

Chemistry A European J

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Rationally designed cationic phospha‐polyaromatic fluorophores were prepared through intramolecular cyclization of the tertiary ortho ‐(acene)phenylene‐phosphines mediated by Cu II triflate. As a result of phosphorus quaternization, heterocyclic phosphonium salts 1 c – 3 c , derived from naphthalene, phenanthrene, and anthracene cores, exhibited very intense blue to green fluorescence ( Φ em =0.38–0.99) and high photostability in aqueous medium. The structure–emission relationship was further investigated by tailoring the electron‐donating functions to the anthracene moiety to give dyes 4 c – 6 c with charge‐transfer character. The latter significantly decreases the emission energy to reach near‐IR region. Thus, the intramolecular phosphacyclization renders an ultra‐wide tuning of fluorescence from 420 nm ( 1 c ) to 780 nm ( 6 c ) in solution, extended to 825 nm for 6 c in the solid state with quantum efficiency of approximately 0.07. The physical behavior of these new dyes was studied spectroscopically, crystallographically, and electrochemically, whereas computational analysis was used to correlate the experimental data with molecular electronic structures. The excellent stability, water solubility, and attractive photophysical characteristics make these phosphonium heterocycles powerful tools in cell imaging.

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Section: Resultsmentioning

confidence: 99%

Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

Belyaev

Chen

Liu

et al. 2019

Chemistry A European J

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“…[6] Such P = O-substituted fluorophores enable the acquisition of repeated images in stimulated emission depletion (STED) microscopy,where the fluorophores are exposed to an extremely intense depletion laser field. Indeed, the replacement of the endocyclic oxygen atom in xanthene scaffolds with aP = Om oiety generates the corresponding fluorescein (POF), [8] rhodol (PORL), [9] and rhodamine (POR) [10] derivatives ( Figure 1a), which emit fluorescence in the far-red to NIR region in PBS (pH 7.4). Indeed, the replacement of the endocyclic oxygen atom in xanthene scaffolds with aP = Om oiety generates the corresponding fluorescein (POF), [8] rhodol (PORL), [9] and rhodamine (POR) [10] derivatives ( Figure 1a), which emit fluorescence in the far-red to NIR region in PBS (pH 7.4).…”

mentioning

confidence: 99%

A Highly Photostable Near‐Infrared Labeling Agent Based on a Phospha‐rhodamine for Long‐Term and Deep Imaging

et al. 2018

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Various fluorescence microscopy techniques require bright NIR-emitting fluorophores with high chemical and photostability. Now, the significant performance improvement of phosphorus-substituted rhodamine dyes (PORs) upon substitution at the 9-position with a 2,6-dimethoxyphenyl group is reported. The thus obtained dye PREX 710 was used to stain mitochondria in living cells, which allowed long-term and three-color imaging in the vis-NIR range. Moreover, the high fluorescence longevity of PREX 710 allows tracking a dye-labeled biomolecule by single-molecule microscopy under physiological conditions. Deep imaging of blood vessels in mice brain has also been achieved using the bright NIR-emitting PREX 710-dextran conjugate.

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“…Interestingly, our studies have shown that a simple hydrolysis of a bridging phosphinate ethyl ester can yield a 37 nm blue-shift in the emission of the corresponding fluorophore. [5] This experimental observation led us to ask whether chemoselective reactions of novel functional groups in xanthene-based fluorophores could be utilized to afford ratiometric chemodosimeters displaying large shifts in both excitation and emission.…”

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confidence: 99%

Chemoselective Alteration of Fluorophore Scaffolds as a Strategy for the Development of Ratiometric Chemodosimeters

et al. 2017

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Ratiometric sensors generally couple binding events or chemical reactions at a distal site to changes in the fluorescence of a core fluorophore scaffold. However, such approaches are often hindered by spectral overlap of the product and reactant species. We provide a strategy to design ratiometric sensors that display dramatic spectral shifts by leveraging the chemoselective reactivity of novel functional groups inserted within fluorophore scaffolds. As a proof-of-principle, fluorophores containing a borinate (RF620) or silanediol (SiOH2R) functionality at the bridging position of the xanthene ring system are developed as endogenous H2O2 sensors. Both these fluorophores display far-red to near-infrared excitation and emission prior to reaction. Upon oxidation by H2O2 both sensors are chemically converted to tetramethylrhodamine, producing significant (≥66 nm) blue-shifts in excitation and emission maxima. This work provides a new concept for the development of ratiometric probes.

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Nebraska Red: a phosphinate-based near-infrared fluorophore scaffold for chemical biology applications

Cited by 129 publications

References 34 publications

Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

A Highly Photostable Near‐Infrared Labeling Agent Based on a Phospha‐rhodamine for Long‐Term and Deep Imaging

Chemoselective Alteration of Fluorophore Scaffolds as a Strategy for the Development of Ratiometric Chemodosimeters

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