A design concept of long-wavelength fluorescent analogs of rhodamine dyes: replacement of oxygen with silicon atom

Fu, Mengying; Xiao, Yi; Qian, Xuhong; Zhao, Defeng; Xu, Yufang

doi:10.1039/b718544h

Cited by 259 publications

(173 citation statements)

References 51 publications

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“…2). 11 TMDHS exhibited a large bathochromic shift up to 90 nm in the absorption and emission wavelengths as a result of only a single atom change. The electrochemical and calculated data of these dyes indicate that the replacement of the O atom with a Si atom affected both the HOMO and LUMO energy levels (Fig.…”

Section: Design Concept Of Far-red To Near-infrared Xanthene Dyesmentioning

confidence: 99%

Silicon-substituted xanthene dyes and their applications in bioimaging

Kushida

Nagano

Hanaoka

2015

Analyst

142

106

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Fluorescence imaging is one of the most powerful techniques for visualizing temporal and spatial changes of biological phenomena in living cells, and many fluorescent probes have been developed. In particular, xanthene dyes such as fluorescein and rhodamines have favorable characteristics, such as high water solubility, high fluorescence quantum yield and high molar extinction coefficient, and they have been utilized as fluorescent cores for fluorescent probes working in the green to red wavelength region. Recently, silicon-substituted xanthene dyes such as 2,7-N,N,N',N'-tetramethyl-9-dimethyl-10-hydro-9-silaanthracene (TMDHS), Si-rhodamines and TokyoMagentas, in which the O atom at the 10-position of xanthene is replaced with a Si atom, have been developed as novel far-red to near-infrared fluorescent cores that retain the key advantages of the parent structures. Fluorescent probes based on them have opened up new possibilities for imaging biological processes in living cells. This minireview covers recent progress in silicon-substituted xanthene dyes, including representative applications for in vivo tumor imaging, triple-color imaging of neuronal activity, and super-resolution microscopy.

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Section: Design Concept Of Far-red To Near-infrared Xanthene Dyesmentioning

confidence: 99%

Silicon-substituted xanthene dyes and their applications in bioimaging

Kushida

Nagano

Hanaoka

2015

Analyst

142

106

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“…Red fluorescent labels are particularly useful in life sciences, especially in biological fluorescence microscopy and single molecule spectroscopy (Fu et al 2008;Bruyneel et al 2010), because they require excitation photons of lower energy thus entailing less background due to autofluorescence. In addition, they are particularly attractive for stimulated emission depletion (STED) microscopy (Hell and Wichmann 1994;Klar et al 2000;Dyba et al 2003) because their fluorescence can be stopped with near-infrared wavelengths (typically > 750 nm) that are not only relatively benign to the sample, but also leave the visible spectrum open for the detection of other fluorophores.…”

Section: Introductionmentioning

confidence: 99%

Novel red fluorophores with superior performance in STED microscopy

et al. 2012

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In optical microscopy, most red-emitting dyes provide only moderate performance due to unspecific binding, poor labeling efficiency, and insufficient brightness. Here we report on four novel red fluororescent dyes, including the first phosphorylated dye, created by combining a rigidized rhodamine backbone with various polar groups. They exhibit large fluorescence quantum yields and improved NHS ester stability. While these fluorophores are highly suitable for fluorescence microscopy in general, they excel in stimulated emission depletion (STED) microscopy, providing < 25 nm spatial resolution in raw images of cells.

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“…Recently, Xiao, Nagano, and their respective co-workers (24,25) found that replacement of the oxygen atom in the xanthene moiety of tetramethylrhodamine with a silicon atom (Si-rhodamine) induces a dramatic red shift in emission of nearly 100 nm into the NIR region. Importantly, the fluorescence quantum yields of these probes could be modulated by over 100-fold through photoinduced electron transfer (PeT), rendering Sirhodamine a promising scaffold for sensor development (26)(27)(28).…”

mentioning

confidence: 99%

Imaging bacterial peptidoglycan with near-infrared fluorogenic azide probes

Shieh¹,

Siegrist²,

Cullen³

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

191

139

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Fluorescent probes designed for activation by bioorthogonal chemistry have enabled the visualization of biomolecules in living systems. Such activatable probes with near-infrared (NIR) emission would be ideal for in vivo imaging but have proven difficult to engineer. We present the development of NIR fluorogenic azide probes based on the Si-rhodamine scaffold that undergo a fluorescence enhancement of up to 48-fold upon reaction with terminal or strained alkynes. We used the probes for mammalian cell surface imaging and, in conjunction with a new class of cyclooctyne D-amino acids, for visualization of bacterial peptidoglycan without the need to wash away unreacted probe.

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A design concept of long-wavelength fluorescent analogs of rhodamine dyes: replacement of oxygen with silicon atom

Abstract: Replacement of the oxygen with a silicon atom on the rhodamine framework produces a strong red-emission fluorophore which has a high molar extinction coefficient and 90 nm red shift relative to rhodamine dye PY.

Cited by 259 publications

References 51 publications

Silicon-substituted xanthene dyes and their applications in bioimaging

Silicon-substituted xanthene dyes and their applications in bioimaging

Novel red fluorophores with superior performance in STED microscopy

Imaging bacterial peptidoglycan with near-infrared fluorogenic azide probes

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