Synthesis and Photophysics of a New Family of Fluorescent 9‐Alkyl‐Substituted Xanthenones

Martínez-Peragón, Ángela; Miguel, Delia; Jurado, Rocío; Justicia, José; Álvarez‐Pez, José M.; Cuerva, Juan M.; Crovetto, Luis

doi:10.1002/chem.201303113

Cited by 17 publications

(10 citation statements)

References 31 publications

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“…Recently, 9-alkyl xanthenones with different aliphatic pendant groups have been easily prepared, and their photophysical behaviour has also been explored. 28 Remarkably, some of them retained similar fluorescence properties to those of fluorescein, including the characteristic phosphatemediated ESPT reaction and higher pK a values (6.20-6.67) compared with TGs (5.97-6.04). 21,22 Nevertheless, this approach to increase the pK a without modifying the spectroscopic properties of the dye is limited by the electron donating nature of alkyl substituents.…”

Section: Introductionmentioning

confidence: 92%

Rational design of a new fluorescent ‘ON/OFF’ xanthene dye for phosphate detection in live cells

et al. 2014

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A new fluorescein derivative with ON/OFF features, 9-[1-(4-tert-butyl-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one (Granada Green, GG), was designed and synthesised. The new dye has spectral characteristics similar to those of other xanthenic derivatives but shows a higher pK(a) value for the equilibrium between its neutral and anionic forms. In addition, GG undergoes the same phosphate-mediated excited state proton transfer (ESPT) reaction as other xanthenic derivatives, giving rise to fluorescence decay traces that are dependent on both the phosphate concentration and pH of the medium. The phosphate-mediated ESPT reaction was employed to detect changes in the phosphate concentrations in live, permeabilised MC3T3-E1 preosteoblasts at pH 7.35. Its high pK(a) value indicates that this new dye is more sensitive as an intracellular phosphate sensor than other previously tested dyes, as experimentally demonstrated by its ability to detect a wider range of phosphate concentrations in biomimetic media and by the increased ratio of the phosphate concentration/decay time.

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Section: Introductionmentioning

confidence: 92%

Rational design of a new fluorescent ‘ON/OFF’ xanthene dye for phosphate detection in live cells

et al. 2014

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“…1b and c), because this benzene moiety is needed to control the uorescence properties of the probes and to provide a site for introducing reactive groups for labeling, as well as it generally contributes to the stability of the dye with respect to ambient nucleophiles via steric hindrance, similarly to xanthene dyes equipped with a bulky alkyl group. 24 The development of silicon-substituted rhodamine and uorescein analogues is discussed below.…”

Section: Development Of Silicon-substituted Rhodamine Analoguesmentioning

confidence: 99%

Silicon-substituted xanthene dyes and their applications in bioimaging

Kushida

Nagano

Hanaoka

2015

Analyst

140

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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“…In recent years, fluorescein‐based compounds have evolved to yield simple structures that can retain their striking photophysical properties. Thus, for example, some aryl‐5 and alkyl‐substituted xanthenones6 have simplified the original prototropic equilibrium in fluorescein, thereby improving the analysis of the photophysical data (Figure 1). Therefore, these molecules have been used as fluorescent probes for many biologically relevant analytes, such as β‐galactosidase,5, 7 hydrogen peroxide,8 nucleotide pyrophosphatases/phosphodiesterases,9 uridine diphosphate glucuronosyltransferase (UDPGT),10 and BlaC hydrolase of Mycobacterium tuberculosis 11 as well as in Western blot analysis 12.…”

Section: Introductionmentioning

confidence: 99%

New Dual Fluorescent Probe for Simultaneous Biothiol and Phosphate Bioimaging

Resa

Orte

Miguel

et al. 2015

Chemistry A European J

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The simultaneous detection of relevant metabolites in living organisms by using one molecule introduces an approach to understanding the relationships between these metabolites in healthy and deregulated cells. Fluorescent probes of low toxicity are remarkable tools for this type of analysis of biological systems in vivo. As a proof of concept, different naturally occurring compounds, such as biothiols and phosphate anions, were the focus for this work. The 2,4-dinitrobenzenesulfinate (DNBS) derivative of 9-[1-(4-tert-butyl-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one (Granada Green; GG) were designed and synthesized. This new sulfinyl xanthene derivative can act as a dual sensor for the aforementioned analytes simultaneously. The mechanism of action of this derivative implies thiolysis of the sulfinyl group of the weakly fluorescent DNBS-GG by biological thiols at near-neutral pH values, thus releasing the fluorescent GG moiety, which simultaneously responds to phosphate anions through its fluorescence-decay time. The new dual probe was tested in solution by using steady-state and time-resolved fluorescence and intracellularly by using fluorescence-lifetime imaging microscopy (FLIM) in human epithelioid cervix carcinoma (HeLa) cells.

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Synthesis and Photophysics of a New Family of Fluorescent 9‐Alkyl‐Substituted Xanthenones

Cited by 17 publications

References 31 publications

Rational design of a new fluorescent ‘ON/OFF’ xanthene dye for phosphate detection in live cells

Rational design of a new fluorescent ‘ON/OFF’ xanthene dye for phosphate detection in live cells

Silicon-substituted xanthene dyes and their applications in bioimaging

New Dual Fluorescent Probe for Simultaneous Biothiol and Phosphate Bioimaging

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