pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination

Best, Quinn A.; Sattenapally, Narsimha; Dyer, Daniel J.; Scott, Colleen N.; McCarroll, Matthew E.

doi:10.1021/ja401426s

Cited by 163 publications

(75 citation statements)

References 20 publications

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“…In addition, NIR dyes that are being modified to serve as HOCl probes will enable relatively deep tissue penetration and minimal auto-fluorescence background. 2,4,5,30,51,57,66 …”

Section: Discussionmentioning

confidence: 99%

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Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Yue

Huo

Yin

et al. 2016

Analyst

165

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Due to the biological and industrial importance of hypochlorous acid, the development of optical probes for HOCl has been an active research area. Hypochlorous acid and hypochlorite can oxidize electron-rich analytes with accompanying changes in molecular sensor spectroscopic profiles. Probes for such processes may monitor HOCl levels in the environment or in an organism and via bio-labeling or bioimaging techniques. This review summarizes recent developments in the area of chromogenic and fluorogenic chemosensors for HOCl.

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“…In addition, NIR dyes that are being modified to serve as HOCl probes will enable relatively deep tissue penetration and minimal auto-fluorescence background. 2,4,5,30,51,57,66 …”

Section: Discussionmentioning

confidence: 99%

“…34). 51 Through the specific oxidation reaction of 35 and 1 equiv. HOCl, two open-form Si-fluorescein analogues 35 - I and 35 - II were produced.…”

Section: Thioether To Sulfonate and Selenide To Selenoxidementioning

confidence: 99%

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Yue

Huo

Yin

et al. 2016

Analyst

165

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“…However, although fluorescein has a carboxylic group at the 2-position of the benzene moiety, only TM derivatives with a methyl group or a spirothiophene at the 2 position of the benzene moiety have been reported so far. [31][32][33] Here, we describe the synthesis of 2-COOH TM, which has a carboxylic group at the 2-position of the benzene moiety ( Figure 1a). We found it exhibits a unique prototropic equilibrium that is suitable for the development of red-florescent probes.…”

mentioning

confidence: 99%

Analysis of Chemical Equilibrium of Silicon-Substituted Fluorescein and Its Application to Develop a Scaffold for Red Fluorescent Probes

Hirabayashi¹,

Hanaoka²,

Takayanagi

et al. 2015

Anal. Chem.

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Fluorescein is a representative green fluorophore that has been widely used as a scaffold of practically useful green fluorescent probes. Here, we report synthesis and characterization of a silicon-substituted fluorescein, i.e., 2-COOH TokyoMagenta (2-COOH TM), which is a fluorescein analogue in which the O atom at the 10' position of the xanthene moiety of fluorescein is replaced with a Si atom. This fluorescein analogue forms a spirolactone ring via intramolecular nucleophilic attack of the carboxylic group in a pH-dependent manner. Consequently, 2-COOH TM exhibits characteristic large pH-dependent absorption and fluorescence spectral changes: (1) 2-COOH TM is colorless at acidic pH, whereas fluorescein retains observable absorption and fluorescence even at acidic pH, and the absorption maximum is also shifted; (2) the absorption spectral change occurs above pH 7.0 for 2-COOH TM and below pH 7.0 for fluorescein; (3) 2-COOH TM shows a much sharper pH response than fluorescein because of its pKa inversion, i.e., pKa1 > pKa2. These features are also different from those of a compound without the carboxylic group, 2-Me TokyoMagenta (2-Me TM). Analysis of the chemical equilibrium between pH 3.0 and 11.0 disclosed that 2-COOH TM favors the colorless and nonfluorescent lactone form, compared with fluorescein. Substitution of Cl atoms at the 4' and 5' positions of the xanthene moiety of 2-COOH TM to obtain 2-COOH DCTM shifted the equilibrium so that the new derivative exists predominantly in the strongly fluorescent open form at physiological pH (pH 7.4). To demonstrate the practical utility of 2-COOH DCTM as a novel scaffold for red fluorescent probes, we employed it to develop a probe for β-galactosidase.

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“…Apparatus and chemicals 1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectra were acquired on a Bruker Avance spectrometer, with d 6 -DMSO used as a solvent and tetramethylsilane (TMS) as an internal standard. High-resolution mass spectroscopy (HRMS) was collected on a Q-TOF6510 spectrograph (Agilent).…”

Section: Methodsmentioning

confidence: 99%

“…Probe IRP was synthesized via a simple process (Scheme 1) and characterized by 1 H NMR, 13 C NMR and HRMS (Fig. S1-S3, ESI †).…”

Section: Design and Synthesis Of Probe Irpmentioning

confidence: 99%

A mitochondria-targeting ratiometric fluorescent probe for the detection of hypochlorite based on the FRET strategy

Shen

Zhang²,

et al. 2017

RSC Adv.

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pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination

Cited by 163 publications

References 20 publications

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Analysis of Chemical Equilibrium of Silicon-Substituted Fluorescein and Its Application to Develop a Scaffold for Red Fluorescent Probes

A mitochondria-targeting ratiometric fluorescent probe for the detection of hypochlorite based on the FRET strategy

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