215868-31-8Relevant academic research and scientific papers
Hydrolysis of 3-carboxy-6,8-difluoro-7-hydroxycoumarin (Pacific Blue) succinimidyl ester under acidic and basic conditions
Stockton, Amanda M.,Mora, Maria F.,Cable, Morgan L.,Willis, Peter A.,Davenport, Timothy C.,Tilley, T. Don
, p. 148 - 151,4 (2013)
The highly sensitive technique of microchip capillary electrophoresis (μCE) with laser-induced fluorescence (LIF) detection is under development for future in situ spaceflight missions to search for the organic chemical signatures of life. One fluorescent probe that enables this technology for amine, amino acid, and dipeptide analysis is 3-carboxy-6,8-difluoro-7- hydroxycoumarin (Pacific Blue, PB) succinimidyl ester. Of particular importance is the hydrolysis of PB succinimidyl ester, which precludes long-term aqueous storage during spaceflight and therefore has a significant impact on instrument design and operation. As such, it is important to characterize the chemical stability of this dye to hydrolysis prior to spaceflight. Here, we study the hydrolysis kinetics of the PB succinimidyl ester at pH values between 3 and 10.5 using μCE-LIF. The PB succinimidyl ester has the longest lifetime at pH 4 (7.3 ± 0.1 h), with dramatically shorter half-lives in the basic pH regime. This work represents a first step in the full characterization of this fluorescent probe for spaceflight applications.
A Practical Synthesis of 6,8-Difluoro-7-hydroxycoumarin Derivatives for Fluorescence Applications
Kerkovius, Jeff K.,Menard, Frederic
, p. 1622 - 1629 (2016/05/24)
A practical synthesis for 6,8-difluoro-7-hydroxycoumarin-3-carboxylic acid - one of the most widely used coumarin fluorescence imaging dye for bioconjugation - is reported. The synthesis was optimized for a preparative scale to obtain 14 g of the fluoresc
Derivatives of 6,8-difluoro-7-hydroxycoumarin
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, (2008/06/13)
The present invention comprises 6,8-difluoro-7-hydroxycoumarins and derivatives of 6,8-difluoro-7-hydroxycoumarins, including reactive dyes, dye-conjugates and enzyme substrates. These fluorine-substituted fluorescent dyes typically possess greater photostability and lower pH sensitivity in the physiological pH range than their nonfluorinated analogs, exhibit less fluorescence quenching when conjugated to a substance, possess absorption and emission spectra that closely match those of their nonfluorinated analogs, and also exhibit higher quantum yields than their nonfluorinated analogs.
Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes
Sun, Wei-Chuan,Gee, Kyle R.,Haugland, Richard P.
, p. 3107 - 3110 (2007/10/03)
Two new fluorinated fluorescent dyes, 6,8-difluoro-7-hydroxy-4- methylcoumarin (Marina Blue(TM)) and 3-carboxy-6,8-difluoro-7- hydroxycoumarin (Pacific Blue(TM)), exhibit excellent photophysical properties among a series of novel fluorinated 7-hydroxycoumarins. Most of these fluorinated coumarins have quantum yields (0.63 to 0.89) equal to or higher than that of the parent compound (0.63), which, in combination with their lower pK(a)S and higher photostability, make them superior fluorescent dyes for use as reporter molecules in biological systems.
