A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution
Fluorescence sensing of saccharides and glycoproteins using a boronic acid functionalized squarylium cyanine dye (“<strong>SQ-BA</strong>”) is characterized in terms of synthetic, fluorometric, thermodynamic and kinetic parameters. In our previous work, this newly synthes...
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| Format: | Article |
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MDPI AG
2012-04-01
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| Series: | Sensors |
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| Online Access: | http://www.mdpi.com/1424-8220/12/5/5420 |
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| author | Hiroyuki Nakazumi Christa L. Colyer Takeshi Maeda Tara L. Massie Shingo Saito |
| author_facet | Hiroyuki Nakazumi Christa L. Colyer Takeshi Maeda Tara L. Massie Shingo Saito |
| author_sort | Hiroyuki Nakazumi |
| collection | DOAJ |
| description | Fluorescence sensing of saccharides and glycoproteins using a boronic acid functionalized squarylium cyanine dye (“<strong>SQ-BA</strong>”) is characterized in terms of synthetic, fluorometric, thermodynamic and kinetic parameters. In our previous work, this newly synthesized dye was successfully applied to the separation and quantification of Gram-positive bacteria by capillary electrophoresis with laser-induced fluorescence detection (CE-LIF); however, the fundamental properties of the dye and its saccharide complexes still required elucidation, as presented in this paper. The dye itself forms nonemissive, soluble aggregates in aqueous solution. With the addition of a monosaccharide, the dye aggregate dissociates to form an emissive monomer accompanied by the formation of a cyclic <em>cis</em>-diol ester with long-wavelength emission (<em>l</em><sub>ex</sub> = 630 nm, <em>l</em><sub>em</sub> = 660 nm). A very large fluorescence enhancement factor of 18× was observed for the sensing dye as a fructose complex at pH 10, yielding a limit of detection of 10 mM fructose. The relative order of fluorescence enhancement of SQ-BA with other monosaccharides was found to be: fructose > ribose > arabinose ≈ galactose > xylose > mannose > rhamnose > fucose ≈ glucose; and apparent affinity constants of 10<sup>2.80</sup>, 10<sup>2.08</sup> and 10<sup>0.86</sup> M<sup>−1</sup> were determined for fructose, ribose and glucose, respectively. Formation of the emissive complexes occurred within minutes, proving the kinetics of the sugar-dye interactions to be suitable for on-column labeling methods in CE-LIF. Furthermore, the sensing dye was successfully applied to glycoproteins, mucin type I–S and type III, which were detected with high sensitivity in batch aqueous solution as a result of the sugar-selective boronic acid-diol esterification as well as hydrophobic interactions. |
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| language | English |
| last_indexed | 2024-04-14T00:50:55Z |
| publishDate | 2012-04-01 |
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| series | Sensors |
| spelling | doaj.art-91061694cf01420e96be5880dd55b8e32022-12-22T02:21:49ZengMDPI AGSensors1424-82202012-04-011255420543110.3390/s120505420A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous SolutionHiroyuki NakazumiChrista L. ColyerTakeshi MaedaTara L. MassieShingo SaitoFluorescence sensing of saccharides and glycoproteins using a boronic acid functionalized squarylium cyanine dye (“<strong>SQ-BA</strong>”) is characterized in terms of synthetic, fluorometric, thermodynamic and kinetic parameters. In our previous work, this newly synthesized dye was successfully applied to the separation and quantification of Gram-positive bacteria by capillary electrophoresis with laser-induced fluorescence detection (CE-LIF); however, the fundamental properties of the dye and its saccharide complexes still required elucidation, as presented in this paper. The dye itself forms nonemissive, soluble aggregates in aqueous solution. With the addition of a monosaccharide, the dye aggregate dissociates to form an emissive monomer accompanied by the formation of a cyclic <em>cis</em>-diol ester with long-wavelength emission (<em>l</em><sub>ex</sub> = 630 nm, <em>l</em><sub>em</sub> = 660 nm). A very large fluorescence enhancement factor of 18× was observed for the sensing dye as a fructose complex at pH 10, yielding a limit of detection of 10 mM fructose. The relative order of fluorescence enhancement of SQ-BA with other monosaccharides was found to be: fructose > ribose > arabinose ≈ galactose > xylose > mannose > rhamnose > fucose ≈ glucose; and apparent affinity constants of 10<sup>2.80</sup>, 10<sup>2.08</sup> and 10<sup>0.86</sup> M<sup>−1</sup> were determined for fructose, ribose and glucose, respectively. Formation of the emissive complexes occurred within minutes, proving the kinetics of the sugar-dye interactions to be suitable for on-column labeling methods in CE-LIF. Furthermore, the sensing dye was successfully applied to glycoproteins, mucin type I–S and type III, which were detected with high sensitivity in batch aqueous solution as a result of the sugar-selective boronic acid-diol esterification as well as hydrophobic interactions.http://www.mdpi.com/1424-8220/12/5/5420squarylium dyeboronic acidmonosaccharideglycoproteinmucinlong wavelength fluorescence |
| spellingShingle | Hiroyuki Nakazumi Christa L. Colyer Takeshi Maeda Tara L. Massie Shingo Saito A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution Sensors squarylium dye boronic acid monosaccharide glycoprotein mucin long wavelength fluorescence |
| title | A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution |
| title_full | A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution |
| title_fullStr | A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution |
| title_full_unstemmed | A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution |
| title_short | A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution |
| title_sort | long wavelength fluorescent squarylium cyanine dye possessing boronic acid for sensing monosaccharides and glycoproteins with high enhancement in aqueous solution |
| topic | squarylium dye boronic acid monosaccharide glycoprotein mucin long wavelength fluorescence |
| url | http://www.mdpi.com/1424-8220/12/5/5420 |
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