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Recent advances in fluorescent arylboronic acids for glucose sensing.

Hansen JS, Christensen JB - Biosensors (Basel) (2013)

Bottom Line: The long-term consequences of high blood glucose levels include damage to the heart, eyes, kidneys, nerves and other organs, among others, caused by malign glycation of vital protein structures.Fluorescent monitors based on arylboronic acids are promising candidates for optical CGM, since arylboronic acids are capable of forming arylboronate esters with 1,2-cis-diols or 1,3-diols fast and reversibly, even in aqueous solution.The recent progress in the development of fluorescent arylboronic acid dyes will be emphasized in this review.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg C, Copenhagen, Denmark. jonhansen@chem.ku.dk.

ABSTRACT
Continuous glucose monitoring (CGM) is crucial in order to avoid complications caused by change in blood glucose for patients suffering from diabetes mellitus. The long-term consequences of high blood glucose levels include damage to the heart, eyes, kidneys, nerves and other organs, among others, caused by malign glycation of vital protein structures. Fluorescent monitors based on arylboronic acids are promising candidates for optical CGM, since arylboronic acids are capable of forming arylboronate esters with 1,2-cis-diols or 1,3-diols fast and reversibly, even in aqueous solution. These properties enable arylboronic acid dyes to provide immediate information of glucose concentrations. Thus, the replacement of the commonly applied semi-invasive and non-invasive techniques relying on glucose binding proteins, such as concanavalin A, or enzymes, such as glucose oxidase, glucose dehydrogenase and hexokinases/glucokinases, might be possible. The recent progress in the development of fluorescent arylboronic acid dyes will be emphasized in this review.

No MeSH data available.


Related in: MedlinePlus

The near-infrared squarylium cyanine boronic acid dye, 20, reported by Saito and co-workers [58], and the two enantiomeric α-amidoboronic acids, 21 and 22, reported by Wang and co-workers [59].
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biosensors-03-00400-f005: The near-infrared squarylium cyanine boronic acid dye, 20, reported by Saito and co-workers [58], and the two enantiomeric α-amidoboronic acids, 21 and 22, reported by Wang and co-workers [59].

Mentions: Saito et al. reported a water soluble long-wavelength squarylium cyanine boronic acid dye, 20, for the detection of monosaccharides [58]. This dye was found to exhibit superior d-fructose binding selectivity in comparison to other tested monosaccharides. The studies were conducted in an aqueous carbonate buffer at pH 10, with λex = 630 nm and λem = 660 nm. An enhancement factor of 18 for the emission intensity was obtained in the presence of 20 mM d-fructose. The association constants for the binding of d-fructose and d-glucose was K = 628 M−1 and K = 8 M−1, respectively. This dye could be suitable for d-glucose monitoring through skin, due to the long wavelength of excitation and emission. The d-glucose selectivity must, however, be enhanced significantly and the d-glucose binding strength modulated towards physiological d-glucose levels. The reported dye, 20, is shown in Figure 5.


Recent advances in fluorescent arylboronic acids for glucose sensing.

Hansen JS, Christensen JB - Biosensors (Basel) (2013)

The near-infrared squarylium cyanine boronic acid dye, 20, reported by Saito and co-workers [58], and the two enantiomeric α-amidoboronic acids, 21 and 22, reported by Wang and co-workers [59].
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4263566&req=5

biosensors-03-00400-f005: The near-infrared squarylium cyanine boronic acid dye, 20, reported by Saito and co-workers [58], and the two enantiomeric α-amidoboronic acids, 21 and 22, reported by Wang and co-workers [59].
Mentions: Saito et al. reported a water soluble long-wavelength squarylium cyanine boronic acid dye, 20, for the detection of monosaccharides [58]. This dye was found to exhibit superior d-fructose binding selectivity in comparison to other tested monosaccharides. The studies were conducted in an aqueous carbonate buffer at pH 10, with λex = 630 nm and λem = 660 nm. An enhancement factor of 18 for the emission intensity was obtained in the presence of 20 mM d-fructose. The association constants for the binding of d-fructose and d-glucose was K = 628 M−1 and K = 8 M−1, respectively. This dye could be suitable for d-glucose monitoring through skin, due to the long wavelength of excitation and emission. The d-glucose selectivity must, however, be enhanced significantly and the d-glucose binding strength modulated towards physiological d-glucose levels. The reported dye, 20, is shown in Figure 5.

Bottom Line: The long-term consequences of high blood glucose levels include damage to the heart, eyes, kidneys, nerves and other organs, among others, caused by malign glycation of vital protein structures.Fluorescent monitors based on arylboronic acids are promising candidates for optical CGM, since arylboronic acids are capable of forming arylboronate esters with 1,2-cis-diols or 1,3-diols fast and reversibly, even in aqueous solution.The recent progress in the development of fluorescent arylboronic acid dyes will be emphasized in this review.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg C, Copenhagen, Denmark. jonhansen@chem.ku.dk.

ABSTRACT
Continuous glucose monitoring (CGM) is crucial in order to avoid complications caused by change in blood glucose for patients suffering from diabetes mellitus. The long-term consequences of high blood glucose levels include damage to the heart, eyes, kidneys, nerves and other organs, among others, caused by malign glycation of vital protein structures. Fluorescent monitors based on arylboronic acids are promising candidates for optical CGM, since arylboronic acids are capable of forming arylboronate esters with 1,2-cis-diols or 1,3-diols fast and reversibly, even in aqueous solution. These properties enable arylboronic acid dyes to provide immediate information of glucose concentrations. Thus, the replacement of the commonly applied semi-invasive and non-invasive techniques relying on glucose binding proteins, such as concanavalin A, or enzymes, such as glucose oxidase, glucose dehydrogenase and hexokinases/glucokinases, might be possible. The recent progress in the development of fluorescent arylboronic acid dyes will be emphasized in this review.

No MeSH data available.


Related in: MedlinePlus