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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

Viologens, 10–13, developed and tested by Singaram and co-workers for the structural dependency on their quenching effect [48].
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biosensors-03-00400-f003: Viologens, 10–13, developed and tested by Singaram and co-workers for the structural dependency on their quenching effect [48].

Mentions: Recently, four quadrupole charged viologens, 10–13, were developed in order to elucidate how the structural features influenced their respective quenching abilities [48]. The structures of 10–13 are depicted in Figure 3. The quenching ability was found to increase in the order 11 < 12 < 13 < 10, which was ascribed to the decreasing tendency of pimer formation, caused by intramolecular stacking of the π-system in the viologens. In comparison to former published work [46], 10–13 are superior quenchers. This study indicates that the presence of the bisviologen core plays a greater part in the quenching rather than the charges. The highest d-glucose modulation was achieved with 13. This was ascribed to a higher degree of negative charge in comparison to 10–12. 10 and 12 were found to be far better quenchers than 11. This phenomenon may be attributed to their poorer ability to form pimers. The highest quenching constant was obtained with 10, followed by 13, with K = 6.8 × 105 M−1 and K = 4.4 × 105 M−1, respectively.


Recent advances in fluorescent arylboronic acids for glucose sensing.

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

Viologens, 10–13, developed and tested by Singaram and co-workers for the structural dependency on their quenching effect [48].
© Copyright Policy - open-access
Related In: Results  -  Collection

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

biosensors-03-00400-f003: Viologens, 10–13, developed and tested by Singaram and co-workers for the structural dependency on their quenching effect [48].
Mentions: Recently, four quadrupole charged viologens, 10–13, were developed in order to elucidate how the structural features influenced their respective quenching abilities [48]. The structures of 10–13 are depicted in Figure 3. The quenching ability was found to increase in the order 11 < 12 < 13 < 10, which was ascribed to the decreasing tendency of pimer formation, caused by intramolecular stacking of the π-system in the viologens. In comparison to former published work [46], 10–13 are superior quenchers. This study indicates that the presence of the bisviologen core plays a greater part in the quenching rather than the charges. The highest d-glucose modulation was achieved with 13. This was ascribed to a higher degree of negative charge in comparison to 10–12. 10 and 12 were found to be far better quenchers than 11. This phenomenon may be attributed to their poorer ability to form pimers. The highest quenching constant was obtained with 10, followed by 13, with K = 6.8 × 105 M−1 and K = 4.4 × 105 M−1, respectively.

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