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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.


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The chiral binol sensor, 1, developed by James and co-workers [36].
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biosensors-03-00400-f001: The chiral binol sensor, 1, developed by James and co-workers [36].

Mentions: The employed fluorescent dyes were based on anthracene [29,30], pyrene [31,32,33] and chiral binaphthols [34,35,36] coupled with diboronic acids to obtain superior d-glucose selectivity. Recent studies showed that the binol sensor was exhibiting a significant enantioselectivity for the binding of d-glucose at pH 6 (KR/KS = 1.4:1) [36]. KR is 2.01 × 102 M−1, while KS = 1.46 × 102 M−1. Chiral discrimination was, however, not exhibited at pH 8, since d-glucose was bound with a similar strength by sensor S1 and R1. KR is 2.42 × 102 M−1, while KS = 2.32 × 102 M−1 at pH 8. The λex is 305 nm, and the λem is 374 nm. The binol sensor, 1, is shown in Figure 1. The sensor, however, showed significantly higher binding affinity and chiral discrimination to important sugar alcohols, such as d-sorbitol, d-mannitol and xylitol. For d-sorbitol, KR/KS = 1.09/5.88 at pH 6, and KR/KS = 0.1 at pH 8. KR is 1.09 × 103 M−1, and KS is 5.88 × 103 M−1 at pH 6.0, while KR is 1.13 × 103 M−1 and 1.13 × 104 M−1 at pH 8.0. All measurements were carried out in 52.1 w/w% methanol in water NaCl ionic buffer, due to the poor aqueous solubility of the binol sensor.


Recent advances in fluorescent arylboronic acids for glucose sensing.

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

The chiral binol sensor, 1, developed by James and co-workers [36].
© Copyright Policy - open-access
Related In: Results  -  Collection

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

biosensors-03-00400-f001: The chiral binol sensor, 1, developed by James and co-workers [36].
Mentions: The employed fluorescent dyes were based on anthracene [29,30], pyrene [31,32,33] and chiral binaphthols [34,35,36] coupled with diboronic acids to obtain superior d-glucose selectivity. Recent studies showed that the binol sensor was exhibiting a significant enantioselectivity for the binding of d-glucose at pH 6 (KR/KS = 1.4:1) [36]. KR is 2.01 × 102 M−1, while KS = 1.46 × 102 M−1. Chiral discrimination was, however, not exhibited at pH 8, since d-glucose was bound with a similar strength by sensor S1 and R1. KR is 2.42 × 102 M−1, while KS = 2.32 × 102 M−1 at pH 8. The λex is 305 nm, and the λem is 374 nm. The binol sensor, 1, is shown in Figure 1. The sensor, however, showed significantly higher binding affinity and chiral discrimination to important sugar alcohols, such as d-sorbitol, d-mannitol and xylitol. For d-sorbitol, KR/KS = 1.09/5.88 at pH 6, and KR/KS = 0.1 at pH 8. KR is 1.09 × 103 M−1, and KS is 5.88 × 103 M−1 at pH 6.0, while KR is 1.13 × 103 M−1 and 1.13 × 104 M−1 at pH 8.0. All measurements were carried out in 52.1 w/w% methanol in water NaCl ionic buffer, due to the poor aqueous solubility of the binol sensor.

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