Charge transfer fluorescent probes using boronic acids for monosaccharide signaling

DiCesare, Nicholas; Lakowicz, Joseph R.

doi:10.1117/1.1502263

Cited by 34 publications

(62 citation statements)

References 38 publications

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“…5 -middle shows useful intensity changes in the presence of physiologically important glucose concentrations, where the blood glucose level is 3-8 mM for a healthy person and increases to between 2 and 40 mM in diabetics. 45 In the tear glucose range (µM glucose concentration range), Fig. 5 -bottom, we are able to see a ≈ 10-15% change in fluorescence intensity by the addition of 1 mM glucose, whereas fructose shows a much greater response in this concentration range.…”

Section: Resultsmentioning

confidence: 79%

Ophthalmic glucose sensing: a novel monosaccharide sensing disposable and colorless contact lens

Badugu

Lakowicz

Geddes

2004

Analyst

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We have developed a technology for continuous tear glucose monitoring, and therefore potentially blood glucose monitoring, using a daily use, disposable contact lens embedded with sugar-sensing boronic acid containing fluorophores. The novelty of our approach is two fold. Firstly, the notion of sensing extremely low glucose concentrations in tears by our approach, and secondly, the unique compatibility of our new probes with the internal environment of the disposable, off-theshelf, contact lenses, chosen because the physiological compatibility of disposable plastic contact lenses has already been assessed and optimized with regard to vision correction, size and oxygen / analyte permeability. Our findings show that our approach is indeed suitable for the continuous monitoring of tear glucose levels in the concentration range (50-500 µM), which track blood glucose levels which are ≈ 5-10 fold higher. We believe our approach offers unique opportunities for non-invasive continuous glucose monitoring for diabetics, especially since many have eye disorders and require vision correction by either contact lenses or glasses, which is thought to be due to glycation of protein in blood vessels. IntroductionContinuous monitoring of blood glucose is essential to avoid the long-term consequences of elevated blood glucose, including neuropathies, blindness and sequella.1 , 2 These adverse health effects have resulted in worldwide efforts to develop non-or minimally-invasive methods to monitor blood glucose. 3 -13 A wide variety of methods have been proposed, including near infrared spectroscopy, 3 , 4 optical rotation, 5 , 6 colorimetric 7 , 8 and fluorescence detection. 9 -13 The most commonly used technology for blood glucose determination is an enzyme based method, which requires frequent blood sampling and therefore drawing. Although frequent "finger pricking" with a small needle to obtain the blood sample is a relatively painless process, this method does suffer from a few practical problems. The firstCorrespondence to: Chris D. Geddes, cfs@cfs.umbi.umd.edu. HHS Public Access Author ManuscriptAuthor Manuscript Author ManuscriptAuthor Manuscript one is inconvenience and the required compliance by patients, which is often difficult for both the young and old, while the second is that this is not a continuous monitoring method. Despite intensive efforts, no method is presently available for the continuous non-invasive measurement of blood glucose.Elevated tear glucose during hyperglycemia was first demonstrated by Michail and coworkers in 1937, 14 , 15 as tear glucose levels track blood levels, in an analogous manner to the equilibrium that normally exists for glucose between blood and tissue fluid. 16 While it has been difficult to determine actual glucose concentrations in tears to-date, it is generally accepted that glucose levels are low and in the range 50-500 µM. 17 -21 For example, Giardini and Roberts have reported tear glucose concentrations to be ≈ 3 mg 100 ml −1 for subjects with a normal glucose met...

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Section: Resultsmentioning

confidence: 79%

Ophthalmic glucose sensing: a novel monosaccharide sensing disposable and colorless contact lens

Badugu

Lakowicz

Geddes

2004

Analyst

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“…The boronic acid content of PVBAc-g-MWNTs was 296 mg/g, as determined by titration. The diols are linked covalently and the reaction is fast and completely reversible (Cesare & Lakowicz, 2002b). The cyclic voltammograms of PVBAc-g-MWNTs in 0.1 M phosphoric buffer solution displayed an excellent linear response to glucose concentration in the range 1.0-10 mM.…”

Section: Chemical Reaction Between Boronic Acid Containing Group Modimentioning

confidence: 90%

Fabrication of biosensors using vinyl polymer-grafted carbon nanotubes

Chung¹,

Kwen²,

Choi³

2011

New Perspectives in Biosensors Technology and Applications

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“…Boronic acids couple with diols to form a boronic acid diester group (3 in scheme 1). The diol is linked covalently, and the reaction is fast and completely reversible [38]. In comparison to the boronic acid group, the boronic acid ester group shows higher acidity (pK a ≈ 6) due to a higher electrophilic boron atom.…”

Section: Ohmentioning

confidence: 99%

“…In comparison to the boronic acid group, the boronic acid ester group shows higher acidity (pK a ≈ 6) due to a higher electrophilic boron atom. The monophenylboronic acid group shows higher affinity for D-fructose with a smaller affinity for D-glucose [38], with binding constants of ≈ 0.5 and 10 mM respectively [38]. The use of the boronic acid groups for sensing sugars is strongly dependent on Scheme 1.…”

Section: Ohmentioning

confidence: 99%

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Ophthalmic Glucose Monitoring Using Disposable Contact Lenses—A Review

Badugu

Lakowicz

Geddes

2004

Journal of Fluorescence

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We have developed a range of disposable and colorless tear glucose sensing contact lenses, using offthe-shelf lenses embedded with new water soluble, highly fluorescent and glucose sensitive boronic acid containing fluorophores. The new lenses are readily able to track tear glucose levels and therefore blood glucose levels, which are ideally suited for potential use by diabetics. The fluorescence responses from the lenses can be monitored using simple excitation and emission detection devices. The novelty of our approach is two fold. Firstly, the notion of sensing extremely low glucose concentrations in tears, which track blood levels, by our contact lens approach, and secondly, the unique compatibility of our new glucose signaling probes with the internal mildly acidic contact lens environment. The new lenses are therefore ideal for the non-invasive and continuous monitoring of tear glucose, with about 15-min response time, and a measured shelf life in excess of 3 months. In this review article, we show that fluorescence based signaling using plastic disposable lenses, which have already been industrially optimized with regard to vision correction and oxygen/analyte permeability etc, may a notable alternative to invasive and random finger pricking, the most widely used glucose monitoring technology by diabetics.

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Charge transfer fluorescent probes using boronic acids for monosaccharide signaling

Cited by 34 publications

References 38 publications

Ophthalmic glucose sensing: a novel monosaccharide sensing disposable and colorless contact lens

Ophthalmic glucose sensing: a novel monosaccharide sensing disposable and colorless contact lens

Fabrication of biosensors using vinyl polymer-grafted carbon nanotubes

Ophthalmic Glucose Monitoring Using Disposable Contact Lenses—A Review

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