Development of Smart Contact Lenses for Ophthalmic Glucose Monitoring

Badugu, Ramachandram; Lakowicz, Joseph R.; Geddes, Chris D.

doi:10.1007/0-387-33015-1_17

Cited by 6 publications

(13 citation statements)

References 48 publications

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“…The preparation of the ortho, meta and para forms of BMQBA, BMO-QBA and the control compounds BMQ and BMOQ, Fig. 1, have recently been reported by us [19,20]. The response of our new probes is based on the ability of the boronic acid group to interact with the uncomplexed CN − anion, displacing the hydroxyl ion, changing from the neutral form of the boronic acid to the anionic R-B − (CN) 3 form, Scheme 1, which in turn interacts with an electron deficient (positively charged) quaternary heterocyclic nitrogen center.…”

Section: Methodsmentioning

confidence: 85%

Fluorescence intensity and lifetime-based cyanide sensitive probes for physiological safeguard

Badugu

Lakowicz

Geddes

2004

Analytica Chimica Acta

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We characterize six new fluorescent probes that show both intensity and lifetime changes in the presence of free uncomplexed aqueous cyanide, allowing for fluorescence based cyanide sensing up to physiological safeguard levels, i.e. <30 µM. One of the probes, m-BMQBA, shows a ≈15fold reduction in intensity and a ≈10% change in mean lifetime at this level.The response of the new probes is based on their ability to bind the cyanide anion through a boronic acid functional group, changing from the neutral form of the boronic acid group R-B(OH) 2 to the anionic R-B − (CN) 3 form, a new cyanide binding mechanism which we have recently reported. The presence of an electron deficient quaternary heterocyclic nitrogen nucleus, and the electron rich cyanide bound form, provides for the intensity changes observed. We have determined the disassociation constants of the probes to be in the range ≈ 15-84 µM 3 . In addition we have synthesized control compounds which do not contain the boronic acid moiety, allowing for a rationale of the cyanide responses between the probe isomers to be made.The lifetime of the cyanide bound probes are significantly shorter than the free R-B(OH) 2 probe forms, providing for the opportunity of lifetime based cyanide sensing up to physiologically lethal levels.Finally, while fluorescent probes containing the boronic acid moiety have earned a well-deserved reputation for monosaccharide sensing, we show that strong bases such as CN − and OH − preferentially bind as compared to glucose, enabling the potential use of these probes for cyanide safeguard and determination in physiological fluids, especially given that physiologies do not experience any notable changes in pH.

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Section: Methodsmentioning

confidence: 85%

Fluorescence intensity and lifetime-based cyanide sensitive probes for physiological safeguard

Badugu

Lakowicz

Geddes

2004

Analytica Chimica Acta

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“…These compounds easily bind with diols like sugars through reversible covalent interactions at physiological pH and have been widely used as a fluorescent probe in sensing and biological imaging of carbohydrates. Fluorophores tied with boronic acids for molecular detection are exclusively found with anthracene, naphthalene, naphthalimide, indol, quinolinium, benzo‐thiophene and fluorine moieties, which have been reported to quantify sugars and sugar derivatives in an aqueous media. In the view of the vast applications of boronic acids in biosensing and bioimaging of biomolecules, synthesis and characterizing new boronic acids via theoretical and experimental investigations is highly encouraging to unravel the physical and chemical properties.…”

Section: Introductionmentioning

confidence: 84%

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

et al. 2020

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Structure, Hirshfeld surface, spectra and photophysical properties of boronic acid‐based carbohydrate sensor (5‐fluoro‐2‐methoxyphenyl) boronic acid (BA8) has been reported by experimental methods (XRD/FT‐IR/UV/steady state fluorescence) and theoretically by Density functional theory (DFT) model with most accurate functionals (B3LYP/CAM−B3LYP/ M06‐2X). The comparison of theoretical and experimental data exhibited good agreement. Natural bond orbital (NBO) and frontier molecular orbitals (FMOs) have been analysed. The sensing ability of the compound with carbohydrates (D‐glucose and D‐fructose) were studied by UV/fluorescence spectra. The variation of absorbance and fluorescence on pH was rationale with the estimated acid‐base dissociation constants (pKa). Quantum yield (Φ) and fluorescence lifetimes (τ) for the compound and its esters with sugars were calculated. The results of absorbance, fluorescence measurements and calculated photophysical properties indicated fairly selectivity of BA8 with fructose more than the glucose, which is ascertained from both experimental and theoretical results.

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“…-OCH 3 , CH 3 , etc., in essence making the nitrogen center relatively more electron-deficient, then the dual emission bands at 450 and ≈546 nm are lost for a single emission band at ≈450 nm, eliminating the possibility of a ratiometric response. In contrast, a greater electron-deficient nitrogen center provides for a higher affinity for monosaccharides [32] (data not shown). Hence, our unique choice of backbone substituents affords for a high fluoride affinity with relatively little sugar response, even in the case of fructose, which is well known to have a high boronic acid affinity [19][20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 94%

A wavelength?ratiometric fluoride-sensitive probe based on the quinolinium nucleus and boronic acid moiety

Badugu

Lakowicz

Geddes

2005

Sensors and Actuators B: Chemical

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We report a new water-soluble fluorescent probe sensitive to aqueous fluoride. The probe shows spectral shifts and intensity changes in the presence of fluoride, in a wavelength ratiometric and colorimetric manner, enabling the detection of fluoride concentrations at visible wavelengths, in the concentration range ≈1-300 mM. The probes response is based on the ability of the boronic acid group to interact with fluoride, changing from the neutral form of the boronic acid group [R-B(OH) 2 ] to the anionic trifluoro form [R-B-F 3 ], which is an electron donating group. The presence of an electron-deficient quaternary heterocyclic nitrogen center and a strong electron donating amino group in the 6position, on the quinolinium backbone, provides for the spectral responses observed upon fluoride binding to the boronic acid group. Interestingly, the presence of the amino group on the 6-position of the quinolinium backbone suppresses the response of the boronic acid containing fluorophore towards monosaccharides, such as glucose and fructose, which are present in biological fluids and food stuffs, potentially allowing for the predominant fluoride sensitivity. In addition to physiological sugars, we discuss the response of aqueous halides as potential interferents, or indeed analytes to be sensed, and show that the new probe responds well to aqueous fluoride in the presence of a high background of other species, such as in a biological cocktail of 50 mM glucose, 50 mM aqueous Cl − and 5 mM fructose.

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Development of Smart Contact Lenses for Ophthalmic Glucose Monitoring

Cited by 6 publications

References 48 publications

Fluorescence intensity and lifetime-based cyanide sensitive probes for physiological safeguard

Fluorescence intensity and lifetime-based cyanide sensitive probes for physiological safeguard

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

A wavelength?ratiometric fluoride-sensitive probe based on the quinolinium nucleus and boronic acid moiety

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