Boronic Acid Fluorophore/β-Cyclodextrin Complex Sensors for Selective Sugar Recognition in Water

Tong, Aijun; Yamauchi, Akiyo; Hayashita, Takashi; Zhang, Zhiyi; Smith, Bradley D.; Teramae, Norio

doi:10.1021/ac001363k

Cited by 152 publications

(80 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, for simplicity, we used a conditional equilibrium of C1-APB with saccharide at the fixed CD concentration. As we reported earlier, 16 the conditional binding constant (KLS) at the fixed CD condition is expressed as…”

Section: Ph Dependence Of the Fluorescence Spectramentioning

confidence: 95%

“…The solid lines of Fig. 3c were obtained from the theoretical calculation, 16 and pKa values were determined by nonlinear curve-fitting. The pKa without D-fructose is 8.07, but the apparent pKa (pK a app ) with Dfructose is 6.01.…”

Section: Ph Dependence Of the Fluorescence Spectramentioning

confidence: 99%

“…16 Thereby, the effect of the concentration of seven kinds of saccharides was examined at pH 7.1 (Fig. 5).…”

Section: Selectivity Of C1-apb/β-cd For Saccharidesmentioning

confidence: 99%

“…1). 16 The β-CD solubilizes the water-insoluble C4-CPB by forming an inclusion complex. The fluorescence response of this complex is based on the PET mechanism.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Effect of Cyclodextrins on Saccharide Sensing Function of a Fluorescent Phenylboronic Acid in Water

et al. 2008

Self Cite

View full text Add to dashboard Cite

Sugars are essential biological molecules that play fundamental roles in metabolism and the maintenance of cell structure. They are also related to cell differentiation and immunity.1 Because of their important properties, researchers need simple methods that can quickly recognize sugars in aqueous solution. Enzymebased sensors are highly selective, but of limited use for continuous monitoring and in vivo analysis because of their poor stability and because they consume their substrate in the recognition process. Although chemosensors based on boronic acid are not as selective, they have attracted much attention because of their greater stability. 2,3 Phenylboronic acid can readily form stable cyclic esters with the diol moiety of sugars in water, 4 and various types of the boronic acid chemosensors with response mechanism based on internal charge transfer (ICT), 5-8 photoinduced electron transfer (PET), 9-11 and fluorescent resonance energy transfer (FRET) 12 have been developed. The versatile designs of chemosensors based on supramolecular chemistry are another approach to construct novel sugar sensors. [13][14][15] We reported that the complex consisting of the boronic acid fluorophore (C4-CPB) and β-cyclodextrin (β-CD) acts as a supramolecular saccharide sensor (Fig. 1). 16 The β-CD solubilizes the water-insoluble C4-CPB by forming an inclusion complex. The fluorescence response of this complex is based on the PET mechanism. The inherent fluorescence of C4-CPB is quenched by the internal PET from pyrene to the trigonal form of phenylboronic acid, but saccharide binding converts the boronic acid to the tetrahedral boronate, thereby inhibiting PET quenching and increasing the fluorescence intensity. In a previous study, the spacer effect of the boronic acid probe was examined in detail by using the fluorophores C1-CPB, C4-CPB, and C1-APB (Fig. 1). We found that the C1-APB/β-CD complex was a desirable fluorescent chemosensor for saccharide recognition because of its high affinity to saccharides as well as its relatively high fluorescence recovery upon saccharide binding. Since C1-APB is more soluble than C1-CPB and C4-CPB, because of possessing an amide group, it can be dissolved in water without adding β-CD at the level for the fluorescent measurement. This makes a precise comparison of the CD effect feasible. In the present work, therefore, we focused on C1-APB/CD complexes, and investigated how the sensing function of C1-APB for saccharide recognition in water was affected by differences in An inclusion complex consisting of a fluorescent phenylboronic acid (C1-APB) and β-cyclodextrin (β-CD) acts as a supramolecular saccharide sensor whose response mechanism is based on photoinduced electron transfer (PET). This study evaluated four kinds of cyclodextrins (α-CD, β-CD, γ-CD, and NH2-β-CD) by comparing their pH profiles, and confirmed that β-CD was the best host for C1-APB because the C1-APB/β-CD complex exhibited high affinity for saccharides as well as high fluorescent recovery upon saccharide binding. An ...

show abstract

Section: Ph Dependence Of the Fluorescence Spectramentioning

confidence: 95%

Section: Ph Dependence Of the Fluorescence Spectramentioning

confidence: 99%

“…16 Thereby, the effect of the concentration of seven kinds of saccharides was examined at pH 7.1 (Fig. 5).…”

Section: Selectivity Of C1-apb/β-cd For Saccharidesmentioning

confidence: 99%

“…1). 16 The β-CD solubilizes the water-insoluble C4-CPB by forming an inclusion complex. The fluorescence response of this complex is based on the PET mechanism.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Effect of Cyclodextrins on Saccharide Sensing Function of a Fluorescent Phenylboronic Acid in Water

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…It could be coupled with either a monosaccharide (glucose) or polysaccharide (Dextran) forming the respective boronate ester, where the luminescence intensities increased by up to 40-50%, when the concentration of carbohydrate unit in solution was at least 10 times higher than that of boronic acid. Their association constants with saccharides were estimated to be 3.3 × 10 3 and 4.9 × 10 3 M −1 based on the relation between the luminescence intensity and concentration of carbohydrate [24,25]. Figure 6-Bottom shows the luminescence spectra of silver nanoparticles capped with thiolated boronic acid groups (SNBA) before and after the addition of glucose at pH 5 in water.…”

Section: Preparation Of Thiolated Boronic Acid and Its Interactions Wmentioning

confidence: 99%

Saccharide Sensing Using Gold and Silver Nanoparticles-A Review

Aslan

Zhang

Lakowicz

et al. 2004

Journal of Fluorescence

133

View full text Add to dashboard Cite

We review new methodologies for glucose sensing from our laboratories based on the specific biological interactions between Con A, dextran-coated gold nanoparticles and glucose, and the interactions between dextran, glucose, and boronic-acid capped silver nanoparticles in solution. Our new approaches promise new tunable glucose sensing platforms. Dextran-coated gold nanoparticles were aggregated with the addition of Con A resulting in increase an in absorbance of nanoparticles at 650 nm, where the post-addition of glucose caused the dissociation of the aggregates and thus a decrease in the absorbance at 650 nm. The interaction of glucose and dextran with boronic acid-capped silver nanoparticles in solution resulted in enhanced luminescence intensity cumulatively due to surfaceenhanced fluorescence and the decrease in absorbance at 400 nm, with an increase in absorbance at 640 nm. Lifetime measurements were used to distinguish the contribution from the surface-enhanced fluorescence. TEM was employed to assess the aggregation of nanoparticles.

show abstract