Glucose with phenylboronic acid

Zenkl et al. [51] presented another approach to design saccharide-sensitive nanobeads. They prepared particles (0 380 nm) based on poly (/V- i sopropy I aery I am ide) cross-linked with phenylboronic acid moieties. In the presence of a saccharide (glucose or fructose) the particles reversibly swell due to the formation of negative charges. A FRET-indicator couple (fhiorescein/rhodamine) is used to monitor the... 

In another approach, insulin was modified to introduce hydroxyl groups so that the hydroxylated insulin can be immobilized by forming a complex with phenylboronic acid groups on the support (Fig. 16.11). The support can be hydrogel beads made of polymers containing phenylboronic acid, e.g. poly(m-methacrylamidophenylboronic acid). The hydroxylated insulin can be displaced by the added glucose and the displaced insulin can be released. 

Maekawa er al. reported that a series of co-oxazolylalkanoic acid derivatives as antidiabetic agents, promoting the glucose-dependent secretion of insulin. (o-(5-Oxazolyl)alka-noates 27, the key intermediates for the synthesis of target compounds, were prepared via Suzuki coupling of substituted 2-chlorooxazole with phenylboronic acid [34]. 

FIGURE 10.2 Temperature dependence of swelling curves for PNIPAAm copolymer hydrogel with phenylboronic acid moieties at different glucose concentrations. Reproduced from Ref. [32] with permission. Cop5uight 1998 American Chemical Society. 

Kitano S, Kataoka K, Koyama Y et al (1991) Glucose-responsive complex formation between poly (vinyl alcohol) and poly(lV-vinyl-2-pyrrolidone) with pendent phenylboronic acid moieties. Makromol Chem Rapid Commun 12 227-233... 

Kikuchi A, Suzuki K, Okabayashi O et al (1996) Glucose-sensing electrode coated with polymer complex gel containing phenylboronic acid. Anal Chem 68 823-828... 

Kitano, S., Koyama, Y., Kataoka, K., et al. A novel drug delivery system utilizing a glucose responsive polymer complex between poly (vinyl alcohol) and poly( V-vinyl-2-pyrrolidone) with a phenylboronic acid moiety. J. Contr. Rel. 19 161—170, 1992. 

Glucose-6-phosphate dehydrogenase NADP+ Sepharose 6B with 3-amino-phenylboronic acid 45... 

Figure 13 Schematic illustration of glucose-responsive insulin release from phenylboronic acid containing hydrogels cross-linked with polyCvinyl alcohol).

Shiino D, Kubo A, Murata Y, Koyama Y, Kataoka K, Kikuchi A, Sakurai Y, Okano T. Amine effect on phenylboronic acid complex with glucose under physiological pH in aqueous solution. J Biomater Sci Polym Ed 1996 7(8) 697-705. 

An electrochemical method involving electrocatalytic oxidation with TEMPO was suitable for the determination of glucose in aqueous solution. The cyanine dye 2, which carries two phenylboronic acid moieties displays increased fluorescence on binding to monosaccharides and provides a novel detection method. Compound 3 also contains a phenylboronic acid residue and binds D-glucose 6-... 

Figure 11.3 Reactive DESI. (a) Reaction of phenylboronic acid with cis-diols. n = 1 or 2. Reactive-DESI mass spectra showing the ionic species generated from PhB(OH) anions upon interaction with (bj a blank surface, (c) D-fructose on the surface, and (d) D-glucose absorbed in a cotton tip [44], Reproduced from Chen, H., Cotte-Rodrfguez, I., Cooks, R.C. (2006) with permission of the Royal Society of Chemistry...

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