Sugar response of boronic acid-substituted azobenzene dye-modified polymer

Egawa, Yuya; Gotoh, Ryota; Seki, Toshinobu; Anzai, Jun Ichi

doi:10.1016/j.msec.2008.05.014

Cited by 33 publications

(28 citation statements)

References 32 publications

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“…This strengthens the Lewis acid-Lewis base interaction within the receptor, resulting in PET from the amino nitrogen to the chromophoric center, thereby causing a change in color (Figure 4A) [2,31]. Since a shift in the absorbance of most azo-dyes is directly associated with changes in the environment of one of the bridging nitrogens, some sugar sensors have been designed that make use of a spectral change based on the formation and cleavage of the B—N bond between the boronic acid and the azo linkage (Figure 4B) [30,32•]. In other examples, the boronic acid group is directly attached to the chromophore, whose color changes upon chelation of the boronic acid group to a monosaccharide (see Figure 4C) [29].…”

Section: Colorimetric Sensors and Sensing Methodsmentioning

confidence: 99%

“…In many cases, phenylboronic acids are coupled with chromophores to give a color response to binding of the boronic acid moiety. In this manner, several color changing motifs have been utilized including, indicator displacement [26••,27-28•], boronic acid appended chromophores [24,29-32•], and pH induction [33,34••], and these have been extended to produce differential sensing platforms optimized to human body temperature and physiological pH [23,35-37]. …”

Section: Interactions Between Boronic Acids and Diolsmentioning

confidence: 99%

“…A) Photo-induced electron transfer (PET) method [31], B) B—N bond formation/cleavage method [32•], C) Boronic-acid chelating method [29], D) Macrocyclic ring opening method [44], and E) pH induced color change method [33]. Images used with permission.…”

Section: Figuresmentioning

confidence: 99%

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Differential sensing of sugars by colorimetric arrays

Musto

Suslick

2010

Current Opinion in Chemical Biology

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While the complexes between boronic acids and diols have been studied for decades, researchers continue to design new and interesting methods to use these interactions to produce saccharide sensors that are more sensitive and selective. Herein we discuss how the use of pattern-based colorimetric arrays from a collection of crossreactive sensors have been developed as new differential sensing platforms for sugars and related saccharides.

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Section: Colorimetric Sensors and Sensing Methodsmentioning

confidence: 99%

Section: Interactions Between Boronic Acids and Diolsmentioning

confidence: 99%

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Differential sensing of sugars by colorimetric arrays

Musto

Suslick

2010

Current Opinion in Chemical Biology

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“…[26][27][28] In addition, PBA-appended polymers show a relatively high selectivity for Glc compared to monomeric PBA derivatives. 29) In these systems, two PBA moieties cooperatively bind one Glc molecule. Multiple arrangements of the PBA moiety may be effective in increasing the Glc response of the LbL films, but modification with large moieties tend to decrease hypoglycemic activity.…”

Section: )mentioning

confidence: 99%

Sugar-Responsive Layer-by-Layer Film Composed of Phenylboronic Acid-Appended Insulin and Poly(vinyl alcohol)

Takei

Ohno

Seki

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Previous studies have shown that reversible chemical bond formation between phenylboronic acid (PBA) and 1,3-diol can be utilized as the driving force for the preparation of layer-by-layer (LbL) films. The LbL films composed of a PBA-appended polymer and poly(vinyl alcohol) (PVA) disintegrated in the presence of sugar. This type of LbL films has been recognized as a promising approach for sugar-responsive drug release systems, but an issue preventing the practical application of LbL films is combining them with insulin. In this report, we have proposed a solution for this issue by using PBA-appended insulin as a component of the LbL film. We prepared two kinds of PBA-appended insulin derivatives and confirmed that they retained their hypoglycemic activity. The LbL films composed of PBA-appended insulin and PVA were successfully prepared through reversible chemical bond formation between the boronic acid moiety and the 1,3-diol of PVA. The LbL film disintegrated upon treatment with sugars. Based on the results presented herein, we discuss the suitability of the PBA moiety with respect to hypoglycemic activity, binding ability, and selectivity for D-glucose.Key words layer-by-layer; phenylboronic acid; insulin; sugar response; smart materialThe layer-by-layer (LbL) deposition technique has attracted considerable interest for the preparation of nano-sized multilayer films on solid surfaces.1,2) The LbL deposition technique usually leverages the electrostatic interactions between oppositely charged molecules. This type of LbL films is stable on the solid support unless the pH of the surrounding solution is changed, which is advantageous for the construction of thin stable films. However, the good stability of the films, which need to be disintegrated for drug release, causes an issue for drug delivery applications.An LbL film that disintegrates upon exposure to specific stimuli is desirable for drug delivery systems, but requires a reversible driving force for LbL film.3) To meet this demand, the incorporation of phenylboronic acid (PBA) is a promising approach. [4][5][6][7][8][9][10] PBA derivatives show binding ability for the 1,2-diol, and 1,3-diol of sugars, which can result in the formation of a cyclic ester even in aqueous solution. 11,12) The cyclic ester formation is a reversible reaction, which is suitable for stimuli-responsive LbL films. For example, Anzai's group has prepared LbL films composed of a PBA-modified amine dendrimer and poly(vinyl alcohol) (PVA) through interaction between PBA and the 1,3-diol of PVA with great success. 7-9)This LbL film disintegrated when the film was immersed in sugar solutions, which is driven by the displacement of PVA by sugar on the PBA moiety.

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“…As a result, much attention has been paid to the development of saccharide sensors based on PBA and its derivatives as recognition components [1,2]. The artificial receptors by appending chromophores [3,4], fluorophores [5,6] and electro-active groups [7][8][9][10][11] covalently associated with PBA have been widely used for recognition and detection of saccharide and other biologically important agents (e.g., dopamine [12,13], sialic acid [14], NAD(P)+/NAD(P)H [15], glycoproteins [16,17], bacteria [18,19] and cell [20]). …”

Section: Introductionmentioning

confidence: 99%