Redox- and glucose-responsive hydrogels from poly(vinyl alcohol) and 4-mercaptophenylboronic acid

Nurpeissova, Zhansaya A.; Alimkhanova, Sholpan G.; Mangazbayeva, R.А.; Shaikhutdinov, Yerengaip M.; Mun, Grigoriy A.; Khutoryanskiy, Vitaliy V.

doi:10.1016/j.eurpolymj.2015.06.003

Cited by 19 publications

(4 citation statements)

References 31 publications

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“…When choosing a polymer platform for the preparation of hydrogels, the hydrophilicity is an important property to allow the uptake of water. A wide range of hydrophilic polymers are available including biopolymers, like alginate, − chitosan, − and gelatin, − as well as synthetic polymers, such as poly(ethylene glycol), − poly(hydroxyethyl methacrylate), − poly(vinyl alcohol), − poly(2-oxazoline)s, − polyacrylamides, − and recently poly(2-isopropenyl-2-oxazoline)s. − …”

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Poly(N-allyl acrylamide) as a Reactive Platform toward Functional Hydrogels

et al. 2023

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The synthesis of poly(N-allyl acrylamide) (PNAllAm) as a platform for the preparation of functional hydrogels is described. The PNAllAm was synthesized via organocatalyzed amidation of poly(methyl acrylate) (PMA) with allylamine and characterized by 1H NMR spectroscopy, size exclusion chromatography (SEC), and turbidimetry, which allowed an estimation of the lower critical solution temperature of ∼26 °C in water. The PNAllAm was then used to make functional hydrogels via photoinitiated thiol–ene chemistry, where dithiothreitol (DTT) was used to cross-link the polymer chains. In addition, mercaptoethanol (ME) was added as a functional thiol to modulate the hydrogel properties. A decrease of the volume-phase transition temperature of the resulting hydrogels was observed with increasing ME content. Altogether this work introduces a straightforward way for the preparation of PNAllAm from PMA and demonstrates its value as a reactive polymer platform for the generation of functional hydrogels.

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Poly(N-allyl acrylamide) as a Reactive Platform toward Functional Hydrogels

et al. 2023

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“…Although alkane thiols [45,46,47] and aryl thiols [34,48,49,50] oxidized by H 2 O 2 to form the corresponding disulfide have been widely reported, a similar reaction for 4-MPBA as one for aryl thiols has rarely been reported. Khutoryanskiy et al only employed the reaction of 4-MPBA oxidized by H 2 O 2 to form disulfide bonds for cross-linking PVA (polyvinyl alcohol) [51]; however, the formation of boric acid through breaking the C-B bound was not mentioned, and the formation of disulfide bond was not characterized.…”

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Aggregation of Gold Nanoparticles Caused in Two Different Ways Involved in 4-Mercaptophenylboronic Acidand Hydrogen Peroxide

Liang

et al. 2019

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The difference in gold nanoparticle (AuNPs) aggregation caused by different mixing orders of AuNPs, 4-mercaptophenylboronic acid (4-MPBA), and hydrogen peroxide (H2O2) has been scarcely reported. We have found that the color change of a ((4-MPBA + AuNPs) + H2O2) mixture caused by H2O2 is more sensitive than that of a ((4-MPBA + H2O2) + AuNPs) mixture. For the former mixture, the color changes obviously with H2O2 concentrations in the range of 0~0.025%. However, for the latter mixture, the corresponding H2O2 concentration is in the range of 0~1.93%. The mechanisms on the color change originating from the aggregation of AuNPs occurring in the two mixtures were investigated in detail. For the ((4-MPBA + H2O2) + AuNPs) mixture, free 4-MPBA is oxidized by H2O2 to form bis(4-hydroxyphenyl) disulfide (BHPD) and peroxoboric acid. However, for the ((4-MPBA+AuNPs) + H2O2) mixture, immobilized 4-MPBA is oxidized by H2O2 to form 4-hydroxythiophenol (4-HTP) and boric acid. The decrease in charge on the surface of AuNPs caused by BHPD, which has alarger steric hindrance, is poorer than that caused by -4-HTP, and this is mainly responsible for the difference in the aggregation of AuNPs in the two mixtures. The formation of boric acid and peroxoboric acid in the reaction between 4-MPBA and H2O2 can alter the pH of the medium, and the effect of the pH change on the aggregation of AuNPs should not be ignored. These findings not only offer a new strategy in colorimetric assays to expand the detection range of hydrogen peroxide concentrations but also assist in deepening the understanding of the aggregation of citrate-capped AuNPs involved in 4-MPBA and H2O2, as well as in developing other probes.

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“…Высокая чувствительность к глюкозе в фосфатно-солевом буфере была определена с помощью метода динамического светового рассеяния и флуоресцентной техники и она проявляется благодаря присутствию фенилбороновой кислоты. О глюкозочувствительности материалов на основе фенилбороновой кислоты упоминается также во множестве других источников [89][90][91]. В глюкозочувствительный наногель были загружены Ализарин красный С и инсулин.…”

Section: рисунок 3 схема радикального механизма тиол-ен реакции [19]unclassified