H₂O₂-Induced Decomposition of Layer-by-Layer Films Consisting of Phenylboronic Acid-Bearing Poly(allylamine) and Poly(vinyl alcohol)

Abstract

Layer-by-layer (LbL) films were prepared by an alternate deposition of phenylboronic acid-bearing poly(allylamine hydrochloride) (PBA-PAH) and poly(vinyl alcohol) (PVA) on the surface of a quartz slide to develop thin films that can be decomposed in response to hydrogen peroxide (H2O2). The PBA-PAH/PVA films decomposed in the presence of H2O2; the degree and kinetics of decomposition depend on the concentration of H2O2 and on the pH of the solution. For example, the film decomposition completely occurred in 30 min in 1.0 mM H2O2 solution at pH 7.4, while it took 180 min in 0.1 mM H2O2 solution. The H2O2-induced decomposition of the film can be explained in terms of the oxidative scission of the carbon-boron bond in PBA residues in the PBA-PAH chains. A potential use of the PBA-PAH/PVA films in developing H2O2-sensitive delivery systems was suggested.

Clustering Small Dendrimers into Nanoaggregates for Efficient DNA and siRNA Delivery with Minimal Toxicity

“…These compounds are reported to covalently bind with boronic acid groups at physiological conditions, [ 27,29,44,45 ] thus reducing the potential of self-assembly and nanosized dendriplex formation ( Figure S6, Supporting Information). As expected, pretreatment of G2-PBA-7 with these compounds signifi cantly decreases its transfection effi cacy ( Figure 6 ).…”

Preparation of multilayer films consisting of glucose oxidase and poly(amidoamine) dendrimer and their stability

“…It is noted here that, in the presence of 1 mM glucose, the film decomposed nearly completely in spite of much smaller binding constant of glucose (i.e., 4.6 M −1 ) than the other sugars. These results suggest that glucose-induced film decomposition originates mainly from the oxidative scission of carbon-boron bond of PBA-PAMAM by H 2 O 2 [30][31][32][33]. Figure 4B shows that the kinetics and the degree of film decomposition are dependent on the glucose concentration.…”

“…1). The reaction products, gluconic acid and H 2 O 2 , may affect the film stability in two different routes; a pH change resulting from deprotonation of gluconic acid and/or an oxidative scission of carbon-boron bond of PBA-PAMAM by H 2 O 2 [30][31][32][33]. In addition, glucose might competitively bind to PBA-PAMAM in the film to cleave the boronate ester bonds between GOx and PBA-PAMAM.…”

Recent Progress in Electrochemical Biosensors for Glycoproteins

“…The sensor responds to 0.1%–1.5% HbA1c under optimum conditions. However, careful attention is required in this protocol because carbon-boron (C-B) bonds in PBA and its esters are sometimes oxidatively cleaved by H 2 O 2 [106,107,108]. …”