Adsorption and Release of Rose Bengal on Layer-by-Layer Films of Poly(Vinyl Alcohol) and Poly(Amidoamine) Dendrimers Bearing 4-Carboxyphenylboronic Acid

Abstract

Phenylboronic acid-bearing polyamidoamine dendrimer (PBA-PAMAM)/poly(vinyl alcohol) (PVA) multilayer films were prepared through the layer-by-layer (LbL) deposition of PBA-PAMAM solution and PVA solution. PBA-PAMAM/PVA films were constructed successfully through the formation of boronate ester bonds between the boronic acid moiety in PBA and 1,3-diol units in PVA. When the (PBA-PAMAM/PVA)5 films were immersed in rose bengal (RB) solution, RB was adsorbed onto the LbL films. The amount of RB adsorbed was higher in the LbL films immersed in acidic solution than in basic solution. The release of RB from the LbL films was also promoted in the basic solution, while it was suppressed in the acidic solution. The boronic acid ester is oxidized to phenol by hydrogen peroxide (H2O2) and the carbon-boron bond is cleaved, so that the (PBA-PAMAM/PVA)5 films can be decomposed by immersion in H2O2 solution. Therefore, when RB-adsorbed (PBA-PAMAM/PVA)5 films were immersed in H2O2 solution, the release of RB was moderately promoted when the solution was weakly acidic.

Voltammetric pH Measurements Using Azure A-Containing Layer-by-Layer Film Immobilized Electrodes

“…Layer-by-layer deposition is a technique used to form a nanometer-thick multilayer film on a solid substrate surface, such as metals and glass, via electrostatic interactions by alternately immersing the substrate in a polycation and polyanion solutions (Scheme 1) [1]. Formation of a thin multilayer film can be both driven by electrostatic interaction and by other types of interactions, such as biological affinity, e.g., avidin-biotin bonds [2][3][4], sugar-lectin bonds [5]; hydrogen bonds [6,7]; diol-phenylboronic acid bonds [8,9]; guest-host interactions [10]; and other low energy physical bonds [11][12][13]. Thus, a functional thin film can be formed from synthetic polymers and other materials, such as proteins, such as enzymes [14,15], polysaccharides [16,17], supramolecular compounds [18], and nanoparticles [19].…”

Layer-by-Layer Nanoarchitectonics Using Protein–Polyelectrolyte Complexes toward a Generalizable Tool for Protein Surface Immobilization

“…24 Therefore, the LbL assembly method has considerable potential for developing biofunctionalized materials with a great variety of architectures. 25 Since Decher et al's first report, the LbL method has been extended to a wide range of deposited materials 22 such as clay minerals, 26,27 viruses, 28 dendrimers, 29,30 gold colloids, 31 silica particles, 32 and proteins. 33−35 Interestingly, this versatile method enables the assembly of multicomponent protein films, which open a way to construct multifunctional systems.…”

“…Since Decher et al’s first report, the LbL method has been extended to a wide range of deposited materials such as clay minerals, , viruses, dendrimers, , gold colloids, silica particles, and proteins. − Interestingly, this versatile method enables the assembly of multicomponent protein films, which open a way to construct multifunctional systems . This is topical for various fields of research such as biomaterials, drug release, tissue engineering, and regenerative medicine.…”