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Multilayered Thin Films from Boronic Acid-Functional Poly(amido amine)s.

Hujaya SD, Engbersen JF, Paulusse JM - Pharm. Res. (2015)

Bottom Line: Biocompatibility of the resulting films was evaluated through cell culture experiments with COS-7 cells grown on the films.All of the multilayers are stable under physiological conditions in vitro and are responsive to reducing agents, owing to the presence of disulfide bonds in the polymers.Graphical Abstract Layer-by-Layer Assembly.

View Article: PubMed Central - PubMed

Affiliation: Department of Controlled Drug Delivery, MIRA Institute for Biomedical Technology and Technical Medicine, Faculty of Science and Technology, University of Twente, P.O. Box 217, 7500 AE, Enschede, The Netherlands.

ABSTRACT

Purpose: To investigate the properties of phenylboronic acid-functional poly(amido amine) polymers (BA-PAA) in forming multilayered thin films with poly(vinyl alcohol) (PVA) and chondroitin sulfate (ChS), and to evaluate their compatibility with COS-7 cells.

Methods: Copolymers of phenylboronic acid-functional poly(amido amine)s, differing in the content of primary amine (DAB-BA-PAA) or alcohol (ABOL-BA-PAA) side groups, were synthesized and applied in the formation of multilayers with PVA and ChS. Biocompatibility of the resulting films was evaluated through cell culture experiments with COS-7 cells grown on the films.

Results: PVA-based multilayers were thin, reaching ~100 nm at 10 bilayers, whereas ChS-based multilayers were thick, reaching ~600 nm at the same number of bilayers. All of the multilayers are stable under physiological conditions in vitro and are responsive to reducing agents, owing to the presence of disulfide bonds in the polymers. PVA-based films were demonstrated to be responsive to glucose at physiological pH at the investigated glucose concentrations (10-100 mM). The multilayered films displayed biocompatibility in cell culture experiments, promoting attachment and proliferation of COS-7 cells.

Conclusions: Responsive thin films based on boronic acid functional poly(amido amine)s are promising biocompatible materials for biomedical applications, such as drug releasing surfaces on stents or implants. Graphical Abstract Layer-by-Layer Assembly.

No MeSH data available.


Related in: MedlinePlus

Schematic illustration of possible interaction between primary alcohol and boronic acid side groups of ABOL-BA-PAA, thereby increasing affinity between reactants.
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Sch5: Schematic illustration of possible interaction between primary alcohol and boronic acid side groups of ABOL-BA-PAA, thereby increasing affinity between reactants.

Mentions: As shown in Table I, both the molecular weight and the degree of branching are relatively low in comparison with some reports on the one-pot-synthesized hyperbranched polymers (37,38) but are in agreement with a previous report utilizing the same CBA, ABOL and similar reaction procedure (29). Although this previous report concluded no significant difference in the branched vs linear PAA, we note significant increase in molecular weight of BA-containing PAAs reported in this study in comparison with previously reported linear BA-containing PAA (16). The previously reported linear BA-PAA was synthesized at 50°C. The reactivity of the secondary amine in 4AMPBA and BnDAB was most likely enhanced by the increase in reaction temperature to 70°C. The increase in reactivity is not significant as indicated by the relatively low degree of branching. In addition to the moderate increase in reaction temperature, branching was most likely limited by polymer solubility in the polymerization solvent (a high molecular weight insoluble portion was filtered off), and steric hindrance. It is interesting to note that ABOL-BA-PAA displayed a higher degree of branching as compared to DAB-BA-PAA. The interaction of the alcohol side chains with boronic acid possibly increases affinity between reactants (Scheme 5). Moreover, ABOL-BA-PAA may be more soluble than BOC-protected DAB-BA-PAA during polymerization, making it easier for the former to reach higher degree of polymerization.Scheme 5


Multilayered Thin Films from Boronic Acid-Functional Poly(amido amine)s.

Hujaya SD, Engbersen JF, Paulusse JM - Pharm. Res. (2015)

Schematic illustration of possible interaction between primary alcohol and boronic acid side groups of ABOL-BA-PAA, thereby increasing affinity between reactants.
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4526598&req=5

Sch5: Schematic illustration of possible interaction between primary alcohol and boronic acid side groups of ABOL-BA-PAA, thereby increasing affinity between reactants.
Mentions: As shown in Table I, both the molecular weight and the degree of branching are relatively low in comparison with some reports on the one-pot-synthesized hyperbranched polymers (37,38) but are in agreement with a previous report utilizing the same CBA, ABOL and similar reaction procedure (29). Although this previous report concluded no significant difference in the branched vs linear PAA, we note significant increase in molecular weight of BA-containing PAAs reported in this study in comparison with previously reported linear BA-containing PAA (16). The previously reported linear BA-PAA was synthesized at 50°C. The reactivity of the secondary amine in 4AMPBA and BnDAB was most likely enhanced by the increase in reaction temperature to 70°C. The increase in reactivity is not significant as indicated by the relatively low degree of branching. In addition to the moderate increase in reaction temperature, branching was most likely limited by polymer solubility in the polymerization solvent (a high molecular weight insoluble portion was filtered off), and steric hindrance. It is interesting to note that ABOL-BA-PAA displayed a higher degree of branching as compared to DAB-BA-PAA. The interaction of the alcohol side chains with boronic acid possibly increases affinity between reactants (Scheme 5). Moreover, ABOL-BA-PAA may be more soluble than BOC-protected DAB-BA-PAA during polymerization, making it easier for the former to reach higher degree of polymerization.Scheme 5

Bottom Line: Biocompatibility of the resulting films was evaluated through cell culture experiments with COS-7 cells grown on the films.All of the multilayers are stable under physiological conditions in vitro and are responsive to reducing agents, owing to the presence of disulfide bonds in the polymers.Graphical Abstract Layer-by-Layer Assembly.

View Article: PubMed Central - PubMed

Affiliation: Department of Controlled Drug Delivery, MIRA Institute for Biomedical Technology and Technical Medicine, Faculty of Science and Technology, University of Twente, P.O. Box 217, 7500 AE, Enschede, The Netherlands.

ABSTRACT

Purpose: To investigate the properties of phenylboronic acid-functional poly(amido amine) polymers (BA-PAA) in forming multilayered thin films with poly(vinyl alcohol) (PVA) and chondroitin sulfate (ChS), and to evaluate their compatibility with COS-7 cells.

Methods: Copolymers of phenylboronic acid-functional poly(amido amine)s, differing in the content of primary amine (DAB-BA-PAA) or alcohol (ABOL-BA-PAA) side groups, were synthesized and applied in the formation of multilayers with PVA and ChS. Biocompatibility of the resulting films was evaluated through cell culture experiments with COS-7 cells grown on the films.

Results: PVA-based multilayers were thin, reaching ~100 nm at 10 bilayers, whereas ChS-based multilayers were thick, reaching ~600 nm at the same number of bilayers. All of the multilayers are stable under physiological conditions in vitro and are responsive to reducing agents, owing to the presence of disulfide bonds in the polymers. PVA-based films were demonstrated to be responsive to glucose at physiological pH at the investigated glucose concentrations (10-100 mM). The multilayered films displayed biocompatibility in cell culture experiments, promoting attachment and proliferation of COS-7 cells.

Conclusions: Responsive thin films based on boronic acid functional poly(amido amine)s are promising biocompatible materials for biomedical applications, such as drug releasing surfaces on stents or implants. Graphical Abstract Layer-by-Layer Assembly.

No MeSH data available.


Related in: MedlinePlus