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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

The equilibria of boronate ester formation and relevant Lewis acidity.
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Sch1: The equilibria of boronate ester formation and relevant Lewis acidity.

Mentions: In the development of multi-responsive drug delivery systems, the reversible ester formation of boronic acid (BA) with diols (Scheme 1) has been of widespread interest (1,2). This interaction is considered quite special not only due to its specific coordinative covalent nature, but also due to the dynamic properties of the interaction (3,4). This chemistry is very relevant to the biomedical field as it takes place under physiological conditions, is highly sensitive to pH, and concerns diol-moieties which can be found in many biologically relevant compounds and macromolecules, most notably carbohydrates and sugars. Therefore, this ester formation has been widely exploited for development of blood glucose sensors (5–9), separation agents (10–12), and therapeutic delivery systems (hydrogels (13,14), micro- and nanoparticles (2,15,16)) for insulin (17–20), and other drugs (21–23). Phenylboronic acid, a more reactive derivative of alkylboronic acid in ester formation with diols, has been found to selectively inhibit tumor cells without much effect on non-tumorigenic cell lines (24).Scheme 1


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

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

The equilibria of boronate ester formation and relevant Lewis acidity.
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch1: The equilibria of boronate ester formation and relevant Lewis acidity.
Mentions: In the development of multi-responsive drug delivery systems, the reversible ester formation of boronic acid (BA) with diols (Scheme 1) has been of widespread interest (1,2). This interaction is considered quite special not only due to its specific coordinative covalent nature, but also due to the dynamic properties of the interaction (3,4). This chemistry is very relevant to the biomedical field as it takes place under physiological conditions, is highly sensitive to pH, and concerns diol-moieties which can be found in many biologically relevant compounds and macromolecules, most notably carbohydrates and sugars. Therefore, this ester formation has been widely exploited for development of blood glucose sensors (5–9), separation agents (10–12), and therapeutic delivery systems (hydrogels (13,14), micro- and nanoparticles (2,15,16)) for insulin (17–20), and other drugs (21–23). Phenylboronic acid, a more reactive derivative of alkylboronic acid in ester formation with diols, has been found to selectively inhibit tumor cells without much effect on non-tumorigenic cell lines (24).Scheme 1

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