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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

Chemical structures of DAB-BA-PAA, ABOL-BA-PAA, ChS, and PVA utilized as main components for multilayer formation. Control polymer DAB-Bn-PAA is similar to DAB-BA-PAA but with benzyl moiety instead of the phenylboronic acid moiety.
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Sch2: Chemical structures of DAB-BA-PAA, ABOL-BA-PAA, ChS, and PVA utilized as main components for multilayer formation. Control polymer DAB-Bn-PAA is similar to DAB-BA-PAA but with benzyl moiety instead of the phenylboronic acid moiety.

Mentions: Two phenylboronic acid-functionalized poly(amido amine)s (BA-PAA) differing in the presence of primary amine (DAB-BA-PAA) or primary alcohol (ABOL-BA-PAA) side groups (Scheme 2) have been synthesized and studied for their properties in forming multilayered thin films with two different diol-containing macromolecules. The presence of disulfide bonds in the polymer main chain renders them responsive to reducing agents. The branched structure of the BA-PAA adds multivalency to strengthen interactions with the diol-containing counterpart and increases overall multilayer stability. However, unlike the poly(amido amine) dendrimers (PAMAM) with high degree of branching, the BA-PAAs may still maintain structural flexibility in solution—a feature that has been reported to increase their potency as gene carriers (29,30). The linear form of ortho-substituted ABOL-BA-PAA itself has been previously reported to self-assemble into nanoparticles capable of intracellular delivery of alizarin red S (a diol-containing small molecule) as model drug with the BA-PAA polymer (16), implying the possibility of achieving nanoparticle-releasing multilayered system.Scheme 2


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

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

Chemical structures of DAB-BA-PAA, ABOL-BA-PAA, ChS, and PVA utilized as main components for multilayer formation. Control polymer DAB-Bn-PAA is similar to DAB-BA-PAA but with benzyl moiety instead of the phenylboronic acid moiety.
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch2: Chemical structures of DAB-BA-PAA, ABOL-BA-PAA, ChS, and PVA utilized as main components for multilayer formation. Control polymer DAB-Bn-PAA is similar to DAB-BA-PAA but with benzyl moiety instead of the phenylboronic acid moiety.
Mentions: Two phenylboronic acid-functionalized poly(amido amine)s (BA-PAA) differing in the presence of primary amine (DAB-BA-PAA) or primary alcohol (ABOL-BA-PAA) side groups (Scheme 2) have been synthesized and studied for their properties in forming multilayered thin films with two different diol-containing macromolecules. The presence of disulfide bonds in the polymer main chain renders them responsive to reducing agents. The branched structure of the BA-PAA adds multivalency to strengthen interactions with the diol-containing counterpart and increases overall multilayer stability. However, unlike the poly(amido amine) dendrimers (PAMAM) with high degree of branching, the BA-PAAs may still maintain structural flexibility in solution—a feature that has been reported to increase their potency as gene carriers (29,30). The linear form of ortho-substituted ABOL-BA-PAA itself has been previously reported to self-assemble into nanoparticles capable of intracellular delivery of alizarin red S (a diol-containing small molecule) as model drug with the BA-PAA polymer (16), implying the possibility of achieving nanoparticle-releasing multilayered system.Scheme 2

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