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Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System

The (trans)esterification reaction of bacterial biopolymers with a selected bioactive compound with a hydroxyl group was applied as a convenient method for obtaining conjugates of such compound. Tyrosol, a naturally occurring phenolic compound, was selected as a model of a bioactive compound with a...

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Detalles Bibliográficos
Autores principales: Kwiecień, Iwona, Radecka, Iza, Kwiecień, Michał, Adamus, Grażyna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5503025/
https://www.ncbi.nlm.nih.gov/pubmed/28773432
http://dx.doi.org/10.3390/ma9050307
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author Kwiecień, Iwona
Radecka, Iza
Kwiecień, Michał
Adamus, Grażyna
author_facet Kwiecień, Iwona
Radecka, Iza
Kwiecień, Michał
Adamus, Grażyna
author_sort Kwiecień, Iwona
collection PubMed
description The (trans)esterification reaction of bacterial biopolymers with a selected bioactive compound with a hydroxyl group was applied as a convenient method for obtaining conjugates of such compound. Tyrosol, a naturally occurring phenolic compound, was selected as a model of a bioactive compound with a hydroxyl group. Selected biodegradable polyester and polyamide, poly(3-hydroxybutyrate-co-4-hydroxybutyrate) (P(3HB-co-4HB)) and poly-γ-glutamic acid (γ-PGA), respectively, were used. The (trans)esterification reactions were carried out in melt mediated by 4-toluenesulfonic acid monohydrate. The structures of (trans)esterification products were established at the molecular level with the aid of ESI-MS(2) (electrospray ionization tandem mass spectrometry) and/or (1)H NMR (nuclear magnetic resonance) techniques. Performed analyses confirmed that the developed method leads to the formation of conjugates in which bioactive compounds are covalently bonded to biopolymer chains. The amount of covalently bonded bioactive compounds in the resulting conjugates depends on the type of biopolymers applied in synthesis.
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spelling pubmed-55030252017-07-28 Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System Kwiecień, Iwona Radecka, Iza Kwiecień, Michał Adamus, Grażyna Materials (Basel) Article The (trans)esterification reaction of bacterial biopolymers with a selected bioactive compound with a hydroxyl group was applied as a convenient method for obtaining conjugates of such compound. Tyrosol, a naturally occurring phenolic compound, was selected as a model of a bioactive compound with a hydroxyl group. Selected biodegradable polyester and polyamide, poly(3-hydroxybutyrate-co-4-hydroxybutyrate) (P(3HB-co-4HB)) and poly-γ-glutamic acid (γ-PGA), respectively, were used. The (trans)esterification reactions were carried out in melt mediated by 4-toluenesulfonic acid monohydrate. The structures of (trans)esterification products were established at the molecular level with the aid of ESI-MS(2) (electrospray ionization tandem mass spectrometry) and/or (1)H NMR (nuclear magnetic resonance) techniques. Performed analyses confirmed that the developed method leads to the formation of conjugates in which bioactive compounds are covalently bonded to biopolymer chains. The amount of covalently bonded bioactive compounds in the resulting conjugates depends on the type of biopolymers applied in synthesis. MDPI 2016-04-25 /pmc/articles/PMC5503025/ /pubmed/28773432 http://dx.doi.org/10.3390/ma9050307 Text en © 2016 by the authors; Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kwiecień, Iwona
Radecka, Iza
Kwiecień, Michał
Adamus, Grażyna
Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System
title Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System
title_full Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System
title_fullStr Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System
title_full_unstemmed Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System
title_short Synthesis and Structural Characterization of Bioactive PHA and γ-PGA Oligomers for Potential Applications as a Delivery System
title_sort synthesis and structural characterization of bioactive pha and γ-pga oligomers for potential applications as a delivery system
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5503025/
https://www.ncbi.nlm.nih.gov/pubmed/28773432
http://dx.doi.org/10.3390/ma9050307
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