synthesis and structural characterization of bioactive pha and γ-pga oligomers for potential applications as a delivery system

Synthese und strukturelle Charakterisierung bioaktiver PHA- und γ-PGA-Oligomere für potenzielle Anwendungen als Verabreichungssystem

Síntese e caracterização estrutural de oligômeros bioativos de PHA e γ-PGA para potenciais aplicações como sistema de liberação

Clicks: 333
ID: 217911
2016
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Abstract
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-MS2 (electrospray ionization tandem mass spectrometry) and/or 1H 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.
Die (Trans)veresterungsreaktion bakterieller Biopolymere mit einer ausgewählten bioaktiven Verbindung mit einer Hydroxylgruppe wurde als zweckmäßige Methode zur Gewinnung von Konjugaten einer solchen Verbindung angewendet. Tyrosol, eine natürlich vorkommende phenolische Verbindung, wurde als Modell für eine bioaktive Verbindung mit einer Hydroxylgruppe ausgewählt. Als ausgewählte biologisch abbaubare Polyester bzw. Polyamide wurden Poly(3-hydroxybutyrat-co-4-hydroxybutyrat) (P(3HB-co-4HB)) beziehungsweise Poly-γ-glutaminsäure (γ-PGA) eingesetzt. Die (Trans)veresterungsreaktionen wurden in der Schmelze, vermittelt durch 4-Toluolsulfonsäure-Monohydrat, durchgeführt. Die Strukturen der (Trans)veresterungsprodukte wurden auf molekularer Ebene mithilfe von ESI-MS2- (Elektrospray-Ionisations-Tandem-Massenspektrometrie) und/oder 1H-NMR-Techniken (Kernspinresonanz) aufgeklärt. Die durchgeführten Analysen bestätigten, dass die entwickelte Methode zur Bildung von Konjugaten führt, in denen bioaktive Verbindungen kovalent an Biopolymerketten gebunden sind. Der Anteil der kovalent gebundenen bioaktiven Verbindungen in den resultierenden Konjugaten hängt von der Art der in der Synthese verwendeten Biopolymere ab.
A reação de (trans)esterificação de biopolímeros bacterianos com um composto bioativo selecionado contendo um grupo hidroxila foi aplicada como um método conveniente para a obtenção de conjugados de tal composto. O tirosol, um composto fenólico de ocorrência natural, foi selecionado como modelo de composto bioativo com um grupo hidroxila. Um poliéster e uma poliamida biodegradáveis selecionados, poli(3-hidroxibutirato-co-4-hidroxibutirato) (P(3HB-co-4HB)) e ácido poli-γ-glutâmico (γ-PGA), respectivamente, foram utilizados. As reações de (trans)esterificação foram realizadas em fusão, mediadas por ácido 4-toluenossulfônico monohidratado. As estruturas dos produtos de (trans)esterificação foram estabelecidas em nível molecular com o auxílio das técnicas de ESI-MS2 (espectrometria de massas em tandem com ionização por electrospray) e/ou RMN de 1H (ressonância magnética nuclear). As análises realizadas confirmaram que o método desenvolvido leva à formação de conjugados nos quais os compostos bioativos estão covalentemente ligados às cadeias biopoliméricas. A quantidade de compostos bioativos covalentemente ligados nos conjugados resultantes depende do tipo de biopolímero empregado na síntese.
Reference Key
kwiecie2016materialssynthesis Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;Iwona Kwiecień;Iza Radecka;Michał Kwiecień;Grażyna Adamus
Journal Nature Materials
Year 2016
DOI
10.3390/ma9050307
URL
http://www.mdpi.com/1996-1944/9/5/307
Keywords
biodegradable polymers polyhydroxyalkanoates conjugates electronics civil engineering (general)microscopydescriptive and experimental mechanics nuclear engineeringengineering (general)

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