Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

Adamus, Grażyna; Kurcok, Piotr; Kowalczuk, Marek

doi:10.14314/polimery.2017.317

Cited by 10 publications

(16 citation statements)

References 45 publications

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“…PHAs that contain functional groups are also extremely appealing for biomedical usage as they allow for further chemical modification. This could be in the form of bioactive oligomers that distribute drugs using pH-controlled release [55]. Polyethylene glycol (PEG) is a polyether that has been combined with PHA to alter its properties.…”

Section: Discussionmentioning

confidence: 99%

The Microbial Production of Polyhydroxyalkanoates from Waste Polystyrene Fragments Attained Using Oxidative Degradation

et al. 2018

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Excessive levels of plastic waste in our oceans and landfills indicate that there is an abundance of potential carbon sources with huge economic value being neglected. These waste plastics, through biological fermentation, could offer alternatives to traditional petrol-based plastics. Polyhydroxyalkanoates (PHAs) are a group of plastics produced by some strains of bacteria that could be part of a new generation of polyester materials that are biodegradable, biocompatible, and, most importantly, non-toxic if discarded. This study introduces the use of prodegraded high impact and general polystyrene (PS0). Polystyrene is commonly used in disposable cutlery, CD cases, trays, and packaging. Despite these applications, some forms of polystyrene PS remain financially and environmentally expensive to send to landfills. The prodegraded PS0 waste plastics used were broken down at varied high temperatures while exposed to ozone. These variables produced PS flakes (PS1–3) and a powder (PS4) with individual acid numbers. Consequently, after fermentation, different PHAs and amounts of biomass were produced. The bacterial strain, Cupriavidus necator H16, was selected for this study due to its well-documented genetic profile, stability, robustness, and ability to produce PHAs at relatively low temperatures. The accumulation of PHAs varied from 39% for prodegraded PS0 in nitrogen rich media to 48% (w/w) of dry biomass with the treated PS. The polymers extracted from biomass were analyzed using nuclear magnetic resonance (NMR) and electrospray ionization tandem mass spectrometry (ESI-MS/MS) to assess their molecular structure and properties. In conclusion, the PS0–3 specimens were shown to be the most promising carbon sources for PHA biosynthesis; with 3-hydroxybutyrate and up to 12 mol % of 3-hydroxyvalerate and 3-hydroxyhexanoate co-monomeric units generated.

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Section: Discussionmentioning

confidence: 99%

The Microbial Production of Polyhydroxyalkanoates from Waste Polystyrene Fragments Attained Using Oxidative Degradation

et al. 2018

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“…Both MALDI and ESI MS, in some cases with the support of MS/MS and/or IM‐MS, have been used in the characterization of polymer conjugates, to confirm the effective functionalization and the success of the synthetic approch . The transesterification reaction of PHAs has been used as a strategic and simple tool for the synthesis of delivery systems for selected bioactive compounds, holding carboxyl or hydroxyl functionalities.…”

Section: Characterization Of Bioresorbable Polymers By Msmentioning

confidence: 99%

“…The transesterification reaction of PHAs has been used as a strategic and simple tool for the synthesis of delivery systems for selected bioactive compounds, holding carboxyl or hydroxyl functionalities. The structures of transesterification products were established at the molecular level by ESI‐MS/MS and 1 H NMR . The transesterification reaction of bacterial biopolymers with tyrosol was applied as a convenient method for obtaining polymer conjugates.…”

Section: Characterization Of Bioresorbable Polymers By Msmentioning

confidence: 99%

Mass spectrometry in bioresorbable polymer development, degradation and drug‐release tracking

Rizzarelli

Rapisarda

Valenti

2020

Rapid Comm Mass Spectrometry

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A detailed characterization of polymeric matrices and appropriate degradation monitoring techniques are required to sustain the development of new materials as well as to enlarge the applications of the old ones. In fact, polymer analysis is essential for the clarification of the intrinsic relationship between structure and properties that ascertains the industrial applications in diverse fields. In bioresorbable and biodegradable polymers, the role of analytical methods is dual since it is pointed both at the polymeric matrices and at degradation tracking. The structural architectures, the mechanical and morphological properties, and the degradation rate, are of outstanding importance for a specific application. In some cases, the complexity of the polymer structure, the processes of decomposition or the low concentration of the degradation products need the concurrent use of different complementary analytical techniques to give detailed information of the reactions taking place. Several analytical methods are used in bioresorbable polymer development and degradation tracking. Among them, mass spectrometry (MS) plays an essential role and it is used to refine polymer syntheses, for its high sensitivity, to highlight degradation mechanism by detecting compounds present in trace amounts, or to track the degradation product profile and to study drug release. In fact, elucidation of reaction mechanisms and polymer structure, attesting to the purity and detecting defects as well as residual catalysts, in biodegradable and bioresorbable polymers, requires sensitive analytical characterization methods that are essential in providing an assurance of safety, efficacy and quality. This review aims to provide an overview of the MS strategies used to support research and development of resorbable polymers as well as to investigate their degradation mechanisms. It is focused on the most significant studies concerning synthetic bioresorbable matrices (polylactide, polyglycolide and their copolymers, polyhydroxybutyrate, etc.), published in the last ten years.

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“…This is well visible by the natural occurrence of PHA building blocks like 3-hydroxybutyrate (3HB) and related oligomers in the blood stream of humans and animals (reviewed by [ 4 , 5 , 6 , 7 ]). In addition, monomers and oligomers of hydroxyalkanotes derived from natural aliphatic PHA and synthetic analogues are reported to exert bioactive functions [ 8 ]. In the context of biobased polyester oligomers, Utsunomia and colleagues recently reported on the production of oligomers consisting of lactate and 3HB; these oligomers were produced and excreted using recombinant Escherichia coli ; co-feeding of E. coli with diethylene glycol resulted in the formation of lactate-3HB oligomers with hydroxyl termini.…”

Section: Introductionmentioning

confidence: 99%

Biodegradable and Biocompatible Polyhydroxy-alkanoates (PHA): Auspicious Microbial Macromolecules for Pharmaceutical and Therapeutic Applications

2018

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Polyhydroxyalkanoates (PHA) are bio-based microbial biopolyesters; their stiffness, elasticity, crystallinity and degradability are tunable by the monomeric composition, selection of microbial production strain, substrates, process parameters during production, and post-synthetic processing; they display biological alternatives for diverse technomers of petrochemical origin. This, together with the fact that their monomeric and oligomeric in vivo degradation products do not exert any toxic or elsewhere negative effect to living cells or tissue of humans or animals, makes them highly stimulating for various applications in the medical field. This article provides an overview of PHA application in the therapeutic, surgical and tissue engineering area, and reviews strategies to produce PHA at purity levels high enough to be used in vivo. Tested applications of differently composed PHA and advanced follow-up products as carrier materials for controlled in vivo release of anti-cancer drugs or antibiotics, as scaffolds for tissue engineering, as guidance conduits for nerve repair or as enhanced sutures, implants or meshes are discussed from both a biotechnological and a material-scientific perspective. The article also describes the use of traditional processing techniques for production of PHA-based medical devices, such as melt-spinning, melt extrusion, or solvent evaporation, and emerging processing techniques like 3D-printing, computer-aided wet-spinning, laser perforation, and electrospinning.

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Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

Cited by 10 publications

References 45 publications

The Microbial Production of Polyhydroxyalkanoates from Waste Polystyrene Fragments Attained Using Oxidative Degradation

The Microbial Production of Polyhydroxyalkanoates from Waste Polystyrene Fragments Attained Using Oxidative Degradation

Mass spectrometry in bioresorbable polymer development, degradation and drug‐release tracking

Biodegradable and Biocompatible Polyhydroxy-alkanoates (PHA): Auspicious Microbial Macromolecules for Pharmaceutical and Therapeutic Applications

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