Polyhydroxyalkanoate-derived hydrogen-bond donors for the synthesis of new deep eutectic solvents

Haraźna, Katarzyna; Walas, Karolina; Urbańska, Patrycja; Witko, Tomasz; Snoch, Wojciech; Siemek, Agnieszka; Jachimska, Barbara; Krzan, Marcel; Napruszewska, Bogna D.; Witko, Małgorzata; Bednarz, Szczepan; Guzik, Maciej

doi:10.1039/c9gc00387h

Cited by 32 publications

(18 citation statements)

References 62 publications

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“…Thermogravimetric analysis (TGA) was carried out using a Netzsch STA 409 PC Luxx according to protocols described by Haraźna et al [ 42 ] Differential scanning calorimetry (DSC) experiment analyses were performed with a Mettler Toledo 822e calorimeter purged with argon. The samples were first heated from room temperature to 200 °C at 10 K min −1 to erase the thermal history, then the samples were cooled at 10 K min −1 to −80 °C and second heating run at 10 K min −1 were accomplished.…”

Section: Methodsmentioning

confidence: 99%

Physicochemical and Biological Characterisation of Diclofenac Oligomeric Poly(3-hydroxyoctanoate) Hybrids as β-TCP Ceramics Modifiers for Bone Tissue Regeneration

Haraźna

Cichoń

Skibiński

et al. 2020

IJMS

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Nowadays, regenerative medicine faces a major challenge in providing new, functional materials that will meet the characteristics desired to replenish and grow new tissue. Therefore, this study presents new ceramic-polymer composites in which the matrix consists of tricalcium phosphates covered with blends containing a chemically bounded diclofenac with the biocompatible polymer—poly(3-hydroxyoctanoate), P(3HO). Modification of P(3HO) oligomers was confirmed by NMR, IR and XPS. Moreover, obtained oligomers and their blends were subjected to an in-depth characterisation using GPC, TGA, DSC and AFM. Furthermore, we demonstrate that the hydrophobicity and surface free energy values of blends decreased with the amount of diclofenac modified oligomers. Subsequently, the designed composites were used as a substrate for growth of the pre-osteoblast cell line (MC3T3-E1). An in vitro biocompatibility study showed that the composite with the lowest concentration of the proposed drug is within the range assumed to be non-toxic (viability above 70%). Cell proliferation was visualised using the SEM method, whereas the observation of cell penetration into the scaffold was carried out by confocal microscopy. Thus, it can be an ideal new functional bone tissue substitute, allowing not only the regeneration and restoration of the defect but also inhibiting the development of chronic inflammation.

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Section: Methodsmentioning

confidence: 99%

Physicochemical and Biological Characterisation of Diclofenac Oligomeric Poly(3-hydroxyoctanoate) Hybrids as β-TCP Ceramics Modifiers for Bone Tissue Regeneration

Haraźna

Cichoń

Skibiński

et al. 2020

IJMS

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“…Therefore, tested acids showed a temperature of melting (T onset ) from 33°C to 66°C and could be applied as PCM in this temperature range. 30 Thermal and chemical stability of pure 3-HFAs were tested using DSC method and 1 H NMR spectroscopy. Considerably lower melting temperatures as well as lower value of the latent heat of melting (ΔH m ) could possibly be due to the presence of 8.5% (w/w) of unsaturated octanoic acid in the sample after described treatment of the polymer, as judged by GCMS analysis.…”

Section: Differential Scanning Analysis Of Pure 3-hfasmentioning

confidence: 99%

“…30 Thermal and chemical stability of pure 3-HFAs were tested using DSC method and 1 H NMR spectroscopy. 30 Small variations in the melting temperature and the change in the latent heat of melting of each of the tested acids were observed, and it can be concluded that they are thermally stable, in cyclic heating and cooling, in the tested temperature range (Figure 2A).…”

Section: Differential Scanning Analysis Of Pure 3-hfasmentioning

confidence: 99%

“…29 Recently, (R)-3hydroxynonanoic and (R)-3-hydroxyheptanoic acids from the PHA were successfully used in the preparations of new deep eutectic solvents with low toxicity. 30 Thermal and chemical stability of pure 3-HFAs were tested using DSC method and 1 H NMR spectroscopy. As a model, we used 3-hydroxydodecanoic acid (Figure 2).…”

Section: Differential Scanning Analysis Of Pure 3-hfasmentioning

confidence: 99%

“…8 Similarly, melting temperatures of 3-hydroxyheptanoic and 3hydroxynonanoic acid were reported with the similar trend observed. 30…”

Section: Differential Scanning Analysis Of Pure 3-hfasmentioning

confidence: 99%

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Thermal properties of 3‐hydroxy fatty acids and their binary mixtures as phase change energy storage materials

et al. 2019

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In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time.These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs.3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.

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Preparation of lignin nanoparticles via ultra‐fast microwave‐assisted fractionation of lignocellulose using ternary deep eutectic solvents

Yan

Wang

Chen

et al. 2023

Biotech & Bioengineering

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Lignin separation from natural lignocellulose for the preparation of lignin nanoparticles (LNPs) is often challenging owing to the recalcitrant and complex structure of lignocellulose. This paper reports a strategy for the rapid synthesis of LNPs via microwave-assisted lignocellulose fractionation using ternary deep eutectic solvents (DESs). A novel ternary DES with strong hydrogen bonding was prepared using choline chloride, oxalic acid, and lactic acid in a 1:0.5:1 ratio. Efficient fractionation of rice straw (0.5 × 2.0 cm) (RS) was realized by the ternary DES under microwave irradiation (680 W) within only 4 min, and 63.4% of lignin could be separated from the RS to prepare LNPs with a high lignin purity (86.8%), an average particle size of 48-95 nm, and a narrow size distribution. The mechanism of lignin conversion was also investigated, which revealed that dissolved lignin aggregated into LNPs via π-π stacking interactions.

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Polyhydroxyalkanoate-derived hydrogen-bond donors for the synthesis of new deep eutectic solvents

Abstract: Polyhydroxyalkanoate monomers can serve as deep eutectic solvents components.

Cited by 32 publications

References 62 publications

Physicochemical and Biological Characterisation of Diclofenac Oligomeric Poly(3-hydroxyoctanoate) Hybrids as β-TCP Ceramics Modifiers for Bone Tissue Regeneration

Physicochemical and Biological Characterisation of Diclofenac Oligomeric Poly(3-hydroxyoctanoate) Hybrids as β-TCP Ceramics Modifiers for Bone Tissue Regeneration

Thermal properties of 3‐hydroxy fatty acids and their binary mixtures as phase change energy storage materials

Preparation of lignin nanoparticles via ultra‐fast microwave‐assisted fractionation of lignocellulose using ternary deep eutectic solvents

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