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1.
Int J Biol Macromol ; 270(Pt 1): 132076, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38705324

ABSTRACT

The cross-linked enzyme (CLEs) of Thermomyces lanuginosa lipase (TLL) was prepared in an isocyanide-based multi-component reactions (ICMRs) platform by applying three di-acidic cross-linkers to unveil more factors contributing to the functional properties of CLEs. The linkers were 1,11-undecanedicarboxylic acid, azelaic acid, and adipic acid with 11, 7, and 4 carbon lengths, respectively, providing a proper tool to investigate the effect of linker length on the activity, stability, and selectivity of the resulting CLEs. The immobilization yields of 60-90 % and the specific activities of 168, 88.4 and 49 U/mg were obtained for the CLEs of 1,11-undecanedicarboxylic acid, azelaic acid, adipic acid, respectively. The lower activity of azelaic and adipic acid-mediated CLEs compared to the soluble TLL (110 U/mg) was explained by in silico calculations. The results revealed that as opposed to 1,11-undecanedicarboxylic acid, both linkers tended to penetrate the enzyme active site, thus resulting in a major inhibitory effect on the enzyme functionality. The thermal and co-solvent stability of the immobilized derivatives improved compared to those of free TLL. The selectivity of CLEs was also examined by catalytic release of main omega-3 fatty acids from fish oil, presenting the highest selectivity of 22 for the CLEs of azelaic acid.


Subject(s)
Cross-Linking Reagents , Enzymes, Immobilized , Lipase , Enzymes, Immobilized/chemistry , Enzymes, Immobilized/metabolism , Lipase/chemistry , Lipase/metabolism , Cross-Linking Reagents/chemistry , Enzyme Stability , Eurotiales/enzymology , Adipates/chemistry , Carbon/chemistry , Dicarboxylic Acids/chemistry
2.
Eur J Pharm Biopharm ; 200: 114335, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38768765

ABSTRACT

The study endeavors the fabrication of extended-release adipic acid (APA) buccal films employing a quality by design (QbD) approach. The films intended for the treatment of xerostomia were developed utilizing hot-melt extrusion technology. The patient-centered quality target product profile was created, and the critical quality attributes were identified accordingly. Three early-stage formulation development trials, complemented by risk assessment aligned the formulation and process parameters with the product quality standards. Employing a D-optimal mixture design, the formulations were systematically optimized by evaluating three formulation variables: amount of the release-controlling polymer Eudragit® (E RSPO), bioadhesive agent Carbopol® (CBP 971P), and pore forming agent polyethylene glycol (PEG 1500) as independent variables, and % APA release in 1, 4 and 8 h as responses. Using design of experiment software (Design-Expert®), a total of 16 experimental runs were computed and extruded using a Thermofisher ScientificTM twin screw extruder. All films exhibited acceptable content uniformity and extended-release profiles with the potential for releasing APA for at least 8 h. Films containing 30% E RSPO, 10% CBP 971P, and 20% PEG 1500 released 88.6% APA in 8 h. Increasing the CBP concentration enhanced adhesiveness and swelling capacities while decreasing E RSPO concentration yielded films with higher mechanical strength. The release kinetics fitted well into Higuchi and Krosmeyer-Peppas models indicating a Fickian diffusion release mechanism.


Subject(s)
Delayed-Action Preparations , Drug Liberation , Xerostomia , Xerostomia/drug therapy , Hot Melt Extrusion Technology/methods , Polyethylene Glycols/chemistry , Humans , Administration, Buccal , Chemistry, Pharmaceutical/methods , Adipates/chemistry , Acrylates/chemistry , Polymethacrylic Acids/chemistry , Polymers/chemistry , Drug Compounding/methods
3.
J Hazard Mater ; 472: 134603, 2024 Jul 05.
Article in English | MEDLINE | ID: mdl-38749243

ABSTRACT

Polybutylene adipate terephthalic acid (PBAT) is an emerging biodegradable material in food packaging. However, concerns have been raised regarding the potential hazards it could pose to food safety. In this study, the changes of PBAT films during food contact and the release of small molecules were inestigated by a multiscale approach. On a macro-scale, the surface roughness of the films increased with the reduction in the concentration of food simulants and the increase in contact temperatures, especially after immersion in acidic food environments. On a micro-scale, the crystallinity (Xc) and degradation indexes (DI) of the films increased by 5.7-61.2% and 7.8-48.6%, respectively, which led to a decrease in thermal stability. On a scale approaching the molecular level, 2,4-di-tert-butylphenol (2,4-DTBP) was detected by gas chromatography-mass spectrometry (GC-MS/MS) with the highest migration content, and the release behavior of 2,4-DTBP was further investigated by migration kinetics. In addition, terephthalic acid (TPA), a hydrolysis product of PBAT, was detected in acidic food environments by liquid chromatography-mass spectrometry (LC-MS/MS). The results of this study could provide practical guidance and assistance to promote sustainable development in the field of food packaging.


Subject(s)
Food Packaging , Phthalic Acids , Phthalic Acids/chemistry , Polyesters/chemistry , Adipates/chemistry , Food Contamination/analysis , Gas Chromatography-Mass Spectrometry
4.
Mar Pollut Bull ; 201: 116261, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38537567

ABSTRACT

Marine microorganisms have been reported to degrade microplastics. However, the degradation mechanisms are still poorly understood. In this study, a bacterium Roseibium aggregatum ZY-1 was isolated from seawater, which can degrade poly(butylene adipate-co-terephthalate) (PBAT). The PBAT-PLA(polylactic acid, PLA) films, before and after degradation, were characterized by scanning electron microscope (SEM) and Fourier transform infrared spectrometer (FTIR), the weight loss rate and water contact angle were measured. The results indicate that ZY-1 colonized on PBAT-PLA film, changed the functional groups and decreased water contact angle of PBAT-PLA film. Moreover, liquid chromatography mass spectrometry (LC-MS) analysis reveales that PBAT was degraded into its oligomers (TB, BTB) and monomers (T, A) during 10 days, and adipic acid (A) could be used as a sole carbon source. The whole genome sequencing analyses illustrate the mechanisms and enzymes such as PETase, carboxylesterases, arylesterase (PpEst) and genes like pobA, pcaBCDFGHIJKT, dcaAEIJK, paaGHJ involved in PBAT degradation. Therefore, the R. aggregatum ZY-1 will be a promising candidate of PBAT degradation.


Subject(s)
Alkenes , Phthalic Acids , Plastics , Polyesters , Polyesters/chemistry , Adipates/chemistry , Bacteria/metabolism , Water
5.
J Control Release ; 369: 573-590, 2024 May.
Article in English | MEDLINE | ID: mdl-38554773

ABSTRACT

Postoperative abdominal adhesions are a common clinical problem after surgery and can cause many serious complications. Current most commonly used antiadhesion products are less effective due to their short residence time and focus primary on barrier function. Herein, we developed a sprayable hydrogel barrier (sHA-ADH/OHA-E) with self-regulated drug release based on ROS levels at the trauma site, to serve as a smart inflammatory microenvironment modulator and GATA6+ macrophages trap for non-adherent recovery from abdominal surgery. Sulfonated hyaluronic acid (HA) conjugates modified with adipic dihydrazide (sHA-ADH), and oxidized HA conjugates grafted with epigallocatechin-3-gallate (EGCG) via ROS-cleavable boronate bonds (OHA-E) were synthesized. sHA-ADH/OHA-E hydrogel was facilely fabricated within 5 s after simply mixing sHA-ADH and OHA-E through forming dynamic covalent acylhydrazones. With good biocompatibility, appropriate mechanical strength, tunable shear-thinning, self-healing, asymmetric adhesion, and reasonable in vivo retention time, sHA-ADH/OHA-E hydrogel meets the requirements of a perfect physical barrier. Intriguingly, sulfonic acid groups endowed the hydrogel with satisfactory anti-fibroblast and macrophage attachment capability, and were demonstrated for the first time to act as polyanion traps to prevent GATA6+ macrophages aggregation. Importantly, EGCG could be intelligently released by ROS triggering to alleviate oxidative stress and promote proinflammatory M1 macrophage polarize to antiinflammatory M2 phenotype. Further, the fibrinolytic system balance was restored to reduce fibrosis. Thanks to the above advantages, the sHA-ADH/OHA-E hydrogel exhibited excellent anti-adhesion effects in a rat sidewall defect-cecum abrasion model and is expected to be a promising and clinically translatable antiadhesion barrier.


Subject(s)
GATA6 Transcription Factor , Hyaluronic Acid , Hydrogels , Macrophages , Postoperative Complications , Reactive Oxygen Species , Tissue Adhesions/prevention & control , Animals , Hydrogels/chemistry , Hydrogels/administration & dosage , Macrophages/drug effects , Macrophages/metabolism , Reactive Oxygen Species/metabolism , Hyaluronic Acid/chemistry , Postoperative Complications/prevention & control , GATA6 Transcription Factor/metabolism , Catechin/analogs & derivatives , Catechin/chemistry , Catechin/administration & dosage , Catechin/pharmacology , Rats, Sprague-Dawley , Mice , Adipates/chemistry , Male , Abdomen/surgery , RAW 264.7 Cells , Free Radical Scavengers/administration & dosage , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Drug Liberation
6.
Int J Biol Macromol ; 259(Pt 2): 129355, 2024 Feb.
Article in English | MEDLINE | ID: mdl-38218295

ABSTRACT

Polylactide/poly(butylene adipate-co-terephthalate) (PLA/PBAT) blends were compatibilized using dicumyl peroxide (DCP) and poly(ethylene glycol) 600 diacrylate (PEG600DA) through a one-step melt-blending process. The compatibility and performance of these blends were subsequently characterized. The results showed that grafts formed "in situ" effectively improved the compatibility and interfacial adhesion between PLA and PBAT phases. Melt viscosity and elasticity of both the PLA/PBAT/DCP and PLA/PBAT/DCP/PEG600DA blends evinced significant increases. Compared to PLA alone, both cold and melt crystallization abilities of the PLA/PBAT/DCP/PEG600DA blends were enhanced, with crystallinities increasing by 5 % - 10 %. Furthermore, the thermal stability, as well as hydrophobicity and oleophobicity of the compatibilized blends improved. In comparison with PLA, the elongation at break and notched impact strength for the PLA/PBAT/DCP/PEG600DA (60/40/0.1/4) blend achieved increases of 290 % and 44.23 kJ/m2, corresponding to improvements of 279 % and 1457 %, respectively. The toughening effect was substantially influenced by the ductile matrix (either a co-continuous phase or a flexible PBAT matrix) in addition to the strong interfacial adhesion and fine phase domain. These eco-friendly blends exhibit considerable potential for packaging articles and 3D printing products owing to their excellent mechanical properties and enhanced melt rheology.


Subject(s)
Alkenes , Peroxides , Phthalic Acids , Polyesters , Polyethylene Glycols , Polyesters/chemistry , Adipates/chemistry
7.
Int J Biol Macromol ; 253(Pt 6): 127408, 2023 Dec 31.
Article in English | MEDLINE | ID: mdl-37832616

ABSTRACT

Food safety concerns from spoilage and non-degradable packaging risk human health. Progress made in biodegradable plastic films, but limited study on biomass composite films with favorable morphological, mechanical, and inherent antibacterial properties for fresh meat preservation. Herein, we present a versatile packaging film created through the extrusion blowing process, combining oxidized starch (OST) with poly(butylene adipate-co-terephthalate) (PBAT). SEM analysis revealed even distribution of spherical OST particles on film's surface. FTIR spectra revealed new intermolecular hydrogen bonds between OST and PBAT. While combining OST slightly reduced tensile properties, all composite films met the required strength of 16.5 ± 1.39 MPa. Notably, films with 40 % OST showed over 98 % antibacterial rate against Staphylococcus aureus within 2 h. pH wasn't the main cause of bacterial growth inhibition; OST hindered growth by interfering with nutrient absorption and metabolism due to its carboxyl groups. Additionally, OST disrupted bacterial membrane integrity and cytoplasmic membrane potential. Remarkably, the OST/PBAT film excellently preserved chilled fresh pork, maintaining TVB-N level at 12.6 mg/100 g on day 6, microbial count at 105 CFU/g within 6-10 days, and sensory properties for 8 days. It extended pork's shelf life by two days compared to polyethylene film, suggesting an alternative to a synthetic material.


Subject(s)
Pork Meat , Red Meat , Humans , Swine , Animals , Polyesters/chemistry , Starch/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Food Packaging , Adipates/chemistry
8.
Int J Biol Macromol ; 253(Pt 4): 126976, 2023 Dec 31.
Article in English | MEDLINE | ID: mdl-37739283

ABSTRACT

The poly(butylene adipate-co-terephthalate) (PBAT)/poly(lactic acid) (PLA) films have been widely used due to their biological degradability and excellent comprehensive properties. However, the reports regarding biodegradable PLA/PBAT films are rather scarce. In this work, systematical investigations of biaxially stretched PLA/PBAT films were performed. Compared with unstretched films, the PLA/PBAT 75/25 films with the stretching ratio of 5 × 1 exhibited an improvement on the crystallinity of PLA from 6 % to 58.6 %. According to 2D-WAXS results, the orientation of the α crystal in the MD increased with the increase of the stretching ratio. The stretched films showed favorable barrier properties. The oxygen permeability (OP) of 2 × 2 PLA/PBAT 75/25 films shows a decrement of 22 % compared with that of the unstretched films. Interestingly, the uniaxially stretched PLA/PBAT 75/25 films exhibits increased surface roughness (Ra) for 3 × 1 film whereas decreased Ra for the 5 × 1 film, which could be related to the phase separation under stretching. The tensile strength in the machine direction (MD) of the PLA/PBAT 75/25 films was improved up to 51.6 MPa for 5 × 1 film, which is 45 % higher than that of unstretched counterpart. The stretched films exhibit excellent mechanical and barrier properties, which could be utilized in packaging industry with high potential.


Subject(s)
Oxygen , Polyesters , Oxygen/chemistry , Polyesters/chemistry , Food Packaging/methods , Adipates/chemistry
9.
Int J Biol Macromol ; 253(Pt 1): 126609, 2023 Dec 31.
Article in English | MEDLINE | ID: mdl-37652334

ABSTRACT

With increasing awareness on environmental protection and food safety, the development of biodegradable antimicrobial packaging materials has been paid growing emphasis. In this work, starch/poly(butylene adipate-co-terephthalate)/ε-polylysine hydrochloride films were prepared by extrusion blowing, and five commercial organically modified nanomontmorillonites (OMMT, including DK1, DK2, DK3, DK4, and DK5) were used as reinforcing agents. Intercalated structures were formed in the nanocomposite films, especially for those with DK3 and DK4 owing to their higher hydrophobicity and larger interlayer spacing. Adding OMMT weakened hydrogen bonds and the gelatinization/plasticization degree of starch. Morphology analysis revealed that the agglomeration of OMMT occurred in the films, but the film containing DK3 still showed a relatively homogeneous microstructure. Loading OMMT enhanced the strength, deformation resistance, thermal stability, surface hydrophobicity, but decreased barrier properties and water sensitivity of the films. Antimicrobial activity showed that the OMMT and ε-polylysine hydrochloride possessed a synergistic effect against Staphylococcus aureus and Escherichia coli. The maximum inhibition rate was observed in that with DK4, approaching 100 %. Findings supported the application of commercial OMMT in manufacturing biodegradable antimicrobial blown films.


Subject(s)
Anti-Infective Agents , Polyesters , Polyesters/chemistry , Polylysine/chemistry , Starch/chemistry , Anti-Infective Agents/pharmacology , Adipates/chemistry
10.
Environ Res ; 235: 116634, 2023 10 15.
Article in English | MEDLINE | ID: mdl-37442258

ABSTRACT

The development of composites for food packaging that have good mechanical and antimicrobial characteristics is still a major challenge. In applications like food packaging, the usage of poly (butylene adipate-co-terephthalate) (PBAT), which has an adversative effect on the environment and reduces petroleum resources, has grown widespread. The present work reveals PBAT composites reinforced with CNPs at a few percentages up to 5.0 wt %. The PBAT/CNPs composites were produced using the solvent casting method. The results of TGA studies, CNPs significantly enhanced the thermal stability of composites using PBAT. The mechanical strength of the PBAT composites was improved by increasing CNPs concentration. Tensile strength increased from 7.38 to 10.22 MPa, respectively. The oxygen transmission rate (OTR) decreased with increasing the CNPs concentrations. The barrier properties (H2O and O2) of PBAT were improved by the presence of CNPs. WVTR was calculated to be 108.6 ± 1.8 g/m2/day for PBAT. WVTR reduced when CNPs concentration in PBAT increased. The PCN-5.0 film sample had the lowest WVTR value, 34.1 ± 3.1 g/m2/day. For PCN-3.0, WVTR dropped by 45.39%, indicating and even with a 3.0 wt% loading of CNPs in PBAT, the rise is noticeable. Contact angle measurements indicate that PBAT/CNPs composites becomes hydrophobic after reinforcing. Gram-positive (S. aureus) and Gram-negative (E. coli) food-borne pathogenic microorganisms showed enhanced antimicrobial activity against the developed PBAT composites. The carrot pieces preserved their freshness for an extended period of 12 days while packaged in the PBAT/CNPs composite film, indicating that the film is an effective and excellent packaging for food materials.


Subject(s)
Nanoparticles , Polyesters , Polyesters/chemistry , Escherichia coli , Staphylococcus aureus , Adipates/chemistry , Carbon
11.
Bioresour Technol ; 385: 129430, 2023 Oct.
Article in English | MEDLINE | ID: mdl-37399952

ABSTRACT

PBAT (poly butylene adipate-co-terephthalate) is a widely used biodegradable plastic, but the knowledge about its metabolization in anaerobic environments is very limited. In this study, the anaerobic digester sludge from a municipal wastewater treatment plant was used as inoculum to investigate the biodegradability of PBAT monomers in thermophilic conditions. The research employs a combination of 13C-labelled monomers and proteogenomics to track the labelled carbon and identify the microorganisms involved. A total of 122 labelled peptides of interest were identified for adipic acid (AA) and 1,4-butanedio (BD). Through the time-dependent isotopic enrichment and isotopic profile distributions, Bacteroides, Ichthyobacterium, and Methanosarcina were proven to be directly involved in the metabolization of at least one monomer. This study provides a first insight into the identity and genomic potential of microorganisms responsible for biodegradability of PBAT monomers during anaerobic digestion under thermophilic conditions.


Subject(s)
Carbon , Polyesters , Polyesters/metabolism , Anaerobiosis , Adipates/chemistry
12.
Mar Pollut Bull ; 194(Pt B): 115295, 2023 Sep.
Article in English | MEDLINE | ID: mdl-37517280

ABSTRACT

Nylon fishing nets have excellent strength and durability, but when lost at sea, their insufficient decomposition destroys habitats and spawning grounds, and pollutes the marine environment. This led to the development of poly(butylene succinate) (PBS) resin for biodegradable fishing gear based on aliphatic fibers. Prompted by the low stiffness and elastic recovery of PBS, we introduced two additional components into the molecular structure of PBS: adipic acid and ethylene glycol. These two new components were combined with succinic acid and 1,4-butanediol, the existing components of PBS, to synthesize poly(butylene adipate-co-butylene succinate-co-ethylene adipate-co-ethylene succinate) (PBEAS) resin via esterification and polycondensation reactions of a quaternary aliphatic copolyester. Although the molecular weight and molecular weight distribution of PBEAS are similar to those of PBS, it has excellent tensile strength, stiffness, elastic recovery, and biodegradability, with a low melting point for good production efficiency. These improvements are expected to allow PBEAS resin to be applied to gill nets for fish that require high stiffness, thereby expanding the use of biodegradable fishing gear.


Subject(s)
Polyesters , Succinic Acid , Animals , Polyesters/chemistry , Hunting , Succinates/chemistry , Adipates/chemistry , Ethylenes
13.
J Colloid Interface Sci ; 641: 1043-1057, 2023 Jul.
Article in English | MEDLINE | ID: mdl-36996683

ABSTRACT

Sustainably derived poly(glycerol adipate) (PGA) has been deemed to deliver all the desirable features expected in a polymeric scaffold for drug-delivery, including biodegradability, biocompatibility, self-assembly into nanoparticles (NPs) and a functionalisable pendant group. Despite showing these advantages over commercial alkyl polyesters, PGA suffers from a series of key drawbacks caused by poor amphiphilic balance. This leads to weak drug-polymer interactions and subsequent low drug-loading in NPs, as well as low NPs stability. To overcome this, in the present work, we applied a more significant variation of the polyester backbone while maintaining mild and sustainable polymerisation conditions. We have investigated the effect of the variation of both hydrophilic and hydrophobic segments upon physical properties and drug interactions as well as self-assembly and NPs stability. For the first time we have replaced glycerol with the more hydrophilic diglycerol, as well as adjusting the final amphiphilic balance of the polyester repetitive units by incorporating the more hydrophobic 1,6-n-hexanediol (Hex). The properties of the novel poly(diglycerol adipate) (PDGA) variants have been compared against known polyglycerol-based polyesters. Interestingly, while the bare PDGA showed improved water solubility and diminished self-assembling ability, the Hex variation demonstrated enhanced features as a nanocarrier. In this regard, PDGAHex NPs were tested for their stability in different environments and for their ability to encode enhanced drug loading. Moreover, the novel materials have shown good biocompatibility in both in vitro and in vivo (whole organism) experiments.


Subject(s)
Glycerol , Nanoparticles , Drug Delivery Systems , Polyesters/chemistry , Pharmaceutical Preparations , Adipates/chemistry , Nanoparticles/chemistry , Drug Carriers/chemistry
14.
J Hazard Mater ; 441: 129958, 2023 01 05.
Article in English | MEDLINE | ID: mdl-36122523

ABSTRACT

In recent years, Poly(butylene adipate-co-terephthalate) (PBAT) films were wildly used due to its biodegradable properties. However, there are few reports of strains that can high efficiently degrade PBAT. Thermobifida fusca FXJ-1, a thermophilic actinomycete, was screened and identified from compost. FXJ-1 can efficiently degrade PBAT at 55 °C in MSM medium. The degradation rates of the pure PBAT film (PF), PBAT film used for mulching on agricultural fields (PAF), and PBAT-PLA-ST film (PPSF) were 82.87 ± 1.01%, 87.83 ± 2.00% and 52.53 ± 0.54%, respectively, after nine days of incubation in MSM medium. Cracking areas were monitored uniformly distributed on the surfaces of three kinds of PBAT-based films after treatment with FXJ-1 using scanning electron microscopy. The LC-MS results showed that PBAT might be degraded into adipic acid, terephthalic acid, butylene adipate, butylene terephthalate and butylene adipate-co-terephthalate, and these products are involved in the cleavage of ester bonds. We also found that amylase produced by FXJ-1 played an important role in the degradation of PPSF. FXJ-1 also showed an efficient PBAT-based films degradation ability in simulating compost environment, which implied its potential application in PBAT and starch-based film degradation by industrial composting.


Subject(s)
Composting , Polyesters , Adipates/chemistry , Alkenes , Amylases , Esters , Phthalic Acids , Polyesters/chemistry , Starch/chemistry , Thermobifida
15.
Waste Manag ; 144: 1-10, 2022 May 01.
Article in English | MEDLINE | ID: mdl-35286847

ABSTRACT

Poly(butylene adipate-co-terephthalate) (PBAT), a bioplastic consisting of aliphatic hydrocarbons and aromatic hydrocarbons, was developed to overcome the shortcomings of aliphatic and aromatic polyesters. Many studies report the use of PBAT as a blending material for improving properties of other bioplastics. However, there are few studies on microorganisms that degrade PBAT. We found six kinds of PBAT-degrading microorganisms from various soils. Among these, Bacillus sp. JY35 showed superior PBAT degradability and robustness to temperature. We monitored the degradation of PBAT films by Bacillus sp. JY35 using scanning electron microscopy, field emission scanning electron microscopy, Fourier-transform infrared spectroscopy, and gel permeation chromatography. GC-MS was used to measure the PBAT film degradation rate at different temperatures and with additional NaCl and carbon sources. Certain additional carbon sources improve the growth of Bacillus sp. JY35. However, this did not increase PBAT film degradation. Time-dependent PBAT film degradation rates were measured during three weeks of cultivation, after which the strain achieved almost 50% degradation. Additionally, various bioplastics were applied to solid cultures to confirm the biodegradation range of Bacillus sp. JY35, which can degrade not only PBAT but also PBS, PCL, PLA, PHB, P(3HB-co-4HB), P(3HB-co-3HV), P(3HB-co-3HHx), and P(3HB-co-3HV-co-3HHx), suggesting its usability as a superior bioplastic degrader.


Subject(s)
Bacillus , Adipates/chemistry , Alkenes , Carbon , Phthalic Acids , Polyesters , Sewage , Wastewater
16.
Molecules ; 26(19)2021 Oct 01.
Article in English | MEDLINE | ID: mdl-34641507

ABSTRACT

Hyaluronic acid (HA)-based hydrogels are very commonly applied as cell carriers for different approaches in regenerative medicine. HA itself is a well-studied biomolecule that originates from the physiological extracellular matrix (ECM) of mammalians and, due to its acidic polysaccharide structure, offers many different possibilities for suitable chemical modifications which are necessary to control, for example, network formation. Most of these chemical modifications are performed using the free acid function of the polymer and, additionally, lead to an undesirable breakdown of the biopolymer's backbone. An alternative modification of the vicinal diol of the glucuronic acid is oxidation with sodium periodate to generate dialdehydes via a ring opening mechanism that can subsequently be further modified or crosslinked via Schiff base chemistry. Since this oxidation causes a structural destruction of the polysaccharide backbone, it was our intention to study a novel synthesis protocol frequently applied to selectively oxidize the C6 hydroxyl group of saccharides. On the basis of this TEMPO/TCC oxidation, we studied an alternative hydrogel platform based on oxidized HA crosslinked using adipic acid dihydrazide as the crosslinker.


Subject(s)
Cyclic N-Oxides/chemistry , Hyaluronic Acid/chemistry , Hydrogels/chemistry , Mesenchymal Stem Cells/cytology , Adipates/chemistry , Cell Differentiation , Cell Survival , Chondrogenesis , Cross-Linking Reagents/chemistry , Elastic Modulus , Humans , Hyaluronan Receptors/metabolism , Hyaluronic Acid/metabolism , Oxidation-Reduction , Schiff Bases/chemistry , Surface Plasmon Resonance
17.
Molecules ; 26(16)2021 Aug 10.
Article in English | MEDLINE | ID: mdl-34443422

ABSTRACT

A significant increase in the production of plastic materials and the expansion of their areas of application contributed to the accumulation of a large amount of waste of polymeric materials. Most of the polymer composition is made up of plasticizers. Phthalate plasticizers have been recognized as potentially hazardous to humans and the environment due to the long period of their biodegradation and the formation of persistent toxic metabolites. It is known that the industrial plasticizer dioctyl adipate is characterized by reduced toxicity and a short biodegradation period. The paper describes the synthesis of a number of new asymmetric esters based on adipic acid and ethoxylated butanol by azeotropic esterification. The receipt of the products was confirmed by IR spectra. The physicochemical properties of the synthesized compounds were investigated. The glass transition temperatures of PVC composites plasticized with alkyl butoxyethyl adipates were determined using DSC analysis. The ecological safety of esters was assessed by the phytotesting method. Samples of adipates were tested for fungal resistance, and the process of their biodegradation in soil was also studied. It is shown that the synthesized esters have good plasticizing properties and are environmentally safe. When utilized under natural conditions, they can serve as a potential source of carbon for soil microorganisms and do not form stable toxic metabolites; therefore, they are not able to accumulate in nature; when the plasticizers under study are disposed of in the soil, toxic substances do not enter.


Subject(s)
Adipates/toxicity , Ecotoxicology , Ethanol/chemistry , Plasticizers/toxicity , Adipates/chemical synthesis , Adipates/chemistry , Biodegradation, Environmental , Calorimetry, Differential Scanning , Ethanol/chemical synthesis , Fungi/drug effects , Glass/chemistry , Lepidium/drug effects , Polyvinyl Chloride/chemistry , Raphanus/drug effects , Soil , Spectrophotometry, Infrared , Transition Temperature
18.
Molecules ; 26(13)2021 Jul 01.
Article in English | MEDLINE | ID: mdl-34279375

ABSTRACT

Infection is the major reason that people die from burns; however, traditional medical dressings such as gauze cannot restrain bacterial growth and enhance the healing process. Herein, an organic- and inorganic-base hydrogel with antibacterial activities was designed and prepared to treat burn wounds. Oxidized dextran (ODex) and adipic dihydrazide grafted hyaluronic acid (HA-ADH) were prepared, mixed with quaternized chitosan (HACC) and silver nanoparticles to fabricate Ag@ODex/HA-ADH/HACC hydrogel. The hydrogel, composed of nature biomaterials, has a good cytocompatibility and biodegradability. Moreover, the hydrogel has an excellent antibacterial ability and presents fast healing for burn wounds compared with commercial Ag dressings. The Ag@ODex/HA-ADH/HACC hydrogel will be a promising wound dressing to repair burn wounds and will significantly decrease the possibility of bacterial infection.


Subject(s)
Anti-Bacterial Agents/chemistry , Burns/therapy , Chitosan/analogs & derivatives , Hydrogels/chemistry , Metal Nanoparticles/chemistry , Wound Healing , Adipates/chemistry , Animals , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/therapeutic use , Bandages , Burns/drug therapy , Cell Line , Dextrans/chemistry , Hydrogels/pharmacology , Hydrogels/therapeutic use , Male , Mice , Pseudomonas aeruginosa/drug effects , Rats , Rats, Sprague-Dawley , Silver/chemistry , Staphylococcus aureus/drug effects
19.
Carbohydr Polym ; 267: 118193, 2021 Sep 01.
Article in English | MEDLINE | ID: mdl-34119160

ABSTRACT

Most polysaccharides used in polysaccharide-based block copolymers are attached to the second block through the reducing end, due to the few and highly polysaccharide specific non-reducing end (NRE) functionalisation methods available. Chitin oligomers, prepared by nitrous acid degradation of chitosan (AnM) can, however, be selectively oxidised by periodate since they only possess a single vicinal diol in the NRE residue. Here, we show that both aldehydes formed after oxidation are highly reactive towards bifunctional oxyamines and hydrazide linkers. Sub-stochiometric amounts of linkers resulted in conjugation of AnM oligomers through both chain termini to yield a discrete distribution of 'polymerised' oligomers. Such chitin-based block polymers were, in contrast to chitins of the same chain lengths, water-soluble. Oxidised AnM oligomers, functionalised at both termini can also enable the preparation of more complex block polysaccharides such as ABA- or ABC-type.


Subject(s)
Chitin/chemistry , Periodic Acid/chemistry , Water/chemistry , Adipates/chemistry , Aldehydes/chemical synthesis , Aldehydes/chemistry , Carbohydrate Sequence , Chitin/chemical synthesis , Hydroxylamines/chemistry , Mannose/analogs & derivatives , Mannose/chemistry , Oxidation-Reduction , Solubility
20.
J Mol Model ; 27(4): 113, 2021 Mar 25.
Article in English | MEDLINE | ID: mdl-33765215

ABSTRACT

Drug delivery clusters based on nanocages recently have been the most capable to study. Adipic acid (ADPA) interaction mechanism over nanocages of X(Al/B)12Y(N/P)12 was investigated. We analyzed various electronic, chemical, and spectroscopic properties with nanocages of the adsorbed ADPA molecule. Adsorption energies were calculated to study the adsorption of ADPA with nanocages. Raman enhanced surface scattering is used to track the drug as an effective approach to vibrational spectroscopy. Detection of the drug has been investigated using the SERS properties of nanocages. Title drug acts as a donor of electrons and adsorbs at the electrophilic site of nanocages. Variations in chemical descriptors to recognize the sensing property of ADPA-nanocages are also noted. Analysis of various properties explains enhancement which makes it possible to detect the drug in other products. • Interaction of adipic acid with fullerene-like metal nanocages • Enhancement of spectral properties • Changes in charge transfer values in nanocage-drug system • Docking studies identify the drug delivery property.


Subject(s)
Adipates/chemistry , Density Functional Theory , Nanostructures/chemistry , Adsorption , Computational Chemistry
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