Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Functionalization of polyethylene with hydrolytically-stable ester groups.

ABSTRACT: Low-density (LD) and high-density polyethylene (HDPE), recycled or not, incorporates up to 7 wt% of ester groups after reacting either with ethyl diazoacetate (EDA) under catalytic and solvent free-reaction conditions, or with maleic anhydride (MA) and acrylates (AC) under catalytic radical conditions. The resulting upcycled polyethylene esters are hydrolytically stable at extreme pH (0-14) and can be further transformed into carboxylic acids, carboxylates, other esters and amides.

SUBMITTER: Hervas-Arnandis S

PROVIDER: S-EPMC10413336 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Functionalization of polyethylene with hydrolytically-stable ester groups.

Hervàs-Arnandis Susi S Palomar-de Lucas Brenda B Bilanin Cristina C Mingueza-Verdejo Paloma P Viciano Mónica M Oliver-Meseguer Judit J Leyva-Pérez Antonio A

RSC advances 20230810 34

Low-density (LD) and high-density polyethylene (HDPE), recycled or not, incorporates up to 7 wt% of ester groups after reacting either with ethyl diazoacetate (EDA) under catalytic and solvent free-reaction conditions, or with maleic anhydride (MA) and acrylates (AC) under catalytic radical conditions. The resulting upcycled polyethylene esters are hydrolytically stable at extreme pH (0-14) and can be further transformed into carboxylic acids, carboxylates, other esters and amides. ...[more]

PMID: 37577098

Similar Datasets

Hydrolytically Degradable Zwitterionic Polyphosphazene Containing HEPES Moieties as Side Groups.

Project description:Zwitterionic polymers, ampholytic macromolecules containing ionic moieties of opposite sign on the same pendant groups, exhibit strong protein-repulsive properties and an inherent biological inertness. For that reason, these highly hydrated inner salt macromolecules have emerged as some of the most viable alternatives to poly(ethylene glycol) (PEG), a gold standard in enabling stealth behavior in life science applications. However, the structural diversity of polymer zwitterions remains limited, and currently available macromolecules do not possess an intrinsic ability to undergo hydrolytical degradation, an important prerequisite for use in drug delivery applications. The present paper reports on the synthesis of a zwitterionic polymer, a multimerized form (two thousand copies), of a biologically benign buffering agent, HEPES, which is covalently assembled on a polyphosphazene backbone. The polymer exhibits typical polyzwitterionic solution behavior, an environmentally dependent hydrolytic degradation pattern, and excellent in vitro compatibility, features that highlight its potential utility for life science applications.

| S-EPMC11480972 | biostudies-literature

Nonswelling and Hydrolytically Stable Hydrogels Uncover Cellular Mechanosensing in 3D.

Project description:While matrix stiffness regulates cell behavior on 2D substrates, recent studies using synthetic hydrogels have suggested that in 3D environments, cell behavior is primarily impacted by matrix degradability, independent of stiffness. However, these studies did not consider the potential impact of other confounding matrix parameters that typically covary with changes in stiffness, particularly, hydrogel swelling and hydrolytic stability, which may explain the previously observed distinctions in cell response in 2D versus 3D settings. To investigate how cells sense matrix stiffness in 3D environments, a nonswelling, hydrolytically stable, linearly elastic synthetic hydrogel model is developed in which matrix stiffness and degradability can be tuned independently. It is found that matrix degradability regulates cell spreading kinetics, while matrix stiffness dictates the final spread area once cells achieve equilibrium spreading. Importantly, the differentiation of human mesenchymal stromal cells toward adipocytes or osteoblasts is regulated by the spread state of progenitor cells upon initiating differentiation. These studies uncover matrix stiffness as a major regulator of cell function not just in 2D, but also in 3D environments, and identify matrix degradability as a critical microenvironmental feature in 3D that in conjunction with matrix stiffness dictates cell spreading, cytoskeletal state, and stem cell differentiation outcomes.

| S-EPMC9036035 | biostudies-literature

Identification of hydrolytically stable and selective P2Y(1) receptor agonists.

Project description:P2Y nucleotide receptors (P2YRs) are attractive pharmaceutical targets. Most P2YR agonists proposed as drugs consist of a nucleotide scaffold, but their use is limited due to their chemical and enzymatic instabilities. To identify drug candidates, we developed non-hydrolyzable P2YR agonists. We synthesized ATP-beta,gamma-CH(2) analogues 2-4, and evaluated their chemical and metabolic stabilities and activities at P2Y(1,2,4,6) receptors. Analogues 2-4 exhibited t(1/2) values of 14.5-65 h in gastric juice pH. They were completely resistant to alkaline phosphatase for 30 min at 37 degrees C and slowly hydrolyzed in human blood serum (t(1/2) 12.7-71.9 h). In comparison to ATP, analogues 2-4 were barely hydrolyzed by nucleoside triphosphate diphosphohydrolases, NTPDase1,2,3,8 (< 8% hydrolysis), and nucleotide pyrophosphatases, NPP1,3 (< or = 10% hydrolysis). Analogues 2 and 4B were selective agonists of the P2Y(1)R with EC(50)s of 0.08 and 17.2 microM, respectively. These features make analogues 2 and 4B potential therapeutic agents for health disorders involving the P2Y(1)R.

| S-EPMC4354951 | biostudies-literature

Controlled release of an anthrax toxin-neutralizing antibody from hydrolytically degradable polyethylene glycol hydrogels.

Project description:In this study, hydrophilic and hydrolytically degradable poly (ethylene glycol) (PEG) hydrogels were formed via Michael-type addition and employed for sustained delivery of a monoclonal antibody against the protective antigen of anthrax. Taking advantage of the PEG-induced precipitation of the antibody, burst release from the matrix was avoided. These hydrogels were able to release active antibodies in a controlled manner from 14 days to as long as 56 days in vitro by varying the polymer architectures and molecular weights of the precursors. Analysis of the secondary and tertiary structure and the in vitro activity of the released antibody showed that the encapsulation and release did not affect the protein conformation or functionality. The results suggest the promise for developing PEG-based carriers for sustained release of therapeutic antibodies against toxins in various applications.

| S-EPMC4933017 | biostudies-literature

Thermodynamically Stable Functionalization of Microporous Aromatic Frameworks with Sulfonic Acid Groups by Inserting Methylene Spacers.

Project description:Porous aromatic frameworks (PAFs) are an auspicious class of materials that allow for the introduction of sulfonic acid groups at the aromatic core units by post-synthetic modification. This makes PAFs promising for proton-exchange materials. However, the limited thermal stability of sulfonic acid groups attached to aromatic cores prevents high-temperature applications. Here, we present a framework based on PAF-303 where the acid groups were added as methylene sulfonic acid side chains in a two-step post-synthetic route (SMPAF-303) via the intermediate chloromethylene PAF (ClMPAF-303). Elemental analysis, NMR spectroscopy, electrochemical impedance spectroscopy and X-ray photoelectron spectroscopy were used to characterize both frameworks and corroborate the successful attachment of the side chains. The resulting framework SMPAF-303 features high thermal stability and an ion-exchange capacity of about 1.7 mequiv g-1. The proton conductivity depends strongly on the adsorbed water level. It reaches from about 10-7 S cm-1 for 33% RH to about 10-1 S cm-1 for 100% RH. We attribute the strong change to a locally alternating polarity of the inner surfaces. The latter introduces bottleneck effects for the water molecule and oxonium ion diffusion at lower relative humidities, due to electrolyte clustering. When the pores are completely filled with water, these bottlenecks vanish, leading to an unhindered electrolyte diffusion through the framework, explaining the conductivity rise.

| S-EPMC11013227 | biostudies-literature

Improve Dentin Bonding Performance Using a Hydrolytically Stable, Ether-Based Primer.

Project description:The objective of this study is to replace a traditional methacrylate-based primer (glycine, N-(2-hydroxy-3-(2-methyl-1-oxo-2-propenyl)propyl)-N-(4-methylphenyl) monosodium salt, NTG-GMA) with a hydrolytically stable ether-based primer (glycine, N-2-hydroxy-3-(4-vinylbenzyloxy)-propyl-N-(4-methylphenyl), monosodium salt, NTG-VBGE). The performance and durability of bonding composites to detin of two primers combined with methacrylate-based or ether-based adhesives were evaluated using shear bond strength (SBS) and micro-tensile bond strength (μTBS) combined with thermal cycling. The hydrolysis resistance of NTG-VBGE against hydrolysis was tested by challenging primed hydroxyapatite crystals with an esterase. The hydrophilicity of the primers and the resin spreading kinetics of adhesives on primed dentin were characterized by water contact angle measurements. The new primer NTG-VBGE was found to be compatible with both methacrylate-based adhesives and ether-based adhesives. The highest μTBS values were found in the test group of NTG-VBGE and ether-based adhesive, which was consistent with the resin spreading kinetics results. The more hydrophobic and hydrolytically stable primer/adhesive achieved improved dentin infiltration and bonding strength, suggesting significant potential for further developing dental restorative materials with extended service life.

| S-EPMC9501844 | biostudies-literature

Hydrolytically Stable Maleimide-End-Functionalized Polymers for Site-Specific Protein Conjugation.

Project description:Site-specific conjugation to cysteines of proteins often uses ester groups to link maleimide or alkene groups to polymers. However, the ester group is susceptible to hydrolysis, potentially losing the benefits gained through bioconjugation. Here, we present a simple conjugation strategy that utilizes the amide bond stability of traditional 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide/N-hydroxysuccinimide coupling while introducing site specificity. Hydrolytically stable maleimide-end-functionalized polymers for site-specific conjugation to free cysteines of proteins were synthesized using reversible addition-fragmentation chain-transfer (RAFT) polymerization. The alpha terminus of the polymers was amidated with a furan-protected aminoethyl maleimide using carbodiimide-based chemistry. Finally, the maleimide was exposed by a retro Diels-Alder reaction to yield the maleimide group, allowing for thiol-maleimide click chemistry for bioconjugation. A thermophilic cellulase from Fervidobacterium nodosum (FnCel5a) was conjugated using various strategies, including random 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)/N-hydroxysuccinimide (NHS) coupling, site-specific hydroxyethyl maleimide (HEMI) end-functionalized coupling, hydroxyethyl acrylate (HEA) end-functionalized coupling, and amidoethyl maleimide (AEMI) end-functionalized coupling. Only the polymers conjugated by EDC and AEMI remained conjugated a week after attachment. This indicates that hydrolytically stable amide-based maleimides are an important bioconjugation strategy for conjugates that require long-term stability, while esters are better suited for systems that require debonding of polymers over time.

| S-EPMC9099401 | biostudies-literature

NMR Characterization of Polyethylene Glycol Conjugates for Nanoparticle Functionalization.

Project description:The molecular weight, purity, and functionalization of polyethylene glycols are often characterized by 1H NMR spectroscopy. Oft-forgotten, the typical 1H NMR pulse sequence is not 13C decoupled. Hence, for large polymers, the 13C coupled 1H peaks arising from the repeating units have integrations comparable to that of the 1H of the terminal groups. Ignoring this coupling leads to erroneous assignments. Once correctly assigned, these 13C coupled 1H peaks can be used to determine both the molecular weight of the polymer and the efficacy of conjugation of a terminal moiety more accurately than the uncoupled 1H of the repeating unit.

| S-EPMC9893458 | biostudies-literature

Hydrolytically stable foamed HKUST-1@CMC composites realize high-efficient separation of U(VI).

Project description:HKUST-1@CMC (HK@CMC) composites that show good acid and alkali resistance and radiation resistance were successfully synthesized by introducing carboxymethyl cellulose (CMC) onto the surface of HKUST-1 using a foaming strategy. For the first time, the composites were explored as efficient adsorbents for U(VI) trapping from aqueous solution, with encouraging results of large adsorption capacity, fast adsorption kinetics, and desirable selectivity toward U(VI) over a series of competing ions. More importantly, a hybrid derivative film was successfully prepared for the dynamic adsorption of U(VI). The results show that ∼90% U(VI) can be removed when 45 mg L-1 U(VI) was passed through the film one time, and the removal percentage is still more than 80% even after four adsorption-desorption cycles, ranking one of the most practical U(VI) scavengers. This work offers new clues for application of the Metal-organic-framework-based materials in the separation of radionuclides from wastewater.

| S-EPMC8405966 | biostudies-literature

?-Phenylalanine Ester Synthesis from Stable ?-Keto Ester Substrate Using Engineered ?-Transaminases.

Project description:The successful synthesis of chiral amines from ketones using ?-transaminases has been shown in many cases in the last two decades. In contrast, the amination of ?-keto acids is a special and relatively new challenge, as they decompose easily in aqueous solution. To avoid this, transamination of the more stable ?-keto esters would be an interesting alternative. For this reason, ?-transaminases were tested in this study, which enabled the transamination of the ?-keto ester substrate ethyl benzoylacetate. Therefore, a ?-transaminase library was screened using a coloring o-xylylenediamine assay. The ?-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-?-phenylalanine esters. This alternative approach resulted in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-?-phenylalanine ethyl ester was isolated by performing a semi-preparative synthesis.

| S-EPMC6100204 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data