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Biomacromolecules Sep 2022A small library of degradable polyester-like glycopolymers was successfully prepared by the combination of radical ring-opening copolymerization of...
A small library of degradable polyester-like glycopolymers was successfully prepared by the combination of radical ring-opening copolymerization of 2-methylene-1,3-dioxepane as a cyclic ketene acetal (CKA) with vinyl ether (VE) derivatives and a Pd-catalyzed thioglycoconjugation. The resulting thioglycopolymers were formulated into self-stabilized thioglyconanoparticles, which were stable up to 4 months and were enzymatically degraded. Nanoparticles and their degradation products exhibited a good cytocompatibility on two healthy cell lines. Interactions between thioglyconanoparticles and lectins were investigated and highlighted the presence of both specific carbohydrate/lectin interactions and nonspecific hydrophobic interactions. Fluorescent thioglyconanoparticles were also prepared either by encapsulation of Nile red or by the functionalization of the polymer backbone with rhodamine B. Such nanoparticles were used to prove the cell internalization of the thioglyconanoparticles by lung adenocarcinoma (A549) cells, which underlined the great potential of P(CKA--VE) copolymers for biomedical applications.
Topics: Acetals; Ethers, Cyclic; Nanoparticles; Polymerization; Polymers
PubMed: 35971824
DOI: 10.1021/acs.biomac.2c00851 -
International Journal of Molecular... Jan 2023Short-chain fatty acids as well as their bacterial producers are of increasing interest in inflammatory bowel diseases. Although less studied compared to butyrate,...
High Acetate Concentration Protects Intestinal Barrier and Exerts Anti-Inflammatory Effects in Organoid-Derived Epithelial Monolayer Cultures from Patients with Ulcerative Colitis.
Short-chain fatty acids as well as their bacterial producers are of increasing interest in inflammatory bowel diseases. Although less studied compared to butyrate, acetate might also be of interest as it may be less toxic to epithelial cells, stimulate butyrate-producing bacteria by cross-feeding, and have anti-inflammatory and barrier-protective properties. Moreover, one of the causative factors of the probiotic potency of var. is thought to be its high acetate production. Therefore, the objective was to preclinically assess the effects of high acetate concentrations on inflammation and barrier integrity in organoid-based monolayer cultures from ulcerative colitis patients. Confluent organoid-derived colonic epithelial monolayers ( = 10) were exposed to basolateral inflammatory stimulation or control medium. After 24 h, high acetate or control medium was administered apically for an additional 48 h. Changes in TEER were measured after 48 h. Expression levels of barrier genes and inflammatory markers were determined by qPCR. Pro-inflammatory proteins in the supernatant were quantified using the MSD platform. Increased epithelial resistance was observed with high acetate administration in both inflamed and non-inflamed conditions, together with decreased expression levels of IL8 and TNFα and CLDN1. Upon high acetate administration to inflamed monolayers, upregulation of HIF1α, MUC2, and MKI67, and a decrease of the majority of pro-inflammatory cytokines was observed. In our patient-derived human epithelial cell culture model, a protective effect of high acetate administration on epithelial resistance, barrier gene expression, and inflammatory protein production was observed. These findings open up new possibilities for acetate-mediated management of barrier defects and inflammation in IBD.
Topics: Humans; Colitis, Ulcerative; Intestinal Mucosa; Inflammation; Butyrates; Acetates; Organoids; Colitis
PubMed: 36614212
DOI: 10.3390/ijms24010768 -
Organic & Biomolecular Chemistry Aug 2022In this report, we demonstrate that visible light photoactivation of 6-bromo-2-naphthol facilitates the photoacid-catalyzed acetalization of carbonyls with alcohols. We...
In this report, we demonstrate that visible light photoactivation of 6-bromo-2-naphthol facilitates the photoacid-catalyzed acetalization of carbonyls with alcohols. We also demonstrate that 2-naphthol when coupled to a photosensitizer provides acetals from electron-deficient aldehydes. In addition, the S excited state p for 6-bromo-2-naphthol in water was determined and shown to have increased excited-state acidity relative to 2-naphthol.
Topics: Acetals; Alcohols; Aldehydes; Catalysis; Molecular Structure
PubMed: 35876112
DOI: 10.1039/d2ob00435f -
Journal of Agricultural and Food... Feb 2023The use of skin repellents against hematophagous mosquitoes is an important personal protection practice wherever these insects are abundant and where they are vectors...
The use of skin repellents against hematophagous mosquitoes is an important personal protection practice wherever these insects are abundant and where they are vectors of diseases. DEET and Icaridin are the major synthetic insect repellents in commercial formulations and are considered the most effective. Here, we tested against the mosquito several cyclic hydroxyacetals synthesized by acetalization of commercially available aliphatic carbonyl compounds (ranging from C3 to C15) with either glycerol, 1,1,1-trismethyloletane, or 1,1,1-trismethylolpropane and compared their efficacy with commercial repellents. We found that several hydroxyacetals were comparable with DEET and Icaridin both in terms of the required dose and repellence duration, while a few performed better. For those most active, toxicity was investigated, finding that a few of them were less cytotoxic than DEET and less prone to permeate through cell layers. Therefore, such results indicate that novel safe mosquito repellents could be developed among cyclic hydroxyacetals.
Topics: Animals; Insect Repellents; DEET; Acetals; Mosquito Vectors; Aedes
PubMed: 36649540
DOI: 10.1021/acs.jafc.2c05537 -
Bioanalysis Mar 2021The acetate ion has important physiological functions and important therapeutic applications. A rapid LC-MS/MS method is described to measure acetate ions in human...
The acetate ion has important physiological functions and important therapeutic applications. A rapid LC-MS/MS method is described to measure acetate ions in human plasma without chemical derivatization. A 200 μl sample was spiked with the internal standard 1,2-C-acetate and proteins precipitated with trichloroacetic acid. The supernatant was recovered and separated under acidic conditions on a C18-column. The eluent was alkalinized by post-column infusion of methanolic ammonium hydroxide. Acetate ions were monitored on a low resolution mass spectrometer in negative ion mode. Method was validated for accuracy and precision with a lower limit of quantitation of 9.7 μM and linear dynamic range up to 339.6 μM. The method is open for analytical improvement and adapts with metabolomic and pharmacometabolomic studies on chemicals of similar nature.
Topics: Acetates; Biological Assay; Chromatography, Liquid; Humans; Tandem Mass Spectrometry
PubMed: 33661702
DOI: 10.4155/bio-2020-0294 -
Molecular Biology of the Cell Jun 2023The short-chain fatty acid metabolite acetyl-coenzyme A (acetyl-CoA) has emerged as a major signal transducer that can broadly affect cell fate and function, at least...
The short-chain fatty acid metabolite acetyl-coenzyme A (acetyl-CoA) has emerged as a major signal transducer that can broadly affect cell fate and function, at least partly by influencing acetylation of key proteins. The mechanism by which acetyl-CoA regulates CD4 T-cell fate determination remains poorly understood. Herein, we report that acetate modulates glyceraldehyde-3-phosphate dehydrogenase (GAPDH) acetylation and CD4 T helper 1 (Th1) cell differentiation by altering acetyl-CoA levels. Our transcriptome profiling shows that acetate is a robust positive regulator of CD4 T-cell gene expression typical of glycolysis. We further show that acetate potentiates GAPDH activity, aerobic glycolysis, and Th1 polarization through regulation of GAPDH acetylation levels. This acetate-dependent GAPDH acetylation occurs in a dose- and time-dependent manner, while decreasing acetyl-CoA levels by fatty acid oxidation inhibition results in a decline in acetyl-GAPDH levels. Thus, acetate functions as a potent metabolic regulator in CD4 T-cells by promoting GAPDH acetylation and Th1 cell fate decision.
Topics: Acetyl Coenzyme A; Acetylation; Cell Differentiation; Acetates
PubMed: 37133968
DOI: 10.1091/mbc.E23-02-0070 -
Bioresource Technology May 2016The process of lignocellulosic biomass routinely produces a stream that contains sugars plus various amounts of acetic acid. As acetate is known to inhibit the culture...
The process of lignocellulosic biomass routinely produces a stream that contains sugars plus various amounts of acetic acid. As acetate is known to inhibit the culture of microorganisms including oleaginous yeasts, little attention has been paid to explore lipid production on mixtures of acetate and sugars. Here we demonstrated that the yeast Cryptococcus curvatus can effectively co-ferment acetate and sugars for lipid production. When mixtures of acetate and glucose were applied, C. curvatus consumed both substrates simultaneously. Similar phenomena were also observed for acetate and xylose mixtures, as well as acetate-rich corn stover hydrolysates. More interestingly, the replacement of sugar with equal amount of acetate as carbon source afforded higher lipid titre and lipid content. The lipid products had fatty acid compositional profiles similar to those of cocoa butter, suggesting their potential for high value-added fats and biodiesel production. This co-fermentation strategy should facilitate lipid production technology from lignocelluloses.
Topics: Acetates; Acetic Acid; Biofuels; Biomass; Carbohydrates; Carbon; Cellulase; Cryptococcus; Fatty Acids; Fermentation; Glucose; Glycerol; Hydrogen-Ion Concentration; Lignin; Lipids; Saccharomyces cerevisiae; Xylose; Zea mays
PubMed: 26874438
DOI: 10.1016/j.biortech.2016.01.122 -
Bioresource Technology Oct 2022Anaerobic digestion is a complex process, involving various microorganism groups and, consequently, several reactions. An easy-to-use protocol for the rate-limiting step...
Anaerobic digestion is a complex process, involving various microorganism groups and, consequently, several reactions. An easy-to-use protocol for the rate-limiting step determination of the process is proposed. The hydrogen production, acetate production, and acetate consumption rates can be calculated, according to a structured algorithm. During the rate limiting step determination, several compounds (biopolymer and monomer representatives, as well as sodium acetate) were used, combined or not with the substrate, to draw the corresponding conclusions. Three substrates were tested, characterized by specific organic compound groups (carbohydrates, proteins, and fats). All three substrates followed the acetate-consuming pathway for the organic matter conversion to methane. In this study, the rate-limiting step for the pathway of acetate consumption was acetate production. Determining the rate-limiting step through the proposed protocol can point to the appropriate actions needed to boost methane production, like substrate pretreatment, using an acidogenic reactor, or checking for the presence of inhibitors.
Topics: Acetates; Anaerobiosis; Bioreactors; Methane
PubMed: 35872279
DOI: 10.1016/j.biortech.2022.127660 -
Fitoterapia Jun 2020Four undescribed oxylipin vanillyl acetals with four stereogenic carbons were isolated from the herbs of Solanum lyratum. A comprehensive set of spectroscopic methods...
Four undescribed oxylipin vanillyl acetals with four stereogenic carbons were isolated from the herbs of Solanum lyratum. A comprehensive set of spectroscopic methods were used to elucidate the structures and relative configurations of 1-4. The absolute configurations of the naturally occurring compounds are assigned as 7S, 9'S, 10'S, 11'R at the site of six-membered cyclic acetal attachment by electronic circular dichroism (ECD) calculations and the modified Mosher's method. Compounds 1 and 3 displayed moderate selective inhibition against Hep3B and HepG2 cells, respectively. Further Annexin V-FITC/PI staining assay revealed that 1 and 3 might have inhibitory effects on hepatoma cells through induction of apoptosis.
Topics: Acetals; Antineoplastic Agents, Phytogenic; Apoptosis; China; Hep G2 Cells; Humans; Molecular Structure; Oxylipins; Phytochemicals; Solanum
PubMed: 32199958
DOI: 10.1016/j.fitote.2020.104559 -
Bioprocess and Biosystems Engineering Jan 2021In this study, simultaneous removal of ammonium plus phenol could be achieved by Alcaligenes faecalis strain WY-01 with the addition of acetate, although acetate delayed...
In this study, simultaneous removal of ammonium plus phenol could be achieved by Alcaligenes faecalis strain WY-01 with the addition of acetate, although acetate delayed the phenol degradation, probably due to the delayed expression of phenol hydroxylase gene under the presence of acetate. Moreover, the successful expression of key enzyme genes in strain WY-01 provided some evidence to illustrate its metabolic pathways of ammonium and phenol under aerobic conditions. Furthermore, SEM was used to clarify the role of acetate in resisting phenol toxicity, and these results demonstrated that strain WY-01 has the ability to form cell flocs when sodium acetate is used as co-substrate for a high concentration of phenol, and these flocs could protect cells against the toxicity of phenol, further enhancing phenol degradation in a high concentration of phenol. All these will provide further insights into the efficacy of strain WY-01 for treating wastewater cocontaminated by ammonium and phenol.
Topics: Acetates; Alcaligenes faecalis; Ammonium Compounds; Phenol; Waste Disposal, Fluid; Water Purification
PubMed: 32748276
DOI: 10.1007/s00449-020-02416-3