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Annual Review of Biochemistry Jun 2021Sulfonates include diverse natural products and anthropogenic chemicals and are widespread in the environment. Many bacteria can degrade sulfonates and obtain sulfur,... (Review)
Review
Sulfonates include diverse natural products and anthropogenic chemicals and are widespread in the environment. Many bacteria can degrade sulfonates and obtain sulfur, carbon, and energy for growth, playing important roles in the biogeochemical sulfur cycle. Cleavage of the inert sulfonate C-S bond involves a variety of enzymes, cofactors, and oxygen-dependent and oxygen-independent catalytic mechanisms. Sulfonate degradation by strictly anaerobic bacteria was recently found to involve C-S bond cleavage through O-sensitive free radical chemistry, catalyzed by glycyl radical enzymes (GREs). The associated discoveries of new enzymes and metabolic pathways for sulfonate metabolism in diverse anaerobic bacteria have enriched our understanding of sulfonate chemistry in the anaerobic biosphere. An anaerobic environment of particular interest is the human gut microbiome, where sulfonate degradation by sulfate- and sulfite-reducing bacteria (SSRB) produces HS, a process linked to certain chronic diseases and conditions.
Topics: Acetyltransferases; Alkanesulfonates; Anaerobiosis; Bacteria; Carbon-Carbon Lyases; Gastrointestinal Microbiome; Glycine; Humans; Hydrogen Sulfide; Isethionic Acid; Microbiota; Sulfonic Acids; Taurine
PubMed: 33823652
DOI: 10.1146/annurev-biochem-080120-024103 -
European Journal of Medicinal Chemistry Apr 2022Vinyl sulfone with electrophilic character is not only a versatile building block for various organic transformations but also is a key structural unit in a large number... (Review)
Review
Vinyl sulfone with electrophilic character is not only a versatile building block for various organic transformations but also is a key structural unit in a large number of biologically active molecules. In the recent decades vinyl sulfone has attracted much attention due to its potential as a privileged structural motif in medicinal chemistry for the drug discovery and development. It can be found in the chemical structure of many leads and drug candidates such as Rigosertib, Recilisib, K11777, WRR-483 and BAY 11-7085. The vinyl sulfone motif has been especially used in the design of chemotherapeutics and neuroprotective as well as radioprotective agents. In this review, we have described design, chemical structures, biological properties and related mechanism of actions, and structure activity relationship (SAR) study of vinyl sulfone-based compounds.
Topics: Chemistry, Pharmaceutical; Drug Design; Sulfones; Vinyl Compounds
PubMed: 35305462
DOI: 10.1016/j.ejmech.2022.114255 -
Archives of Toxicology May 2023Cardiovascular disease (CVD) poses the leading threats to human health and life, and their occurrence and severity are associated with exposure to environmental... (Review)
Review
Cardiovascular disease (CVD) poses the leading threats to human health and life, and their occurrence and severity are associated with exposure to environmental pollutants. Per- and polyfluoroalkyl substances (PFAS), a group of widely used industrial chemicals, are characterized by persistence, long-distance migration, bioaccumulation, and toxicity. Some PFAS, particularly perfluorooctane sulfonic acid (PFOS), perfluorooctanoic acid (PFOA) and perfluorohexanesulfonic acid (PFHxS), have been banned, leaving only legacy exposure to the environment and human body, while a number of novel PFAS alternatives have emerged and raised concerns, such as polyfluoroalkyl ether sulfonic and carboxylic acid (PFESA and PFECA) and sodium p-perfluorous nonenoxybenzene sulfonate (OBS). Overall, this review systematically elucidated the adverse cardiovascular (CV) effects of legacy and emerging PFAS, emphasized the dose/concentration-dependent, time-dependent, carbon chain length-dependent, sex-specific, and coexposure effects, and discussed the underlying mechanisms and possible prevention and treatment. Extensive epidemiological and laboratory evidence suggests that accumulated serum levels of legacy PFAS possibly contribute to an increased risk of CVD and its subclinical course, such as cardiac toxicity, vascular disorder, hypertension, and dyslipidemia. The underlying biological mechanisms may include oxidative stress, signaling pathway disturbance, lipid metabolism disturbance, and so on. Various emerging alternatives to PFAS also play increasingly prominent toxic roles in CV outcomes that are milder, similar to, or more severe than legacy PFAS. Future research is recommended to conduct more in-depth CV toxicity assessments of legacy and emerging PFAS and explore more effective surveillance, prevention, and treatment strategies, accordingly.
Topics: Male; Female; Humans; Alkanesulfonic Acids; Alkanesulfonates; Environmental Pollutants; Fluorocarbons; Cardiovascular Diseases
PubMed: 36947184
DOI: 10.1007/s00204-023-03477-5 -
Journal of Agricultural and Food... Sep 2022The application of agrochemicals is critical to global food safety. Nowadays, environmentally friendly green agrochemicals are the trend in field crop protection. The... (Review)
Review
The application of agrochemicals is critical to global food safety. Nowadays, environmentally friendly green agrochemicals are the trend in field crop protection. The research and development of nematicides absorbed more attention as a typical representation of agrochemicals. This review describes the origin of recently commercialized nematicides, the application of bioisosterism and scaffold hopping in the discovery and optimization of agrochemicals, especially nematicides, and novel bioisosteric design strategies for the identification of fluensulfone analogues. Pesticide repurposing, high-throughput screening, computer-aided drug design, and incorporation of known pharmacophoric fragments have been the most successful approach for the discovery of new nematicides. As outlined, the strategies of bioisosteric replacements and scaffold hopping have been very successful approaches in the search for new nematicides for sustainable crop protection. In the exploration of novel fluensulfone analogues with nematicidal activity, bioisosteric replacement of sulfone by amide, chain extension by insertion of a methylene group, and reversal of the amide group have proven to be successful approaches and yielded new and highly active fluensulfone analogues. These attempts might result in compounds with an optimal balance of steric, hydrophobic, electronic, and hydrogen-bonding properties and contribute to deal with the complex problem during the research and development of new nematicides. Further ideas are also put forward to provide new approaches for the molecular design of nematicides.
Topics: Agrochemicals; Amides; Animals; Antinematodal Agents; Sulfones; Thiazoles; Tylenchoidea
PubMed: 35549340
DOI: 10.1021/acs.jafc.2c00785 -
International Journal of Molecular... Apr 2024Polymers stand out as promising materials extensively employed in biomedicine and biotechnology. Their versatile applications owe much to the field of tissue... (Review)
Review
Polymers stand out as promising materials extensively employed in biomedicine and biotechnology. Their versatile applications owe much to the field of tissue engineering, which seamlessly integrates materials engineering with medical science. In medicine, biomaterials serve as prototypes for organ development and as implants or scaffolds to facilitate body regeneration. With the growing demand for innovative solutions, synthetic and hybrid polymer materials, such as polyethersulfone, are gaining traction. This article offers a concise characterization of polyethersulfone followed by an exploration of its diverse applications in medical and biotechnological realms. It concludes by summarizing the significant roles of polyethersulfone in advancing both medicine and biotechnology, as outlined in the accompanying table.
Topics: Animals; Humans; Biocompatible Materials; Biotechnology; Polymers; Sulfones; Tissue Engineering; Tissue Scaffolds
PubMed: 38673817
DOI: 10.3390/ijms25084233 -
The Science of the Total Environment Nov 2021Following the global phase out of perfluorooctane sulfate (PFOS), chlorinated polyfluoroalkyl ether sulfonates (Cl-PFAESs) and p-perfluorous nonenoxybenzenesulfonate...
Following the global phase out of perfluorooctane sulfate (PFOS), chlorinated polyfluoroalkyl ether sulfonates (Cl-PFAESs) and p-perfluorous nonenoxybenzenesulfonate (PFNOBS) have emerged as novel PFOS substitutes. However, until now, limited data is available on their occurrence and environmental behaviors in the marine environment. Here, seawater and sediment samples were collected from East China Sea and analyzed for Cl-PFAESs, PFNOBS, and perfluoroalkyl acids (PFAAs; including their branched isomers) to investigate their concentrations, potential sources, and sediment-seawater partitioning behaviors. Perfluorooctanoate (PFOA) and PFOS were consistently the predominant PFAAs in seawaters and sediments. Branched PFOA and PFOS isomers were consistently much less frequently detected in sediments than that in seawaters. Linear PFOA contributed 92-95% of total PFOA in seawaters, suggesting the great contribution of telomerization PFOA. 6:2 Cl-PFAES was detected in all seawaters (concentration, 0.58-47 pg/L) and in the majority of sediments (
Topics: Alkanesulfonates; Alkanesulfonic Acids; Caprylates; China; Environmental Monitoring; Fluorocarbons; Seawater; Water Pollutants, Chemical
PubMed: 34311366
DOI: 10.1016/j.scitotenv.2021.149052 -
Environmental Science & Technology May 2022Perfluoroalkyl sulfonates (PFSAs), perfluoroalkyl carboxylates (PFCAs), and emerging alternatives and precursors of these compounds were determined in tissues of finless...
Perfluoroalkyl sulfonates (PFSAs), perfluoroalkyl carboxylates (PFCAs), and emerging alternatives and precursors of these compounds were determined in tissues of finless porpoise () collected from East China Sea in 2009-2010 and 2018-2019. The median hepatic concentrations of emerging poly- and perfluoroalkyl substances (PFASs), including 6:2 chlorinated polyfluorinated ether sulfonate (6:2 Cl-PFESA), 8:2 chlorinated polyfluorinated ether sulfonate (8:2 Cl-PFESA), 2,3,3,3-tetrafluoro-2-propanoate (HFPO-DA), and 4,8-dioxa-3-perfluorononanoate (ADONA) were 16.2, 2.16, < LOQ (limit of quantification) and < LOQ ng/g ww (wet weight), respectively. The concentrations of legacy substances, perfluorooctanesulfonate (PFOS), and perfluorooctanoate (PFOA), were 86.9 and 1.95 ng/g ww, respectively. The liver concentrations of 6:2 Cl-PFESA, HFPO-DA, and perfluorohexanesulfonate (PFHxS) increased with time between 2009-2010 and 2018-2019. Further, concentrations of PFOA showed a declining trend in finless porpoise, whereas PFOS and its precursor (i.e., perfluorooctane sulfonamide [FOSA]) showed an increasing trend with time between 2009-2010 and 2018-2019. Analysis of PFASs in nine different tissues/organs of finless porpoise (i.e., liver, heart, intestine, spleen, kidney, stomach, lung, muscle, and skin) revealed a similar distribution pattern between 6:2 Cl-PFESA and PFOS; however, the tissue distribution patterns differed between HFPO-DA and PFOA. The concentrations of PFAS alternatives in kidney were similar or lower than the prototype compounds PFOS and PFOA (i.e., 8:2 Cl-PFESA < 6:2 Cl-PFESA ≈ PFOS; HFPO-DA < PFOA), implying slow renal excretion of PFAS alternatives as that of legacy PFASs. The estimates of body burdens of PFASs in porpoises suggested comparable accumulation of PFAS alternatives and legacy PFSAs and PFCAs. This study provides novel information on temporal trends and tissue distribution of emerging PFASs in marine mammals in China.
Topics: Alkanesulfonates; Alkanesulfonic Acids; Animals; China; Ether; Ethers; Fluorocarbons; Porpoises
PubMed: 33851820
DOI: 10.1021/acs.est.1c00062 -
The Science of the Total Environment May 2024No study has examined the association between per- and polyfluoroalkyl substances (PFAS) exposure and chronic obstructive pulmonary disease (COPD) risk. This study aims...
BACKGROUND
No study has examined the association between per- and polyfluoroalkyl substances (PFAS) exposure and chronic obstructive pulmonary disease (COPD) risk. This study aims to explore this relationship.
METHODS
This study enrolled 4541 individuals who had available data on PFAS, COPD, and covariates from NHANES 2007-2018. Serum PFAS including perfluorohexane sulfonate (PFHxS), perfluorononanoic acid (PFNA), perfluorooctanoic acid (PFOA), perfluorooctane sulfonic acid (PFOS) were analyzed, because of high detective rates. Considering the skew distribution of PFAS levels, the natural logarithm-transformed PFAS (Ln-PFAS) was used. Logistic regression analysis, restricted cubic spline (RCS), and weighted quantile sum (WQS) regression were performed to explore the single, nonlinear, and mixed effects. A mediating analysis was used to evaluate the mediated effects of albumin.
RESULTS
Individuals with COPD had higher levels of PFHxS, PFNA, PFOA, and PFOS compared to those without COPD. Ln-PFNA (OR : 1.92, 95 % CI:1.31 to 2.80, P: <0.001; OR : 1.07, 95 % CI: 0.81 to 1.40, P: 0.636) and ln-PFOA (OR : 2.17, 95 % CI:1.38 to 3.41, P: <0.001; OR : 1.49, 95 % CI: 1.08 to 2.05, P: 0.016) were associated with COPD risk especially in males. The interaction between PFNA exposure and sex on COPD risk was significant (P : <0.001). The RCS curve demonstrated the nonlinear relationship between the ln-PFOA (P :0.001), ln-PFNA (P :0.045), and COPD risk in males. WQS analysis showed mixed PFAS exposure was correlated with COPD risk in males (OR: 1.44, 95 % CI:1.18 to 1.75, P: <0.001). Albumin mediated the relationship between PFOA and COPD (mediated proportion: -17.94 %).
CONCLUSION
This study concludes PFOA and PFNA are linked to a higher COPD risk in males, and serum albumin plays a mediating role in the relationship between PFOA and COPD. Thess findings are beneficial for the prevention of COPD. Further studies are required to explore potential mechanisms.
Topics: Male; Female; Humans; Nutrition Surveys; Environmental Pollutants; Serum Albumin; Prevalence; Alkanesulfonic Acids; Fluorocarbons; Alkanesulfonates; Pulmonary Disease, Chronic Obstructive; Caprylates; Fatty Acids
PubMed: 38494022
DOI: 10.1016/j.scitotenv.2024.171742 -
Frontiers in Public Health 2023Existing evidence indicates that exposure to per- and polyfluoroalkyl substances (PFASs) may increase the risk of hypertension, but the findings are inconsistent.... (Meta-Analysis)
Meta-Analysis
BACKGROUND
Existing evidence indicates that exposure to per- and polyfluoroalkyl substances (PFASs) may increase the risk of hypertension, but the findings are inconsistent. Therefore, we aimed to explore the relationship between PFASs and hypertension through this systematic review and meta-analysis.
METHODS
We searched PubMed, Embase, and the Web of Science databases for articles published in English that examined the relationship between PFASs and hypertension before 13 August 2022. The random effects model was used to aggregate the evaluation using Stata 15.0 for Windows. We also conducted subgroup analyses by region and hypertension definition. In addition, a sensitivity analysis was carried out to determine the robustness of the findings.
RESULTS
The meta-analysis comprised 15 studies in total with 69,949 individuals. The risk of hypertension was substantially and positively correlated with exposure to perfluorooctane sulfonate (PFOS) (OR = 1.31, 95% CI: 1.14, 1.51), perfluorooctanoic acid (PFOA) (OR = 1.16, 95% CI: 1.07, 1.26), and perfluorohexane sulfonate (PFHxS) (OR = 1.04, 95% CI: 1.00, 1.09). However, perfluorononanoic acid (PFNA) exposure and hypertension were not significantly associated (OR = 1.08, 95% CI: 0.99, 1.17).
CONCLUSION
We evaluated the link between PFASs exposure and hypertension and discovered that higher levels of PFOS, PFOA, and PFHxS were correlated with an increased risk of hypertension. However, further high-quality population-based and pathophysiological investigations are required to shed light on the possible mechanism and demonstrate causation because of the considerable variability.
SYSTEMATIC REVIEW REGISTRATION
https://www.crd.york.ac.uk/prospero/ PROSPERO, registration number: CRD 42022358142.
Topics: Humans; Alkanesulfonates; Fluorocarbons; Hypertension
PubMed: 37655293
DOI: 10.3389/fpubh.2023.1173101 -
Molecules (Basel, Switzerland) Sep 2021Piglet coccidiosis due to is a major cause of diarrhea and poor growth worldwide. It can effectively be controlled by application of toltrazuril (TZ), and oral...
Piglet coccidiosis due to is a major cause of diarrhea and poor growth worldwide. It can effectively be controlled by application of toltrazuril (TZ), and oral formulations have been licensed for many years. Recently, the first parenteral formulation containing TZ in combination with iron (gleptoferron) was registered in the EU for the prevention of coccidiosis and iron deficiency anemia, conditions in suckling piglets requiring routine preventive measures. This study evaluated the absorption and distribution of TZ and its main metabolite, toltrazuril sulfone (TZ-SO), in blood and intestinal tissues after single oral (20 mg/kg) or single intramuscular (45 mg/piglet) application of TZ. Fifty-six piglets were randomly allocated to the two treatment groups. Animals were sacrificed 1-, 5-, 13-, and 24-days post-treatment and TZ and TZ-SO levels were determined in blood, jejunal tissue, ileal tissue, and mixed jejunal and ileal content (IC) by high performance liquid chromatography (HPLC). Intramuscular application resulted in significantly higher and more sustained concentrations of both compounds in plasma, intestinal tissue, and IC. Higher concentrations after oral dosing were only observed one day after application of TZ in jejunum and IC. Toltrazuril was quickly metabolized to TZ-SO with maximum concentrations on day 13 for both applications. Remarkably, TZ and TZ-SO accumulated in the jejunum, the primary predilection site of , independently of the administration route, which is key to their antiparasitic effect.
Topics: Administration, Oral; Animals; Body Weight; Coccidiosis; Coccidiostats; Ileum; Injections, Intramuscular; Intestinal Mucosa; Jejunum; Sulfones; Swine; Swine Diseases; Triazines
PubMed: 34577103
DOI: 10.3390/molecules26185633