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Environment International Jul 2022Environmental risks caused by emerging per- and polyfluoroalkyl substances (PFASs) have attracted increasing attention. As an important substitute for perfluorooctane...
Environmental risks caused by emerging per- and polyfluoroalkyl substances (PFASs) have attracted increasing attention. As an important substitute for perfluorooctane sulfonate (PFOS), sodium p-perfluorous nonenoxybenzene sulfonate (OBS) is widely used as a firefighting foam additive and oil recovery agent in China. This study reported the tissue distribution of OBS in KM mice that were administered a dose of OBS at 10 µg/day via daily oral gavage for 7, 14, or 28 days. During exposure, gender-based differences were observed in body weight changes and tissue distribution of OBS. Liver exhibited the highest concentrations (males: 12.57 ± 1.80 µg/g; females: 11.80 ± 5.32 µg/g) and tissue/blood ratios and contributed more than 50% to the whole-body burden of OBS in both male and female mice, showing its ability to enrich PFASs. Furthermore, there were certain differences in the distribution characteristics of the three OBS isomers. Based on its bioaccumulation potential and widespread use, further studies are required on the human exposure risks of OBS.
Topics: Alkanesulfonates; Alkanesulfonic Acids; Animals; Bioaccumulation; Female; Fluorocarbons; Male; Mice; Sodium; Tissue Distribution
PubMed: 35588675
DOI: 10.1016/j.envint.2022.107289 -
Molecules (Basel, Switzerland) Jun 2020Anionic carbosilane dendrimers such as G2-S16 are very effective in preventing HSV-2 infection both in vitro and in vivo. We present the main achievements obtained for... (Review)
Review
Anionic carbosilane dendrimers such as G2-S16 are very effective in preventing HSV-2 infection both in vitro and in vivo. We present the main achievements obtained for the G2-S16 dendrimer in vivo, especially related to its efficacy against HSV-2 infection. Moreover, we discuss the mechanisms by which the G2-S16 dendrimer applied vaginally as a topical microbicide has been demonstrated to be safe and harmless for the vaginal microbiome balance, as both conditions present an essential step that has to be overcome during microbicide development. This review points to the marked protective effect of the G2-S16 dendrimer against sexually transmitted HSV-2 infection, supporting its role as a possible microbicide against HSV-2 infection.
Topics: Administration, Topical; Alkanesulfonates; Animals; Clinical Trials as Topic; Dendrimers; Herpes Genitalis; Herpesvirus 2, Human; Humans; Organosilicon Compounds; Treatment Outcome
PubMed: 32605185
DOI: 10.3390/molecules25132965 -
Scientific Reports Apr 2022In this work, Eucommia ulmoides leaf extract (EUOLstabilized silver nanoparticles (EUOL@AgNPs) incorporated sulfonated polyether sulfone (SPES)/polyethersulfone (PES)...
In this work, Eucommia ulmoides leaf extract (EUOLstabilized silver nanoparticles (EUOL@AgNPs) incorporated sulfonated polyether sulfone (SPES)/polyethersulfone (PES) electrospun nanofiber membranes (SP ENMs) were prepared by electrospinning, and they were studied for the removal of lead (Pb(II)) and cadmium (Cd(II)) ions from aqueous solutions. The SP ENMs with various EUOL@AgNPs loadings were characterized by X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectroscope, thermo-gravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and contact angle (CA) measurements. The adsorption studies showed that the adsorption of Cd(II) and Pb(II) was rapid, achieved equilibrium within 40 min and 60 min, respectively and fitted with non-linear pseudo-second-order (PSO) kinetics model. For Cd(II) and Pb(II), the Freundlich model described the adsorption isotherm better than the Langmuir isotherm model. The maximum adsorption capacity for Cd(II) and Pb(II) was 625 and 370.37 mg g respectively at neutral pH. Coexisting anions of fluoride, chloride, and nitrate had a negligible influence on Cd(II) removal than the Pb(II). On the other hand, the presence of silicate and phosphate considerably affected Cd(II) and Pb(II) adsorption. The recyclability, regeneration, and reusability of the fabricated EUOL@AgNPs-SP ENMs were studied and they retained their high adsorption capacity up to five cycles. The DFT measurements revealed that SP-5 ENMs exhibited the highest adsorption selectivity for Cd(II) and the measured binding energies for Cd(II), Pb(II), are 219.35 and 206.26 kcal mol, respectively. The developed ENM adsorbent may find application for the removal of heavy metals from water.
Topics: Adsorption; Alkanesulfonates; Cadmium; Hydrogen-Ion Concentration; Kinetics; Lead; Metal Nanoparticles; Metals, Heavy; Nanofibers; Polymers; Silver; Sulfones; Water; Water Pollutants, Chemical
PubMed: 35388115
DOI: 10.1038/s41598-022-09802-9 -
Journal of the American Chemical Society Mar 2022Sulfone-substituted bicyclo[1.1.0]butanes and housanes have found widespread application in organic synthesis due to their bench stability and high reactivity in...
Sulfone-substituted bicyclo[1.1.0]butanes and housanes have found widespread application in organic synthesis due to their bench stability and high reactivity in strain-releasing processes in the presence of nucleophiles or radical species. Despite their increasing utility, their preparation typically requires multiple steps in low overall yield. In this work, we report an expedient and general one-pot procedure for the synthesis of 1-sulfonylbicyclo[1.1.0]butanes from readily available methyl sulfones and inexpensive epichlorohydrin via the dialkylmagnesium-mediated formation of 3-sulfonylcyclobutanol intermediates. Furthermore, the process was extended to the formation of 1-sulfonylbicyclo[2.1.0]pentane (housane) analogues when 4-chloro-1,2-epoxybutane was used as the electrophile instead of epichlorohydrin. Both procedures could be applied on a gram scale with similar efficiency and are shown to be fully stereospecific in the case of housanes when an enantiopure epoxide was employed, leading to a streamlined access to highly valuable optically active strain-release reagents.
Topics: Butanes; Dimethyl Sulfoxide; Epichlorohydrin; Indicators and Reagents; Sulfones
PubMed: 35285232
DOI: 10.1021/jacs.2c00923 -
International Journal of Environmental... Sep 2023Perfluorohexane sulfonate (PFHxS) is a widely detected replacement for legacy long-chain perfluoroalkyl substances (PFAS) in the environment and human blood samples. Its...
Perfluorohexane sulfonate (PFHxS) is a widely detected replacement for legacy long-chain perfluoroalkyl substances (PFAS) in the environment and human blood samples. Its potential toxicity led to its recent classification as a globally regulated persistent organic pollutant. Although animal studies have shown a positive association between PFHxS levels and hepatic steatosis and hepatocellular hypertrophy, the link with liver toxicity, including end-stage liver cancer, remains inconclusive. In this study, we examined the effects of PFHxS on the proliferation of Hep3B (human hepatocellular carcinoma) and SK-Hep1 (human liver sinusoidal endothelial cells). Cells were exposed to different PFHxS concentrations for 24-48 h to assess viability and 12-14 days to measure colony formation. The viability of both cell lines increased at PFHxS concentrations <200 μM, decreased at >400 μM, and was highest at 50 μM. Colony formation increased at <300 μM and decreased at 500 μM PFHxS. Consistent with the effect on cell proliferation, PFHxS increased the expression of proliferating cell nuclear antigen (PCNA) and cell-cycle molecules (CDK2, CDK4, cyclin E, and cyclin D1). In summary, PFHxS exhibited a biphasic effect on liver cell proliferation, promoting survival and proliferation at lower concentrations and being cytotoxic at higher concentrations. This suggests that PFHxS, especially at lower concentrations, might be associated with HCC development and progression.
Topics: Animals; Humans; Sulfonic Acids; Carcinoma, Hepatocellular; Endothelial Cells; Liver Neoplasms; Alkanesulfonates; Fluorocarbons; Cell Proliferation; Alkanesulfonic Acids; Environmental Pollutants
PubMed: 37835138
DOI: 10.3390/ijerph20196868 -
Journal of the American Chemical Society Feb 2017This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C-C bonds. Optimization of a...
This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C-C bonds. Optimization of a reductive diene cyclization led to the development of an intermolecular cross-coupling of electronically-differentiated donor and acceptor olefins. Although the substitution on the donor olefins was initially limited to alkyl and aryl groups, additional efforts culminated in the expansion of the scope of the substitution to various heteroatom-based functionalities, providing a unified olefin reactivity. A vinyl sulfone acceptor olefin was developed, which allowed for the efficient synthesis of sulfone adducts that could be used as branch points for further diversification. Moreover, this reactivity was extended into an olefin-based Minisci reaction to functionalize heterocyclic scaffolds. Finally, mechanistic studies resulted in a more thorough understanding of the reaction, giving rise to the development of a more efficient second-generation set of olefin cross-coupling conditions.
Topics: Alkenes; Catalysis; Free Radicals; Iron Compounds; Molecular Structure; Sulfones
PubMed: 28094980
DOI: 10.1021/jacs.6b13155 -
Environmental Science & Technology Jan 2024Human exposure to perfluorinated alkylate substances (PFASs) is usually assessed from the concentrations in serum or plasma, assuming one-compartment toxicokinetics. To...
Human exposure to perfluorinated alkylate substances (PFASs) is usually assessed from the concentrations in serum or plasma, assuming one-compartment toxicokinetics. To characterize body distributions of major PFASs, we obtained and extracted tissue samples from 19 forensic autopsies of healthy adult subjects who had died suddenly and were not known to have elevated levels of PFAS exposure. As target organs of toxicological importance, we selected the liver, kidneys, lungs, spleen, and brain, as well as whole blood. Samples weighing about 0.1 g were analyzed by liquid chromatography coupled to triple mass spectrometers. Minor variations in PFAS concentrations were found between the kidney cortex and medulla and between lung lobes. Organ concentrations of perfluorooctanoic sulfonate (PFOS) and perfluorononanoate (PFNA) correlated well with blood concentrations, while perfluorooctanoate (PFOA) and perfluorohexanoic sulfonate (PFHxS) showed more variable associations. Likewise, the liver concentrations correlated well with those of other organs. Calculations of relative distributions were carried out to assess the interdependence of organ retentions. Equilibrium model predictions largely explained the observed PFAS distributions, except for the brain. Although the samples were small and affected by a possible lack of homogeneity, these findings support the use of blood-PFAS concentrations as a measure of PFAS exposure, with the liver possibly acting as the main organ of retention.
Topics: Adult; Humans; Environmental Pollutants; Alkanesulfonic Acids; Alkanesulfonates; Plasma; Fluorocarbons
PubMed: 38154793
DOI: 10.1021/acs.est.3c06499 -
Alcoholism, Clinical and Experimental... Mar 2016In the accompanying article, we showed that activation of peroxisome proliferator-activated receptor alpha (PPARα) signaling by fenofibrate and tesaglitazar decreases...
BACKGROUND
In the accompanying article, we showed that activation of peroxisome proliferator-activated receptor alpha (PPARα) signaling by fenofibrate and tesaglitazar decreases ethanol (EtOH) consumption in mice. In this study, we determined the role of these PPAR agonists in EtOH-related behaviors and other actions that may be important in regulating EtOH consumption.
METHODS
The effects of fenofibrate (150 mg/kg) and tesaglitazar (1.5 mg/kg) were examined on the following responses in male and female C57BL/6J (B6) and B6 × 129S4 mice: preference for saccharin, EtOH-induced conditioned place preference (CPP), conditioned taste aversion (CTA), loss of righting reflex, and withdrawal, acoustic startle reflex, response to novelty, and EtOH clearance. Because the B6 inbred strain usually displays weak EtOH-induced CPP and weak EtOH-induced acute withdrawal, B6 × 129S4 mice were also studied.
RESULTS
Fenofibrate and tesaglitazar decreased the novelty response and increased acute EtOH withdrawal severity, and fenofibrate increased EtOH-induced CTA. Two important factors for EtOH consumption (saccharin preference and EtOH-induced CPP) were not altered by fenofibrate or tesaglitazar. EtOH clearance was increased by both fenofibrate and tesaglitazar. Response to novelty, acute withdrawal, and EtOH clearance show sex differences and could contribute to the reduced EtOH consumption following fenofibrate administration.
CONCLUSIONS
These studies indicate the complexity of EtOH-dependent and EtOH-independent behaviors that are altered by PPAR agonists and provide evidence for novel behavioral actions of these drugs that may contribute to PPAR-mediated effects on alcohol drinking.
Topics: Alcohol Drinking; Alkanesulfonates; Animals; Avoidance Learning; Conditioning, Classical; Female; Fenofibrate; Locomotion; Male; Mice; Mice, 129 Strain; Mice, Inbred C57BL; PPAR alpha; Phenylpropionates; Reflex, Righting; Taste
PubMed: 26857541
DOI: 10.1111/acer.12972 -
Environmental Research Aug 2023Although some studies report that exposure to per- and polyfluoroalkyl substances (PFAS) during pregnancy and early life stages of a child could adversely impact...
BACKGROUND
Although some studies report that exposure to per- and polyfluoroalkyl substances (PFAS) during pregnancy and early life stages of a child could adversely impact neurodevelopment, literature shows mixed evidence.
OBJECTIVES
Using an ecological framework for human development, we assessed the association of risk factors for environmental PFAS exposure and childhood PFAS concentrations with behavioral difficulties among school-age children exposed to PFAS from birth, while also controlling for the important influence of the parenting and familial environment.
METHODS
The study participants included 331 school-age children (6-13 years) born in a PFAS-contaminated area in the Veneto Region (Italy). We study the associations between environmental risk factors of maternal PFAS exposure (residential time, consumption of tap water, residence in Red zone A or B), and breastfeeding duration with parent assessments of children's behavioral problems (using the Strengths and Difficulties Questionnaire [SDQ]), adjusting for socio-demographic, parenting and familial variables. The direct relationships between serum blood PFAS concentrations and SDQ scores was evaluated in a subset of children (n = 79), both with single PFAS and weighted quantile sum (WQS) regressions.
RESULTS
Poisson regression models reported positive associations between high consumption of tap water and externalizing SDQ scores (Incidence Rate Ratio [IRR]: 1.18; 95% confidence interval [CI]: 1.04-1.32) and total difficulty scores (IRR: 1.14; 95% CI: 1.02-1.26). Childhood perfluorooctane sulfonate (PFOS) and perfluorohexane sulfonate (PFHxS) were associated with higher internalizing SDQ scores (4th vs. 1st quartile, PFOS IRR: 1.54, 95% CI: 1.06-2.25), externalizing scores (4th vs. 1st quartile, PFHxS IRR: 1.59, 95% CI: 1.09-2.32), and total difficulty scores (4th vs. 1st quartile, PFOS IRR: 1.37, 95% CI: 1.05-1.71; PFHxS IRR: 1.54, 95% CI: 1.09-1.90). The WQS regressions confirmed the associations reported by single-PFAS analyses.
CONCLUSIONS
We observed cross-sectional associations of tap water consumption and childhood PFOS, and PFHxS concentrations with greater behavioral difficulties.
Topics: Pregnancy; Female; Humans; Child; Cross-Sectional Studies; Environmental Exposure; Alkanesulfonic Acids; Alkanesulfonates; Fluorocarbons; Water; Environmental Pollutants
PubMed: 37207732
DOI: 10.1016/j.envres.2023.116049 -
International Journal of Molecular... Dec 2020Development of new, safe, and effective microbicides to prevent human immunodeficiency virus HIV sexual transmission is needed. Unfortunately, most microbicides proved... (Review)
Review
Development of new, safe, and effective microbicides to prevent human immunodeficiency virus HIV sexual transmission is needed. Unfortunately, most microbicides proved ineffective to prevent the risk of HIV-infection in clinical trials. We are working with G2-S16 polyanionic carbosilane dendrimer (PCD) as a new possible vaginal topical microbicide, based on its short reaction times, wide availability, high reproducibility, and quantitative yields of reaction. G2-S16 PCD exerts anti-HIV activity at an early stage of viral replication, by blocking gp120/CD4/CCR5 interaction, and providing a barrier against infection for long periods of time. G2-S16 PCD was stable at different pH values, as well as in the presence of seminal fluids. It maintained the anti-HIV activity against R5/X4 HIV over time, did not generate any type of drug resistance, and retained the anti-HIV effect when exposed to semen-enhanced viral infection. Importantly, G2-S16 PCD did not modify vaginal microbiota neither in vitro or in vivo. Histopathological examination did not show vaginal irritation, inflammation, lesions, or damage in the vaginal mucosa, after administration of G2-S16 PCD at different concentrations and times in female mice and rabbit animal models. Based on these promising data, G2-S16 PCD could become a good, safe, and readily available candidate to use as a topical vaginal microbicide against HIV.
Topics: Administration, Intravaginal; Alkanesulfonates; Animals; Anti-HIV Agents; Dendrimers; Drug Evaluation, Preclinical; Female; HIV Infections; Humans; Male; Organosilicon Compounds
PubMed: 33321835
DOI: 10.3390/ijms21249403