-
Molecules (Basel, Switzerland) Aug 2021In this study, a new synthetic 1,2,3-triazole-containing disulfone compound was derived from dapsone. Its chemical structure was confirmed using microchemical and...
In this study, a new synthetic 1,2,3-triazole-containing disulfone compound was derived from dapsone. Its chemical structure was confirmed using microchemical and analytical data, and it was tested for its in vitro antibacterial potential. Six different pathogenic bacteria were selected. MICs values and ATP levels were determined. Further, toxicity performance was measured using MicroTox Analyzer. In addition, a molecular docking study was performed against two vital enzymes: DNA gyrase and Dihydropteroate synthase. The results of antibacterial abilities showed that the studied synthetic compound had a strong bactericidal effect against all tested bacterial strains, as Gram-negative species were more susceptible to the compound than Gram-positive species. Toxicity results showed that the compound is biocompatible and safe without toxic impact. The molecular docking of the compound showed interactions within the pocket of two enzymes, which are able to stabilize the compound and reveal its antimicrobial activity. Hence, from these results, this study recommends that the established compound could be an outstanding candidate for fighting a broad spectrum of pathogenic bacterial strains, and it might therefore be used for biomedical and pharmaceutical applications.
Topics: Anti-Bacterial Agents; DNA Gyrase; Dapsone; Dihydropteroate Synthase; Gram-Negative Bacteria; Gram-Positive Bacteria; Humans; Microbial Sensitivity Tests; Molecular Docking Simulation; Molecular Structure; Structure-Activity Relationship; Sulfones; Topoisomerase II Inhibitors; Triazoles
PubMed: 34443405
DOI: 10.3390/molecules26164817 -
The Science of the Total Environment Feb 2022Environmental contaminants including long-chain per- and polyfluoroalkyl substances (PFAS) have been linked to cancer, which is a central cause of mortality in humans...
Environmental contaminants including long-chain per- and polyfluoroalkyl substances (PFAS) have been linked to cancer, which is a central cause of mortality in humans and many wildlife species. Today shorter-chain PFAS are extensively used as replacement compounds and commonly found in the environment. Mechanistic studies are important for a better understanding of their toxicological potential and possible role in cancer etiology. Here, we treated normal human breast epithelial cells (MCF-10A) with 500 pM to 500 μM of perfluorohexane sulfonate (PFHxS), undecafluorohexanoic acid (PFHxA), hexafluoropropylene oxide-dimer acid (GenX), perfluoro 3,6 dioxaoctanoic acid (PFO2OA), heptafluorobutyric acid (HFBA) and perfluorobutanesulfonic acid (PFBS) for 72 h to investigate potential effects on cell proliferation and neoplastic transformation. PFHxA, GenX, PFO2OA, HFBA and PFBS induced no alterations compared to controls at any of the concentrations tested. Exposure to 100 μM PFHxS on the other hand was shown to affect important regulatory cell-cycle proteins (cyclin D1, CDK6, p27, p53 and ERK) and induced cell proliferation, at least in part through activation of the constitutive androstane receptor (CAR) and the peroxisome proliferator-activated receptor alpha (PPARα). PFHxS also altered histone modifications and induced cell malignance by reducing the levels of adhesion proteins (E-cadherin and β-integrin) and promoting cell migration and invasion. These results demonstrate that five out of six alternative PFAS tested are clearly less harmful to MCF-10A cells than previously studied PFOS and PFOA, but raise concerns about PFHxS that also has been associated with breast cancer in epidemiological studies.
Topics: Alkanesulfonates; Alkanesulfonic Acids; Carcinogenesis; Constitutive Androstane Receptor; Environmental Pollutants; Fluorocarbons; Humans
PubMed: 34843762
DOI: 10.1016/j.scitotenv.2021.151945 -
Environmental Science & Technology May 2023Drinking water contamination by per- and polyfluoroalkyl substances (PFAS) is widespread near more than 300 United States (U.S.) military bases that used aqueous...
Drinking water contamination by per- and polyfluoroalkyl substances (PFAS) is widespread near more than 300 United States (U.S.) military bases that used aqueous film-forming foams (AFFF) for fire training and firefighting activities. Much of the PFAS at these sites consist of precursors that can transform into terminal compounds of known health concern but are omitted from standard analytical methods. Here, we estimate the expected duration and contribution of precursor biotransformation to groundwater PFAS contamination at an AFFF-contaminated military base on Cape Cod, Massachusetts, United States, by optimizing a geochemical box model using measured PFAS concentrations from a multidecadal time series of groundwater and a soil survey in the source zone. A toolbox of analytical techniques used to reconstruct the mass budget of PFAS showed that precursors accounted for 46 ± 8% of the extractable organofluorine (a proxy for total PFAS) across years. Terminal PFAS still exceed regulatory limits by 2000-fold decades after AFFF use ceased. Measurements and numerical modeling show that sulfonamido precursors are retained in the vadose zone and their slow biotransformation into perfluoroalkyl sulfonates (half-life > 66 yr) sustains groundwater concentrations of perfluorobutane sulfonate (PFBS) and perfluorohexane sulfonate (PFHxS). The estimated PFAS reservoir in the vadose zone and modeled flux into groundwater suggest PFAS contamination above regulatory guidelines will persist for centuries without remediation.
Topics: Humans; Military Personnel; Water Pollutants, Chemical; Water; Water Pollution; Fluorocarbons; Alkanesulfonates; Groundwater
PubMed: 37184088
DOI: 10.1021/acs.est.3c00675 -
Environment International Feb 2023Bisphenol S (BPS) and its 11 emerging analogues were investigated in 325 urine samples from five occupational populations in South China. Besides BPS, ten emerging BPS...
Bisphenol S (BPS) and its 11 emerging analogues were investigated in 325 urine samples from five occupational populations in South China. Besides BPS, ten emerging BPS analogues were newly identified and detected in the urine. It should be noted that urinary concentrations of dominant BPS analogues of 2,4'-bis(hydroxyphenyl)sulfone (2,4-BPS), bis(3-allyl-4-hydroxyphenyl)sulfone (TGSA) and diphenylsulfone (DPS) were 1.1-2.3 times higher than that of BPS, with overall detection frequencies at 74-91 %. The median sum concentrations of the target 12 bisphenols (ng/mL) were found highest in urine from cashiers (1.12), followed by water plant staffs (0.994), teachers (0.552), doctors (0.408) and power plant staffs (0.333). The composition profile of the urinary dominant bisphenols was occupational-dependent, with 2,4-BPS accounting for 45-73 % in cashiers and power plant staffs, and with DPS and TGSA for 74-82 % among doctors, teachers and water plant staffs. Significant correlations were found among the most frequently detected bisphenols in cashiers, indicating their common application and emission pathways. The median exposures based on estimated daily intakes (EDIs, ng/kg bw/day) for the 12 bisphenols in cashiers and water plant staffs (31.6-35.6) were 1.8-3.4 times higher than those of teachers, doctors and power plant staffs (10.6-17.5). This is the first study to identify multiple emerging BPS analogues in urine from occupational populations, especially cashiers and water plant staffs.
Topics: Humans; Phenols; Sulfones; Benzhydryl Compounds; China
PubMed: 36736027
DOI: 10.1016/j.envint.2023.107773 -
Yakugaku Zasshi : Journal of the... Nov 2008The number of reports on new techniques in molecular imaging has been recently increasing because of their usefulness in biological, medical, and clinical research.... (Review)
Review
The number of reports on new techniques in molecular imaging has been recently increasing because of their usefulness in biological, medical, and clinical research. Fluorescence imaging methods are generally superior in terms of sensitivity, selectivity and ease of use. Cyanine dyes have been employed as fluorescent labels in fluorescence imaging studies of biological mechanisms. In particular, tricarbocyanines have the advantage that light at their emission and absorption maxima in the near-infrared (NIR) region around 650-900 nm is relatively poorly absorbed by biomolecules, and so can penetrate deeply into tissues. There is also less autofluorescence in this region. In addition to cyanine dyes for straightforward fluorescence labeling, we successfully developed cyanine dyes whose fluorescence intensity changes upon specific reaction with nitric oxide, which is an important signaling molecule involved in the regulation of a wide range of physiological and pathophysiological mechanisms, and many disorders. Then, we synthesized dipicolylcyanine (DIPCY), consisting of tricarbocyanine as a fluorophore and dipicolylethylenediamine as a heavy metal chelator, and investigated its response to various heavy metal ions. Upon addition of zinc ion, a red shift of the absorbance maximum was observed. Namely, DIPCY can work as a ratiometric fluorescent sensor for zinc ion in the NIR region. Moreover, we have recently developed several pH probes based on the amine-substituted tricarbocyanine fluorophore. We could measure pH with these fluorescent probes by a ratiometric monitoring method.
Topics: Alkanesulfonates; Carbocyanines; Diagnostic Imaging; Energy Transfer; Fluorescent Dyes; Hydrogen-Ion Concentration; Nitric Oxide; Spectroscopy, Near-Infrared
PubMed: 18981701
DOI: 10.1248/yakushi.128.1653 -
National Toxicology Program Technical... Sep 2001p,pN-Dichlorodiphenyl sulfone is used as a starting material in the production of polysulfones and polyethersulfones and as a component in reactive dyes in the textile...
UNLABELLED
p,pN-Dichlorodiphenyl sulfone is used as a starting material in the production of polysulfones and polyethersulfones and as a component in reactive dyes in the textile industry; it is also a by-product of pesticide production. p,pN-Dichlorodiphenyl sulfone was nominated for study by the National Cancer Institute because of its history of high production and use, the prospect of increased production and use, and the absence of adequate toxicity testing. Male and female F344/N rats and B6C3F1 mice were exposed top,pN-dichlorodiphenyl sulfone (greater than 99% pure)in feed for 14 weeks or 2 years. Genetic toxicology studies were conducted in Salmonella typhimurium,cultured Chinese hamster ovary cells, and mouse bone marrow. 14-WEEK STUDY IN RATS: Groups of 10 male and 10 female F344/N rats were fed diets containing 0, 30, 100, 300, 1,000, or 3,000 ppm p,pN-dichlorodiphenyl sulfone (equivalent to average daily doses of approximately 2, 6, 19, 65, or 200 mgp,pN-dichlorodiphenyl sulfone/kg body weight) for 14 weeks. All rats survived until the end of the study. Mean body weights of groups exposed to 300 ppm or greater were significantly less than those of the controls. Liver weights of groups exposed to 100 ppm or greater and kidney weights of 1,000 and 3,000 ppm male rats were significantly greater than those of the controls. Centrilobular hepatocyte hypertrophy of the liver was observed in most male rats exposed to 100 ppm or greater and in all female rats exposed to 300 ppm or greater, and the severities were increased in 300 ppm males and 1,000 and 3,000 ppm males and females. The incidences of nephropathy in 1,000 and 3,000 ppm female rats were significantly increased. Dose-related increases in severity of nephropathy were observed in male rats. 14-WEEK STUDY IN MICE: Groups of 10 male and 10 female B6C3F1 mice were fed diets containing 0, 30, 100, 300, 1,000, or 3,000 ppm p,pN-dichlorodiphenyl sulfone (equivalent to average daily doses of approximately 3.5, 15, 50, 165,or 480 mg/kg) for 14 weeks. All mice survived until the end of the study. Mean body weights of groups exposed to 300 ppm or greater were significantly less than those of the controls. Liver weights of groups exposed to 300 ppm or greater were significantly increased. Centrilobular hypertrophy of the liver was observed in most males exposed to 100 ppm or greater and in all females exposed to 1,000 or 3,000 ppm, and the severities generally increased with increasing exposure concentration. 2-YEAR STUDY IN RATS: Groups of 50 male and 50 female rats were fed diets containing 0, 10 (males), 30, 100, or 300 (females) ppm p,pN-dichlorodiphenyl sulfone for 105 weeks. Dietary concentrations of 10, 30, and 100 ppm resulted in average daily doses of approximately 0.5, 1.5, and 5.0 mg/kg to males. Dietary concentrations of 30, 100,and 300 ppm resulted in average daily doses of approximately 1.6, 5.4, and 17 mg/kg to females. Additional groups of 10 male and 10 female rats were fed the same p,pN-dichlorodiphenyl sulfone-containing diets for 18 months and bled for plasma determinations of p,pN-dichlorodiphenyl sulfone at approximately 2 weeks and 3, 12, and 18 months. Survival of all exposed groups of male and female rats was similar to that of the control groups. Mean body weights of 30 and 100 ppm males were generally less than those of the controls during the latter part of the study, and mean body weights of 100 and 300 ppm female rats were less from weeks 30 and 18,respectively. Feed consumption by the exposed groups was similar to that by the controls throughout the study. The incidences of centrilobular hepatocyte hypertrophy in 100 ppm male and 100 and 300 ppm female rats were significantly greater than those in the controls. The incidences of bile duct hyperplasia and centrilobular degeneration were also significantly increased in 100 and 300 ppm females. No neoplasms were related to chemical exposure. 2-YEAR STUDY IN MICE: Groups of 50 male and 50 female mice were fed diets containing 0, 30, 100, or 300 ppm p,pN-dichlorodiphenyl sulfone for 105 to 106 weeks. Dietary concentrations of 30, 100, and 300 ppm delivered average daily doses of approximately 4, 13, and 40 mg/kg to males and approximately 3, 10, and 33 mg/kg to females. Additional groups of 10 male and 10 female mice were fed the same p,pN-dichlorodiphenyl sulfone-containing diets for up to 12 months;three mice in each group were bled for plasma determinations of p,pN-dichloro-diphenyl sulfone at approximately 2 weeks or 3 or 12 months. Survival of all exposed groups of male and female mice was similar to that of the control groups. Mean body weights of 300 ppm mice were less than those of the controls throughout most of the study. Feed consumption by the exposed groups was similar to that by the controls throughout the study. The incidences of centrilobular hepatocyte hypertrophy in all exposed groups of male mice and in 100 and 300 ppm females were significantly greater than those in the controls. The incidence of eosinophilic foci in 300 ppm females was significantly increased. No neoplasms were related to chemical exposure. PHARMACOKINETICS OF p,pN-DICHLORODIPHENYL SULFONE: p,pN-Dichlorodiphenyl sulfone is rapidly absorbed from the gut and metabolized by a saturable process. Although some p,pN-dichlorodiphenyl sulfone is eliminated unchanged in feces and urine, most of the elimination is via metabolism. Mathematical modeling of the toxicokinetics supports the view that p,pN-dichlorodiphenyl sulfone induces enzymes involved in its metabolism.
GENETIC TOXICOLOGY
p,pN-Dichlorodiphenyl sulfone was not mutagenic in any of several strains of Salmonella typhimurium, with or without metabolic activation enzymes (S9). Results of the sister chromatid exchange test in cultured Chinese hamster ovary cells were judged to be negative in the presence of S9 and equivocal in the absence of S9, but no induction of chromosomal aberrations was noted, with or without S9. In contrast to the in vitro results, positive results were obtained in an acute in vivo mouse bone marrow micronucleus assay with p,pN-dichlorodiphenyl sulfone administered by intraperitoneal injection three times over a dose range of 200 to 800 mg/kg.
CONCLUSIONS
Under the conditions of these 2-year feed studies, there was no evidence of carcinogenic activity* of p,pN-dichlorodiphenyl sulfone in male F344/N rats exposed to 10, 30, or 100 ppm or in female F344/N rats exposed to 30, 100, or 300 ppm. There was no evidence of carcinogenic activity of p,pN-dichlorodiphenyl sulfone in male or female B6C3F1 mice exposed to 30,100, or 300 ppm. Exposure to p,pN-dichlorodiphenyl sulfone for 2 years caused increased incidences of nonneoplastic lesions of the liver in male and female rats and mice.
Topics: Administration, Oral; Animals; Bone Marrow Cells; Carcinogenicity Tests; Carcinogens; Diet; Dose-Response Relationship, Drug; Female; Male; Mice; Mice, Inbred Strains; Micronucleus Tests; Mutagens; Neoplasms, Experimental; Rats; Rats, Inbred F344; Sulfones
PubMed: 12087421
DOI: No ID Found -
Chemistry (Weinheim An Der Bergstrasse,... Dec 2022A facile and environmentally friendly electrochemical protocol is herein reported for the C(sp )-C(sp ) cross dehydrogenative coupling between imidazopyridines and...
A facile and environmentally friendly electrochemical protocol is herein reported for the C(sp )-C(sp ) cross dehydrogenative coupling between imidazopyridines and N,N-dimethylanilines. The broad functional group compatibility includes halogens, ester, alcohol, sulfone as well as thiophene. This methodology is also suitable for benzo[d]imidazo[2,1-b]thiazole, thiazoimidazole and tetrahydroisoquinoline, and can be scaled up to 5 mmol. Mechanistic insights are discussed.
Topics: Imidazoles; Pyridines; Thiazoles; Sulfones
PubMed: 36048580
DOI: 10.1002/chem.202202135 -
Applied and Environmental Microbiology Jul 2023Sulfoquinovose (SQ, 6-deoxy-6-sulfo-glucose) constitutes the polar head group of plant sulfolipids and is one of the most abundantly produced organosulfur compounds in...
Sulfoquinovose (SQ, 6-deoxy-6-sulfo-glucose) constitutes the polar head group of plant sulfolipids and is one of the most abundantly produced organosulfur compounds in nature. Degradation of SQ by bacterial communities contributes to sulfur recycling in many environments. Bacteria have evolved at least four mechanisms for glycolytic degradation of SQ, termed sulfoglycolysis, producing C3 sulfonate (dihydroxypropanesulfonate and sulfolactate) and C2 sulfonate (isethionate) by-products. These sulfonates are further degraded by other bacteria, leading to the mineralization of the sulfonate sulfur. The C2 sulfonate sulfoacetate is widespread in the environment and is also thought to be a product of sulfoglycolysis, although the mechanistic details are yet unknown. Here, we describe a gene cluster in an sp., from a metagenome derived from deeply circulating subsurface aquifer fluids (GenBank accession no. QZKD01000037), encoding a variant of the recently discovered sulfoglycolytic transketolase (sulfo-TK) pathway that produces sulfoacetate instead of isethionate as a by-product. We report the biochemical characterization of a coenzyme A (CoA)-acylating sulfoacetaldehyde dehydrogenase (SqwD) and an ADP-forming sulfoacetate-CoA ligase (SqwKL), which collectively catalyze the oxidation of the transketolase product sulfoacetaldehyde into sulfoacetate, coupled with ATP formation. A bioinformatics study revealed the presence of this sulfo-TK variant in phylogenetically diverse bacteria, adding to the variety of mechanisms by which bacteria metabolize this ubiquitous sulfo-sugar. Many bacteria utilize environmentally widespread C2 sulfonate sulfoacetate as a sulfur source, and the disease-linked human gut sulfate- and sulfite-reducing bacteria can use it as a terminal electron receptor for anaerobic respiration generating toxic HS. However, the mechanism of sulfoacetate formation is unknown, although it has been proposed that sulfoacetate originates from bacterial degradation of sulfoquinovose (SQ), the polar head group of sulfolipids present in all green plants. Here, we describe a variant of the recently discovered sulfoglycolytic transketolase (sulfo-TK) pathway. Unlike the regular sulfo-TK pathway that produces isethionate, our biochemical assays with recombinant proteins demonstrated that a CoA-acylating sulfoacetaldehyde dehydrogenase (SqwD) and an ADP-forming sulfoacetate-CoA ligase (SqwKL) in this variant pathway collectively catalyze the oxidation of the transketolase product sulfoacetaldehyde into sulfoacetate, coupled with ATP formation. A bioinformatics study revealed the presence of this sulfo-TK variant in phylogenetically diverse bacteria and interpreted the widespread existence of sulfoacetate.
Topics: Humans; Transketolase; Bacteria; Alkanesulfonates; Oxidoreductases; Adenosine Triphosphate; Sulfur; Ligases
PubMed: 37404184
DOI: 10.1128/aem.00617-23 -
Scientific Reports Jul 2023Smart water injection is one of the engineering techniques to enhance oil recovery (EOR) from carbonate and sandstone reservoirs that have been widely used in recent...
Smart water injection is one of the engineering techniques to enhance oil recovery (EOR) from carbonate and sandstone reservoirs that have been widely used in recent decades. Wettability alteration and IFT are among the essential and influential mechanisms that can be mentioned to achieve EOR. One of the critical issues in the field of EOR is the effect of reservoir ions on the formation and stability of the emulsion. Investigating the role and performance of these ions during EOR processes is of significant importance. These processes are based on smart water injection and natural production. In this research, stability was investigated and formed during the injection of different concentrations of anionic and cationic surfactants, respectively alpha olefin sulfonate (AOS) and cetrimonium bromide (CTAB), into a water-oil emulsion with a volume ratio of 30-70. Considering the droplet diameter distribution and the flow speed of separation by centrifugation, the optimal concentration level has been investigated in both surfactants. Based on the results, the highest stability and emulsion formation occurred in the presence of AOS surfactant. Then different concentrations of CaCl, MgCl, and NaCl salts were added in optimal concentrations of both surfactants. The formation and stability of the emulsion was checked by examining the distribution of the droplet diameter and the separation flow rate. AOS anionic surfactant had the most stability in the presence of MgCl salt, and better performance in stability of the emulsion was obtained. The maximum number of droplet diameters in the optimal concentration for AOS and CTAB surfactant systems is 1010 and 880, respectively, and for binary systems of AOS surfactant and MgCl, CaCl and NaCl salts, it is 2200, 1120 and 1110, respectively. Furthermore, for the CTAB binary system in the presence of MgCl, CaCl, and NaCl salts, it is 1200, 1110, and 1100, respectively. The stability of the emulsion of salts in the presence of both AOS and CTAB surfactants was MgCl2 > CaCl > NaCl.
Topics: Emulsions; Cetrimonium; Salts; Sodium Chloride; Calcium Chloride; Surface-Active Agents; Alkanesulfonates; Water
PubMed: 37443178
DOI: 10.1038/s41598-023-38428-8 -
Molecules (Basel, Switzerland) Jun 2020A simple, efficient, and selective oxidation under flow conditions of sulfides into their corresponding sulfoxides and sulfones is reported herein, using as a catalyst...
A simple, efficient, and selective oxidation under flow conditions of sulfides into their corresponding sulfoxides and sulfones is reported herein, using as a catalyst perselenic acid generated in situ by the oxidation of selenium (IV) oxide in a diluted aqueous solution of hydrogen peroxide as the final oxidant. The scope of the proposed methodology was investigated using aryl alkyl sulfides, aryl vinyl sulfides, and dialkyl sulfides as substrates, evidencing, in general, a good applicability. The scaled-up synthesis of (methylsulfonyl)benzene was also demonstrated, leading to its gram-scale preparation.
Topics: Catalysis; Hydrogen Peroxide; Molecular Structure; Oxidation-Reduction; Selenium Oxides; Sulfides; Sulfones; Sulfoxides
PubMed: 32545303
DOI: 10.3390/molecules25112711