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Water Research Aug 2021Sulfonamide antibiotics (SAs) are typical antibiotics and have attracted increasing concerns about their wide occurrence in environment as well as potential risk for...
Sulfonamide antibiotics (SAs) are typical antibiotics and have attracted increasing concerns about their wide occurrence in environment as well as potential risk for human health. In this study, we applied a novel advanced oxidation process in SAs degradation by combining molybdenum sulfide and peracetic acid (MoS/PAA). Reactive oxygen species (ROS) including HO, CHC(O)O, CHC(O)OO, and O were generated from PAA by MoS activation and contributed to SAs degradation. The effects of initial pH, the dosages of PAA and MoS, and humic acid for SAs degradation were further evaluated by selecting sulfamethoxazole (SMX) as a target SA in the MoS/PAA process. Results suggested that the optimum pH for SMX removal was 3, where the degradation efficiency of SMX was higher than 80% after reaction for 15 min. Increasing PAA (0.075-0.45 mM) or MoS (0.1-0.4 g/L) dosages facilitated the SMX degradation, while the presence of humic acids retarded the SMX removal. This MoS/PAA process also showed good efficiencies in removing other SAs including sulfaguanidine, sulfamonomethoxine and sulfamerazine. Their possible degradation pathways were proposed based on the products identification and DFT calculation, showing that apart from the oxidation of amine groups to nitro groups in SAs, MoS/PAA induced SO extrusion reaction for SAs that contained six-membered heterocyclic moieties.
Topics: Anti-Bacterial Agents; Disulfides; Humans; Hydrogen Peroxide; Molybdenum; Oxidation-Reduction; Peracetic Acid; Sulfamethoxazole; Sulfonamides; Water Pollutants, Chemical
PubMed: 34107364
DOI: 10.1016/j.watres.2021.117291 -
Molecules (Basel, Switzerland) Feb 2023Developing a simple and efficient method for removing organic micropollutants from aqueous systems is crucial. The present study describes the preparation and...
Developing a simple and efficient method for removing organic micropollutants from aqueous systems is crucial. The present study describes the preparation and application, for the first time, of novel MXene-decorated bismuth ferrite nanocomposites (BiFeO/MXene) for the removal of six sulfonamides including sulfadiazine (SDZ), sulfathiazole (STZ), sulfamerazine (SMZ), sulfamethazine (SMTZ), sulfamethoxazole (SMXZ) and sulfisoxazole (SXZ). The properties of BiFeO/MXene are enhanced by the presence of BiFeO nanoparticles, which provide a large surface area to facilitate the removal of sulfonamides. More importantly, BiFeO/MXene composites demonstrated remarkable sulfonamide adsorption capabilities compared to pristine MXene, which is due to the synergistic effect between BiFeO and MXene. The kinetics and isotherm models of sulfonamide adsorption on BiFeO/MXene are consistent with a pseudo-second-order kinetics and Langmuir model. BiFeO/MXene had appreciable reusability after five adsorption-desorption cycles. Furthermore, BiFeO/MXene is stable and retains its original properties upon desorption. The present work provides an effective method for eliminating sulfonamides from water by exploiting the excellent texture properties of BiFeO/MXene.
Topics: Sulfonamides; Bismuth; Sulfanilamide; Water; Nanocomposites; Adsorption; Water Pollutants, Chemical; Kinetics
PubMed: 36838529
DOI: 10.3390/molecules28041541 -
Environmental Science and Pollution... Aug 2021As a class of synthetic sulfur drugs, sulfonamides (SAs) have been used to treat diseases and promote organism growth. Different concentrations of SAs have been detected...
As a class of synthetic sulfur drugs, sulfonamides (SAs) have been used to treat diseases and promote organism growth. Different concentrations of SAs have been detected in the water environment, which has threatened the ecological environment. In this study, the contamination of 9 SAs in water, sediments, and 8 fish species from the Hangbu-Fengle River, China, were analyzed using UPLC-MS/MS. The total SA concentrations in surface water, sediments, and fish were ND-5.064 ng/L, ND-5.052 ng/g dry weight (d.w.), and ND-1.42 ng/g wet weight (w.w.), respectively. The major compounds were sulfadiazine (SDZ), sulfamerazine (SMZ), and sulfamethoxazole (SMX) in water and fish. The SA levels of in fish from different habitat preferences revealed a spatial difference, with the order of demersal species > pelagic species. Moreover, the SA concentrations were affected by trophic guilds, indicating their decrease in the order of piscivorous fish > omnivorous fish > planktivorous fish > herbivorous fish. The obtained bioaccumulation factors showed that SMZ and SMX have strong bioenrichments in Ophiocephalus argus Cantor and Pelteobagrus fulvidraco. The risk assessment indicated that SAs did not pose significant health threats to the organisms. This research is the first report of SA contamination in the Hangbu-Fenle River, which can provide an important scientific basis for their pollution prevention and ecological risk assessment in the aquatic environment.
Topics: Animals; Anti-Bacterial Agents; Bioaccumulation; China; Chromatography, Liquid; Environmental Monitoring; Fishes; Rivers; Sulfonamides; Tandem Mass Spectrometry; Water Pollutants, Chemical
PubMed: 33842998
DOI: 10.1007/s11356-021-13850-5 -
Ecotoxicology and Environmental Safety Jul 2019To evaluate the occurrence and ecological risk of organic contaminants in aquatic environment in China, a method for simultaneously detecting 130 pharmaceuticals and...
To evaluate the occurrence and ecological risk of organic contaminants in aquatic environment in China, a method for simultaneously detecting 130 pharmaceuticals and personal care products (PPCPs) and 35 pesticides has been established using solid phase extraction-ultra performance liquid chromatography-tandem mass spectrometry (SPE-UPLC-MS/MS) method. In the present survey, a total of 122 target compounds (103 PPCPs and 19 pesticides) were detected in seven major watersheds in China, with average concentrations ranged from 0.02 ng/L (sulfamerazine) to 332.75 ng/L (bisphenol A), revealing that PPCPs and pesticides were widely distributed in surface water of China. Antibiotics and organophosphorus were the most ubiquitously PPCPs and pesticides, respectively; quinolones were the predominant antibiotics, most of which were detected in more than 96% sampling sites, with average concentrations ranged from 2.14 to 309.67 ng/L; six pesticides including isoprocarb, fenobucarb, acetamiprid, imidacloprid, acetochlor and bentazone were detected in more than 80% sampling sites, with average concentrations ranged from 5.62 to 225.93 ng/L; more than half of the non-antibiotic pharmaceuticals were hormones; and diethyltoluamide (DEET) was predominant personal care products; The risk assessment showed that each watershed was at potential medium ecological risk based on their mean concentration (RQ > 1), and pesticides were the main compounds arising risks.
Topics: China; Chromatography, Liquid; Cosmetics; Environmental Monitoring; Fresh Water; Pesticides; Pharmaceutical Preparations; Solid Phase Extraction; Tandem Mass Spectrometry; Water Pollutants, Chemical
PubMed: 30898333
DOI: 10.1016/j.ecoenv.2019.01.131 -
ACS Omega Dec 2023The search for novel drug scaffolds that can improve effectiveness and safety through drug conjugates is a promising approach. Consequently, drug conjugates constitute a...
Exploring the Potential of New Benzamide-Acetamide Pharmacophore Containing Sulfonamide as Urease Inhibitors: Structure-Activity Relationship, Kinetics Mechanism, and In Silico Studies.
The search for novel drug scaffolds that can improve effectiveness and safety through drug conjugates is a promising approach. Consequently, drug conjugates constitute a dynamic field of study and advancement within medicinal chemistry. This research demonstrates the conjugation of diclofenac and mefenamic acid with sulfa drugs and their screening for urease inhibition. These conjugates' structural confirmation was performed using elemental analysis and spectroscopic methods, including IR, H NMR, and C NMR. Diclofenac conjugated with sulfanilamide (4), sulfacetamide (10), and mefenamic acid conjugated with sulfanilamide (12), and sulfamethoxazole (17) was found potent and demonstrated urease inhibition competitively, with IC (μM) values 3.59 ± 0.07, 5.49 ± 0.34, 7.92 ± 0.27, and 8.35 ± 0.26, respectively. Diclofenac conjugated with sulfathiazole (6), sulfamerazine (8), and sulfaguanidine (11), while mefenamic acid conjugated with sulfisoxazole (13), sulfathiazole (14), and sulfadiazine (15) exhibited a mixed mode of urease inhibition. The IC (μM) values were 16.19 ± 0.21, 9.50 ± 0.28, 4.35 ± 0.23, 15.86 ± 0.25, 14.80 ± 0.27, and 7.92 ± 0.27, respectively. Furthermore, molecular docking studies were employed to predict the binding pose of competitive inhibitors at the urease active site. These conjugates generated stable complexes with the urease protein observed through molecular dynamics (MD) simulations, where no conformational changes occurred throughout the simulations. These results highlight the potential for approved therapeutic molecule conjugates to give rise to new categories of pharmacological agents for urease inhibition. The structural similarity of sulfonamides with urea allows them to compete with urea for binding to the active site of the urease enzyme. Sulfonamides and nonsteroidal anti-inflammatory drugs (NSAIDs) can interact hydrophobically with the active site of the urease enzyme, which may disturb its structure and catalytic activity. Therefore, these conjugates may be helpful in the development of novel pharmacological agents for the treatment of a variety of illnesses in which the urease enzyme is involved.
PubMed: 38075833
DOI: 10.1021/acsomega.3c07275 -
International Journal of Pharmaceutics May 2016A comprehensive study on the dissolution properties of three co-amorphous sulfamerazine/excipient systems, namely sulfamerazine/deoxycholic acid, sulfamerazine/citric...
A comprehensive study on the dissolution properties of three co-amorphous sulfamerazine/excipient systems, namely sulfamerazine/deoxycholic acid, sulfamerazine/citric acid and sulfamerazine/sodium taurocholate (SMZ/DA, SMZ/CA and SMZ/NaTC; 1:1 molar ratio), is reported. While all three co-formers stabilize the amorphous state during storage, only co-amorphization with NaTC provides a dissolution advantage over crystalline SMZ and the reasons for this were analyzed. In the case of SMZ/DA extensive gelation of DA protects the amorphous phase from crystallization upon contact with buffer, but at the same time prevents the release of SMZ into solution. Disk dissolution studies showed an improved dissolution behavior of SMZ/CA compared to crystalline SMZ. However, enhanced dissolution properties were not seen in powder dissolution testing due to poor dispersibility. Co-amorphization of SMZ and NaTC resulted in a significant increase in dissolution rate, both in powder and disk dissolution studies.
Topics: Anti-Bacterial Agents; Chemistry, Pharmaceutical; Citric Acid; Crystallization; Deoxycholic Acid; Excipients; Solubility; Sulfamerazine; Taurocholic Acid
PubMed: 26992818
DOI: 10.1016/j.ijpharm.2016.03.023 -
Organic Letters Jun 2023Sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides by Ullmann-type coupling with inexpensive copper(I) iodide as the catalyst is...
Sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides by Ullmann-type coupling with inexpensive copper(I) iodide as the catalyst is reported. A broad scope of reaction inputs was demonstrated, including both aryl and alkyl sulfenamides and highly sterically hindered aryl and 5- and 6-membered ring heteroaryl iodides. Relevant to many bioactive high oxidation state sulfur compounds, the (hetero)arylation of -methyl sulfenamides is reported, including for complex aryl iodides. Smiles rearrangement of electron-deficient -heteroaryl sulfilimines is also disclosed.
Topics: Iodides; Sulfamerazine; Sulfur; Sulfur Compounds; Catalysis
PubMed: 37338140
DOI: 10.1021/acs.orglett.3c01874 -
The Journal of Organic Chemistry Mar 2017The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans...
The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans and benzoxepins. The reaction is catalyzed by a BINAM-based phosphoramide Lewis base catalyst which assists in the highly enantioselective formation of a thiiranium ion intermediate. The influence of nucleophile electron density, alkene substitution pattern, tether length and Lewis base functional groups on the rate, enantio- and site-selectivity for the cyclization is investigated. The reaction is not affected by the presence of substituents on the phenol ring. In contrast, substitutions around the alkene strongly affect the reaction outcome. Sequential lengthening of the tether results in decreased reactivity, which necessitated increased temperatures for reaction to occur. Sterically bulky aryl groups on the sulfenyl moiety prevented erosion of enantiomeric composition at these elevated temperatures. Alcohols and carboxylic acids preferentially captured thiiranium ions in competition with phenolic hydroxyl groups. An improved method for the selective C(2) allylation of phenols is also described.
Topics: Alkenes; Catalysis; Cyclization; Magnetic Resonance Spectroscopy; Phenols; Stereoisomerism; Sulfamerazine
PubMed: 28257203
DOI: 10.1021/acs.joc.7b00295 -
Oxidative Medicine and Cellular... 2017The results of epidemiological and pathophysiological studies suggest that type 2 diabetes mellitus (T2DM) may predispose to Alzheimer's disease (AD). The two conditions...
The results of epidemiological and pathophysiological studies suggest that type 2 diabetes mellitus (T2DM) may predispose to Alzheimer's disease (AD). The two conditions present similar glucose levels, insulin resistance, and biochemical etiologies such as inflammation and oxidative stress. The diabetic state also contributes to increased acetylcholinesterase (AChE) activity, which is one of the factors leading to neurodegeneration in AD. The aim of this study was to assess in vitro the effects of metformin, phenformin, and metformin sulfenamide prodrugs on the activity of human AChE and butyrylcholinesterase (BuChE) and establish the type of inhibition. Metformin inhibited 50% of the AChE activity at micromolar concentrations (2.35 mol/mL, mixed type of inhibition) and seemed to be selective towards AChE since it presented low anti-BuChE activity. The tested metformin prodrugs inhibited cholinesterases (ChE) at nanomolar range and thus were more active than metformin or phenformin. The cyclohexyl sulfenamide prodrug demonstrated the highest activity towards both AChE (IC = 890 nmol/mL, noncompetitive inhibition) and BuChE (IC = 28 nmol/mL, mixed type inhibition), while the octyl sulfenamide prodrug did not present anti-AChE activity, but exhibited mixed inhibition towards BuChE (IC = 184 nmol/mL). Therefore, these two bulkier prodrugs were concluded to be the most selective compounds for BuChE over AChE. In conclusion, it was demonstrated that biguanides present a novel class of inhibitors for AChE and BuChE and encourages further studies of these compounds for developing both selective and nonselective inhibitors of ChEs in the future.
Topics: Acetylcholinesterase; Butyrylcholinesterase; Cholinesterase Inhibitors; Diabetes Mellitus, Type 2; Female; GPI-Linked Proteins; Humans; Male; Metformin; Prodrugs; Sulfamerazine
PubMed: 28770024
DOI: 10.1155/2017/7303096 -
The Science of the Total Environment Mar 2020The present study investigated 16 residential, rural well sites and respective nearby streams in the Piedmont of North Carolina over three different seasons to determine...
The present study investigated 16 residential, rural well sites and respective nearby streams in the Piedmont of North Carolina over three different seasons to determine antibiotic presence and concentration. Fifteen antibiotics were detected in stream surface water, groundwater, and stream sediment compartments. Antibiotics detected representing penicillin, sulfonamide, macrolide, aminoglycoside, lincosamide, and quinolone groups. Sulfamethoxazole (SMX), sulfamerazine (SMR), danofloxacin (DAN), and erythromycin (ETM) were the most commonly detected among samples throughout the sampling period. Concentrations reported in the study ranged from 0 to 1740 ng/L in surface water and groundwater, and 0t378 μg/kg in stream sediment. There was a seasonal influence on antibiotic concentrations in each environmental compartment. Fall had the highest antibiotic concentrations for surface water and stream sediments overall, and groundwater concentrations were highest in the winter. Principal component analysis (PCA) was used to assess the correlation between environmental variables. Antibiotic concentrations correlated with groundwater pH, surface water pH, and surface water temperature. Non-metric multidimensional scaling (NMDS), used to display seasonal and environmental compartment data, demonstrated no discernible trend in the distribution of antibiotics over time. Human health risk assessments based on risk quotients (RQs). RQs from groundwater assessment shown no risk to children 6-11 years old, or adults 18 years old or older. Results from this study illustrate that the occurrence of antibiotics in streams and groundwater in the Piedmont of North Carolina is widespread and provide a basis for future studies investigating the occurrence of antibiotics in rural areas, especially where animal density is high. This work is important because it contributes to the paucity of information on antibiotic pollution in rural areas, and because it illustrates the importance of using a combined targeted and non-targeted approach to antibiotic pollution in streams and groundwater.
Topics: Adolescent; Adult; Animals; Anti-Bacterial Agents; Child; Environmental Monitoring; Groundwater; Humans; North Carolina; Rivers; Seasons; Water Pollutants, Chemical
PubMed: 32050361
DOI: 10.1016/j.scitotenv.2019.136286