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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 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 -
Environmental Research Mar 2022A heterogeneous electro-Fenton (hetero-EF) system can effectively broaden the applicable pH range, although the decreased electrogeneration efficiency of HO at elevated...
A heterogeneous electro-Fenton (hetero-EF) system can effectively broaden the applicable pH range, although the decreased electrogeneration efficiency of HO at elevated pH (especially neutral conditions) is unfavorable for the efficient removal of organic pollutants. Herein, a tannic acid-Fe complex derivative-modified carbon felt (TFD@CF) cathode was prepared for hetero-EF treatment of organic pollutants over a wide pH range. Interestingly, the as-prepared hetero-EF cathode could act as a pH regulator that acidified the solution over a wide pH range. As expected, the TFD@CF cathode exhibited excellent hetero-EF activity for the removal of diverse organic pollutants (such as methyl orange, methylene blue, sulfamerazine, bisphenol A and 2,4-dichlorophenoxyacetic acid) at neutral and even alkaline pH (removal efficiency >90 %). A total of 2.98 kWh kg COD with 83.2 % COD removal could be achieved by the TFD@CF cathode for the treatment of actual textile dyeing secondary wastewater. Electrochemical characterizations proved that the TFD@CF cathode had excellent electrochemical properties with improved electron transfer ability and a well-pronounced Fe(III) electroreductive response. Meanwhile, more acidic groups were newly generated during the electrochemical reaction (an increase of 30.1 %), thus dissociating more H into solution. The identification of reactive oxygen species suggested that OH and O could be responsible for the removal of organic pollutants in the TFD@CF EF system. These interesting findings may provide new insights into the design of multifunctional hetero-EF cathodes for the removal of refractory organic pollutants.
Topics: Electrodes; Environmental Restoration and Remediation; Ferric Compounds; Hydrogen Peroxide; Hydrogen-Ion Concentration; Oxidation-Reduction; Tannins; Water Pollutants, Chemical
PubMed: 34487696
DOI: 10.1016/j.envres.2021.111994 -
Journal of Chromatography. A Jul 2022Sulfonamides (SAs) were widespread in animal-derived food at trace level, which could trigger hazards to human health. Herein, electric field enhanced thin-film...
Sulfonamides (SAs) were widespread in animal-derived food at trace level, which could trigger hazards to human health. Herein, electric field enhanced thin-film microextraction (EE-TFME) was developed based on carbon cloth (CC) modified with metal-organic frameworks (MOFs) for extraction of SAs (sulfadiazine, sulfathiazole, sulfamerazine, sulfadimidine, sulfamethoxazole and sulfisoxazole), which were a series of polar analytes. MIL-101(Cr) was in situ synthesized on CC via hydrothermal reaction and then was used as positive electrode in EE-TFME for adsorption of SAs. Compared with traditional TFME, EE-TFME shortened extraction equilibrium time from 30 min to 15 min. Coupled with high-performance liquid chromatography (HPLC), the limits of detection (LODs) were 2.5-4.5 µg/L, while the repeatability and intermediate precision was lower than 9.1%. Quantitative determination of SAs in extracts of animal-derived samples, such as honey, pork, chicken and milk, was achieved with recoveries from 81.7% to 114.2%. The developed MOF/CC-based EE-TFME has a great potential in rapid extraction of similar polar or ionic analytes from complex food matrices.
Topics: Adsorption; Animals; Carbon; Chromatography, High Pressure Liquid; Limit of Detection; Metal-Organic Frameworks; Sulfonamides
PubMed: 35598537
DOI: 10.1016/j.chroma.2022.463120 -
Journal of Separation Science May 2022A magnetic solid phase extraction method based on magnetic covalent organic frameworks (TpBD@Fe O ; 2,4,6-triformylphloroglucinol (Tp) and benzidine (BD)) combined with...
A magnetic solid phase extraction method based on magnetic covalent organic frameworks (TpBD@Fe O ; 2,4,6-triformylphloroglucinol (Tp) and benzidine (BD)) combined with high performance liquid chromatography has been developed to detect the sulfonamides including sulfadiazine, sulfamerazine, sulfamethazine, and sulfamethoxazole in milk and meat. TpBD@Fe O were synthesized at room temperature under mild reaction conditions with a simple and rapid operation. The TpBD@Fe O exhibited higher extraction efficiency because of the π-π and electrostatic interactions between the benzene ring structure of the TpBD and the sulfonamide molecules. The extraction conditions including the dosage of adsorbents, the type and dosage of eluent, the elution time, and the pH of the sample solution were fully optimized. The detection results showed good linearity over a wide range (50-5 × 10 ng/mL) and low detection limits (3.39-5.77 ng/mL) for the sulfonamide targets. The practicability of this magnetic solidphase extraction-high-performance liquid chromatography method was further evaluated by analyzing milk and meat samples, with recoveries of the targets of 71.6-110.8% in milk and 71.9-109.7% in pork. The successful detection of sulfonamides residues has demonstrated the TpBD@Fe O excellent practical potential for analyzing pharmaceutical residues in animal-derived foods.
Topics: Animals; Chromatography, High Pressure Liquid; Food Contamination; Limit of Detection; Magnetic Phenomena; Metal-Organic Frameworks; Solid Phase Extraction; Sulfonamides; Temperature
PubMed: 35178864
DOI: 10.1002/jssc.202100978 -
Saudi Journal of Biological Sciences May 2021Symbiotic bacteria play vital roles in the survival and health of marine sponges. Sponges harbor rich, diverse and species-specific microbial communities. Symbiotic...
Symbiotic bacteria play vital roles in the survival and health of marine sponges. Sponges harbor rich, diverse and species-specific microbial communities. Symbiotic marine bacteria have increasingly been reported as promising source of bioactive compounds. A culturomics-based study was undertaken to study the diversity of bacteria from marine sponges and their antimicrobial potential. We have collected three sponge samples i.e. , (soft coral) and from north region (Obhur) of Red Sea, Jeddah Saudi Arabia. Total of 144 bacterial strains were isolated from three marine sponges using culture dependent method. Screening of isolated strains showed only 37 (26%) isolates as antagonists against oomycetes pathogens ( and ). Among 37 antagonistic bacteria, only 19 bacterial strains exhibited antibacterial activity against human pathogens (Methicillin-resistant (MRSA) ATCC 43300 ATCC 27853, ATCC 8739, ATCC 29212). Four major classes of bacteria i.e , and were recorded from three marine sponges where was dominant class. One potential bacterial strain sp. EA423 was selected for identification of bioactive metabolites using GC and LC-MS analyses. Bioactive compounds Sulfamerazine, Metronidazole-OH and Ibuprofen are detected from culture extract of strain sp. EA423. Overall, this study gives insight into composition and diversity of antagonistic bacterial community of marine sponges and coral from Red Sea and presence of active metabolites from potential strain. Our results showed that these diverse and potential bacterial communities further need to be studied to exploit their biotechnological significance.
PubMed: 34025160
DOI: 10.1016/j.sjbs.2021.03.042 -
Talanta Jun 2024Sulfonamides (SAs) is a class of antibiotics that extensively used for treating infectious diseases in livestock industries and aquaculture. Thus, it is urgent need to...
Isolation of aptamers with excellent cross-reactivity and specificity to sulfonamides towards a ratiometric fluorescent aptasensor for the detection of nine sulfonamides in seafood.
Sulfonamides (SAs) is a class of antibiotics that extensively used for treating infectious diseases in livestock industries and aquaculture. Thus, it is urgent need to obtain the bio-receptor, which has excellent cross-reactivity and specificity to SAs, for developing high-throughput methods for the determination of multiple SAs even all commonly-used SAs, to realize the quick screening/detection of total SAs in animal-derived foods. We herein isolated several SAs-specific cross-reactive aptamers by using a library-immobilized SELEX with multi-SAs parallel selection strategy. Two of the isolated aptamers (Sul-01 and Sul-04) can specifically recognize and bind seven SAs respectively with higher binding affinity and no interference of non-sulfonamide antibiotics, and thus can be applied as bio-receptors for developing high-throughput aptasensors for the quick screening/detection of multiple SAs. By using the mixture of Sul-01 and Sul-04 as bio-receptor, a ratiometric fluorescent aptasensor was created for the quick detection of nine SAs including sulfamethoxydiazine (SMD), sulfapyridine (SPD), sulfaquinoxaline (SQ), sulfathiazole (ST), sulfamonomethoxine (SMM), sulfamerazine (SMR), sulfaguanidine (SG), sulfamethazine (SMZ) and sulfadiazine (SD) with a detection limit (LOD) of 0.10-0.50 μM, or total of above nine SAs with a LOD of 0.20 μM. The fluorescent aptasensor was successfully applied to detect each or total of SMD, SPD, SQ, ST, SMM, SMR, SG, SMZ and SD in fish samples with a recovery of 83 %-92 % and a relative standard deviation (RSD, n = 5) < 5 %. This study not only provided several promising bio-receptors for the development of diverse high-throughput aptasensors to achieve the quick screening of multiple SAs residues, but also provided a simple, stable and sensitive method for the quick screening of SMD, SPD, SQ, ST, SMM, SMR, SG, SMZ and SD in seafood.
PubMed: 38852344
DOI: 10.1016/j.talanta.2024.126380 -
Waste Management (New York, N.Y.) Aug 2022Antibiotics and antibiotic resistance genes (ARGs) in sewage sludge can cause high ecotoxicological risks in the environment and public health concerns. The aims of this...
Antibiotics and antibiotic resistance genes (ARGs) in sewage sludge can cause high ecotoxicological risks in the environment and public health concerns. The aims of this study were to establish enzymatic integrated in-situ advanced anaerobic digestion (AAD) by adding cellulase and papain as well as the two enzymes combined with zero valent iron (ZVI) directly into the anaerobic digesters to explore the removal of antibiotics and ARGs under the mesophilic condition (35 °C). The methane production potential during in-situ AAD was effectively improved. Papain and cellulase at 30 mg/gTSS were most effective in improving antibiotic removal. The removal of sulfamerazine (SMZ) and sulfadiazine (SMR) could reach 89.10 % and 71.75 %. Combined enzymes with ZVI also enhanced the removal of all target antibiotics, especially roxithromycin (ROX), SMZ and SMR most significantly. Except for sul1, tetA and tetB, the removal of ARGs by papain reached 6.33 %-82.15 %. The addition of cellulase effectively improved tetA removal. The combination of biological enzymes further enhanced the removal of qnrS and ermX. The tetG, tetB, sul3, ermX, ermT, qnrS, and aac(6')-IB-CR by combined enzymes with ZVI could even not be detected after digestion. Addition of papain, cellulase, and ZVI caused variations in the dominant bacteria. All target antibiotics presented significant positive correlations with the genera norank_f__Bacteroidetes_vadinHA17, norank_f__norank_o__SJA-15, norank_f__norank_o__Aminicenantales. Redundancy analysis showed archaea Methanosaeta and Candidatus_ Methanoacidiosum genera greatly contributed to antibiotics removal with the combination of enzymes and ZVI. Co-occurrence network analysis indicated the removal of ARGs was mainly based on the changes of existence of host bacteria.
Topics: Anaerobiosis; Anti-Bacterial Agents; Bacteria; Cellulases; Drug Resistance, Microbial; Genes, Bacterial; Iron; Papain; Sewage
PubMed: 35926402
DOI: 10.1016/j.wasman.2022.07.020 -
Ecotoxicology and Environmental Safety Sep 2022Sulfonamide antibiotics (SAs) are widely used in medicine, animal husbandry and aquaculture, and excessive intake of SAs may pose potential toxicity to organisms. The...
Sulfonamide antibiotics (SAs) are widely used in medicine, animal husbandry and aquaculture, and excessive intake of SAs may pose potential toxicity to organisms. The toxicological mechanisms of two classical SAs, sulfamerazine (SMR) and sulfamethoxazole (SMT), were investigated by molecular docking, DFT and multi-spectroscopic techniques using HSA and BSA as model proteins. The quenching of HSA/BSA endogenous fluorescence by SMR was higher than that by SMT due to the stronger binding effect of the pyrimidine ring on HSA/BSA compared to the oxazole ring, and that result was consistent with that predicted by DFT calculations. Thermodynamic parameters show that the binding of SAs to HSA/BSA is an exothermic process that proceeds spontaneously (ΔG < 0). Marker competition experiments illustrate that the binding site of SMR/SMT on serum albumin is located in subdomain IIIA. The combination of SAs and HSA/BSA is mainly realized by hydrogen bond and hydrophobic interaction, and the concept is also supported by molecular modeling. The reduced α-helix content of HSA/BSA induced by SMR/SMT indicates a greater stretching of the protein α-helix structure of the SMR/SMT-HSA/BSA. The results could provide useful toxicological information on the hazards of SAs in response to growing concern that SAs may pose a toxic threat to organisms.
Topics: Animals; Anti-Bacterial Agents; Binding Sites; Circular Dichroism; Density Functional Theory; Molecular Docking Simulation; Protein Binding; Serum Albumin, Bovine; Spectrometry, Fluorescence; Sulfanilamide; Sulfonamides; Thermodynamics
PubMed: 35987082
DOI: 10.1016/j.ecoenv.2022.113979 -
Spectrochimica Acta. Part A, Molecular... Jan 2024Sulfa drugs are frequently used to treat infections, particularly in antibiotic resistant people. There are several techniques available to determine sulfa drugs,...
Sulfa drugs are frequently used to treat infections, particularly in antibiotic resistant people. There are several techniques available to determine sulfa drugs, however, they are laborious operation, reagent consumption, expensive, and need specialized types of equipment. Here, a new, very simple and inexpensive paper-based analytical device described for the determination of five sulfa drugs: sulfacetamide, sulfadiazine, sulfamerazine, sulfamethoxazole, and sulfathiazole in pharmaceutical preparations. The method is a one-step reaction, based on the colorimetric reaction between acid-hydrolyzed sulfa drugs and 4-dimethylaminobenzaldehyde. Using a smartphone, the RGB value of color intensity was used as an analytical signal. The paper-based device displayed linear ranges of 0.10-5.00 µg mL, linear correlations ranging from 0.9903 to 0.9972, limits of detection 0.0030 to 0.0082 µg mL, and RSD of ≤0.258 under optimal conditions. The suggested approach was applied for determining five sulfa drugs in pharmaceutical formulations. This approach is appropriate for pharmaceutical applications since it is inexpensive, simple to utilize, sensitive, and selective.
PubMed: 37683435
DOI: 10.1016/j.saa.2023.123336