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Structural effects of sulfonamides on the proliferation dynamics of sulfonamide resistance genes in the sequencing batch reactors and the mechanism

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Journal of Environmental Sciences 2024年第1期135卷 161-173页

作者： Ligui Wu Mingyu Wang Lingling Rong Wenbiao Wang Linwei Chen Qiaofeng Wu Haoyu Sun Xiangfeng Huang Xiaoming Zou College of Environmental Science and Engineering Tongji UniversityShanghai 200092China School of Life Science Jinggangshan UniversityJi’an 343009China Key Laboratory of Organic Compound Pollution Control Engineering(MOE) School of Environmental and Chemical EngineeringShanghai UniversityShanghai 200444China Fuzhou Urban and Rural Construction Group Co.Ltd. Fuzhou 350007China

Antibiotic resistance genes(ARGs)can be easily promoted by antibiotics,however,the structural effects of antibiotics on the proliferation of ARGs dynamic and the associated mechanisms remain obscure in,especially,activated sludge sequencing batch reactors.In the present study,the effects of 9 sulfonamides(SAs)with different structures on the proliferation dynamic of sulfonamide resistance genes(Suls)in the activated sludge sequencing batch reactors and the corresponding mechanisms were determined(30 days),and the results showed that the largest proliferation value(ΔA^(R))of Suls dynamic for SAs(sulfachloropyridazine)was approximately 2.9 times than that of the smallest one(sulfadiazine).The proliferation of Suls was significantly related to the structural features(minHBint6,SssNH,SHBd and SpMax2_Bhm)that represent the biological activity of SAs.To interpret the phenomenon,a mechanistic model was developed and the results indicated that the biodegradation of SAs(T_(1/2))rather than conjugative transfer frequency or mutation frequency tends to be the key process for affecting Suls proliferation.T_(1/2)was proved to be dependent on the interactions between SAs and receptors(E_(binding)),the cleavage mode(bond dissociation energy),and the site of nucleophilic assault.Besides,the metagenomic analysis showed that SAs posed significant effect on antibiotic resistome and Tnp31 played a vital role in the proliferation of Suls.Overall,our findings provide important insight into a theoretical basis for understanding the structural effects of SAs on the proliferation of ARGs in SBR systems.

关键词： Activated sludge sulfonamides Suls Proliferation Mechanism

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Electrochemical Dearomative Spirocyclization of N-Acyl sulfonamides in a Continuous-Flow Cell

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Chinese Journal of Chemistry 2024年第9期42卷 980-984页

作者： Ting Liu Zhaojiang Shi Yaofeng Yuan Yuqi Lin Ke-Yin Ye Key Laboratory of Molecule Synthesis and Function Discovery(Fujian Province University) College of ChemistryFuzhou University FuzhouFujian350108China

The development of efficient and sustainable methods to obtain spirocyclic compounds is of significance as these structures are widely found in pharmaceuticals and agrochemicals.Herein,we disclose an electrochemical dearomative spirocyclization of N-acyl sulfonamides in a continuous-flow cell.The reaction is simple and efficient without external catalysts or supporting electrolytes and could be applied in a decagram-scale synthesis.

关键词： Electrochemistry Continuous-flow Dearomatization Spirocyclization sulfonamides Cyclization Methodology and reactions

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Palladium-Catalyzed[4+2]and[6+2]Dipolar Cycloadditions for the Construction of Benzo[d]isothiazole 1,1-Dioxide Fused 1,3-Oxazinanes and 1,3-Oxazocanes

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Chinese Journal of Chemistry 2024年第8期42卷 829-834页

作者： Lei Chen Hongling Xie Yu Xue Zhengyu Han Jianwei Sun Hai Huang Jiangsu Key Laboratory of Advanced Catalytic Materials&Technology School of Petrochemical EngineeringChangzhou UniversityChangzhouJiangsu213164 China Department of Chemistry The Hong Kong University of Science and TechnologyClear Water BayKowloonHong Kong SARChina

Comprehensive Summary,The Pd-catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic compounds.This study developed the dipolar[4+2]and[6+2]cycloaddition reactions of benzo[d]isothiazole 1,1-dioxides(BDs)leading to the synthesis of BD-fused 1,3-oxazinane and 1,3-oxazocane derivatives,respectively.In particular,the synthesis of BD-fused 1,3-oxazinanes demonstrated regio-and enantioselective characteristics,resulting in products with good yields,enantioselectivity and regioselectivity(if applicable).Furthermore,the[6+2]cycloaddition reaction developed in this work represented the first strategy for the synthesis of medium-sized ring compounds based on BDs.

关键词： Cycloaddition 1,3-Oxazinanes 1,3-Oxazocanes Medium-ring compounds Stereochemistry N-Heterocycles sulfonamides Enantioselectivity Asymmetricsynthesis

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Biochemical responses of the freshwater microalga Dictyosphaerium sp. upon exposure to three sulfonamides

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Journal of Environmental Sciences 2020年第11期32卷 141-148页

作者： Shan Chen Jiayuan Li Wenbo Feng Mingzhe Yuan Wei Zhang Houtao Xu Xiaoyan Zheng Liqing Wang Centre for Research on Environmental Ecology and Fish Nutrient of the Ministry of Agriculture Key Laboratory of Exploration and Utilization of Aquatic Genetic ResourcesMinistry of EducationShanghai Ocean UniversityShanghai 201306China School of Agriculture and Biology Shanghai Jiao Tong UniversityShanghai 200240China Shanghai Aquatic Environmental Engineering Co. LtdShanghai 200090China

sulfonamides(SAs)are common antimicrobial drugs,which are frequently detected in surface water systems,and are difficult to degrade,posing a potential threat to the aquatic environment.However,little is known about the potential adverse effects of SAs on nontarget organisms(e.g.,microalgae)in the aquatic ecosystem.In this study,the effect of SAs(sulfadiazine(SD),sulfamerazine(SM1),and sulfamethazine(SM2)at 1,5,20,and 50 mg/L concentrations,respectively)on the freshwater microalga Dictyosphaerium sp.was investigated,with respect to changes of biomass and chlorophyll a content and induction of extracellular polymer substances(EPS),including protein and polysaccharide contents.At the same time,the residue of SAs was determined.The results showed that Dictyosphaerium sp.was tolerant to the three SAs,and the chlorophyll a content in Dictyosphaerium sp.significantly decreased on day 7,followed by a"compensation phenomena".The increase in protein and polysaccharide contents played a defensive role in Dictyosphaerium sp.against antibiotic stress,and there was a strong positive correlation between polysaccharide contents and antibiotic concentrations.Dictyosphaerium sp.exhibited 35%–45%,30%–42%,and 26%–51%removal of SD,SM1,and SM2,respectively.This study is helpful to understand the changes of EPS in the defense process of microalgae under the action of antibiotics,and provides a new insight for the ecological removal of antibiotic pollution in natural surface water system.

关键词： sulfonamides Dictyosphaerium Tolerance Polysaccharide Removal

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Gold immunochromatographic sensor for the rapid detection of twenty-six sulfonamides in foods

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Nano Research 2017年第8期10卷 2833-2844页

作者： Yanni Chen Liqiang Liu Liguang Xu Shanshan Song Hua Kuang Gang Cui Chuanlai Xu State Key Laboratory of Food Science and Technology Jiangnan University Wuxi 214122 China School of Food Science and Technology Jiangnan University Wuxi 214122 China

A gold immunochromatographic sensor （GICS） was developed for the rapid detection of 26 sulfonamides in honey samples. The sensor was based on a group-specific monoclonal antibody （mAb） that can recognize all 26 sulfonamides. Three haptens （hapten I with a thiazole ring, hapten 2 with a benzene ring, and hapten 3 with a straight carbon chain） were used for antigen preparation. With hybridoma technology, a group-specific mAb was screened with a 50% maximal inhibitory concentration （IC50） against sulfathizole （STZ） and the other 25 analogues ranging from 0.08 to 90.18 ng/mL. Mono-dispersed gold nanoparticles were conjugated with the mAb to develop the lateral immunochromatographic strip. A labeled antibody concentration of 0.1 pg/mL and a coating antigen concentration of 0.2 μg/mL in the test line were chosen for strip preparation. Under optimized conditions, the visual limits of detection （vLOD） for the concentrations of STZ, sulfamethoxazole, sulfamethizole, sulfadiazine, sulfamerazine, sulfadimethoxine, sulfamonomethoxine, sulfameter, sulfamethoxypyridazine, and sulfachloropyridazine were 5, 0.25, 0.25, 10, 5, 10, 25, 2.5, 5, 0.25, and 10 μg/kg, respectively. Scanner analysis in honey samples revealed good performance for detection of the 26 sulfonamides. Commercial honey samples were tested with the sensor and positive results were confirmed with high-performance liquid chromatography. The proposed strip sensor provides a convenient method for the rapid and reliable determination of sulfonamides pollutants in honey samples.

关键词： sulfonamides gold immunochromatographic sensor monoclonal antibody honey samples

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NH4I-Catalyzed Synthesis of sulfonamides from Arylsufonylhydrazides and Amines

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Chinese Journal of Chemistry 2016年第4期34卷 359-362页

作者： Hui Yu Yonghao Zhang Department of Chemistry Tongji University 1239 Siping Road Shanghai 200092 China

A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I （20 mol%） as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to goo... 详细信息

关键词： sulfonamides arylsulfonyl hydrazides Amines TBHP oxidative coupling

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Determination of fluoroquinolones, sulfonamides, and tetracyclines multiresidues simultaneously in porcine tissue by MSPD and HPLC-DAD

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Journal of Pharmaceutical Analysis 2012年第1期2卷 76-81页

作者： Hu Yu, Hui Mu, Ying-Mei Hu Chemistry Department of Science School, Xi’an Jiaotong University, Xi’an 710049, China Chemistry Department of Science School Xi'an Jiaotong University Xi'an 710049 China.

An efficient method is provided to detect simultaneously some important veterinary drugs from different classes in highly complex animal tissue matrix. This method using matrix solid-phase dispersion (MSPD) and high performance liquid chromatography (HPLC) with diode array detection (DAD) is developed to effectively determine two fiuoroquinolones (enoxacin and lomefioxacin), two sulfonamides (sulfanilamide and sulfamethoxazole) and one tetracycline (tetracycline) simultaneously in porcine tissues. In the process, MSPD methodology was used to treat samples, washed by n-hexane to remove lipid, eluted the analytes with acetonitrile–dichloromethane (1:1, v/v). Solvent acetonitrile and solvent acetic acid (0.1%) were combined in a gradient. HPLC–DAD analysis of the tissue samples was performed within 15 min at a fiow rate of 1.0 mL/min. The results showed that a recovery at 0.1, 0.5 and 1.0 mg/g fortification levels ranged from 80.6% to 99.2% with satisfactory relative standard deviations (RSDs) (below 6.1%, nfi3) and the limits of quantitation (LOQ) ranged from 7 mg/kg to 34 mg/kg in porcine tissues. Utilization of the method in successfully simultaneous analysis of porcine tissue incurred with veterinary drug multiresidues is described.

关键词： Matrix solid-phase dispersion High performance liquid chromatography Fluoroquinolones sulfonamides Tetracyclines Multiresidues

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Adsorption of sulfonamides on lake sediments

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Frontiers of Environmental Science & Engineering 2013年第4期7卷 518-525页

作者： Zhenxing ZHONG Jian XU Yuan ZHANG Lei LI ChangshengGUO Yan HE Wenhong FAN Beiping ZHANG State Key Laboratory of Environmental Criteria and Risk Assessment Chinese Research Academy of Environmental Sciences Beijing 100012 China School of Environmental Science and Engineering Huazhong University of Science & Technology Wuhan 430074 China Laboratory of Riverine Ecological Conservation and Technology Chinese Research Academy of Environmental Sciences Beijing 100012 China Department of Environmental Science and Engineering School of Chemistry and Environment Beihang University Beijing 100191 China

sulfonamides （SAs） are one class of the most widely used antibiotics around the world. Their fate and transport in the aquatic environment is of great concern. In this study, adsorption of four SAs--sulfadiazine （SD）, sulfamethoxazole （SMZ）, sulfadimethoxine （SDM） and sulfamethazine （SM2）---in single-solute and multi-solute systems on sediments of Dianchi （DC） Lake and Taihu （TH） Lake, China was investigated with batch experi- ments. In the single-solute adsorption system, the Langmuir model and the dual-mode model described the adsorption process better than the Freundlich model. Model fitness was better on DC sediment than on TH sediment. The order of adsorption capacity approximately followed a decreasing order of SDM ~ SD 〉 SM2 〉 SMZ on both sediments, which was likely attributed to the distinctly different water solubility of the four SAs. In the multi-solute system, the order of adsorption capacity was SM2 〉 SDM 〉 SD 〉 SMZ, which was probably related to the compound speciation caused by the pH values of the experimental solution. In the multi-solute system, both competitive and cooperative adsorption played important roles in the adsorption of sulfonamides on sediments.

关键词： sulfonamides sediments competitive adsorption cooperative adsorption

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Survey of Tetracyclines, sulfonamides, Sulfamethazine, and Quinolones in UHT Milk in China Market

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Journal of Integrative Agriculture 2013年第7期12卷 1300-1305页

作者： HAN Rong-wei ZHENG Nan WANG Jia-qi ZHEN Yun-peng LI Song-li YU Qun-li College of Food Science and Engineering Gansu Agricultural University State Key Laboratory of Animal Nutrition Institute of Animal Science Chinese Academy of Agricultural Sciences College of Food Science and Engineering Qingdao Agricultural University

This study surveyed 180 samples of ultra high temperature （UHT） milk of four top Chinese dairy brands collected in the 25 cities in China in June 2011, and assessed their contamination with antibiotics, using the ELISA method. The percentages of tetracyclines, sulfonamides, sulfamethazine, and quinolones detected in the samples were 0, 16.7, 40.6, and 100%, respectively. The maximum concentrations of the tetracyclines, sulfonamides, sulfamethazine and quinolones in UHT milk samples were 〈1.5, 26.2, 22.6, and 58.8 μg kg-1, respectively. None of the samples exceeded the maximum residue levels （MRLs） for these four veterinary drugs, according to the regulations set by China, the European Union （EU） and the Codex Alimentarius Commission （CAC）.

关键词： survey tetracyclines sulfonamides sulfamethazine quinolones UHT milk China market

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Malaria parasite carbonic anhydrase:inhibition of aromatic/heterocyclic sulfonamides and its therapeutic potential

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Asian Pacific Journal of Tropical Biomedicine 2011年第3期1卷 233-242页

作者： Sudaratana R Krungkrai Jerapan Krungkrai Unit of Biochemistry Department of Medical Science.Faculty of ScienceRangsit University Department of Biochemistry Faculty of MedicineChulalongkorn University

Plasmodium falciparum(P.falciparum) is responsible for the majority of life-threatening cases of human malaria,causing 1.5-2.7 million annual deaths.The global emergence of drug-resistant malaria parasites necessitates identification and characterisation of novel drug targets and their potential inhibitors.We identified the carbonic anhydrase(CA) genes in P.falciparum.The pfGA gene encodes an α-carbonic anhydrase,a Zn^(2+)-metalloenzme,possessing catalytic properties distinct from that of the human host CA enzyme.The amino acid sequence of the pfCA enzyme is different from the analogous protozoan and human enzymes.A library of aromatic/heterocyclic sulfonamides possessing a large diversity of scaffolds were found to be very good inhibitors for the malarial enzyme at moderate-low micromolar and submicromolar inhibitions.The structure of the groups substituting the aromatic-ureido-or aromatic-azomethine fragment of the molecule and the length of the parent sulfonamide were critical parameters for the inhibitory properties of the sulfonamides.One derivative,that is,4-(3,4-dichlorophenylureido)thioureidobcnzcnesulfonamide(compound 10) was the most effective in vitro Plasmodium falciparum CA inhibitor,and was also the most effective antimalarial compound on the in vitro P.falciparum growth inhibition.The compound 10 was also effective in vivo antimalarial agent in mice infected with Plasmodium berghei,an animal model of drug testing for human malaria infection. It is therefore concluded that the sulphonamide inhibitors targeting the parasite CA may have potential for the development of novel therapies against human malaria.

关键词： Malaria Plasmodium falciparum Carbonic anhydrase Carbonic anhydrase inhibitor Aromalic/heterocyclic sulfonamides Antimalarial agents Drug target Parasitic disease

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