Currently,triazole sulfonamide fungicide could be used to effectively control cucumber downy mildew(CDM),caused by Pseudoperonospora cubensis.In this study,a series of triazole sulfonamide derivatives containing diphe...Currently,triazole sulfonamide fungicide could be used to effectively control cucumber downy mildew(CDM),caused by Pseudoperonospora cubensis.In this study,a series of triazole sulfonamide derivatives containing diphenyl ether(DE)fragment were designed and synthesized.All target compounds were evaluated for their fungicidal activity against four oomycete diseases.Compound 10b showed the best activity against CDM with 40%control efficacy at 0.78 mg/L,which was the same as amisulbrom.Meanwhile,compounds 10d and 10h showed good inhibitory activity against Peronophythora litchii and compounds 10e,10f,10l and 10q showed good inhibitory activity against Phytophthora infestans.The results of computational chemistry showed that compound 10b had the same binding mode as amisulbrom and formed hydrogen bonds with the residues Gln9,His189 and Ash217.Compound 10b could be further investigated as a potential fungicide candidate.This study also provides a useful optimization strategy for the design of novel fungicides against CDM.展开更多
Obtaining the sulfonamides(SAs)concentrations in the water body and sediment bulk was a prerequisite to reveal their transport and partitioning behavior in sediment-water environments and accurately assess their ecolo...Obtaining the sulfonamides(SAs)concentrations in the water body and sediment bulk was a prerequisite to reveal their transport and partitioning behavior in sediment-water environments and accurately assess their ecological risk.In the present study,the influences of multifactor interactions on the performance of o-DGTs with XAD-18 binding gels were analyzed by central combination experiments and response surfaces analysis,in which the target compounds were 9 SAs.The results indicated that dissolved organic matter(DOM),pH,and suspended particulate matter(SS)had significant effects on the o-DGT sampling,whereas this o-DGT was independent of the ionic strength(IS).Concentning the composite influence of the four factors,the interaction between DOM and SS posed the most significant effect on all 9 SAs compounds.Subsequently,an o-DGT and DIFSmodel was applied to explore the SAs migration between the water-sediments interface.The difference between desorption rate(k_(b))and adsorption rates(k_(f))values suggested that the kinetics of SAs was dominated by adsorption.Moreover,the short-term sediment-water partitioning of SAs was clarified on the basis of distribution coefficient(K_(dl))for the labile SAs,among which the sulfadiazine(SDZ)had the largest labile pool.The ability of sediments to release SAs to the liquid phase as a sink was determined by response time(T_(c)).Among the 9 SAs,the longterm release of soseulfamethoxypyridazine(SMP)from the solid phase of sediments would have a potential risk to the aquatic environment,to which more attention should be paid in the future.展开更多
On the basis of the Michael-addition mechanism of classical proteasome inhibitors, six dipeptide vinyl sulfonamide and dipeptide vinyl sulfonate derivatives were designed and synthesized. Moreover, an efficient method...On the basis of the Michael-addition mechanism of classical proteasome inhibitors, six dipeptide vinyl sulfonamide and dipeptide vinyl sulfonate derivatives were designed and synthesized. Moreover, an efficient method for the synthesis of g-amino vinyl sulfonamides, key intermediates to the target molecules, was developed via the Wittig-Horner reaction of peptide aldehyde with Wittig reagents derived from methanesulfonamides.展开更多
Objective Sulfanilamide,sulfadiazine,and dapsone were the first sulfonamides to be used to treat malaria by disrupting the folate biosynthesis process,which is essential for parasite survival.Therefore,we aimed to syn...Objective Sulfanilamide,sulfadiazine,and dapsone were the first sulfonamides to be used to treat malaria by disrupting the folate biosynthesis process,which is essential for parasite survival.Therefore,we aimed to synthesize novel N-(2-arylaminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide derivatives through a rational drug design approach.Methods All compounds were synthesized by the conventional method,and the products were characterized by spectral analysis(1 H NMR and mass spectrometry).The progression of the reaction was monitored using thin-layer chromatography(TLC).All the derivatives were analyzed for their effective binding mode in the allosteric site of the plasmodium cysteine protease falcipain-2.Antibacterial and antifungal activities were determined using the broth dilution method.Results S6(N-(2-thiazol-4 yl)-acetyl-aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide and S9(N-(1 H-benzo[d]imidazol-2-yl)aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide formed five hydrogen bonds;S8(N-(2-1 H-imidazol-2 yl)aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide and S10(N-(1 H-benzo[d]imidazol-5-yl)aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide formed four hydrogen bonds with the allosteric site of the enzyme.Considering the docking scores and formation of hydrogen bonds with the target enzyme,the novel derivatives were processed for wet lab synthesis.All the newly synthesized derivatives were subjected to in vitro antimalarial,antifungal,and antibacterial activities.All the derivatives exhibited sufficient sensitivity to the Plasmodium falciparum strain compared to the standards.Moreover,compounds S9 and S10 showed the most potent dual antimicrobial and antimalarial activities.They also exhibited powerful molecular interactions in molecular docking studies.Conclusion Based on the above results,it was concluded that N-(2-arylaminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide derivatives have excellent biological potential to act as antimalarial,antifungal,and antibacterial agents.展开更多
A new series of sulfonamide flavone derivatives are designed as non-covalent inhibitors of proteasome assisted with computer-aided drug design （CADD）. The desired compounds were synthesized successfully and the biol...A new series of sulfonamide flavone derivatives are designed as non-covalent inhibitors of proteasome assisted with computer-aided drug design （CADD）. The desired compounds were synthesized successfully and the biological evaluation was subsequently accomplished. The results showed negligible improvement from our lead compound （IC50 for β5 subunit was 14.0 μM）. Thus, these flavone derivatives might be improved as potential 20S proteasome inhibitors.展开更多
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 p...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.展开更多
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 necessitate...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.展开更多
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 EL...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）.展开更多
The occurrence of antibiotics in the environment has recently raised serious concerns regarding their potential threat to human health and aquatic ecosystem. A new magnetic nanocomposite, Fe304@C （Fe304 coated with c...The occurrence of antibiotics in the environment has recently raised serious concerns regarding their potential threat to human health and aquatic ecosystem. A new magnetic nanocomposite, Fe304@C （Fe304 coated with carbon）, was synthesized, characterized, and then applied to remove five commonly-used sulfonamides （SAs） from water. Due to its combinational merits of the outer functionalized carbon shell and the inner magnetite core, Fe3O4@C exhibited a high adsorption affinity for selected SAs and a fast magnetic separability. The adsorption kinetics of SAs on Fe304 @ C could be expressed by the pseudo second-order model. The adsorption isotherms were fitted well with the Dual-mode model, revealing that the adsorption process consisted of an initial partitioning stage and a subsequent hole-filling stage. Solution pH exerted a strong impact on the adsorption process with the maximum removal efficiencies （74% to 96%） obtained at pH 4.8 for all selected SAs. Electrostatic force and hydrogen bonding were two major driving forces for adsorption, and electron-donor-acceptor interactions may also make a certain contribution. Because the synthesized Fe304@C showed comprehensive advantages of high adsorptivity, fast magnetic separability, and prominent reusability, it has potential applications in water treatment.展开更多
The aim of this work was to develop an automated on-line solid phase extraction(SPE)with liquid chromatography-tandem mass spectrometry method for the detection of fifteen sulfonamides in pork and fish samples.Samples...The aim of this work was to develop an automated on-line solid phase extraction(SPE)with liquid chromatography-tandem mass spectrometry method for the detection of fifteen sulfonamides in pork and fish samples.Samples were extracted with 0.2%formic acid acetonitrile solution,purified by on-line SPE device with HLB column,then separated by XBridge C18 column,using 0.1%formic acid solution and acetonitrile as the mobile phase.Mass spectrometric data was acquired under multiple reaction monitoring(MRM)mode using positive ionization electrospray.Internal standard method was used in the quantification,good linear relationship was got in range of 0.1–100 ng/mL and correlation coefficient was higher than 0.9990.The limits of detection were in the range of 0.125–2.00g/kg and the limits of quantitation were in the range of 0.250–5.00g/kg.Recoveries of the method were in range of 78.3%–99.3%,relative standard deviation were lower than 10%.The method was simple,sensitivity,and could be used for routine supervision and analysis of fifteen sulfonamides in pork and fish.展开更多
Surface-enhanced Raman scattering(SERS)spectroscopy has been employed as a rapid analysis technology for food security inspection recently.Nowadays,it is still a great challenge to rapidly quantify multiple trace anti...Surface-enhanced Raman scattering(SERS)spectroscopy has been employed as a rapid analysis technology for food security inspection recently.Nowadays,it is still a great challenge to rapidly quantify multiple trace antibiotics potentially abused in aquaculture industry.In this work,a magnetic Ti_(3)C_(2)T_(x)/Fe_(3)O_(4)/Ag substrate was prepared for the development of a reliable rapid SERS quantification method for multiple trace sulfonamides in aquatic products.This magnetic substrate had good uniformity,reproducibility,stability and SERS activity.Moreover,this substrate could integrate the magnetic separation-enrichment and matrix clean-up without cross contamination,which endowed it with good selectivity and antiinterference capability during real sample analysis.The electromagnetic enhancement and chemical enhancement mechanism of this magnetic substrate were studied in detail to reveal its good separationenrichment performance and SERS activity.Finally,a rapid SERS quantification method was established and practically applied for trace phthalic sulfathiazole(PST)and silver sulfadiazine(SSD)in aquatic products by using Ti_(3)C_(2)T_(x)/Fe_(3)O_(4)/Ag magnetic substrates.Trace PST and SSD could be actually detected and quantified as 55.9μg/kg and 64.0μg/kg in aquatic products,respectively.Good recoveries of 83.9%-116%with relative standard deviations(RSDs)of 0.5%-3.2%for PST and 80.2%-102%with RSDs of 1.3%-5.8%for SSD were obtained.This work proposed an efficient and reliable method for rapid quantification of trace multiple sulfonamides in complex aquatic samples during food security inspection.展开更多
[ Objective] This study was conducted to establish a new UPLC-MS method for simultaneous detection of sulfonanfides and chloramphenicols in honey. [ Method] In this experiment, 0.2% formic acid-acetonitrile was used a...[ Objective] This study was conducted to establish a new UPLC-MS method for simultaneous detection of sulfonanfides and chloramphenicols in honey. [ Method] In this experiment, 0.2% formic acid-acetonitrile was used as an extractant to simultaneously extract chloramphenicoJs and sulfonamides from drugs. The extract was then loaded and extracted with an efficient separation column Oasis PRIME HLB. After nitrogen blow-concentration and dissolution with mobile phase, the extract was loaded on UPLC and detected by MS. [ Resultl There was a good linear relation in the range of 0. 1 - 10 ng/ml for chloramphenicols, with a correlation coefficient of 0.991, while sulfonamides had a good linear relation in the range of 0.5 - 50 ng/ml. The lowest detection limit of chloramphenicols and sulfonamides were 0. 1 and 0.5 μg/kg, respectively. The recoveries were in the range of 82.50% - 101.2%, with RSD values in the range of 3.2% -4.0%. [ Conclusion] This method is simple and fast with low detection limit, high recovery and good reproducibility, and could be used for simultaneous detection of re- sidual chloramphenicols and sulfonamides in honey. Key words UHPLC-MS; Sulfonamides ; Chloramphenicols ; Honey展开更多
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 th...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.展开更多
By using the famous Wilkinson＇s catalyst, N-alkylation of sulfonamides can be easily realized under mild aerobic conditions by using alcohols as the alkylating reagent, giving monoalkylated sulfonamides in high yield...By using the famous Wilkinson＇s catalyst, N-alkylation of sulfonamides can be easily realized under mild aerobic conditions by using alcohols as the alkylating reagent, giving monoalkylated sulfonamides in high yields and selectivities with water produced as the only byproduct. This advantageous aerobic method is potentially general in substrate scope that it can also be applied to other amides, amines and alcohols.展开更多
Acetazolamide(molecular mass(MM),222)belongs to the class of sulfonamides(R-SO2-NH2)and is one of the strongest pharmacological inhibitors of carbonic anhydrase activity.Acetazolamide is excreted unchanged in the urin...Acetazolamide(molecular mass(MM),222)belongs to the class of sulfonamides(R-SO2-NH2)and is one of the strongest pharmacological inhibitors of carbonic anhydrase activity.Acetazolamide is excreted unchanged in the urine.Here,we report on the development,validation and biomedical application of a stable-isotope dilution GC-MS method for the reliable quantitative determination of acetazolamide in human urine.The method is based on evaporation to dryness of 50 mL urine aliquots,base-catalyzed derivatization of acetazolamide(d0-AZM)and its internal standard[acetylo-2H3]acetazolamide(d3-AZM)in 30 vol%pentafluorobenzyl(PFB)bromide in acetonitrile(60 min,30C),reconstitution in toluene(200 mL)and injection of 1-mL aliquots.The negative-ion chemical ionization(NICI)mass spectra(methane)of the PFB derivatives contained several intense ions including[M]‒at m/z 581 for d0-AZM and m/z 584 for d3-AZM,suggesting derivatization of their sulfonamide groups to form N,N-dipentafluorobenzyl derivatives(R-SO2-N(PFB)2),i.e.,d0-AZM-(PFB)2 and d3-AZM-(PFB)2,respectively.Quantification was performed by selected-ion monitoring of m/z 581 and 83 for d0-AZM-(PFB)2 and m/z 584 and 86 for d3-AZM-(PFB)2.The limits of detection and quantitation of the method were determined to be 300 fmol(67 pg)and 1 mM of acetazolamide,respectively.Intra-and inter-assay precision and accuracy for acetazolamide in human urine samples in pharmacologically relevant concentration ranges were determined to be 0.3%e4.2%and 95.3%e109%,respectively.The method was applied to measure urinary acetazolamide excretion after ingestion of a 250 mg acetazolamide-containing tablet(Acemit®)by a healthy volunteer.Among other tested sulfonamide drugs,methazolamide(MM,236)was also found to form a N,N-dipentafluorobenzyl derivative,whereas dorzolamide(MM,324)was hardly detectable.No GC-MS peaks were obtained from the PFB bromide derivatization of hydrochlorothiazide(MM,298),xipamide(MM,355),indapamide and metholazone(MM,366 each)or brinzolamide(MM,384).We demonstrate for the first time that sulfonamide drugs can be derivatized with PFB bromide and quantitated by GC-MS.Sulfonamides with MM larger than 236 are likely to be derivatized by PFB bromide but to lack thermal stability.展开更多
2-Cetyl-3-20 keto acid（N-ethyl perfluorinated octyl sulfonamide） N-ethyl ester was synthesized by the reaction of N-ethyl-N-hydroxyethyl perfluorinated octyl sulfonamide and alky ketene dimer. The experimental resul...2-Cetyl-3-20 keto acid（N-ethyl perfluorinated octyl sulfonamide） N-ethyl ester was synthesized by the reaction of N-ethyl-N-hydroxyethyl perfluorinated octyl sulfonamide and alky ketene dimer. The experimental results show that the yield of products can be 89% when the molar ratio of perfluorinated octyl sulfonamide to ketene dimer is 1 ： 1.1 and the reaction lasts about four hours at 80 ℃. The structure of the product was characterized by FTIR and ^1HNMR. The product can dissolve in polar solvents such as NMP, DMAC, THF, DMSO, CHCl3, and 10% weight-loss temperature measured by TGA is 202℃.展开更多
The electrochemical synthesis of some new sulfonamide derivatives was carried out via the electrochemical oxidation of 2,3-dihydrophthalazine-l,4-dione （1） in the presence of arylsulfinic acids （2a and 2b） as nucl...The electrochemical synthesis of some new sulfonamide derivatives was carried out via the electrochemical oxidation of 2,3-dihydrophthalazine-l,4-dione （1） in the presence of arylsulfinic acids （2a and 2b） as nucleophiles. The results show that, the electrogenerated phthalazine-l,4-dione （lox） participates in a Michael type addition reaction with 2a or 2b and via an EC mechanism to produce the corresponding sulfonamide derivatives. This method provides a one-pot procedure for the synthesis of new sulfonamide derivatives of potential biological significance in good yields without using toxic reagents at a carbon electrode in an environmentally friendly manner.展开更多
Aiming at the market demand for rapid detection of tetracyclines,fluoroquinolones and sulfonamides in milk,a golloidal gold immunochromatography test strip for simultaneous detection of tetracyclines,fluoroquinolones ...Aiming at the market demand for rapid detection of tetracyclines,fluoroquinolones and sulfonamides in milk,a golloidal gold immunochromatography test strip for simultaneous detection of tetracyclines,fluoroquinolones and sulfonamides in milk was prepared based on the principle of competitive inhibition immunochromatography. The performance indicators of the test strip were verified. The results showed that the test strip can simultaneously detect 4 tetracyclines,13 fluoroquinolones and 13 sulfonamides,and the detection limits all can meet the national residue limits; the tests strip exhibited false positive rate≤5% and false negative rate = 0; and no cross-reaction with other drugs was commonly found in milk,indicating good specificity. The method is simple,rapid,and has low cost and easy popularization. It provides a means for realizing on-site rapid detection and is of important practical significance to guarantee of safety of milk and dairy products in China.展开更多
Nine new sulfonamides derived from carvacrol were prepared through a reaction between 4-hydroxy-2-isopropyl-5-methyl benzene sulfonyl chloride with various amines in excellent yields (76% - 92%). The sulfonamides were...Nine new sulfonamides derived from carvacrol were prepared through a reaction between 4-hydroxy-2-isopropyl-5-methyl benzene sulfonyl chloride with various amines in excellent yields (76% - 92%). The sulfonamides were characterized using spectrometric and spectroscopic methods. Among these compounds, three derivatives showed excellent results in antibacterial activity against resistant S. aureus strains, with MIC values ranging from 3.9 to 62.50 ppm. The sulfonamide derivative of 4-methylaniline (SULF-1) had the best performance for all tested strains of bacteria (MIC = 3.9 to 15.62 ppm). Furthermore, the sulfonamide derivative of 4-fluoro aniline (SULF-3), which also presented promising results, was found to have a synergistic effect when combined with tetracycline and partial synergistic effect when combined with ampicillin, exhibiting an FIC index between 0.50 and 0.75. The sulfonamide derivative of 4-methylaniline had a synergistic effect in combination with erythromycin exhibiting an FIC index of 0.37. Carvacrol in association with the antibiotics tested did not have a synergistic effect.展开更多
Polystyrene N-hydroxyl sulfonamide resin 1 was prepared and used to catalyze the esterification of n-butanol and acetic anhydride. The mechanism of catalytic esterification proved by IR spectra of the resins was found...Polystyrene N-hydroxyl sulfonamide resin 1 was prepared and used to catalyze the esterification of n-butanol and acetic anhydride. The mechanism of catalytic esterification proved by IR spectra of the resins was found that O-H and N-H of the N-hydroxyl sulfonamide resin reacted with the acetic anhydride respectively to form the active intermediate polystyrene N,O-diacetyl sulfonamate which was cleaved by n-butanol to produce butyl acetate. The catalytic esterification by resin 1 was in good agreement with the kinetic model of 揵i-bi-ping-pong?mechanism.展开更多
基金the National Key Research and Development Program of China(2022YFD1700204)the Open Fund of State Key Laboratory of Green Pesticide by South China Agricultural University(gplscau202415)the National Natural Science Foundation of China(22477040).
文摘Currently,triazole sulfonamide fungicide could be used to effectively control cucumber downy mildew(CDM),caused by Pseudoperonospora cubensis.In this study,a series of triazole sulfonamide derivatives containing diphenyl ether(DE)fragment were designed and synthesized.All target compounds were evaluated for their fungicidal activity against four oomycete diseases.Compound 10b showed the best activity against CDM with 40%control efficacy at 0.78 mg/L,which was the same as amisulbrom.Meanwhile,compounds 10d and 10h showed good inhibitory activity against Peronophythora litchii and compounds 10e,10f,10l and 10q showed good inhibitory activity against Phytophthora infestans.The results of computational chemistry showed that compound 10b had the same binding mode as amisulbrom and formed hydrogen bonds with the residues Gln9,His189 and Ash217.Compound 10b could be further investigated as a potential fungicide candidate.This study also provides a useful optimization strategy for the design of novel fungicides against CDM.
基金supported by the National Natural Science Foundation of China(Nos.21976045 and 22076112)the CAS Key Laboratory of Coastal Environmental Processes and Ecological Remediation(No.2020KFJJ03).
文摘Obtaining the sulfonamides(SAs)concentrations in the water body and sediment bulk was a prerequisite to reveal their transport and partitioning behavior in sediment-water environments and accurately assess their ecological risk.In the present study,the influences of multifactor interactions on the performance of o-DGTs with XAD-18 binding gels were analyzed by central combination experiments and response surfaces analysis,in which the target compounds were 9 SAs.The results indicated that dissolved organic matter(DOM),pH,and suspended particulate matter(SS)had significant effects on the o-DGT sampling,whereas this o-DGT was independent of the ionic strength(IS).Concentning the composite influence of the four factors,the interaction between DOM and SS posed the most significant effect on all 9 SAs compounds.Subsequently,an o-DGT and DIFSmodel was applied to explore the SAs migration between the water-sediments interface.The difference between desorption rate(k_(b))and adsorption rates(k_(f))values suggested that the kinetics of SAs was dominated by adsorption.Moreover,the short-term sediment-water partitioning of SAs was clarified on the basis of distribution coefficient(K_(dl))for the labile SAs,among which the sulfadiazine(SDZ)had the largest labile pool.The ability of sediments to release SAs to the liquid phase as a sink was determined by response time(T_(c)).Among the 9 SAs,the longterm release of soseulfamethoxypyridazine(SMP)from the solid phase of sediments would have a potential risk to the aquatic environment,to which more attention should be paid in the future.
基金Natural Science Foundation of China for the financial support(Grant No.30772626)
文摘On the basis of the Michael-addition mechanism of classical proteasome inhibitors, six dipeptide vinyl sulfonamide and dipeptide vinyl sulfonate derivatives were designed and synthesized. Moreover, an efficient method for the synthesis of g-amino vinyl sulfonamides, key intermediates to the target molecules, was developed via the Wittig-Horner reaction of peptide aldehyde with Wittig reagents derived from methanesulfonamides.
基金funding support from the National Natural Science Foundation of China(No.82074251)the Hunan Natural Science Foundation of China(No.2018JJ2413)the Hunan Provincial Health and Health Commission Project(No.c2018032)。
文摘Objective Sulfanilamide,sulfadiazine,and dapsone were the first sulfonamides to be used to treat malaria by disrupting the folate biosynthesis process,which is essential for parasite survival.Therefore,we aimed to synthesize novel N-(2-arylaminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide derivatives through a rational drug design approach.Methods All compounds were synthesized by the conventional method,and the products were characterized by spectral analysis(1 H NMR and mass spectrometry).The progression of the reaction was monitored using thin-layer chromatography(TLC).All the derivatives were analyzed for their effective binding mode in the allosteric site of the plasmodium cysteine protease falcipain-2.Antibacterial and antifungal activities were determined using the broth dilution method.Results S6(N-(2-thiazol-4 yl)-acetyl-aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide and S9(N-(1 H-benzo[d]imidazol-2-yl)aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide formed five hydrogen bonds;S8(N-(2-1 H-imidazol-2 yl)aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide and S10(N-(1 H-benzo[d]imidazol-5-yl)aminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide formed four hydrogen bonds with the allosteric site of the enzyme.Considering the docking scores and formation of hydrogen bonds with the target enzyme,the novel derivatives were processed for wet lab synthesis.All the newly synthesized derivatives were subjected to in vitro antimalarial,antifungal,and antibacterial activities.All the derivatives exhibited sufficient sensitivity to the Plasmodium falciparum strain compared to the standards.Moreover,compounds S9 and S10 showed the most potent dual antimicrobial and antimalarial activities.They also exhibited powerful molecular interactions in molecular docking studies.Conclusion Based on the above results,it was concluded that N-(2-arylaminophenyl)-2,3-diphenylquinoxaline-6-sulfonamide derivatives have excellent biological potential to act as antimalarial,antifungal,and antibacterial agents.
基金The National Natural Science Foundation of China(Grant No.21202003)the National Basic Research Program of China(Grant No.2012CB518000)the Specialized Research Fund for the Doctoral Program of Higher Education of China(Grant No.20120001110010)
文摘A new series of sulfonamide flavone derivatives are designed as non-covalent inhibitors of proteasome assisted with computer-aided drug design （CADD）. The desired compounds were synthesized successfully and the biological evaluation was subsequently accomplished. The results showed negligible improvement from our lead compound （IC50 for β5 subunit was 14.0 μM）. Thus, these flavone derivatives might be improved as potential 20S proteasome inhibitors.
基金supported by the Natural Science Foundation of Shaanxi Province (No. 2009jm4002-1)
文摘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.
基金Supported by a grant from UNDP/World Bank/WHO Special Programme for Research and Training in Tropical Diseases(No.900142,930143,960103,970074,990490)the National Science and Technology Development Agency of Thailand(Career Development Award ID no.01-38-007)the Thailand Research Fund(BasicResearch Grants ID No.BRG/13/2543.BRG4580020.BRG 4880006)
文摘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.
基金funded by the Ministry of Agriculture of China (2013-Z10)Chinese Academy of Agricultural Sciences (2012ZL071)Institute of Animal Science, Chinese Academy of Agricultural Sciences (2013ywf-yb-4)
文摘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）.
基金supported by the National Natural Science Foundation of China(No.51221892)the Ministry of Science and Technology of China(No.2012AA062606,2012BAJ25B04)the People Programme(Marie CurieActions) of the European Union’s Seventh Programme FP7/2007-2013 under a REA grant(No.318926)
文摘The occurrence of antibiotics in the environment has recently raised serious concerns regarding their potential threat to human health and aquatic ecosystem. A new magnetic nanocomposite, Fe304@C （Fe304 coated with carbon）, was synthesized, characterized, and then applied to remove five commonly-used sulfonamides （SAs） from water. Due to its combinational merits of the outer functionalized carbon shell and the inner magnetite core, Fe3O4@C exhibited a high adsorption affinity for selected SAs and a fast magnetic separability. The adsorption kinetics of SAs on Fe304 @ C could be expressed by the pseudo second-order model. The adsorption isotherms were fitted well with the Dual-mode model, revealing that the adsorption process consisted of an initial partitioning stage and a subsequent hole-filling stage. Solution pH exerted a strong impact on the adsorption process with the maximum removal efficiencies （74% to 96%） obtained at pH 4.8 for all selected SAs. Electrostatic force and hydrogen bonding were two major driving forces for adsorption, and electron-donor-acceptor interactions may also make a certain contribution. Because the synthesized Fe304@C showed comprehensive advantages of high adsorptivity, fast magnetic separability, and prominent reusability, it has potential applications in water treatment.
基金This work was supported by“National Key Research and Development Program of China”(Project No.2018YFC1603400)Science and Technology Program of Hebei Province(Project No.19225503D).
文摘The aim of this work was to develop an automated on-line solid phase extraction(SPE)with liquid chromatography-tandem mass spectrometry method for the detection of fifteen sulfonamides in pork and fish samples.Samples were extracted with 0.2%formic acid acetonitrile solution,purified by on-line SPE device with HLB column,then separated by XBridge C18 column,using 0.1%formic acid solution and acetonitrile as the mobile phase.Mass spectrometric data was acquired under multiple reaction monitoring(MRM)mode using positive ionization electrospray.Internal standard method was used in the quantification,good linear relationship was got in range of 0.1–100 ng/mL and correlation coefficient was higher than 0.9990.The limits of detection were in the range of 0.125–2.00g/kg and the limits of quantitation were in the range of 0.250–5.00g/kg.Recoveries of the method were in range of 78.3%–99.3%,relative standard deviation were lower than 10%.The method was simple,sensitivity,and could be used for routine supervision and analysis of fifteen sulfonamides in pork and fish.
基金financially supported by the National Natural Science Foundation of China(Nos.22074161 and 21976213)Guangdong Basic and Applied Basic Research Foundation(No.2019A1515010107)+3 种基金the Science and Technology Planning Project of Guangzhou City(No.202102080167)the Research and Development Plan for Key Areas of Food Safety in Guangdong Province of China(No.2019B020211001)the National Key Research and Development Program of China(No.2019YFC1606101)the State Key Program of National Natural Science of China(No.22134007)。
文摘Surface-enhanced Raman scattering(SERS)spectroscopy has been employed as a rapid analysis technology for food security inspection recently.Nowadays,it is still a great challenge to rapidly quantify multiple trace antibiotics potentially abused in aquaculture industry.In this work,a magnetic Ti_(3)C_(2)T_(x)/Fe_(3)O_(4)/Ag substrate was prepared for the development of a reliable rapid SERS quantification method for multiple trace sulfonamides in aquatic products.This magnetic substrate had good uniformity,reproducibility,stability and SERS activity.Moreover,this substrate could integrate the magnetic separation-enrichment and matrix clean-up without cross contamination,which endowed it with good selectivity and antiinterference capability during real sample analysis.The electromagnetic enhancement and chemical enhancement mechanism of this magnetic substrate were studied in detail to reveal its good separationenrichment performance and SERS activity.Finally,a rapid SERS quantification method was established and practically applied for trace phthalic sulfathiazole(PST)and silver sulfadiazine(SSD)in aquatic products by using Ti_(3)C_(2)T_(x)/Fe_(3)O_(4)/Ag magnetic substrates.Trace PST and SSD could be actually detected and quantified as 55.9μg/kg and 64.0μg/kg in aquatic products,respectively.Good recoveries of 83.9%-116%with relative standard deviations(RSDs)of 0.5%-3.2%for PST and 80.2%-102%with RSDs of 1.3%-5.8%for SSD were obtained.This work proposed an efficient and reliable method for rapid quantification of trace multiple sulfonamides in complex aquatic samples during food security inspection.
文摘[ Objective] This study was conducted to establish a new UPLC-MS method for simultaneous detection of sulfonanfides and chloramphenicols in honey. [ Method] In this experiment, 0.2% formic acid-acetonitrile was used as an extractant to simultaneously extract chloramphenicoJs and sulfonamides from drugs. The extract was then loaded and extracted with an efficient separation column Oasis PRIME HLB. After nitrogen blow-concentration and dissolution with mobile phase, the extract was loaded on UPLC and detected by MS. [ Resultl There was a good linear relation in the range of 0. 1 - 10 ng/ml for chloramphenicols, with a correlation coefficient of 0.991, while sulfonamides had a good linear relation in the range of 0.5 - 50 ng/ml. The lowest detection limit of chloramphenicols and sulfonamides were 0. 1 and 0.5 μg/kg, respectively. The recoveries were in the range of 82.50% - 101.2%, with RSD values in the range of 3.2% -4.0%. [ Conclusion] This method is simple and fast with low detection limit, high recovery and good reproducibility, and could be used for simultaneous detection of re- sidual chloramphenicols and sulfonamides in honey. Key words UHPLC-MS; Sulfonamides ; Chloramphenicols ; Honey
基金supported by the Chinese Major Science and Technology Program for Water Pollution Control and Treat-ment(No.2017ZX07207002-03)the Science and Technology Commission of Shanghai Municipality(Nos.19050501900 and 19DZ1204504)the Scientific Research Fund for Young Teachers of Shanghai Ocean University。
文摘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.
基金the National Natural Science Foundation of China(No.20902070)Natural Science Foundation of Zhejiang Province(No.Y4100579)Qianjiang Talents Program(No.QJD0902004) of Zhejiang Province for financial supports
文摘By using the famous Wilkinson＇s catalyst, N-alkylation of sulfonamides can be easily realized under mild aerobic conditions by using alcohols as the alkylating reagent, giving monoalkylated sulfonamides in high yields and selectivities with water produced as the only byproduct. This advantageous aerobic method is potentially general in substrate scope that it can also be applied to other amides, amines and alcohols.
文摘Acetazolamide(molecular mass(MM),222)belongs to the class of sulfonamides(R-SO2-NH2)and is one of the strongest pharmacological inhibitors of carbonic anhydrase activity.Acetazolamide is excreted unchanged in the urine.Here,we report on the development,validation and biomedical application of a stable-isotope dilution GC-MS method for the reliable quantitative determination of acetazolamide in human urine.The method is based on evaporation to dryness of 50 mL urine aliquots,base-catalyzed derivatization of acetazolamide(d0-AZM)and its internal standard[acetylo-2H3]acetazolamide(d3-AZM)in 30 vol%pentafluorobenzyl(PFB)bromide in acetonitrile(60 min,30C),reconstitution in toluene(200 mL)and injection of 1-mL aliquots.The negative-ion chemical ionization(NICI)mass spectra(methane)of the PFB derivatives contained several intense ions including[M]‒at m/z 581 for d0-AZM and m/z 584 for d3-AZM,suggesting derivatization of their sulfonamide groups to form N,N-dipentafluorobenzyl derivatives(R-SO2-N(PFB)2),i.e.,d0-AZM-(PFB)2 and d3-AZM-(PFB)2,respectively.Quantification was performed by selected-ion monitoring of m/z 581 and 83 for d0-AZM-(PFB)2 and m/z 584 and 86 for d3-AZM-(PFB)2.The limits of detection and quantitation of the method were determined to be 300 fmol(67 pg)and 1 mM of acetazolamide,respectively.Intra-and inter-assay precision and accuracy for acetazolamide in human urine samples in pharmacologically relevant concentration ranges were determined to be 0.3%e4.2%and 95.3%e109%,respectively.The method was applied to measure urinary acetazolamide excretion after ingestion of a 250 mg acetazolamide-containing tablet(Acemit®)by a healthy volunteer.Among other tested sulfonamide drugs,methazolamide(MM,236)was also found to form a N,N-dipentafluorobenzyl derivative,whereas dorzolamide(MM,324)was hardly detectable.No GC-MS peaks were obtained from the PFB bromide derivatization of hydrochlorothiazide(MM,298),xipamide(MM,355),indapamide and metholazone(MM,366 each)or brinzolamide(MM,384).We demonstrate for the first time that sulfonamide drugs can be derivatized with PFB bromide and quantitated by GC-MS.Sulfonamides with MM larger than 236 are likely to be derivatized by PFB bromide but to lack thermal stability.
基金Funded by the National High-Tech Foundation(No. 2003 AA305920)
文摘2-Cetyl-3-20 keto acid（N-ethyl perfluorinated octyl sulfonamide） N-ethyl ester was synthesized by the reaction of N-ethyl-N-hydroxyethyl perfluorinated octyl sulfonamide and alky ketene dimer. The experimental results show that the yield of products can be 89% when the molar ratio of perfluorinated octyl sulfonamide to ketene dimer is 1 ： 1.1 and the reaction lasts about four hours at 80 ℃. The structure of the product was characterized by FTIR and ^1HNMR. The product can dissolve in polar solvents such as NMP, DMAC, THF, DMSO, CHCl3, and 10% weight-loss temperature measured by TGA is 202℃.
基金Bu-Ali Sina University Research Council and Center of Excellence in Development of Environmentally Friendly Methods for Chemical Synthesis(CEDEFMCS) for their support of this work
文摘The electrochemical synthesis of some new sulfonamide derivatives was carried out via the electrochemical oxidation of 2,3-dihydrophthalazine-l,4-dione （1） in the presence of arylsulfinic acids （2a and 2b） as nucleophiles. The results show that, the electrogenerated phthalazine-l,4-dione （lox） participates in a Michael type addition reaction with 2a or 2b and via an EC mechanism to produce the corresponding sulfonamide derivatives. This method provides a one-pot procedure for the synthesis of new sulfonamide derivatives of potential biological significance in good yields without using toxic reagents at a carbon electrode in an environmentally friendly manner.
基金Supported by Hebei Science and Technology Program(16275507D)
文摘Aiming at the market demand for rapid detection of tetracyclines,fluoroquinolones and sulfonamides in milk,a golloidal gold immunochromatography test strip for simultaneous detection of tetracyclines,fluoroquinolones and sulfonamides in milk was prepared based on the principle of competitive inhibition immunochromatography. The performance indicators of the test strip were verified. The results showed that the test strip can simultaneously detect 4 tetracyclines,13 fluoroquinolones and 13 sulfonamides,and the detection limits all can meet the national residue limits; the tests strip exhibited false positive rate≤5% and false negative rate = 0; and no cross-reaction with other drugs was commonly found in milk,indicating good specificity. The method is simple,rapid,and has low cost and easy popularization. It provides a means for realizing on-site rapid detection and is of important practical significance to guarantee of safety of milk and dairy products in China.
文摘Nine new sulfonamides derived from carvacrol were prepared through a reaction between 4-hydroxy-2-isopropyl-5-methyl benzene sulfonyl chloride with various amines in excellent yields (76% - 92%). The sulfonamides were characterized using spectrometric and spectroscopic methods. Among these compounds, three derivatives showed excellent results in antibacterial activity against resistant S. aureus strains, with MIC values ranging from 3.9 to 62.50 ppm. The sulfonamide derivative of 4-methylaniline (SULF-1) had the best performance for all tested strains of bacteria (MIC = 3.9 to 15.62 ppm). Furthermore, the sulfonamide derivative of 4-fluoro aniline (SULF-3), which also presented promising results, was found to have a synergistic effect when combined with tetracycline and partial synergistic effect when combined with ampicillin, exhibiting an FIC index between 0.50 and 0.75. The sulfonamide derivative of 4-methylaniline had a synergistic effect in combination with erythromycin exhibiting an FIC index of 0.37. Carvacrol in association with the antibiotics tested did not have a synergistic effect.
基金Natural Science Foundation of China (Project number: 20074017)
文摘Polystyrene N-hydroxyl sulfonamide resin 1 was prepared and used to catalyze the esterification of n-butanol and acetic anhydride. The mechanism of catalytic esterification proved by IR spectra of the resins was found that O-H and N-H of the N-hydroxyl sulfonamide resin reacted with the acetic anhydride respectively to form the active intermediate polystyrene N,O-diacetyl sulfonamate which was cleaved by n-butanol to produce butyl acetate. The catalytic esterification by resin 1 was in good agreement with the kinetic model of 揵i-bi-ping-pong?mechanism.
