Quantitative thin layer chromatographic multi-sulfonamide screening procedure.

PubMed

Thomas, M H; Soroka, K E; Thomas, S H

1983-07-01

In-situ optical scanning of fluorescamine derivatives on thin layer silica gel plates provides a rapid method for the determination of multiple sulfonamides at levels below 0.1 ppm. Sample preparation is minimal. Homogenized liver or muscle is extracted with ethyl acetate and then back-extracted into 0.2M glycine buffer. After pH adjustment, the extract is washed with hexane and extracted with methylene chloride. The organic phase is evaporated to dryness and reconstituted in methanol. Pre-adsorbent layer silica gel plates are used for chromatography. The method has been applied to residues of sulfamethazine, sulfadimethoxine, sulfathiazole, sulfaquinoxaline, and sulfabromomethazine in cattle, swine, turkey, and duck tissues.

Identification and Evaluation of Novel Acetolactate Synthase Inhibitors as Antifungal Agents

PubMed Central

Richie, Daryl L.; Thompson, Katherine V.; Studer, Christian; Prindle, Vivian C.; Aust, Thomas; Riedl, Ralph; Estoppey, David; Tao, Jianshi; Sexton, Jessica A.; Zabawa, Thomas; Drumm, Joseph; Cotesta, Simona; Eichenberger, Jürg; Schuierer, Sven; Hartmann, Nicole; Movva, N. Rao; Tallarico, John A.

2013-01-01

High-throughput phenotypic screening against the yeast Saccharomyces cerevisiae revealed a series of triazolopyrimidine-sulfonamide compounds with broad-spectrum antifungal activity, no significant cytotoxicity, and low protein binding. To elucidate the target of this series, we have applied a chemogenomic profiling approach using the S. cerevisiae deletion collection. All compounds of the series yielded highly similar profiles that suggested acetolactate synthase (Ilv2p, which catalyzes the first common step in branched-chain amino acid biosynthesis) as a possible target. The high correlation with profiles of known Ilv2p inhibitors like chlorimuron-ethyl provided further evidence for a similar mechanism of action. Genome-wide mutagenesis in S. cerevisiae identified 13 resistant clones with 3 different mutations in the catalytic subunit of acetolactate synthase that also conferred cross-resistance to established Ilv2p inhibitors. Mapping of the mutations into the published Ilv2p crystal structure outlined the chlorimuron-ethyl binding cavity, and it was possible to dock the triazolopyrimidine-sulfonamide compound into this pocket in silico. However, fungal growth inhibition could be bypassed through supplementation with exogenous branched-chain amino acids or by the addition of serum to the medium in all of the fungal organisms tested except for Aspergillus fumigatus. Thus, these data support the identification of the triazolopyrimidine-sulfonamide compounds as inhibitors of acetolactate synthase but suggest that targeting may be compromised due to the possibility of nutrient bypass in vivo. PMID:23478965

Circulating levels of perfluoroalkyl substances are associated with dietary patterns - A cross sectional study in elderly Swedish men and women.

PubMed

Sjogren, Per; Montse, Rachel; Lampa, Erik; Salihovic, Samira; van Bavel, Bert; Lind, Lars; Lind, P Monica

2016-10-01

In our daily life, we are exposed to perfluoroalkyl substances (PFAS) with possible health implications. The main exposure route for these substances is diet but comparative studies on how dietary habits influence exposure are lacking. To examine the relations between blood levels of PFAS and adherence to three predefined dietary patterns (a WHO recommended diet, a Mediterranean-like diet, and a Low-Carbohydrate High-Protein (LCHP) diet) in an elderly Swedish population. Dietary data from 7-day food records and serum concentrations of PFAS were obtained from a 70-year-old Swedish population (n=844), the Prospective Investigation of the Vasculature in Uppsala Seniors (PIVUS) study. The Healthy Diet Indicator score (based on WHO recommendations), the Mediterranean Diet Score and LCHP score were used to assess adherence. Multivariate linear regression was used to assess the associations between eight major PFAS and adherence to each dietary pattern. The WHO recommended diet was positively associated with perfluorohexane sulfonic acid (PFHxS). The LCHP diet was positively related to four out of eight PFAS; namely, perfluorooctane sulfonic acid (PFOS), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA) and perfluoroundecanoic acid (PFUnDA). The Mediterranean-like diet was positively associated with most PFAS; namely perfluorooctanoic acid (PFOA), perfluorooctane sulfonamide (PFOSA), PFHxS, PFNA, PFDA, and PFUnDA. All dietary patterns were positively associated with blood levels of PFAS. The highest body burden of PFAS was found in individuals with high adherence to a Mediterranean-like diet, whilst individuals who more closely followed the officially recommended diet displayed a lower body burden of these compounds. Copyright © 2016 Elsevier Inc. All rights reserved.

Perfluoroalkyl and polyfluoroalkyl substances in cord blood of newborns in Shanghai, China: Implications for risk assessment.

PubMed

Wang, Bin; Chen, Qian; Shen, Lixiao; Zhao, Shasha; Pang, Weiyi; Zhang, Jun

2016-12-01

Perfluoroalkyl and polyfluoroalkyl substances (PFASs) are commonly used in industrial applications and consumer products, and their potential health impacts are of concern, especially for vulnerable population like fetuses. However, in utero exposure to PFASs and health implications are far from fully characterized in China. To fill in the gap, we analyzed 10 PFASs in cord plasma samples (N=687) collected in Shanghai between 2011 and 2012, one of the regions widely polluted with PFASs in China. A questionnaire survey on maternal and diet-related factors was conducted. Except for perfluoroheptanoic acid (PFHpA) and perfluorooctane sulfonamide (PFOSA), all other PFASs were detected in ˃90% of the samples. Perfluorooctanoic acid (PFOA) was the most predominant PFAS (median value: 6.96ng/mL), followed by perfluorooctane sulfonate (PFOS) (2.48ng/mL). PFOA and PFOS combined contributed to 80% of the total PFASs. The final multiple regression models showed that maternal factors including maternal age, body mass index, gestational age, economic status and educational level as well as consumption of fish and wheat were significantly related with concentrations of PFASs in cord blood. The risk assessment using the hazard quotients (HQs) approach on the basis of plasma PFAS levels indicated no potential concern for developmental toxicity in the local newborns. The results demonstrate the unique profiles of local prenatal exposure to PFASs, suggesting that PFOA has been the primary human exposure due to its widespread use and pollution. Special attention to high PFOA exposure and confirmation of potential determinants should be taken as a priority in the future plan for risk management and actions in this area. Copyright © 2016 Elsevier Ltd. All rights reserved.

Phthalocyanine-sulfonamide conjugates: Synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria.

PubMed

da Silva, Raquel Nunes; Cunha, Ângela; Tomé, Augusto C

2018-06-25

Phthalocyanines bearing four or eight sulfonamide units were synthesized and their efficiency in the photodynamic inactivation of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria was evaluated. Conjugates with simpler sulfonamide units (N,N-diethylbenzenesulfonamide, N-isopropylbenzenesulfonamide and N-(4-methoxyphenyl)benzenesulfonamide) caused stronger inactivation than those with heterocyclic groups (N-(thiazol-2-yl)benzenesulfonamide) or long alkyl chains (N-dodecylbenzenesulfonamide) in both bacteria. Furthermore, the encapsulation of the phthalocyanine-sulfonamide conjugates within polyvinylpyrrolidone micelles, used as drug delivery vehicles, in general showed to enhance the inactivation efficiency. The results show that encapsulated phthalocyanine-sulfonamide conjugates are a promising class of photosensitizers to be used in photodynamic antimicrobial therapy. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

PubMed

Bennett, John M; Shapiro, Jonathan D; Choinski, Krystina N; Mei, Yingbin; Aulita, Sky M; Dominguez, Giovanny M; Majireck, Max M

2018-01-03

Decomposition of N-tosyl-1,2,3-triazoles with rhodium(II) acetate dimer in the presence of alcohols forms synthetically versatile N-(2-alkoxyvinyl)sulfonamides, which react under a variety of conditions to afford useful N- and O-containing compounds. Acid-catalyzed addition of alcohols or thiols to N-(2-alkoxyvinyl)sulfonamide-containing phthalans provides access to ketals and thioketals, respectively. Selective reduction of the vinyl group in N-(2-alkoxyvinyl)sulfonamide-containing phthalans via hydrogenation yields the corresponding phthalan in good yield, whereas reduction with sodium bis(2-methoxyethoxy)aluminumhydride generates a ring-opened phenethylamine analogue. Because the N-(2-alkoxyvinyl)sulfonamide functional group is synthetically versatile, but often hydrolytically unstable, this protocol emphasizes key techniques in preparing, handling, and reacting these pivotal substrates in several useful transformations.

Quantitative Determination of Fluorochemicals in Municipal Landfill Leachates

PubMed Central

Huset, Carin A.; Barlaz, Morton A.; Barofsky, Douglas F.; Field, Jennifer A.

2014-01-01

Twenty four fluorochemicals were quantified in landfill leachates recovered from municipal refuse using an analytical method based on solid-phase extraction, dispersive-carbon sorbent cleanup, and liquid chromatography/tandem mass spectrometry. The method was applied to six landfill leachates from four locations in the U.S. with as well as to a leachate generated by a laboratory bioreactor containing residential refuse. All seven leachates had the common characteristic that short-chain (C4-C7) carboxylates or sulfonates were greater in abundance than their respective longer-chain homologs (≥C8). Perfluoroalkyl carboxylates were the most abundant (67 ± 4% on a nanomolar (nM) basis) fluorochemicals measured in leachates; concentrations of individual carboxylates reaching levels up to 2,800 ng L−1. Perfluoroalkyl sulfonates were the next most abundant class (22 ± 2%) on a nM basis; their abundances in each of the seven leachates derived from municipal refuse were greater for the shorter-chain homologs (C4 and C6) compared to longer-chain homologs (C8 and C10). Perfluorobutane sulfonate concentrations were as high as 2,300 ng/L. Sulfonamide derivatives composed 8 ± 2.1% (nM basis) of the fluorochemicals in landfill leachates with methyl (C4 and C8) and ethyl (C8) sulfonamide acetic acids being the most abundant. Fluorotelomer sulfonates (6:2 and 8:2) composed 2.4 ± 1.3% (nM basis) of the fluorochemicals detected and were present in all leachates. PMID:21194725

Determination of perfluorinated alkyl acid concentrations in biological standard reference materials.

PubMed

Reiner, Jessica L; O'Connell, Steven G; Butt, Craig M; Mabury, Scott A; Small, Jeff M; De Silva, Amila O; Muir, Derek C G; Delinsky, Amy D; Strynar, Mark J; Lindstrom, Andrew B; Reagen, William K; Malinsky, Michelle; Schäfer, Sandra; Kwadijk, Christiaan J A F; Schantz, Michele M; Keller, Jennifer M

2012-11-01

Standard reference materials (SRMs) are homogeneous, well-characterized materials used to validate measurements and improve the quality of analytical data. The National Institute of Standards and Technology (NIST) has a wide range of SRMs that have mass fraction values assigned for legacy pollutants. These SRMs can also serve as test materials for method development, method validation, and measurement for contaminants of emerging concern. Because inter-laboratory comparison studies have revealed substantial variability of measurements of perfluoroalkyl acids (PFAAs), future analytical measurements will benefit from determination of consensus values for PFAAs in SRMs to provide a means to demonstrate method-specific performance. To that end, NIST, in collaboration with other groups, has been measuring concentrations of PFAAs in a variety of SRMs. Here we report levels of PFAAs and perfluorooctane sulfonamide (PFOSA) determined in four biological SRMs: fish tissue (SRM 1946 Lake Superior Fish Tissue, SRM 1947 Lake Michigan Fish Tissue), bovine liver (SRM 1577c), and mussel tissue (SRM 2974a). We also report concentrations for three in-house quality-control materials: beluga whale liver, pygmy sperm whale liver, and white-sided dolphin liver. Measurements in SRMs show an array of PFAAs, with perfluorooctane sulfonate (PFOS) being the most frequently detected. Reference and information values are reported for PFAAs measured in these biological SRMs.

Use of newborn screening program blood spots for exposure assessment: declining levels of perluorinated compounds in New York State infants.

PubMed

Spliethoff, Henry M; Tao, Lin; Shaver, Shannon M; Aldous, Kenneth M; Pass, Kenneth A; Kannan, Kurunthachalam; Eadon, George A

2008-07-15

Temporal biomonitoring studies can assess changes in population exposures to contaminants, but collection of biological specimens with adequate representation and sufficient temporal resolution can be resource-intensive. Newborn Screening Programs (NSPs) collect blood as dried spots on filter paper from nearly all infants born in the United States (U.S.). In this study, we investigated the use of NSP blood spots for temporal biomonitoring by analyzing perfluorooctane sulfonate (PFOS), perfluorooctane sulfonamide (PFOSA), perfluorohexane sulfonate (PFHxS), perfluorooctanoic acid (PFOA), and perfluorononanoic acid (PFNA) in 110 New York State (NYS) NSP blood spot composite specimens collected between 1997 and 2007, representing a total of 2640 infants. All analytes were detected in > or =90% of the specimens. Concentrations of PFOS, PFOSA, PFHxS, and PFOA exhibited significant exponential declines after the year 2000, coinciding with the phase-out in PFOS production in the U.S. Calculated disappearance half-lives for PFOS, PFHxS, and PFOA (4.4, 8.2, and 4.1 years, respectively) were similar to biological half-lives reported for retired fluorochemical workers. Our results suggest sharp decreases in perinatal exposure of NYS infants to PFOS, PFOSA, PFHxS, and PFOA and demonstrate, for the first time, the utility of NSP blood spots for assessment of temporal trends in exposure.

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

PubMed

Kim, Taehoon; McCarver, Stefan J; Lee, Chulbom; MacMillan, David W C

2018-03-19

Herein we report a highly efficient method for nickel-catalyzed C-N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C-N bond reductive elimination occurs from a triplet excited Ni II complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Characterization of occurrence, sources and sinks of perfluoroalkyl and polyfluoroalkyl substances (PFASs) in a tropical urban catchment.

PubMed

Chen, Huiting; Reinhard, Martin; Nguyen, Tung Viet; You, Luhua; He, Yiliang; Gin, Karina Yew-Hoong

2017-08-01

Understanding the sources, occurrence and sinks of perfluoroalkyl and polyfluoroalkyl substances (PFASs) in the urban water cycle is important to protect and utilize local water resources. Concentrations of 22 target PFASs and general water quality parameters were determined monthly for a year in filtered water samples from five tributaries and three sampling stations of an urban water body. Of the 22 target PFASs, 17 PFASs were detected with a frequency >93% including PFCAs: C4-C12 perfluoroalkyl carboxylates, C4, C6, C8, and C10 perfluoroalkane sulfonates, perfluorooctane sulfonamides and perfluorooctane sulfonamide substances (FOSAMs), C10 perfluoroalkyl phosphonic acid (C10 PFPA), 6:2 fluorotelomer sulfonic acid (6:2 FTSA) and C8/C8 perfluoroalkyl phosphinic acid (C8/C8-PFPIA). The most abundant PFASs in water were PFBS (1.4-55 ng/L), PFBA (1.0-23 ng/L), PFOS (1.5-24 ng/L) and PFOA (2.0-21 ng/L). In the tributaries, PFNA concentrations ranged from 1.2 to 87.1 ng/L except in the May 2013 samples of two tributaries, which reached 520 and 260 ng/L. Total PFAS concentrations in the sediment samples ranged from 1.6 to 15 ng/g d.w. with EtFOSAA, PFDoA, PFOS and PFDA being the dominant species. Based on water and sediment data, two types of sources were inferred: one-time or intermittent point sources and continuous non-point sources. FOSAMs and PFOS released continually from non-point sources, C8/C8 PFPIA, PFDoA and PFUnA was released from point sources. The highly water soluble short-chain PFASs including PFBA, PFPeA and PFBS remained predominantly in the water column. The factors governing solution phase concentrations appear to be compound hydrophobicity and sorption to suspended particles. Correlation of the dissolved phase concentrations with precipitation data suggested stormwater was a significant source of PFBA, PFBS, PFUnA and PFDoA. Negative correlations with precipitation indicated sources feeding FOSAA and FOSA directly into the tributaries. Copyright © 2017 Elsevier Ltd. All rights reserved.

Kinetic analysis of aerobic biotransformation pathways of a perfluorooctane sulfonate (PFOS) precursor in distinctly different soils.

PubMed

Zhang, Lilan; Lee, Linda S; Niu, Junfeng; Liu, Jinxia

2017-10-01

With the phaseout of perfluorooctane sulfonate (PFOS) production in most countries and its well known recalcitrance, there is a need to quantify the potential release of PFOS from precursors previously or currently being emitted into the environment. Aerobic biodegradation of N-ethyl perfluorooctane sulfonamidoethanol (EtFOSE) was monitored in two soils from Indiana, USA: an acidic forest silt loam (FRST-48, pH = 5.5) and a high pH agricultural loam (PSF-49, pH = 7.8) with similar organic carbon contents (2.4 and 2.6%) for 210 d and 180 d, respectively. At designated times, triplicate samples were sacrificed for which headspace samples were taken followed by three sequential extractions. Extracts were analyzed using HPLC-tandem mass spectrometry. Measured profiles of EtFOSE degradation and generation/degradation of subsequent metabolites were fitted to the Indiana soils data as well as to a previously published data set for a Canadian soil using an R-based model (KinGUII) to explore pathways and estimate half-lives (t 1/2 ) for EtFOSE and metabolites. EtFOSE degradation ranged from a few days to up to a month. PFOS yields ranged form 1.06-5.49 mol% with the alkaline soils being four to five times higher than the acidic soil. In addition, a direct pathway to PFOS had to be invoked to describe the early generation of PFOS in the Canadian soil. Of all metabolites, the sulfonamidoacetic acids were the most persistent (t 1/2  ≥ 3 months) in all soils. We hypothesized that while pH-pK a dependent speciation may have impacted rates, differences in microbial communities between the 3 soils arising from varied soil properties including pH, nutrient levels, soil management, and climatic regions are likely the major factors affecting pathways, rates, and PFOS yields. Copyright © 2017 Elsevier Ltd. All rights reserved.

N-(1-Allyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide hemihydrate.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Geffken, Detlef; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

In the title compound, C17H17N3O3 (.)0.5H2O, the indazole system makes a dihedral angle of 46.19 (8)° with the plane through the benzene ring and is nearly perpendicular to the allyl group, as indicated by the dihedral angle of 81.2 (3)°. In the crystal, the water mol-ecule, disordered over two sites related by an inversion center, forms O-H⋯N bridges between indazole N atoms of two sulfonamide mol-ecules. It is also connected via N-H⋯O inter-action to the third sulfonamide mol-ecule; however, due to the water mol-ecule disorder, only every second mol-ecule of sulfonamide participates in this inter-action. This missing inter-action results in a slight disorder of the sulfonamide S,O and N atoms which are split over two sites with half occupancy. With the help of C-H⋯O hydrogen bonds, the mol-ecules are further connected into a three-dimensional network.

Tissue-specific concentrations and patterns of perfluoroalkyl carboxylates and sulfonates in East Greenland polar bears.

PubMed

Greaves, Alana K; Letcher, Robert J; Sonne, Christian; Dietz, Rune; Born, Erik W

2012-11-06

Several perfluoroalkyl carboxylates (PFCAs) and perfluoroalkyl sulfonates (PFSAs) of varying chain length are bioaccumulative in biota. However, wildlife reports have focused on liver and with very little examination of other tissues, and thus there is a limited understanding of their distribution and potential effects in the mammalian body. In the present study, the comparative accumulation of C(6) to C(15) PFCAs, C(4), C(6), C(8) and C(10) PFSAs, and select precursors were examined in the liver, blood, muscle, adipose, and brain of 20 polar bears (Ursus maritimus) from Scoresby Sound, Central East Greenland. Overall, PFSA and PFCA concentrations were highest in liver followed by blood > brain > muscle ≈ adipose. Liver and blood samples contained proportionally more of the shorter/medium chain length (C(6) to C(11)) PFCAs, whereas adipose and brain samples were dominated by longer chain (C(13) to C(15)) PFCAs. PFCAs with lower lipophilicities accumulated more in the liver, whereas the brain accumulated PFCAs with higher lipophilicities. The concentration ratios (±SE) between perfluorooctane sulfonate and its precursor perfluorooctane sulfonamide varied among tissues from 9 (±1):1 (muscle) to 36 (±7):1 (liver). PFCA and PFSA patterns in polar bears indicate that the pharmacokinetics of these compounds are to some extent tissue-specific, and are the result of several factors that may include differing protein interactions throughout the body.

Characterization of two passive air samplers for per- and polyfluoroalkyl substances.

PubMed

Ahrens, Lutz; Harner, Tom; Shoeib, Mahiba; Koblizkova, Martina; Reiner, Eric J

2013-12-17

Two passive air sampler (PAS) media were characterized under field conditions for the measurement of per- and polyfluoroalkyl substances (PFASs) in the atmosphere. The PASs, consisting of polyurethane foam (PUF) and sorbent-impregnated PUF (SIP) disks, were deployed for over one year in parallel with high volume active air samplers (HV-AAS) and low volume active air samplers (LV-AAS). Samples were analyzed for perfluoroalkyl carboxylic acids (PFCAs), perfluoroalkane sulfonic acids (PFSAs), fluorotelomer alcohols (FTOHs), fluorotelomer methacrylates (FTMACs), fluorotelomer acrylates (FTACs), perfluorooctane sulfonamides (FOSAs), and perfluorooctane sulfonamidoethanols (FOSEs). Sampling rates and the passive sampler medium (PSM)-air partition coefficient (KPSM-A) were calculated for individual PFASs. Sampling rates were similar for PFASs present in the gas phase and particle phase, and the linear sampling rate of 4 m(-3) d(-1) is recommended for calculating effective air sample volumes in the SIP-PAS and PUF-PAS for PFASs except for the FOSAs and FOSEs in the PUF-PAS. SIP disks showed very good performance for all tested PFASs while PUF disks were suitable only for the PFSAs and their precursors. Experiments evaluating the suitability of different isotopically labeled fluorinated depuration compounds (DCs) revealed that (13)C8-perfluorooctanoic acid (PFOA) was suitable for the calculation of site-specific sampling rates. Ambient temperature was the dominant factor influencing the seasonal trend of PFASs.

EFFECTS OF PRENATAL PERFLUOROOCTANE SULFONATE (PFOS) EXPOSURE ON LUNG MATURATION IN THE PERINATAL RAT

EPA Science Inventory

Background: Perfluorooctane sulfonate (PFOS), found widely in wildlife and humans, is environmentally and metabolically stable. Environmental PFOS may be from its use as a surfactant, hydrolysis of perfluorooctanesulfonyl fluoride, and degradation of N-alkyl-perfluorooctanesulfon...

Crystal structures of 4-meth-oxy-N-(4-methyl-phenyl)benzene-sulfonamide and N-(4-fluoro-phenyl)-4-meth-oxy-benzene-sulfonamide.

PubMed

Rodrigues, Vinola Z; Preema, C P; Naveen, S; Lokanath, N K; Suchetan, P A

2015-11-01

Crystal structures of two N-(ar-yl)aryl-sulfonamides, namely, 4-meth-oxy-N-(4-methyl-phen-yl)benzene-sulfonamide, C14H15NO3S, (I), and N-(4-fluoro-phen-yl)-4-meth-oxy-benzene-sulfonamide, C13H12FNO3S, (II), were determined and analyzed. In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°. In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°. In the crystal structure of (I), N-H⋯O hydrogen bonds form infinite C(4) chains extended in [010], and inter-molecular C-H⋯πar-yl inter-actions link these chains into layers parallel to the ab plane. The crystal structure of (II) features N-H⋯O hydrogen bonds forming infinite one dimensional C(4) chains along [001]. Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

A critical assessment of passive air samplers for per- and polyfluoroalkyl substances

NASA Astrophysics Data System (ADS)

Karásková, Pavlína; Codling, Garry; Melymuk, Lisa; Klánová, Jana

2018-07-01

Since their inclusion in the Stockholm Convention, there has been a need for global monitoring of perfluorooctane sulfonate (PFOS), its salts and perfluorooctanesulfonyl fluoride (PFOSF), along with other non-listed highly fluorinated compounds. Passive air samplers (PAS) are ideal for geographic coverage of atmospheric monitoring. The most common type of PAS, using polyurethane foam (PUF) as a sorbent, was primarily developed for non-polar semivolatile organic compounds (SVOCs) and are not well-validated for polar substances such as the per- and polyfluoroalkyl substances (PFASs), however, they have been used for some PFASs, particularly PFOS. To evaluate their applicability, PAS were deployed for measurement of PFASs in outdoor and indoor air. Outdoors, two types of PAS, one consisting of PUF and one of XAD-2 resin, were deployed in an 18-week calibration study in parallel with a low-volume active air sampler (LV-AAS) in a suburban area. Indoors, PUF-PAS were similarly deployed over 12 weeks to evaluate their applicability for indoor monitoring. Samples were analysed for perfluoroalkyl carboxylic acids (PFCAs), perfluoroalkyl sulfonates (PFSAs), perfluorooctane sulfonamides (FOSAs), and perfluorooctane sulfonamidoethanols (FOSEs). In outdoor air, 17 out of the 21 PFAS were detected in more than 50% of samples, with a median ∑17PFASs of 18.0 pg m-3 while 20 compounds were detected in indoor air with a median concentration ∑20PFASs of 76.6 pg m-3 using AAS samplers. PFOS was the most common PFAS in the outdoor air while PFBA was most common indoors. Variability between PAS and AAS was observed and comparing gas phase and particle phase separately or in combination did not account for the variation observed. PUF-PAS may still have a valuable use in PFAS monitoring but more work is needed to identify the applicability of passive samplers for ionic PFAS.

Development and validation of an HPLC method for the determination of ten sulfonamide residues in milk according to 2002/657/EC.

PubMed

Tolika, Evanthia P; Samanidou, Victoria F; Papadoyannis, Ioannis N

2011-07-01

A HPLC method with diode-array detection, at 265 nm, was developed and validated for the determination of ten sulfonamides (SAs): sulfadiazine (SDZ), sulfathiazine (STZ), sulfamethoxine (SMTH), sulfamethizole (SMZ), sulfamethoxypyridazine (SMPZ), sulfamonomethoxine (SMMX), sulfamethoxazole (SMXZ), sulfisoxazole (SIX), sulfadimethoxine (SDMX), and sulfaquinoxaline (SQX) in milk. A mixture of ethyl acetate, n-hexane, and isopropanol was used for the extraction of target analytes from milk. The mobile phase, a mixture of 0.1% v/v formic acid, CH(3) CN, and CH(3) OH was delivered to the analytical column under a gradient program. The procedure was validated according to the European Union regulation 2002/657/EC in terms of selectivity, stability, decision limit, detection capability, accuracy, and precision. Mean recoveries of sulfonamides from milk samples spiked at three concentration levels (0.5×MRL, 1×MRL, and 1.5×MRL) (MRL, maximum residue level) were 93.9-115.9% for SDZ, 97.8-102.9% for STZ, 94.6-107.0% for SMTH, 98.3-111.5% for SMZ, 95.3-108.4% for SMPZ, 97.9-106.0% for SMMX, 97.6-111.3% for SMXZ, 94.3-104.6% for SIX, 96.4-109.1% for SDMX, and 98.2-111.2% for SQX. All RSD values were lower than 8.8%. The decision limits CCa calculated by spiking 20 blank milk samples at MRL (100 μg/kg) ranged from 101.61 to 106.84 μg/kg, whereas the detection capability CCb ranged from 105.64 to 119.01 μg/kg. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

N-(1-Allyl-1H-indazol-5-yl)-4-meth­oxy­benzene­sulfonamide hemihydrate

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Geffken, Detlef; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

In the title compound, C17H17N3O3 .0.5H2O, the indazole system makes a dihedral angle of 46.19 (8)° with the plane through the benzene ring and is nearly perpendicular to the allyl group, as indicated by the dihedral angle of 81.2 (3)°. In the crystal, the water mol­ecule, disordered over two sites related by an inversion center, forms O—H⋯N bridges between indazole N atoms of two sulfonamide mol­ecules. It is also connected via N—H⋯O inter­action to the third sulfonamide mol­ecule; however, due to the water mol­ecule disorder, only every second mol­ecule of sulfonamide participates in this inter­action. This missing inter­action results in a slight disorder of the sulfonamide S,O and N atoms which are split over two sites with half occupancy. With the help of C–H⋯O hydrogen bonds, the mol­ecules are further connected into a three-dimensional network. PMID:24098264

Fluorinated organic compounds in an eastern Arctic marine food web.

PubMed

Tomy, Gregg T; Budakowski, Wes; Halldorson, Thor; Helm, Paul A; Stern, Gary A; Friesen, Ken; Pepper, Karen; Tittlemier, Sheryl A; Fisk, Aaron T

2004-12-15

An eastern Arctic marine food web was analyzed for perfluorooctanesulfonate (PFOS, C8F17SO3-), perfluorooctanoate (PFOA, C7F15COO-), perfluorooctane sulfonamide (PFOSA, C8F17SO2NH2), and N-ethylperfluorooctane sulfonamide (N-EtPFOSA, C8F17SO2NHCH2CH3) to examine the extent of bioaccumulation. PFOS was detected in all species analyzed, and mean concentrations ranged from 0.28 +/- 0.09 ng/g (arithmetic mean +/- 1 standard error, wet wt, whole body) in clams (Mya truncata) to 20.2 +/- 3.9 ng/g (wet wt, liver) in glaucous gulls (Larus hyperboreus). PFOA was detected in approximately 40% of the samples analyzed at concentrations generally smaller than those found for PFOS; the greatest concentrations were observed in zooplankton (2.6 +/- 0.3 ng/g, wet wt). N-EtPFOSA was detected in all species except redfish with mean concentrations ranging from 0.39 +/- 0.07 ng/g (wet wt) in mixed zooplankton to 92.8 +/- 41.9 ng/g (wet wt) in Arctic cod (Boreogadus saida). This is the first report of N-EtPFOSA in Arctic biota. PFOSA was only detected in livers of beluga (Delphinapterus leucas) (20.9 +/- 7.9 ng/g, wet wt) and narwhal (Monodon monoceros) (6.2 +/- 2.3 ng/g, wet wt), suggesting that N-EtPFOSA and other PFOSA-type precursors are likely present but are being biotransformed to PFOSA. A positive linear relationship was found between PFOS concentrations (wet wt) and trophic level (TL), based on delta15N values, (r2 = 0.51, p < 0.0001) resulting in a trophic magnification factor of 3.1. TL-corrected biomagnification factor estimates for PFOS ranged from 0.4 to 9. Both results indicate that PFOS biomagnifies in the Arctic marine food web when liver concentrations of PFOS are used for seabirds and marine mammals. However, transformation of N-EtPFOSA and PFOSA and potential other perfluorinated compounds to PFOS may contribute to PFOS levels in marine mammals and may inflate estimated biomagnification values. None of the other fluorinated compounds (N-EtPFOSA, PFOSA, and PFOA) were found to have a significant relationship with TL, but BMF(TL) values of these compounds were often >1, suggesting potential for these compounds to biomagnify. The presence of perfluorinated compounds in seabirds and mammals provides evidence that trophic transfer is an important exposure route of these chemicals to Arctic biota.

Alkaline digestion and solid phase extraction method for perfluorinated compounds in mussels and oysters from South China and Japan.

PubMed

So, M K; Taniyasu, S; Lam, P K S; Zheng, G J; Giesy, J P; Yamashita, N

2006-02-01

Perfluorinated compounds (PFCs), such as perfluorooctane sulfonate (PFOS), have been identified in the coastal waters of China and Japan. An alkaline digestion method, coupled with solid-phase extraction (SPE), and high-performance liquid chromatography interfaced with high-resolution electrospray tandem mass spectrometry was developed to determine PFCs in mussel and oyster samples from coastal waters of South China and Japan. These techniques produced adequate recoveries and reporting limits with small quantities of PFCs. Concentrations of individual PFCs in mussels and oysters from South China and Japan ranged from 113.6 to 586.0 pg/g, wet weight (ww) for PFOS, 63.1 to 511.6 pg/g, ww for perfluorohexane sulfonate, 9.3 to 30.1 pg/g, ww for perfluorobutane sulfonate and 37.8 to 2957.0 pg/g, ww for perfluorooctane sulfonamide. The quantification of perfluorinated carboxylates was compromised by interferences from carboxylates in the procedural blanks. Perfluoroundecanoate and perfluorononanoate had relatively great blank interferences, which resulted in relatively poor limits of quantification for these compounds. Some PFCs were only identified in a limited number of samples: perfluorododecanoate in samples from Tokyo Bay, Japan (195.9 pg/g, ww); and perfluorodecanoate in Fuzhou, China (131.7 pg/g, ww) and Tokyo Bay (118.6 pg/g, ww). The greatest concentrations of perfluorooctanoate, perfluoroheptanoate, and perfluorohexanoate were observed in samples from Tokyo Bay and Bei Hai, South China.

Occurrence and source apportionment of sulfonamides and their metabolites in Liaodong Bay and the adjacent Liao River basin, North China.

PubMed

Jia, Ai; Hu, Jianying; Wu, Xiaoqin; Peng, Hui; Wu, Shimin; Dong, Zhaomin

2011-06-01

The presence of antibiotics in the environment is of great concern because of their potential for resistance selection among pathogens. In the present study we investigated the occurrence of 19 sulfonamides, five N-acetylated sulfonamide metabolites, and trimethoprim in the Liao River basin and adjacent Liaodong Bay, China, as well as 10 human/agricultural source samples. Within the 35 river samples, 12 sulfonamides, four acetylated sulfonamides, and trimethoprim were detected, with the dominant being sulfamethoxazole (66.6 ng/L), N-acetylsulfamethoxazole (63.1 ng/L), trimethoprim (29.0 ng/L), sulfadiazine (14.0 ng/L), and sulfamonomethoxine (8.4 ng/L); within the 36 marine samples, 10 chemicals were detected, with the main contributions from sulfamethoxazole (25.2 ng/L) and N-acetylsulfamethoxazole (28.6 ng/L). Sulfamethoxazole (25.9%), N-acetylsulfamethoxazole (46.6%), trimethoprim (22.9%), and sulfapyridine (1.4%) were the main chemicals from human sources, while sulfamonomethoxine, sulfamethazine, sulfaquinoxaline, sulfaguanidine, sulfadiazine, sulfanilamide, and sulfamethoxypyridazine were dominant in the animal husbandry sources, specifically, swine and poultry farms, and sulfamethoxazole (91%) was dominant in the mariculture source. A principal component analysis with multiple linear regression was performed to evaluate the source apportionment of total sulfonamides in Liaodong Bay. It was found that animal husbandry contributed 15.2% of total sulfonamides, while human sources contributed 28.5%, and combined human and mariculture sources contributed 56.3%. In addition, the mariculture contribution was 24.1% of total sulfonamides into the sea based on mass flux estimation. The present study is the first report that the environmental levels of sulfonamide metabolites were comparable to the corresponding parents; therefore, we should pay attention to their environmental occurrence. Source apportionment showed human discharge (60.7%) significantly contributed to these antibiotics in Liaodong Bay, which provides important information for environmental management. Copyright © 2011 SETAC.

Distinguishing tautomerism in the crystal structure of (Z)-N-(5-ethyl-2,3-di-hydro-1,3,4-thiadiazol-2-ylidene) -4-methylbenzenesulfonamide using DFT-D calculations and {sup 13}C solid-state NMR

DOE Office of Scientific and Technical Information (OSTI.GOV)

Li, Xiaozhou; Bond, Andrew D.; Johansson, Kristoffer E.

2014-08-01

The crystal structure of (Z)-N-(5-ethyl-2,3-di-hydro-1,3,4-thiadiazol-2-ylidene) -4-methylbenzenesulfonamide contains an imine tautomer, rather than the previously reported amine tautomer. The tautomers can be distinguished using dispersion-corrected density functional theory calculations and by comparison of calculated and measured {sup 13}C solid-state NMR spectra. The crystal structure of the title compound, C{sub 11}H{sub 13}N{sub 3}O{sub 2}S{sub 2}, has been determined previously on the basis of refinement against laboratory powder X-ray diffraction (PXRD) data, supported by comparison of measured and calculated {sup 13}C solid-state NMR spectra [Hangan et al. (2010 ▶). Acta Cryst. B66, 615–621]. The mol@@ecule is tautomeric, and was reported as an aminemore » tautomer [systematic name: N-(5-ethyl-1,3,4-thia@@diazol-2-yl)-p-toluene@@sulfonamide], rather than the correct imine tautomer. The protonation site on the mol@@ecule’s 1,3,4-thia@@diazole ring is indicated by the inter@@molecular contacts in the crystal structure: N—H⋯O hydrogen bonds are established at the correct site, while the alternative protonation site does not establish any notable inter molecular inter@@actions. The two tautomers provide essentially identical Rietveld fits to laboratory PXRD data, and therefore they cannot be directly distinguished in this way. However, the correct tautomer can be distinguished from the incorrect one by previously reported qu@@anti@@tative criteria based on the extent of structural distortion on optimization of the crystal structure using dispersion-corrected density functional theory (DFT-D) calculations. Calculation of the {sup 13}C SS-NMR spectrum based on the correct imine tautomer also provides considerably better agreement with the measured {sup 13}C SS-NMR spectrum.« less

Crystal structures of N-(3-fluoro-benzo-yl)benzene-sulfonamide and N-(3-fluoro-benzo-yl)-4-methyl-benzene-sulfonamide.

PubMed

Suchetan, P A; Naveen, S; Lokanath, N K; Lakshmikantha, H N; Srivishnu, K S; Supriya, G M

2016-04-01

The crystal structures of two N-(aryl-sulfon-yl)aryl-amides, namely N-(3-fluoro-benzo-yl)benzene-sulfonamide, C13H10FNO3S, (I), and N-(3-fluoro-benzo-yl)-4-methyl-benzene-sulfonamide, C14H12FNO3S, (II), are described and compared with related structures. The dihedral angle between the benzene rings is 82.73 (10)° in (I) compared to 72.60 (12)° in (II). In the crystal of (I), the mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions, resulting in a three-dimensional grid-like architecture, while C-H⋯O inter-actions lead to one-dimensional ribbons in (II). The crystals of both (I) and (II) feature strong but non-structure-directing N-H⋯O hydrogen bonds with R 2 (2)(8) ring motifs. The structure of (I) also features π-π stacking inter-actions.

Effect of body condition on tissue distribution of perfluoroalkyl substances (PFASs) in Arctic fox (Vulpes lagopus).

PubMed

Aas, Camilla Bakken; Fuglei, Eva; Herzke, Dorte; Yoccoz, Nigel G; Routti, Heli

2014-10-07

Arctic animals undergo large seasonal fluctuations in body weight. The effect of body condition on the distribution and composition of 16 perfluoroalkyl substances (PFASs) was investigated in liver, blood, kidney, adipose tissue, and muscle of Arctic foxes (Vulpes lagopus) from Svalbard (n = 18, age 1-3 years). PFAS concentrations were generally highest in liver, followed by blood and kidney, while lowest concentrations were found in adipose tissue and muscle. Concentrations of summed perfluorocarboxylic acids and perfluoroalkyl sulfonates were five and seven times higher, respectively, in adipose tissue of lean compared to fat foxes. In addition, perfluorodecanoate (PFDA) and perfluoroheptanesulfonate (PFHpS) concentrations in liver, kidney, and blood, and, perfluorononanoate (PFNA) in liver and blood, were twice as high in the lean compared to the fat foxes. The ratio between perfluorooctane sulfonamide (FOSA) and its metabolite perfluorooctanesulfonate (PFOS) was lowest in liver, muscle, and kidney, while significantly higher proportions of FOSA were found in adipose tissue and blood. The results of the present study suggest that toxic potential of exposure to PFAS among other pollutants in Arctic mammals may increase during seasonal emaciation. The results also suggest that body condition should be taken into account when assessing temporal trends of PFASs.

Removal efficiency of multiple poly- and perfluoroalkyl substances (PFASs) in drinking water using granular activated carbon (GAC) and anion exchange (AE) column tests.

PubMed

McCleaf, Philip; Englund, Sophie; Östlund, Anna; Lindegren, Klara; Wiberg, Karin; Ahrens, Lutz

2017-09-01

Poly- and perfluoroalkyl substances (PFASs) have been detected in drinking water at relatively high concentrations throughout the world which has led to implementation of regulatory guidelines for specific PFASs in drinking water in several European countries and in the U.S. The Swedish National Food Agency has determined that the drinking water of over one third of the country's municipal consumers is at risk or already affected by PFAS contamination. The present study investigated the effects of perfluorocarbon chain length, functional group and isomer structure (branched or linear) on removal of multiple PFASs using granular activated carbon (GAC, Filtrasorb ® 400) and anion exchange (AE, Purolite ® A600) column experiments. The removal of 14 different PFASs, i.e. the C 3 C 11 , C 14 perfluoroalkyl carboxylic acids (PFCAs) (PFBA, PFPeA, PFHxA, PFHpA, PFOA, PFNA, PFDA, PFUnDA, PFDoDA, PFTeDA), perfluorooctane sulfonamide (FOSA), and the C 4 , C 6 , C 8 perfluoroalkyl sulfonic acids (PFSAs) (PFBS, PFHxS, PFOS), was monitored for a 217 day period. The results indicate the selective nature of PFAS removal as the absorbents are loaded with PFASs and dissolved organic carbon (DOC). A clear relationship between perfluorocarbon chain length and removal efficiency of PFASs using GAC and AE was found while PFASs with sulfonate functional groups displayed greater removal efficiency than those with carboxylate groups. Similarly, time to column breakthrough increased with increasing perfluorocarbon chain length and was greater for the PFSAs than the PFCAs for both GAC and AE. Shorter carbon chained PFASs such as PFBA, PFPeA, PFHxA showed desorption behavior and long-chained PFASs showed increased removal towards the end of the experiment indicating agglomeration or micelle development. Linear isomers of PFOS, PFHxS, and perfluorooctane sulfonamide (FOSA) had greater column removal efficiencies using GAC (and also for AE at greater bed volume throughput) than the branched and this difference increased at greater bed volume throughputs. The GAC and AE columns showed a poor correlation between DOC and PFAS removal efficiency. The results indicate that designers and operators of AE and GAC treatment processes must take into consideration the selective nature of PFAS removal and associated desorption of short-chain PFCAs during co-removal of multiple PFASs. Copyright © 2017 Elsevier Ltd. All rights reserved.

Human exposure to per- and polyfluoroalkyl substances (PFASs) via house dust in Korea: Implication to exposure pathway.

PubMed

Tian, Zhexi; Kim, Seung-Kyu; Shoeib, Mahiba; Oh, Jeong-Eun; Park, Jong-Eun

2016-05-15

A wide range of per- and polyfluoroalkyl substances (PFASs), including fluorotelomer alcohols (FTOHs), perfluorooctane sulfonamidoethanols (FOSEs), perfluoroalkyl carboxylic acids (PFCAs), and perfluoroalkane sulfonic acids (PFSAs), were measured in fifteen house dust and two nonresidential indoor dust of Korea. Total concentrations of PFASs in house dust ranged from 29.9 to 97.6 ng g(-1), with a dominance of perfluorooctane sulfonic acid (PFOS), followed by 8:2 FTOH, N-Ethyl perfluorooctane sulfonamidoethanol (EtFOSE), perfluoroctanoic acid (PFOA). In a typical exposure scenario, the estimated daily intakes (EDIs) of total PFASs via house dust ingestion were 2.83 ng d(-1) for toddlers and 1.13 ng d(-1) for adults, which were within the range of the mean EDIs reported from several countries. For PFOA and PFOS exposure via house dust ingestion, indirect exposure (via precursors) was a minor contributor, accounting for 5% and 12%, respectively. An aggregated exposure (hereafter, overall-EDIs) of PFOA and PFOS occurring via all pathways, estimated using data compiled from the literature, were 53.6 and 14.8 ng d(-1) for toddlers, and 20.5 and 40.6 ng d(-1) for adults, respectively, in a typical scenario. These overall-EDIs corresponded to 82% (PFOA) and 92% (PFOS) of a pharmacokinetic model-based EDIs estimated from adults' serum data. Direct dietary exposure was a major contributor (>89% of overall-EDI) to PFOS in both toddlers and adults, and PFOA in toddlers. As for PFOA exposure of adults, however direct exposure via tap water drinking (37%) and indirect exposure via inhalation (22%) were as important as direct dietary exposure (41%). House dust-ingested exposure (direct+indirect) was responsible for 5% (PFOS in toddlers) and <1% (PFOS in adults, and PFOA in both toddlers and adults) of the overall-EDIs. In conclusion, house-dust ingestion was a minor contributor in this study, but should not be ignored for toddlers' PFOS exposure due to its significance in the worst-case scenario. Copyright © 2016 Elsevier B.V. All rights reserved.

EFFECTS OF PERFLUOROOCTANE SULFONATE (PFOS) ON THYROID HORMONE STATUS IN ADULT AND NEONATAL RATS

EPA Science Inventory

EFFECTS OF PERFLUOROOCTANE SULFONATE (PFOS) ON THYROID HORMONE STATUS IN ADULT AND NEONATAL RATS. M.N. Logan1, J.R. Thibodeaux2, R.G. Hanson2, C. Lau2. 1North Carolina Central University, Durham, NC, 2Reprod. Tox. Div. NHEERL, US EPA, Research Triangle Park, NC.

Perfluor...

Discovery of novel and cardioselective diltiazem-like calcium channel blockers via virtual screening.

PubMed

Carosati, Emanuele; Budriesi, Roberta; Ioan, Pierfranco; Ugenti, Maria P; Frosini, Maria; Fusi, Fabio; Corda, Gaetano; Cosimelli, Barbara; Spinelli, Domenico; Chiarini, Alberto; Cruciani, Gabriele

2008-09-25

With the effort to discover new chemotypes blocking L-type calcium channels (LTCCs), ligand-based virtual screening was applied with a specific interest toward the diltiazem binding site. Roughly 50000 commercially available compounds served as a database for screening. The filtering through predicted pharmacokinetic properties and structural requirements reduced the initial database to a few compounds for which the similarity was calculated toward two template molecules, diltiazem and 4-chloro-Ncyclopropyl- N-(4-piperidinyl)benzene-sulfonamide, the most interesting hit of a previous screening experiment. For 18 compounds, inotropic and chronotropic activity as well as the vasorelaxant effect on guinea pig were studied "in vitro", and for the most promising, binding studies to the diltiazem site were carried out. The procedure yielded several hits, confirming in silico techniques to be useful for finding new chemotypes. In particular, N-[2-(dimethylamino)ethyl]-3-hydroxy-2-naphthamide, N,Ndimethyl- N'-(2-pyridin-3-ylquinolin-4-yl)ethane-1,2-diamine, 2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]- N,N-dimethylethanamine (carbinoxamine), and 7-[2-(diethylamino)ethoxy]-2H-chromen-2-one revealed interesting activity and binding to the benzothiazepine site.

Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide.

PubMed

Shakuntala, K; Naveen, S; Lokanath, N K; Suchetan, P A

2017-05-01

The crystal structures of three isomeric compounds of formula C 14 H 13 Cl 2 NO 2 S, namely 3,5-di-chloro- N -(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro- N -(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro- N -(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal structure of (I) features N-H⋯O hydrogen-bonded R 2 2 (8) loops inter-connected via C (7) chains of C-H⋯O inter-actions, forming a three-dimensional architecture. The structure also features π-π inter-actions [ Cg ⋯ Cg = 3.6970 (14) Å]. In (II), N-H⋯O hydrogen-bonded R 2 2 (8) loops are inter-connected via π-π inter-actions [inter-centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C (4) chains of N-H⋯O hydrogen-bonded mol-ecules running parallel to [010] are connected via C-H⋯π inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π-π inter-actions [inter-centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

Bis(diethylenetriamine-kappa3N)nickel(II) 5-amino-1,3,4-thiadiazole-2-sulfonamidate chloride monohydrate.

PubMed

Liu-Gonzalez, M; Sanz-Ruiz, F; Chufán, E E; Pedregosa, J C; Borras-Tortonda, J

2001-10-01

In the X-ray crystal structure of the title complex, [Ni(C(4)H(13)N(3))(2)](C(2)H(3)N(4)O(2)S(2))Cl.H(2)O, the coordination polyhedron is composed of non-centrosymmetric [Ni(diethylenetriamine)(2)](2+) cations in which the triamine ligands coordinate to the metal centre as tridentate ligands in a facial position. The Ni(II) ions are linked to six N atoms in an octahedral arrangement, slightly compressed in one extreme. The sulfonamide behaves as a counter-ion instead of as a ligand. Important information about the deprotonated sulfonamide group conformation has been obtained.

Spatial and temporal trends of poly- and perfluoroalkyl substances in fish fillets and water collected from pool 2 of the Upper Mississippi River.

PubMed

Newsted, John L; Holem, Ryan; Hohenstein, Gary; Lange, Cleston; Ellefson, Mark; Reagen, William; Wolf, Susan

2017-11-01

In 2011, poly- and perfluoroalkyl substances (PFASs) were analyzed in surface water and fish fillet samples taken from Pool 2 of the Upper Mississippi River, a 33-mile stretch inclusive of the Minneapolis/St. Paul, Minnesota (USA) metropolitan area. Approximately 100 each of bluegill, freshwater drum, smallmouth bass, and white bass were sampled within the study area. Surface water samples were also collected from each of the 10 sampling reaches established for the study. Water and fillet samples were analyzed for perfluorinated carboxylic acids (C4-C12), perfluorinated sulfonic acids (C4, C6, and C8), and perfluorooctane sulfonamide. Perfluorooctane sulfonate (PFOS) was observed with the greatest frequency in fish fillets and ranged from 3.0 to 760 ng/g wet weight. Mean (geometric) PFOS concentrations in bluegill, freshwater drum, smallmouth bass, and white bass were 20, 28, 29, and 58 ng/g wet weight, respectively. When compared with fish data collected in 2009, a significant reduction (p < 0.05) in PFOS concentrations was noted. This finding was confirmed based on data from studies conducted in 2012 and 2013. Overall, between 2009 and 2013, PFOS concentrations decreased by 65, 76, and 50% for bluegill, freshwater drum, and white bass, respectively (44% decrease for smallmouth bass from 2009 to 2012). These declines in fish PFOS concentrations are consistent with ongoing efforts to effectively control sources of PFASs to the Mississippi River. Environ Toxicol Chem 2017;36:3138-3147. © 2017 SETAC. © 2017 SETAC.

Highly elevated levels of perfluorooctane sulfonate and other perfluorinated acids found in biota and surface water downstream of an international airport, Hamilton, Ontario, Canada.

PubMed

de Solla, S R; De Silva, A O; Letcher, R J

2012-02-01

Per- and poly-fluorinated compounds (PFCs), which include perfluorinated carboxylates (PFCAs) and sulfonates (PFSAs) and various precursors, are used in a wide variety of industrial, commercial and domestic products. This includes aqueous film forming foam (AFFF), which is used by military and commercial airports as fire suppressants. In a preliminary assessment prior to this study, very high concentrations (>1 ppm wet weight) of the PFSA, perfluorooctane sulfonate (PFOS), were discovered in the plasma of snapping turtles (Chelydra serpentina) collected in 2008 from Lake Niapenco in southern Ontario, Canada. We presently report on a suite of C(6) to C(15) PFCAs, C(4), C(6), C(8) and C(10) PFSAs, several PFC precursors (e.g. perfluorooctane sulfonamide, PFOSA), and a cyclic perfluorinated acid used in aircraft hydraulic fluid, perfluoroethylcyclohexane sulfonate (PFECHS) in surface water from the Welland River and Lake Niapenco, downstream of the John C. Munro International Airport, Hamilton, Ontario, Canada. Amphipods, shrimp, and water were sampled from the Welland River and Lake Niapenco, as well as local references. The same suite of PFCs in turtle plasma from Lake Niapenco was compared to those from other southern Ontario sites. PFOS dominated the sum PFCs in all substrates (e.g., >99% in plasma of turtles downstream the Hamilton Airport, and 72.1 to 94.1% at all other sites). PFOS averaged 2223(±247.1SE) ng/g in turtle plasma from Lake Niapenco, and ranged from 9.0 to 171.4 elsewhere. Mean PFOS in amphipods and in water were 518.1(±83.8)ng/g and 130.3(±43.6) ng/L downstream of the airport, and 19.1(±2.7) ng/g and 6.8(±0.5) ng/L at reference sites, respectively. Concentrations of selected PFCs declined with distance downstream from the airport. Although there was no known spill event or publicly reported use of AFFF associated with a fire event at the Hamilton airport, the airport is a likely major source of PFC contamination in the Welland River. Crown Copyright © 2011. Published by Elsevier Ltd. All rights reserved.

The role of the acidity of N-heteroaryl sulfonamides as inhibitors of bcl-2 family protein-protein interactions.

PubMed

Touré, B Barry; Miller-Moslin, Karen; Yusuff, Naeem; Perez, Lawrence; Doré, Michael; Joud, Carol; Michael, Walter; DiPietro, Lucian; van der Plas, Simon; McEwan, Michael; Lenoir, Francois; Hoe, Madelene; Karki, Rajesh; Springer, Clayton; Sullivan, John; Levine, Kymberly; Fiorilla, Catherine; Xie, Xiaoling; Kulathila, Raviraj; Herlihy, Kara; Porter, Dale; Visser, Michael

2013-02-14

Overexpression of the antiapoptotic members of the Bcl-2 family of proteins is commonly associated with cancer cell survival and resistance to chemotherapeutics. Here, we describe the structure-based optimization of a series of N-heteroaryl sulfonamides that demonstrate potent mechanism-based cell death. The role of the acidic nature of the sulfonamide moiety as it relates to potency, solubility, and clearance is examined. This has led to the discovery of novel heterocyclic replacements for the acylsulfonamide core of ABT-737 and ABT-263.

Modularity and three-dimensional isostructurality of novel synthons in sulfonamide-lactam cocrystals.

PubMed

Bolla, Geetha; Mittapalli, Sudhir; Nangia, Ashwini

2015-07-01

The design of novel supramolecular synthons for functional groups relevant to drugs is an essential prerequisite for applying crystal engineering in the development of novel pharmaceutical cocrystals. It has been convincingly shown over the past decade that molecular level control and modulation can influence the physicochemical properties of drug cocrystals. Whereas considerable advances have been reported on the design of cocrystals for carboxylic acids and carboxamide functional groups, the sulfonamide group, which is a cornerstone of sulfa drugs, is relatively unexplored for reproducible heterosynthon-directed crystal engineering. The occurrence of synthons and isostructurality in sulfonamide-lactam cocrystals (SO2NH2⋯CONH hydrogen bonding) is analyzed to define a strategy for amide-type GRAS (generally recognized as safe) coformers with sulfonamides. Three types of supramolecular synthons are identified for the N-H donor of sulfonamide hydrogen bonding to the C=O acceptor of amide. Synthon 1: catemer synthon C 2 (1)(4) chain motif, synthon 2: dimer-cyclic ring synthon R 2 (2)(8)R 4 (2)(8) motifs, and synthon 3: dimer-catemer synthon of R 2 (2)(8)C 1 (1)(4)D notation. These heterosynthons of the cocrystals observed in this study are compared with the N-H⋯O dimer R 2 (2)(8) ring and C(4) chain motifs of the individual sulfonamide structures. The X-ray crystal structures of sulfonamide-lactam cocrystals exhibit interesting isostructurality trends with the same synthon being present. One-dimensional, two-dimensional and three-dimensional isostructurality in crystal structures is associated with isosynthons and due to their recurrence, novel heterosynthons for sulfonamide cocrystals are added to the crystal engineer's toolkit. With the predominance of sulfa drugs in medicine, these new synthons provide rational strategies for the design of binary and potentially ternary cocrystals of sulfonamides.

Molecularly imprinted polymer online solid-phase extraction coupled with high-performance liquid chromatography-UV for the determination of three sulfonamides in pork and chicken.

PubMed

He, Jinxing; Wang, Shuo; Fang, Guozhen; Zhu, Huaping; Zhang, Yan

2008-05-14

A selective imprinted amino-functionalized silica gel sorbent was prepared by combining a surface molecular imprinting technique with a sol-gel process for online solid-phase extraction-HPLC determination of three trace sulfonamides in pork and chicken muscle. The imprinted functionalized silica gel sorbent exhibited selectivity and fast kinetics for the adsorption and desorption of sulfonamides. With a sample loading flow rate of 4 mL min (-1) for 12.5 min, enhancement factors and detection limits for three sulfonamides ( S/ N = 3) were achieved. The precision (RSD) for nine replicate online sorbent extractions of 5 microg L (-1) sulfonamides was less than 4.5%. The sorbent also offered good linearity ( r (2) > 0.99) for online solid-phase extraction of trace levels of sulfonamides. The method was applied to the determination of sulfonamides in pork and chicken muscle samples. The prepared polymer sorbent shows promise for online solid-phase extraction for HPLC determination of trace levels of sulfonamides in pork and chicken samples.

Adsorption behavior and mechanism of chloramphenicols, sulfonamides, and non-antibiotic pharmaceuticals on multi-walled carbon nanotubes.

PubMed

Zhao, Heng; Liu, Xue; Cao, Zhen; Zhan, Yi; Shi, Xiaodong; Yang, Yi; Zhou, Junliang; Xu, Jiang

2016-06-05

The adsorption behavior of different emerging contaminants (3 chloramphenicols, 7 sulfonamides, and 3 non-antibiotic pharmaceuticals) on five types of multi-walled carbon nanotubes (MWCNTs), and the underlying factors were studied. Adsorption equilibriums were reached within 12h for all compounds, and well fitted by the Freundlich isotherm model. The adsorption affinity of pharmaceuticals was positively related to the specific surface area of MWCNTs. The solution pH was an important parameter of pharmaceutical adsorption on MWCNTs, due to its impacts on the chemical speciation of pharmaceuticals and the surface electrical property of MWCNTs. The adsorption of ionizable pharmaceuticals decreased in varying degrees with the increased ionic strength. MWCNT-10 was found to be the strongest adsorbent in this study, and the Freundlich constant (KF) values were 353-2814mmol(1-n)L(n)/kg, 571-618mmol(1-n)L(n)/kg, and 317-1522mmol(1-n)L(n)/kg for sulfonamides, chloramphenicols, and non-antibiotic pharmaceuticals, respectively. The different adsorption affinity of sulfonamides might contribute to the different hydrophobic of heterocyclic substituents, while chloramphenicols adsorption was affected by the charge distribution in aromatic rings via substituent effects. Copyright © 2016 Elsevier B.V. All rights reserved.

Association between thyroid profile and perfluoroalkyl acids: Data from NHNAES 2007–2008

DOE Office of Scientific and Technical Information (OSTI.GOV)

Jain, Ram B., E-mail: Jain.ram.b@gmail.com

The effect of six perfluoroalkyl acids (PFAAs), namely, perfluorooctane sulfonate (PFOS), perfluorooctanoic acid (PFOA), perfluorodecanoic acid (PFDE), perfluorohexane sulfonic acid (PFHxS), 2-(N-methyl-perfluorooctane sulfonamide) acetic acid (MPAH), and perfluorononanoic acid (PFNA) on the levels of six thyroid function variables, namely, thyroid stimulating hormone (TSH), free and total thyroxine (FT4, TT4), free and total triiodothyronine (FT3, TT3), and thyroglobulin (TGN) was evaluated. Data from National Health and Nutrition Examination Survey for the years 2007–2008 were used for this evaluation. TSH levels increased with increase in levels of PFOA (p<0.01). There were no statistically significant associations between the levels of FT3, and FT4more » with the levels of any of the six PFAAs. Levels of TT3 were found to increase with the levels of PFOA (p=0.01) and TT4 levels were found to increase with increase in PFHxS levels (p<0.01). Males had statistically significantly higher levels of FT3 than females and females had statistically significantly higher levels of TT4 than males. As compared to non-Hispanics whites and Hispanics, non-Hispanic blacks had lower levels of TSH, FT3, TT3, and TT4 but Hispanics had the lowest levels of TGN. Age was negatively associated with FT3 and TT3 but positively associated with FT4 and TT4. Non-smokers had higher levels of TSH and TT4 than smokers and smokers had higher levels of FT3 and TGN than non-smokers. Iodine deficiency was associated with increased levels of TSH, TT3, TT4, and TGN. -- Highlights: • Levels of total triiodothyronine were found to increase with the levels of PFOA. • Total thyroxine increased with increase in levels of perfluorohexane sulfonic acid. • There was a positive association between the levels of PFOA and TSH. • Iodine deficiency was associated with elevated levels of TSH, total T3 and T4. • Iodine deficiency was associated with elevated levels of thyroglobulin.« less

Circulating levels of perfluoroalkyl substances are associated with dietary patterns – A cross sectional study in elderly Swedish men and women

DOE Office of Scientific and Technical Information (OSTI.GOV)

Sjogren, Per, E-mail: per.sjogren@pubcare.uu.se

Background: In our daily life, we are exposed to perfluoroalkyl substances (PFAS) with possible health implications. The main exposure route for these substances is diet but comparative studies on how dietary habits influence exposure are lacking. Objectives: To examine the relations between blood levels of PFAS and adherence to three predefined dietary patterns (a WHO recommended diet, a Mediterranean-like diet, and a Low-Carbohydrate High-Protein (LCHP) diet) in an elderly Swedish population. Methods: Dietary data from 7-day food records and serum concentrations of PFAS were obtained from a 70-year-old Swedish population (n=844), the Prospective Investigation of the Vasculature in Uppsala Seniorsmore » (PIVUS) study. The Healthy Diet Indicator score (based on WHO recommendations), the Mediterranean Diet Score and LCHP score were used to assess adherence. Multivariate linear regression was used to assess the associations between eight major PFAS and adherence to each dietary pattern. Results: The WHO recommended diet was positively associated with perfluorohexane sulfonic acid (PFHxS). The LCHP diet was positively related to four out of eight PFAS; namely, perfluorooctane sulfonic acid (PFOS), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA) and perfluoroundecanoic acid (PFUnDA). The Mediterranean-like diet was positively associated with most PFAS; namely perfluorooctanoic acid (PFOA), perfluorooctane sulfonamide (PFOSA), PFHxS, PFNA, PFDA, and PFUnDA. Conclusions: All dietary patterns were positively associated with blood levels of PFAS. The highest body burden of PFAS was found in individuals with high adherence to a Mediterranean-like diet, whilst individuals who more closely followed the officially recommended diet displayed a lower body burden of these compounds. - Highlights: • Perfluoroalkyl substances (PFAS) quantified in blood of 70-y-old Swedish subjects. • Adherence to predefined dietary patterns was associated with circulating PFAS. • A Mediterranean-like diet was positively associated with most circulating PFAS. • A low-carbohydrate high-protein diet was positively related to some PFAS in blood. • A WHO-recommended diet was only related to higher circulating levels of PFHxS.« less

Polymorphism in R-tamsulosin (an alpha blocker): The unexpected manifestation of a sulfonamide⋯o-diethoxybenzene heterosynthon

NASA Astrophysics Data System (ADS)

Nanubolu, Jagadeesh Babu; Sridhar, Balasubramanian; Ravikumar, Krishnan

2014-12-01

A two point Nsbnd H⋯O dimer or an infinite catemer are the most preferred motifs/synthons for sulfonamide structures. Such synthons are known to be so robust that they are only disrupted in the presence of highly activated O acceptors such as pyridine-N-oxide and sulfoxide. We demonstrate in this article that a multi-point synthon offered by much weaker ethoxy O and amine N acceptors can however strongly compete and disrupt the robust sulfonamide homosynthons. This has been illustrated with the synthon analysis in three polymorphic crystal structures of R-tamsulosin, an active drug used in the treatment of Benign Prostatic Hyperplasia (BPH) and its hydrochloride salt. These crystalline solids are characterized by Single crystal X-ray diffraction (SC-XRD), powder X-ray diffraction (PXRD), Fourier Transform Infrared (FT-IR) and Raman spectroscopy. Forms I, II of the free base and hydrochloride salt crystallize in the monoclinic P21, C2, and P21 space groups respectively with two molecules in the asymmetric unit (Z‧ = 2), whereas, form III of freebase crystallize in the orthorhombic P212121 space group with Z‧ = 1. Remarkably, all four crystal structures contain a totally unexpected sulfonamide⋯o-diethoxybenzene heterosynthon. The multi-point motifs observed in polymorphs are relatively stronger than those in the hydrochloride salt because of the gauche conformation of the tamsulosin linker chain which renders an additional hydrogen bond interaction with amine N acceptor, and resemble the crown ether sulfonamide recognition pattern. Observation of this new heterosynthon offers potential scope in the design of pharmaceutical cocrystals for sulfonamide bearing drug molecules. The present study also presents a detailed hydrogen bond motif analysis in 310 primary sulfonamide structures culled from the latest version of Cambridge Structural Database (CSD). The role of various competing groups is discussed in the context of understanding the most recurring sulfonamide homo and heterosynthons.

The Role of the Acidity of N-Heteroaryl Sulfonamides as Inhibitors of Bcl-2 Family Protein–Protein Interactions

PubMed Central

2013-01-01

Overexpression of the antiapoptotic members of the Bcl-2 family of proteins is commonly associated with cancer cell survival and resistance to chemotherapeutics. Here, we describe the structure-based optimization of a series of N-heteroaryl sulfonamides that demonstrate potent mechanism-based cell death. The role of the acidic nature of the sulfonamide moiety as it relates to potency, solubility, and clearance is examined. This has led to the discovery of novel heterocyclic replacements for the acylsulfonamide core of ABT-737 and ABT-263. PMID:24900652

Complexes possessing rare "tertiary" sulfonamide nitrogen-to-metal bonds of normal length: fac-[Re(CO)3(N(SO2R)dien)]PF6 complexes with hydrophilic sulfonamide ligands.

PubMed

Abhayawardhana, Pramuditha L; Marzilli, Patricia A; Fronczek, Frank R; Marzilli, Luigi G

2014-01-21

Tertiary sulfonamide nitrogen-to-metal bonds of normal length are very rare. We recently discovered such a bond in one class of fac-[Re(CO)3(N(SO2R)(CH2Z)2)](n) complexes (Z = 2-pyridyl) with N(SO2R)dpa ligands derived from di-(2-picolyl)amine (N(H)dpa). fac-[M(CO)3(N(SO2R)(CH2Z)2)](n) agents (M = (186/188)Re, (99m)Tc) could find use as radiopharmaceutical bioconjugates when R is a targeting moiety. However, the planar, electron-withdrawing 2-pyridyl groups of N(SO2R)dpa destabilize the ligand to base and create relatively rigid chelate rings, raising the possibility that the rare M-N(sulfonamide) bond is an artifact of a restricted geometry. Also, the hydrophobic 2-pyridyl groups could cause undesirable accumulation in the liver, limiting future use in radiopharmaceuticals. Our goal is to identify a robust, hydrophilic, and flexible N(CH2Z)2 chelate framework. New C2-symmetric ligands, N(SO2R)(CH2Z)2 with (Z = CH2NH2; R = Me, dmb, or tol), were prepared by treating N(H)dien(Boc)2, a protected diethylenetriamine (N(H)dien) derivative, with methanesulfonyl chloride (MeSO2Cl), 3,5-dimethylbenzenesulfonyl chloride (dmbSO2Cl), and 4-methylbenzenesulfonyl chloride (tolSO2Cl). Treatment of fac-[Re(CO)3(H2O)3](+) with these ligands, designated as N(SO2R)dien, afforded new fac-[Re(CO)3(N(SO2R)dien)]PF6 complexes. Comparing the fac-[Re(CO)3(N(SO2Me)dien)]PF6 and fac-[Re(CO)3(N(SO2Me)dpa)]PF6 complexes, we find that the Re(I)-N(sulfonamide) bonds are normal in length and statistically identical and that the methyl (13)C NMR signal has an unusually upfield shift compared to that in the free ligand. We attribute this unusual upfield shift to the fact that the sulfonamide N undergoes an sp(2)-to-sp(3) rehybridization upon coordination to Re(I) in both complexes. Thus, the sulfonamide N of N(SO2R)dien ligands is a good donor, even though the chelate rings are conformationally flexible. Addition of the strongly basic and potentially monodentate ligand, 4-dimethylaminopyridine, did not affect the fac-[Re(CO)3(N(SO2tol)dien)]PF6 complex, even after several weeks. This complex is also stable to heat in aqueous solution. These results indicate that N(SO2R)dien ligands form fac-[Re(CO)3(N(SO2R)dien)]PF6 complexes sufficiently robust to be utilized for radiopharmaceutical development.

Smartphone app-based/portable sensor for the detection of fluoro-surfactant PFOA.

PubMed

Fang, Cheng; Zhang, Xian; Dong, Zhaomin; Wang, Liang; Megharaj, Mallavarapu; Naidu, Ravi

2018-01-01

We developed a smartphone app-based monitoring tool for the detection of anionic surfactants (AS), including perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS). Akin to the methylene blue active substances (MBAS), liquid-phase extraction (LPE) is employed to extract the hydrophobic ion-pair of dye (ethyl violet)-AS to an organic phase (ethyl acetate). The colour (RGB) of the organic phase is read using a smartphone camera with the help of a reading kit. The value of RGB is carefully corrected and linked to the concentration of ASs with a standard deviation of <10% in the 10-1000 ppb (part per billion) range. In order to avoid the interference arising from inorganic anions (such as those found in tap water and groundwater), the water sample is pre-treated either by solid-phase extraction (SPE), which takes ∼30 min, or by dual liquid-phase extraction (dual-LPE, developed by us), which takes ∼5 min. In the latter case, the organic phase of the first LPE (equilibrium with water sample) is transferred and subjected to a second LPE (equilibrium with Milli-Q water) to remove any potential background interference. In the meantime, SPE can also pre-concentrate ASs at 100-1000 times (in volume) to benefit the sensitivity. Consequently, our smartphone app can detect PFOA spiked in tap/groundwater with an LOD of 10 ppb (∼12 nM, dual-LPE of ∼5 min), or 0.5 ppb (∼1.2 nM, SPE of ∼3 h), suggesting that it has the potential to succeed as a pre-screening tool for on-site application and in common laboratory tests. Copyright © 2017 Elsevier Ltd. All rights reserved.

Monoclonal antibodies with group specificity toward sulfonamides: selection of hapten and antibody selectivity.

PubMed

Wang, Zhanhui; Beier, Ross C; Sheng, Yajie; Zhang, Suxia; Jiang, Wenxiao; Wang, Zhaopeng; Wang, Jin; Shen, Jianzhong

2013-05-01

Immunoassays based on the current available antibodies for large multi-sulfonamide screening programs have suffered from high selectivity for individual sulfonamides and a wide range of selectivities for different sulfonamides. In this study, five synthesized haptens, HS, BS, CS, SA10, and TS and two sulfonamides, SG and SMX were used as haptens, which may or may not contain a ring structure at the N1 position of the sulfonamides, were selected to evaluate the effectiveness for producing group-specific monoclonal antibodies (MAbs). Mice immunized with three different two-ring haptens were used for hybridoma production, which resulted in three unique MAbs recognizing 10, 13, and 15 sulfonamides showing 50 % inhibition (IC50) at concentrations below 100 ng mL(-1). MAb 4D11 derived from one novel immunizing hapten could recognize 12 sulfonamides with IC50 values ranging from 1.2 to 12.4 ng mL(-1), almost within 1 order of magnitude. These produced MAbs show lower IC50 values in addition to significantly improved group specificity compared with previously generated MAbs. This study clearly indicates that the careful selection of the immunizing hapten has an important effect on the specificity of the generated antibodies.

Perfluoroalkyl and polyfluoroalkyl substances removal in a full-scale tropical constructed wetland system treating landfill leachate.

PubMed

Yin, Tingru; Chen, Huiting; Reinhard, Martin; Yi, Xinzhu; He, Yiliang; Gin, Karina Yew-Hoong

2017-11-15

Landfill leachate is often an important source of emerging organic contaminants including perfluoroalkyl and polyfluoroalkyl substances (PFASs) requiring proper treatment to protect surface water and groundwater resources. This study investigated the occurrence of PFASs in the leachate of a capped landfill site in Singapore and the efficacy of PFASs removal during flow through a constructed wetland (CW) treatment system. The CW treatment system consists of equalization tank, aeration lagoons, sedimentation tank, reed beds and polishing ponds. Target compounds included 11 perfluoroalkyl acids (PFAAs) (7 perfluoroalkyl carboxylic acids (PFCAs) and 4 perfluoroalkane sulfonates (PFSAs)) and 7 PFAA precursors. Although total PFASs concentrations in the leachate varied widely (1269 to 7661 ng/L) over the one-year sampling period, the PFASs composition remained relatively stable with PFCAs consistently being predominant (64.0 ± 3.8%). Perfluorobutane sulfonate (PFBS) concentrations were highly correlated with total PFASs concentrations and could be an indicator for the release of PFASs from this landfill. The release of short-chain PFAAs strongly depended on precipitation whereas concentrations of the other PFASs appeared to be controlled by partitioning. Overall, the CW treatment system removed 61% of total PFASs and 50-96% of individual PFASs. PFAAs were removed most efficiently in the reed bed (42-49%), likely due to the combination of sorption to soils and sediments and plant uptake, whereas most of the PFAA precursors (i.e. 5:3 fluorotelomer carboxylate (5:3 acid), N-substituted perfluorooctane sulfonamides (N-MeFOSAA and N-EtFOSAA)) were removed in the aeration lagoon (>55%) by biodegradation. The sedimentation tank and polishing ponds were relatively inefficient, with only 7% PFASs removal. Copyright © 2017 Elsevier Ltd. All rights reserved.

N-(1-Allyl-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Abderrafia, Hafid; Saadi, Mohamed; El Ammari, Lahcen

2013-11-30

The asymmetric unit of the title compound, C17H17N3O2S, contains two independent mol-ecules linked by an N-H⋯O hydrogen bond. The mol-ecules show different conformations. In the first mol-ecule, the fused five- and six-membered ring system is almost perpendicular to the plane through the atoms forming the allyl group, as indicated by the dihedral angle of 85.1 (4)°. The dihedral angle with the methyl-benzene-sulfonamide group is 78.8 (1)°. On the other hand, in the second mol-ecule, the dihedral angles between the indazole plane and the allyl and methyl-benzene-sulfonamide groups are 80.3 (3) and 41.5 (1)°, respectively. In the crystal, mol-ecules are further linked by N-H⋯N and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Per- and polyfluoroalkyl substances (PFASs) in San Francisco Bay wildlife: Temporal trends, exposure pathways, and notable presence of precursor compounds.

PubMed

Sedlak, Margaret D; Benskin, Jonathan P; Wong, Adam; Grace, Richard; Greig, Denise J

2017-10-01

Concentrations of perfluorooctane sulfonate (PFOS) in San Francisco Bay (SF Bay) wildlife have historically been among the highest reported globally. To track continuing exposures to PFASs and assess the impact of the 2002 phase-out of production of PFOS and related chemicals in the US, nine perfluoroalkyl carboxylic acids (PFCAs; C4-C12), three perfluoroalkyl sulfonic acids (PFSAs; C4, C6, C8) and perfluorooctane sulfonamide (PFOSA, a PFOS precursor) were measured in SF Bay cormorant eggs in 2012 and harbor seal serum sampled between 2009 and 2014. PFOS remained the dominant perfluoroalkyl acid (PFAA) in both cormorant eggs (36.1-466 ng/g) and seals (12.6-796 ng/g) from 2012 and 2014, respectively. Concentrations in seal and bird eggs from the South Bay have declined approximately 70% in both matrices. To elucidate potential pathways of exposure, prey fish, sediments and wastewater effluent were analyzed for PFASs, and in the case of sediment and effluent, a suite of PFAA precursors. PFOS was the dominant PFAA in prey fish and sediment. In effluent, different mixtures of PFAAs were measured, with PFOS, PFHxA, and PFOA detected in the highest concentrations. Polyfluoroalkyl phosphate diesters (PFCA-precursors) were observed at concentrations over an order of magnitude higher than PFCAs in sediment, highlighting their importance as a potential, on-going source of PFCAs to SF Bay wildlife. These findings suggest that the PFOS phase-out has resulted in reduced burdens to wildlife in SF Bay, but that exposure to diverse and incompletely characterized PFASs continues. Copyright © 2017 Elsevier Ltd. All rights reserved.

Perfluoroalkyl substances (PFAS) including structural PFOS isomers in plasma from elderly men and women from Sweden: Results from the Prospective Investigation of the Vasculature in Uppsala Seniors (PIVUS).

PubMed

Salihovic, Samira; Kärrman, Anna; Lind, Lars; Lind, P Monica; Lindström, Gunilla; van Bavel, Bert

2015-09-01

Per- and polyfluoroalkyl substances (PFASs) are a class of compounds with unique chemical properties that have been shown useful in a wide variety of applications because they provide materials with reduced surface tension and exceptional non-stick properties. PFASs are commonly found in impregnation materials, coatings of papers and textiles, fire-fighting foams, pesticides, and cleaning agents. The potential for human exposure to PFASs is high because of their widespread distribution. The aim of this study was to investigate levels of PFASs in men and women from Sweden and to assess the influence of gender and parity among women. Levels of 13 PFASs were determined in plasma samples collected during 2001-2004 from 1016 (507 women) 70year-old participants from the population-based Prospective Study of the Vasculature in Uppsala Seniors (PIVUS). The PFASs studied were nine perfluorinated carboxylic acids (PFCAs), four perfluorinated sulfonic acids (PFSAs) and perfluorooctane sulfonamide (PFOSA). In addition, structural isomers of perfluorooctane sulfonic acid (PFOS) were determined in a subset of 398 individuals. The detection rates were high and the majority of the studied compounds were detected in more than 75% of the participants. Levels of the selected analytes were found to be similar to other studies of non-occupationally exposed populations. Gender differences were observed in levels of PFHpA which was higher in men, while PFHxS was higher in women. Parity among women was shown to have a minor effect on PFAS concentrations and we found primi- and multiparous women to have slightly lower levels of PFUnDA when compared to nulliparous women. Copyright © 2015 Elsevier Ltd. All rights reserved.

Spatial and temporal trends of perfluorinated compounds in Beluga Whales (Delphinapterus leucas) from Alaska.

PubMed

Reiner, Jessica L; O'Connell, Steven G; Moors, Amanda J; Kucklick, John R; Becker, Paul R; Keller, Jennifer M

2011-10-01

Wildlife from remote locations have been shown to bioaccumulate perfluorinated compounds (PFCs) in their tissues. Twelve PFCs, consisting of perfluorinated carboxylic (PFCA) and sulfonic (PFSA) acids as well as the perfluorooctane sulfonate (PFOS) precursor perfluorooctane sulfonamide (PFOSA), were measured in livers of 68 beluga whales (Delphinapterus leucas) collected from two subpopulations, Cook Inlet and eastern Chukchi Sea, in Alaska between 1989 and 2006. PFOS and PFOSA were the dominant compounds measured in both beluga stock populations, with overall median concentrations of 10.8 ng/g and 22.8 ng/g, respectively. Long-chain perfluorocarboxylates, PFCAs (9 to 14 carbons), were detected in more than 80% of the samples. Perfluoroundecanoic acid (PFUnA) and perfluorotridecanoic acid (PFTriA) made up a large percentage of the PFCAs measured with median concentrations of 8.49 ng/g and 4.38 ng/g, respectively. To compare differences in location, year, sex, and length, backward stepwise multiple regression models of the individual and total PFC concentrations were used. Spatially, the Cook Inlet belugas had higher concentrations of most PFCAs and PFOS (p < 0.05); however, these belugas had a lower median concentration of PFOSA when compared to belugas from the eastern Chukchi Sea (p < 0.05). Temporal trends indicated most PFCAs, PFHxS, PFOS, and PFOSA concentrations increased from 1989 to 2006 (p < 0.05). Males had significantly higher concentrations of PFTriA, ΣPFCA, and PFOS (p < 0.05). Perfluorononanic acid (PFNA) and PFOS showed a significant decrease in concentration with increasing animal length (p < 0.05). These observations suggest the accumulation of PFCs in belugas is influenced by year, location, sex, and length.

Contribution of precursor compounds to the release of per- and polyfluoroalkyl substances (PFASs) from waste water treatment plants (WWTPs).

PubMed

Eriksson, Ulrika; Haglund, Peter; Kärrman, Anna

2017-11-01

Per- and polyfluoroalkyl substances (PFASs) are ubiquitous in sludge and water from waste water treatment plants, as a result of their incorporation in everyday products and industrial processes. In this study, we measured several classes of persistent PFASs, precursors, transformation intermediates, and newly identified PFASs in influent and effluent sewage water and sludge from three municipal waste water treatment plants in Sweden, sampled in 2015. For sludge, samples from 2012 and 2014 were analyzed as well. Levels of precursors in sludge exceeded those of perfluoroalkyl acids and sulfonic acids (PFCAs and PFSAs), in 2015 the sum of polyfluoroalkyl phosphoric acid esters (PAPs) were 15-20ng/g dry weight, the sum of fluorotelomer sulfonic acids (FTSAs) was 0.8-1.3ng/g, and the sum of perfluorooctane sulfonamides and ethanols ranged from non-detected to 3.2ng/g. Persistent PFSAs and PFCAs were detected at 1.9-3.9ng/g and 2.4-7.3ng/g dry weight, respectively. The influence of precursor compounds was further demonstrated by an observed substantial increase for a majority of the persistent PFCAs and PFSAs in water after waste water treatment. Perfluorohexanoic acid (PFHxA), perfluorooctanoic acid (PFOA), perfluorohexane sulfonic acid (PFHxS), and perfluorooctane sulfonic acid (PFOS) had a net mass increase in all WWTPs, with mean values of 83%, 28%, 37% and 58%, respectively. The load of precursors and intermediates in influent water and sludge combined with net mass increase support the hypothesis that degradation of precursor compounds is a significant contributor to PFAS contamination in the environment. Copyright © 2017. Published by Elsevier B.V.

Relationship between peroxisome proliferator-activated receptor alpha activity and cellular concentration of 14 perfluoroalkyl substances in HepG2 cells.

PubMed

Rosenmai, Anna Kjerstine; Ahrens, Lutz; le Godec, Théo; Lundqvist, Johan; Oskarsson, Agneta

2018-02-01

Peroxisome proliferator-activated receptor alpha (PPARα) is a molecular target for perfluoroalkyl substances (PFASs). Little is known about the cellular uptake of PFASs and how it affects the PPARα activity. We investigated the relationship between PPARα activity and cellular concentration in HepG2 cells of 14 PFASs, including perfluoroalkyl carboxylates (PFCAs), perfluoroalkyl sulfonates and perfluorooctane sulfonamide (FOSA). Cellular concentrations were determined by high-performance liquid chromatography-tandem mass spectrometry and PPARα activity was determined in transiently transfected cells by reporter gene assay. Cellular uptake of the PFASs was low (0.04-4.1%) with absolute cellular concentrations in the range 4-2500 ng mg -1 protein. Cellular concentration of PFCAs increased with perfluorocarbon chain length up to perfluorododecanoate. PPARα activity of PFCAs increased with chain length up to perfluorooctanoate. The maximum induction of PPARα activity was similar for short-chain (perfluorobutanoate and perfluoropentanoate) and long-chain PFCAs (perfluorododecanoate and perfluorotetradecanoate) (approximately twofold). However, PPARα activities were induced at lower cellular concentrations for the short-chain homologs compared to the long-chain homologs. Perfluorohexanoate, perfluoroheptanoate, perfluorooctanoate, perfluorononanoate (PFNA) and perfluorodecanoate induced PPARα activities >2.5-fold compared to controls. The concentration-response relationships were positive for all the tested compounds, except perfluorooctane sulfonate PFOS and FOSA, and were compound-specific, as demonstrated by differences in the estimated slopes. The relationships were steeper for PFCAs with chain lengths up to and including PFNA than for the other studied PFASs. To our knowledge, this is the first report establishing relationships between PPARα activity and cellular concentration of a broad range of PFASs. Copyright © 2017 John Wiley & Sons, Ltd.

Concentrations and patterns of perfluoroalkyl acids in Georgia, USA surface waters near and distant to a major use source.

PubMed

Konwick, Brad J; Tomy, Gregg T; Ismail, Nargis; Peterson, James T; Fauver, Rebecca J; Higginbotham, David; Fisk, Aaron T

2008-10-01

Perfluoroalkyl acids (PFAAs) are widespread contaminants emanating from, among other sources, the production/degradation of fluorinated chemicals used in surface repellant applications, such as carpet manufacturing. The goal of the present study was to assess the concentrations of PFAAs, including perfluorooctane sulfonate (PFOS), perfluorooctanoic acid (PFOA), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA), perfluoroundecanoic acid (PFUA), and perfluorooctane sulfonamide (PFOSA), in surface waters both near a wastewater land application system (LAS) in Dalton (GA, USA), home to North America's largest carpet manufacturing site, and distant to this location (Altamaha River, GA, USA) to understand the fate of PFAAs in freshwater. Levels of PFAAs were high in the Conasauga River (GA, USA) downstream of the LAS (PFOA, 253-1,150 ng/L; PFOS, 192-318 ng/L; PFNA, 202-369 ng/L; PFDA, 30.1-113 ng/L; PFUA, 58.0-99.2 ng/L; PFOSA, 162-283 ng/L) and in streams and ponds in Dalton (PFOA, 49.9-299 ng/L; PFOS, 15.8-120 ng/L), and were among the highest measured at a nonspill or direct-release location. Perfluoroalkyl acids in the Altamaha River were much lower (PFOA, 3.0-3.1 ng/L; PFOS, 2.6-2.7 ng/L), but were a source of PFAAs to Georgia's estuaries. A preliminary hazard assessment indicated that concentrations of PFOS at two sites in the Conasauga River exceeded the threshold effect predicted for birds consuming aquatic organisms that are exposed continuously to the PFOS levels at these sites. Assuming that toxicity for all PFAAs quantified is equal to that of PFOS, the sum total PFAAs at two sites within the Conasauga River exceeded PFOS thresholds for aquatic and avian species, warranting additional research.

1H NMR-Based Metabolomic Analysis of Sub-Lethal Perfluorooctane Sulfonate Exposure to the Earthworm, Eisenia fetida, in Soil

PubMed Central

Lankadurai, Brian P.; Furdui, Vasile I.; Reiner, Eric J.; Simpson, André J.; Simpson, Myrna J.

2013-01-01

1H NMR-based metabolomics was used to measure the response of Eisenia fetida earthworms after exposure to sub-lethal concentrations of perfluorooctane sulfonate (PFOS) in soil. Earthworms were exposed to a range of PFOS concentrations (five, 10, 25, 50, 100 or 150 mg/kg) for two, seven and fourteen days. Earthworm tissues were extracted and analyzed by 1H NMR. Multivariate statistical analysis of the metabolic response of E. fetida to PFOS exposure identified time-dependent responses that were comprised of two separate modes of action: a non-polar narcosis type mechanism after two days of exposure and increased fatty acid oxidation after seven and fourteen days of exposure. Univariate statistical analysis revealed that 2-hexyl-5-ethyl-3-furansulfonate (HEFS), betaine, leucine, arginine, glutamate, maltose and ATP are potential indicators of PFOS exposure, as the concentrations of these metabolites fluctuated significantly. Overall, NMR-based metabolomic analysis suggests elevated fatty acid oxidation, disruption in energy metabolism and biological membrane structure and a possible interruption of ATP synthesis. These conclusions obtained from analysis of the metabolic profile in response to sub-lethal PFOS exposure indicates that NMR-based metabolomics is an excellent discovery tool when the mode of action (MOA) of contaminants is not clearly defined. PMID:24958147

Sulfonamide inhibition studies of two β-carbonic anhydrases from the ascomycete fungus Sordaria macrospora, CAS1 and CAS2.

PubMed

Vullo, Daniela; Lehneck, Ronny; Pöggeler, Stefanie; Supuran, Claudiu T

2018-12-01

The two β-carbonic anhydrases (CAs, EC 4.2.1.1) recently cloned and purified from the ascomycete fungus Sordaria macrospora, CAS1 and CAS2, were investigated for their inhibition with a panel of 39 aromatic, heterocyclic, and aliphatic sulfonamides and one sulfamate, many of which are clinically used agents. CAS1 was efficiently inhibited by tosylamide, 3-fluorosulfanilamide, and 3-chlorosulfanilamide (K I s in the range of 43.2-79.6 nM), whereas acetazolamide, methazolamide, topiramate, ethoxzolamide, dorzolamide, and brinzolamide were medium potency inhibitors (K I s in the range of 360-445 nM). CAS2 was less sensitive to sulfonamide inhibitors. The best CAS2 inhibitors were 5-amino-1,3,4-thiadiazole-2-sulfonamide (the deacetylated acetazolamide precursor) and 4-hydroxymethyl-benzenesulfonamide, with K I s in the range of 48.1-92.5 nM. Acetazolamide, dorzolamide, ethoxzolamide, topiramate, sulpiride, indisulam, celecoxib, and sulthiame were medium potency CAS2 inhibitors (K I s of 143-857 nM). Many other sulfonamides showed affinities in the high micromolar range or were ineffective as CAS1/2 inhibitors. Small changes in the structure of the inhibitor led to important differences of the activity. As these enzymes may show applications for the removal of anthropically generated polluting gases, finding modulators of their activity may be crucial for designing environmental-friendly CO 2 capture processes.

Structural characterization of new Schiff bases of sulfamethoxazole and sulfathiazole, their antibacterial activity and docking computation with DHPS protein structure.

PubMed

Mondal, Sudipa; Mandal, Santi M; Mondal, Tapan Kumar; Sinha, Chittaranjan

2015-01-01

New Schiff bases (1, 2) of substituted salicylaldehydes and sulfamethoxazole (SMX)/sulfathiazole (STZ) are synthesized and characterized by elemental analysis and spectroscopic data. Single crystal X-ray structure of one of the compounds (E)-4-((3,5-dichloro-2-hydroxybenzylidene)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (1c) has been determined. Antimicrobial activities of the Schiff bases and parent sulfonamides (SMX, STZ) have been examined against several Gram-positive and Gram-negative bacteria and sulfonamide resistant pathogens; the lowest MIC is observed for (E)-4-((3,5-dichloro-2-hydroxybenzylidene)amino)-N-(thiazol-2-yl)benzene sulfonamide (2c) (8.0 μg mL(-1)) and (E)-4-((3,5-dichloro-2-hydroxybenzylidene)amino)-N-(5-methylisoxazol-3-yl)benzene sulfonamide (1c) (16.0 μg mL(-1)) against sulfonamide resistant pathogens. DFT optimized structures of the Schiff bases have been used to carry out molecular docking studies with DHPS (dihydropteroate synthase) protein structure (downloaded from Protein Data Bank) using Discovery Studio 3.5 to find the most preferred binding mode of the ligand inside the protein cavity. The theoretical data have been well correlated with the experimental results. Cell viability assay and ADMET studies predict that 1c and 2c have good drug like characters. Copyright © 2015 Elsevier B.V. All rights reserved.

Development of monolith-based stir bar sorptive extraction and liquid chromatography tandem mass spectrometry method for sensitive determination of ten sulfonamides in pork and chicken samples.

PubMed

Huang, Xiaojia; Chen, Linli; Yuan, Dongxing

2013-08-01

A highly sensitive method was developed for the simultaneous determination of ten sulfonamides in pork and chicken samples by monolith-based stir bar sorptive extraction (SBSE) coupled to high-performance liquid chromatography tandem mass spectrometry. The samples were freeze-dried and extracted by acetonitrile, then enriched and further extracted by SBSE which was based on poly(vinylphthalimide-co-N,N-methylenebisacrylamide) monolith (SBSE-VPMB) as coating. To achieve optimum extraction performance of SBSE for sulfonamides, several parameters, including pH value and ionic strength in the sample matrix and extraction and desorption time, were investigated in detail. Under the optimal conditions, the limits of detection (S/N = 3) for target sulfonamides were 1.2-6.1 ng/kg in pork and 2.0-14.6 ng/kg in chicken, respectively. Real samples spiked at the concentration of 0.5 and 5.0 μg/kg showed recoveries above 55% and relative standard deviations below 12%. At the same time, the extraction performances of target sulfonamides on SBSE-VPMB were compared with other SBSE based on porous monolith and commercial SBSE.

Bis[μ-N-(pyridin-2-yl)methane­sulfon­amido-κ2 N:N′]silver(I)

PubMed Central

Hu, Hui-Ling; Yeh, Chun-Wei

2013-01-01

In the title compound, [Ag2(C6H7N2O2S)2], the AgI atom is coordinated by two N atoms from two N-(pyridin-2-yl)methane­sulfonamidate anions in a slightly bent linear geometry [N—Ag—N = 166.03 (7)°]. The AgI atoms are bridged by the N-(pyridin-2-yl)methane­sulfonamidate anions, forming a centrosymmetric dinuclear mol­ecule, in which the Ag⋯Ag distance is 2.7072 (4) Å. PMID:24860285

N-(1H-Indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2013-10-26

In the title compound, C14H13N3O3S, the fused ring system is almost planar, the largest deviation from the mean plane being 0.023 (2) Å, and makes a dihedral angle of 47.92 (10)° with the benzene ring of the benzene-sulfonamide moiety. In the crystal, mol-ecules are connected through N-H⋯O hydrogen bonds and weak C-H⋯O contacts, forming a two-dimensional network which is parallel to (010).

4-Methyl-N-(1-methyl-1H-indazol-5-yl)benzene-sulfonamide.

PubMed

Chicha, Hakima; Oulemda, Bassou; Rakib, El Mostapha; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

In the title compound, C15H15N3O2S, the fused ring system is close to planar, the largest deviation from the mean plane being 0.030 (2) Å, and makes a dihedral angle of 48.84 (9)° with the benzene ring belonging to the methyl-benzene-sulfonamide moiety. In the crystal, mol-ecules are -connected through N-H⋯N hydrogen bonds and weak C-H⋯O contacts, forming a two-dimensional network parallel to (001).

Ionic liquid-salt aqueous two-phase extraction based on salting-out coupled with high-performance liquid chromatography for the determination of sulfonamides in water and food.

PubMed

Han, Juan; Wang, Yun; Liu, Yan; Li, Yanfang; Lu, Yang; Yan, Yongsheng; Ni, Liang

2013-02-01

Ionic liquid-salt aqueous two-phase extraction coupled with high-performance liquid chromatography with ultraviolet detection was developed for the determination of sulfonamides in water and food samples. In the procedure, the analytes were extracted from the aqueous samples into the ionic liquid top phase in one step. Three sulfonamides, sulfamerazine, sulfamethoxazole, and sulfamethizole were selected here as model compounds for developing and evaluating the method. The effects of various experimental parameters in extraction step were studied using two optimization methods, one variable at a time and Box-Behnken design. The results showed that the amount of sulfonamides did not have effect on the extraction efficiency. Therefore, a three-level Box-Behnken experimental design with three factors, which combined the response surface modeling, was used to optimize sulfonamides extraction. Under the most favorable extraction parameters, the detection limits (S/N = 3) and quantification limits (S/N = 10) of the proposed method for the target compounds were achieved within the range of 0.15-0.3 ng/mL and 0.5-1.0 ng/mL from spiked samples, respectively, which are lower than or comparable with other reported approaches applied to the determination of the same compounds. Finally, the proposed method was successfully applied to the determination of sulfonamide compounds in different water and food samples and satisfactory recoveries of spiked target compounds in real samples were obtained.

Can profiles of poly- and Perfluoroalkyl substances (PFASs) in human serum provide information on major exposure sources?

PubMed

Hu, Xindi C; Dassuncao, Clifton; Zhang, Xianming; Grandjean, Philippe; Weihe, Pál; Webster, Glenys M; Nielsen, Flemming; Sunderland, Elsie M

2018-02-01

Humans are exposed to poly- and perfluoroalkyl substances (PFASs) from diverse sources and this has been associated with negative health impacts. Advances in analytical methods have enabled routine detection of more than 15 PFASs in human sera, allowing better profiling of PFAS exposures. The composition of PFASs in human sera reflects the complexity of exposure sources but source identification can be confounded by differences in toxicokinetics affecting uptake, distribution, and elimination. Common PFASs, such as perfluorooctanoic acid (PFOA), perfluorooctane sulfonic acid (PFOS) and their precursors are ubiquitous in multiple exposure sources. However, their composition varies among sources, which may impact associated adverse health effects. We use available PFAS concentrations from several demographic groups in a North Atlantic seafood consuming population (Faroe Islands) to explore whether chemical fingerprints in human sera provide insights into predominant exposure sources. We compare serum PFAS profiles from Faroese individuals to other North American populations to investigate commonalities in potential exposure sources. We compare individuals with similar demographic and physiological characteristics and samples from the same years to reduce confounding by toxicokinetic differences and changing environmental releases. Using principal components analysis (PCA) confirmed by hierarchical clustering, we assess variability in serum PFAS concentrations across three Faroese groups. The first principal component (PC)/cluster consists of C9-C12 perfluoroalkyl carboxylates (PFCAs) and is consistent with measured PFAS profiles in consumed seafood. The second PC/cluster includes perfluorohexanesulfonic acid (PFHxS) and the PFOS precursor N-ethyl perfluorooctane sulfonamidoacetate (N-EtFOSAA), which are directly used or metabolized from fluorochemicals in consumer products such as carpet and food packaging. We find that the same compounds are associated with the same exposure sources in two North American populations, suggesting generalizability of results from the Faroese population. We conclude that PFAS homologue profiles in serum provide valuable information on major exposure sources. It is essential to compare samples collected at similar time periods and to correct for demographic groups that are highly affected by differences in physiological processes (e.g., pregnancy). Information on PFAS homologue profiles is crucial for attributing adverse health effects to the proper mixtures or individual PFASs.

A sensitive method for the determination of Sulfonamides in seawater samples by Solid Phase Extraction and UV-Visible spectrophotometry

NASA Astrophysics Data System (ADS)

Errayess, Sophia Ait; Lahcen, Abdellatif Ait; Idrissi, Laila; Marcoaldi, Caterina; Chiavarini, Salvatore; Amine, Aziz

2017-06-01

The authors have developed a sensitive spectrophotometric method for determination of sulfonamide derivatives such as sulfanilamide (SAA), sulfadiazine (SDZ), sulfacetamide (SCT) sulfamethoxazole (SMX), sulfamerazine (SMR), sulfadimethoxine (SDX), sulfamethiazole (SMT) and Sulfathiazole (STZ). This method is based on the Bratton-Marshall reaction, which involves the diazotization of sulfonamides with sodium nitrite under acidic conditions, followed by coupling with N-(1-naphtyl) ethylenediamine dihydrochloride (NED) to form a pink colored compound. Therefore, the Bratton-Marshall method was modified by optimizing the reaction conditions, which allows us to determine a low concentration range of sulfonamides compared to the reported methods. The limits of detection and quantification obtained were 0.019-0.05 and 0.06-0.16 μg mL- 1, respectively. In comparison with other reported methods using different coupling agents, the proposed method was found to be the most simple and sensitive for sulfonamides determination. In this paper, the modified method was successfully employed for the determination of sulfonamides in drinking water, seawater and pharmaceutical and veterinary formulations. The purpose of this work is to optimize and develop a simple method for extraction and concentration of sulfonamides present as residues in seawater and their quantification with the recommended spectrophotometric method. Solid phase extraction (SPE) of sulfonamides from seawater samples was evaluated using Oasis HLB cartridges (3 mL, 540 mg). The recovery efficiency was investigated in the sulfonamides concentration range comprised between 0.19 and 126 ng mL- 1. The ease of use of this extraction method makes it very useful for routine laboratory work.

Reduction of N-hydroxy-sulfonamides, including N-hydroxy-valdecoxib, by the molybdenum-containing enzyme mARC.

PubMed

Havemeyer, Antje; Grünewald, Sanja; Wahl, Bettina; Bittner, Florian; Mendel, Ralf; Erdélyi, Péter; Fischer, János; Clement, Bernd

2010-11-01

Purification of the mitochondrial enzyme responsible for reduction of N-hydroxylated amidine prodrugs led to the identification of two newly discovered mammalian molybdenum-containing proteins, the mitochondrial amidoxime reducing components mARC-1 and mARC-2 (Gruenewald et al., 2008). These 35-kDa proteins represent a novel group of molybdenum proteins in eukaryotes as they form a molybdenum cofactor-dependent enzyme system consisting of three separate proteins (Havemeyer et al., 2006). Each mARC protein reduces N-hydroxylated compounds after reconstitution with the electron transport proteins cytochrome b(5) and b(5) reductase. In continuation of our drug metabolism investigations (Havemeyer et al., 2006; Gruenewald et al., 2008), we present data from reconstituted enzyme systems with recombinant human and native porcine enzymes showing the reduction of N-hydroxy-sulfonamides (sulfohydroxamic acids) to sulfonamides: the N-hydroxy-sulfonamide N-hydroxy-valdecoxib (N-hydroxy-4-[5-methyl-3-phenyl-4-isoxazolyl]-benzenesulfonamide) represents a novel cyclooxygenase (COX)-2 inhibitor and is therefore a drug candidate in the treatment of diseases associated with rheumatic inflammation, pain, and fever. It was synthesized as an analog of the known COX-2 inhibitor valdecoxib (4-[5-methyl-3-phenyl-4-isoxazolyl]-benzenesulfonamide) (Talley et al., 2000). N-Hydroxy-valdecoxib had low in vitro COX-2 activity but showed significant analgesic activity in vivo and a prolonged therapeutic effect compared with valdecoxib (Erdélyi et al., 2008). In this report, we demonstrate that N-hydroxy-valdecoxib is enzymatically reduced to its pharmacologically active metabolite valdecoxib. Thus, N-hydroxy-valdecoxib acts as prodrug that is activated by the molybdenum-containing enzyme mARC.

Preconception maternal and paternal exposure to persistent organic pollutants and birth size: the LIFE study.

PubMed

Robledo, Candace A; Yeung, Edwina; Mendola, Pauline; Sundaram, Rajeshwari; Maisog, Jose; Sweeney, Anne M; Barr, Dana Boyd; Louis, Germaine M Buck

2015-01-01

Persistent organic pollutants (POPs) are developmental toxicants, but the impact of both maternal and paternal exposures on offspring birth size is largely unexplored. We examined associations between maternal and paternal serum concentrations of 63 POPs, comprising five major classes of pollutants, with birth size measures. Parental serum concentrations of 9 organochlorine pesticides, 1 polybrominated biphenyl (PBB), 7 perfluoroalkyl chemicals (PFCs), 10 polybrominated diphenyl ethers (PBDEs), and 36 polychlorinated biphenyls (PCBs) were measured before conception for 234 couples. Differences in birth weight, length, head circumference, and ponderal index were estimated using multiple linear regression per 1-SD increase in natural log-transformed (ln-transformed) chemicals. Models were estimated separately for each parent and adjusted for maternal age, maternal prepregnancy body mass index (kilograms per meter squared) and other confounders, and all models included an interaction term between infant sex and each chemical. Among girls (n = 117), birth weight was significantly lower (range, 84-195 g) in association with a 1-SD increase in ln-transformed maternal serum concentrations of DDT, PBDE congeners 28 and 183, and paternal serum concentrations of PBDE-183 and PCB-167. Among boys (n = 113), maternal (PCBs 138, 153, 167, 170, 195, and 209 and perfluorooctane sulfonamide) and paternal (PCBs 172 and 195) serum concentrations of several POPs were statistically associated with lower birth weight (range, 98-170 g), whereas paternal concentrations of PBDEs (66, 99) were associated with higher birth weight. Differences in offspring head circumference, length, and ponderal index were also associated with parental exposures. Preconceptional maternal and paternal concentrations of several POPs were associated with statistically significant differences in birth size among offspring.

Preparation and Structural Properties of InIII–H Complexes

PubMed Central

Sickerman, Nathaniel S.; Henry, Renée M.; Ziller, Joseph W.

2013-01-01

The use of the tripodal ligands tris[(N'-tert-butylureaylato)-N-ethyl]aminato ([H3buea]3−) and the sulfonamide-based N,N',N"-[2,2',2"-nitrilotris(ethane-2,1-diyl)]tris(2,4,6-trimethylbenzene-sulfonamidato) ([MST]3−) has led to the synthesis of two structurally distinct In(III)–OH complexes. The first example of a five-coordinate indium(III) complex with a terminal hydroxide ligand, K[InIIIH3buea(OH)], was prepared by addition of In(OAc)3 and water to a deprotonated solution of H6buea. X-ray diffraction analysis, as well as FTIR and 1H NMR spectroscopic methods, provided evidence for the formation of a monomeric In(III)–OH complex. The complex contains an intramolecular hydrogen bonding (H-bonding) network involving the In(III)–OH unit and [H3buea]3− ligand, which aided in isolation of the complex. Isotope labeling studies verified the source of the hydroxo ligand as water. Treatment of the [InIIIMST] complex with a mixture of 15-crown-5 ether and NaOH led to isolation of the complex [15-crown-5⊃NaI-(μ-OH)-InIIIMST], whose solid-state structure was confirmed using X-ray diffraction methods. Nuclear magnetic resonance studies on this complex suggest it retains its heterobimetallic structure in solution. PMID:25309019

Nitrosamine-induced carcinogenesis. The alkylation of N-7 of guanine of nucleic acids of the rat by diethylnitrosamine, N-ethyl-N-nitrosourea and ethyl methanesulphonate

PubMed Central

Swann, P. F.; Magee, P. N.

1971-01-01

1. The extent of ethylation of N-7 of guanine in the nucleic acids of rat tissue in vivo by diethylnitrosamine, N-ethyl-N-nitrosourea and ethyl methanesulphonate was measured. 2. All compounds produced measurable amounts of 7-ethyl-guanine. 3. A single dose of diethylnitrosamine or N-ethyl-N-nitrosourea produced tumours of the kidney in the rat. Three doses of ethyl methanesulphonate produced kidney tumours, but a single dose did not. 4. A single dose of diethylnitrosamine produced twice as much ethylation of N-7 of guanine in DNA of kidney as did N-ethyl-N-nitrosourea. A single dose of both compounds induced kidney tumours, although of a different histological type. 5. A single dose of ethyl methanesulphonate produced ten times as much ethylation of N-7 of guanine in kidney DNA as did N-ethyl-N-nitrosourea without producing tumours. 6. The relevance of these findings to the hypothesis that alkylation of a cellular component is the mechanism of induction of tumours by nitroso compounds is discussed. PMID:5145908

40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

Code of Federal Regulations, 2013 CFR

2013-07-01

...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates...

40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

Code of Federal Regulations, 2014 CFR

2014-07-01

...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates...

40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

Code of Federal Regulations, 2012 CFR

2012-07-01

...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates...

40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

Code of Federal Regulations, 2011 CFR

2011-07-01

...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates...

4-Methyl-N-(1-methyl-1H-indazol-5-yl)benzene­sulfonamide

PubMed Central

Chicha, Hakima; Oulemda, Bassou; Rakib, El Mostapha; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

In the title compound, C15H15N3O2S, the fused ring system is close to planar, the largest deviation from the mean plane being 0.030 (2) Å, and makes a dihedral angle of 48.84 (9)° with the benzene ring belonging to the methyl­benzene­sulfonamide moiety. In the crystal, mol­ecules are ­connected through N—H⋯N hydrogen bonds and weak C—H⋯O contacts, forming a two-dimensional network parallel to (001). PMID:24427093

Facile N-Arylation of Amines and Sulfonamides and O-Arylation of Phenols and Arenecarboxylic Acids

PubMed Central

Liu, Zhijian; Larock, Richard C.

2008-01-01

An efficient, transition-metal free procedure for the N-arylation of amines, sulfonamides and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups. PMID:16599619

ipso-Hydroxylation and Subsequent Fragmentation: a Novel Microbial Strategy To Eliminate Sulfonamide Antibiotics

PubMed Central

Ricken, Benjamin; Cichocka, Danuta; Parisi, Martina; Lenz, Markus; Wyss, Dominik; Martínez-Lavanchy, Paula M.; Müller, Jochen A.; Shahgaldian, Patrick; Tulli, Ludovico G.; Kohler, Hans-Peter E.; Kolvenbach, Boris A.

2013-01-01

Sulfonamide antibiotics have a wide application range in human and veterinary medicine. Because they tend to persist in the environment, they pose potential problems with regard to the propagation of antibiotic resistance. Here, we identified metabolites formed during the degradation of sulfamethoxazole and other sulfonamides in Microbacterium sp. strain BR1. Our experiments showed that the degradation proceeded along an unusual pathway initiated by ipso-hydroxylation with subsequent fragmentation of the parent compound. The NADH-dependent hydroxylation of the carbon atom attached to the sulfonyl group resulted in the release of sulfite, 3-amino-5-methylisoxazole, and benzoquinone-imine. The latter was concomitantly transformed to 4-aminophenol. Sulfadiazine, sulfamethizole, sulfamethazine, sulfadimethoxine, 4-amino-N-phenylbenzenesulfonamide, and N-(4-aminophenyl)sulfonylcarbamic acid methyl ester (asulam) were transformed accordingly. Therefore, ipso-hydroxylation with subsequent fragmentation must be considered the underlying mechanism; this could also occur in the same or in a similar way in other studies, where biotransformation of sulfonamides bearing an amino group in the para-position to the sulfonyl substituent was observed to yield products corresponding to the stable metabolites observed by us. PMID:23835177

Rapid trace level determination of sulfonamide residues in honey with online extraction using short C-18 column by high-performance liquid chromatography with fluorescence detection.

PubMed

Sajid, Muhammad; Na, Na; Safdar, Muhammad; Lu, Xin; Ma, Lin; He, Lan; Ouyang, Jin

2013-11-01

A sensitive and inexpensive quantification method with online extraction using a short C-18 column for sulfonamide residues in honey by high performance liquid chromatography with fluorescence detector was developed and validated. In sample preparation, acid hydrolysis was used to break the N-glycoside bond between the honey sugar and sulfonamide drugs and derivatization of sulfonamide residues with fluorescamine was conducted at pH 3.5 using a citrate buffer (0.5M) in the honey matrix. The chromatography was carried out on Zorbax Extended C-18 (250mm×4.6mm; 5μm) column, using a mixture of acetonitrile and an acetate buffer (pH 4.50, 20mM) as a mobile phase. A Zorbax Extended C-18 (12mm×4.6mm; 5μm) column was used for online extraction of fifteen sulfonamide residues from honey sample with the help of a two position valve. The limit of quantification of sulfonamide residues in honey was less than 3ngg(-1), and the percentage recovery of study compounds in spiked honey sample was from 80% for sulfacetamide to 100% of sulfachloropyridazine. The developed method has excellent linearity for all studied sulfonamides with a correlation coefficient 0.993. Copyright © 2013 Elsevier B.V. All rights reserved.

Sorption and transport of five sulfonamide antibiotics in agricultural soil and soil-manure systems.

PubMed

Wang, Na; Guo, Xinyan; Xu, Jing; Hao, Lijun; Kong, Deyang; Gao, Shixiang

2015-01-01

Animal manure application is a main spreading route of veterinary antibiotics in soil and groundwater. The sorption and leaching behavior of five commonly used sulfonamides in five typical soil and soil/manure mixtures from China were investigated in this study. Results showed that the empirical Freundlich equation fits well the sorption behavior of selected sulfonamides (r(2) was between 0.803 and 0.999, 1/n was between 0.68 and 1.44), and pH and soil organic carbon (OC) were the key impact factors to sorption and leaching. Addition of manure was found to increase the Kd values of sulfonamides in five different soils, following the rules that the more polar substances, the more increased extent of sorption after manure amendment (5.87 times for sulfadiazine with Log Kow = -0.09, and 2.49 times for sulfamethoxazole with Log Kow = 0.89). When the simulated rainfall amount reached 300 mL (180 mm), sulfonamides have high migration potential to the groundwater, especially in the soil with low OC and high pH. However, manure amendment increased the sorption capacity of sulfonamides in the top layer, thus it might play a role in decreasing the mobility of sulfonamides in soils. The systematic study would be more significant to assess the ecological risks and suggest considering the influence of manure amendment for the environmental fate of antibiotics.

40 CFR 721.10595 - Octadecen-1-aminium, N-ethyl-N,N-dimethy-, ethyl sulfate (1:1).

Code of Federal Regulations, 2013 CFR

2013-07-01

...-dimethy-, ethyl sulfate (1:1). 721.10595 Section 721.10595 Protection of Environment ENVIRONMENTAL...-, ethyl sulfate (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as octadecen-1-aminium, N-ethyl-N,N-dimethy-, ethyl sulfate (1:1) (PMN P-11...

40 CFR 721.10595 - Octadecen-1-aminium, N-ethyl-N,N-dimethy-, ethyl sulfate (1:1).

Code of Federal Regulations, 2014 CFR

2014-07-01

...-dimethy-, ethyl sulfate (1:1). 721.10595 Section 721.10595 Protection of Environment ENVIRONMENTAL...-, ethyl sulfate (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as octadecen-1-aminium, N-ethyl-N,N-dimethy-, ethyl sulfate (1:1) (PMN P-11...

Sorption and biodegradation of sulfonamide antibiotics by activated sludge: experimental assessment using batch data obtained under aerobic conditions.

PubMed

Yang, Sheng-Fu; Lin, Cheng-Fang; Lin, Angela Yu-Chen; Hong, Pui-Kwan Andy

2011-05-01

This study investigated the adsorption, desorption, and biodegradation characteristics of sulfonamide antibiotics in the presence of activated sludge with and without being subjected to NaN(3) biocide. Batch experiments were conducted and the relative contributions of adsorption and biodegradation to the observed removal of sulfonamide antibiotics were determined. Three sulfonamide antibiotics including sulfamethoxazole (SMX), sulfadimethoxine (SDM), and sulfamonomethoxine (SMM), which had been detected in the influent and the activated sludge of wastewater treatment plants (WWTP) in Taiwan, were selected for this study. Experimental results showed that the antibiotic compounds were removed via sorption and biodegradation by the activated sludge, though biodegradation was inhibited in the first 12 h possibly due to competitive inhibition of xenobiotic oxidation by readily biodegradable substances. The affinity of sulfonamides to sterilized sludge was in the order of SDM > SMM > SMX. The sulfonamides existed predominantly as anions at the study pH of 6.8, which resulted in a low level of adsorption to the activated sludge. The adsorption/desorption isotherms were of a linear form, as well described by the Freundlich isotherm with the n value approximating unity. The linear distribution coefficients (K(d)) were determined from batch equilibrium experiments with values of 28.6 ± 1.9, 55.7 ± 2.2, and 110.0 ± 4.6 mL/g for SMX, SMM, and SDM, respectively. SMX, SMM, and SDM desorb reversibly from the activated sludge leaving behind on the solids 0.9%, 1.6%, and 5.2% of the original sorption dose of 100 μg/L. The sorbed antibiotics can be introduced into the environment if no further treatments were employed to remove them from the biomass. Copyright © 2011 Elsevier Ltd. All rights reserved.

Synthesis, characterization and biological screening of sulfonamides derived form 2-phenylethylamine.

PubMed

Rehman, Aziz-ur; Afroz, Sumbel; Abbasi, Muhammad Athar; Tanveer, Wajeeha; Khan, Khalid Mohammed; Ashraf, Muhammad; Ahmad, Irshad; Afzal, Iftikhar; Ambreen, Nida

2012-10-01

In the present study, a series of N-substituted derivatives of 2-phenylethylamine has been synthesized. The reaction of 2-phenylethylamine (1) with benzene sulfonyl chloride (2) yielded N-(2-phenylethyl) benzenesulfonamide (3), which further on treatment with alkyl/acyl halides (4a-i) in the presence of sodium hydride furnished into N-substituted sulfonamides (5a-i). These derivatives were characterized by IR, (1)H-NMR and EI-MS and then screened against acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase enzyme (LOX) and were found to be potent inhibitors of butyryl cholinesterase only.

N-(1-Allyl-1H-indazol-5-yl)-4-methyl­benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Abderrafia, Hafid; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

The asymmetric unit of the title compound, C17H17N3O2S, contains two independent mol­ecules linked by an N—H⋯O hydrogen bond. The mol­ecules show different conformations. In the first mol­ecule, the fused five- and six-membered ring system is almost perpendicular to the plane through the atoms forming the allyl group, as indicated by the dihedral angle of 85.1 (4)°. The dihedral angle with the methyl­benzene­sulfonamide group is 78.8 (1)°. On the other hand, in the second mol­ecule, the dihedral angles between the indazole plane and the allyl and methyl­benzene­sulfonamide groups are 80.3 (3) and 41.5 (1)°, respectively. In the crystal, mol­ecules are further linked by N—H⋯N and C—H⋯O hydrogen bonds, forming a three-dimensional network. PMID:24454264

Development of an UPLC-MS/MS Sulfonamide Multi-residue Method and It's Application to Water, Manure Slurry, and Soils from Swine Rearing Facilities

USDA-ARS?s Scientific Manuscript database

An analytical method was developed using ultra performance liquid chromatography-triple quadrupole-tandem mass spectrophotometry (UPLC-TQ-MS/MS) to simultaneously analyze 14 sulfonamides (SA) in six minutes. The instrumental detection limit based on signal-to-noise ratio (S/N) > 3, was below 1 pg/µL...

Synthesis and biochemical evaluation of triazole/tetrazole-containing sulfonamides against thrombin and related serine proteases

PubMed Central

Siles, Rogelio; Kawasaki, Yuko; Ross, Patrick; Freire, Ernesto

2011-01-01

A small library of 25 triazole/tetrazole-based sulfonamides have been synthesized and further evaluated for their inhibitory activity against thrombin, trypsin, tryptase and chymase. In general, the triazole-based sulfonamides inhibited thrombin more efficiently than the tetrazole counterparts. Particularly, compound 26 showed strong thrombin inhibition (Ki =880 nM) and significant selectivity against other human related serine proteases like trypsin (Ki =729 µM). Thrombin binding affinity of the same compound was determined by ITC and demonstrated that the binding of this new triazole-based scaffold is enthalpically driven, making it a good candidate for further development. PMID:21807511

Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors.

PubMed

Akocak, Suleyman; Lolak, Nabih; Nocentini, Alessio; Karakoc, Gulcin; Tufan, Anzel; Supuran, Claudiu T

2017-06-15

A series of sixteen novel aromatic and heterocyclic bis-sulfonamide Schiff bases were prepared by conjugation of well known aromatic and heterocyclic aminosulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitor pharmacophores with aromatic and heterocyclic bis-aldehydes. The obtained bis-sulfonamide Schiff bases were investigated as inhibitors of four selected human (h) CA isoforms, hCA I, hCA II, hCA VII and hCA IX. Most of the newly synthesized compounds showed a good inhibitory profile against isoforms hCA II and hCA IX, also showing moderate selectivity against hCA I and VII. Several efficient lead compounds were identified among this bis-sulfonamide Schiff bases with low nanomolar to sub-nanomolar activity against hCA II (K i s ranging between 0.4 and 861.1nM) and IX (K i s between 0.5 and 933.6nM). Since hCA II and hCA IX are important drug targets (antiglaucoma and anti-tumor agents), these isoform-selective inhibitors may be considered of interest for various biomedical applications. Copyright © 2017 Elsevier Ltd. All rights reserved.

Perfluoroalkylated substances in the global tropical and subtropical surface oceans.

PubMed

González-Gaya, Belén; Dachs, Jordi; Roscales, Jose L; Caballero, Gemma; Jiménez, Begoña

2014-11-18

In this study, perfluoroalkylated substances (PFASs) were analyzed in 92 surface seawater samples taken during the Malaspina 2010 expedition which covered all the tropical and subtropical Atlantic, Pacific and Indian oceans. Nine ionic PFASs including C6-C10 perfluoroalkyl carboxylic acids (PFCAs), C4 and C6-C8 perfluoroalkyl sulfonic acids (PFSAs) and two neutral precursors perfluoroalkyl sulfonamides (PFASAs), were identified and quantified. The Atlantic Ocean presented the broader range in concentrations of total PFASs (131-10900 pg/L, median 645 pg/L, n = 45) compared to the other oceanic basins, probably due to a better spatial coverage. Total concentrations in the Pacific ranged from 344 to 2500 pg/L (median = 527 pg/L, n = 27) and in the Indian Ocean from 176 to 1976 pg/L (median = 329, n = 18). Perfluorooctanesulfonic acid (PFOS) was the most abundant compound, accounting for 33% of the total PFASs globally, followed by perfluorodecanoic acid (PFDA, 22%) and perfluorohexanoic acid (PFHxA, 12%), being the rest of the individual congeners under 10% of total PFASs, even for perfluorooctane carboxylic acid (PFOA, 6%). PFASAs accounted for less than 1% of the total PFASs concentration. This study reports the ubiquitous occurrence of PFCAs, PFSAs, and PFASAs in the global ocean, being the first attempt, to our knowledge, to show a comprehensive assessment in surface water samples collected in a single oceanic expedition covering tropical and subtropical oceans. The potential factors affecting their distribution patterns were assessed including the distance to coastal regions, oceanic subtropical gyres, currents and biogeochemical processes. Field evidence of biogeochemical controls on the occurrence of PFASs was tentatively assessed considering environmental variables (solar radiation, temperature, chlorophyll a concentrations among others), and these showed significant correlations with some PFASs, but explaining small to moderate percentages of variability. This suggests that a number of physical and biogeochemical processes collectively drive the oceanic occurrence and fate of PFASs in a complex manner.

Synthesis and biological evaluation of novel quinazoline-sulfonamides as anti-cancer agents.

PubMed

Poudapally, Suresh; Battu, Shankar; Velatooru, Loka Reddy; Bethu, Murali Satyanarayana; Janapala, Venkateswara Rao; Sharma, Somesh; Sen, Subhabrata; Pottabathini, Narender; Iska, Vijaya Bhaskara Reddy; Katangoor, Vidya

2017-05-01

A robust economic approach to N-(quinazoline-4-yl)sulfonamides was developed and synthesized different aryl, hetero aryl, alkyl and cyclopropyl sulfonamides in excellent yields. All the compounds were evaluated for cytotoxic affinity to SKOV3, DU145, THP1, U937, and COLO205 cell lines. Interesting to find that the bulkiness of substituent at C-2 position of quinazoline forces the molecule to flip around in order to bind in the active site, when compared to the binding preference of previously known quinazoline compounds. Among the 21 compounds synthesized 2b, 2d, 2e, 2h, 2i, 3c, 3d, 3f, 3g and 3h found to be active on all the cell lines tested with IC 50 values <10µg/mL. Performed docking simulations to understand the binding preference of various C-2 substituted quinazoline sulfonamides. Copyright © 2017 Elsevier Ltd. All rights reserved.

Sulfonamide inhibition studies of the η-class carbonic anhydrase from the malaria pathogen Plasmodium falciparum.

PubMed

Vullo, Daniela; Del Prete, Sonia; Fisher, Gillian M; Andrews, Katherine T; Poulsen, Sally-Ann; Capasso, Clemente; Supuran, Claudiu T

2015-02-01

The η-carbonic anhydrases (CAs, EC 4.2.1.1) were recently discovered as the sixth genetic class of this metalloenzyme superfamily, and are so far known only in protozoa, including various Plasmodium species, the causative agents of malaria. We report here an inhibition study of the η-CA from Plasmodium falciparum (PfCA) against a panel of sulfonamides and one sulfamate compound, some of which are clinically used. The strongest inhibitors identified were ethoxzolamide and sulthiame, with KIs of 131-132 nM, followed by acetazolamide, methazolamide and hydrochlorothiazide (KIs of 153-198 nM). Brinzolamide, topiramate, zonisamide, indisulam, valdecoxib and celecoxib also showed significant inhibitory action against PfCA, with KIs ranging from 217 to 308 nM. An interesting observation was that the more efficient PfCA inhibitors are representative of several scaffolds and chemical classes, including benzene sulfonamides, monocyclic/bicyclic heterocyclic sulfonamides and compounds with a more complex scaffold (i.e., the sugar sulfamate derivative, topiramate, and the coxibs, celecoxib and valdecoxib). A comprehensive inhibition study of small molecules for η-CAs is needed as a first step towards assessing PfCA as a druggable target. The present work identifies the first known η-CA inhibitors and provides a platform for the development of next generation novel PfCA inhibitors. Copyright © 2014 Elsevier Ltd. All rights reserved.

N-(1H-Indazol-5-yl)-4-meth­oxy­benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

In the title compound, C14H13N3O3S, the fused ring system is almost planar, the largest deviation from the mean plane being 0.023 (2) Å, and makes a dihedral angle of 47.92 (10)° with the benzene ring of the benzene­sulfonamide moiety. In the crystal, mol­ecules are connected through N—H⋯O hydrogen bonds and weak C—H⋯O contacts, forming a two-dimensional network which is parallel to (010). PMID:24454128

Determination of perfluorinated compounds in fish fillet homogenates: method validation and application to fillet homogenates from the Mississippi River.

PubMed

Malinsky, Michelle Duval; Jacoby, Cliffton B; Reagen, William K

2011-01-10

We report herein a simple protein precipitation extraction-liquid chromatography tandem mass spectrometry (LC/MS/MS) method, validation, and application for the analysis of perfluorinated carboxylic acids (C7-C12), perfluorinated sulfonic acids (C4, C6, and C8), and perfluorooctane sulfonamide (FOSA) in fish fillet tissue. The method combines a rapid homogenization and protein precipitation tissue extraction procedure using stable-isotope internal standard (IS) calibration. Method validation in bluegill (Lepomis macrochirus) fillet tissue evaluated the following: (1) method accuracy and precision in both extracted matrix-matched calibration and solvent (unextracted) calibration, (2) quantitation of mixed branched and linear isomers of perfluorooctanoate (PFOA) and perfluorooctanesulfonate (PFOS) with linear isomer calibration, (3) quantitation of low level (ppb) perfluorinated compounds (PFCs) in the presence of high level (ppm) PFOS, and (4) specificity from matrix interferences. Both calibration techniques produced method accuracy of at least 100±13% with a precision (%RSD) ≤18% for all target analytes. Method accuracy and precision results for fillet samples from nine different fish species taken from the Mississippi River in 2008 and 2009 are also presented. Copyright © 2010 Elsevier B.V. All rights reserved.

MATERNAL AND DEVELOPMENTAL TOXICITY OF PERFLUOROOCTANE SULFONATE IN THE RAT

EPA Science Inventory

MATERNAL AND DEVELOPMENTAL TOXICITY OF PERFLUOROOCTANE SULFONATE IN THE RAT.
C. Lau and J.M. Rogers, Reproductive Toxicology Division, NHEERL, ORD, USEPA, Research Triangle Park, NC, USA

Perfluorooctane sulfonate (PFOS), an environmentally persistent compound used ...

Comparison of PFASs contamination in the freshwater and terrestrial environments by analysis of eggs from osprey (Pandion haliaetus), tawny owl (Strix aluco), and common kestrel (Falco tinnunculus).

PubMed

Eriksson, Ulrika; Roos, Anna; Lind, Ylva; Hope, Kjell; Ekblad, Alf; Kärrman, Anna

2016-08-01

The level of PFAS (per- and polyfluorinated alkyl substances) contamination in freshwater and terrestrial Swedish environments in 2013/2014 was assessed by analyzing a range of perfluorinated alkyl acids, fluorotelomer acids, sulfonamides, sulfonamidoethanols and polyfluoralkyl phosphate diesters (diPAPs) in predator bird eggs. Stable isotopes ((13)C and (15)N) were analyzed to elucidate the dietary source. The tawny owl (Strix aluco, n=10) and common kestrel (Falco tinnunculus, n=40), two terrestrial species, and the osprey (Pandion haliaetus, n=30), a freshwater specie were included. In addition, a temporal trend (1997-2001, 2008-2009, 2013) in osprey was studied as well. The PFAS profile was dominated by perfluorooctane sulfonic acid (PFOS) in eggs from osprey and tawny owl, while for common kestrel perfluorinated carboxylic acids (∑PFCA) exceeded the level of PFOS. PFOS concentration in osprey eggs remained at the same level between 1997 and 2001 and 2013. For the long-chained PFCAs, there were a significant increase in concentrations in osprey eggs between 1997 and 2001 and 2008-2009. The levels of PFOS and PFCAs were about 10 and five times higher, respectively, in osprey compared to tawny owl and common kestrel. Evidence of direct exposure from PFCA precursor compounds to birds in both freshwater and terrestrial environment was observed. Low levels of diPAPs were detected in a few samples of osprey (<0.02-2.4ng/g) and common kestrel (<0.02-0.16ng/g) eggs, and 6:2 FTSA was detected in a majority of the osprey eggs (<6.3-52ng/g). One saturated telomer acid (7:3 FTCA), which is a transformation marker from precursor exposure, was detected in all species (<0.24-2.7ng/g). The (15)N data showed higher levels in osprey eggs compared to tawny owl and common kestrel, indicating that they feed on a 2-3 times higher trophic level. We conclude that ospreys are continuously exposed to PFAS at levels where adverse toxic effects have been observed in birds. Copyright © 2016 Elsevier Inc. All rights reserved.

Sulfonamide inhibition studies of the β-carbonic anhydrase from the newly discovered bacterium Enterobacter sp. B13.

PubMed

Eminoğlu, Ayşenur; Vullo, Daniela; Aşık, Aycan; Çolak, Dilşat Nigar; Çanakçı, Sabriye; Beldüz, Ali Osman; Supuran, Claudiu T

2016-04-01

The genome of the newly identified bacterium Enterobacter sp. B13 encodes for a β-class carbonic anhydrases (CAs, EC 4.2.1.1), EspCA. This enzyme was recently cloned, and characterized kinetically by this group (J. Enzyme Inhib. Med. Chem. 2016, 31). Here we report an inhibition study with sulfonamides and sulfamates of this enzyme. The best EspCA inhibitors were some sulfanylated sulfonamides with elongated molecules, metanilamide, 4-aminoalkyl-benzenesulfonamides, acetazolamide, and deacetylated methazolamide (KIs in the range of 58.7-96.5nM). Clinically used agents such as methazolamide, ethoxzolamide, dorzolamide, brinzolamide, benzolamide, zonisamide, sulthiame, sulpiride, topiramate and valdecoxib were slightly less effective inhibitors (KIs in the range of 103-138nM). Saccharin, celecoxib, dichlorophenamide and many simple benzenesulfonamides were even less effective as EspCA inhibitors, with KIs in the range of 384-938nM. Identification of effective inhibitors of this bacterial enzyme may lead to pharmacological tools useful for understanding the physiological role(s) of the β-class CAs in bacterial pathogenicity/virulence. Copyright © 2016 Elsevier Ltd. All rights reserved.

Carbonic anhydrase inhibitors. Inhibition of human cytosolic isoforms I and II with (reduced) Schiff's bases incorporating sulfonamide, carboxylate and carboxymethyl moieties.

PubMed

Nasr, Gihane; Cristian, Alina; Barboiu, Mihail; Vullo, Daniella; Winum, Jean-Yves; Supuran, Claudiu T

2014-05-15

A library of Schiff bases was synthesized by condensation of aromatic amines incorporating sulfonamide, carboxylic acid or carboxymethyl functionalities as Zn(2+)-binding groups, with aromatic aldehydes incorporating tert-butyl, hydroxy and/or methoxy groups. The corresponding amines were thereafter obtained by reduction of the imines. These compounds were assayed for the inhibition of two cytosolic human carbonic anhydrase (hCA, EC 4.2.1.1) isoenzymes, hCA I and II. The Ki values of the Schiff bases were in the range of 7.0-21,400nM against hCA II and of 52-8600nM against hCA I, respectively. The corresponding amines showed Ki values in the range of 8.6nM-5.3μM against hCA II, and of 18.7-251nM against hCA I, respectively. Unlike the imines, the reduced Schiff bases are stable to hydrolysis and several low-nanomolar inhibitors were detected, most of them incorporating sulfonamide groups. Some carboxylates also showed interesting CA inhibitory properties. Such hydrosoluble derivatives may show pharmacologic applications. Copyright © 2014 Elsevier Ltd. All rights reserved.

Sulfonyl chlorides as an efficient tool for the postsynthetic modification of Cr-MIL-101-SO3H and CAU-1-NH2.

PubMed

Klinkebiel, Arne; Reimer, Nele; Lammert, Martin; Stock, Norbert; Lüning, Ulrich

2014-08-25

Postsynthetic modification can be used to introduce sulfonamide functionalities into MOF frameworks. Using sulfonyl chlorides as reactive intermediates, Cr-MIL-SO3H and CAU-1-NH2 have been further modified to give hitherto unknown functionalized MOFs in which a sulfonamide group is bound to the framework either by its N or its S atom.

Synthesis, characterization, and antifungal activity of novel (Z)-N-(2-cyano-3-phenylprop-2-en-1-yl)-alkyl/aryl-sulfonamides derived from a Morita-Baylis-Hillman adduct

NASA Astrophysics Data System (ADS)

Tavares, Eder C.; Rubinger, Mayura M. M.; Zacchi, Carlos H. C.; Silva, Simone A.; Oliveira, Marcelo R. L.; Guilardi, Silvana; Alcântara, Antônio F. de C.; Piló-Veloso, Dorila; Zambolim, Laércio

2014-06-01

A series of allyl sulfonamides prepared from the reaction of the Morita-Baylis-Hillman adduct 2-[hydroxy(phenyl)methyl]acrylonitrile with primary sulfonamides (RSO2NH2), where R = C6H5 (1), 4-Fsbnd C6H4 (2), 4-Clsbnd C6H4 (3), 4-Brsbnd C6H4 (4), 4-NO2sbnd C6H4 (5), CH3 (6), CH3CH2 (7), CH3(CH2)3 (8), and CH3(CH2)7 (9), were characterized by IR, 1H and 13C NMR spectroscopies, mass spectrometry and elemental analyses. BLYP/6-31G* calculations suggested stereoselective reactions, resulting in the exclusive formation of the thermodynamically more stable Z-products. The Z-configuration of the products was confirmed by NOE difference spectroscopy and single crystal X-ray diffraction measurements. The allyl sulfonamides were active against Colletotrichum gloeosporioides, an important agent of anthracnose in plants.

Exposure to perfluorooctane sulfonate during pregnancy in rat and mouse. I: maternal and prenatal evaluations

EPA Science Inventory

Abstract: The maternal and developmental toxicities of perfluorooctane sulfonate (PFOS, C8F17SO3-) were evaluated in the rat and mouse. PFOS is an environmentally persistent compound used as a surfactant and occurs as a degradation product of both perfluorooctane sulfonyl fluorid...

Design, synthesis, characterization and computational docking studies of novel sulfonamide derivatives.

PubMed

Saleem, Hira; Maryam, Arooma; Bokhari, Saleem Ahmed; Ashiq, Ayesha; Rauf, Sadaf Abdul; Khalid, Rana Rehan; Qureshi, Fahim Ashraf; Siddiqi, Abdul Rauf

2018-01-01

This study reports three novel sulfonamide derivatives 4-Chloro-N-[(4-methylphenyl) sulphonyl]-N-propyl benzamide ( 1A ), N-(2-hydroxyphenyl)-4-methyl benzene sulfonamide ( 1B ) and 4-methyl-N-(2-nitrophenyl) benzene sulfonamide ( 1C ). The compounds were synthesised from starting material 4-methylbenzenesulfonyl chloride and their structure was studied through 1 H-NMR and 13 C-NMR spectra. Computational docking was performed to estimate their binding energy against bacterial p -amino benzoic acid (PABA) receptor, the dihydropteroate synthase (DHPS). The derivatives were tested in vitro for their antimicrobial activity against Gram+ and Gram- bacteria including E. coli, B. subtilis, B. licheniformis and B. linen. 1A was found active only against B. linen ; 1B was effective against E. coli, B. subtilis and B. linen whereas 1C showed activity against E. coli, B. licheniformis and B. linen . 1C showed maximum activity with minimum inhibitory concentration (MIC) of 50, 100 and 150 µg/mL against E. coli, B. licheniformis and B. linen respectively. 1C exhibited maximum affinity to DHPS with binding free energy of -8.1 kcal/mol. It enriched in the top 0.5 % of a library of 7663 compounds, ranked in order of their binding affinity against DHPS. 1C was followed by 1B which showed a moderate to low level MIC of 100, 250 and 150 µg/mL against E. coli, B. subtilis and B. linen respectively, whereas 1A showed a moderate level MIC of 100 µg/mL but only against B. linen . These derivatives may thus serve as potential anti-bacterial alternatives against resistant pathogens.

Poly (N-ethyl aniline)/Ag Nanocomposite as Humidity Sensor

NASA Astrophysics Data System (ADS)

Pande, Nishigandh S.; Jaspal, Dipika; Ambekar, Jalindar

Poly (N-ethyl aniline)/Ag organic-inorganic composite has been synthesized by a single step in situ chemical oxidative polymerization method. The synthesis of Poly (N-ethyl aniline)/Ag nanocomposite has been confirmed by X-ray diffraction (XRD), Ultraviolet-Vis Spectroscopy (UV-visible), Fourier transform infrared analysis (FTIR) and FE-SEM investigations. XRD spectral study exhibited major diffraction in the range 20-80∘ (2θ) and indicated the semicrystalline nature of poly (N-ethyl aniline)/Ag nanocomposite. Characteristic peaks in UV-visible and FTIR spectra of poly (N-ethyl aniline) switched to higher wave numbers in poly (N-ethyl aniline)/Ag nanocomposite. Peaks at 1789cm-1, 1595cm-1, 667cm-1 and 501cm-1 in FTIR spectrum confirmed the formation of poly (N-ethyl aniline)/Ag nanocomposite. FE-SEM photographs reported agglomerated granular particulate nature of poly (N-ethyl aniline)/Ag nanocomposite. Synthesized poly (N-ethyl aniline)/Ag nanocomposite exhibited a high response to humidity, good reproducibility and stability at room temperature. An appreciable response was shown in the presence of 40% humid atmosphere for up to successive four cycles. Composite sensitivity has been found to increase with the increasing concentration of humidity, at room temperature.

Synthesis of Chromone, Quinolone, and Benzoxazinone Sulfonamide Nucleosides as Conformationally Constrained Inhibitors of Adenylating Enzymes Required for Siderophore Biosynthesis

PubMed Central

Engelhart, Curtis A.; Aldrich, Courtney C.

2013-01-01

MbtA catalyzes the first committed step of mycobactin biosynthesis in Mycobacterium tuberculosis (Mtb) and is responsible for the incorporation of salicylic acid into the mycobactin siderophores. 5′-O-[N-(Salicyl)sulfamoyl]adenosine (Sal-AMS) is an extremely potent nucleoside inhibitor of MbtA that possesses excellent activity against whole-cell Mtb, but suffers from poor bioavailability. In an effort to improve the bioavailability, we have designed four conformationally constrained analogues of Sal-AMS that remove two rotatable bonds and the ionized sulfamate group based on computational and structural studies. Herein we describe the synthesis, biochemical, and microbiological evaluation of chromone-, quinolone-, and benzoxazinone-3-sulfonamide derivatives of Sal-AMS. We developed new chemistry to assemble these three heterocycles from common β-ketosulfonamide intermediates. The synthesis of the chromone- and quinolone-3-sulfonamide intermediates features formylation of a β-ketosulfonamide employing dimethylformamide dimethyl acetal to afford an enaminone that can react intramolecularly with a phenol or intermolecularly with a primary amine via addition-elimination reaction(s). The benzoxazinone-3-sulfonamide was prepared by nitrosation of a β-ketosulfonamide followed by intramolecular nucleophilic aromatic substitution. Mitsunobu coupling of these bicyclic sulfonamides with a protected adenosine derivative followed by global deprotection provides a concise synthesis of the respective inhibitors. PMID:23805993

40 CFR 721.8100 - Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy...

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. 721.8100...-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. (a) Chemical substances and significant new use subject to...

40 CFR 721.8100 - Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy...

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. 721.8100...-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. (a) Chemical substances and significant new use subject to...

40 CFR 721.8100 - Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy...

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. 721.8100...-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. (a) Chemical substances and significant new use subject to...

40 CFR 721.8100 - Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy...

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. 721.8100...-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. (a) Chemical substances and significant new use subject to...

40 CFR 721.8100 - Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy...

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Potassium N,N-bis (hydroxy-ethyl) cocoamine oxide phosphate, and potassium N,N-bis (hy-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. 721.8100...-droxy-ethyl) tal-lo-wa-mine oxide phos-phate. (a) Chemical substances and significant new use subject to...

Thermally Stable Perfluorinated Polymers.

DTIC Science & Technology

perfluoropropane ; 1,8-bis(5-tetrazolyl) perfluorooctane ; bitetrazole; perfluorosebacoyl chloride; 5,5’-bis(n- perfluorobutyryl ) chloride)-2,2’-bi-1,3,4-oxadiazole...Studies of the poly( perfluoroalkylene -1,3,4-oxadiazole) systems have been continued using the following monomers: 1,3-bis(5-tetrazolys

Emerging investigator series: a 14-year depositional ice record of perfluoroalkyl substances in the High Arctic.

PubMed

MacInnis, John J; French, Katherine; Muir, Derek C G; Spencer, Christine; Criscitiello, Alison; De Silva, Amila O; Young, Cora J

2017-01-25

To improve understanding of long-range transport of perfluoroalkyl substances to the High Arctic, samples were collected from a snow pit on the Devon Ice Cap in spring 2008. Snow was analyzed for perfluoroalkyl acids (PFAAs), including perfluoroalkyl carboxylic acids (PFCAs) and perfluoroalkyl sulfonic acids (PFSAs), as well as perfluorooctane sulfonamide (FOSA). PFAAs were detected in all samples dated from 1993 to 2007. PFAA fluxes ranged from <1 to hundreds of ng per m 2 per year. Flux ratios of even-odd PFCA homologues were mostly between 0.5 and 2, corresponding to molar ratios expected from atmospheric oxidation of fluorotelomer compounds. Concentrations of perfluorobutanoic acid (PFBA) were much higher than other PFCAs, suggesting PFBA loading on the Devon Ice Cap is influenced by additional sources, such as the oxidation of heat transfer fluids. All PFCA fluxes increased with time, while PFSA fluxes generally decreased with time. No correlations were observed between PFAAs and the marine aerosol tracer, sodium. Perfluoro-4-ethylcyclohexanesulfonate (PFECHS) was detected for the first time in an atmospherically - derived sample, and its presence may be attributed to aircraft hydraulic system leakage. Observations of PFAAs from these samples provide further evidence that atmospheric oxidation of volatile precursors is an important source of PFAAs to the Arctic environment.

PFAS profiles in three North Sea top predators: metabolic differences among species?

PubMed

Galatius, Anders; Bossi, Rossana; Sonne, Christian; Rigét, Frank Farsø; Kinze, Carl Christian; Lockyer, Christina; Teilmann, Jonas; Dietz, Rune

2013-11-01

Profiles of seven compounds of perfluoro-alkyl substances (PFASs) were compared among three species of top predators from the Danish North Sea: the white-beaked dolphin (Lagenorhynchus albirostris), the harbor porpoise (Phocoena phocoena), and the harbor seal (Phoca vitulina). The seals had higher total burdens (757.8 ng g(-1) ww) than the dolphins (439.9 ng g(-1) ww) and the porpoises (355.8 ng g(-1) ww), probably a reflection of feeding closer to the shore and thus contamination sources. The most striking difference among the species was the relative contribution of perfluorooctanesulfonamide (PFOSA) to the profiles; the seals (0.1%) had much lower levels than porpoises (8.3%) and dolphins (26.0%). In combination with the values obtained from the literature, this result indicates that Carnivora species including Pinnipedia have a much higher capacity of transforming PFOSA to perfluorooctane sulfonic acid (PFOS) than cetacean species. Another notable difference among the species was that the two smaller species (seals and porpoises) with supposedly higher metabolic rates had lower concentrations of the perfluorinated carboxylic acids, which are generally more easily excreted than perfluorinated sulfonamides. Species-specific characteristics should be recognized when PFAS contamination in marine mammals is investigated, for example, several previous studies of PFASs in cetaceans have not quantified PFOSA.

Atmospheric concentrations and gas/particle partitioning of neutral poly- and perfluoroalkyl substances in northern German coast

NASA Astrophysics Data System (ADS)

Wang, Zhen; Xie, Zhiyong; Möller, Axel; Mi, Wenying; Wolschke, Hendrik; Ebinghaus, Ralf

2014-10-01

Total 58 high volume air samples were collected in Büsum, Germany, from August 2011 to October 2012 to investigate air concentrations of 12 per- and polyfluoroalkyl substances (PFASs) and their gas/particle partitioning. The total concentration (vapor plus particle phases) of the 12 PFASs (ΣPFASs) ranged from 8.6 to 155 pg/m3 (mean: 41 pg/m3) while fluorotelomer alcohols 8:2 (8:2 FTOH) dominated all samples accounting for 61.9% of ΣPFASs and the next most species were 10:2 FTOH (12.7%). Air mass back trajectory analysis showed that atmospheric PFASs in most samples were from long range atmospheric transport processes and had higher ratios of 8:2 to 6:2 FTOH compared to the data obtained from urban/industrial sources. Small portion of particle PFASs in the atmosphere was observed and the average percent to ΣPFASs was 2.0%. The particle-associated fractions of different PFASs decreased from perfluorooctane sulfonamidoethanols (FOSEs) (15.5%) to fluorotelomer acrylates (FTAs) (7.6%) to perfluorooctane sulfonamides (FOSAs) (3.1%) and FTOHs (1.8%), indicating the functional group obviously influenced their gas/particle partitioning. For neutral compounds with acid dissociation constant (pKa) > 7.0 (i.e., FTOHs, FOSEs and FOSAs), a significant log-linear relationship was observed between their gas/particle partition coefficients (KSP) and vapor pressures (pºL), suggesting the gas/particle partitioning of neutral PFASs agreed with the classical logKSP-logpºL relation. Due to the pKa values of 6:2 and 8:2 FTA below the typical environmental pH conditions, they mainly exist as ionic form in aerosols, and the corrected logKSP (neutral form) were considerably lower than those of FTOHs, FOSEs and FOSAs with similar vapor pressures. Considering the strong partitioning potential to aqueous phases for ionic PFASs at higher pH values, a need exists to develop a model taking account of the ad/absorption mechanism to the condensed phase of aerosols for ionizable PFASs (e.g., FTAs).

4-Amino-N-(3-meth­oxy­pyrazin-2-yl)benzene­sulfonamide

PubMed Central

Bruni, Bruno; Coran, Silvia A.; Bartolucci, Gianluca; Di Vaira, Massimo

2010-01-01

The overall mol­ecular geometry of the title compound, C11H12N4O3S, is bent, with a dihedral angle of 89.24 (5)° between the best planes through the two aromatic rings. Each mol­ecule behaves as a hydrogen-bond donor toward three different mol­ecules, through its amidic and the two aminic H atoms, and it behaves as a hydrogen-bond acceptor from two other mol­ecules via one of its sulfonamidic O atoms. In the crystal, mol­ecules linked by N—H⋯N and N—H⋯O hydrogen bonds form kinked layers parallel to (001), adjacent layers being connected by van der Waals inter­actions. PMID:21587634

Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas.

PubMed

Ekoue-Kovi, Kekeli; Yearick, Kimberly; Iwaniuk, Daniel P; Natarajan, Jayakumar K; Alumasa, John; de Dios, Angel C; Roepe, Paul D; Wolf, Christian

2009-01-01

We report the synthesis and in vitro antimalarial activities of more than 50 7-chloro-4-aminoquinolyl-derived sulfonamides 3-8 and 11-26, ureas 19-22, thioureas 23-26, and amides 27-54. Many of the CQ analogues prepared for this study showed submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strains of Plasmodium falciparum) and low resistance indices were obtained in most cases. Systematic variation of the side chain length and introduction of fluorinated aliphatic and aromatic termini revealed promising leads that overcome CQ resistance. In particular, sulfonamide 3 exhibiting a short side chain with a terminal dansyl moiety combined high antiplasmodial potency with a low resistance index and showed IC(50)s of 17.5 and 22.7 nM against HB3 and Dd2 parasites.

A single-nucleotide polymorphism in the canine cytochrome b5 reductase (CYB5R3) gene is associated with sulfonamide hypersensitivity and is overrepresented in Doberman Pinschers.

PubMed

Reinhart, J M; Ekena, J; Cioffi, A C; Trepanier, L A

2018-06-01

Canine sulfonamide hypersensitivity (HS) has been associated with a variant in the cytochrome b 5 reductase gene (CYB5R3 729A>G), which encodes a drug-detoxifying enzyme. Study objectives were to determine variant allele frequency in Doberman Pinschers (DOBE), a breed which may be predisposed to sulfonamide HS, and to characterize the effects of CYB5R3 729G on gene expression and function. CYB5R3 729A>G allele frequencies were compared between DOBE (n = 24) vs. non-Doberman (non-DOBE; n = 60) dogs. CYB5R3mRNA expression, protein expression, and reduction of sulfamethoxazole hydroxylamine were compared between banked canine liver samples of 729AA vs. GG genotype. The 729G allele was overrepresented in DOBE (1.00) vs. non-DOBE dogs (0.567, p < .0001). mRNA and protein expressions as well as cyt b 5 reductase activity were similar between livers of AA and GG genotype. All Doberman Pinschers in this study were homozygous for CYB5R3 729G, which could contribute to this breed's apparent predisposition to sulfonamide HS. However, CYB5R3 729G does not alter sulfamethoxazole detoxification capacity, so a direct role could not be demonstrated. It is possible that this marker is linked to another contributing variant. © 2018 John Wiley & Sons Ltd.

40 CFR 721.1085 - Benzenamine,4,4′-methylenebis[N-ethyl-N-methyl-.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzenamine,4,4â²-methylenebis[N-ethyl-N-methyl-. 721.1085 Section 721.1085 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1085 Benzenamine,4,4′-methylenebis[N-ethyl-N-methyl-. (a) Chemical...

40 CFR 721.1085 - Benzenamine,4,4′-methylenebis[N-ethyl-N-methyl-.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzenamine,4,4â²-methylenebis[N-ethyl-N-methyl-. 721.1085 Section 721.1085 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1085 Benzenamine,4,4′-methylenebis[N-ethyl-N-methyl-. (a) Chemical...

N-(2-methoxyphenyl) benzenesulfonamide, a novel regulator of neuronal G protein-gated inward rectifier K+ channels.

PubMed

Walsh, Kenneth B; Gay, Elaine A; Blough, Bruce E; Geurkink, David W

2017-11-15

G protein-gated inward rectifier K + (GIRK) channels are members of the super-family of proteins known as inward rectifier K + (Kir) channels and are expressed throughout the peripheral and central nervous systems. Neuronal GIRK channels are the downstream targets of a number of neuromodulators including opioids, somatostatin, dopamine and cannabinoids. Previous studies have demonstrated that the ATP-sensitive K + channel, another member of the Kir channel family, is regulated by sulfonamide drugs. Therefore, to determine if sulfonamides also modulate GIRK channels, we screened a library of arylsulfonamide compounds using a GIRK channel fluorescent assay that utilized pituitary AtT20 cells expressing GIRK channels along with the somatostatin type-2 and -5 receptors. Enhancement of the GIRK channel fluorescent signal by one compound, N-(2-methoxyphenyl) benzenesulfonamide (MPBS), was dependent on the activation of the channel by somatostatin. In whole-cell patch clamp experiments, application of MPBS both shifted the somatostatin concentration-response curve (EC 50 = 3.5nM [control] vs.1.0nM [MPBS]) for GIRK channel activation and increased the maximum GIRK current measured with 100nM somatostatin. However, GIRK channel activation was not observed when MPBS was applied to the cells in the absence of somatostatin. While the MPBS structural analog 4-fluoro-N-(2-methoxyphenyl) benzenesulfonamide also augmented the somatostatin-induced GIRK fluorescent signal, no increase in the signal was observed with the sulfonamides tolbutamide, sulfapyridine and celecoxib. In conclusion, MPBS represents a novel prototypic GPCR-dependent regulator of neuronal GIRK channels. Copyright © 2017 Elsevier B.V. All rights reserved.

N-(6-Methylpyridin-2-yl)mesitylenesulfonamide and acetic acid--a salt, a cocrystal or both?

PubMed

Pan, Fangfang; Kalf, Irmgard; Englert, Ulli

2015-08-01

In the solid obtained from N-(6-methylpyridin-2-yl)mesitylenesulfonamide and acetic acid, the constituents interact via two N-H···O hydrogen bonds. The H atom situated in one of these short contacts is disordered over two positions: one of these positions is formally associated with an adduct of the neutral sulfonamide molecule and the neutral acetic acid molecule, and corresponds to a cocrystal, while the alternative site is associated with salt formation between a protonated sulfonamide molecule and deprotonated acetic acid molecule. Site-occupancy refinements and electron densities from difference Fourier maps suggest a trend with temperature, albeit of limited significance; the cocrystal is more relevant at 100 K, whereas the intensity data collected at room temperature match the description as cocrystal and salt equally well.

Vibrational spectroscopic and quantum chemical calculations of (E)-N-Carbamimidoyl-4-((naphthalen-1-yl-methylene)amino)benzene sulfonamide.

PubMed

Chandran, Asha; Varghese, Hema Tresa; Mary, Y Sheena; Panicker, C Yohannan; Manojkumar, T K; Van Alsenoy, Christian; Rajendran, G

2012-02-15

FT-IR and FT-Raman spectra of (E)-N-Carbamimidoyl-4-((naphthalen-1-yl-methylene)amino)benzene sulfonamide were recorded and analyzed. The vibrational wavenumbers were computing at various levels of theory. The data obtained from theoretical calculations are used to assign vibrational bands obtained experimentally. The results indicate that B3LYP method is able to provide satisfactory results for predicting vibrational frequencies and structural parameters. The calculated first hyperpolarizability is comparable with reported values of similar derivatives and is an attractive object for future studies of non-linear optics. The geometrical parameters of the title compound are in agreement with that of similar derivatives. Copyright © 2011 Elsevier B.V. All rights reserved.

Spectroscopic characterization, antimicrobial activity, DFT computation and docking studies of sulfonamide Schiff bases

NASA Astrophysics Data System (ADS)

Mondal, Sudipa; Mandal, Santi M.; Mondal, Tapan Kumar; Sinha, Chittaranjan

2017-01-01

Schiff bases synthesised from the condensation of 2-(hydroxy)naphthaldehyde and sulfonamides (sufathiazole (STZ), sulfapyridine (SPY), sulfadiazine (SDZ), sulfamerazine (SMZ) and sulfaguanidine (SGN)) are characterized by different spectroscopic data (FTIR, UV-Vis, Mass, NMR) and two of them, (E)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-N-(thiazol-2-yl)benzenesulfonamide (1a) and (E)-N-(diaminomethylene)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzenesulfonamide (1e) have been confirmed by single crystal X-ray structure determination. Antimicrobial activities of the Schiff bases have been evaluated against certified and resistant Gram positive (Staphylococcus aureus, Enterococcus facelis) and Gram negative (Streptococcus pyogenes, Salmonella typhi, Shigella dysenteriae, Shigella flexneri, Klebsiella pneumonia) pathogens. Performance of Schiff base against the resistant pathogens are better than standard stain and MIC data lie 32-128 μg/ml while parent sulfonamides are effectively inactive (MIC >512 μg/ml). The DFT optimized structures of the Schiff bases have been used to accomplish molecular docking studies with DHPS (dihydropteroate synthase) protein structure (downloaded from Protein Data Bank) to establish the most preferred mode of interaction. ADMET filtration, Cytotoxicity (MTT assay) and haemolysis assay have been examined for evaluation of druglike character.

[Method for Simultaneous Determination of 11 Veterinary Antibiotics in Piggery Wastewater and Sludge and Its Application in Biological Treatment].

PubMed

Ding, Jia-li; Liu, Rui; Zheng, Wei; Yu, Wei-juan; Ye, Zhao-xia; Chen, Lu-jun; Zhang, Yong-ming

2015-10-01

In order to determine eleven commonly used veterinary antibiotics (including four tetracyclines, two sulfonamides, three quinolones and two macrolides) in piggery wastewater and activated sludge in the Yangtze River Delta region, the conditions of solid phase extraction and high performance liquid chromatography-tandem mass spectrometry were optimized. The recovery rate and relative standard deviations of the method were confirmed as 73% - 105.2%, 3.1% - 10.2% for piggery wastewater (n = 3) and 57.4% - 104.6%, 1.9% - 10.9% (n = 3) respectively for the activated sludge. Removal of antibiotics was then studied in a membrane bioreactor. The results showed that antibiotics of both tetracycline and sulfonamide species took a large portion in the wastewater, while tetracycline species were the dominant in the sludge. Tetracycline species in the wastewater were removed by 85.2%, mainly through biodegradation (51.9%) and secondly by sludge adsorption (33.2%). By comparison, sulfonamide species was removed by 95.8%, almost all through biodegradation while little by sludge adsorption. Flask tests suggested that the accumulated antibiotics in the sludge give no significant influence on the microbial removal of organics and ammonium.

40 CFR 180.601 - Cyazofamid; tolerances for residues.

Code of Federal Regulations, 2010 CFR

2010-07-01

... residues of cyazofamid, 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide, and its metabolite CCIM, 4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile, expressed as cyazofamid... established for the combined residues of cyazofamid, 4-chloro-2-cyano- N,N-dimethyl-5-(4-methylphenyl)-1H...

Molecular structure and conformations of para-methylbenzene sulfonamide and ortho-methylbenzene sulfonamide: gas electron diffraction and quantum chemical calculations study.

PubMed

Petrov, Vjacheslav M; Girichev, Georgiy V; Oberhammer, Heinz; Petrova, Valentina N; Giricheva, Nina I; Bardina, Anna V; Ivanov, Sergey N

2008-04-03

The molecular structure and conformational properties of para-methylbenzene sulfonamide (4-MBSA) and ortho-methylbenzene sulfonamide (2-MBSA) have been studied by gas electron diffraction (GED) and quantum chemical methods (B3LYP/6-311+G** and MP2/6-31G**). Quantum chemical calculations predict the existence of two conformers for 4-MBSA with the S-N bond perpendicular to the benzene plane and the NH2 group either eclipsing or staggering the S-O bonds of the SO2 group. Both conformers possess CS symmetry. The eclipsed form is predicted to be favored by DeltaE = 0.63 kcal/mol (B3LYP) or 1.00 kcal/mol (MP2). According to the calculations, the S-N bond in 2-MBSA can possess planar direction opposite the methyl group (phi(C2C1SN) = 180 degrees ) or nonplanar direction (phi(C2C1SN) approximately 60 degrees ). In both cases, the NH2 group can adopt eclipsed or staggered orientation, resulting in a total of four stable conformers. The nonplanar eclipsed conformer (C1 symmetry) and the planar eclipsed form (CS symmetry) are predicted to be favored. According to the GED analysis, the saturated vapor over solid 4-MBSA at T = 151(3) degrees C consists as mixture of the eclipsed (78(19) %) and staggered (22(19) %) forms. The saturated vapor over solid 2-MBSA at T = 157(3) degrees C consists as a mixture of the nonplanar eclipsed (69(11) %) and planar eclipsed (31(11) %) forms.

Viscosities of nonelectrolyte liquid mixtures. II. Binary mixtures of n-hexane with alkanoates and bromoalkanoates

NASA Astrophysics Data System (ADS)

Oswal, S. L.; Dave, J. P.

1992-11-01

Viscosity measurements are reported for mixtures of ethyl ethanoate, ethyl propionate, ethyl butyrate, ethyl-2-bromopropionate, ethyl-3-bromopropionate, ethyl-2-bromobutyrate, and ethyl-4-bromobutyrate with n-hexane at 303.15 K. The viscosity data have been correlated with equations of Grunberg and Nissan, of McAllister, and of Auslaender. Furthermore, excess Gibbs energies of activation ΔG * E of viscous flow have been calculated with Eyring's theory of absolute reaction rates and values of ΔG * E for the present binary mixtures have been explained in terms of the dipole-dipole interaction in alkanoates and the intramolecular Br...O interaction in bromoalkanoates.

40 CFR 721.9573 - Substituted perfluoroalkyl sulfonamide (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

... as a substituted perfluoroalkyl sulfonamide (PMN P-98-645) is subject to reporting under this section... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted perfluoroalkyl sulfonamide... Specific Chemical Substances § 721.9573 Substituted perfluoroalkyl sulfonamide (generic). (a) Chemical...

40 CFR 721.9573 - Substituted perfluoroalkyl sulfonamide (generic).

Code of Federal Regulations, 2013 CFR

2013-07-01

... as a substituted perfluoroalkyl sulfonamide (PMN P-98-645) is subject to reporting under this section... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted perfluoroalkyl sulfonamide... Specific Chemical Substances § 721.9573 Substituted perfluoroalkyl sulfonamide (generic). (a) Chemical...

40 CFR 721.9573 - Substituted perfluoroalkyl sulfonamide (generic).

Code of Federal Regulations, 2010 CFR

2010-07-01

... as a substituted perfluoroalkyl sulfonamide (PMN P-98-645) is subject to reporting under this section... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted perfluoroalkyl sulfonamide... Specific Chemical Substances § 721.9573 Substituted perfluoroalkyl sulfonamide (generic). (a) Chemical...

40 CFR 721.9573 - Substituted perfluoroalkyl sulfonamide (generic).

Code of Federal Regulations, 2011 CFR

2011-07-01

... as a substituted perfluoroalkyl sulfonamide (PMN P-98-645) is subject to reporting under this section... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Substituted perfluoroalkyl sulfonamide... Specific Chemical Substances § 721.9573 Substituted perfluoroalkyl sulfonamide (generic). (a) Chemical...

40 CFR 721.9573 - Substituted perfluoroalkyl sulfonamide (generic).

Code of Federal Regulations, 2012 CFR

2012-07-01

... as a substituted perfluoroalkyl sulfonamide (PMN P-98-645) is subject to reporting under this section... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted perfluoroalkyl sulfonamide... Specific Chemical Substances § 721.9573 Substituted perfluoroalkyl sulfonamide (generic). (a) Chemical...

Design, synthesis, and biological evaluation of 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives as potential antihypertensive candidates.

PubMed

Liu, Jie; Liu, Qin; Yang, Xue; Xu, Shengtao; Zhang, Hengyuan; Bai, Renren; Yao, Hequan; Jiang, Jieyun; Shen, Mingqin; Wu, Xiaoming; Xu, Jinyi

2013-12-15

A series of novel 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives were designed and synthesized to develop new angiotensin II subtype 2 (AT2) receptor agonists as novel antihypertensive candidates. It was found that 14f (IC50=0.4 nM) and 15e (IC50=5.0 nM) displayed potent AT2 receptor affinity and selectivity in binding assays. Biological evaluation in vivo suggested that 14f is obviously superior to that of reference drug losartan in RHRs, and meanwhile, 14f has no significant impact on heart rate. The interesting activities of these compounds may make them promising candidates as antihypertensive agents. Copyright © 2013 Elsevier Ltd. All rights reserved.

Monoclonal antibodies with group specificity toward sulfonamides: Selection of hapten and antibody selectivity

USDA-ARS?s Scientific Manuscript database

Although many antibodies to sulfonamides have been generated, immunoassays based on the current available antibodies for large multi-sulfonamide screening programs have properties dependent on the immunizing hapten structure and have always suffered from high selectivity for individual sulfonamides....

Adsorptive removal of sulfonamide antibiotics in livestock urine using the high-silica zeolite HSZ-385.

PubMed

Fukahori, S; Fujiwara, T; Funamizu, N; Matsukawa, K; Ito, R

2013-01-01

The adsorptive removal of seven sulfonamide antibiotics using the high-silica zeolite HSZ-385 from distilled water, synthetic urine and real porcine urine was investigated. The pH greatly affected the adsorption efficiency, and the amounts of all sulfonamide antibiotics adsorbed on HSZ-385 decreased at alkaline conditions compared with that at neutral conditions. During storage, the pH and ammonium-ion concentration increased with urea hydrolysis for porcine urine. We clarified that the adsorption efficiency of sulfonamides in synthetic urine was equivalent to that in distilled water, suggesting that adsorption behavior was not affected by coexistent ions. HSZ-385 could adsorb sulfonamide antibiotics in real porcine urine even though the non-purgeable organic carbon concentration of porcine urine was 4-7 g/L and was two orders of magnitude higher than those of sulfonamides (10 mg/L each). Moreover, the adsorption of sulfonamides reached equilibrium within 15 min, suggesting that HSZ-385 is a promising adsorbent for removing sulfonamides from porcine urine.

Linear and branched perfluorooctane sulfonate (PFOS) isomer patterns differ among several tissues and blood of polar bears.

PubMed

Greaves, Alana K; Letcher, Robert J

2013-09-01

Perfluorooctane sulfonate (PFOS) is a globally distributed persistent organic pollutant that has been found to bioaccumulate and biomagnify in aquatic food webs. Although principally in its linear isomeric configuration, 21-35% of the PFOS manufactured via electrochemical fluorination is produced as a branched structural isomer. PFOS isomer patterns were investigated in multiple tissues of polar bears (Ursus maritimus) from East Greenland. The liver (n = 9), blood (n = 19), brain (n = 16), muscle (n = 5), and adipose (n = 5) were analyzed for linear PFOS (n-PFOS), as well as multiple mono- and di-trifluoromethyl-substituted branched isomers. n-PFOS accounted for 93.0 ± 0.5% of Σ-PFOS isomer concentrations in the liver, whereas the proportion was significantly lower (p<0.05) in the blood (85.4 ± 0.5%). Branched isomers were quantifiable in the liver and blood, but not in the brain, muscle, or adipose. In both the liver and blood, 6-perfluoromethylheptane sulfonate (P6MHpS) was the dominant branched isomer (2.61 ± 0.10%, and 3.26 ± 0.13% of Σ-PFOS concentrations, respectively). No di-trifluoromethyl-substituted isomers were detectable in any of the tissues analyzed. These tissue-specific isomer patterns suggest isomer-specific pharmacokinetics, perhaps due to differences in protein affinities, and thus differences in protein interactions, as well transport, absorption, and/or metabolism in the body. Crown Copyright © 2013. Published by Elsevier Ltd. All rights reserved.

Adsorption of sulfamethoxazole and sulfapyridine antibiotics in high organic content soils.

PubMed

Chen, Kuen-Lin; Liu, Li-Chun; Chen, Wan-Ru

2017-12-01

Many antibiotics, including sulfonamides, are being frequently detected in soil and groundwater. Livestock waste is an important source of antibiotic pollution, and sulfonamides may be present along with organic-rich substances. This study aims to investigate the sorption reaction of two sulfonamides, sulfamethoxazole (SMZ) and sulfapyridine (SPY) in two organic-rich sorbents: a commercial peat soil (38.41% carbon content) and a composted manure (24.33% carbon content). Batch reactions were conducted to evaluate the impacts of pH (4.5-9.5) and background ions (0.001 M-0.1 M CaCl 2 ) on their sorption. Both linear partitioning and Freundlich sorption isotherms fit the reaction well. The n values of Freundlich isotherm were close to 1 in most conditions suggesting that the hydrophobic partition is the major adsorption mechanism. In terms of SMZ, K d declined with increases in the pH. SPY has a pyridine group that is responsible for adsorption at high pH values, and thus, no significant trend between K d and pH was observed. At high pH ranges, SPY sorption deviated significantly from linear partitioning. The results suggested the sorption mechanism of these two sulfonamide antibiotics tended to be hydrophobic partitioning under most of the experimental conditions, especially at pH values lower than their corresponding pK a2. The fluorescence excitation emission matrix and dissolved organic carbon leaching test suggested composted manure has higher fulvic acid organics and that peat soil has higher humus-like organics. Small organic molecules showed stronger affinity toward sulfonamide antibiotics and cause the composted manure to exhibit higher sorption capacity. Overall, this study suggests that the chemical structure and properties of sulfonamides antibiotics and the type of organic matter in soils will greatly influence the fate and transport of these contaminants into the environment. Copyright © 2017 Elsevier Ltd. All rights reserved.

Nationwide Distribution of Per- and Polyfluoroalkyl Substances in Outdoor Dust in Mainland China From Eastern to Western Areas.

PubMed

Yao, Yiming; Sun, Hongwen; Gan, Zhiwei; Hu, Hongwei; Zhao, Yangyang; Chang, Shuai; Zhou, Qixing

2016-04-05

From eastern to western areas, per- and polyfluoroalkyl substances (PFASs) were detected at substantial levels in the outdoor dust across mainland China. Urban samples generally showed higher levels compared with those of rural samples. Compared with neutral PFASs, ionizable PFASs (C4-C12 perfluoroalkyl carboxylic acids and C4/C8 perfluoroalkyl sulfonic acids) were more abundant, with the highest total concentration up to 1.6 × 10(2) ng/g and perfluorooctanoic acid (PFOA) being a predominant analogue. Fluorotelomer alcohols (FTOHs) and polyfluoroalkyl phosphoric acid diesters (DiPAPs) were both detected in most samples with total concentrations of 0.12-32 and 0.030-20 ng/g, respectively. Perfluorooctane sulfonamidoethanols/sulfonamides (FOSE/As) were detected at low frequencies (<30%). In addition to partitioning to organic moiety, specific adsorption onto mineral particles can be important for PFASs to bind onto outdoor dust, especially for short-chain ionizable PFASs. The eastern plain areas were characterized by a higher contribution of long-chain ionizable PFASs; whereas the western high plateau areas were characterized by the dominating contribution of short-chain analogues. The difference suggests that the long-range atmospheric transport potential of PFASs from source regions to the inland is probably limited by the increase in altitude, and different sources from adjacent regions may influence the western border area of China.

Sorption of per- and polyfluoroalkyl substances (PFASs) on filter media: implications for phase partitioning studies.

PubMed

Chandramouli, Bharat; Benskin, Jonathan P; Hamilton, M Coreen; Cosgrove, John R

2015-01-01

Per- and polyfluoroalkyl substances (PFASs), including perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS), are ubiquitous in the environment. Investigations into their fate and potential phase-partitioning behavior require separating solid from aqueous phases via filtration. However, sorption of aqueous-phase PFASs on filtration media may lead to underestimation of PFAS concentrations in the aqueous phase. The authors investigated the sorption of perfluoroalkyl carboxylates, perfluoroalkyl sulfonates, perfluoroalkyl phosphonic acids, perfluoroalkyl phosphinic acids (PFPiAs), polyfluoroalkyl phosphate monoesters, polyfluoroalkyl phosphate diesters (diPAPs), fluorotelomer sulfonates, and perfluorooctane sulfonamide on filtration media. The effects of concentration (3 spiking levels), filter media (4 types), matrix (4 matrices), and compound structure on sorption are reported. Glass fiber filtration resulted in the least sorption, whereas polytetrafluoroethylene filters resulted in the most sorption (up to 98%). Analyte concentration had no significant effect. Sorption was generally consistent across matrix types except for samples affected by aqueous film forming foam deployment, which displayed high sorption of PFOS on nylon filters. Sorption usually increased with an increasing number of carbon or fluorine atoms and was most pronounced for PFPiAs and diPAPs (30–75% sorption). Overall, glass fiber filters are more recommended than nylon filters in environmental samples when phase separation is required. Use of filtration media for PFAS must be preceded by matrix-specific testing to account for unpredictable effects. (C)2014 SETAC

Synthesis of water-soluble polyamine derivatives effective as N-methyl-D-aspartate receptor antagonists.

PubMed

Masuko, Takashi; Yoshida, Shuhei; Metori, Koichi; Kizawa, Yasuo; Kusama, Tadashi; Miyake, Muneharu

2010-06-01

The novel water-soluble N-methyl-D-aspartate (NMDA) receptor antagonists, N-{4-[4-(4-Guanidinobutylamino)butylamino]butyl}-p-toluenesulfonamide trihydrochloride (1a, TsHSPMG), N-{4-[4-(4-Guanidinobutylamino)butylamino]butyl}butane-1-sulfonamide trihydrochloride (1b, BsHSPMG), N-{3-[4-(3-Guanidinopropylamino)butylamino]propyl}-p-toluenesulfonamide trihydrochroride (2a, TsSPMG) and N-{3-[4-(3-Guanidinopropylamino)butylamino]propyl}butane-1-sulfonamide trihydrochroride (2b, BsSPMG), were synthesized, and the effects of these polyamine derivatives on NMDA receptors were studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes. Although spermine potentiates 153% and 310% of NMDA (NR1A/NR2B) receptors in the presence of saturated and unsaturated glycine, respectively, all the novel polyamine derivatives, TsHSPMG (1a), BsHSPMG (1b), TsSPMG (2a) and BsSPMG (2b), significantly inhibited NR1A/NR2B receptors in both conditions. The degree of NMDA receptor inhibition by TsHSPMG (1a) and BsHSPMG (1b) was stronger than that by TsSPMG (2a) and BsSPMG (2b).

Technical Fact Sheet – Perfluorooctane Sulfonate (PFOS) and Perfluorooctanoic Acid (PFOA)

EPA Pesticide Factsheets

This fact sheet, developed by the U.S. Environmental Protection Agency (EPA) Federal Facilities Restoration and Reuse Office (FFRRO), provides a brief summary of the contaminant Perfluorooctane Sulfonate (PFOS) and Perfluorooctanoic Acid (PFOA)

Site-specific binding of a water molecule to the sulfa drugs sulfamethoxazole and sulfisoxazole: a laser-desorption isomer-specific UV and IR study.

PubMed

Uhlemann, Thomas; Seidel, Sebastian; Müller, Christian W

2018-03-07

To determine the preferred water molecule binding sites of the polybasic sulfa drugs sulfamethoxazole (SMX) and sulfisoxazole (SIX), we have studied their monomers and monohydrated complexes through laser-desorption conformer-specific UV and IR spectroscopy. Both the SMX and SIX monomer adopt a single conformer in the molecular beam. On the basis of their conformer-specific IR spectra in the NH stretch region, these conformers were assigned to the SMX and SIX global minimum structures, both exhibiting a staggered sulfonamide group and an intramolecular C-HO[double bond, length as m-dash]S hydrogen bond. The SMX-H 2 O and SIX-H 2 O complexes each adopt a single isomer in the molecular beam. Their isomeric structures were determined based on their isomer-specific IR spectra in the NH/OH stretch region. Quantum Theory of Atoms in Molecules analysis of the calculated electron densities revealed that in the SMX-H 2 O complex the water molecule donates an O-HN hydrogen bond to the heterocycle nitrogen atom and accepts an N-HO hydrogen bond from the sulfonamide NH group. In the SIX-H 2 O complex, however, the water molecule does not bind to the heterocycle but instead donates an O-HO[double bond, length as m-dash]S hydrogen bond to the sulfonamide group and accepts an N-HO hydrogen bond from the sulfonamide NH group. Both water complexes are additionally stabilized by a C ph -HOH 2 hydrogen bond. Interacting Quantum Atoms analysis suggests that all intermolecular hydrogen bonds are dominated by the short-range exchange-correlation contribution.

Development of flow-through and dip-stick immunoassays for screening of sulfonamide residues.

PubMed

Zhang, Hongyan; Zhang, Yan; Wang, Shuo

2008-08-20

Two formats of membrane-based competitive enzyme immunoassays (flow-through and dip-stick) have been developed for the screening of sulfonamide residues in pig muscle and milk. Membrane was coated with anti-sulfonamide antibody and a sulfonamide hapten D2-horseradish peroxidase (HRP) conjugant was used as the labeled antigen for competitive assay of sulfonamides. Visual detection limits of the flow-through or dip-stick assay were 1-5 microg L(-1) or 1-10 microg L(-1) in buffer for seven sulfonamides, respectively. Assay validation was performed using samples spiked with single sulfonamide, spiked samples were tested using the developed strip assays and results were compared with those obtained by a validated high-performance liquid chromatograph (HPLC) method. Results showed that the two strip assays were correlated well with HPLC, respectively. With assay times of 5 min (flow-through) and 15 min (dip-stick), these rapid tests could offer simple, rapid and cost-effective on-site screening tools to detect sulfonamides in pig muscle (flow-through or dip-stick) or milk (only dip-stick).

Toxicokinetics of perfluorooctane sulfonate in rainbow trout (Oncorhynchus mykiss)

EPA Science Inventory

Rainbow trout (Oncorhynchus mykiss) confined to respirometer-metabolism chambers were dosed with perfluorooctane sulfonate (PFOS) by intra-arterial injection and sampled to obtain concentration time-course data for plasma, and either urine or expired water. The data were then an...

Evaluation of the DNA damaging potential of cannabis cigarette smoke by the determination of acetaldehyde derived N2-ethyl-2'-deoxyguanosine adducts.

PubMed

Singh, Rajinder; Sandhu, Jatinderpal; Kaur, Balvinder; Juren, Tina; Steward, William P; Segerbäck, Dan; Farmer, Peter B

2009-06-01

Acetaldehyde is an ubiquitous genotoxic compound that has been classified as a possible carcinogen to humans. It can react with DNA to form primarily a Schiff base N(2)-ethylidene-2'-deoxyguanosine (N(2)-ethylidene-dG) adduct. An online column-switching valve liquid chromatography tandem mass spectrometry (LC-MS/MS) selected reaction monitoring (SRM) method was developed for the determination of N(2)-ethylidene-dG adducts in DNA following reduction with sodium cyanoborohydride (NaBH(3)CN) to the chemically stable N(2)-ethyl-2'-deoxyguanosine (N(2)-ethyl-dG) adduct. Accurate quantitation of the adduct was obtained by the addition of the [(15)N(5)]N(2)-ethyl-dG stable isotope-labeled internal standard prior to enzymatic hydrolysis of the DNA samples to 2'-deoxynucleosides with the incorporation of NaBH(3)CN in the DNA hydrolysis buffer. The method required 50 microg of hydrolyzed DNA on column for the analysis, and the limit of detection for N(2)-ethyl-dG was 2.0 fmol. The analysis of calf thymus DNA treated in vitro with acetaldehyde (ranging from 0.5 to 100 mM) or with the smoke generated from 1, 5, and 10 cannabis cigarettes showed linear dose-dependent increases in the level of N(2)-ethyl-dG adducts (r = 0.954 and r = 0.999, respectively). Similar levels (332.8 +/- 21.9 vs 348.4 +/- 19.1 adducts per 10(8) 2'-deoxynucleosides) of N(2)-ethyl-dG adducts were detected following the exposure of calf thymus DNA to 10 tobacco or 10 cannabis cigarettes. No significant difference was found in the levels of N(2)-ethyl-dG adducts in human lung DNA obtained from nonsmokers (n = 4) and smokers (n = 4) with the average level observed as 13.3 +/- 0.7 adducts per 10(8) 2'-deoxynucleosides. No N(2)-ethyl-dG adducts were detected in any of the DNA samples following analysis with the omission of NaBH(3)CN from the DNA hydrolysis buffer. In conclusion, these results provide evidence for the DNA damaging potential of cannabis smoke, implying that the consumption of cannabis cigarettes may be detrimental to human health with the possibility to initiate cancer development.

Indole cytosolic phospholipase A2 alpha inhibitors: discovery and in vitro and in vivo characterization of 4-{3-[5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoic acid, efipladib.

PubMed

McKew, John C; Lee, Katherine L; Shen, Marina W H; Thakker, Paresh; Foley, Megan A; Behnke, Mark L; Hu, Baihua; Sum, Fuk-Wah; Tam, Steve; Hu, Yonghan; Chen, Lihren; Kirincich, Steven J; Michalak, Ronald; Thomason, Jennifer; Ipek, Manus; Wu, Kun; Wooder, Lane; Ramarao, Manjunath K; Murphy, Elizabeth A; Goodwin, Debra G; Albert, Leo; Xu, Xin; Donahue, Frances; Ku, M Sherry; Keith, James; Nickerson-Nutter, Cheryl L; Abraham, William M; Williams, Cara; Hegen, Martin; Clark, James D

2008-06-26

The optimization of a class of indole cPLA 2 alpha inhibitors is described herein. The importance of the substituent at C3 and the substitution pattern of the phenylmethane sulfonamide region are highlighted. Optimization of these regions led to the discovery of 111 (efipladib) and 121 (WAY-196025), which are shown to be potent, selective inhibitors of cPLA 2 alpha in a variety of isolated enzyme assays, cell based assays, and rat and human whole blood assays. The binding of these compounds has been further examined using isothermal titration calorimetry. Finally, these compounds have shown efficacy when dosed orally in multiple acute and chronic prostaglandin and leukotriene dependent in vivo models.

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

PubMed Central

Kumar, Mohan; Mallesha, L.; Sridhar, M. A.; Kapoor, Kamini; Gupta, Vivek K.; Kant, Rajni

2012-01-01

In the title compound, C23H25BrN4O3S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 69.7 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 70.4 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 4-methyl benzene rings [centroid–centroid distance = 3.633 (2) Å]. The piperidine ring adopts a chair conformation. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds. PMID:23125637

Silver sulfadoxinate: Synthesis, structural and spectroscopic characterizations, and preliminary antibacterial assays in vitro

NASA Astrophysics Data System (ADS)

Zanvettor, Nina T.; Abbehausen, Camilla; Lustri, Wilton R.; Cuin, Alexandre; Masciocchi, Norberto; Corbi, Pedro P.

2015-02-01

The sulfa drug sulfadoxine (SFX) reacted with Ag+ ions in aqueous solution, affording a new silver(I) complex (AgSFX), which was fully characterized by chemical, spectroscopic and structural methods. Elemental, ESI-TOF mass spectrometric and thermal analyses of AgSFX suggested a [Ag(C12H13N4O2S)] empirical formula. Infrared spectroscopic measurements indicated ligand coordination to Ag(I) through the nitrogen atoms of the (deprotonated) sulfonamide group and by the pyrimidine ring, as well as through oxygen atom(s) of the sulfonamide group. These hypotheses were corroborated by 13C and 15N SS-NMR spectroscopy and by an unconventional structural characterization based on X-ray powder diffraction data. The latter showed that AgSFX crystallizes as centrosymmetric dimers with a strong Ag⋯Ag interaction of 2.7435(6) Å, induced by the presence of exo-bidentate N,N‧ bridging ligands and the formation of an eight-membered ring of [AgNCN]2 sequence, nearly planar. Participation of oxygen atoms of the sulfonamide residues generates in the crystal a 1D coordination polymer, likely responsible for its very limited solubility in all common solvents. Besides the analytical, spectroscopic and structural description, the antibacterial properties of AgSFX were assayed using disc diffusion methods against Escherichia coli and Pseudomonas aeruginosa (Gram-negative), and Staphylococcus aureus (Gram-positive) bacterial strains. The AgSFX complex showed to be active against Gram-positive and Gram-negative bacterial strains, being comparable to the activities of silver sulfadiazine.

21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2014 CFR

2014-04-01

... aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde... aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3-Methyl-3-phenyl glycidic acid ethyl ester (ethyl-methyl-phenyl-glycidate, so-called strawberry aldehyde, C-16 aldehyde). Ethyl...

Spectroscopic investigation (FT-IR, FT-Raman), HOMO-LUMO, NBO, and molecular docking analysis of N-ethyl-N-nitrosourea, a potential anticancer agent

NASA Astrophysics Data System (ADS)

Singh, Priyanka; Islam, S. S.; Ahmad, Hilal; Prabaharan, A.

2018-02-01

Nitrosourea plays an important role in the treatment of cancer. N-ethyl-N-nitrosourea, also known as ENU, (chemical formula C3H7N3O2), is a highly potent mutagen. The chemical is an alkylating agent and acts by transferring the ethyl group of ENU to nucleobases (usually thymine) in nucleic acids. The molecular structure of N-ethyl-N-nitrosourea has been elucidated using experimental (FT-IR and FT-Raman) and theoretical (DFT) techniques. APT charges, Mulliken atomic charges, Natural bond orbital, Electrostatic potential, HOMO-LUMO and AIM analysis were performed to identify the reactive sites and charge transfer interactions. Furthermore, to evaluate the anticancer activity of ENU molecular docking studies were carried out against 2JIU protein.

Highly efficient regioselective synthesis, spectroscopic characterizations and DFT calculations of novel hydroxymethylated 1,4-disubstituted-1,2,3-triazole-based sulfonamides

NASA Astrophysics Data System (ADS)

Taheri, Elmira; Mirjafary, Zohreh; Saeidian, Hamid

2018-04-01

The novel hydroxymethylated 1,4-disubstituted-1,2,3-triazole-based sulfonamides were synthesized in excellent yields and high regioselectivity via a one-pot, two-step, three-component reaction of N-propargylsulfonamides, sodium azide, and epoxide derivatives under green conditions. Green and mild reaction condition, commercially readily available and inexpensive starting materials, wide scope and easy work-up are the key features of the present method. The Li+ and Na+ ion affinities of the model structure have been also investigated by density functional theory (DFT) studies to find the applicability of these products as ligand in coordination chemistry.

EVALUATION OF PERFLUOROOCTANE SULFONATE IN THE RAT BRAIN

EPA Science Inventory

Perfluorooctane Sulfonate (PFOS) is an environmentally persistent chemical that has been detected in humans and wildlife. PFOS is primarily distributed in liver and blood. The current study evaluated the level of PFOS in the adult and neonatal rat brain and determined whether t...

Trimethoprim-sulfonamide Use during the First Trimester of Pregnancy and the Risk of Congenital Anomalies

PubMed Central

Hansen, Craig; Andrade, Susan E.; Freiman, Heather; Dublin, Sascha; Haffenreffer, Katie; Cooper, William O.; Cheetham, T.Craig; Toh, Sengwee; Li, De-Kun; Raebel, Marsha A.; Kuntz, Jennifer L.; Perrin, Nancy; Rosales, A.Gabriela; Carter, Shelley; Pawloski, Pamala A.; Maloney, Elizabeth M.; Graham, David J.; Sahin, Leyla; Scott, Pamela E.; Yap, John; Davis, Robert

2016-01-01

Background Sulfonamide antibacterials are widely used in pregnancy, but evidence about their safety is mixed. The objective of this study was to assess the association between first-trimester sulfonamide exposure and risk of specific congenital malformations. Methods Mother-infant pairs were selected from a cohort of 1.2 million liveborn deliveries (2001–2008) at 11 US health plans comprising the Medication Exposure in Pregnancy Risk Evaluation Program (MEPREP). Mothers with first-trimester trimethoprim-sulfonamide (TMP-SUL) exposures were randomly matched 1:1 to 1) a primary comparison group: mothers exposed to penicillins and/or cephalosporins, and 2) a secondary comparison group: mothers with no dispensing of an antibacterial, antiprotozoal, or antimalarial medication during the same time period. The outcomes were cardiovascular abnormalities, cleft palate/lip, clubfoot, and urinary tract abnormalities. Results We first identified 7,615 infants in the TMP-SUL exposure group, of which 7595 (99%) were exposed to a combination of TMP-SUL and the remaining 1% to sulfonamides alone. After matching (1:1) to the comparator groups and only including those with complete data on covariates there were 20,064 (n=6,688 per group) in the primary analyses. Overall, cardiovascular defects (1.52%) were the most common and cleft lip/palate (0.10%) the least common that were evaluated. Compared to penicillin/cephalosporin exposure, and no antibacterial exposure, TMP-SUL exposure was not associated with statistically significant elevated risks for cardiovascular, cleft lip/palate, clubfoot, or urinary system defects. Conclusions First trimester TMP-SUL exposure was not associated with a higher risk of the congenital anomalies studied, compared to exposure to penicillins and/or cephalosporins, or no exposure to antibacterials. PMID:26599424

New approach for assessing human perfluoroalkyl exposure via hair.

PubMed

Alves, Andreia; Jacobs, Griet; Vanermen, Guido; Covaci, Adrian; Voorspoels, Stefan

2015-11-01

In the recent years hair has been increasingly used as alternative matrix in human biomonitoring (HBM) of environmental pollutants. Sampling advantages and time integration of exposure assessment seems the most attractive features of hair matrix. In the current study, a novel miniaturized method was developed and validated for measuring 15 perfluoroalkyl substances (PFAS), including perfluoro n-butanoic acid (PFBA), perfluoro n-pentanoic acid (PFPeA), perfluoro n-hexanoic acid (PFHxA), perfluoro n-heptanoic acid (PFHpA), perfluor n-octanoic acid (PFOA), perfluoro n-nonanoic acid (PFNA), perfluoro tetradecanoic acid (PFTeDA), perfluorobutane sulfonic acid (PFBS), perfluoro pentane sulfonic acid (PFPeS), perfluorohexane sulfonic acid (PFHxS), perfluoroheptane sulfonic acid (PFHpS), perfluorooctane sulfonic acid (PFOS), perfluorononane sulfonic acid (PFNS), perfluorodecane sulfonic acid (PFDS) and perfluorododecane sulfonic acid (PFDoS) in human hair by liquid chromatography tandem mass spectrometry (LC-MS/MS). After extraction using ethyl acetate, dispersive ENVI-Carb was used for clean-up. Good intra- and inter-day precision for low (LQ 5 ng/g hair) and high spike (HQ 15n g/g) levels were achieved (in general RSD <10%). The accuracy was assessed using recoveries (%), which ranged between 68-118% (LQ) and 70-121% (HQ). The instrumental limit of detection (LODi) and limit of quantification (LOQi) were between 1-4 pg/g hair and 3-13 pg/g hair, respectively. The method limit of quantification (LOQm) ranged between 6 and 301 pg/g hair. The PFAS levels were measured in 30 human hair samples indicating that the levels are low (14-1534 pg/g hair). Some PFAS were not present in any hair sample (e.g. PFHpA, PFTeDA, PFNA, PFPeS, PFHpS, PFOS and PFNS), while other PFAS were frequently detected (PFBA, PFPeA, PFHxA, PFOA, PFBS, PFHxS, PFOS, PFDS and PFDoS) in human hair. Although levels in general were low, there is evidence of higher human exposure to some analytes, such as PFBA, PFPeA, PFHxA, PFOA, PFBS, PFHxS, and PFDoS. The current study shows that hair is a suitable alternative non-invasive matrix for exposure assessment of PFAS. Copyright © 2015 Elsevier B.V. All rights reserved.

Alkylation of deoxyribonucleic acid by carcinogens dimethyl sulphate, ethyl methanesulphonate, N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea. Relative reactivity of the phosphodiester site thymidylyl(3'-5')thymidine.

PubMed Central

Swenson, D H; Lawley, P D

1978-01-01

1. The ethyl phosphotriester of thymidylyl(3'-5')thymidine, dTp(Et)dT, was identified as a product from reaction of DNA with N-ethyl-N-nitrosourea, by procedures parallel to those reported previously for the methyl homologue produced by N-methyl-N-nitrosourea. 2. Enzymic degradation to yield alkyl phosphotriesters from DNA alkylated by these carcinogens and by dimethyl sulphate and ethyl methanesulphonate was studied quantitatively, and the relative yields of the triesters dTp(Alk)dT were determined. The relative reactivity of the phosphodiester group dTpdT to each of the four carcinogens was thus obtained, and compared with that of DNA overall, or with that of the N-7 atom of guanine in DNA. Relative reactivity of the phosphodiester group was lowest towards dimethyl sulphate, the least electrophilic of the reagents used, and was highest towards N-ethyl-N-nitrosourea, the most electrophilic reagent. 3. The nature of the alkyl group transferred also influenced reactivity of the phosphodiester site, since this site was relatively more reactive towards ethylation than would be predicted simply from the known Swain-Scott s values of the alkylating agents. It was therefore suggested that the steric accessibility of the weakly nucleophilic phosphodiester group on the outside of the DNA macromolecule favours its reaction with ethylating, as opposed to methylating, reagents. 4. Taking a value of the Swain-Scott nucleophilicity (n) of 2.5 for an average DNA nucleotide unit [Walles & Ehrenberg (1969) Acta Chem. Scand. 23, 1080-1084], a value of n of about 1 for the phosphodiester group was deduced, and this value was found to be 2-3 units less than that for the N-7 atom of guanine in DNA. 5. The reactivity of DNA overall was markedly high towards the alkylnitrosoureas, despite their relatively low s values. This was ascribed to an electrostatic factor that favoured reaction of the negatively charged polymer with alkyldiazonium cation intermediates. PMID:208508

Study of a series of cobalt(II) sulfonamide complexes: Synthesis, spectroscopic characterization, and microbiological evaluation against M. tuberculosis. Crystal structure of [Co(sulfamethoxazole)2(H2O)2]·H2O

NASA Astrophysics Data System (ADS)

Mondelli, Melina; Pavan, Fernando; de Souza, Paula C.; Leite, Clarice Q.; Ellena, Javier; Nascimento, Otaciro R.; Facchin, Gianella; Torre, María H.

2013-03-01

Nowadays, the research for new and better antimicrobial compounds is an important field due to the increase of immunocompromised patients, the use of invasive medical procedures and extensive surgeries, among others, that can affect the incidence of infections. Another big problem associated is the occurrence of drug-resistant microbial strains that impels a ceaseless search for new antimicrobial agents. In this context, a series of heterocyclic-sulfonamide complexes with Co(II) was synthesized and characterized with the aim of obtaining new antimicrobial compounds. The structural characterization was performed using different spectroscopic methods (UV-Vis, IR, and EPR). In spite of the fact that the general stoichiometry for all the complexes was Co(sulfonamide)2·nH2O, the coordination atoms were different depending on the coordinated sulfonamide. The crystal structure of [Co(sulfamethoxazole)2(H2O)2]·H2O was obtained by X-ray diffraction showing that Co(II) is in a slightly tetragonal distorted octahedron where sulfamethoxazole molecules act as a head-to-tail bridges between two cobalt atoms, forming polymeric chains. Besides, the activity against Mycobacterium tuberculosis, one of the responsible for tuberculosis, and the cytotoxicity on J774A.1 macrophage cells were evaluated.

Comparing Single and Repeated Dosimetry Data for Perfluorooctane Suflonate in Rats

EPA Science Inventory

Perfluorooctane sulfonate (PFOS) is a member of a class of perfluorinated chemicals used in a variety of consumer and industrial applications because of their oleophobic and hydrophobic properties. It has been shown to cause toxicity in adult and developing laboratory animals. Be...

N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-chloro­benzene­sulfonamide

PubMed Central

Kumar, Mohan; Mallesha, L.; Sridhar, M. A.; Kapoor, Kamini; Gupta, Vivek K.; Kant, Rajni

2012-01-01

In the title compound, C21H20BrClN4O4S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by a dihedral angle of 70.2 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.5 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 4-chloro­benzene rings [centroid–centroid distance = 3.978 (2) Å]. The morpholine ring adopts a chair conformation. In the crystal, mol­ecules are linked into inversion dimers by pairs of C—H⋯N hydrogen bonds and these dimers are further connected by N—H⋯O hydrogen bonds, forming a tape along the a axis. PMID:22969673

Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives

PubMed Central

Pérez-Gutiérrez, Enrique; Percino, M. Judith; Chapela, Víctor M.; Cerón, Margarita; Maldonado, José Luis; Ramos-Ortiz, Gabriel

2011-01-01

We synthesized three novel highly fluorescent compounds, 2-(2’-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile, 2-(3”-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile, and 2-(4-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile by Knoevenagel condensation. The first two were synthesized without solvent in the presence of piperidine as a catalyst; the third was synthesized without a catalyst and with N,N-dimethylformamide as a solvent. In solution, the molar absorption coefficients showed absorptions at 380, 378, and 396 nm, respectively; in solid state, absorptions were at 398, 390, and 442 nm, respectively. The fluorescence emission was at 540, 540 and 604 nm, respectively, the 2-(4-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile showed a red shift in the emission of 64 nm compared to the other two compounds. The fluorescence quantum yield for the compounds in powder form showed values of 0.05, 0.14, and 0.006, respectively; compared with the value measured for the Alq3 reference, 2-(3”-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile had a lightly higher value. The third harmonic generation measurement for 2-(2’-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile yielded a χ(3) value of 5.5 × 10−12 esu, similar to that reported for commercial polymers. PMID:28880006

Characterization of a streptomycin-sulfonamide resistance plasmid from Actinobacillus pleuropneumoniae.

PubMed Central

Willson, P J; Deneer, H G; Potter, A; Albritton, W

1989-01-01

An Actinobacillus pleuropneumoniae strain contained a plasmid (pHD8.1) conferring resistance to streptomycin and sulfonamide. Restriction endonuclease mapping and DNA-DNA hybridization showed that pHD8.1 is related to RSF1010 from Salmonella panama, which also confers resistance to streptomycin and sulfonamide, and to pHD148 from Haemophilus ducreyi, which confers resistance only to sulfonamide. Images PMID:2541656

Perfluorooctane sulfonate (PFOS) depletion in beef cattle

USDA-ARS?s Scientific Manuscript database

Perfluorooctane sulfonate (PFOS) is an industrial chemical that is used as a surfactant in several manufactured consumer products but is also a breakdown product from other chemical surfactants. As a result of its extensive use, PFOS is ubiquitous in the environment and is often detected in biosoli...

Effects of prenatal exposure to perfluorooctane sulfonate on the developing lung in the rat

EPA Science Inventory

Perfluorooctane sulfonate (PFOS), an environmentally stable industrial and household compound, has been detected in human and wildlife sera. Chronic prenatal exposure to PFOS in rodents leads to mortality in newborns within hours to days after birth. We have demonstrated that tr...

The bioconcentration factor of perfluorooctane sulfonate is significantly larger than that of perfluorooctanoate in wild turtles (Trachemys scripta elegans and Chinemys reevesii): an Ai river ecological study in Japan.

PubMed

Morikawa, Akiko; Kamei, Naoya; Harada, Kouji; Inoue, Kayoko; Yoshinaga, Takeo; Saito, Norimitsu; Koizumi, Akio

2006-09-01

Turtles rank high in the river food chain, and are suitable for predicting the bioconcentrations of chemicals through the food chain. Trachemys scripta elegans (N=46) and Chinemys reevesii (N=51) were captured in a river in Japan, from September to October 2003 and April to June 2004. Surface water samples were collected simultaneously from the same sites at which the turtles were caught. Serum perfluorooctane sulfonate (PFOS) ranged from 2.4 to 486 microg/L, while water PFOS levels ranged from 2.9 to 37 ng/L. The geometric mean (GM) (geometric standard deviation, GSD) of the bioconcentration factor (BCF) of PFOS was 10,964 (2.5). In contrast, the perfluorooctanoate (PFOA) level in water ranged from 16.7-87,100 ng/L, and serum PFOA ranged from <0.2 to 870 microg/L. The GM (GSD) of the BCF of PFOA was 3.2 (7.9). Furthermore, the BCF of PFOA decreased as the PFOA level in the surface water increased. PFOS could be preferentially bioconcentrated in biota, and PFOA, slightly bioconcentrated.

Design and synthesis of sulfonamide-substituted diphenylpyrimidines (SFA-DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B-cell lymphoblastic leukemia.

PubMed

Liu, He; Qu, Menghua; Xu, Lina; Han, Xu; Wang, Changyuan; Shu, Xiaohong; Yao, Jihong; Liu, Kexin; Peng, Jinyong; Li, Yanxia; Ma, Xiaodong

2017-07-28

A new series of diphenylpyrimidine derivatives (SFA-DPPYs) were synthesized by introducing a functional sulfonamide into the C-2 aniline moiety of pyrimidine template, and then were biologically evaluated as potent Bruton's tyrosine kinase (BTK) inhibitors. Among these molecules, inhibitors 10c, 10i, 10j and 10k displayed high potency against the BTK enzyme, with IC 50 values of 1.18 nM, 0.92 nM, 0.42 nM and 1.05 nM, respectively. In particular, compound 10c could remarkably inhibit the proliferation of the B lymphoma cell lines at concentrations of 6.49 μM (Ramos cells) and 13.2 μM (Raji cells), and was stronger than the novel agent spebrutinib. In addition, the inhibitory potency toward the normal PBMC cells showed that inhibitor 10c possesses low cell cytotoxicity. All these explorations indicated that molecule 10c could serve as a valuable inhibitor for B-cell lymphoblastic leukemia treatment. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Simultaneous preconcentration and removal of iron, chromium, nickel with N,N'-etylenebis-(ethane sulfonamide) ligand on activated carbon in aqueous solution and determination by ICP-OES.

PubMed

Karacan, Mehmet Sayim; Aslantaş, Neslihan

2008-07-15

In this study, Fe, Cr and Ni have been preconcentrated and removed by using N,N'-ethylenebis (ethane sulfonamide), (ESEN) ligand on activated carbon (AC) in aqueous solution. For this purpose, complexes between these metals and ligands have been investigated and used in preconcentration and removal studies. Factors which have affected adsorption of metals on activated carbon have been optimized. Adsorbed metals have been preconcentrated 10-fold and determined by ICP-OES. Interferences of Ca, Mg and K to this process have been investigated. The proposed method has been applied to the tap water and Ankara Creek water in order to Fe, Cr, and Ni remediation and preconcentration. Determination of metals by ICP-OES has been checked with standard reference material (NIST 1643e). The proposed method provides the recoveries of 87%, 108% and 106% for Fe, Cr and Ni, respectively, in preconcentration. It also provides the removal of Fe, Cr and Ni by 93%, 100% and 100% removal from waters, respectively.

Synthetic, XRD, non-covalent interactions and solvent dependent nonlinear optical studies of Sulfadiazine-Ortho-Vanillin Schiff base: (E)-4-((2-hydroxy-3-methoxy- benzylidene) amino)-N-(pyrimidin-2-yl)benzene-sulfonamide

NASA Astrophysics Data System (ADS)

Shahid, Muhammad; Salim, Muhammad; Khalid, Muhammad; Tahir, Muhammad Nawaz; Khan, Muhammad Usman; Braga, Ataualpa Albert Carmo

2018-06-01

In this study, Sulfadiazine-Ortho-Vanillin Schiff base namely (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)sbnd N-(pyrimidin-2-yl)benzene-sulfonamide (BS) was synthesized. Chemical characterization and computational studies using different techniques like XRD, FT-IR, UV-Vis, NBO, FMO, and MEP have been employed. Density functional theory (DFT) calculations have been performed at M06-2X/6-311 + G(d,p) level of theory to obtain optimized geometry and vibrational wave numbers for (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)sbnd N-(pyrimidin-2-yl)benzene-sulfonamide (BS). The DFT optimized geometry supports the experimental XRD parameters. Frontier molecular orbital (FMO) energies and molecular electrostatic potential (MEP) surfaces have been executed at M06-2X/6-311 + G(d,p) level of theory. NBO analysis has been carried out at M06-2X/6-311 + G(d,p) level which not only discovered the hyper conjugative interactions and stability in title molecule but also reconfirmed the existence of Nsbnd H⋯N hydrogen bonds between the dimer. The findings of small EHOMO-ELUMO gap shows less hardness and larger softness values which suggested the bioactiveness of the title molecule. Finally, the effect of solvent on nonlinear optical (NLO) properties has been executed using M06-2X level of theory and 6-311 + G (d,p) basis set. The solvent polarity enhanced the NLO response from 3.62 × 10-30 esu to 4.66 × 10-30 esu indicating the considerable NLO character hence in general may have potential applications in the development of non-linear optical materials.

Stability Indicating HPLC Method for the Determination of Chiral Purity of R-(-)-5-[2-aminopropyl]-2-methoxybenzene Sulfonamide.

PubMed

Kasawar, G B; Farooqui, M N

2009-09-01

A chiral reverse phase liquid chromatographic method was developed for the enantiomeric resolution of racemic mixture of (-)-5-[2-aminopropyl]-2-methoxybenzene sulfonamide in bulk drug. The enantiomeric separation of sulfonamide was resolved on a Crownpak CR (+) column using perchloric acid buffer of pH 1.0 as mobile phase and with UV detection at 226 nm. The method is validated and proved to be robust. The limit of detection and quantification of S (-)-(5)-[2-aminopropyl]-2-methoxybenzene sulfonamide] was found to be 0.084 and 0.159 mug/ml, respectively for 20 mul injection volume. The percentage recovery of S (-)-(5)-[2-aminopropyl]-2-methoxybenzene sulfonamide] ranged from 99.57 to 101.88 in bulk drug samples of R (-)-(5)-[2- aminopropyl]-2-methoxybenzene sulfonamide].

Stability Indicating HPLC Method for the Determination of Chiral Purity of R-(-)-5-[2-aminopropyl]-2-methoxybenzene Sulfonamide

PubMed Central

Kasawar, G. B.; Farooqui, M. N.

2009-01-01

A chiral reverse phase liquid chromatographic method was developed for the enantiomeric resolution of racemic mixture of (-)-5-[2-aminopropyl]-2-methoxybenzene sulfonamide in bulk drug. The enantiomeric separation of sulfonamide was resolved on a Crownpak CR (+) column using perchloric acid buffer of pH 1.0 as mobile phase and with UV detection at 226 nm. The method is validated and proved to be robust. The limit of detection and quantification of S (-)-(5)-[2-aminopropyl]-2-methoxybenzene sulfonamide] was found to be 0.084 and 0.159 μg/ml, respectively for 20 μl injection volume. The percentage recovery of S (-)-(5)-[2-aminopropyl]-2-methoxybenzene sulfonamide] ranged from 99.57 to 101.88 in bulk drug samples of R (-)-(5)-[2- aminopropyl]-2-methoxybenzene sulfonamide]. PMID:20502572

PARTIAL LIFE-CYCLE TOXICITY AND BIOCONCENTRATION MODELLING OF PERFLUOROOCTANE SULFONATE (PFOS) IN THE NORTHERN LEOPARD FROG (RANA PIPIENS)

EPA Science Inventory

A number of recent monitoring studies have demonstrated elevated concentrations of perfluorooctane sulfonate (PFOS) in humans and wildlife throughout the world. Although no longer manufactured in the U.S., the global distribution and relative persistence of PFOS indicates a need ...

GENE PROFILING IN WILD-TYPE AND PPARα-NULL MICE EXPOSED TO PERFLUOROOCTANE SULFONATE

EPA Science Inventory

Perfluorooctane sulfonate (PFOS), a perfluoroalkyl acid (PFAA), is a persistent environmental contaminant found in the tissues of humans and wildlife. Over the last decade, health concerns have been raised, in part, because of the long half-life of PFOS and other PFAAs in humans,...

Absorption and excretion of 14C-perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) in beef cattle

USDA-ARS?s Scientific Manuscript database

Perfluoroalkyl compounds such as perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) are industrial chemicals that are environmentally persistent. Both PFOS and PFOA are found in biosolids, and the application of these contaminated biosolids to pastures has raised concerns about possi...

PERFLUOROOCTANE SULFONATE (PFOS) DISRUPTS THE THYROID STATUS IN LABORATORY RODENTS

EPA Science Inventory

PERFLUOROOCTANE SULFONATE (PFOS) DISRUPTS THE THYROID STATUS IN LABORATORY RODENTS. C. Lau, J.R. Thibodeaux, R.G. Hanson, B.E. Gray and J.M. Rogers. Reprod. Tox. Div. NHEERL, US EPA, Research Triangle Park, NC.

PFOS is an environmental contaminant ubiquitously found in h...

Gene Expression Profiling in the Liver and Lung of Perfluorooctane Sulfonate-Exposed Mouse Fetuses: Comparison to Changes Induced by Exposure to Perfluorooctanoic Acid

EPA Science Inventory

Perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) are environmental contaminants found in the tissues of humans and wildlife. They are activators of peroxisome proliferator-activated receptor-alpha (PPARα) and exhibit hepatocarcinogenic potential in rats. PFOS...

Recent advances in medicinal chemistry of sulfonamides. Rational design as anti-tumoral, anti-bacterial and anti-inflammatory agents.

PubMed

Shah, Syed Shoaib Ahmad; Rivera, Gildardo; Ashfaq, Muhammad

2013-01-01

Now-a-days, cancer is becoming one of the major problems of public health in the world. Pharmacology treatment is a way to increase quality and long life. Predominantly, in last decade sulfonamide derivatives have been described as potential carbonic anhydrase inhibitors. In the present work, we describe recent advances during the last decade in medicinal chemistry of sulfonamides derivatives with some examples of rational design as anti-tumoral, antibacterial and anti-inflammatory agents. We show strategy design, structure-activity relationship, biological activity and advances of new sulfonamide compounds that have more health significance than some clinically used sulfonamides.

Review on enzyme-linked immunosorbent assays for sulfonamide residues in edible animal products.

PubMed

Zhang, Hongyan; Wang, Shuo

2009-10-31

The current status of enzyme-linked immunosorbent assays (ELISAs) for sulfonamides in edible animal products is reviewed. The attention was focused on the design and synthesis of haptens, conjugation to carrier protein, production of antibody, application of homologous and heterologous systems, as well as the molecular modeling of the haptens and sulfonamides. Researches have shown that sulfonamides seem to be particularly resistant to attempts to produce broad specificity antibodies. By summarizing the available research on sulfonamide ELISAs, it is hoped that it can be considered as a basis for further investigation aimed at developing the most efficient approaches for detection.

Comparison of PFASs contamination in the freshwater and terrestrial environments by analysis of eggs from osprey (Pandion haliaetus), tawny owl (Strix aluco), and common kestrel (Falco tinnunculus)

DOE Office of Scientific and Technical Information (OSTI.GOV)

Eriksson, Ulrika, E-mail: ulrika.eriksson@oru.se; Roos, Anna; Lind, Ylva

The level of PFAS (per- and polyfluorinated alkyl substances) contamination in freshwater and terrestrial Swedish environments in 2013/2014 was assessed by analyzing a range of perfluorinated alkyl acids, fluorotelomer acids, sulfonamides, sulfonamidoethanols and polyfluoralkyl phosphate diesters (diPAPs) in predator bird eggs. Stable isotopes ({sup 13}C and {sup 15}N) were analyzed to elucidate the dietary source. The tawny owl (Strix aluco, n=10) and common kestrel (Falco tinnunculus, n=40), two terrestrial species, and the osprey (Pandion haliaetus, n=30), a freshwater specie were included. In addition, a temporal trend (1997–2001, 2008–2009, 2013) in osprey was studied as well. The PFAS profile was dominatedmore » by perfluorooctane sulfonic acid (PFOS) in eggs from osprey and tawny owl, while for common kestrel perfluorinated carboxylic acids (∑PFCA) exceeded the level of PFOS. PFOS concentration in osprey eggs remained at the same level between 1997 and 2001 and 2013. For the long-chained PFCAs, there were a significant increase in concentrations in osprey eggs between 1997 and 2001 and 2008–2009. The levels of PFOS and PFCAs were about 10 and five times higher, respectively, in osprey compared to tawny owl and common kestrel. Evidence of direct exposure from PFCA precursor compounds to birds in both freshwater and terrestrial environment was observed. Low levels of diPAPs were detected in a few samples of osprey (<0.02–2.4 ng/g) and common kestrel (<0.02–0.16 ng/g) eggs, and 6:2 FTSA was detected in a majority of the osprey eggs (<6.3–52 ng/g). One saturated telomer acid (7:3 FTCA), which is a transformation marker from precursor exposure, was detected in all species (<0.24–2.7 ng/g). The {sup 15}N data showed higher levels in osprey eggs compared to tawny owl and common kestrel, indicating that they feed on a 2–3 times higher trophic level. We conclude that ospreys are continuously exposed to PFAS at levels where adverse toxic effects have been observed in birds. - Highlights: • Levels in the freshwater environment exceeded those of the terrestrial environment. • Birds in both freshwater and terrestrial environment are exposed to PFCA precursors. • No significant change of PFOS level in osprey eggs between 1997 and 2001 and 2013. • PFAS levels pose a risk to birds in the freshwater environment.« less

Ultrasensitive Immunochromatographic Strip for Fast Screening of 27 Sulfonamides in Honey and Pork Liver Samples Based on a Monoclonal Antibody.

PubMed

Chen, Yanni; Guo, Lingling; Liu, Liqiang; Song, Shanshan; Kuang, Hua; Xu, Chuanlai

2017-09-20

Group-specific monoclonal antibodies (Mabs) with selectivity for 27 sulfonamides were developed based on new combinations of immunogen and coating antigen. The Mab was able to recognize 27 sulfonamides with 50% inhibition concentration (IC 50 ) values ranging from 0.15 to 15.38 μg/L. In particular, the IC 50 values for five sulfonamides (sulfamethazine, sulfaquinoxaline, sulfamonomethoxine, sulfadimethoxine, and sulfamethoxazole) were 0.51, 0.15, 0.56, 0.54, and 2.14 μg/L, respectively. On the basis of the Mab, an immunochromatographic lateral flow strip test was established for rapid screening of sulfonamides in honey samples. The visual limit of detection of the strip test for most sulfonamides in spiked honey samples was below 10 μg/kg, satisfying the requirements of authorities. Positive honey and pork liver samples, which had been confirmed by high-performance liquid chromatography/mass spectrometry, were used to validate the reliability of the proposed strip test. The immunochromatographic lateral flow strip test provides a rapid and convenient method for fast screening of sulfonamides in honey samples.

40 CFR 721.4090 - Ethanaminium, N-[bis(diethylamino)-methylene]-N-ethyl-, bromide.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ethanaminium, N-[bis(diethylamino)-methylene]-N-ethyl-, bromide. 721.4090 Section 721.4090 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.4090 Ethanaminium, N-[bis(diethylamino)-methylene]-N...

40 CFR 721.4090 - Ethanaminium, N-[bis(diethylamino)-methylene]-N-ethyl-, bromide.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ethanaminium, N-[bis(diethylamino)-methylene]-N-ethyl-, bromide. 721.4090 Section 721.4090 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.4090 Ethanaminium, N-[bis(diethylamino)-methylene]-N...

An Arg-Gly-Asp peptide stimulates Ca2+ efflux from osteoclast precursors through a novel mechanism

NASA Technical Reports Server (NTRS)

Yamakawa, K.; Duncan, R.; Hruska, K. A.

1994-01-01

We examined the effect of a peptide containing the Arg-Gly-Asp (RGD) sequence on 45Ca2+ efflux from osteoclast precursors. 45Ca(2+)-loaded osteoclast precursors were treated with GRGDSP (170 microM) for 10 min after 30 min of basal perfusion with a bicarbonate-containing buffer. GRGDSP significantly increased fractional efflux of Ca2+ from treated cells compared with vehicle-treated cells (P < 0.01) or cells treated with up to 200 micrograms/ml of a control peptide containing GRGESP. The effect of RGD was sustained for 15 min after the peptide was removed from the perfusate, but control levels of Ca2+ efflux returned by 1 h. The Ca2+ efflux effect of GRGDSP was most likely due to activation of the plasma membrane Ca(2+)-adenosinetriphosphatase (Ca(2+)-ATPase) pump, as indicated by its inhibition with vanadate and a calmodulin antagonist, N-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamide, and the absence of an effect of Na+/Ca2+ exchange inhibition. An inhibitor of cyclic nucleotide-dependent protein kinases, N-[2-(methylamino)ethyl]-5-isoquinoline-sulfonamide (0.1 mM), failed to inhibit GRGDSP-stimulated Ca2+ efflux. However, genistein and herbimycin A, inhibitors of protein-tyrosine kinases, blocked Ca2+ efflux stimulated by GRGDSP. The results indicate that RGD sequences of matrix proteins may stimulate Ca2+ efflux from osteoclasts through activation of protein-tyrosine kinases and suggest that GRGDSP-stimulated Ca2+ efflux is mediated via the plasma membrane Ca(2+)-ATPase.

Synthesis of Novel Chiral Sulfonamide-Bearing 1,2,4-Triazole-3-thione Analogs Derived from D- and L-Phenylalanine Esters as Potential Anti-Influenza Agents.

PubMed

Başaran, Eyüp; Karaküçük-Iyidoğan, Ayşegül; Schols, Dominique; Oruç-Emre, Emine Elçin

2016-06-01

Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR, (1) H NMR, (13) C NMR, 2D NMR (HETCOR), and mass spectral data. All compounds were tested in vitro antiviral activity against a broad variety of DNA and RNA viruses and in vitro cytostatic activity against murine leukemia (L1210), human T-lymphocyte (CEM) and human cervix carcinoma (HeLa) cell lines. Although enantiopure 1,2,4-triazole-3-thione analogs in (R) configuration emerged as promising anti-influenza A H1N1 subtype in Madin Darby canine kidney cell cultures (MDCK), their enantiomers exhibited no activity. Especially compounds , , , , and (EC50 : 6.5, 6.1, 2.4, 1.6, 1.7 μM, respectively) had excellent activity against influenza A H1N1 subtype compared to the reference drug ribavirin (EC50 : 8.0 μM). Several compounds have been found to inhibit proliferation of L1210, CEM and HeLa cell cultures with IC50 in the 12-53 μM range. Compound and in (R) configuration were the most active compounds (IC50 : 12-22 μM for and IC50 : 19-23 μM for ). Chirality 28:495-513, 2016. © 2016 Wiley Periodicals, Inc. © 2016 Wiley Periodicals, Inc.

Aerobic biodegradation of the sulfonamide antibiotic sulfamethoxazole by activated sludge applied as co-substrate and sole carbon and nitrogen source.

PubMed

Müller, Elisabeth; Schüssler, Walter; Horn, Harald; Lemmer, Hilde

2013-08-01

Potential aerobic biodegradation mechanisms of the widely used polar, low-adsorptive sulfonamide antibiotic sulfamethoxazole (SMX) were investigated in activated sludge at bench scale. The study focused on (i) SMX co-metabolism with acetate and ammonium nitrate and (ii) SMX utilization when present as the sole carbon and nitrogen source. With SMX adsorption being negligible, elimination was primarily based on biodegradation. Activated sludge was able to utilize SMX both as a carbon and/or nitrogen source. SMX biodegradation was enhanced when a readily degradable energy supply (acetate) was provided which fostered metabolic activity. Moreover, it was raised under nitrogen deficiency conditions. The mass balance for dissolved organic carbon showed an incomplete SMX mineralization with two scenarios: (i) with SMX as a co-substrate, 3-amino-5-methyl-isoxazole represented the main stable metabolite and (ii) SMX as sole carbon and nitrogen source possibly yielded hydroxyl-N-(5-methyl-1,2-oxazole-3-yl)benzene-1-sulfonamide as a further metabolite. Copyright © 2013 Elsevier Ltd. All rights reserved.

Facile dimethyl amino group triggered cyclic sulfonamides synthesis and evaluation as alkaline phosphatase inhibitors.

PubMed

Bhatti, Huma Aslam; Khatoon, Memoona; Al-Rashida, Mariya; Bano, Huma; Iqbal, Nafees; Zaib-Un-Nisa; Yousuf, Sammer; Khan, Khalid Mohammed; Hameed, Abdul; Iqbal, Jamshed

2017-04-01

Owing to the biological importance of cyclic sulfonamides (sultams), herein we report a new, facile and cost-effective method for the synthesis of sultams that makes use of a reaction between dansyl amide and easily accessible benzaldehydes under mildly acidic conditions. All compounds were obtained in good yields (69-96%). Consequently a series of cyclic sulfonamides (7a-7n) was synthesized and characterized using FTIR, MS and NMR spectroscopy, crystal structure of compound 7b has also been determined. All compounds were evaluated for their potential to inhibit alkaline phosphatase (bTNAP and bIAP). All compounds were found to be excellent inhibitors of bTNAP with IC 50 values in lower micro-molar range (0.11-6.63μM). Most of the compounds were selective inhibitors of bTNAP over bIAP. Only six compounds were found to be active against bIAP (IC 50 values in the range 0.38-3.48μM). Molecular docking studies were carried out to identify and rationalize the structural elements necessary for efficient AP inhibition. Copyright © 2017 Elsevier Inc. All rights reserved.

A field trial of ethyl hexanediol against Aedes dorsalis in Sonoma County, California.

PubMed

Rutledge, L C; Hooper, R L; Wirtz, R A; Gupta, R K

1989-09-01

The repellent ethyl hexanediol (2-ethyl-1,3-hexanediol) was tested against the mosquito Aedes dorsalis in a coastal salt marsh in California. The experimental design incorporated a linear regression model, sequential treatments and a proportional end point (95%) for protection time. The protection time of 0.10 mg/cm2 ethyl hexanediol was estimated at 0.8 h. This time is shorter than that obtained previously for deet (N,N-diethyl-3-methylbenzamide) against Ae. dorsalis (4.4 h).

Antibacterial activity of sulfamethoxazole transformation products (TPs): general relevance for sulfonamide TPs modified at the para position.

PubMed

Majewsky, Marius; Wagner, Danny; Delay, Markus; Bräse, Stefan; Yargeau, Viviane; Horn, Harald

2014-10-20

Sulfonamide antibiotics undergo transformation in the aquatic environment through biodegradation, photolysis, or hydrolysis. In this study, the residual antibacterial activity of 11 transformation products (TPs) of sulfamethoxazole (SMX) was investigated with regard to their in vitro growth and luminescence inhibition on Vibrio fischeri (30 min and 24 h exposure). Two transformation products, 4-hydroxy-SMX and N(4)-hydroxy-acetyl-SMX, were synthesized in-house and confirmed by nuclear magnetic resonance and high-resolution mass spectrometry. Results of individual compound experiments showed that TPs modified at the para amino group still exhibit clear antibacterial effects, whereas TPs resulting from breakdown of the SMX structure lost this mechanism of action. 4-NO2- and 4-OH-SMX were found to inhibit growth to a clearly greater extent than the parent compound, SMX. In contrast, the N(4)-acetyl- and N(4)-hydroxy-acetyl-derivatives retain less than 10 and 5% of the effect of SMX on growth and luminescence inhibition, respectively. The effect of a mixture of para-modified TPs was observed to be additive. Considering the homologous series of sulfa drugs widely prescribed and their common mechanism of action, the potential environmental impact must consider the total amount of sulfonamide antibiotics and their derivative TPs, which might end up in a water body. Extrapolating the results obtained here for the para TPs of SMX to other sulfa drugs and determining the persistence and occurrence of these compounds in the aquatic environment is required for improved risk assessment.

[Synthesis of new nitrosoureas].

PubMed

Papadaki-Valiraki, A; Siatra-Papastaikoudi, T; Skaltsounis, A L; Roussakis, C

1989-01-01

Two chemical pathways were used for the synthesis of three new N'-(2-chloroethyl)-N-[2-(4-alkoxyphenylthio)ethyl]-N'-nitrosoureas and two new N'-(2-chloroethyl)-N)[2-(4-alkoxyphenyl-thio)ethyl]-N-nitrosoureas . The study of the cytotoxicity of the three N'-nitrosoureas, was carried out in two experimental models (P 388 and NSCLCN6).

A Survey of Exposure Level and Lifestyle Factors for Perfluorooctanoate and Perfluorooctane Sulfonate in Human Plasma from Selected Residents in Korea

PubMed Central

Eom, Jinhee; Choi, Jaeyeon; Kim, Jiye; Kim, Yunje

2014-01-01

Following few decades of commercial use, perfluorooctanoate (PFOA) and perfluorooctane sulfonate (PFOS) have been found in human blood and serum. We determined the amounts of PFOA and PFOS in human plasma (n = 183) and the effects of multiple uses of food-contact materials and smoking habits and alcohol consumption using liquid chromatography time-of-flight mass spectrometry (LC/TOF-MS). For the paper cups, the PFOA level in the plasma of the heavy user group was 1.37 times higher than that of the light user group. However, no association between the effects of multiple uses of food-contact materials and the plasma levels of PFOA and PFOS was found, except for paper cups. Active smokers had lower plasma levels of PFOA and PFOS than non-smokers. We show that multiple uses of food-contact materials do not appear to be a significant source of PFOA and PFOS. PMID:25032739

75 FR 58315 - Hazardous Waste Management System; Identification and Listing of Hazardous Waste; Direct Final...

Federal Register 2010, 2011, 2012, 2013, 2014

2010-09-24

... benzene, ethyl ether, methyl isobutyl ketone, n-butyl alcohol, cyclohexane, methanol. F005 Toluene, methyl... alcohol. U147 Maleic anhydride. U154 Methanol. U159 Methyl ethyl ketone. U161 Methyl isobutyl ketone. U213..., methyl isobutyl ketone, n-butyl alcohol, cyclohexane, methanol. F005 Toluene, methyl ethyl ketone, carbon...

Multicomponent Synthesis of a N-Protected Alpha-Amino Ester: Ethyl 2-((4-Methoxyphenyl)Amino)-3-Phenylpropanoate

ERIC Educational Resources Information Center

Le Gall, Erwan; Pignon, Antoine

2012-01-01

This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, "p"-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier…

Devopmental toxicity of perfluorooctane Sulfonate (PFOS) is not dependent on expression on peroxisome proliferator activated receptor-alpha (PPAR-alpha)in the mouse

EPA Science Inventory

Perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) are members of a family of perfluorinated compounds. Both are environmentally persistent and found in the serum of wildlife and humans. PFOS and PFOA are developmentally toxic in laboratory rodents. Exposure to t...

Perfluorooctane sulfonate plasma half-life determination and long term tissue distribution in beef cattle (Bos taurus)

USDA-ARS?s Scientific Manuscript database

Perfluorooctane sulfonate (PFOS) is used in consumer products as a surfactant and is found in industrial and consumer waste which ends up in wastewater treatment plants (WWTPs). PFOS does not breakdown during WWTP processes and accumulates in the biosolids. Common practices include application of bi...

EFFECTS OF PERFLUOROOCTANE SULFONATE (PFOS) ON MATERNAL AND DEVELOPMENTAL THYROID STATUS IN THE RAT

EPA Science Inventory

EFFECTS OF PERFLUOROOCTANE SULFONATE (PFOS) ON MATERNAL AND DEVELOPMENTAL THYROID STATUS IN THE RAT. JR Thibodeaux1, R Hanson1, B Grey1, JM Rogers1, ME Stanton2, and C Lau1. 1Reproductive Toxicology Division; 2Neurotoxicology Division, NHEERL, ORD, US EPA, Research Triangle P...

GENE EXPRESSION PROFILING IN WILD-TYPE AND PPARa-NULL MICE EXPOSED TO PERFLUOROOCTANE SULFONATE REVEALS PPARa-INDEPENDENT EFFECTS

EPA Science Inventory

Perfluorooctane sulfonate (PFOS) is a perfluoroalky1 acid (PFAA) and a persistent environmental contaminant found in the tissues of humans and wildlife. Although blood levels of PFOS have begun to decline, health concerns remain because of the long half-life of PFOS in humans. Li...

AROMATASE-B (CYP 19B) EXPRESSION IN FATHEAD MINNOWS (PIMEPHALES PROMELAS) EXPOSED TO PERFLUOROOCTANE (PFOS) AND THE AROMATASE INHIBITOR FADROZOLE

EPA Science Inventory

Perfluorooctane sulfonate (PFOS) is a fluorinated organic contaminant that is globally distributed in both humans and wildlife. PFOS belongs to a family of perfluorinated sulfonates that are highly persistent in the environment and have been commercially produced for over 40 year...

WINDOW OF SUSCEPTIBILITY TO PERFLUOROOCTANE SULFONATE (PFOS)-INDUCED NEONATAL MORTALITY IN THE RAT

EPA Science Inventory

GRASTY1, 2, R.C., B.E. GREY1, C.S. LAU1 and J.M. ROGERS1, 2. 1Reproductive Toxicology Division, NHEERL, ORD, US EPA, Research Triangle Park, NC; and 2Curriculum in Toxicology, UNC Chapel Hill, Chapel Hill, NC. Window of susceptibility to perfluorooctane sulfonate (PFOS)-induce...

Perfluoroalkyl substance contamination of the Llobregat River ecosystem (Mediterranean area, NE Spain).

PubMed

Campo, Julian; Pérez, Francisca; Masiá, Ana; Picó, Yolanda; Farré, Marinel la; Barceló, Damià

2015-01-15

The occurrence and sources of 21 perfluoroalkyl substances (PFASs: C4-C14, C16, C18 carboxylate, C4, C6-C8 and C10 sulfonates and C8 sulfonamide) were determined in water, sediment, and biota of the Llobregat River basin (NE Spain). Analytes were extracted by solid phase extraction (SPE) and determined by liquid chromatography triple quadrupole mass spectrometer (LC-QqQ-MS). All samples were contaminated with at least one PFAS, being the most frequently found perfluorobutanoate (PFBA), perfluorooctanoate (PFOA) and perfluorooctane sulfonate (L-PFOS). In general, mean PFAS concentrations measured in sediments (0.01-3.67 ng g(-1)) and biota (0.79-431 μg kg(-1)) samples were higher than those found in water (0.01-233 ng L(-1)). L-PFOS presented very high levels in biota and water, particularly in the Anoia River where a maximum concentration of 2.71 μg L(-1) was related to important industrial activities. However, this pollution does not extend down the Llobregat River according to cumulated values. None of the hazard quotients (HQ) calculated indicate potential risk for the different tropic levels considered (algae, Daphnia sp. and fish). According to Maximum Allowable Concentration (MAC) proposed by the European Commission (L-PFOS) and to Provisional Health Advisory (PHA) values (PFOA, L-PFOS) established by the United States Environmental Protection Agency (US EPA), only two water samples exceeded PHA concentration for L-PFOS. Copyright © 2014 Elsevier B.V. All rights reserved.

Temporal Shifts in Poly- and Perfluoroalkyl Substances (PFASs) in North Atlantic Pilot Whales Indicate Large Contribution of Atmospheric Precursors.

PubMed

Dassuncao, Clifton; Hu, Xindi C; Zhang, Xianming; Bossi, Rossana; Dam, Maria; Mikkelsen, Bjarni; Sunderland, Elsie M

2017-04-18

Poly- and perfluoroalkyl substances (PFASs) are persistent, bioaccumulative anthropogenic compounds associated with adverse health impacts on humans and wildlife. PFAS production changed in North America and Europe around the year 2000, but impacts on wildlife appear to vary across species and location. Unlike other mammal species, cetaceans lack the enzyme for transforming an important intermediate precursor (perfluorooctane sulfonamide: FOSA), into a prevalent compound in most wildlife (perfluorooctanesulfonate: PFOS). Thus, their tissue burden differentiates these two compounds while other mammals contain PFOS from both direct exposure and precursor degradation. Here we report temporal trends in 15 PFASs measured in muscle from juvenile male North Atlantic pilot whales (Globicephala melas) harvested between 1986 and 2013. FOSA accounted for a peak of 84% of the 15 PFASs around 2000 but declined to 34% in recent years. PFOS and long-chained PFCAs (C9-C13) increased significantly over the whole period (2.8% yr -1 to 8.3% yr -1 ), but FOSA declined by 13% yr -1 after 2006. Results from FOSA partitioning and bioaccumulation modeling forced by changes in atmospheric inputs reasonably capture magnitudes and temporal patterns in FOSA concentrations measured in pilot whales. Rapid changes in atmospheric FOSA in polar and subpolar regions around 2000 helps to explain large declines in PFOS exposure for species that metabolize FOSA, including seafood consuming human populations. This work reinforces the importance of accounting for biological exposures to PFAS precursors.

Perfluoroalkyl substances and extractable organic fluorine in surface sediments and cores from Lake Ontario.

PubMed

Yeung, Leo W Y; De Silva, Amila O; Loi, Eva I H; Marvin, Chris H; Taniyasu, Sachi; Yamashita, Nobuyoshi; Mabury, Scott A; Muir, Derek C G; Lam, Paul K S

2013-09-01

Fourteen perfluoroalkyl substances (PFASs) including short-chain perfluorocarboxylates (PFCAs, C4-C6) and perfluoroalkane sulfonates (PFSAs, C4 and C6) were measured in surface sediment samples from 26 stations collected in 2008 and sediment core samples from three stations (Niagara, Mississauga, and Rochester basins) collected in 2006 in Lake Ontario. Perfluorooctanesulfonate (PFOS), perfluorooctanoate (PFOA), perfluorononanoate (PFNA), perfluorodecanoate (PFDA), and perfluoroundecanoate (PFUnDA) were detected in all 26 surface sediment samples, whereas perfluorohexane sulfonate (PFHxS), perfluorooctane sulfonamide (FOSA), perfluorododecanoate (PFDoDA) and perfluorobutanoate (PFBA) were detected in over 70% of the surface sediment samples. PFOS was detected in all of the sediment core samples (range: 0.492-30.1ngg(-1) d.w.) over the period 1952-2005. The C8 to C11 PFCAs, FOSA, and PFBA increased in early 1970s. An overall increasing trend in sediment PFAS concentrations/fluxes from older to more recently deposited sediments was evident in the three sediment cores. The known PFCAs and PFSAs accounted for 2-44% of the anionic fraction of the extractable organic fluorine in surface sediment, suggesting that a large proportion of fluorine in this fraction remained unknown. Sediment core samples collected from Niagara basin showed an increase in unidentified organic fluorine in recent years (1995-2006). These results suggest that the use and manufacture of fluorinated organic compounds other than known PFCAs and PFSAs has diversified and increased. © 2013.

Prevalence of sulfonamide-resistant bacteria, resistance genes and integron-associated horizontal gene transfer in natural water bodies and soils adjacent to a swine feedlot in northern Taiwan.

PubMed

Hsu, Jih-Tay; Chen, Chia-Yang; Young, Chu-Wen; Chao, Wei-Liang; Li, Mao-Hao; Liu, Yung-Hsin; Lin, Chu-Ming; Ying, Chingwen

2014-07-30

Antibiotics are commonly used in swine feed to treat and prevent disease, as well as to promote growth. Antibiotics released into the environment via wastewater could accelerate the emergence of antibiotic-resistant bacteria and resistance genes in the surrounding environment. In this study, we quantified the occurrence of sulfonamides, sulfonamide-resistant microorganisms and resistance genes in the wastewater from a swine farm in northern Taiwan and its surrounding natural water bodies and soils. Sulfonamide levels were similar in the receiving downstream and upstream river water. However, the prevalence of sulfonamide-resistant bacteria and resistance genes, as analyzed by cultivation-dependent and -independent molecular approaches, was significantly greater in the downstream compared to the upstream river water samples. Barcoded-pyrosequencing revealed a highly diverse bacterial community structure in each sample. However, the sequence identity of the sulfonamide resistance gene sul1 in the wastewater and downstream environment samples was nearly identical (99-100%). The sul1 gene, which is genetically linked to class 1 integrons, was dominant in the downstream water bodies and soils. In conclusion, the increased prevalence of sulfonamide resistance genes in the wastewater from a swine farm, independent of the persistent presence of sulfonamides, could be a potential source of resistant gene pools in the surrounding environment. Copyright © 2014 Elsevier B.V. All rights reserved.

Determination of Sulfonamide Residues in Food by Capillary Zone Electrophoresis with On-Line Chemiluminescence Detection Based on an Ag(III) Complex.

PubMed

Dai, Tingting; Duan, Jie; Li, Xinghua; Xu, Xiangdong; Shi, Hongmei; Kang, Weijun

2017-06-16

The presence of sulfonamide (SA) residues in foods is largely due to the raising of animals with sulfonamide antibiotics added or polluted feedstuff. In this paper, a sensitive method was developed for the determination of the residues of three sulfonamides in animal-derived food; the SAs include sulfadimidine (SDD), sulfadiazine (SDZ), and sulfathiazole (STZ). The method is based on capillary zone electrophoresis (CE) with online chemiluminescence (CL) detection, using an Ag(III) complex as an oxidant. These SAs have an inhibiting effect on the Ag(III)-luminol CL reaction. The electrophoretic buffer is 12.0 mM sodium borate. Under a set of optimized conditions, the linear ranges for the detections were found to be 10.0-200 µg·mL -1 for SDD and SDZ, and 2.0-50.0 µg·mL -1 for STZ. The detection limits were 2.75, 3.14, and 0.65 µg·mL -1 for SDD, SDZ, and STZ, respectively. Relative standard deviations (RSD) for the peak heights were between 2.1% and 2.8% (n = 7). The proposed method was used in the analysis of the SAs in samples from pork meat, chicken meat, and milk, showing satisfactory detection results. A reaction mechanism was also proposed for the Ag(III)-luminol-SA CL reactions. The method has potential applications for the monitoring of residue levels of the three SAs in food, providing food safety data.

Why sulfonamides are contraindicated in Rocky Mountain spotted fever.

PubMed

Ren, Vicky; Hsu, Sylvia

2014-02-18

Sulfonamide antibiotics are not effective for the treatment of Rocky Mountain spotted fever (RMSF). Patients suspected of having RMSF based on history and physical exam should be treated with doxycycline and not a sulfonamide to avoid increased morbidity and mortality.

[4-t-butylphenyl]-N-(4-imidazol-1-yl phenyl)sulfonamide (ISCK03) inhibits SCF/c-kit signaling in 501mel human melanoma cells and abolishes melanin production in mice and brownish guinea pigs.

PubMed

Na, Yong Joo; Baek, Heung Su; Ahn, Soo Mi; Shin, Hyun Jung; Chang, Ih-Seop; Hwang, Jae Sung

2007-09-01

It is well known that c-kit is related to pigmentation as well as to the oncology target protein. The objective of this study was to discover a skin-whitening agent that regulates c-kit activity. We have developed a high-throughput screening system using recombinant human c-kit protein. Approximately 10,000 synthetic compounds were screened for their effect on c-kit activity. Phenyl-imidazole sulfonamide derivatives showed inhibitory activity on c-kit phosphorylation in vitro. The effects of one derivative, [4-t-butylphenyl]-N-(4-imidazol-1-yl phenyl)sulfonamide (ISCK03), on stem-cell factor (SCF)/c-kit cellular signaling in 501mel human melanoma cells were examined further. Pretreatment of 501mel cells with ISCK03 inhibited SCF-induced c-kit phosphorylation dose dependently. ISCK03 also inhibited p44/42 ERK mitogen-activated protein kinase (MAPK) phosphorylation, which is known to be involved in SCF/c-kit downstream signaling. However ISCK03 did not inhibit hepatocyte growth factor (HGF)-induced phosphorylation of p44/42 ERK proteins. To determine the in vivo potency of ISCK03, it was orally administered to depilated C57BL/6 mice. Interestingly, oral administration of ISCK03 induced the dose-dependent depigmentation of newly regrown hair, and this was reversed with cessation of ISCK03 treatment. Finally, to investigate whether the inhibitory effect of ISCK03 on SCF/c-kit signaling abolished UV-induced pigmentation, ISCK03 was applied to UV-induced pigmented spots on brownish guinea pig skin. The topical application of ISCK03 promoted the depigmentation of UV-induced hyperpigmented spots. Fontana-Masson staining analysis showed epidermal melanin was diminished in spots treated with ISCK03. These results indicate that phenyl-imidazole sulfonamide derivatives are potent c-kit inhibitors and might be used as skin-whitening agents.

4-Meth-oxy-N-(1-methyl-1H-indazol-5-yl)benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Geffken, Detlef; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

The indazole ring system [maximum deviation = 0.013 (2) Å] of the title compound, C15H15N3O3S, makes a dihedral angle of 50.11 (7)° with the benzene ring. In the crystal, cohesion is provided by C-H⋯O and N-H⋯N hydrogen bonds, which link the molecules into chains propagating along the b-axis direction.

Enhanced removal of sulfonamide antibiotics by KOH-activated anthracite coal: Batch and fixed-bed studies.

PubMed

Zuo, Linzi; Ai, Jing; Fu, Heyun; Chen, Wei; Zheng, Shourong; Xu, Zhaoyi; Zhu, Dongqiang

2016-04-01

The presence of sulfonamide antibiotics in aquatic environments poses potential risks to human health and ecosystems. In the present study, a highly porous activated carbon was prepared by KOH activation of an anthracite coal (Anth-KOH), and its adsorption properties toward two sulfonamides (sulfamethoxazole and sulfapyridine) and three smaller-sized monoaromatics (phenol, 4-nitrophenol and 1,3-dinitrobenzene) were examined in both batch and fixed-bed adsorption experiments to probe the interplay between adsorbate molecular size and adsorbent pore structure. A commercial powder microporous activated carbon (PAC) and a commercial mesoporous carbon (CMK-3) possessing distinct pore properties were included as comparative adsorbents. Among the three adsorbents Anth-KOH exhibited the largest adsorption capacities for all test adsorbates (especially the two sulfonamides) in both batch mode and fixed-bed mode. After being normalized by the adsorbent surface area, the batch adsorption isotherms of sulfonamides on PAC and Anth-KOH were displaced upward relative to the isotherms on CMK-3, likely due to the micropore-filling effect facilitated by the microporosity of adsorbents. In the fixed-bed mode, the surface area-normalized adsorption capacities of Anth-KOH for sulfonamides were close to that of CMK-3, and higher than that of PAC. The irregular, closed micropores of PAC might impede the diffusion of the relatively large-sized sulfonamide molecules and in turn led to lowered fixed-bed adsorption capacities. The overall superior adsorption of sulfonamides on Anth-KOH can be attributed to its large specific surface area (2514 m(2)/g), high pore volume (1.23 cm(3)/g) and large micropore sizes (centered at 2.0 nm). These findings imply that KOH-activated anthracite coal is a promising adsorbent for the removal of sulfonamide antibiotics from aqueous solution. Copyright © 2016 Elsevier Ltd. All rights reserved.

40 CFR 721.5625 - Oxiranemethanamine, N,N′-[methylenebis(2-ethyl-4,1-phenylene)]bis[N-(oxiranylmethyl)]-.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Oxiranemethanamine, N,Nâ²-[methylenebis(2-ethyl-4,1-phenylene)]bis[N-(oxiranylmethyl)]-. 721.5625 Section 721.5625 Protection of... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5625 Oxiranemethanamine, N...

40 CFR 721.5625 - Oxiranemethanamine, N,N′-[methylenebis(2-ethyl-4,1-phenylene)]bis[N-(oxiranylmethyl)]-.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Oxiranemethanamine, N,Nâ²-[methylenebis(2-ethyl-4,1-phenylene)]bis[N-(oxiranylmethyl)]-. 721.5625 Section 721.5625 Protection of... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5625 Oxiranemethanamine, N...

Chloridobis(ethyl­enediamine-κ2 N,N′)(n-pentyl­amine-κN)cobalt(III) dichloride monhydrate

PubMed Central

Anbalagan, K.; Tamilselvan, M.; Nirmala, S.; Sudha, L.

2009-01-01

The title complex, [CoCl(C5H13N)(C2H8N2)2]Cl2·H2O, comprises one chloridobis(ethyl­enediamine)(n-pentyl­amine)cobalt(III) cation, two chloride counter-anions and a water mol­ecule. The CoIII atom of the complex is hexa­coordinated by five N and one Cl atoms. The five N atoms are from two chelating ethyl­enediamine and one n-pentyl­amine ligands. Neighbouring cations and anions are connected by N—H⋯Cl and N—H⋯O hydrogen bonds to each other and also to the water mol­ecule. PMID:21582753

Perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) risk to beef consumers Part II: Adsorption, distribution, metabolism, and excretion studies for improving risk evaluations

USDA-ARS?s Scientific Manuscript database

Perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) are industrially produced chemicals used as surfactants and coatings in many industrial, commercial and consumer products. These compounds are ubiquitous in humans and the environment. PFOA and PFOS have been observed in biosolids fr...

[Interaction Between Sulfonamide Antibiotics Fates and Chicken Manure Composting].

PubMed

Lin, Hui; Wang, Jian-mei; Sun, Wan-chun; Fu, Jian-rong; Chen, Hong-jin; Ma, Jun-wei

2016-05-15

Based on aerobic manure composting with or without the addition of a mixture of sulfadimethoxine SM2 and sulfamonomethoxine SMM (1:1, m/m), changes in the physic-chemical properties of manure compost, the microbial community physiological profiles, the antibiotics concentration and the abundances of five antibiotic resistance genes (ARGs) during the composting were tracked. The results indicated that the introduction of sulfonamide antibiotics led to inhibition on the basal respiration of manure compost during the early composting period, delayed the formation of thermophilic temperature and reduced the conversion of nutrients such as organic matter, ammonia nitrogen and nitrate nitrogen. Meanwhile, the introduction of sulfonamide antibiotics dramatically affected the physiological profile of microbial community in manure in the middle stage of composting. HPLC-MS/MS results showed that both SMM and SM2 in manure were completely degraded within 14 days, while the degradation rate of SMM was faster than that of SM2. For both composting treatments with or without addition of exogenous antibiotics, the relative abundance of sull and sul2 showed an initial decline in the first 14 or 21 days and a slight increase thereafter. The addition of exogenous antibiotics showed insignificant enhancement on increasing the relative abundance of sul1 and IntI1 in manure, but resulted in an apparent increase in sul2 relative abundance. Although the fates of tetQ and tetW during composting were different from that of sulfonamide ARGs, the introduction of sulfonamide antibiotics into manure increased the relative abundance of tetracycline ARGs. Redundancy analysis indicated that composting temperature correlated negatively with sul1, sul2 and IntI1 relative abundance in manure but had no obvious relationship with tetQ and tetW relative abundance. All the ARGs detected in this work correlated negatively with C/N ratio and the nitrate nitrogen concentration of manure compost but positively correlated with pH, moisture and ammonia nitrogen concentration of manure compost.

[(S)-1-Carbamoylethyl]bis(dimethylglyoximato-kappa2N,N')[(S)-1-phenylethylamine]cobalt(III) and bis(dimethylglyoximato-kappa2N,N')[(R)-1-(N-methylcarbamoyl)ethyl][(R)-1-phenylethylamine]cobalt(III) monohydrate.

PubMed

Orisaku, Keiko Komori; Hagiwara, Mieko; Ohgo, Yoshiki; Arai, Yoshifusa; Ohgo, Yoshiaki

2005-04-01

The title complexes, [Co(C3H6NO)(C4H7N2O2)2(C8H11N)] and [Co(C4H8NO)(C4H7N2O2)2(C8H11N)].H2O, were resolved from [(RS)-1-carbamoylethyl]bis(dimethylglyoximato)[(S)-1-phenylethylamine]cobalt(III) and bis(dimethylglyoximato)[(RS)-1-(N-methylcarbamoyl)ethyl][(R)-1-phenylethylamine]cobalt(III), respectively, and their crystal structures were determined in order to reveal the absolute configuration of the major enantiomer produced in the photoisomerization of each series of 2-carbamoylethyl and 2-(N-methylcarbamoyl)ethyl cobaloxime complexes.

Open saccharin-based secondary sulfonamides as potent and selective inhibitors of cancer-related carbonic anhydrase IX and XII isoforms.

PubMed

D'Ascenzio, Melissa; Guglielmi, Paolo; Carradori, Simone; Secci, Daniela; Florio, Rosalba; Mollica, Adriano; Ceruso, Mariangela; Akdemir, Atilla; Sobolev, Anatoly P; Supuran, Claudiu T

2017-12-01

A large number of novel secondary sulfonamides based on the open saccharin scaffold were synthesized and evaluated as selective inhibitors of four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). They were obtained by reductive ring opening of the newly synthesized N-alkylated saccharin derivatives and were shown to be inactive against the two cytosolic off-target hCA I and II (K i s > 10 µM). Interestingly, these compounds inhibited hCA IX in the low nanomolar range with K i s ranging between 20 and 298 nM and were extremely potent inhibitors of hCA XII isoenzyme (K i s ranging between 4.3 and 432 nM). Since hCA IX and XII are the cancer-related isoforms recently validated as drug targets, these results represent an important goal in the development of new anticancer candidates. Finally, a computational approach has been performed to better correlate the biological data to the binding mode of these inhibitors.

N-[2-(5-Bromo-2-morpholin-4-ylpyrim­idin-4-ylsulfan­yl)-4-meth­oxy­phen­yl]-2,4,6-trimethyl­benzene­sulfonamide

PubMed Central

Kumar, Mohan; Mallesha, L.; Sridhar, M. A.; Kapoor, Kamini; Gupta, Vivek K.; Kant, Rajni

2012-01-01

In the title compound, C24H27BrN4O4S2, the mol­ecule is twisted at the sulfonyl S atom with a C—S(O2)—N(H)—C torsion angle of 62.6 (3)°. The benzene rings bridged by the sulfonamide group are tilted to each other by a dihedral angle of 60.6 (1)°. The dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 62.7 (1)°. The morpholine ring adopts a chair conformation. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 2,4,6-trimethyl­benzene rings [centroid–centroid distance = 3.793 (2) Å]. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into a chain along the b axis. PMID:23284396

N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

PubMed Central

Kant, Rajni; Gupta, Vivek K.; Kapoor, Kamini; Kumar, Mohan; Mallesha, L.; Sridhar, M. A.

2012-01-01

In the title compound, C22H23BrN4O4S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 68.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.7 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 4-methylbenzene rings [centroid–centroid distance = 3.934 (2) Å]. The morpholine ring adopts a chair conformation and is disordered over two positions with an occupancy ratio of 0.853 (6):0.147 (6). In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into chains extending along the a axis and further, through C—H⋯N and C—H⋯O inter­actions, into a three-dimensional supramolecular structure. PMID:22905015

Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies

NASA Astrophysics Data System (ADS)

Boufas, Wahida; Dupont, Nathalie; Berredjem, Malika; Berrezag, Kamel; Becheker, Imène; Berredjem, Hajira; Aouf, Nour-Eddine

2014-09-01

A series of substituted sulfonamide derivatives were synthesized from chlorosulfonyl isocyanate (CSI) in tree steps (carbamoylation, sulfamoylation and deprotection). Antibacterial activity in vitro of some newly formed compounds investigated against clinical strains Gram-positive and Gram-negative: Escherichia coli and Staphylococcus aureus applying the method of dilution and minimal inhibition concentration (MIC) methods. These compounds have significant bacteriostatic activity with totalities of bacterial strains used. DFT calculations with B3LYP/6-31G(d) level have been used to analyze the electronic and geometric characteristics deduced for the stable structure of three compounds presenting conjugation between a nitrogen atom N through its lone pair and an aromatic ring next to it. The principal quantum chemical descriptors have been correlated with the antibacterial activity.

Synthesis and description of intermolecular interactions in new sulfonamide derivatives of tranexamic acid

NASA Astrophysics Data System (ADS)

Ashfaq, Muhammad; Arshad, Muhammad Nadeem; Danish, Muhammad; Asiri, Abdullah M.; Khatoon, Sadia; Mustafa, Ghulam; Zolotarev, Pavel N.; Butt, Rabia Ayub; Şahin, Onur

2016-01-01

Tranexamic acid (4-aminomethyl-cyclohexanecarboxylic acid) was reacted with sulfonyl chlorides to produce structurally related four sulfonamide derivatives using simple and environmental friendly method to check out their three-dimensional behavior and van der Walls interactions. The molecules were crystallized in different possibilities, as it is/after alkylation at its O and N atoms/along with a co-molecule. All molecules were crystallized in monoclinic crystal system with space group P21/n, P21/c and P21/a. X-ray studies reveal that the molecules stabilized themselves by different kinds of hydrogen bonding interactions. The molecules are getting connected through O-H⋯O hydrogen bonds to form inversion dimers which are further connected through N-H⋯O interactions. The molecules in which N and O atoms were alkylated showed non-classical interaction and generated centro-symmetric R22(24) ring motif. The co-crystallized host and guest molecules are connected to each other via O-H⋯O interactions to generate different ring motifs. By means of the ToposPro software an analysis of the topologies of underlying nets that correspond to molecular packings and hydrogen-bonded networks in structures under consideration was carried out.

Intrinsic thermodynamics of inhibitor binding to human carbonic anhydrase IX.

PubMed

Linkuvienė, Vaida; Matulienė, Jurgita; Juozapaitienė, Vaida; Michailovienė, Vilma; Jachno, Jelena; Matulis, Daumantas

2016-04-01

Human carbonic anhydrase 9th isoform (CA IX) is an important marker of numerous cancers and is increasingly interesting as a potential anticancer drug target. Various synthetic aromatic sulfonamide-bearing compounds are being designed as potent inhibitors of CA IX. However, sulfonamide compound binding to CA IX is linked to several reactions, the deprotonation of the sulfonamide amino group and the protonation of the CA active site Zn(II)-bound hydroxide. These linked reactions significantly affect the affinities and other thermodynamic parameters such as enthalpies and entropies of binding. The observed and intrinsic affinities of compound binding to CA IX were determined by the fluorescent thermal shift assay. The enthalpies and entropies of binding were determined by the isothermal titration calorimetry. The pKa of CA IX was determined to be 6.8 and the enthalpy of CA IX-Zn(II)-bound hydroxide protonation was -24 kJ/mol. These values enabled the analysis of intrinsic thermodynamics of a library of compounds binding to CA IX. The most strongly binding compounds exhibited the intrinsic affinity of 0.01 nM and the observed affinity of 2 nM. The intrinsic thermodynamic parameters of compound binding to CA IX helped to draw the compound structure to thermodynamics relationship. It is important to distinguish the intrinsic from observed parameters of any disease target protein interaction with its inhibitors as drug candidates when drawing detailed compound structure to thermodynamics correlations. Copyright © 2016 Elsevier B.V. All rights reserved.

Determination of six sulfonamide antibiotics, two metabolites and trimethoprim in wastewater by isotope dilution liquid chromatography/tandem mass spectrometry.

PubMed

Le-Minh, Nhat; Stuetz, Richard M; Khan, Stuart J

2012-01-30

A highly sensitive method for the analysis of six sulfonamide antibiotics (sulfadiazine, sulfathiazole, sulfapyridine, sulfamerazine, sulfamethazine and sulfamethoxazole), two sulfonamide metabolites (N(4)-acetyl sulfamethazine and N(4)-acetyl sulfamethoxazole) and the commonly co-applied antibiotic trimethoprim was developed for the analysis of complex wastewater samples. The method involves solid phase extraction of filtered wastewater samples followed by liquid chromatography-tandem mass spectral detection. Method detection limits were shown to be matrix-dependent but ranged between 0.2 and 0.4 ng/mL for ultrapure water, 0.4 and 0.7 ng/mL for tap water, 1.4 and 5.9 ng/mL for a laboratory-scale membrane bioreactor (MBR) mixed liquor, 0.7 and 1.7 ng/mL for biologically treated effluent and 0.5 and 1.5 ng/g dry weight for MBR activated sludge. An investigation of analytical matrix effects was undertaken, demonstrating the significant and largely unpredictable nature of signal suppression observed for variably complex matrices compared to an ultrapure water matrix. The results demonstrate the importance of accounting for such matrix effects for accurate quantitation, as done in the presented method by isotope dilution. Comprehensive validation of calibration linearity, reproducibility, extraction recovery, limits of detection and quantification are also presented. Finally, wastewater samples from a variety of treatment stages in a full-scale wastewater treatment plant were analysed to illustrate the effectiveness of the method. Copyright © 2011 Elsevier B.V. All rights reserved.

40 CFR 721.1850 - Toluene sulfonamide bis-phe-nol A epoxy adduct.

Code of Federal Regulations, 2014 CFR

2014-07-01

... epoxy adduct. 721.1850 Section 721.1850 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1850 Toluene sulfonamide bis-phe-nol A epoxy adduct. (a) Chemical... as toluene sulfonamide bisphenol A epoxy adduct (PMN P-90-113) is subject to reporting under this...

40 CFR 721.1850 - Toluene sulfonamide bis-phe-nol A epoxy adduct.

Code of Federal Regulations, 2012 CFR

2012-07-01

... epoxy adduct. 721.1850 Section 721.1850 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1850 Toluene sulfonamide bis-phe-nol A epoxy adduct. (a) Chemical... as toluene sulfonamide bisphenol A epoxy adduct (PMN P-90-113) is subject to reporting under this...

40 CFR 721.1850 - Toluene sulfonamide bis-phe-nol A epoxy adduct.

Code of Federal Regulations, 2013 CFR

2013-07-01

... epoxy adduct. 721.1850 Section 721.1850 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1850 Toluene sulfonamide bis-phe-nol A epoxy adduct. (a) Chemical... as toluene sulfonamide bisphenol A epoxy adduct (PMN P-90-113) is subject to reporting under this...

40 CFR 721.1850 - Toluene sulfonamide bis-phe-nol A epoxy adduct.

Code of Federal Regulations, 2011 CFR

2011-07-01

... epoxy adduct. 721.1850 Section 721.1850 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1850 Toluene sulfonamide bis-phe-nol A epoxy adduct. (a) Chemical... as toluene sulfonamide bisphenol A epoxy adduct (PMN P-90-113) is subject to reporting under this...

Inhibition by sulfonamides of the candidacidal activity of human neutrophils.

PubMed

Lehrer, R I

1971-12-01

Sulfonamides reduced substantially the ability of normal human neutrophils to kill strains of Candida albicans and Candida tropicalis, and impaired to a lesser extent their activity against Staphylococcus aureus 502A and Serratia marcescens. Sulfonamides also inhibited (a) iodination of Candida cells by normal neutrophils; (b) candidacidal activity in cell-free systems containing purified human myeloperoxidase, hydrogen peroxide, and potassium iodide; and (c) accumulation of molecular iodine in analogously constructed cell-free systems. In contrast to these effects on reactions catalyzed by myeloperoxidase, sulfonamides exerted relatively little effect on the levels of microbicidal activity manifested by human neutrophils that lacked myeloperoxidase. Sulfonamides appear to influence the function of human neutrophils predominantly by interfering with myeloperoxidase-mediated pathways. Certain basic and clinical implications of these data are discussed.

Analyses of sulfonamide antibiotics by a successive anion- and cation-selective injection coupled to microemulsion electrokinetic chromatography.

PubMed

Lin, Yun-Ta; Liu, Yu-Wei; Cheng, Yi-Jie; Huang, Hsi-Ya

2010-07-01

In this study, an MEEKC was used to detect and analyze nine sulfonamide antibiotics. Owing to an insufficient sensitivity of on-column UV detection, a field-amplified sample injection, successive anion- and cation-selective injection, was used for the on-line concentration of the nine antibiotics. In the successive anion- and cation-selective injection mode, a leading water plug was introduced prior to anion injection, and then an acidic plug followed by a terminal water plug had to be used before subsequent cation injection. The results indicated some sulfonamides (sulfamonomethoxine, sulfamethazine, sulfamerazine and sulfadiazine) were determined as split signals in pairs, and this was likely due to the use of a longer acid plug (360 s) which caused the sulfonamide anions and cations to be stacked in two distinct zones of the leading water and acid plugs. Meanwhile, all the sulfonamides that were introduced either by anion or cation injection were stacked within the leading water plug when a shorter acid plug (210 s) was used. As a result, the nine sulfonamides were determined as single and symmetrical peaks with low LODs (0.9-4.2 microg/L). Furthermore, the MEEKC method was successfully applied for the detection of trace sulfonamide residues in several food and water samples.

MATERNAL AND DEVELOPMENTAL TOXICITY OF PERFLUOROOCTANE SULFONATE (PFOS) IN THE MOUSE

EPA Science Inventory

MATERNAL AND DEVELOPMENTAL TOXICITY OF PERFLUOROOCTANE SULFONATE (PFOS) IN THE MOUSE. J.R. Thibodeaux1, R.G. Hanson1, B.E. Grey1, B.D. Barbee1, J.H. Richards2, J.L. Butenhoff3, J.M. Rogers1, C. Lau1. 1Reprod. Tox. Div., 2Exp. Tox. Div., NHEERL, ORD, US EPA, Research Triangle Pa...

Exposure to perfluorooctane sulfonate during pregnancy in rat and mouse. II: postnatal evaluation

EPA Science Inventory

The postnatal effects of in utero exposure to perfluorooctane sulfonate (PFOS, C8F17SO3-) were evaluated in the rat and mouse. Pregnant Sprague-Dawley rats were given 1, 2, 3, 5, or 10 mg/kg PFOS daily by gavage from gestation day (GD) 2 to GD 21; pregnant CD-1 mice were treated ...

Prevalence and characterization of plasmids carrying sulfonamide resistance genes among Escherichia coli from pigs, pig carcasses and human.

PubMed

Wu, Shuyu; Dalsgaard, Anders; Hammerum, Anette M; Porsbo, Lone J; Jensen, Lars B

2010-07-30

Sulfonamide resistance is very common in Escherichia coli. The aim of this study was to characterize plasmids carrying sulfonamide resistance genes (sul1, sul2 and sul3) in E. coli isolated from pigs and humans with a specific objective to assess the genetic diversity of plasmids involved in the mobility of sul genes. A total of 501 E. coli isolates from pig feces, pig carcasses and human stools were tested for their susceptibility to selected antimicrobial. Multiplex PCR was conducted to detect the presence of three sul genes among the sulfonamide-resistant E. coli isolates. Fifty-seven sulfonamide-resistant E. coli were selected based on presence of sul resistance genes and subjected to conjugation and/or transformation experiments. S1 nuclease digestion followed by pulsed-field gel electrophoresis was used to visualize and determine the size of plasmids. Plasmids carrying sul genes were characterized by PCR-based replicon typing to allow a comparison of the types of sul genes, the reservoir and plasmid present. A total of 109/501 isolates exhibited sulfonamide resistance. The relative prevalences of sul genes from the three reservoirs (pigs, pig carcasses and humans) were 65%, 45% and 12% for sul2, sul1, and sul3, respectively. Transfer of resistance through conjugation was observed in 42/57 isolates. Resistances to streptomycin, ampicillin and trimethoprim were co-transferred in most strains. Class 1 integrons were present in 80% of sul1-carrying plasmids and 100% of sul3-carrying plasmids, but only in 5% of sul2-carrying plasmids. The sul plasmids ranged from 33 to 160-kb in size and belonged to nine different incompatibility (Inc) groups: FII, FIB, I1, FIA, B/O, FIC, N, HI1 and X1. IncFII was the dominant type in sul2-carrying plasmids (52%), while IncI1 was the most common type in sul1 and sul3-carrying plasmids (33% and 45%, respectively). Multireplicons were found associated with all three sul genes. Sul genes were distributed widely in E. coli isolated from pigs and humans with sul2 being most prevalent. Sul-carrying plasmids belonged to diverse replicon types, but most of detected plasmids were conjugative enabling horizontal transfer. IncFII seems to be the dominant replicon type in sul2-carrying plasmids from all three sources.

Novel 3-Nitro-1H-1,2,4-triazole-based Amides and Sulfonamides as Potential anti-Trypanosomal Agents

PubMed Central

Papadopoulou, Maria V.; Bloomer, William D.; Rosenzweig, Howard S.; Chatelain, Eric; Kaiser, Marcel; Wilkinson, Shane R.; McKenzie, Caroline; Ioset, Jean-Robert

2012-01-01

A series of novel 3-nitro-1H-1,2,4-triazole-(and in some cases 2-nitro-1H-imidazole)-based amides and sulfonamides were characterized for their in vitro anti-trypanosomal and antileishmanial activities as well as mammalian toxicity. Out of 36 compounds tested, 29 (mostly 3-nitro-1H-1,2,4-triazoles) displayed significant activity against T. cruzi intracellular amastigotes (IC50 ranging from 28 nM to 3.72 μM) without concomitant toxicity to L6 host cells (selectivity 66 to 2782). Twenty three of these active compounds were more potent (up to 58 fold) than the reference drug benznidazole, tested in parallel. In addition, 9 nitrotriazoles which were moderately active (0.5 μM ≤ IC50 < 6.0 μM) against T. b. rhodesiense trypomastigotes, were 5 to 31 fold more active against bloodstream-form T. b. brucei trypomastigotes engineered to overexpress NADH-dependent nitroreductase (TbNTR). Finally, 3 nitrotriazoles displayed a moderate activity against the axenic form of Leishmania donovani. Therefore, 3-nitro-1H-1,2,4-triazole-based amides and sulfonamides are potent anti-trypanosomal agents. PMID:22550999

Electron Spin Resonance Studies of Carbonic Anhydrase: Transition Metal Ions and Spin-Labeled Sulfonamides*

PubMed Central

Taylor, June S.; Mushak, Paul; Coleman, Joseph E.

1970-01-01

Electron spin resonance (esr) spectra of Cu(II) and Co(II) carbonic anhydrase, and a spin-labeled sulfonamide complex of the Zn(II) enzyme, are reported. The coordination geometry of Cu(II) bound in the enzyme appears to have approximately axial symmetry. Esr spectra of enzyme complexes with metal-binding anions also show axial symmetry and greater covalency, in the order ethoxzolamide < SH- < N3- ≤ CN-. Well-resolved superhyperfine structure in the spectrum of the cyanide complex suggests the presence of two, and probably three, equivalent nitrogen ligands from the protein. Esr spectra of the Co(II) enzyme and its complexes show two types of Co(II) environment, one typical of the native enzyme and the 1:1 CN- complex, and one typical of a 2:1 CN- complex. Co(II) in the 2:1 complex appears to be low-spin and probably has a coordination number of 5. Binding of a spin-labeled sulfonamide to the active center immobilizes the free radical. The similarity of the esr spectra of spin-labeled Zn(II) and Co(II) carbonic anhydrases suggests that the conformation at the active center is similar in the two metal derivatives. PMID:4320976

Nitrotriazole- and imidazole-based amides and sulfonamides as antitubercular agents.

PubMed

Papadopoulou, Maria V; Bloomer, William D; Rosenzweig, Howard S; Arena, Alexander; Arrieta, Francisco; Rebolledo, Joseph C J; Smith, Diane K

2014-11-01

Twenty-three 3-nitrotriazole-based and 2-nitroimidazole-based amides and sulfonamides were screened for antitubercular (anti-TB) activity in aerobic Mycobacterium tuberculosis H37Rv by using the BacTiter-Glo (BTG) microbial cell viability assay. In general, 3-nitrotriazole-based sulfonamides demonstrated anti-TB activity, whereas 3-nitrotriazole-based amides and 2-nitroimidazole-based amides and sulfonamides were inactive. Three 3-nitrotriazole-based sulfonamides (compounds 4, 2, and 7) demonstrated 50% inhibitory concentration (IC50), IC90, and MIC values of 0.38, 0.43, and 1.56 μM (compound 4), 0.57, 0.98, and 3.13 μM (compound 2), and 0.79, 0.87, and 3.13 μM (compound 7), respectively. For 3-nitrotriazole-based sulfonamides, anti-TB activity increased with lipophilicity, whereas the one-electron reduction potential (E1/2) did not play a role. 2-Nitroimidazole-based analogs, which were inactive in the BTG assay, were significantly more active in the low-oxygen assay and more active than the 3-nitrotriazoles. All active nitrotriazoles in the BTG assay were similarly active or more potent (lower MIC values) against resistant strains, with the exception of compounds 2, 3, 4, and 8, which demonstrated greater MIC values against isoniazid-resistant strains. Five 3-nitrotriazole-based sulfonamides demonstrated activity in infected murine J774 macrophages, causing log reductions similar to those seen with rifampin. However, some compounds caused toxicity in uninfected macrophages. In conclusion, the classes of 3-nitrotriazole-based amides and sulfonamides merit further investigation as potential antitubercular agents. Copyright © 2014, American Society for Microbiology. All Rights Reserved.

Nitrotriazole- and Imidazole-Based Amides and Sulfonamides as Antitubercular Agents

PubMed Central

Bloomer, William D.; Rosenzweig, Howard S.; Arena, Alexander; Arrieta, Francisco; Rebolledo, Joseph C. J.; Smith, Diane K.

2014-01-01

Twenty-three 3-nitrotriazole-based and 2-nitroimidazole-based amides and sulfonamides were screened for antitubercular (anti-TB) activity in aerobic Mycobacterium tuberculosis H37Rv by using the BacTiter-Glo (BTG) microbial cell viability assay. In general, 3-nitrotriazole-based sulfonamides demonstrated anti-TB activity, whereas 3-nitrotriazole-based amides and 2-nitroimidazole-based amides and sulfonamides were inactive. Three 3-nitrotriazole-based sulfonamides (compounds 4, 2, and 7) demonstrated 50% inhibitory concentration (IC50), IC90, and MIC values of 0.38, 0.43, and 1.56 μM (compound 4), 0.57, 0.98, and 3.13 μM (compound 2), and 0.79, 0.87, and 3.13 μM (compound 7), respectively. For 3-nitrotriazole-based sulfonamides, anti-TB activity increased with lipophilicity, whereas the one-electron reduction potential (E1/2) did not play a role. 2-Nitroimidazole-based analogs, which were inactive in the BTG assay, were significantly more active in the low-oxygen assay and more active than the 3-nitrotriazoles. All active nitrotriazoles in the BTG assay were similarly active or more potent (lower MIC values) against resistant strains, with the exception of compounds 2, 3, 4, and 8, which demonstrated greater MIC values against isoniazid-resistant strains. Five 3-nitrotriazole-based sulfonamides demonstrated activity in infected murine J774 macrophages, causing log reductions similar to those seen with rifampin. However, some compounds caused toxicity in uninfected macrophages. In conclusion, the classes of 3-nitrotriazole-based amides and sulfonamides merit further investigation as potential antitubercular agents. PMID:25182645

Sulfonamides as Inhibitors of Leishmania – Potential New Treatments for Leishmaniasis

PubMed Central

Katinas, Jade; Epplin, Rachel; Hamaker, Christopher; Jones, Marjorie A.

2017-01-01

Introduction: Leishmaniasis is an endemic disease caused by the protozoan parasite Leishmania. Current treatments for the parasite are limited by cost, availability and drug resistance as the occurrence of leishmaniasis continues to be more prevalent. Sulfonamides are a class of compounds with medicinal properties which have been used to treat bacterial and parasitic disease via various pathways especially as antimetabolites for folic acid. Methods: New derivatives of sulfonamide compounds were assessed for their impact on Leishmania cell viability and potential pathways for inhibition were evaluated. Leishmania tarentolae (ATCC Strain 30143) axenic promastigote cells were grown in brain heart infusion (BHI) medium and treated with varying concentrations of the new sulfonamide compounds. Light microscopy and viability tests were used to assess the cells with and without treatment. Discussion: A non-water soluble sulfonamide was determined to have 90-96% viability inhibition 24 hours after treatment with 100 µM final concentration. Because Leishmania are also autotrophs for folate precursors, the folic acid pathway was identified as a target for sulfonamide inhibition. When folic acid was added to untreated Leishmania, cell proliferation increased. A water soluble derivative of the inhibitory sulfonamide was synthesized and evaluated, resulting in less viability inhibition with a single dose (approximately 70% viability inhibition after 24 hours with 100 µM final concentration), but additive inhibition with multiple doses of the compound. Results: However, the potential mechanism of inhibition was different between the water-soluble and non-water soluble sulfonamides. The inhibitory effects and potential pathways of inhibition indicate that these compounds may be new treatments for this disease. PMID:29399442

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-2,4,6-trimethyl­benzene­sulfonamide

PubMed Central

Kumar, Mohan; Mallesha, L.; Sridhar, M. A.; Kapoor, Kamini; Gupta, Vivek K.; Kant, Rajni

2012-01-01

In the title compound, C25H29BrN4O3S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 63.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 64.9 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 2,4,6-trimethyl­benzene rings [centroid–centroid distance = 3.766 (2) Å]. The piperidine ring adopts a chair conformation. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds and these dimers are further linked by C—H⋯O hydrogen bonds into chains propagating along [010]. PMID:22969648

Determination of sulfonamides in animal tissues by modified QuEChERS and liquid chromatography tandem mass spectrometry.

PubMed

Wen, Ching-Hsuan; Lin, Shu-Ling; Fuh, Ming-Ren

2017-03-01

In this study, the salting-out solvent extraction and dispersive solid-phase extraction (dSPE) clean-up steps in QuEChERS (quick, easy, cheap, effective, rugged, and safe) method were optimized to reduce matrix effect and efficiently extract target sulfonamides from a variety of edible animal tissues. The extracted sulfonamides were then analyzed using liquid chromatography tandem mass spectrometry (LC-MS/MS). Good extraction recoveries (74.0-100.3% in five different sources of animal tissues; n=3) with acceptable matrix effect (<10%, except for liver samples) were obtained using the proposed method. For the first time, a commercial ND-lipids cartridge was used to remove hydrophobic matrix components from fat-rich animal tissues in the clean-up step of QuEChERS. In addition, good linearity (0.125-12.5ngg -1 ) was observed using matrix-matched calibration (in beef). Limits of detection (LODs) were estimated at 0.01-0.03ngg -1 in beef, pork, and chicken samples. For beef tripe and pig liver samples, the LODs were in the range of 0.02-0.04ngg -1 . Good intra-day/inter-day precision (1.0-10.5%/0.4-8.0%) and accuracy (95.2-107.2%/97.8-102.1%) were also achieved using the modified QuEChERS for sample pretreatment. The applicability of the modified QuEChERS-LC-MS/MS method was demonstrated by determining the occurrence of target sulfonamides in various edible animal tissues for potential food safety analysis. Copyright © 2016 Elsevier B.V. All rights reserved.

Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.

PubMed

Zhang, Hongyan; Wang, Lei; Zhang, Yan; Fang, Guozhen; Zheng, Wenjie; Wang, Shuo

2007-03-21

Direct competitive enzyme-linked immunosorbent assays (ELISA) were developed to detect a broad range of sulfonamides in various matrices. Screening for this class of antibiotics in pig muscle, chicken muscle, fish, and egg extracts was accomplished by simple, rapid extraction methods carried out with only phosphate-buffered saline (PBS) buffer. Twenty milliliters of extract solution was added to 4 g of sample to extract the sulfonamide residues, and sample extracts diluted with assay buffer were directly analyzed by ELISA; matrix effects could be avoided with 1:5 dilution of pig muscle, chicken muscle, and egg extracts with PBS and 1:5 dilution of fish extract with 1% bovine serum albumin (BSA)-PBS. For liver sample, the extraction method was a little more complicated; 2 g of sample was added to 20 mL of ethanol, mixed, and then centrifuged. The solvent of 10 mL of the upper liquid was removed, and the residues were dissolved in 10 mL of PBS and then filtered; the filtrate was diluted two-fold with 0.5% BSA-PBS for ELISA. These common methods were able to detect seven sulfonamide residues such as sulfisozole, sulfathiazole, sufameter, sulfamethoxypyridazine, sulfapyridine, sulfamethizole, and sulfachlorpyridazine in pig muscle, liver, chicken muscle, egg, and fish. The assay's detection limits for these compounds were less than 100 microg kg-1. Various extraction methods were tested, and the average recovery (n=3) of 100 microg kg-1 for the matrices was found to range from 77.3 to 123.7%.

Analyses of sulfonamide antibiotics in meat samples by on-line concentration capillary electrochromatography-mass spectrometry.

PubMed

Cheng, Yi-Jie; Huang, Sing-Hao; Singco, Brenda; Huang, Hsi-Ya

2011-10-21

In this work, a series of poly(divinylbenzene-alkyl methacrylate) monolithic stationary phases, which were prepared by single step in situ polymerization of divinylbenzene and various alkyl methacrylates (butyl-, octyl-, lauryl- or stearyl methacrylate), were developed as separation columns of nine common sulfonamide antibiotics for capillary electrochromatography (CEC) coupled to mass spectrometry (MS). Results indicated that the sulfonamide's retention became weak with increased carbon chain length of alkyl methacrylate monomer (for example, t(R)=68 min and 21 min for butyl- and lauryl methacrylate, respectively). Among them, the poly(divinylbenzene-octyl methacrylate) (poly(DVB-OMA)) monolith was regarded as the optimal separation column as this provided better resolution within the shortest retention time. Moreover, the cross-sectional roughness of the monolithic column-end, that was used to couple to the ESI interface, strongly influenced the electrospray stability in the CEC-MS. Before the column was connected to the ESI-MS, a simple polishing was done to reduce the roughness of the column end that resulted to a great improvement in the signal stability. The relative standard deviations (RSDs) of the peak areas for the unpolished and polished ends of the poly(DVB-OMA) columns (n=5) were in the range of 46.1-60.2% and 8.9-16.4%, respectively. Furthermore, optimization of the mobile phase composition and the gradient elution strategy successfully determined the sulfonamide antibiotics in meat samples with as low as 10 μg/L level. Copyright © 2011 Elsevier B.V. All rights reserved.

Determination of Sulfonamide Residues in Food by Capillary Zone Electrophoresis with On-Line Chemiluminescence Detection Based on an Ag(III) Complex

PubMed Central

Dai, Tingting; Duan, Jie; Li, Xinghua; Xu, Xiangdong; Shi, Hongmei; Kang, Weijun

2017-01-01

The presence of sulfonamide (SA) residues in foods is largely due to the raising of animals with sulfonamide antibiotics added or polluted feedstuff. In this paper, a sensitive method was developed for the determination of the residues of three sulfonamides in animal-derived food; the SAs include sulfadimidine (SDD), sulfadiazine (SDZ), and sulfathiazole (STZ). The method is based on capillary zone electrophoresis (CE) with online chemiluminescence (CL) detection, using an Ag(III) complex as an oxidant. These SAs have an inhibiting effect on the Ag(III)–luminol CL reaction. The electrophoretic buffer is 12.0 mM sodium borate. Under a set of optimized conditions, the linear ranges for the detections were found to be 10.0–200 µg·mL−1 for SDD and SDZ, and 2.0–50.0 µg·mL−1 for STZ. The detection limits were 2.75, 3.14, and 0.65 µg·mL−1 for SDD, SDZ, and STZ, respectively. Relative standard deviations (RSD) for the peak heights were between 2.1% and 2.8% (n = 7). The proposed method was used in the analysis of the SAs in samples from pork meat, chicken meat, and milk, showing satisfactory detection results. A reaction mechanism was also proposed for the Ag(III)–luminol–SA CL reactions. The method has potential applications for the monitoring of residue levels of the three SAs in food, providing food safety data. PMID:28621728

Optimisation of Croton gratissimus Oil Extraction by n-Hexane and Ethyl Acetate Using Response Surface Methodology.

PubMed

Jiyane, Phiwe Charles; Tumba, Kaniki; Musonge, Paul

2018-04-01

The extraction of oil from Croton gratissimus seeds was studied using the three-factor five-level full-factorial central composite rotatable design (CCRD) of the response surface methodology (RSM). The effect of the three factors selected, viz., extraction time, extraction temperature and solvent-to-feed ratio on the extraction oil yield was investigated when n-hexane and ethyl acetate were used as extraction solvents. The coefficients of determination (R 2 ) of the models developed were 0.98 for n-hexane extraction and 0.97 for ethyl acetate extraction. These results demonstrated that the models developed adequately represented the processes they described. From the optimized model, maximum extraction yield obtained from n-hexane and ethyl acetate extraction were 23.88% and 23.25%, respectively. In both cases the extraction temperature and solvent-to-feed ratio were 35°C and 5 mL/g, respectively. In n-hexane extraction the maximum conditions were reached only after 6 min whereas in ethyl acetate extraction it took 20 min to get the maximum extraction oil yield. Oil extraction of Croton gratissimus seeds, in this work, favoured the use of n-hexane as an extraction solvent as it offered higher oil yields at low temperatures and reduced residence times.

Multisite reproducibility of the broth microdilution method for susceptibility testing of Nocardia species.

PubMed

Conville, Patricia S; Brown-Elliott, Barbara A; Wallace, Richard J; Witebsky, Frank G; Koziol, Deloris; Hall, Geraldine S; Killian, Scott B; Knapp, Cindy C; Warshauer, David; Van, Tam; Wengenack, Nancy L; Deml, Sharon; Woods, Gail L

2012-04-01

Antimicrobial susceptibility testing (AST) of clinical isolates of Nocardia is recommended to detect resistance to commonly used antimicrobial agents; such testing is complicated by difficulties in inoculum preparation and test interpretation. In this study, six laboratories performed repetitive broth microdilution testing on single strains of Nocardia brasiliensis, Nocardia cyriacigeorgica, Nocardia farcinica, Nocardia nova, and Nocardia wallacei. For each isolate, a total of 30 microdilution panels from three different lots were tested at most sites. The goal of the study was to determine the inter- and intralaboratory reproducibility of susceptibility testing of this group of isolates. Acceptable agreement (>90% agreement at ±1 dilution of the MIC mode) was found for amikacin, ciprofloxacin, clarithromycin, and moxifloxacin. After eliminating MIC values from single laboratories whose results showed the greatest deviation from those of the remaining laboratories, acceptable agreement was also found for amoxicillin-clavulanic acid, linezolid, minocycline, and tobramycin. Results showed unsatisfactory reproducibility of broth microdilution testing of ceftriaxone with N. cyriacigeorgica and N. wallacei, tigecycline with N. brasiliensis and N. cyriacigeorgica, and sulfonamides with N. farcinica and N. wallacei. N. nova ATCC BAA-2227 is proposed as a quality control organism for AST of Nocardia sp., and the use of a disk diffusion test for sulfisoxazole is proposed as a check of the adequacy of the inoculum and to confirm sulfonamide MIC results.

Sulfonamide Resistance in Clinical Isolates of Campylobacter jejuni: Mutational Changes in the Chromosomal Dihydropteroate Synthase

PubMed Central

Gibreel, Amera; Sköld, Ola

1999-01-01

The characterization of the genetic basis of sulfonamide resistance in Campylobacter jejuni was attempted. The resistance determinant from a sulfonamide-resistant strain of C. jejuni was cloned and was found to show 42% identity with the folP gene (which codes for dihydropteroate synthase, the target of sulfonamides) of the related bacterium Helicobacter pylori. The sequences of the areas surrounding the folP gene in C. jejuni showed similarity to those of the areas surrounding the corresponding gene in H. pylori. The folP gene of C. jejuni, which mediates the resistance, was observed to show particular features when it was compared to other known folP genes. One of these features is the presence of two pairs of direct repeats (15 and 27 bp) within the coding sequence of the gene. Comparison of the C. jejuni folP genes that mediate susceptibility and resistance revealed the occurrence of mutations that changed four amino acid residues. Resistance of C. jejuni to sulfonamides could be associated with one or several of these four mutational substitutions, which all occurred in the five different resistant isolates studied. The codon for one of these changed amino acids was found to be located in the second direct repeat within the coding sequence of the gene. The change made the repeat perfect. The transformation of both the resistance and the susceptibility variants of the gene into an Escherichia coli folP knockout mutant was found to complement the dihydropteroate synthase deficiency, confirming that the characterized sulfonamide resistance determinant codes for the C. jejuni dihydropteroate synthase enzyme. Kinetic measurements established different affinities of sulfonamide for the dihydropteroate synthase enzyme isolated from the resistant and susceptible strains. In conclusion, sulfonamide resistance in C. jejuni was shown to be associated with mutational changes in the chromosomally located gene for dihydropteroate synthase, the target of sulfonamides. PMID:10471557

Biodegradation of 2-methylquinoline by Enterobacter aerogenes TJ-D isolated from activated sludge.

PubMed

Wang, Lin; Li, Yongmei; Duan, Jingyuan

2013-07-01

Bacterial strain Enterobacter aerogenes TJ-D capable of utilizing 2-methylquinoline as the sole carbon and energy source was isolated from acclimated activated sludge under denitrifying conditions. The ability to degrade 2-methylquinoline by E. aerogenes TJ-D was investigated under denitrifying conditions. Under optimal conditions of temperature (35 degrees C) and initial pH 7, 2-methylquinoline of 100 mg/L was degraded within 176 hr. The degradation of 2-methylquinoline by E. aerogenes TJ-D could be well described by the Haldane model (R2 > 0.91). During the degradation period of 2-methylquinoline (initial concentration 100 mg/L), nitrate was almost completely consumed (the removal efficiency was 98.5%), while nitrite remained at low concentration (< 0.62 mg/L) during the whole denitrification period. 1,2,3,4-Tetrahydro-2-methylquinoline, 4-ethyl-benzenamine, N-butyl-benzenamine, N-ethyl-benzenamine and 2,6-diethyl-benzenamine were metabolites produced during the degradation. The degradation pathway of 2-methylquinoline by E. aerogenes TJ-D was proposed. 2-Methylquinoline is initially hydroxylated at C-4 to form 2-methyl-4-hydroxy-quinoline, and then forms 2-methyl-4-quinolinol as a result of tautomerism. Hydrogenation of the heterocyclic ring at positions 2 and 3 produces 2,3-dihydro-2-methyl-4-quinolinol. The carbon-carbon bond at position 2 and 3 in the heterocyclic ring may cleave and form 2-ethyl-N-ethyl-benzenamine. Tautomerism may result in the formation of 2,6-diethyl-benzenamine and N-butyl-benzenamine. 4-Ethyl-benzenamine and N-ethyl-benzenamine were produced as a result of losing one ethyl group from the above molecules.

Oxidation of Sulfonamides in Aqueous Solution by UV-TiO2-Fe(VI).

PubMed

Ma, Yan; Zhang, Kejia; Li, Cong; Zhang, Tuqiao; Gao, Naiyun

2015-01-01

The photocatalytic degradation of sulfonamides in aqueous TiO2 suspension under UV irradiation has been investigated using potassium ferrate as electron acceptors. The results showed that the stability of Fe(VI) is dependent on pH significantly, and the stability reduces obviously in the presence of UV-TiO2. The experiments indicated that Fe(VI) could effectively scavenge the conduction band electrons from the surface of TiO2. The photocatalytic oxidation of sulfonamides with Fe(VI) was found to be much faster than that without Fe(VI). The SD, SM, and SMX concentration was greatly reduced by 89.2%, 83.4%, and 82.0%, respectively, after 10 min with UV-TiO2-Fe(VI), comparing to 65.2%, 66.0%, and 71.9%, respectively, with Fe(VI) only in the dark and 71.3%, 72.7%, and 76.0%, respectively, with UV-TiO2. The pH value of solution significantly influenced the sulfonamides degradation in UV-TiO2-Fe(VI) system. The degradation amount of sulfonamides after 10 min was a maximum at pH 7. The intermediate products of sulfonamides oxidation by UV-TiO2-Fe(VI) were analysed by LC-HESI-MS-MS and the results suggested that a majority of sulfonamides turned into large-molecule products without complete mineralization.

Oxidation of Sulfonamides in Aqueous Solution by UV-TiO2-Fe(VI)

PubMed Central

Ma, Yan; Zhang, Kejia; Li, Cong; Zhang, Tuqiao; Gao, Naiyun

2015-01-01

The photocatalytic degradation of sulfonamides in aqueous TiO2 suspension under UV irradiation has been investigated using potassium ferrate as electron acceptors. The results showed that the stability of Fe(VI) is dependent on pH significantly, and the stability reduces obviously in the presence of UV-TiO2. The experiments indicated that Fe(VI) could effectively scavenge the conduction band electrons from the surface of TiO2. The photocatalytic oxidation of sulfonamides with Fe(VI) was found to be much faster than that without Fe(VI). The SD, SM, and SMX concentration was greatly reduced by 89.2%, 83.4%, and 82.0%, respectively, after 10 min with UV-TiO2-Fe(VI), comparing to 65.2%, 66.0%, and 71.9%, respectively, with Fe(VI) only in the dark and 71.3%, 72.7%, and 76.0%, respectively, with UV-TiO2. The pH value of solution significantly influenced the sulfonamides degradation in UV-TiO2-Fe(VI) system. The degradation amount of sulfonamides after 10 min was a maximum at pH 7. The intermediate products of sulfonamides oxidation by UV-TiO2-Fe(VI) were analysed by LC-HESI-MS-MS and the results suggested that a majority of sulfonamides turned into large-molecule products without complete mineralization. PMID:26347888

Long-range DHPS mutations unexpectedly increase Mycobacterium chimaera susceptibility to sulfonamides.

PubMed

Gotthard, Guillaume; Muhammed Ameen, Sirwan; Drancourt, Michel; Chabriere, Eric

2013-12-01

The two closely related mycobacteria, Mycobacterium intracellulare and Mycobacterium chimaera, exhibit a more than two-fold difference in their in vitro susceptibility to sulfonamides. Sulfonamides are antibiotics targeting the 6-hydroxymethyl-7,8-dihydropteroate synthase (DHPS) enzyme involved in the folate synthesis pathway. Comparing the DHPS gene sequence in six M. intracellulare and M. chimaera types trains and clinical isolates yielded only four amino acid changes. In silico structural modelling surprisingly indicated that these amino acids are not located in the active site of DHPS and do not interact directly with sulfonamides. Unexpectedly, these amino acids in distal positions may play a key role in the increased sulfonamide susceptibility observed in M. chimaera compared with M. intracellulare. This example illustrates how three-dimensional models could help to identify distal mutations capable of modulating enzymatic activity. Copyright © 2013 International Society for Chemotherapy of Infection and Cancer. Published by Elsevier Ltd. All rights reserved.

Proteomics analysis of altered proteins in kidney of mice with aristolochic acid nephropathy using the fluorogenic derivatization-liquid chromatography-tandem mass spectrometry method.

PubMed

Lin, Chia-En; Chang, Wen-Shin; Lee, Jen-Ai; Chang, Ting-Ya; Huang, Yu-Shen; Hirasaki, Yoshiro; Chen, Hung-Shing; Imai, Kazuhiro; Chen, Shih-Ming

2018-03-01

Aristolochic acid (AA) causes interstitial renal fibrosis, called aristolochic acid nephropathy (AAN). There is no specific indicator for diagnosing AAN, so this study aimed to investigate the biomarkers for AAN using a proteomics method. The C3H/He female mice were given ad libitum AA-distilled water (0.5 mg/kg/day) and distilled water for 56 days in the AA and normal groups, respectively. The AA-induced proteins in the kidney were investigated using a proteomics study, including fluorogenic derivatization with 7-chloro-N-[2-(dimethylamino)ethyl]-2,1,3-benzoxadiazole-4-sulfonamide, followed by high-performance liquid chromatography analysis and liquid chromatography tandem mass spectrometry with a MASCOT database searching system. There were two altered proteins, thrombospondin type 1 (TSP1) and G protein-coupled receptor 87 (GPR87), in the kidney of AA-group mice on day 56. GPR87, a tumorigenesis-related protein, is reported for the first time in the current study. The renal interstitial fibrosis was certainly induced in the AA-group mice under histological examination. Based on the results of histological examination and the proteomics study, this model might be applied to AAN studies in the future. TSP1 might be a novel biomarker for AAN, and the further role of GPR87 leading to AA-induced tumorigenesis should be researched in future studies. Copyright © 2017 John Wiley & Sons, Ltd.

21 CFR 176.160 - Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine.

Code of Federal Regulations, 2010 CFR

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine. 176.160 Section 176.160 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS...

21 CFR 176.160 - Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine. 176.160 Section 176.160 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS...

21 CFR 176.160 - Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine.

Code of Federal Regulations, 2013 CFR

2013-04-01

... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine. 176.160 Section 176.160 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS...

21 CFR 176.160 - Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine. 176.160 Section 176.160 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS...

4-Meth­oxy-N-(1-methyl-1H-indazol-5-yl)benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Geffken, Detlef; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

The indazole ring system [maximum deviation = 0.013 (2) Å] of the title compound, C15H15N3O3S, makes a dihedral angle of 50.11 (7)° with the benzene ring. In the crystal, cohesion is provided by C—H⋯O and N—H⋯N hydrogen bonds, which link the molecules into chains propagating along the b-axis direction. PMID:24427037

Effects of sorbate speciation on sorption of selected sulfonamides in three loamy soils

USGS Publications Warehouse

Kurwadkar , Sudarshan T.; Adams, Craig D.; Meyer, Michael T.; Kolpin, Dana W.

2007-01-01

Sorption of sulfamethazine (SMN) and sulfathiazole (STZ) was investigated in three soils, a North Carolina loamy sand, an Iowa sandy loam, and a Missouri loam, under various pH conditions. A significant increase in the sorption coefficient (KD) was observed in all three soils, as the sulfonamides converted from an anionic form at higher pH to a neutral/cationic form at lower pH. Above pH 7.5, sulfonamides exist primarily in anionic form and have higher aqueous solubility and no cationic character, thereby consequently leading to lower sorption to soils. The effect of speciation on sorption is not the same for all sulfonamides; it is a function of the pH of the soil and the pKa of the sulfonamides. The results indicate that, for the soils under investigation, SMN has comparatively lower KD values than STZ. The pH-dependent sorption of sulfonamides was observed to be consistent in all three soils investigated. The KD values for each speciated formcationic, neutral, and anionicwere calculated using an empirical model in which the species-specific sorption coefficients (KD0, KD1, and KD2) were weighted with their respective fractions present at any given pH.

Metal-Organic Framework-Polymer Composite as a Highly Efficient Sorbent for Sulfonamide Adsorption and Desorption: Effect of Coordinatively Unsaturated Metal Site and Topology.

PubMed

Shih, Yung-Han; Wang, Kuen-Yun; Singco, Brenda; Lin, Chia-Her; Huang, Hsi-Ya

2016-11-08

In this study, we first demonstrated the effect of two types of metal-organic framework-polymer (MOF-polymer) monoliths on in-tube solid-phase microextraction (IT-SPME) of sulfonamides. Sulfonamides were successfully adsorbed onto MIL-101(Cr)-polymer but were difficult to elute due to these sulfonamides could interact via Lewis acid-base interaction with the presence of Cr(III) coordinatively unsaturated metal sites (CUS). Moreover, the cage-type topology of MIL-101(Cr) that could produce multiple pathways thus complicates the desorption of the test analytes from the sorbent. Contrastingly, MIL-53(Al)-polymer provided weaker Al(III) CUS, and its one-dimensional channel pore structure could provide an unhindered pathway for sulfonamides transfer during elution. After optimizing the IT-SPME condition such as MOF content, pH of sample matrix, column length, extraction flow rate, and elution volume, the calculated extraction recovery of sulfonamides in MIL-53(Al)-polymer as analyzed by microemulsion electrokinetic chromatography (MEEKC) were in the range of 40%-90% with relative standard deviations (RSDs) below 5% and a reusability of at least 30 times.

Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.

PubMed

Di Sabatino, Marcello; Di Pietra, Anna Maria; Benfenati, Luigi; Di Simone, Bruno

2007-01-01

A liquid chromatography (LC) method is described for the simultaneous determination of 10 commonly used sulfonamide drug residues in meat. The 10 sulfonamide drugs of interest were sulfadiazine, sulfathiazole, sulfamerazine, sulfadimidine, sulfamethizole, sulfamonomethoxine, sulfachloropyridazine, sulfadoxine, sulfadimethoxine, and sulfaquinoxaline. The residues were extracted with acetone-chloroform (1 + 1). Sulfonamides were quantitatively retained in the extracting solution and afterwards eluted from a cation-exchanger solid-phase extraction cartridge with a solution of methanol-aqueous ammonia. The solution was dried, reconstituted with 5 mL methanol and filtered before analysis by LC-ultraviolet using a C18 column with a mobile phase gradient of potassium dihydrogen phosphate buffer, pH 2.5, and methanol-acetonitrile (30 + 70, v/v). The method was applied to cattle, swine, chicken, and sheep muscle tissues. The validation was performed with a fortified cattle meat sample at level of 100 ppb, which is the administrative maximum residue limit for sulfonamides in the European Union. The limit of quantitation for all sulfonamides was between 3 and 14 ppb. Recovery was evaluated for different meat matrixes. The mean recovery values were between 66.3% for pork meat samples and 71.5% for cattle meat samples.

Environmental fate of two sulfonamide antimicrobial agents in soil.

PubMed

Accinelli, Cesare; Koskinen, William C; Becker, Joanna M; Sadowsky, Michael J

2007-04-04

Veterinary antimicrobial agents have been detected in a number of environmental samples, including agricultural soils. In this study, we investigated the persistence and sorption of the sulfonamides sulfamethazine (SMZ) and sulfachloropyridine (SCP) in soil and their potential effects on soil microorganisms. The sulfonamides dissipated more rapidly from the silt loam soil as compared to the sandy soil. Average half-lives of SMZ and SPC among the two soils were 18.6 and 21.3 days, respectively. The presence of liquid swine slurry (5% v/w) decreased sulfonamide persistence in the silt loam soil. The lower persistence of the antimicrobials in liquid swine slurry-amended soil was likely due to higher microbial activity, as compared to unamended soil, and/or to the greater bioavailability of the sulfonamides to degrading microorganisms, as estimated by sorption isotherms. Concentrations of SMZ and SPC up to 100 microg g-1 had no effect on antimicrobial degradation rates and soil microorganisms. These studies suggest that higher sulfonamide concentrations would be necessary to affect the main processes controlling their environmental fates in soil, but at the concentrations normally found in the environment, there would be little or no effects.

Vemurafenib-induced toxic epidermal necrolysis: possible cross-reactivity with other sulfonamide compounds.

PubMed

Bellón, T; Lerma, V; González-Valle, O; González Herrada, C; de Abajo, F J

2016-03-01

Vemurafenib is a newly licensed target-directed medication. It has been proven to improve the survival of patients with metastatic melanoma and the BRAF(V600E) mutation; however, adverse cutaneous reactions are frequent. Few cases of life-threatening severe cutaneous adverse reactions (SCARs) induced by vemurafenib have been reported. Dabrafenib, another selective BRAF inhibitor, has been licensed recently as an alternative drug with the same indications. From a molecular point of view, both vemurafenib and dabrafenib contain a sulfonamide group; cross-reactivity to sulfonamide compounds has been reported in allergic patients. We report on a patient with vemurafenib-induced toxic epidermal necrolysis (TEN). In vitro analysis of lymphocyte reactivity to vemurafenib showed positive results, confirming drug causality. In addition, lymphocytes from the patient reacted to dabrafenib and to the antibiotic sulfonamide drug sulfamethoxazole. Moreover, lymphocytes from two patients with cutaneous adverse reactions to sulfamethoxazole also reacted to vemurafenib and dabrafenib in vitro. These data strongly suggest that there might be clinical cross-reactivity between BRAF inhibitors and sulfonamides in some patients. Thus, precautions should be taken to avoid sulfonamide drugs as much as possible in patients showing serious hypersensitivity reactions to vemurafenib and vice versa. © 2015 British Association of Dermatologists.

Synthesis and crystal structure of (S, S, S, S)-N, N′-bis[N-(P-toluenesulfonamido)-1,2-diphenylethyl]ethylenediamine

DOE Office of Scientific and Technical Information (OSTI.GOV)

Liu, X.-G.; Zhang, T.; Hu, Y.-Y.

2013-12-15

(S, S, S, S)-N,N′-bis[N-(p-toluenesulfonamido)-1,2-diphenylethyl] ethylenediamine (C{sub 44}H{sub 46}N{sub 4}O{sub 4}S{sub 2}), has been synthesized and structurally characterized by elemental analysis, {sup 1}H-NMR, MS, IR and single-crystal X-ray diffraction. The title compound contains four chiral centers with C atoms in S configuration. Molecules are connected to one another by hydrogen bonds between sulfonamide nitrogen and sulfonyl oxygen to form chains alone a axis.

Are perfluoroalkyl acids in waste water treatment plant effluents the result of primary emissions from the technosphere or of environmental recirculation?

PubMed

Filipovic, Marko; Berger, Urs

2015-06-01

Wastewater treatment plants (WWTP) have been suggested to be one of the major pathways of perfluoroalkyl acids (PFAAs) from the technosphere to the aquatic environment. The origin of PFAAs in WWTP influents is either from current primary emissions or a result of recirculation of PFAAs that have been residing and transported in the environment for several years or decades. Environmental recirculation can then occur when PFAAs from the environment enter the wastewater stream in, e.g., tap water. In this study 13 PFAAs and perfluorooctane sulfonamide were analyzed in tap water as well as WWTP influent, effluent and sludge from three Swedish cities: Bromma (in the metropolitan area of Stockholm), Bollebygd and Umeå. A mass balance of the WWTPs was assembled for each PFAA. Positive mass balances were observed for PFHxA and PFOA in all WWTPs, indicating the presence of precursor compounds in the technosphere. With regard to environmental recirculation, tap water was an important source of PFAAs to the Bromma WWTP influent, contributing >40% for each quantified sulfonic acid and up to 30% for the carboxylic acids. The PFAAs in tap water from Bollebygd and Umeå did not contribute significantly to the PFAA load in the WWTP influents. Our results show that in order to estimate current primary emissions from the technosphere, it may be necessary to correct the PFAA emission rates in WWTP effluents for PFAAs present in tap water, especially in the case of elevated levels in tap water. Copyright © 2014 Elsevier Ltd. All rights reserved.

Comparative mobility of sulfonamides and bromide tracer in three soils

USGS Publications Warehouse

Kurwadkar, S.T.; Adams, C.D.; Meyer, M.T.; Kolpin, D.W.

2011-01-01

In animal agriculture, sulfonamides are one of the routinely used groups of antimicrobials for therapeutic and sub-therapeutic purposes. It is observed that, the animals when administered the antimicrobials, often do not completely metabolize them; and excrete the partially metabolized forms into the environment. Due to the continued use of antimicrobials and disposal of untreated waste, widespread occurrence of partially metabolized antimicrobials in aquatic and terrestrial environments has been reported in various scientific journals. In this research, the mobility of two sulfonamides - sulfamethazine (SMN), sulfathiazole (STZ) and a conservative bromide tracer was investigated in three soils collected from regions in the United States with large number of concentrated animal-feed operations. Results of a series of column studies indicate that the mobility of these two sulfonamides was dependent on pH, soil charge density, and contact time. At low pH and high charge density, substantial retention of sulfonamides was observed in all three soils investigated, due to the increased fraction of cationic and neutral forms of the sulfonamides. Conversely, enhanced mobility was observed at high pH, where the sulfonamides are predominantly in the anionic form. The results indicate that when both SMN and STZ are predominantly in anionic forms, their mobility approximates the mobility of a conservative bromide tracer. This observation is consistent for the mobility of both SMN and STZ individually, and also in the presence of several other antimicrobials in all three soils investigated. Higher contact time indicates lower mobility due to increased interaction with soil material. ?? 2011.

21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2014 CFR

2014-04-01

... (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, geranial, neral). Decanal (N-decylaldhehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Diacetyl (2,3-butandeione). Ethyl acetate. Ethyl...

21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2013 CFR

2013-04-01

... (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, geranial, neral). Decanal (N-decylaldhehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Diacetyl (2,3-butandeione). Ethyl acetate. Ethyl...

21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2012 CFR

2012-04-01

... (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, geranial, neral). Decanal (N-decylaldhehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Diacetyl (2,3-butandeione). Ethyl acetate. Ethyl...

21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2010 CFR

2010-04-01

... (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, geranial, neral). Decanal (N-decylaldhehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Diacetyl (2,3-butandeione). Ethyl acetate. Ethyl...

21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2011 CFR

2011-04-01

... (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, geranial, neral). Decanal (N-decylaldhehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Diacetyl (2,3-butandeione). Ethyl acetate. Ethyl...

Synthesis and Biological Evaluation of Substituted N-[3-(1H-Pyrrol-1-yl)methyl]-1,2,5,6-tetrahydropyridin-1-yl]benzamide/ benzene Sulfonamides as Anti-Inflammatory Agents

PubMed Central

Gangapuram, Madhavi; Mazzio, Elizabeth; Eyunni, Suresh; Soliman, Karam F. A.; Redda, Kinfe K.

2014-01-01

The pharmacological activities of tetrahydropyridine (THP) derivatives are dependent on the substituent ring moiety. In this study, we investigate the anti-inflammatory activities of 12 newly synthesized substituted N-[3-(1H-pyrrol-1-yl)methyl]-1,2,5,6-tetrahydrobenzamide/benzene sulfonamides (9a–l) in murine BV-2 microglial cells. All compounds were initially screened for attenuation of nitric oxide (NO) production in lipopolysaccharide (LPS) (1 μg/mL)-activated microglial cells. The data show that only SO2-substituted THPs were effective at sub-lethal concentrations (IC50 values of 12.92 μM (9i), 14.64 μM (9j), 19.63 μM (9k)) relative to L-N6-(1-iminoethyl)lysine positive control (IC50 = 3.1 μM). The most potent SO2-substituted compound (9i) also blocked the LPS-inducible nitric oxide synthase (iNOS) and attenuated the release of several cytokines including IL-1α, IL-10, and IL-6. These findings establish the moderate immunomodulating effects of SO2-substituted THP derivatives. PMID:24585402

Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.

PubMed

Thiele-Bruhn, S; Aust, M O

2004-07-01

Sorption of p-aminobenzoic acid (pABA) and five sulfonamide antibiotics to loess Chernozem topsoil amended with varied additions of pig slurry was investigated in batch trials. In unfertilized soil, partition coefficients (Kd) of sulfonamides ranged from 0.3 to 2.0. Strong sorption nonlinearity (1/n = 0.5 to 0.8) was best fitted by the Freundlich isotherm (R2 = 0.7 to 1.0) and was indicative for specific sorption mechanisms. Adsorption to pig slurry was much stronger, and nondesorbable portions were increased compared with soil. However, in a mixture of soil and slurry (50:1 w/w), sorption of the antibiotics was significantly decreased at a lower concentration range of pABA and the sulfonamides. This was attributed to competitive adsorption of dissolved organic matter (DOM) constituents from manure. An increase in pig slurry amendment resulted in increased total organic matter, DOM concentration, and ionic strength, but pH decreased. As a result, the nonadsorbed portions of pABA, sulfanilamide, and sulfadiazine (logD(ow) < -0.4) ranged from 47% to 82% of the applied concentration in the differently manured substrates. Dissolved fractions of the antibiotics reached a maximum at a soil-slurry ratio of 9:1 and decreased with further addition of manure. This decrease was related to the formation of less-effective DOM associates in solution. The adsorbed and desorbed portions of the less-polar substances--sulfadimidine, sulfadimethoxine, and sulfapyridine (logD(ow) > 0.1)--remained nearly constant in the presence of increased manure input. The pH changes caused by manure amendment strongly affected ionisation status of the latter compounds, thus resulting in increased adsorption, which compensated the mobilizing effect of DOM. It is suggested that the effect of manure be considered in test methods to determine the soil retention of pharmaceutical substances.

21 CFR 176.160 - Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine.

Code of Federal Regulations, 2014 CFR

2014-04-01

... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Chromium (Cr III) complex of N-ethyl-N-heptadecylfluoro-octane sulfonyl glycine. 176.160 Section 176.160 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) INDIRECT FOOD ADDITIVES: PAPER AND PAPERBOARD COMPONENTS Substances for Use Only as Components of...

Effect of meteorology and soil condition on metolachlor and atrazine volatilization over a 10 year period

USDA-ARS?s Scientific Manuscript database

A 10-year study was conducted to focus on the impact of soil and climatic factors governing herbicide volatilization from an agricultural field. For the first 5 years, metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] and atrazine [6-chloro-N-ethyl-N’-(1-methyl...

40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

Code of Federal Regulations, 2010 CFR

2010-07-01

... must incorporate this new information, and any information on methods for protecting against such risk....3152 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT... significant new use of this substance is any manner or method of manufacture, import, or processing associated...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2012 CFR

2012-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2013 CFR

2013-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2011 CFR

2011-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2010 CFR

2010-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

Biocatalytic Asymmetric Synthesis of (1R, 2S)-N-Boc-vinyl-ACCA Ethyl Ester with a Newly Isolated Sphingomonas aquatilis.

PubMed

Zhu, Shaozhou; Shi, Ying; Zhang, Xinyu; Zheng, Guojun

2018-02-01

1-amino cyclopropane-1-carboxylic acid (ACCA) and its derivatives are essential pharmacophoric unit that widely used in drug research and development. Specifically, (1R, 2S)-N-Boc-vinyl-ACCA ethyl ester (vinyl-ACCA) is a key chiral intermediate in the synthesis of highly potent hepatitis C virus (HCV) NS3/4A protease inhibitors such as asunaprevir and simeprevir. Developing strategies for the asymmetric synthesis of vinyl-ACCA is thus extremely high demand. In this study, 378 bacterial strains were isolated from soil samples using N-Boc-vinyl-ACCA ethyl ester as the sole carbon source and were screened for esterase activity. Fourteen of which worked effectively for the asymmetric synthesis of (1R, 2S)-N-Boc-1-vinyl ACCA ethyl ester. The strain CY-2, identified as Sphingomonas aquatilis, which showed the highest stability and enantioselectivity was selected as whole cell biocatalyst for further study. A systematic study of all factors influencing the enzymatic hydrolysis was performed. Under optimized conditions, resolution of rac-vinyl-ACCA to (1R, 2S)-N-Boc-1-vinyl ACCA ethyl ester with 88.2% ee and 62.4% conversion (E = 9) was achieved. Besides, S. aquatilis was also used to transform other 10 different substrates. Notably, it was found that 7 of them could be stereoselectively hydrolyzed, especially for (1R,2S)-1-amino-vinyl-ACCA ethyl ester hydrochloride (99.6% ee, E>200). Our investigations provide a new efficient whole cell biocatalyst for resolution of ACCA and might be developed for industry application.

An erythrosin B-based "turn on" fluorescent sensor for detecting perfluorooctane sulfonate and perfluorooctanoic acid in environmental water samples.

PubMed

Cheng, Zhen; Du, Lingling; Zhu, Panpan; Chen, Qian; Tan, Kejun

2018-05-04

Because of the serious harm to animals and the environment associated with perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA), a rapid, sensitive and low-cost method for detecting PFOS and PFOA is of great importance. In this paper, a novel sensing method has been proposed for the highly sensitive detection of PFOS and PFOA in environmental water samples based on the "turn-on" switch of erythrosine B (EB)-hexadecyltrimethylammonium bromide (CTAB) system. In pH 8.55 Britton-Robinson (BR) buffer, EB can react with CTAB by electrostatic attraction, resulting in a strong fluorescence quenching of EB. With a subsequent addition of the CTAB, a red-shift occurred (11 nm), followed by a significant increase in fluorescence at high surfactant concentrations. It was found that PFOS and PFOA can obviously enhance fluorescence intensity of EB-CTAB system. The enhanced fluorescence intensity is proportional to the concentration of PFOS and PFOA in the range of 0.05-10 μM with detection limit of 12.8 nM and 11.8 nM (3σ), respectively. The presented assay has been successfully applied to sensing PFOS and PFOA in real water samples with RSD ≤ 4.3% and 2.9%, respectively. Copyright © 2018 Elsevier B.V. All rights reserved.

21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2010 CFR

2010-04-01

... (parapropenyl anisole). Benzaldehyde (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, gera-nial, neral). Decanal (N-decylaldehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3...

21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2011 CFR

2011-04-01

... (parapropenyl anisole). Benzaldehyde (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, gera-nial, neral). Decanal (N-decylaldehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3...

21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2013 CFR

2013-04-01

... (parapropenyl anisole). Benzaldehyde (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, gera-nial, neral). Decanal (N-decylaldehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3...

21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2012 CFR

2012-04-01

... (parapropenyl anisole). Benzaldehyde (benzoic aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde). Citral (2,6-dimethyloctadien-2,6-al-8, gera-nial, neral). Decanal (N-decylaldehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3...

Synthesis and potential cytotoxic activity of some new benzoxazoles, imidazoles, benzimidazoles and tetrazoles.

PubMed

Arulmurugan, Subramaniyan; Kavitha, Helen P

2013-06-01

2 The present work deals with the synthesis of some novel heterocyclic compounds such as benzoxazoles , 7, 13 and 19, imidazoles 3, 8, 14 and 20, benzimidazoles 4, 9, 15 and 21, and tetrazoles 10, 16, and 22. The synthesized compounds were characterized by IR, 1H NMR, mass spectrometry and elemental analysis. The compounds were evaluated for cytotoxicity against human cancer cell lines such as MCF-7 (breast cancer) and HT-29 (colon cancer) by the MTT assay method. Among the tested compounds, 4,4'-sulfonylbis(N-(2-(1H-benzo[d]imidazol- -2-yl)ethyl)aniline (9), N-bis(2-(benzo[d]oxazol-2-yl)-ethyl)- 6-phenyl-1,3,5-triazine-2,4-diamine (13), N-bis(2-(1H-benzo[ d]imidazol-2-yl)ethyl)-6-phenyl-1,3,5-triazine-2,4-diamine (15) and N-tris(2-1H-benzo[d]imidazol-2-yl)ethyl)- 1,3,5-triazine-2,4,6-triamine (21) showed potent cytotoxicity.

New cysteamine (2-chloroethyl)nitrosoureas. Synthesis and preliminary antitumor results.

PubMed

Madelmont, J C; Godeneche, D; Parry, D; Duprat, J; Chabard, J L; Plagne, R; Mathe, G; Meyniel, G

1985-09-01

Three chemical pathways were used for the synthesis of four new N'-(2-chloroethyl)-N-[2-(methylsulfinyl)ethyl]- and N'-(2-chloroethyl)-N-[2-(methylsulfonyl)ethyl]-N- or N'-nitrosoureas. These compounds are plasma metabolites of CNCC, a promising antineoplastic (2-chloroethyl)nitrosourea. Preliminary antitumor evaluation was performed against L1210 leukemia implanted intraperitoneally in mice. Among these compounds, two of them exhibited a greater antitumor activity compared to that of the parent mixture.

The effect of structurally related impurities on crystallinity reduction of sulfamethazine by grinding.

PubMed

Hamada, Yoshito; Ono, Makoto; Ohara, Motomu; Yonemochi, Etsuo

2016-12-30

In this study, the effect of structurally related impurities on crystallinity reduction of sulfamethazine by grinding was evaluated. The crystallinity of sulfamethazine was not decreased when it was ground alone. However, when structurally related impurities with sulfonamide derivatives were blended, the crystallinity of sulfamethazine was decreased by grinding. Other materials without a sulfonamide moiety showed no such effect. The Raman spectra of sulfamethazine demonstrated that there was a difference between its crystalline and amorphous states within its sulfonamide structure. It was suggested that the sulfonamide structure of the impurities was important in causing the inhibition of recrystallization of sulfamethazine during grinding. Copyright © 2016 Elsevier B.V. All rights reserved.

N-(3-Chloro-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2013-10-12

In the title compound, C14H12ClN3O3S, the fused five- and six-membered rings are folded slightly along the common edge, forming a dihedral angle of 3.2 (1)°. The mean plane through the indazole system makes a dihedral angle of 30.75 (7)° with the distant benzene ring. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, forming a two-dimensional network parallel to (001).

Prevalence and characterization of plasmids carrying sulfonamide resistance genes among Escherichia coli from pigs, pig carcasses and human

PubMed Central

2010-01-01

Background Sulfonamide resistance is very common in Escherichia coli. The aim of this study was to characterize plasmids carrying sulfonamide resistance genes (sul1, sul2 and sul3) in E. coli isolated from pigs and humans with a specific objective to assess the genetic diversity of plasmids involved in the mobility of sul genes. Methods A total of 501 E. coli isolates from pig feces, pig carcasses and human stools were tested for their susceptibility to selected antimicrobial. Multiplex PCR was conducted to detect the presence of three sul genes among the sulfonamide-resistant E. coli isolates. Fifty-seven sulfonamide-resistant E. coli were selected based on presence of sul resistance genes and subjected to conjugation and/or transformation experiments. S1 nuclease digestion followed by pulsed-field gel electrophoresis was used to visualize and determine the size of plasmids. Plasmids carrying sul genes were characterized by PCR-based replicon typing to allow a comparison of the types of sul genes, the reservoir and plasmid present. Results A total of 109/501 isolates exhibited sulfonamide resistance. The relative prevalences of sul genes from the three reservoirs (pigs, pig carcasses and humans) were 65%, 45% and 12% for sul2, sul1, and sul3, respectively. Transfer of resistance through conjugation was observed in 42/57 isolates. Resistances to streptomycin, ampicillin and trimethoprim were co-transferred in most strains. Class 1 integrons were present in 80% of sul1-carrying plasmids and 100% of sul3-carrying plasmids, but only in 5% of sul2-carrying plasmids. The sul plasmids ranged from 33 to 160-kb in size and belonged to nine different incompatibility (Inc) groups: FII, FIB, I1, FIA, B/O, FIC, N, HI1 and X1. IncFII was the dominant type in sul2-carrying plasmids (52%), while IncI1 was the most common type in sul1 and sul3-carrying plasmids (33% and 45%, respectively). Multireplicons were found associated with all three sul genes. Conclusions Sul genes were distributed widely in E. coli isolated from pigs and humans with sul2 being most prevalent. Sul-carrying plasmids belonged to diverse replicon types, but most of detected plasmids were conjugative enabling horizontal transfer. IncFII seems to be the dominant replicon type in sul2-carrying plasmids from all three sources. PMID:20670455

Usefulness of Icosapent Ethyl (Eicosapentaenoic Acid Ethyl Ester) in Women to Lower Triglyceride Levels (Results from the MARINE and ANCHOR Trials).

PubMed

Mosca, Lori; Ballantyne, Christie M; Bays, Harold E; Guyton, John R; Philip, Sephy; Doyle, Ralph T; Juliano, Rebecca A

2017-02-01

There are limited data on the efficacy and safety of triglyceride (TG)-lowering agents in women. We conducted subgroup analyses of the effects of icosapent ethyl (a high-purity prescription form of the ethyl ester of the omega-3 fatty acid, eicosapentaenoic acid) on TG levels (primary efficacy variable) and other atherogenic and inflammatory parameters in a total of 215 women with a broad range of TG levels (200-2000 mg/dl) enrolled in two 12-week placebo-controlled trials: MARINE (n = 18; placebo, n = 18) and ANCHOR (n = 91; placebo, n = 88). Icosapent ethyl 4 g/day significantly reduced TG levels from baseline to week 12 versus placebo in both MARINE (-22.7%; p = 0.0327) and ANCHOR (-21.5%; p <0.0001) without increasing low-density lipoprotein cholesterol levels. Significant improvements were also observed in non-high-density lipoprotein cholesterol levels in MARINE (-15.7%; p = 0.0082) and ANCHOR (-14.2%; p <0.0001) and total cholesterol levels in MARINE (-14.9%; p = 0.0023) and ANCHOR (-12.1%; p <0.0001), along with significant increases of >500% in eicosapentaenoic acid levels in plasma and red blood cells (all p <0.001). Icosapent ethyl was well tolerated, with adverse-event profiles comparable with findings in the overall studies. In conclusion, icosapent ethyl 4 g/day significantly reduced TG levels and other atherogenic parameters in women without increasing low-density lipoprotein cholesterol levels compared with placebo; the clinical implications of these findings are being evaluated in the REDUCtion of Cardiovascular Events With Eicosapentaenoic Acid [EPA]-Intervention Trial (REDUCE-IT) cardiovascular outcomes study. Copyright © 2016 The Author(s). Published by Elsevier Inc. All rights reserved.

Synthesis and Properties of the p-Sulfonamide Analogue of the Green Fluorescent Protein (GFP) Chromophore: The Mimic of GFP Chromophore with Very Strong N-H Photoacid Strength.

PubMed

Chen, Yi-Hui; Sung, Robert; Sung, Kuangsen

2018-04-06

The para-sulfonamide analogue ( p-TsABDI) of a green fluorescent protein (GFP) chromophore was synthesized to mimic the GFP chromophore. Its S 1 excited-state p K a * value in dimethylsulfoxide (DMSO) is -1.5, which is strong enough to partially protonate dipolar aprotic solvents and causes excited-state proton transfer (ESPT), so it can partially mimic the GFP chromophore to further study the ESPT-related photophysics and the blinking phenomenon of GFP. In comparison with 8-hydroxypyrene-1,3,6-trisulfonate (HPTS) (p K a = 7.4, p K a * = 1.3 in water), p-TsABDI (p K a = 6.7, p K a * = -1.5 in DMSO) is a better photoacid for pH-jump studies.

Removal of nutrients and veterinary antibiotics from swine wastewater by a constructed macrophyte floating bed system.

PubMed

Xian, Qiming; Hu, Lixia; Chen, Hancheng; Chang, Zhizhou; Zou, Huixian

2010-12-01

The potential of three varieties of Italian ryegrass (Lolium multiflorum Lam.), Dryan, Tachimasari and Waseyutaka, to improve the water quality of swine wastewater was evaluated using a constructed macrophyte floating bed system. With respect to reductions in levels of nutrients, chemical oxygen demand (COD), and sulfonamide antimicrobials (SAs, including sulfadiazine, sulfamethazine, and sulfamethoxazole), Dryan performed better than Tachimasari and Waseyutaka. For Dryan, total N was reduced by 84.0%, total P by 90.4%, COD by 83.4% and sulfonamide antimicrobials by 91.8-99.5%. Similar results were observed for Tachimasari and Waseyutaka. The results indicated that the treatment of swine wastewater using the constructed macrophyte floating bed system was effective in the removal of nutrients and veterinary antibiotics. Copyright © 2010 Elsevier Ltd. All rights reserved.

Effect of humic acid (HA) on sulfonamide sorption by biochars.

PubMed

Lian, Fei; Sun, Binbin; Chen, Xi; Zhu, Lingyan; Liu, Zhongqi; Xing, Baoshan

2015-09-01

Effect of quantity and fractionation of loaded humic acid (HA) on biochar sorption for sulfonamides was investigated. The HA was applied in two different modes, i.e. pre-coating and co-introduction with sorbate. In pre-coating mode, the polar fractions of HA tended to interact with low-temperature biochars via H-bonding, while the hydrophobic fractions were likely to be adsorbed by high-temperature biochars through hydrophobic and π-π interactions, leading to different composition and structure of the HA adlayers. The influences of HA fractionation on biochar sorption for sulfonamides varied significantly, depending on the nature of interaction between HA fraction and sorbate. Meanwhile, co-introduction of HA with sulfonamides revealed that the effect of HA on sulfonamide sorption was also dependent on HA concentration. These findings suggest that the amount and fractionation of adsorbed HA are tailored by the surface properties of underlying biochars, which differently affect the sorption for organic contaminants. Copyright © 2015 Elsevier Ltd. All rights reserved.

Sulfonamide chalcones: Synthesis and in vitro exploration for therapeutic potential against Brugia malayi.

PubMed

Bahekar, Sandeep P; Hande, Sneha V; Agrawal, Nikita R; Chandak, Hemant S; Bhoj, Priyanka S; Goswami, Kalyan; Reddy, M V R

2016-11-29

Keeping in mind the immense biological potential of chalcones and sulfonamide scaffolds, a library of sulfonamide chalcones has been synthesized and evaluated for in vitro antifilarial assay against human lymphatic filarial parasite Brugia malayi. Experimental evidence showcased for the first time the potential of some sulfonamide chalcones as effective and safe antifilarial lead molecules against human lymphatic filarial parasite B. malayi. Sulfonamide chalcones 4d, 4p, 4q, 4t and 4aa displayed the significantly wide therapeutic window. Particularly chalcones with halogen substitution in aromatic ring proved to be potent antifilarial agents against Brugia malayi. Sulphonamide chalcones with lipophilic methyl moiety (4q and 4aa) at para position of terminal phenyl rings of compounds were found to have remarkable antifilarial activities with therapeutic efficacy. Observed preliminary evidence of apoptosis by effective chalcone derivatives envisaged its fair possibility to inhibit folate pathway with consequent defect in DNA synthesis. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Highly sensitive sites for guanine-O6 ethylation in rat brain DNA exposed to N-ethyl-N-nitrosourea in vivo.

PubMed Central

Nehls, P; Rajewsky, M F; Spiess, E; Werner, D

1984-01-01

Brain chromosomal DNA isolated from fetal BDIX-rats 1 h after i.v. administration of the ethylating N-nitroso carcinogen N-ethyl-N-nitrosourea (75 micrograms/g body weight), statistically contained one molecule of O6-ethyl-2'-deoxyguanosine (O6-EtdGuo) per 81 micron of DNA, as determined in enzymatic DNA hydrolysates by competitive radio-immunoassay using a high-affinity anti-(O6-EtdGuo) monoclonal antibody (ER-6). After fragmentation of the DNA by the restriction enzyme AluI (average fragment length, Lav = 0.28 micron = 970 bp; length range, Lr = 1.87-0.02 micron = 6540 - 60 bp), a small (approximately 2%) fraction of DNA enriched in specific polypeptides tightly associated with DNA was separated from the bulk DNA by a glass fiber binding technique. As analyzed by immune electron microscopy, approximately 1% of the DNA molecules in this fraction contained clusters of 2-10 (O6-EtdGuo)-antibody binding sites (ABS). On the cluster-bearing fragments (Lav, 0.85 micron +/- 0.50 micron S.D.; corresponding to 2970 +/- 1760 bp) the average ABS-ABS interspace distance was 110 nm (= 390 bp; range approximately 9-600 nm), indicating a highly non-random distribution of O6-EtdGuo in target cell DNA. Images Fig. 2. PMID:6370677

Biodegradation of sulfamethazine by Trametes versicolor: Removal from sewage sludge and identification of intermediate products by UPLC-QqTOF-MS.

PubMed

García-Galán, Ma Jesús; Rodríguez-Rodríguez, Carlos E; Vicent, Teresa; Caminal, Gloria; Díaz-Cruz, M Silvia; Barceló, Damià

2011-11-15

Degradation of the sulfonamide sulfamethazine (SMZ) by the white-rot fungus Trametes versicolor was assessed. Elimination was achieved to nearly undetectable levels after 20 h in liquid medium when SMZ was added at 9 mg L(-1). Experiments with purified laccase and laccase-mediators resulted in almost complete removal. On the other hand, inhibition of SMZ degradation was observed when piperonilbutoxide, a cytochrome P450-inhibitor, was added to the fungal cultures. UPLC-QqTOF-MS analysis allowed the identification and confirmation of 4 different SMZ degradation intermediates produced by fungal cultures or purified laccase: desulfo-SMZ, N4-formyl-SMZ, N4-hydroxy-SMZ and desamino-SMZ; nonetheless SMZ mineralization was not demonstrated with the isotopically labeled sulfamethazine-phenyl-13C6 after 7 days. Inoculation of T. versicolor to sterilized sewage sludge in solid-phase systems showed complete elimination of SMZ and also of other sulfonamides (sulfapyridine, sulfathiazole) at real environmental concentrations, making this fungus an interesting candidate for further remediation research. Copyright © 2011 Elsevier B.V. All rights reserved.

A structure-based virtual screening approach toward the discovery of histone deacetylase inhibitors: identification of promising zinc-chelating groups.

PubMed

Park, Hwangseo; Kim, Sukyoung; Kim, Yong Eun; Lim, Soo-Jeong

2010-04-06

The inhibitors of histone deacetylases (HDACs) have drawn a great deal of attention due to their promising potential as small-molecule therapeutics for the treatment of cancer. By means of virtual screening with docking simulations under consideration of the effects of ligand solvation, we were able to identify six novel HDAC inhibitors with IC(50) values ranging from 1 to 100 muM. These newly identified inhibitors are structurally diverse and have various chelating groups for the active site zinc ion, including N-[1,3,4]thiadiazol-2-yl sulfonamide, N-thiazol-2-yl sulfonamide, and hydroxamic acid moieties. The former two groups are included in many drugs in current clinical use and have not yet been reported as HDAC inhibitors. Therefore, they can be considered as new inhibitor scaffolds for the development of anticancer drugs by structure-activity relationship studies to improve the inhibitory activities against HDACs. Interactions with the HDAC1 active site residues responsible for stabilizing these new inhibitors are addressed in detail.

Antineoplastic Efficacy of Novel Polyamine Analogues in Human Breast Cancer

DTIC Science & Technology

2005-06-01

Davidson, N.E., and Casero, R.A.. Spermine oxidase SMO(PAOh1), not N1-acetylpolyamine oxidase (PAO) is the primary source of cytotoxic H2O2 in polyamine... spermine oxidase (PAOh1/SMO) mRNA and activity by a polyamine analogue in human breast cancer cell lines. The fourth Era of Hope meeting for the...SMO/PAOh1 Spermine Oxidase DFMO α-difluoromethylornithine BENSpm N1, N11-bis(ethyl)norspermine CHEMSpm N1-(cycloheptylmethyl)-N11-ethyl- 4,8

40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

Code of Federal Regulations, 2011 CFR

2011-07-01

...-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur...)amino]ethyl], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1...

40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

Code of Federal Regulations, 2010 CFR

2010-07-01

...-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur...)amino]ethyl], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1...

40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

Code of Federal Regulations, 2013 CFR

2013-07-01

...-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur...)amino]ethyl], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1...

Adsorption of acetanilide herbicides on soil and its components. II. Adsorption and catalytic hydrolysis of diethatyl-ethyl on saturated Na(+)-, K(+)-, Ca(2+)-, and Mg(2+)-montmorillonite.

PubMed

Liu, W P; Fang, Z; Liu, H J; Yang, W C

2001-04-01

Adsorption and catalytic hydrolysis of the herbicide diethatyl-ethyl [N-chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester] on homoionic Na(+)-, K(+)-, Ca(2+)-, and Mg(2+)-montmorillonite clays were investigated in water solution. The Freundlich adsorption coefficient, Ki, got from isotherms on clay followed the order of Na+ approximately K+ > Mg2+ approximately Ca2+. Analysis of FT-IR spectra of diethatyl-ethyl adsorbed on clay suggests probable bonding at the carboxyl and amide carbonyl groups of the herbicide. The rate of herbicide hydrolysis in homoionic clay suspensions followed the same order as that for adsorption, indicating that adsorption may have preceded and thus caused hydrolysis. Preliminary product identification showed that hydrolysis occurred via nucleophilic substitution at the carboxyl carbon, causing the cleavage of the ester bond and formation of diethatyl and its dechlorinated derivative, and at the amide carbon, yielding an ethyl ester derivative and its acid. These pathways also suggest that hydrolysis of diethatyl-ethyl was catalyzed by adsorption on the clay surface.

“Click, Click, Cyclize”: A DOS Approach to Sultams Utilizing Vinyl Sulfonamide Linchpins

PubMed Central

Zhou, Aihua; Rayabarapu, Dinesh; Hanson, Paul R.

2009-01-01

A diversity-oriented synthesis (DOS) strategy termed “Click, Click, Cyclize” is reported. This approach relies on functional group (FG) pairing between a vinyl sulfonamide and an array of functional groups to synthesize skeletally diverse sultams. Several FG pairing pathways on central tertiary vinyl sulfonamide linchpins have been developed including intramolecular Heck, aza-Michael, ring-closing enyne metathesis, Pauson—Khand, and chemoselective oxidation/Baylis—Hillman reactions. PMID:19115841

Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors.

PubMed

Sapegin, Alexander; Kalinin, Stanislav; Angeli, Andrea; Supuran, Claudiu T; Krasavin, Mikhail

2018-02-01

4-Chloro-3-nitrobenzenesulfonamide reacted cleanly at room-temperature with a range of bis-electrophilic phenols bearing an NH-acidic functionality (secondary carboxamide or pyrazole) in the ortho-position. This produced a novel class of [1,4]oxazepine-based primary sulfonamides which exhibited strong inhibition of therapeutically relevant human carbonic anhydrases. 2-Chloronitrobenzene did not enter a similar cyclocondensation process, even under prolonged heating. Thus, the primary sulfonamide functionality plays a dual role by enabling the [1,4]oxazepine ring construction and acting as a enzyme prosthetic zinc-binding group when the resulting [1,4]oxazepine sulfonamides are employed as carbonic anhydrase inhibitors. Copyright © 2017 Elsevier Inc. All rights reserved.

Antimalarial activity of compounds comprising a primary benzene sulfonamide fragment.

PubMed

Andrews, Katherine T; Fisher, Gillian M; Sumanadasa, Subathdrage D M; Skinner-Adams, Tina; Moeker, Janina; Lopez, Marie; Poulsen, Sally-Ann

2013-11-15

Despite the urgent need for effective antimalarial drugs with novel modes of action no new chemical class of antimalarial drug has been approved for use since 1996. To address this, we have used a rational approach to investigate compounds comprising the primary benzene sulfonamide fragment as a potential new antimalarial chemotype. We report the in vitro activity against Plasmodium falciparum drug sensitive (3D7) and resistant (Dd2) parasites for a panel of fourteen primary benzene sulfonamide compounds. Our findings provide a platform to support the further evaluation of primary benzene sulfonamides as a new antimalarial chemotype, including the identification of the target of these compounds in the parasite. Copyright © 2013 Elsevier Ltd. All rights reserved.

Degradation mechanism of alachlor during direct ozonation and O(3)/H(2)O(2) advanced oxidation process.

PubMed

Qiang, Zhimin; Liu, Chao; Dong, Bingzhi; Zhang, Yalei

2010-01-01

The degradation of alachlor by direct ozonation and advanced oxidation process O(3)/H(2)O(2) was investigated in this study with focus on identification of degradation byproducts. The second-order reaction rate constant between ozone and alachlor was determined to be 2.5+/-0.1M(-1)s(-1) at pH 7.0 and 20 degrees C. Twelve and eight high-molecular-weight byproducts (with the benzene ring intact) from alachlor degradation were identified during direct ozonation and O(3)/H(2)O(2), respectively. The common degradation byproducts included N-(2,6-diethylphenyl)-methyleneamine, 8-ethyl-3,4-dihydro-quinoline, 8-ethyl-quinoline, 1-chloroacetyl-2-hydro-3-ketone-7-acetyl-indole, 2-chloro-2',6'-diacetyl-N-(methoxymethyl)acetanilide, 2-chloro-2'-acetyl-6'-ethyl-N-(methoxymethyl)-acetanilide, and two hydroxylated alachlor isomers. In direct ozonation, four more byproducts were also identified including 1-chloroacetyl-2,3-dihydro-7-ethyl-indole, 2-chloro-2',6'-ethyl-acetanilide, 2-chloro-2',6'-acetyl-acetanilide and 2-chloro-2'-ethyl-6'-acetyl-N-(methoxymethyl)-acetanilide. Degradation of alachlor by O(3) and O(3)/H(2)O(2) also led to the formation of low-molecular-weight byproducts including formic, acetic, propionic, monochloroacetic and oxalic acids as well as chloride ion (only detected in O(3)/H(2)O(2)). Nitrite and nitrate formation was negligible. Alachlor degradation occurred via oxidation of the arylethyl group, N-dealkylation, cyclization and cleavage of benzene ring. After O(3) or O(3)/H(2)O(2) treatment, the toxicity of alachlor solution examined by the Daphnia magna bioassay was slightly reduced. 2009 Elsevier Ltd. All rights reserved.

Antioxidant potential of n-butanol fraction from extract of Jasminum mesnyi Hance leaves.

PubMed

Borar, Sakshi; Punia, Priyanka; Kalia, A N

2011-01-01

Methanolic extract of Jasminum mesnyi Hance leaves having antidiabetic activity was subjected to fractionation to obtain antioxidant and antihyperglycemic rich fraction. Different concentrations of ethyl acetate and n-butanol fractions were subjected to antioxidant assay by DPPH method, nitric oxide scavenging activity and reducing power assay. The fractions showed dose dependent free radical scavenging property in all the models. IC50 values for ethyl acetate and n-butanol fractions were 153.45 +/- 6.65 and 6.22 +/- 0.25 microg/ml, respectively, as compared to L-ascorbic acid and rutin (as standards; IC50 values 6.54 +/- 0.24 and 5.43 +/- 0.21 microg/ml, respectively) in DPPH model. In nitric oxide scavenging activity, IC50 values were 141.54 +/- 9.95 microg/ml, 35.12 +/- 1.58 microg/ml, 21.06 +/- 0.95 microg/ml and 29.93 +/- 0.32 microg/ml for ethyl acetate, n-butanol fractions, L-ascorbic acid and rutin, respectively. n-Butanol fraction showed a good reducing potential and better free radical scavenging activity as compared to ethyl acetate fraction. Potent antioxidant n-butanol fraction showed better oral glucose tolerance test (antihyperglycemic) at par with metformin (standard drug), n-Butanol fraction contained secoiridoid glycosides which might be responsible for both antioxidant and antihyperglycemic activity.

The DoD Environmental Restoration Program: An Air Force Perspective and Status Update

DTIC Science & Technology

2011-11-01

PFCs of interest Perfluorooctane sulfonate ( PFOS ) Perfluorooctanoic acid ( PFOA ) C8HF17O3S C8HF15O2 I n t e g r i t y - S...Mixtures Change in science/methods Evaluation in progress Perchlorate Lower regulatory standards Continue to monitor PFCs ( PFOS / PFOA ) Regulatory interest...e 25 DoD Activities: PFCs PFOA / PFOS on the DoD Emerging Contaminant Watch List for continued surveillance of regulatory actions SERDP

Analysis of fatty acid ethyl esters in hair as possible markers of chronically elevated alcohol consumption by headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS).

PubMed

Pragst, F; Auwaerter, V; Sporkert, F; Spiegel, K

2001-09-15

Fatty acid ethyl esters (FAEE) are products of the nonoxidative ethanol metabolism, which are known to be detectable in blood only about 24h after the last alcohol intake. After deposition in hair they should be suitable long-term markers of chronically elevated alcohol consumption. Therefore, a method for the analysis of ethyl myristate, ethyl palmitate, ethyl oleate and ethyl stearate from hair was developed based on the extraction of the hair sample by a dimethylsulphoxide (DMSO)/n-hexane mixture, separation and evaporation of the n-hexane phase and application of headspace solid-phase microextraction (HS-SPME) in combination with gas chromatography-mass spectrometry (GC-MS) to the extract. For use as internal standards, the corresponding D(5)-ethyl esters were prepared. The HS-SPME/GC-MS measurements were automatically performed using a multi-purpose sampler. The detection limits of the FAEE were between 0.01 and 0.04ng/mg and the reproducibility was between 3.5 and 16%. By application of the method to hair samples of 21 fatalities with known heavy alcohol abuse 0.045-2.4ng/mg ethyl myristate, 0.35-13.5ng/mg ethyl palmitate, 0.25-7.7ng/mg ethyl oleate and 0.05-3.85ng/mg ethyl stearate were measured. For social drinkers (30-60g ethanol per week), the concentrations were about one order of magnitude smaller. For 10 teetotalers negative results or traces of ethyl palmitate were found. It was shown by supplementary investigations in single cases that FAEE are also present in sebum, that there is no strong difference in their concentrations between pubic, chest and scalp hair, and that they are detectable in hair segments after a 2 months period of abstinence. From the results follows that the measurement of FAEE concentrations in hair is a useful way for a retrospective detection of alcohol abuse.

Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.

PubMed

Czeizel, Andrew E; Puhó, Erzsébet; Sørensen, Henrik T; Olsen, Jørn

2004-06-01

The objective of the study presented here was to check the debated human teratogenic potential of sulfonamide drugs. Five different sulfonamides such as sulfamethazine, sulfathiourea, sulfamethoxypyridazine, sulfamethoxydiazine and the combination of sulfamethazine-sulfathiourea-sulfamethoxypyridazine were differentiated. Cases with congenital abnormalities were compared with their matched controls without congenital abnormalities in the population-based large data set of the Hungarian Case-Control Surveillance of Congenital Abnormalities between 1980 and 1996. Of 38,151 newborn infants without any congenital abnormalities (control group), 163 (0.4%) had mothers who were treated with the sulfonamides studied during pregnancy, while of 22,843 cases with congenital abnormalities, 140 (0.6%) had mothers who were treated with the sulfonamides studied during pregnancy. The analysis of cases and matched controls indicated a higher rate of cardiovascular malformation (adjusted prevalence odds ratios [POR] with 95% CI: 3.5, 1.9-6.4) and clubfoot (adjusted POR with 95% CI: 2.6, 1.1-6.2) in infants born to mothers with sulfonamide treatment in the second and third months of pregnancy. The detailed analysis of different sulfonamides showed a possible association between cardiovascular malformations (adjusted POR with 95%; CI: 6.5, 2.6-15.9), particularly ventricular septal defect (17.1, 1.3-141.1) and sulfamethoxydiazine during the second and third months of pregnancy. In addition, a possible association was found between clubfoot and sulfathiourea, both during the entire pregnancy (adjusted POR with 95% CI: 2.3, 1.2-4.3) and in the second and third months of gestation (3.9, 1.1-13.8). Thus, maternal treatment of sulfamethoxydiazine may cause ventricular septal defect, while sulfathiourea may induce clubfoot; however, further studies are needed to verify or reject these associations.

Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate

PubMed Central

2016-01-01

A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides. PMID:26065317

Calf antibiotic and sulfonamide test (CAST) for screening antibiotic and sulfonamide residues in calf carcasses.

PubMed

Dey, Bhabani P; Reamer, Richard P; Thaker, Nitin H; Thaler, Alice M

2005-01-01

The Calf Antibiotic and Sulfonamide Test (CAST), a microbial inhibition screening test, was developed for detecting antibiotics and sulfonamides in bob veal calf carcasses. The test uses Bacillus megaterium ATCC 9885 as the indicator organism and Mueller Hinton agar as the growth medium. Compared to Swab Test on Premises (STOP), developed in 1970, this screening test has higher sensitivity and the ability to detect a wider range of veterinary antimicrobial residual drugs, particularly sulfonamides, at lower concentrations. Carcasses that are tested with CAST and suspected of containing chemical residue above tolerance level are retained for confirmation. Disposition of these carcasses are determined upon laboratory result. Routine testing of bob veal calves with CAST allowed the Food Safety and Inspection Service to release most calf carcasses within 24 h post-slaughter, thus conserving shipping and handling resources. However, changes in the regulation in 1990 dictate that disposition of carcasses found to contain violative levels of sulfonamide residues should be based on laboratory findings. The analysis of the data for the years 1990-1994 and 1998 indicate that the use of CAST over the years was significant, and had a direct impact on reduction of residue violations in veal carcasses. With the use of CAST, potentially harmful antimicrobial chemicals entering the human food chain through veal meat have been minimized.

Investigation of Antigen-Antibody Interactions of Sulfonamides with a Monoclonal Antibody in a Fluorescence Polarization Immunoassay Using 3D-QSAR Models

PubMed Central

Wang, Zhanhui; Kai, Zhenpeng; Beier, Ross C.; Shen, Jianzhong; Yang, Xinling

2012-01-01

A three-dimensional quantitative structure-activity relationship (3D-QSAR) model of sulfonamide analogs binding a monoclonal antibody (MAbSMR) produced against sulfamerazine was carried out by Distance Comparison (DISCOtech), comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA). The affinities of the MAbSMR, expressed as Log10IC50, for 17 sulfonamide analogs were determined by competitive fluorescence polarization immunoassay (FPIA). The results demonstrated that the proposed pharmacophore model containing two hydrogen-bond acceptors, two hydrogen-bond donors and two hydrophobic centers characterized the structural features of the sulfonamides necessary for MAbSMR binding. Removal of two outliers from the initial set of 17 sulfonamide analogs improved the predictability of the models. The 3D-QSAR models of 15 sulfonamides based on CoMFA and CoMSIA resulted in q2 cv values of 0.600 and 0.523, and r2 values of 0.995 and 0.994, respectively, which indicates that both methods have significant predictive capability. Connolly surface analysis, which mainly focused on steric force fields, was performed to complement the results from CoMFA and CoMSIA. This novel study combining FPIA with pharmacophore modeling demonstrates that multidisciplinary research is useful for investigating antigen-antibody interactions and also may provide information required for the design of new haptens. PMID:22754368

[Occurrence of quinolone and sulfonamide antibiotics in swine and cattle manures from large-scale feeding operations of Guangdong Province].

PubMed

Tai, Yi-Ping; Luo, Xiao-Dong; Mo, Ce-Hui; Li, Yan-Wen; Wu, Xiao-Lian; Liu, Xing-Yue

2011-04-01

The occurrence and distribution of four quinolones and four sulfonamides in swine and cattle feces sampled from twenty large-scale feeding operations in different areas of Guangdong province were detected using solid phase extraction (SPE) and high performance liquid chromatography (HPLC). Quinolone and sulfonamide compounds were observed in all pig dung samples. Their total concentrations ranged from 24.5 microg/kg to 1516.2 microg/kg (F. W.) with an average of 581.0 microg/kg and ranged from 1925.9-13399.5 microg/kg with an average of 4403.9 microg/kg respectively. The dominant compounds in pig feces were ciprofloxacin and enrofloxacin for quinolones and sulfamerazine and sulfamethoxazole for sulfonamides. Quinolone compounds which dominated with norfloxacin and ciprofloxacin were also observed in all cattle dung samples, its total concentrations ranged from 73.2 microg/kg to 1328.0 microg/kg which averaged 572.9 microg/kg. While the positive rates of sulfonamide compounds detected in cattle dung samples were above 90%, predominated by sulfamethoxazole and sulfamerazine. Concentration and distribution of both quinolone and sulfonamide compounds in swine and cattle dungs of different feeding operations varied greatly. Relatively high concentrations of the two kinds of antibiotics were found in both swine and cattle dungs from Guangzhou area, while sulfameter and sulfamethazine in cattle dungs from Foshan and Shenzhen areas were below the limit of detection.

Ethyl pyruvate inhibits hypoxic pulmonary vasoconstriction and attenuates pulmonary artery cytokine expression

PubMed Central

Tsai, Ben M.; Lahm, Tim; Morrell, Eric D.; Crisostomo, Paul R.; Markel, Troy; Wang, Meijing; Meldrum, Daniel R.

2009-01-01

Hypoxic pulmonary vasoconstriction is a common consequence of acute lung injury and may be mediated by increased local production of proinflammatory cytokines. Ethyl pyruvate is a novel anti-inflammatory agent that has been shown to downregulate proinflammatory genes following hemorrhagic shock; however, its effects on hypoxic pulmonary vasoconstriction are unknown. We hypothesized that ethyl pyruvate would inhibit hypoxic pulmonary vasoconstriction and downregulate pulmonary artery cytokine expression during hypoxia. To study this, isometric force displacement was measured in isolated rat pulmonary artery rings (n=8/group) during hypoxia (95% N2/5% CO2) with or without prior ethyl pyruvate (10 mM) treatment. Following 60 minutes of hypoxia, pulmonary artery rings were analyzed for TNF-α and IL-1 mRNA via RT-PCR. Ethyl pyruvate inhibited hypoxic pulmonary artery contraction (4.49±2.32% vs. 88.80±5.68% hypoxia alone) and attenuated the hypoxic upregulation of pulmonary artery TNF and IL-1 mRNA (p<0.05). These data indicate that: 1) hypoxia increases pulmonary artery vasoconstriction and proinflammatory cytokine gene expression; 2) ethyl pyruvate decreases hypoxic pulmonary vasoconstriction and downregulates hypoxia-induced pulmonary artery proinflammatory cytokine gene expression; and 3) ethyl pyruvate may represent a novel therapeutic adjunct in the treatment of acute lung injury. PMID:17574585

Towards further understanding on the antioxidative activities of Prunus persica fruit: A comparative study with four different fractions

NASA Astrophysics Data System (ADS)

Dhingra, Naveen; Sharma, Rajesh; Kar, Anand

2014-11-01

In the present study we have evaluated the antioxidant activities of different fractions (hexane, ethyl acetate, n-butanol and aqueous fractions) of Prunus persica fruit. For extraction simple warring blender method was employed and total phenolic and flavonoid contents were correlated with different antioxidant activities (total antioxidant, 2,2-diphenyl-1-picrylhydrazyl (DPPH), H2O2 scavenging, superoxide radical scavenging, iron chelating and their reducing power properties). Different in vitro antioxidant studies showed that ethyl acetate and n-butanol fractions had the maximum activities that were well correlated with total phenolic and flavonoid contents. Maximum yield (25.14 ± 2.2%) was obtained in its aqueous fraction. Both ethyl acetate and n-butanol fractions showed significant inhibitory effects on different antioxidant activities. A significantly high correlation coefficient existed between total antioxidant activities and with total phenolic as well as total flavonoid contents. It appears that ethyl acetate and n-butanol fractions of P. persica may serve as new potential sources of natural antioxidants and could be of therapeutic use in treating several diseases.

Rapid method for quantification of nine sulfonamides in bovine milk using HPLC/MS/MS and without using SPE.

PubMed

Nebot, Carolina; Regal, Patricia; Miranda, Jose Manuel; Fente, Cristina; Cepeda, Alberto

2013-12-01

Sulfonamides are antimicrobial agents widely employed in animal production and their residues in food could be an important risk to human health. In the dairy industry, large quantities of milk are monitored daily for the presence of sulfonamides. A simple and low-cost extraction protocol followed by a liquid chromatographic-tandem mass spectrometry method was developed for the simultaneous detection of nine sulfonamides in whole milk. The method was validated at the maximum residue limits established by European legislation. The limits of quantification obtained for most sulfonamides were between 12.5 and 25 μg kg(-1), detection capabilities ranged from 116 to 145 μg kg(-1), and recoveries, at 100 μg kg(-1), were greater than 89±12.5%. The method was employed to analyse 100 raw whole bovine milk samples collected from dairy farms in the northwest region of Spain. All of the samples were found to be compliant, but two were positive; one for sulfadiazine and the other for sulfamethoxipyridazine. Copyright © 2013 Elsevier Ltd. All rights reserved.

THE INHIBITION OF THE BACTERIOSTATIC ACTION OF SULFONAMIDE DRUGS BY SUBSTANCES OF ANIMAL AND BACTERIAL ORIGIN

PubMed Central

MacLeod, Colin M.

1940-01-01

Sulfonamide inhibitor has been demonstrated in extracts of fresh normal muscle, pancreas, and spleen of certain animals. When autolysis of tissues takes place the amount of inhibitor is greatly increased. Fresh liver from beef, rabbit, and guinea pig is free of active inhibitor, although inhibitor is demonstrable in autolysates of this tissue. Fresh rabbit kidney is likewise free of active inhibitor. Following acid hydrolysis extracts of fresh rabbit liver and kidney cause sulfonamide inhibition. Normal human urine contains little or no active inhibitor. However, upon acid hydrolysis, inhibitor is uniformly present. Sulfonamide inhibitor is present in some, but not all, sterile serous effusions occurring during certain diseases. Inhibitor was found uniformly in pus. None was found in blood serum. In certain species of bacteria the inhibitor is found in the cells only and is not demonstrable in the culture medium, whereas in other species, the inhibitor is found in the culture supernatant, and the cells themselves are relatively free. The development of sulfapyridine fastness in a strain of Pneumococcus Type I is accompanied by a greatly increased production of sulfonamide inhibitor. PMID:19871019

Discovery of glycine sulfonamides as dual inhibitors of sn-1-diacylglycerol lipase α and α/β-hydrolase domain 6.

PubMed

Janssen, Freek J; Deng, Hui; Baggelaar, Marc P; Allarà, Marco; van der Wel, Tom; den Dulk, Hans; Ligresti, Alessia; van Esbroeck, Annelot C M; McGuire, Ross; Di Marzo, Vincenzo; Overkleeft, Herman S; van der Stelt, Mario

2014-08-14

sn-1-Diacylglycerol lipase α (DAGL-α) is the main enzyme responsible for the production of the endocannabinoid 2-arachidonoylglycerol in the central nervous system. Glycine sulfonamides have recently been identified by a high throughput screening campaign as a novel class of inhibitors for this enzyme. Here, we report on the first structure-activity relationship study of glycine sulfonamide inhibitors and their brain membrane proteome-wide selectivity on serine hydrolases with activity-based protein profiling (ABPP). We found that (i) DAGL-α tolerates a variety of biaryl substituents, (ii) the sulfonamide is required for inducing a specific orientation of the 2,2-dimethylchroman substituent, and (iii) a carboxylic acid is essential for its activity. ABPP revealed that the sulfonamide glycine inhibitors have at least three off-targets, including α/β-hydrolase domain 6 (ABHD6). Finally, we identified LEI-106 as a potent, dual DAGL-α/ABHD6 inhibitor, which makes this compound a potential lead for the discovery of new molecular therapies for diet-induced obesity and metabolic syndrome.

Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.

PubMed Central

Hong, Y L; Hossler, P A; Calhoun, D H; Meshnick, S R

1995-01-01

Forty-four sulfa drugs were screened against crude preparations of recombinant Pneumocystis carinii dihydropteroate synthetase. The apparent Michaelis-Menten constants (Km) for p-aminobenzoic acid and 7,8-dihydro-6-hydroxymethylpterin pyrophosphate were 0.34 +/- 0.02 and 2.50 +/- 0.71 microM, respectively. Several sulfa drugs, including sulfathiazole, sulfachlorpyridazine, sulfamethoxypyridazine, and sulfathiourea, inhibited dihydropteroate synthetase approximately as well as sulfamethoxazole, as determined by the concentrations which cause 50% inhibition and/or by Ki. For all sulfones and sulfonamides tested, unsubstituted p-amino groups were necessary for activity, and sulfonamides containing an N1-heterocyclic substituent were found to be the most effective inhibitors. Folate biosynthesis in isolated intact P. carinii was approximately equally sensitive to inhibition by sulfamethoxazole, sulfachlorpyridazine, sulfamethoxypyridazine, sulfisoxazole, and sulfathiazole. Two of these drugs, sulfamethoxypyridazine and sulfisoxazole, are known to be less toxic than sulfamethoxazole and should be further evaluated for the treatment of P. carinii pneumonia. PMID:7486915

Synthesis, X-ray diffraction method, spectroscopic characterization (FT-IR, 1H and 13C NMR), antimicrobial activity, Hirshfeld surface analysis and DFT computations of novel sulfonamide derivatives

NASA Astrophysics Data System (ADS)

Demircioğlu, Zeynep; Özdemir, Fethi Ahmet; Dayan, Osman; Şerbetçi, Zafer; Özdemir, Namık

2018-06-01

Synthesized compounds of N-(2-aminophenyl)benzenesulfonamide 1 and (Z)-N-(2-((2-nitrobenzylidene)amino)phenyl)benzenesulfonamide 2 were characterized by antimicrobial activity, FT-IR, 1H and 13C NMR. Two new Schiff base ligands containing aromatic sulfonamide fragment of (Z)-N-(2-((3-nitrobenzylidene)amino)phenyl)benzenesulfonamide 3 and (Z)-N-(2-((4-nitrobenzylidene)amino)phenyl)benzenesulfonamide 4 were synthesized and investigated by spectroscopic techniques including 1H and 13C NMR, FT-IR, single crystal X-ray diffraction, Hirshfeld surface, theoretical method analyses and by antimicrobial activity. The molecular geometry obtained from the X-ray structure determination was optimized Density Functional Theory (DFT/B3LYP) method with the 6-311++G(d,p) basis set in ground state. From the optimized geometry of the molecules of 3 and 4, the geometric parameters, vibrational wavenumbers and chemical shifts were computed. The optimized geometry results, which were well represented the X-ray data, were shown that the chosen of DFT/B3LYP 6-311G++(d,p) was a successful choice. After a successful optimization, frontier molecular orbitals, chemical activity, non-linear optical properties (NLO), molecular electrostatic mep (MEP), Mulliken population method, natural population analysis (NPA) and natural bond orbital analysis (NBO), which cannot be obtained experimentally, were calculated and investigated.

Synthesis and biological evaluation of substituted N-[3-(1H-pyrrol-1-yl)methyl]-1,2,5,6-tetrahydropyridin-1-yl]benzamide/benzene sulfonamides as anti-inflammatory agents.

PubMed

Gangapuram, Madhavi; Mazzio, Elizabeth; Eyunni, Suresh; Soliman, Karam F A; Redda, Kinfe K

2014-05-01

The pharmacological activities of tetrahydropyridine (THP) derivatives are dependent on the substituent ring moiety. In this study, we investigate the anti-inflammatory activities of 12 newly synthesized substituted N-[3-(1H-pyrrol-1-yl)methyl]-1,2,5,6-tetrahydrobenzamide/benzene sulfonamides (9a-l) in murine BV-2 microglial cells. All compounds were initially screened for attenuation of nitric oxide (NO) production in lipopolysaccharide (LPS) (1 µg/mL)-activated microglial cells. The data show that only SO2 -substituted THPs were effective at sub-lethal concentrations (IC50 values of 12.92 µM (9i), 14.64 µM (9j), 19.63 µM (9k)) relative to L-N6-(1-iminoethyl)lysine positive control (IC50  = 3.1 µM). The most potent SO2 -substituted compound (9i) also blocked the LPS-inducible nitric oxide synthase (iNOS) and attenuated the release of several cytokines including IL-1α, IL-10, and IL-6. These findings establish the moderate immuno-modulating effects of SO2 -substituted THP derivatives. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Antioxidant activities of different solvent extracts of Piper retrofractum Vahl. using DPPH assay

NASA Astrophysics Data System (ADS)

Jadid, Nurul; Hidayati, Dewi; Hartanti, Sylviana Rosyda; Arraniry, Byan Arasyi; Rachman, Rizka Yuanita; Wikanta, Wiwi

2017-06-01

Piper retrofractum Vahl., which belongs to the family Piperaceae, is geographically dispersed in tropical region including Indonesia. They are well-known spice possessing high medicinal properties. This study aimed to determine the antioxidant activity of P. retrofractum fruit, extracted with different solvents (methanol, ethyl acetate, n-hexane) using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. This research was carried out using different concentrations of methanol, ethyl acetate, and n-hexane extracts, (0, 5, 15, 30, 45, 60 ppm). Ascorbic acid was also used as positive antioxidant control. The percentage of inhibition and IC50 were measured. The results showed that the DPPH free radicals were scavenged by all plant extracts in a concentration dependent manner. Moreover, the IC50 values for DPPH radicals with methanol, ethyl acetate and n-hexane extract of the P. retrofractum Vahl. were found to be 101.74; 66.12 and 57.66 ppm, respectively. Interestingly, the IC50 value of n-hexane extract (57.66 ppm) was lower than ascorbic acid (66.12 ppm), indicating that n-hexane extract was a more potent scavenger of free radicals than methanol and ethyl acetate extracts. Taken together, our results suggested that n-hexane extract of P. Retrofractum Vahl. might contain potential antioxidant compounds.

21 CFR 862.3850 - Sulfonamide test system.

Code of Federal Regulations, 2010 CFR

2010-04-01

...) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Toxicology Test Systems § 862... monitoring sulfonamide levels to ensure appropriate therapy. (b) Classification. Class I. [52 FR 16122, May 1...

N-(1-Allyl-3-chloro-4-eth-oxy-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2014-06-01

In the title compound, C19H20ClN3O3S, the benzene ring is inclined to the indazole ring system by 51.23 (8)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers which stack in columns parallel to [011]. The atoms in the allyl group are disordered over two sets of sites with an occupancy ratio of 0.624 (8):0.376 (8).

N-(2-Allyl-4-eth-oxy-2H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Viale, Maurizio; Saadi, Mohamed; El Ammari, Lahcen

2014-05-01

The indazole ring system of the title compound, C19H21N3O3S, is almost planar (r.m.s. deviation = 0.0192 Å) and forms dihedral angles of 77.99 (15) and 83.9 (3)° with the benzene ring and allyl group, respectively. In the crystal, centrosymmetrically related mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into dimers, which are further linked by C-H⋯O hydrogen bonds, forming columns parallel to the b axis.

Impact of manure-related DOM on sulfonamide transport in arable soils

NASA Astrophysics Data System (ADS)

Zhou, Dan; Thiele-Bruhn, Sören; Arenz-Leufen, Martina Gesine; Jacques, Diederik; Lichtner, Peter; Engelhardt, Irina

2016-09-01

Field application of livestock manure introduces colloids and veterinary antibiotics, e.g. sulfonamides (SAs), into farmland. The presence of manure colloids may potentially intensify the SAs-pollution to soils and groundwater by colloid-facilitated transport. Transport of three SAs, sulfadiazine (SDZ), sulfamethoxypyridazine (SMPD), and sulfamoxole (SMOX), was investigated in saturated soil columns with and without manure colloids from sows and farrows, weaners, and fattening pigs. Experimental results showed that colloid-facilitated transport of SMOX was significant in the presence of manure colloids from fattening pigs with low C/N ratio, high SUVA280 nm and protein C, while manure colloids from sows and farrows and weaners had little effect on SMOX transport. In contrast, only retardation was observed for SDZ and SMPD when manure colloids were present. Breakthrough curves (BTCs) of colloids and SAs were replicated well by a newly developed numerical model that considers colloid-filtration theory, competitive kinetic sorption, and co-transport processes. Model results demonstrate that mobile colloids act as carriers for SMOX, while immobile colloids block SMOX from sorbing onto the soil. The low affinity of SMOX to sorb on immobile colloids prevents aggregation and also promotes SMOX's colloid-facilitated transport. Conversely, the high affinity of SDZ and SMPD to sorb on all types of immobile colloids retarded their transport. Thus, manure properties play a fundamental role in increasing the leaching risk of hydrophobic sulfonamides.

Site-Specific Attachment of gold Nanoparticles to DNA Templates

DTIC Science & Technology

2001-01-01

1 -ethyl- 3 -( 3 - dimethylaminopropyl ) carbodiimide hydrochloride (Pierce) and -2.0rmg N...functionalized gold nanoparticles. The gold particles were covalently bound to the amino groups on the DNA using standard 1 -ethyl- 3 - ( 3 - dimethylaminopropyl ...nm). The reaction between the amino group on the DNA and the carboxyl group on the gold particle was facilitated by 1 -ethyl- 3 -( 3 - dimethylaminopropyl

Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties.

PubMed

Scozzafava, Andrea; Menabuoni, Luca; Mincione, Francesco; Supuran, Claudiu T

2002-03-28

Reaction of polyamino-polycarboxylic acids or their dianhydrides with aromatic/heterocyclic sulfonamides possessing a free amino/imino/hydrazino/hydroxy group afforded mono- and bis-sulfonamides containing polyamino-polycarboxylic acid moieties in their molecule. The acids/anhydrides used in synthesis included IDA, NTA, EDDA, EDTA and EDTA dianhydride, DTPA and DTPA dianhydride, EGTA and EGTA dianhydride, and EDDHA, among others. All the newly prepared derivatives showed strong affinity toward isozymes I, II, and IV of carbonic anhydrase (CA). Metal complexes of the new compounds have also been prepared. Metal ions used in such preparations included di- and trivalent main-group and transition cations, such as Zn(II), Cu(II), Al(III), etc. Some of the new sulfonamides/disulfonamides obtained in this way, as well as their metal complexes, behaved as nanomolar CA inhibitors against isozymes II and IV, being slightly less effective in inhibiting isozyme I. Some of these sulfonamides as well as their metal complexes strongly lowered intraocular pressure (IOP) when applied topically, directly into the normotensive/glaucomatous rabbit eye, as 1-2% water solutions/suspensions. The good water solubility of these sulfonamide CA inhibitors, correlated with the neutral pH of their water solutions used in the ophthalmologic applications and the long duration of action of the IOP-lowering effect, makes them interesting candidates for developing novel types of antiglaucoma drugs devoid of serious topical side effects.

Occurrence of select perfluoroalkyl substances at U.S. Air Force aqueous film-forming foam release sites other than fire-training areas: Field-validation of critical fate and transport properties.

PubMed

Anderson, R Hunter; Long, G Cornell; Porter, Ronald C; Anderson, Janet K

2016-05-01

The use of aqueous film-forming foam (AFFF) to extinguish hydrocarbon-based fires is recognized as a significant source of environmental poly- and perfluoroalkyl substances (PFASs). Although the occurrence of select PFASs in soil and groundwater at former fire-training areas (FTAs) at military installations operable since 1970 has been consistently confirmed, studies reporting the occurrence of PFASs at other AFFF-impacted sites (e.g. emergency response locations, AFFF lagoons, hangar-related AFFF storage tanks and pipelines, and fire station testing and maintenance areas) are largely missing from the literature. Further, studies have mostly focused on a single site (i.e., FTAs at military installations) and, thus, lack a comparison of sites with diverse AFFF release history. Therefore, the purpose of this investigation was to evaluate select PFAS occurrence at non-FTA sites on active U.S. Air Force installations with historic AFFF use of varying magnitude. Concentrations of fifteen perfluoroalkyl acids (PFAAs) and perfluorooctane sulfonamide (PFOSA), an important PFOS precursor, were measured from several hundred samples among multiple media (i.e., surface soil, subsurface soil, sediment, surface water, and groundwater) collected from forty AFFF-impacted sites across ten installations between March and September 2014, representing one of the most comprehensive datasets on environmental PFAS occurrence to date. Differences in detection frequencies and observed concentrations due to AFFF release volume are presented along with rigorous data analyses that quantitatively demonstrate phase-dependent (i.e., solid-phase vs aqueous-phase) differences in the chemical signature as a function of carbon chain-length and in situ PFOS (and to a slightly lesser extent PFHxS) formation, presumably due to precursor biotransformation. Published by Elsevier Ltd.

Catalyst-free ethyl biodiesel production from rice bran under subcritical condition

NASA Astrophysics Data System (ADS)

Zullaikah, Siti; Afifudin, Riza; Amalia, Rizky

2015-12-01

In-situ ethyl biodiesel production from rice bran under subcritical water and ethanol with no catalyst was employed. This process is environmentally friendly and is very flexible in term of feedstock utilization since it can handle relatively high moisture and free fatty acids (FFAs) contents. In addition, the alcohol, i.e. bioethanol, is a non-toxic, biodegradable, and green raw material when produced from non-edible biomass residues, leading to a 100% renewable biodiesel. The fatty acid ethyl esters (FAEEs, ethyl biodiesel) are better than fatty acid methyl esters (FAMEs, methyl biodiesel) in terms of fuel properties, including cetane number, oxidation stability and cold flow properties. The influences of the operating variables such as reaction time (1 - 10 h), ethanol concentration (12.5 - 87.5%), and pressurizing gas (N2 and CO2) on the ethyl biodiesel yield and purity have been investigated systematically while the temperature and pressure were kept constant at 200 °C and 40 bar. The optimum results were obtained at 5 h reaction time and 75% ethanol concentration using CO2 as compressing gas. Ethyl biodiesel yield and purity of 58.78% and 61.35%, respectively, were obtained using rice bran with initial FFAs content of 37.64%. FFAs level was reduced to 14.22% with crude ethyl biodiesel recovery of 95.98%. Increasing the reaction time up to 10 h only increased the yield and purity by only about 3%. Under N2 atmosphere and at the same operating conditions (5h and 75% ethanol), ethyl biodiesel yield and purity decreased to 54.63% and 58.07%, respectively, while FFAs level was increased to 17.93% and crude ethyl biodiesel recovery decreased to 87.32%.

[Analysis of sulfonamids and their metabolites in drinking water by high Performance liquid chromatography tandem mass spectrometry].

PubMed

Wang, Shuo; Li, Shuming; Zhang, Xiangming; Wei, Yunfang; Zhang, Meiyun; Zhang, Jing

2015-07-01

To develop a comprehensive method for simultaneous analysis of sulfonamides and their metabolites in drinking water by high performance liquid chromatography tandem mass spectrometry (LC-MS/MS). Different solid-phase extraction columns were compared with respect to the recovery of target drugs from drinking water. The drinking water samples were adjusted to 3 by HCl and purified by a mix mode cation-ion exchange solid-phase extraction (SPE), following determination using LG-MS/MS. A total of 21 sulfonamides were separated by a C15 column (2.1 mm x 100 mm, 1.7 µm) and analyzed under positive ion mode with multi-reaction monitoring. The matrix-matched external standard calibration was used for quantification. The method quantification limits for 21 analytes were 0.03-0.63 ng/L with overall recoveries of 50.1%-114.9%, and the relative standard deviations less than 20%. The method was finally used to analyze sulfonamides in drinking water in Beijing, and 5 target compounds (sulfadiazine, sulfathiazole, sulfapyridine, trimethoprim and sulfamethazine) were detected at a concentration range of 0.08-32.54 ng/L. This method could be applied in simultaneous analysis of sulfonamides and their metabolites in drinking water samples.

Fluorescent Metal-Organic Framework (MOF) as a Highly Sensitive and Quickly Responsive Chemical Sensor for the Detection of Antibiotics in Simulated Wastewater.

PubMed

Zhu, Xian-Dong; Zhang, Kun; Wang, Yu; Long, Wei-Wei; Sa, Rong-Jian; Liu, Tian-Fu; Lü, Jian

2018-02-05

A Zn(II)-based fluorescent metal-organic framework (MOF) was synthesized and applied as a highly sensitive and quickly responsive chemical sensor for antibiotic detection in simulated wastewater. The fluorescent chemical sensor, denoted FCS-1, exhibited enhanced fluorescence derived from its highly ordered, 3D MOF structure as well as excellent water stability in the practical pH range of simulated antibiotic wastewater (pH = 3.0-9.0). Remarkably, FCS-1 was able to effectively detect a series of sulfonamide antibiotics via photoinduced electron transfer that caused detectable fluorescence quenching, with fairly low detection limits. Two influences impacting measurements related to wastewater treatment and water quality monitoring, the presence of heavy-metal ions and the pH of solutions, were studied in terms of fluorescence quenching, which was nearly unaffected in sulfonamide-antibiotic detection. Additionally, the effective detection of sulfonamide antibiotics was rationalized by the theoretical computation of the energy bands of sulfonamide antibiotics, which revealed a good match between the energy bands of FCS-1 and sulfonamide antibiotics, in connection with fluorescence quenching in this system.

European Proficiency testing of national reference laboratories for the confirmation of sulfonamide residues in muscle and milk.

PubMed

Juhel-Gaugain, Murielle; Fourmond, Marie-Pierre; Delepine, Bernard; Laurentie, Michel; Brigitte, Roudaut; Sanders, Pascal

2005-03-01

Two interlaboratory studies were organized in 2002-2003 in order to check the proficiency of laboratories in confirming the presence of sulfonamide residues in muscle and milk. These studies involved 25 EU National Reference Laboratories (NRLs) from 21 different European Countries in charge of statutory monitoring of antimicrobial residues in food of animal origin at a national level. The study was conducted according to international and national guidelines by the Community Reference Laboratory (CRL) in charge of antimicrobial substances. Four different test matrices of sheep muscle and four different test matrices of bovine milk containing different sulfonamide substances were prepared and sent to the participants. Each participant was asked to use his own routine confirmatory method and to analyse each sample in triplicate within a period of about six weeks during which the stability of the materials was checked by the organizer. The sulfonamide content of each material was determined by calculating the robust means of all the results and the deviation of the results from the assigned values was assessed by calculating Z-scores. Overall, results were satisfactory, particularly considering that it was the first proficiency test dealing with sulfonamides organised by the Community Reference Laboratory.

A validated ultra high-pressure liquid chromatography method for separation of candesartan cilexetil impurities and its degradents in drug product

PubMed Central

Kumar, Namala Durga Atchuta; Babu, K. Sudhakar; Gosada, Ullas; Sharma, Nitish

2012-01-01

Introduction: A selective, specific, and sensitive “Ultra High-Pressure Liquid Chromatography” (UPLC) method was developed for determination of candesartan cilexetil impurities as well asits degradent in tablet formulation. Materials and Methods: The chromatographic separation was performed on Waters Acquity UPLC system and BEH Shield RP18 column using gradient elution of mobile phase A and B. 0.01 M phosphate buffer adjusted pH 3.0 with Orthophosphoric acid was used as mobile phase A and 95% acetonitrile with 5% Milli Q Water was used as mobile phase B. Ultraviolet (UV) detection was performed at 254 nm and 210 nm, where (CDS-6), (CDS-5), (CDS-7), (Ethyl Candesartan), (Desethyl CCX), (N-Ethyl), (CCX-1), (1 N Ethyl Oxo CCX), (2 N Ethyl Oxo CCX), (2 N Ethyl) and any unknown impurity were monitored at 254 nm wavelength, and two process-related impurities, trityl alcohol and MTE impurity, were estimated at 210 nm. Candesartan cilexetil andimpurities were chromatographed with a total run time of 20 min. Results: Calibration showed that the response of impurity was a linear function of concentration over the range limit of quantification to 2 μg/mL (r2≥0.999) and the method was validated over this range for precision, intermediate precision, accuracy, linearity, and specificity. For the precision study, percentage relative standard deviation of each impurity was <15% (n=6). Conclusion: The method was found to be precise, accurate, linear, and specific. The proposed method was successfully employed for estimation of candesartan cilexetil impurities in pharmaceutical preparations. PMID:23781475

Emissions of perfluorinated alkylated substances (PFAS) from point sources--identification of relevant branches.

PubMed

Clara, M; Scheffknecht, C; Scharf, S; Weiss, S; Gans, O

2008-01-01

Effluents of wastewater treatment plants are relevant point sources for the emission of hazardous xenobiotic substances to the aquatic environment. One group of substances, which recently entered scientific and political discussions, is the group of the perfluorinated alkylated substances (PFAS). The most studied compounds from this group are perfluorooctanoic acid (PFOA) and perfluorooctane sulphonate (PFOS), which are the most important degradation products of PFAS. These two substances are known to be persistent, bioaccumulative and toxic (PBT). In the present study, eleven PFAS were investigated in effluents of municipal wastewater treatment plants (WWTP) and in industrial wastewaters. PFOS and PFOA proved to be the dominant compounds in all sampled wastewaters. Concentrations of up to 340 ng/L of PFOS and up to 220 ng/L of PFOA were observed. Besides these two compounds, perfluorohexanoic acid (PFHxA) was also present in nearly all effluents and maximum concentrations of up to 280 ng/L were measured. Only N-ethylperfluorooctane sulphonamide (N-EtPFOSA) and its degradation/metabolisation product perfluorooctane sulphonamide (PFOSA) were either detected below the limit of quantification or were not even detected at all. Beside the effluents of the municipal WWTPs, nine industrial wastewaters from six different industrial branches were also investigated. Significantly, the highest emissions or PFOS were observed from metal industry whereas paper industry showed the highest PFOA emission. Several PFAS, especially perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA), perfluorododecanoic acid (PFDoA) and PFOS are predominantly emitted from industrial sources, with concentrations being a factor of 10 higher than those observed in the municipal WWTP effluents. Perfluorodecane sulphonate (PFDS), N-Et-PFOSA and PFOSA were not detected in any of the sampled industrial point sources. (c) IWA Publishing 2008.

21 CFR 520.2240b - Sulfaethoxypyridazine tablets.

Code of Federal Regulations, 2010 CFR

2010-04-01

...; do not treat within 16 days of slaughter; as sole source of sulfonamide; milk that has been taken... sole source of sulfonamide; not for use in lactating dairy cows; Federal law restricts this drug to use...

N-(3-Chloro-1-methyl-1H-indazol-5-yl)-4-methylbenzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Amiri, Ouafa; Saadi, Mohamed; El Ammari, Lahcen

2014-02-01

The asymmetric unit of the title compound, C15H14ClN3O2S, contains two independent mol-ecules showing different conformations: in one mol-ecule, the indazole ring system makes a dihedral angle of 51.5 (1)° with the benzene ring whereas in the other, the indazole unit is almost perpendicular to the benzene ring [dihedral angle 77.7 (1)°]. In the crystal, the mol-ecules are linked by N-H⋯N and N-H⋯O hydrogen bonds, forming a set of four mol-ecules linked in pairs about an inversion centre.

ELISA for sulfonamides and its application for screening in water contamination.

PubMed

Shelver, Weilin L; Shappell, Nancy W; Franek, Milan; Rubio, Fernando R

2008-08-13

Two enzyme-linked immunosorbent assays (ELISAs) were tested for their suitability for detecting sulfonamides in wastewater from various stages in wastewater treatment plants (WWTPs), the river into which the wastewater is discharged, and two swine-rearing facilities. The sulfamethoxazole ELISA cross-reacts with several compounds, achieving detection limits of <0.04 microg/L for sulfamethoxazole (SMX), sulfamethoxypyridine, sulfachloropyridine, and sulfamethoxine, whereas the sulfamethazine (SMZ) ELISA is more compound specific, with a detection limit of <0.03 microg/L. Samples from various stages of wastewater purifications gave 0.6-3.1 microg/L by SMX-ELISA, whereas river samples were approximately 10-fold lower, ranging from below detection to 0.09 microg/L. Swine wastewater samples analyzed by the SMX-ELISA were either at or near detectable limits from one facility, whereas the other facility had concentrations of approximately 0.5 microg/L, although LC-MS/MS did not confirm the presence of SMX. Sulfamethazine ELISA detected no SMZ in either WWTP or river samples. In contrast, wastewater samples from swine facilities analyzed by SMZ-ELISA were found to contain approximately 30 microg/L [piglet (50-100 lb) wastewater] and approximately 7 microg/L (market-weight hog wastewater). Sulfamethazine ELISA analyses of wastewater from another swine facility found concentrations to be near or below detection limits. A solid phase extraction method was used to isolate and concentrate sulfonamides from water samples prior to LC-MS/MS multiresidue confirmatory analysis. The recoveries at 1 microg/L fortification ranged from 42 +/- 4% for SMZ to 88 +/- 4% for SMX ( n = 6). The ELISA results in the WWTPs were confirmed by LC-MS/MS, as sulfonamide multiresidue confirmatory analysis identified SMX, sulfapyridine, and sulfasalazine to be present in the wastewater. Sulfamethazine presence at one swine-rearing facility was also confirmed by LC-MS/MS, demonstrating the usefulness of the ELISA technique as a rapid and high-throughput screening method.

In vitro antioxidant activity and inhibitory effect, on oleic acid-induced hepatic steatosis, of fractions and subfractions from oat (Avena sativa L.) ethanol extract

USDA-ARS?s Scientific Manuscript database

Oats (Avena sativa L.) were extracted with 80% aqueous ethanol and the extract was successively isolated by liquid-liquid partition to yield n-hexane, ethyl acetate, n-butanol and water layers. Among these extractions the ethyl acetate (EA) layer exhibited the highest total phenolic content (TPC), t...

Sequence distribution of acetaldehyde-derived N2-ethyl-dG adducts along duplex DNA.

PubMed

Matter, Brock; Guza, Rebecca; Zhao, Jianwei; Li, Zhong-ze; Jones, Roger; Tretyakova, Natalia

2007-10-01

Acetaldehyde (AA) is the major metabolite of ethanol and may be responsible for an increased gastrointestinal cancer risk associated with alcohol beverage consumption. Furthermore, AA is one of the most abundant carcinogens in tobacco smoke and induces tumors of the respiratory tract in laboratory animals. AA binding to DNA induces Schiff base adducts at the exocyclic amino group of dG, N2-ethylidene-dG, which are reversible on the nucleoside level but can be stabilized by reduction to N2-ethyl-dG. Mutagenesis studies in the HPRT reporter gene and in the p53 tumor suppressor gene have revealed the ability of AA to induce G-->A transitions and A-->T transversions, as well as frameshift and splice mutations. AA-induced point mutations are most prominent at 5'-AGG-3' trinucleotides, possibly a result of sequence specific adduct formation, mispairing, and/or repair. However, DNA sequence preferences for the formation of acetaldehyde adducts have not been previously examined. In the present work, we employed a stable isotope labeling-HPLC-ESI+-MS/MS approach developed in our laboratory to analyze the distribution of acetaldehyde-derived N2-ethyl-dG adducts along double-stranded oligodeoxynucleotides representing two prominent lung cancer mutational "hotspots" and their surrounding DNA sequences. 1,7,NH 2-(15)N-2-(13)C-dG was placed at defined positions within DNA duplexes derived from the K-ras protooncogene and the p53 tumor suppressor gene, followed by AA treatment and NaBH 3CN reduction to convert N2-ethylidene-dG to N2-ethyl-dG. Capillary HPLC-ESI+-MS/MS was used to quantify N2-ethyl-dG adducts originating from the isotopically labeled and unlabeled guanine nucleobases and to map adduct formation along DNA duplexes. We found that the formation of N2-ethyl-dG adducts was only weakly affected by the local sequence context and was slightly increased in the presence of 5-methylcytosine within CG dinucleotides. These results are in contrast with sequence-selective formation of other tobacco carcinogen-DNA adducts along K-ras- and p53-derived duplexes and the preferential modification of endogenously methylated CG dinucleotides by benzo[a]pyrene diol epoxide and acrolein.

Evaluation of novel trans-sulfonamide platinum complexes against tumor cell lines.

PubMed

Pérez, Carlos; Díaz-García, C Vanesa; Agudo-López, Alba; del Solar, Virginia; Cabrera, Silvia; Agulló-Ortuño, M Teresa; Navarro-Ranninger, Carmen; Alemán, José; López-Martín, José A

2014-04-09

Platinum-based drugs, mainly cisplatin, are employed for the treatment of solid malignancies. However, cisplatin treatment often results in the development of chemoresistance, leading to therapeutic failure. Here, the antitumor activity of different trans-sulfonamide platinum complexes in a panel of human cell lines is presented. The cytotoxicity profiles and cell cycle analyses of these platinum sulfonamide complexes were different from those of cisplatin. These studies showed that complex 2b with cyclohexyldiamine and dansyl moieties had the best antitumoral activities. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

Fast and sensitive determination of per- and polyfluoroalkyl substances in seawater.

PubMed

Concha-Graña, Estefanía; Fernández-Martínez, Gerardo; López-Mahía, Purificación; Prada-Rodríguez, Darío; Muniategui-Lorenzo, Soledad

2018-06-22

In this work, a novel, fast, and sensitive method was developed for perfluorooctanoic acid (PFOA), perfluorooctane sulfonic acid (PFOS) and PFOS precursor's determination in seawater. The proposed method consists in a vortex-assisted liquid-liquid microextraction (VALLME) combined with liquid chromatography (LC) and LTQ-Orbitrap high resolution mass spectrometry (LTQ-Orbitrap HRMS) determination. Several parameters affecting both the HPLC-LTQ Orbitrap HRMS determination and the VALLME were studied, with special attention to blank contamination problem. The use of LTQ-Orbitrap-HRMS in full mode, quantifying the target analytes using the exact mass, provides a very powerful detection in terms of sensitivity and specificity maintaining all the information provided by the full mass spectra, allowing, also, the identification of non-target substances. The use of matrix-matched calibration, together with labelled surrogate standards, minimize matrix effects and compensate potential recovery losses, resulting in recoveries between 95 and 105%, with excellent sensitivity (quantitation limit between 0.7 and 6 ng L -1 ) and precision (4-10%). The proposed method requires only 35 mL of sample and 100 μL of extracting solvent, is fast and avoids the use of other solvents to obtain the dispersive cloudy solution, simplifying the procedure and improving the existing procedures for the determination of per- and polyfluoroalkyl substances (PFASs) in seawater in terms of green analytical chemistry. The method was successfully validated by participating in a proficiency test assay provided by the National Measurement Institute of the Australian Government for the determination of PFOA, total PFOS and linear PFOS in waters. A revision of the state of the art in the last twelve years of methods for the analysis of PFASs in seawater and other types of water was performed, and a critical comparison between the developed method and the previously published was included. Finally, the method was applied to the analysis of samples from Ría de Vigo, a sensitive and semiconfined coastal area located in the northwest of Spain. PFOS, N-methyl perfluorooctanesulfonamide (n-MeFOSA) and N-ethyl perfluorooctanesulfonamide (n-EtFOSA) were detected in samples at levels lower than the maximum allowable concentration (MAC) established by Directive 2013/39/EU, but above the annual average (AA) levels. Copyright © 2018 Elsevier B.V. All rights reserved.

Effects of solvent composition in the normal-phase liquid chromatography of alkylphenols and naphthols

DOE Office of Scientific and Technical Information (OSTI.GOV)

Hurtubise, R.J.; Hussain, A.; Silver, H.F.

1981-11-01

The normal-phase liquid chromatographic models of Scott, Snyder, and Soczewinski were considered for a ..mu..-Bondapak NH/sub 2/ stationary phase. n-Heptane:2-propanol and n-heptane:ethyl acetate mobile phases of different compositions were used. Linear relationships were obtained from graphs of log K' vs. log mole fraction of the strong solvent for both n-heptane:2-propanol and n-heptane:ethyl acetate mobile phases. A linear relationship was obtained between the reciprocal of corrected retention volume and % wt/v of 2-propanol but not between the reciprocal of corrected retention volume and % wt/v of ethyl acetate. The slopes and intercept terms from the Snyder and Soczewinski models were foundmore » to approximately describe interactions with ..mu..-Bondapak NH/sub 2/. Capacity factors can be predicted for the compounds by using the equations obtained from mobile phase composition variation experiments.« less

Sulfonamide antibiotic removal and nitrogen recovery from synthetic urine by the combination of rotating advanced oxidation contactor and methylene urea synthesis process.

PubMed

Fukahori, S; Fujiwara, T; Ito, R; Funamizu, N

2015-01-01

The combination of nitrogen recovery and pharmaceutical removal processes for livestock urine treatment were investigated to suppress the discharge of pollutants and recover nitrogen as resources. We combined methylene urea synthesis from urea and adsorption and photocatalytic decomposition of sulfonamide antibiotic using rotating advanced oxidation contactor (RAOC) contained for obtaining both safe fertilizer and reclaimed water. The methylene urea synthesis could recover urea in synthetic urine, however, almost all sulfonamide antibiotic was also incorporated, which is unfavorable from a safety aspect if the methylene urea is to be used as fertilizer. Conversely, RAOC could remove sulfonamide antibiotic without consuming urea. It was also confirmed that the methylene urea could be synthesized from synthetic urine treated by RAOC. Thus, we concluded that RAOC should be inserted prior to the nitrogen recovery process for effective treatment of urine and safe use of methylene urea as fertilizer.

Effects of the presence of sulfonamides in the environment and their influence on human health.

PubMed

Baran, Wojciech; Adamek, Ewa; Ziemiańska, Justyna; Sobczak, Andrzej

2011-11-30

World production and consumption of pharmaceuticals has been steadily increasing. Anti-infectives have been particularly important in modern therapy of microbial infection. Sulfonamides have been widely used for a long time as anti-infectives and are still widely prescribed today. This review presents the most common types of sulfonamides used in healthcare and veterinary medicine and discusses the problems connected with their presence in the biosphere. Based on the analysis of over 160 papers, it was found that small amounts of sulfonamides present in the environment were mainly derived from agricultural activities. These drugs have caused changes in the population of microbes that could be potentially hazardous to human health. This human health hazard could have a global range, and administrative activities have been ineffective in risk reduction. Copyright © 2011 Elsevier B.V. All rights reserved.

Automated Fmoc-based solid-phase synthesis of peptide thioesters with self-purification effect and application in the construction of immobilized SH3 domains.

PubMed

Mende, Franziska; Beisswenger, Michael; Seitz, Oliver

2010-08-18

Peptide thioesters are important building blocks in the total synthesis of proteins and protein domains via fragment ligation. However, synthetic access of peptide thioesters still is a bottleneck of this powerful ligation chemistry. The commonly used methods for the Fmoc-based synthesis of peptide thioesters involve nonautomated solution steps that have to be performed after the solid-phase assembly of the peptide. Usually, HPLC purification is required. Herein, a method that enables crude peptides to be used in divergent native chemical ligations reactions is described. We present an Fmoc-based solid-phase synthesis of peptide thioesters with self-purification which facilitates access to these important building blocks, since the often cumbersome HPLC purification can be avoided. Fmoc-protected amino acids are coupled on a safety catch sulfonamide resin. The self-purifying effect is achieved through the combination of (a) N-terminal coupling of a cleavable cyclization linker and subsequent backbone-to-side chain cyclization, (b) activation of the sulfonamide linkage by alkylation, (c) thiolysis for the selective detachment of truncation products, and (d) TFA cleavage for the liberation of the desired peptide thioester in unprotected form. We have previously shown a method wherein cyclization was performed after carboxymethylation of the sulfonamide. However, the automation of this method was difficult and side reactions at methionine residues hampered the general applicability. The new design involves peptide synthesis on a modified carboxy-functionalized sulfonamide linker, a substantially milder activation of the sulfonamide bond and the use of monomethoxytrityl as well as 2-phenyl-isopropyl protecting groups. This approach solved the problems with methionine containing peptides and enabled the complete automation of the self-purifying synthesis of peptide thioesters. The study also addressed problems in the synthesis of difficult peptides. Aggregated truncation products can resist extraction and contaminate full-length thioesters obtained after TFA cleavage. It is shown that significant enhancements of the purity were achieved when mild acidic extractions were included in the wash protocols after thiolysis. The potential of the method was demonstrated in the parallel synthesis of 20-40 amino acid long peptide thioesters, which were obtained in excellent purities. The thioesters and cysteinyl peptides were used without purification in the assembly of immobilized SH3 protein domains of SHO1 in yeast. A cysteine scan by native chemical ligation suggested single amino acid to cysteine substitutions that (a) confer useful ligation yields, (b) support correct folding, and (c) sustain the function of the folded protein domain. The chemical synthesis of the SH3-domain of SHO1 succeeded in highest yields when cysteine placements at positions S23, F24, and E36 were avoided. The synthetic SH3 mutants were examined in a binding assay, which indicated that N27C, L30C, and D34C mutations provide functional SH3-domain.

Sulfonamide derivative targeting carbonic anhydrase IX as a nuclear imaging probe for colorectal cancer detection in vivo

PubMed Central

Guan, Siao-Syun; Cheng, Chun-Chia; Ho, Ai-Sheng; Wang, Chia-Chi; Luo, Tsai-Yueh; Liao, Tse-Zung; Chang, Jungshan; Wu, Cheng-Tien; Liu, Shing-Hwa

2015-01-01

Hypoxic microenvironment is a common situation in solid tumors. Carbonic anhydrase IX (CA9) is one of the reliable cellular biomarkers of hypoxia. The role of CA9 in colorectal cancer (CRC) remains to be clarified. CA9 inhibitor such as sulfonamides is known to block CA9 activation and reduce tumor growth consequently. Here, we aimed to investigate the CA9 expression in serum and tumor from different stages of CRC patients and utilize sulfonamide derivative with indium-111 labeling as a probe for CRC nuclear imaging detection in vivo. The serum CA9 was correlated with the tumor CA9 levels in different stages of CRC patients. Hypoxia increased cell viability and CA9 expression in colorectal cancer HCT-15 cells. Sulfonamide derivative 5-(2-aminoethyl)thiophene-2-sulfonamide (ATS) could bind with CA9 in vitro under hypoxia. Moreover, tumor tissues in HCT-15-induced xenograft mice possessed higher hypoxic fluorescence signal as compared with other organs. We also found that the radioisotope signal of indium-111 labeled ATS, which was utilized for CRC detection in HCT-15-induced xenograft mice, was markedly enhanced in tumors as compared with non-ATS control. Taken together, these findings suggest that CA9 is a potential hypoxic CRC biomarker and measurement of serum CA9 can be as a potential tool for diagnosing CA9 expressions in CRC clinical practice. The radioisotope-labeled sulfonamide derivative (ATS) may be useful to apply in CRC patients for nuclear medicine imaging. PMID:26447758

Furfuryl ethyl ether: important aging flavor and a new marker for the storage conditions of beer.

PubMed

Vanderhaegen, Bart; Neven, Hedwig; Daenen, Luk; Verstrepen, Kevin J; Verachtert, Hubert; Derdelinckx, Guy

2004-03-24

Recently, it was reported that furfuryl ethyl ether is an important flavor compound indicative of beer storage and aging conditions. A study of the reaction mechanism indicates that furfuryl ethyl ether is most likely formed by protonation of furfuryl alcohol or furfuryl acetate followed by S(N)2-substitution of the leaving group by the nucleophilic ethanol. For the reaction in beer, a pseudo-first-order reaction kinetics was derived. A close correlation was found between the values predicted by the kinetic model and the actual furfuryl ethyl ether concentration evolution during storage of beer. Furthermore, 10 commercial beers of different types, aged during 4 years in natural conditions, were analyzed, and it was found that the furfuryl ethyl ether flavor threshold was largely exceeded in each type of beer. In these natural aging conditions, lower pH, darker color, and higher alcohol content were factors that enhanced furfuryl ethyl ether formation. On the other hand, sulfite clearly reduced furfuryl ethyl ether formation. All results show that the furfuryl ethyl ether concentration is an excellent time-temperature integrator for beer storage.

Synthesis, Structural and Antioxidant Studies of Some Novel N-Ethyl Phthalimide Esters

PubMed Central

Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun

2015-01-01

A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity. PMID:25742494

Synthesis, structural and antioxidant studies of some novel N-ethyl phthalimide esters.

PubMed

Chidan Kumar, C S; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun

2015-01-01

A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity.

Acid-Base Behavior of Carboxylic Acid Groups Covalently Attached at the Surface of Polyethylene: The Usefulness of Contact Angle in Following the Ionization of Surface Functionality

DTIC Science & Technology

1985-08-01

1 -ethyl- 3 -( 3 - dimethylaminopropyl )car- bodiimide hydrochloride (Sigma) and glycine (2-3H) (New England Nuclear as a 15.0...of N-hydroxysuc- *cinimide and 0.5 g of 1 -ethyl- 3 -( 3 - dimethylaminopropyl )carbodiimide hydrochloride for 12 hours to produce PE-CO-N-hydroxysuccinimide...and/or Dist 1 Special I- S,N 0102- LF. 014.6601 SECURITY CLASSIFICATION Of THIS PAGIrm( en Date Entered) / . ~ * .! - 3 - Introduction. In

Discovery and characterization of a novel series of N-phenylsulfonyl-1H-pyrrole picolinamides as positive allosteric modulators of the metabotropic glutamate receptor 4 (mGlu4).

PubMed

Gogliotti, Rocco D; Blobaum, Anna L; Morrison, Ryan M; Daniels, J Scott; Salovich, James M; Cheung, Yiu-Yin; Rodriguez, Alice L; Loch, Matthew T; Conn, P Jeffrey; Lindsley, Craig W; Niswender, Colleen M; Hopkins, Corey R

2016-07-01

Herein we report the synthesis and characterization of a novel series of N-phenylsulfonyl-1H-pyrrole picolinamides as novel positive allosteric modulators of mGlu4. We detail our work towards finding phenyl replacements for the core scaffold of previously reported phenyl sulfonamides and phenyl sulfone compounds. Our efforts culminated in the identification of N-(1-((3,4-dimethylphenyl)sulfonyl)-1H-pyrrol-3-yl)picolinamide as a potent PAM of mGlu4. Copyright © 2016 Elsevier Ltd. All rights reserved.

Crystal structure of N-(3-chloro-1-methyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Gamouh, Ahmed; Saadi, Mohamed; El Ammari, Lahcen

2014-09-01

In the title compound, C15H14ClN3O3S, the dihedral angle between the planes of the indazole ring system (r.m.s. deviation = 0.007 Å) and the benzene ring is 89.05 (7)°. The meth-oxy C atom deviates from its attached ring by 0.196 (3) Å. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops. The dimers are connected into [010] chains by C-H⋯O inter-actions.

Electrochemosensor for trace analysis of perfluorooctane sulfonate in water based on a molecularly imprinted poly o-phenylenediamine polymer.

PubMed

Karimian, Najmeh; Stortini, Angela Maria; Moretto, Ligia Maria; Costantino, Claudio; Bogialli, Sara; Ugo, Paolo

2018-06-18

This work is aimed at developing an electrochemical sensor for the sensitive and selective detection of trace levels of perfluorooctane sulfonate (PFOS) in water. Contamination of waters by perfluorinated alkyl substances (PFAS) is a problem of global concern due to their suspected toxicity and ability to bioaccumulate. PFOS is the perfluorinated compound of major concern, as it has the lowest suggested control concentrations. The sensor reported here is based on a gold electrode modified with a thin coating of a molecularly imprinted polymer (MIP), prepared by anodic electropolymerization of o-phenylenediamine (o-PD) in the presence of PFOS as the template. Activation of the sensor is achieved by template removal with suitable a solvent mixture. Voltammetry, a quartz crystal microbalance, scanning electron microscopy and elemental analysis were used to monitor the electropolymerization process, template removal and binding of the analyte. Ferrocenecarboxylic acid (FcCOOH) has been exploited as an electrochemical probe able to generate analytically useful voltammetric signals by competing for the binding sites with PFOS, as the latter is not electroactive. The sensor has a low detection limit (0.04 nM), a satisfactory selectivity, and is reproducible and repeatable, giving analytical results in good agreement with those obtained by HPLC-MS/MS analyses.

Discovery of Tertiary Sulfonamides as Potent Liver X Receptor Antagonists

DOE Office of Scientific and Technical Information (OSTI.GOV)

Zuercher, William J.; Buckholz†, Richard G.; Campobasso, Nino

2010-08-12

Tertiary sulfonamides were identified in a HTS as dual liver X receptor (LXR, NR1H2, and NR1H3) ligands, and the binding affinity of the series was increased through iterative analogue synthesis. A ligand-bound cocrystal structure was determined which elucidated key interactions for high binding affinity. Further characterization of the tertiary sulfonamide series led to the identification of high affinity LXR antagonists. GSK2033 (17) is the first potent cell-active LXR antagonist described to date. 17 may be a useful chemical probe to explore the cell biology of this orphan nuclear receptor.

Discovery of tertiary sulfonamides as potent liver X receptor antagonists.

PubMed

Zuercher, William J; Buckholz, Richard G; Campobasso, Nino; Collins, Jon L; Galardi, Cristin M; Gampe, Robert T; Hyatt, Stephen M; Merrihew, Susan L; Moore, John T; Oplinger, Jeffrey A; Reid, Paul R; Spearing, Paul K; Stanley, Thomas B; Stewart, Eugene L; Willson, Timothy M

2010-04-22

Tertiary sulfonamides were identified in a HTS as dual liver X receptor (LXR, NR1H2, and NR1H3) ligands, and the binding affinity of the series was increased through iterative analogue synthesis. A ligand-bound cocrystal structure was determined which elucidated key interactions for high binding affinity. Further characterization of the tertiary sulfonamide series led to the identification of high affinity LXR antagonists. GSK2033 (17) is the first potent cell-active LXR antagonist described to date. 17 may be a useful chemical probe to explore the cell biology of this orphan nuclear receptor.

Preparation and application of epitope magnetic molecularly imprinted polymers for enrichment of sulfonamide antibiotics in water.

PubMed

Hu, Yufeng; Wang, Cheng; Li, Xiangdao; Liu, Lifen

2017-10-01

Sulfonamides, which are widely used synthetic antibiotics, are hydrophilic and stable. They can easily migrate into the environment and aquatic animals, and increase the risk of cancer, drug resistance, and allergic symptoms if consumed by humans. Here, we developed an epitope magnetic imprinting approach to enrich multiple sulfonamide antibiotics from a water sample. Epitope magnetic molecularly imprinted polymers (EMMIPs) were prepared by free-radical polymerization using vinyl-functioned Fe 3 O 4 as a core, sulfanilamide (SA) as a dummy template, methacrylic acid as a functional monomer, and ethylene glycol dimethacrylate as a cross-linker. The performance of the EMMIPs was first evaluated by rebinding SA, and then an adsorption experiment was conducted to assess the extraction of multiple sulfonamide antibiotics containing the SA group. The binding experiments showed that the EMMIPs reached adsorption equilibrium in only 5 min with adsorption of SA at 2040 μg/g, compared with just 462 μg/g for the epitope magnetic non-imprinted polymers. EMMIPs were combined with HPLC for the detection of six sulfonamide antibiotics in surface water samples. The recoveries ranged from 79.3 to 92.4% and the relative standard deviations from 0.9 to 7.3%. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection.

PubMed

Salisbury, Craig D C; Sweet, Jason C; Munro, Roger

2004-01-01

A liquid chromatographic method for the determination of sulfachloropyridazine, sulfadiazine, sulfadimethoxine, sulfadoxine, sulfaethoxypyridazine, sulfamethazine, sulfaquinoxaline, and sulfathiazole residues in the muscle, liver, and kidney of food animals using sulfapyridine as internal standard is reported. Tissues are extracted using a modified version of AOAC Official Method 983.31 (Sulfonamide Residues in Animal Tissues). The sample extract is reconstituted in pH 3.0 buffer-acetonitrile (60 + 40) and filtered into an autosampler vial. Using a programmable autosampler of a liquid chromatograph, a portion of the sample is derivatized precolumn with fluorescamine. The sulfonamide derivatives are separated by liquid chromatography using a C18 column with a mobile phase of 0.02M phosphoric acid-acetonitrile (60.5 + 39.5) and detected by fluorescence (excitation, 405 nm; emission, 495 nm). The method was applied to swine and cattle muscle, liver, and kidney; sheep and horse muscle and kidney; and chicken muscle and liver. The mean values for samples fortified with sulfonamides at levels between 0.05 and 0.2 microg/g agreed within 96-99% of spiked levels, with coefficients of variation ranging from 4-10%. The limit of detection (LOD) for all sulfonamides was 0.01 microg/g, with the exception of sulfaquinoxaline, for which the LOD was 0.015 microg/g.

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)benzene­sulfonamide

PubMed Central

Kumar, Mohan; Mallesha, L.; Sridhar, M. A.; Kapoor, Kamini; Gupta, Vivek K.; Kant, Rajni

2012-01-01

The title compound, C22H23BrN4O3S2, crystallizes with two mol­ecules, A and B, in the asymmetric unit. In one of these, the meth­oxy group is disordered over two sets of sites in a 0.565 (9):0.435 (9) ratio. The benzene rings bridged by the sulfonamide group are tilted relative to each other by 37.4 (1) and 56.1 (1)° in mol­ecules A and B, respectively, while the dihedral angles between the sulfur-bridged pyrimidine and benzene rings are 72.4 (1) and 70.2 (1)° for A and B, respectively. The piperidine ring adopts a chair conformation in both mol­ecules. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds occur for both A and B; the dimers are linked into [010] chains by C—H⋯O hydrogen bonds. The crystal structure also features inversion-generated aromatic π–π stacking inter­actions between the pyrimidine rings for both mol­ecules [centroid–centroid distances = 3.412 (2) (mol­ecule A) and 3.396 (2) Å (mol­ecule B)]. PMID:23284517

Impact of manure-related DOM on sulfonamide transport in arable soils.

PubMed

Zhou, Dan; Thiele-Bruhn, Sören; Arenz-Leufen, Martina Gesine; Jacques, Diederik; Lichtner, Peter; Engelhardt, Irina

2016-09-01

Field application of livestock manure introduces colloids and veterinary antibiotics, e.g. sulfonamides (SAs), into farmland. The presence of manure colloids may potentially intensify the SAs-pollution to soils and groundwater by colloid-facilitated transport. Transport of three SAs, sulfadiazine (SDZ), sulfamethoxypyridazine (SMPD), and sulfamoxole (SMOX), was investigated in saturated soil columns with and without manure colloids from sows and farrows, weaners, and fattening pigs. Experimental results showed that colloid-facilitated transport of SMOX was significant in the presence of manure colloids from fattening pigs with low C/N ratio, high SUVA280nm and protein C, while manure colloids from sows and farrows and weaners had little effect on SMOX transport. In contrast, only retardation was observed for SDZ and SMPD when manure colloids were present. Breakthrough curves (BTCs) of colloids and SAs were replicated well by a newly developed numerical model that considers colloid-filtration theory, competitive kinetic sorption, and co-transport processes. Model results demonstrate that mobile colloids act as carriers for SMOX, while immobile colloids block SMOX from sorbing onto the soil. The low affinity of SMOX to sorb on immobile colloids prevents aggregation and also promotes SMOX's colloid-facilitated transport. Conversely, the high affinity of SDZ and SMPD to sorb on all types of immobile colloids retarded their transport. Thus, manure properties play a fundamental role in increasing the leaching risk of hydrophobic sulfonamides. Copyright © 2016 Elsevier B.V. All rights reserved.

Serum perfluorooctanoic acid and perfluorooctane sulfonate concentrations in relation to birth outcomes in the Mid-Ohio Valley, 2005-2010.

PubMed

Darrow, Lyndsey A; Stein, Cheryl R; Steenland, Kyle

2013-10-01

Previous research suggests perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) may be associated with adverse pregnancy outcomes. We conducted a population-based study of PFOA and PFOS and birth outcomes from 2005 through 2010 in a Mid-Ohio Valley community exposed to high levels of PFOA through drinking-water contamination. Women provided serum for PFOA and PFOS measurement in 2005-2006 and reported reproductive histories in subsequent follow-up interviews. Reported singleton live births among 1,330 women after 1 January 2005 were linked to birth records (n = 1,630) to identify the outcomes of preterm birth (< 37 weeks gestation), pregnancy-induced hypertension, low birth weight (< 2,500 g), and birth weight (grams) among full-term infants. We observed little or no evidence of association between maternal serum PFOA or PFOS and preterm birth (n = 158) or low birth weight (n = 88). Serum PFOA and PFOS were both positively associated with pregnancy-induced hypertension (n = 106), with adjusted odds ratios (ORs) per log unit increase in PFOA and PFOS of 1.27 (95% CI: 1.05, 1.55) and 1.47 (95% CI: 1.06, 2.04), respectively, but associations did not increase monotonically when categorized by quintiles. Results of subanalyses restricted to pregnancies conceived after blood collection were consistent with the main analyses. There was suggestion of a modest negative association between PFOS and birth weight in full-term infants (-29 g per log unit increase; 95% CI: -66, 7), which became stronger when restricted to births conceived after the blood sample collection (-49 g per log unit increase; 95% CI: -90, -8). Results provide some evidence of positive associations between measured serum perfluorinated compounds and pregnancy-induced hypertension and a negative association between PFOS and birth weight among full-term infants.

S-Nitroso-N-acetyl-L-cysteine ethyl ester (SNACET) and N-acetyl-L-cysteine ethyl ester (NACET)-Cysteine-based drug candidates with unique pharmacological profiles for oral use as NO, H2S and GSH suppliers and as antioxidants: Results and overview.

PubMed

Tsikas, Dimitrios; Schwedhelm, Kathrin S; Surdacki, Andrzej; Giustarini, Daniela; Rossi, Ranieri; Kukoc-Modun, Lea; Kedia, George; Ückert, Stefan

2018-02-01

S -Nitrosothiols or thionitrites with the general formula RSNO are formally composed of the nitrosyl cation (NO + ) and a thiolate (RS - ), the base of the corresponding acids RSH. The smallest S -nitrosothiol is HSNO and derives from hydrogen sulfide (HSH, H 2 S). The most common physiological S -nitrosothiols are derived from the amino acid L-cysteine (CysSH). Thus, the simplest S -nitrosothiol is S -nitroso-L-cysteine (CysSNO). CysSNO is a spontaneous potent donor of nitric oxide (NO) which activates soluble guanylyl cyclase to form cyclic guanosine monophosphate (cGMP). This activation is associated with multiple biological actions that include relaxation of smooth muscle cells and inhibition of platelet aggregation. Like NO, CysSNO is a short-lived species and occurs physiologically at concentrations around 1 nM in human blood. CysSNO can be formed from CysSH and higher oxides of NO including nitrous acid (HONO) and its anhydride (N 2 O 3 ). The most characteristic feature of RSNO is the S-transnitrosation reaction by which the NO + group is reversibly transferred to another thiolate. By this way numerous RSNO can be formed such as the low-molecular-mass S -nitroso- N -acetyl-L-cysteine (SNAC) and S -nitroso-glutathione (GSNO), and the high-molecular-mass S -nitrosol-L-cysteine hemoglobin (HbCysSNO) present in erythrocytes and S -nitrosol-L-cysteine albumin (AlbCysSNO) present in plasma at concentrations of the order of 200 nM. All above mentioned RSNO exert NO-related biological activity, but they must be administered intravenously. This important drawback can be overcome by lipophilic charge-free RSNO. Thus, we prepared the ethyl ester of SNAC, the S -nitroso- N -acetyl-L-cysteine ethyl ester (SNACET), from synthetic N -acetyl-L-cysteine ethyl ester (NACET). Both NACET and SNACET have improved pharmacological features over N -acetyl-L-cysteine (NAC) and S -nitroso- N -acetyl-L-cysteine (SNAC), respectively, including higher oral bioavailability. SNACET exerts NO-related activities which can be utilized in the urogenital tract and in the cardiovascular system. NACET, with high oral bioavailability, is a strong antioxidant and abundant precursor of GSH, unlike its free acid N -acetyl-L-cysteine (NAC). Here, we review the chemical and pharmacological properties of SNACET and NACET as well as their analytical chemistry. We also report new results from the ingestion of S -[ 15 N]nitroso- N -acetyl-L-cysteine ethyl ester (S 15 NACET) demonstrating the favorable pharmacological profile of SNACET.

Thermal and biological evolution of Fe(III)-Sulfanilamide complexes synthesized by green strategy

NASA Astrophysics Data System (ADS)

Prajapat, Garima; Rathore, Uma; Gupta, Rama; Bhojak, N.

2018-05-01

Sulfonamides belong to a category of sulfadrugs, that are widely used as antibiotic medicines. Their metal complexes, also called Metallodrugs, are known to have diverse pharmacological applications and are significantly used as therapeutic agents for treatment of several human diseases. Fe(III) complexes of two sulfonamides, namely Sulfanilamide and Sulfadiazine have been synthesized by the method of Microwave Assisted Organic Synthesis (MAOS), using acetone as solvent medium. Presence of excellent donor atoms such as N and O, induce these drugs to exhibit a chelating behavior with the metal ion, and to act as bidentate ligands. Both the complexes were found to have four coordinated, tetrahedral geometry with one molecule of water of crystallisation. Thermal decomposition studies were carried out in an inert nitrogen atmosphere by Thermogravimetric (TGA) and Derivative Thermogravimetric (DTA) analysis. Interpretation of thermograms have been done to evaluate various kinetic and thermodynamic parameters, using integral method of Coats and Redfern. The antibacterial activity for both complexes have been screened against E.coli, S. aureus and B. subtilis.

Discovery of 8-Membered Ring Sulfonamides as Inhibitors of Oncogenic Mutant Isocitrate Dehydrogenase 1.

PubMed

Law, Jason M; Stark, Sebastian C; Liu, Ke; Liang, Norah E; Hussain, Mahmud M; Leiendecker, Matthias; Ito, Daisuke; Verho, Oscar; Stern, Andrew M; Johnston, Stephen E; Zhang, Yan-Ling; Dunn, Gavin P; Shamji, Alykhan F; Schreiber, Stuart L

2016-10-13

Evidence suggests that specific mutations of isocitrate dehydrogenases 1 and 2 (IDH1/2) are critical for the initiation and maintenance of certain tumor types and that inhibiting these mutant enzymes with small molecules may be therapeutically beneficial. In order to discover mutant allele-selective IDH1 inhibitors with chemical features distinct from existing probes, we screened a collection of small molecules derived from diversity-oriented synthesis. The assay identified compounds that inhibit the IDH1-R132H mutant allele commonly found in glioma. Here, we report the discovery of a potent (IC 50 = 50 nM) series of IDH1-R132H inhibitors having 8-membered ring sulfonamides as exemplified by the compound BRD2879. The inhibitors suppress ( R )-2-hydroxyglutarate production in cells without apparent toxicity. Although the solubility and pharmacokinetic properties of the specific inhibitor BRD2879 prevent its use in vivo , the scaffold presents a validated starting point for the synthesis of future IDH1-R132H inhibitors having improved pharmacological properties.

C18-coated stir bar sorptive extraction combined with high performance liquid chromatography-electrospray tandem mass spectrometry for the analysis of sulfonamides in milk and milk powder.

PubMed

Yu, Chunhe; Hu, Bin

2012-02-15

A simple, rapid, sensitive, inexpensive and less sample consuming method of C(18)-stir bar sorptive extraction (SBSE)-high performance liquid chromatography (HPLC)-tandem mass spectrometry (MS/MS) was proposed for the determination of six sulfonamides in milk and milk powder samples. C(18) silica particles coated stir bar was prepared by adhesion method, and two kinds of adhesive glue, polydimethylsiloxane (PDMS) sol and epoxy glue were tried. It was found that the C(18)-coated stir bar prepared by PDMS sol as adhesive glue is more robust than that prepared by epoxy glue when liquid desorption was employed, in terms of both lifetime and organic solvent tolerance. The preparation of C(18) stir bar was simple with good mechanic strength and the stir bar could be reused for more than 20 times. Granular coating has relatively high specific surface area and is propitious to sorptive extraction based process. Compared to conventional PDMS SBSE coating, C(18) coating shows good affinity to the target polar/weak polar sulfonamides. To achieve optimum SBSE extraction performance, several parameters including extraction and desorption time, ionic strength, sample pH and stirring speed were investigated. The detection limits of the proposed method for six sulfonamides were in the range of 0.9-10.5 μg/L for milk and 2.7-31.5 μg/kg for milk powder. Good linearities were obtained for sulfonamides with the correlation coefficients (R) above 0.9922. Finally, the proposed method was successfully applied to the determination of sulfonamides in milk and milk powder samples and satisfied recoveries of spiked target compounds in real samples were obtained. Copyright © 2012 Elsevier B.V. All rights reserved.

Modularity and three-dimensional isostructurality of novel synthons in sulfonamide–lactam cocrystals

PubMed Central

Bolla, Geetha; Mittapalli, Sudhir; Nangia, Ashwini

2015-01-01

The design of novel supramolecular synthons for functional groups relevant to drugs is an essential prerequisite for applying crystal engineering in the development of novel pharmaceutical cocrystals. It has been convincingly shown over the past decade that molecular level control and modulation can influence the physicochemical properties of drug cocrystals. Whereas considerable advances have been reported on the design of cocrystals for carboxylic acids and carboxamide functional groups, the sulfonamide group, which is a cornerstone of sulfa drugs, is relatively unexplored for reproducible heterosynthon-directed crystal engineering. The occurrence of synthons and isostructurality in sulfonamide–lactam cocrystals (SO2NH2⋯CONH hydrogen bonding) is analyzed to define a strategy for amide-type GRAS (generally recognized as safe) coformers with sulfonamides. Three types of supramolecular synthons are identified for the N—H donor of sulfonamide hydrogen bonding to the C=O acceptor of amide. Synthon 1: catemer synthon C 2 1(4) chain motif, synthon 2: dimer–cyclic ring synthon R 2 2(8)R 4 2(8) motifs, and synthon 3: dimer–catemer synthon of R 2 2(8)C 1 1(4)D notation. These heterosynthons of the cocrystals observed in this study are compared with the N—H⋯O dimer R 2 2(8) ring and C(4) chain motifs of the individual sulfonamide structures. The X-ray crystal structures of sulfonamide–lactam cocrystals exhibit interesting isostructurality trends with the same synthon being present. One-dimensional, two-dimensional and three-dimensional isostructurality in crystal structures is associated with isosynthons and due to their recurrence, novel heterosynthons for sulfonamide cocrystals are added to the crystal engineer’s toolkit. With the predominance of sulfa drugs in medicine, these new synthons provide rational strategies for the design of binary and potentially ternary cocrystals of sulfonamides. PMID:26175899

Design, Synthesis, and Evaluation of Dihydrobenzo[cd]indole-6-sulfonamide as TNF-α Inhibitors.

PubMed

Deng, Xiaobing; Zhang, Xiaoling; Tang, Bo; Liu, Hongbo; Shen, Qi; Liu, Ying; Lai, Luhua

2018-01-01

Tumor necrosis factor-α (TNF-α) plays a pivotal role in inflammatory response. Dysregulation of TNF can lead to a variety of disastrous pathological effects, including auto-inflammatory diseases. Antibodies that directly targeting TNF-α have been proven effective in suppressing symptoms of these disorders. Compared to protein drugs, small molecule drugs are normally orally available and less expensive. Till now, peptide and small molecule TNF-α inhibitors are still in the early stage of development, and much more efforts should be made. In a previously study, we reported a TNF-α inhibitor, EJMC-1 with modest activity. Here, we optimized this compound by shape screen and rational design. In the first round, we screened commercial compound library for EJMC-1 analogs based on shape similarity. Out of the 68 compounds tested, 20 compounds showed better binding affinity than EJMC-1 in the SPR competitive binding assay. These 20 compounds were tested in cell assay and the most potent compound was 2-oxo-N-phenyl-1,2-dihydrobenzo[ cd ]indole-6-sulfonamide ( S10 ) with an IC 50 of 14 μM, which was 2.2-fold stronger than EJMC-1 . Based on the docking analysis of S10 and EJMC-1 binding with TNF-α, in the second round, we designed S10 analogs, purchased seven of them, and synthesized seven new compounds. The best compound, 4e showed an IC 50 -value of 3 μM in cell assay, which was 14-fold stronger than EJMC-1 . 4e was among the most potent TNF-α organic compound inhibitors reported so far. Our study demonstrated that 2-oxo-N-phenyl-1,2-dihydrobenzo[ cd ]indole-6-sulfonamide analogs could be developed as potent TNF-α inhibitors. 4e can be further optimized for its activity and properties. Our study provides insights into designing small molecule inhibitors directly targeting TNF-α and for protein-protein interaction inhibitor design.

Design, Synthesis, and Evaluation of Dihydrobenzo[cd]indole-6-sulfonamide as TNF-alpha Inhibitors

NASA Astrophysics Data System (ADS)

Deng, Xiaobing; Zhang, Xiaoling; Tang, Bo; Liu, Hongbo; Shen, Qi; Liu, Ying; Lai, Luhua

2018-04-01

Tumor necrosis factor-α (TNF-α) plays a pivotal role in inflammatory response. Dysregulation of TNF can lead to a variety of disastrous pathological effects, including auto-inflammatory diseases. Antibodies that directly targeting TNF-α have been proven effective in suppressing symptoms of these disorders. Compared to protein drugs, small molecule drugs are normally orally available and less expensive. Till now, peptide and small molecule TNF-α inhibitors are still in the early stage of development, and much more efforts should be made. In a previously study, we reported a TNF-α inhibitor, EJMC-1 with modest activity. Here, we optimized this compound by shape screen and rational design. In the first round, we screened commercial compound library for EJMC-1 analogs based on shape similarity. Out of the 68 compounds tested, 20 compounds showed better binding affinity than EJMC-1 in the SPR competitive binding assay. These 20 compounds were tested in cell assay and the most potent compound was 2-oxo-N-phenyl-1,2-dihydrobenzo[cd]indole-6-sulfonamide (S10) with an IC50 of 14 M, which was 2.2-fold stronger than EJMC-1. Based on the docking analysis of S10 and EJMC-1 binding with TNF-α, in the second round, we designed S10 analogues, purchased 7 of them and synthesized 7 new compounds. The best compound, 4e showed an IC50 value of 3 M in cell assay, which was 14-fold stronger than EJMC-1. 4e was among the most potent TNF-α organic compound inhibitors reported so far. Our study demonstrated that 2-oxo-N-phenyl-1,2-dihydrobenzo[cd]indole-6-sulfonamide analogues could be developed as potent TNF-α inhibitors. 4e can be further optimized for its activity and properties. Our study provides insights into designing small molecule inhibitors directly targeting TNF-α and for protein-protein interaction inhibitor design.

Ferrate promoted oxidative cleavage of sulfonamides: Kinetics and product formation under acidic conditions

EPA Science Inventory

Sulfonamide-based antibiotics are often detected in surface waters and secondary wastewater effluents and pose an eminent threat for the development of antibiotic resistance bacteria and genes in aquatic environment. This paper presents the kinetics and stoichiometry of the oxid...

Methylfolate Trap Promotes Bacterial Thymineless Death by Sulfa Drugs

PubMed Central

Pham, Thanh H.; Jakubowski, Hieronim; Wolff, Kerstin A.; Ogwang, Sam; Timpona, Joseph L.; Gogula, Soumya; Jacobs, Michael R.; Ruetz, Markus; Kräutler, Bernhard; Jacobsen, Donald W.; Zhang, Guo-Fang; Nguyen, Liem

2016-01-01

The methylfolate trap, a metabolic blockage associated with anemia, neural tube defects, Alzheimer’s dementia, cardiovascular diseases, and cancer, was discovered in the 1960s, linking the metabolism of folate, vitamin B12, methionine and homocysteine. However, the existence or physiological significance of this phenomenon has been unknown in bacteria, which synthesize folate de novo. Here we identify the methylfolate trap as a novel determinant of the bacterial intrinsic death by sulfonamides, antibiotics that block de novo folate synthesis. Genetic mutagenesis, chemical complementation, and metabolomic profiling revealed trap-mediated metabolic imbalances, which induced thymineless death, a phenomenon in which rapidly growing cells succumb to thymine starvation. Restriction of B12 bioavailability, required for preventing trap formation, using an “antivitamin B12” molecule, sensitized intracellular bacteria to sulfonamides. Since boosting the bactericidal activity of sulfonamides through methylfolate trap induction can be achieved in Gram-negative bacteria and mycobacteria, it represents a novel strategy to render these pathogens more susceptible to existing sulfonamides. PMID:27760199

Removal and factors influencing removal of sulfonamides and trimethoprim from domestic sewage in constructed wetlands.

PubMed

Dan A; Yang, Yang; Dai, Yu-Nv; Chen, Chun-Xing; Wang, Su-Yu; Tao, Ran

2013-10-01

Twelve pilot-scale constructed wetlands with different configurations were set up in the field to evaluate the removal and factors that influence removal of sulfonamides (sulfadiazine, sulfapyridine, sulfacetamide, sulfamethazine and sulfamethoxazole) and trimethoprim from domestic sewage. The treatments included four flow types, three substrates, two plants and three hydraulic loading rates across two seasons (summer and winter). Most target antibiotics were efficiently removed by specific constructed wetlands; in particular, all types of constructed wetlands performed well for the degradation of sulfapyridine. Flow types were the most important influencing factor in this study, and the best removal of sulfonamides was achieved in vertical subsurface-flow constructed wetlands; however, the opposite phenomenon was found with trimethoprim. Significant relationships were observed between antibiotic degradation and higher temperature and redox potential, which indicated that microbiological pathways were the most probable degradation route for sulfonamides and trimethoprim in constructed wetlands. Copyright © 2013 Elsevier Ltd. All rights reserved.

Inhalation by design: novel ultra-long-acting β(2)-adrenoreceptor agonists for inhaled once-daily treatment of asthma and chronic obstructive pulmonary disease that utilize a sulfonamide agonist headgroup.

PubMed

Glossop, Paul A; Lane, Charlotte A L; Price, David A; Bunnage, Mark E; Lewthwaite, Russell A; James, Kim; Brown, Alan D; Yeadon, Michael; Perros-Huguet, Christelle; Trevethick, Michael A; Clarke, Nicholas P; Webster, Robert; Jones, Rhys M; Burrows, Jane L; Feeder, Neil; Taylor, Stefan C J; Spence, Fiona J

2010-09-23

A novel series of potent and selective sulfonamide derived β(2)-adrenoreceptor agonists are described that exhibit potential as inhaled ultra-long-acting bronchodilators for the treatment of asthma and chronic obstructive pulmonary disease. Analogues from this series mediate very long-lasting smooth muscle relaxation in guinea pig tracheal strips. The sulfonamide agonist headgroup confers high levels of intrinsic crystallinity that could relate to the acidic sulfonamide motif supporting a zwitterionic form in the solid state. Optimization of pharmacokinetic properties was achieved through targeted introduction of a phenolic moiety to support rapid phase II clearance, thereby minimizing systemic exposure following inhalation and reducing systemically mediated adverse events. Compound 38 (PF-610355) is identified as a clinical candidate from this series, with in vivo duration of action studies confirming its potential for once-daily use in humans. Compound 38 is currently in advanced phase II clinical studies.

N-(3-Chloro-1H-indazol-5-yl)-4-meth­oxy­benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

In the title compound, C14H12ClN3O3S, the fused five- and six-membered rings are folded slightly along the common edge, forming a dihedral angle of 3.2 (1)°. The mean plane through the indazole system makes a dihedral angle of 30.75 (7)° with the distant benzene ring. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules, forming a two-dimensional network parallel to (001). PMID:24454078

Matrix solid-phase dispersion extraction of sulfonamides from blood.

PubMed

Zhang, Yupu; Xu, Xu; Liu, He; Zhai, Yujuan; Sun, Ye; Sun, Shuo; Zhang, Hanqi; Yu, Aimin; Wang, Yinghua

2012-02-01

Matrix solid-phase dispersion extraction was applied to the extraction of sulfadiazine, sulfamerazine, and sulfamethazine from human and animal bloods. The separation and determination of the analytes were carried out by high-performance liquid chromatography. The effects of the types of the dispersion adsorbents and elution solvents were investigated, and the highest recovery was obtained when diatomaceous earth was used as the dispersion adsorbent, while acetone was used as the elution solvent. Under the optimal conditions, the linear range for determining the sulfonamides in blood samples was 0.020-10.0 µg/mL, and the average recoveries of the three sulfonamides were higher than 87.5%.

The synthesis and structures of 1,1'-bis(sulfonyl)ferrocene derivatives.

PubMed

Chanawanno, Kullapa; Holstrom, Cole; Crandall, Laura A; Dodge, Henry; Nemykin, Victor N; Herrick, Richard S; Ziegler, Christopher J

2016-09-28

A series of 1,1'-bis(sulfonyl)ferrocene compounds were produced via the 1,1'-bis(sulfonate)ferrocene ammonium salt. This compound can be readily converted to 1,1' bis(sulfonylchloride)ferrocene. By varying stoichiometry and reaction times, both mono- and bis-sulfonamide derivatives can be synthesized. All new compounds presented in this report have been structurally characterized. The structures of the bis-sulfonamide systems are similar to the well-studied bis(amide) ferrocene compounds. Intermolecular hydrogen bonding is observed, typically between NH and SO groups of neighboring sulfonamides. However in the bis(GABA) derivative, intermolecular NH to CO hydrogen bonding interactions are present.

Second harmonic generation by all-optical poling and its relaxation in the polymer films containing azo sulfonamide chromophores

NASA Astrophysics Data System (ADS)

Ortyl, E.; Chan, S. W.; Nunzi, J.-M.; Kucharski, S.

2006-11-01

Polyurethane polymers containing azo sulfonamide chromophores were obtained by coupling reaction of the precursor polyurethane with corresponding diazonium salts. The chromophores, showing high hyperpolarizability value on molecular scale, were found to undergo orientation by all-optical poling method yielding macroscopic nonlinear optical response. The rate of generation and decay of the second-order nonlinear susceptibility was evaluated as a function of time. It was established that the polymers containing sulfonamide type chromophores showed higher stability of the nonlinear optical signal as compared with those modified with a nitro-acceptor groups of the Disperse Red type.

SYNERGISTIC EFFECT OF HALIDE IONS ON THE CORROSION INHIBITION OF MILD STEEL IN SULPHURIC ACID USING METHYL, N-METHYL ETHYL AND ETHYL SUBSTITUTED γ-2,c-6-DIPHENYL PIPERIDIN-4-ONE SEMICARBAZONES

NASA Astrophysics Data System (ADS)

Priya, V. Shanmuga; Rani, C. Uma; Velrani, S.

The synergistic effect of halide ions such as KCl, KBr and KI on the corrosion inhibition of mild steel in 1 N sulphuric acid by γ-2,c-6-diphenyl-t-3-methyl piperdin-4-ones with semicarbazone (01SC), γ-2,c-6-diphenyl-N-methyl-t-3-ethyl piperdin-4-ones with semicarbazone (02SC) and 2,6-diphenyl-t-3-ethyl piperdin-4-one with semicarbazone (03SC) has been examined by weight loss method, potentiodynamic polarization measurements and electrochemical AC impedance spectroscopy. Results show that substituted γ-2,c-6-diphenyl piperidin-4-ones with semicarbazone act as the perfect corrosion inhibitors and their inhibition efficiency increases with the addition of halide ions. The inhibitor (01SC) shows the inhibition efficiency of 78.28% (0.2mM) by using a weight loss method. The influence of I-, Br- and Cl- anions raises the inhibition efficiency of the substituted 2,6-diphenyl piperidin-4-ones with semicarbazone due to the synergistic effect. The synergistic effect of halide ions was formed in the following order: KI > KBr > KCl.

21 CFR 862.3850 - Sulfonamide test system.

Code of Federal Regulations, 2013 CFR

2013-04-01

... 21 Food and Drugs 8 2013-04-01 2013-04-01 false Sulfonamide test system. 862.3850 Section 862.3850 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Toxicology Test Systems § 862...

21 CFR 862.3850 - Sulfonamide test system.

Code of Federal Regulations, 2014 CFR

2014-04-01

... 21 Food and Drugs 8 2014-04-01 2014-04-01 false Sulfonamide test system. 862.3850 Section 862.3850 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Toxicology Test Systems § 862...

21 CFR 862.3850 - Sulfonamide test system.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 8 2011-04-01 2011-04-01 false Sulfonamide test system. 862.3850 Section 862.3850 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Toxicology Test Systems § 862...

21 CFR 862.3850 - Sulfonamide test system.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 21 Food and Drugs 8 2012-04-01 2012-04-01 false Sulfonamide test system. 862.3850 Section 862.3850 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Toxicology Test Systems § 862...

Deciphering the bacterial microbiome in huanglongbing-affected citrus treated with thermotherapy and sulfonamide antibiotics

USDA-ARS?s Scientific Manuscript database

Huanglongbing (HLB) is a serious citrus disease that threatens the citrus industry. In previous studies, sulfonamide antibiotics and heat treatment suppressed ‘Candidatus Liberibacter asiaticus’ (Las), but did not completely eliminate the Las. Furthermore, there are few reports studying the bacteria...

[Ethyl chloride aerosol spray for local anesthesia before arterial puncture: randomized placebo-controlled trial].

PubMed

Ballesteros-Peña, Sendoa; Fernández-Aedo, Irrintzi; Vallejo-De la Hoz, Gorka

2017-06-01

To compare the efficacy of an ethyl chloride aerosol spray to a placebo spray applied in the emergency department to the skin to reduce pain from arterial puncture for blood gas analysis. Single-blind, randomized placebo-controlled trial in an emergency department of Hospital de Basurto in Bilbao, Spain. We included 126 patients for whom arterial blood gas analysis had been ordered. They were randomly assigned to receive application of the experimental ethyl chloride spray (n=66) or a placebo aerosol spray of a solution of alcohol in water (n=60). The assigned spray was applied just before arterial puncture. The main outcome variable was pain intensity reported on an 11-point numeric rating scale. The median (interquartile range) pain level was 2 (1-5) in the experimental arm and 2 (1-4.5) in the placebo arm (P=.72). Topical application of an ethyl chloride spray did not reduce pain caused by arterial puncture.

Crystal structure of N-(1-allyl-3-chloro-4-eth-oxy-1H-indazol-5-yl)-4-meth-oxybenzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2014-09-01

In the title compound, C19H20ClN3O4S, the benzene ring is inclined to the indazole ring system (r.m.s. deviation = 0.014 Å) by 65.07 (8)°. The allyl and eth-oxy groups are almost normal to the indazole ring, as indicated by the respective torsion angles [N-N-C-C = 111.6 (2) and C-C-O-C = -88.1 (2)°]. In the crystal, mol-ecules are connected by N-H⋯N hydrogen bonds, forming helical chains propagating along [010]. The chains are linked by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Fate of sulfonamide antibiotics in contact with activated sludge--sorption and biodegradation.

PubMed

Yang, Sheng-Fu; Lin, Cheng-Fang; Wu, Chien-Ju; Ng, Kok-Kwang; Lin, Angela Yu-Chen; Hong, Pui-Kwan Andy

2012-03-15

The sorption and biodegradation of three sulfonamide antibiotics, namely sulfamethoxazole (SMX), sulfadimethoxine (SDM), and sulfamonomethoxine (SMM), in an activated sludge system were investigated. Experiments were carried out by contacting 100 μg/L of each sulfonamide compound individually with 2.56 g/L of MLSS at 25±0.5 °C, pH 7.0, and dissolved oxygen of 3.0±0.1 mg/L in a batch reactor over different periods of 2 d and 14 d. All sulfonamides were removed completely over 11-13 d. Sorptive equilibrium was established well within the first few hours, followed by a lag period of 1-3 days before biodegradation was to deplete the antibiotic compounds linearly in the ensuing 10 days. Apparent zeroth-order rate constants were obtained by regression analysis of measured aqueous concentration vs. time profiles to a kinetic model accounting for sorption and biodegradation; they were 8.1, 7.9, and 7.7 μg/L/d for SDM, SMX, and SMM, respectively, at activated sludge concentration of 2.56 g/L. The measured kinetics implied that with typical hydraulic retention time (e.g. 6 h) provided by WWTP the removal of sulfonamide compounds from the wastewater during the activated sludge process would approximate 2 μg/L. Copyright © 2011 Elsevier Ltd. All rights reserved.

Sorption of fluoroquinolones and sulfonamides in 13 Brazilian soils.

PubMed

Leal, Rafael Marques Pereira; Alleoni, Luis Reynaldo Ferracciú; Tornisielo, Valdemar Luiz; Regitano, Jussara Borges

2013-08-01

Animal production is a leading economic activity in Brazil and antibiotics are widely used. However, the occurrence, behavior, and impacts of antibiotics in Brazilian soils are still poorly known. We evaluated the sorption behavior of four fluoroquinolones (norfloxacin, ciprofloxacin, danofloxacin, and enrofloxacin) and five sulfonamides (sulfadiazine, sulfachloropyridazine, sulfamethoxazole, sulfadimidine, and sulfathiazole) in 13 Brazilian soils with contrasting physical, chemical, and mineralogical properties. Fluoroquinolone sorption was very high (Kd≥544 L kg(-1)) whereas sulfonamide sorption ranged from low to high (Kd=0.7-70.1 L kg(-1)), consistent with previous reports in the literature. Soil texture and cation exchange capacity were the soil attributes that most affected sorption. Cation exchange was the most important sorption mechanism for the fluoroquinolones in highly weathered tropical soils, although cation bridging and ion pairing could not be ruled out. Hydrophobic partition played an important role in the sorption of the sulfonamides, but sorption was also affected by non-hydrophobic interactions with organic and/or mineral surfaces. Sorption for both compound classes tended to be higher in soils with high Al and Fe oxihydroxide contents, but they were not correlated with Kd values. No direct effect of soil pH was seen. The fluoroquinolones are not expected to leach even in worst-case scenarios (soils rich in sand and poor in organic carbon), whereas soil attributes dictate leaching potential for the sulfonamides. Copyright © 2013 Elsevier Ltd. All rights reserved.

Upper limits for the ethyl-cyanide abundances in TMC-1 and L134N - Chemical implications

NASA Technical Reports Server (NTRS)

Minh, Y. C.; Irvine, W. M.

1991-01-01

Interstellar ethyl-cyanide has been sought via its 2(02)-1(01) transition towards two cold, dark clouds, and upper limits of the total column densities of 3 x 10 to the 12th/sq cm and 2 x 10 to the 12th/sq cm for TMC-1 and L134N, respectively. The 2(02)-1(01) transition of vynil cyanide, previously identified in TMC-1 by Matthews and Sears (1983b), was also observed. The detection of vinyl cyanide and the nondetection of ethyl cyanide in TMC-1 are consistent with gas phase ion-molecule chemical models, and there is thus no necessity of invoking grain surface synthesis for vinyl cyanide in cold clouds.

Novel sull binary vectors enable an inexpensive foliar selection method in Arabidopsis

USDA-ARS?s Scientific Manuscript database

Sulfonamide resistance is conferred by the sulI gene found on many Enterobacteriaceae R plasmids and Tn21 type transposons. The sulI gene encodes a sulfonamide insensitive dihydropteroate synthase enzyme required for folate biosynthesis. Transformation of tobacco, potato or Arabidopsis using sulI as...

Multicomponent ternary cocrystals of the sulfonamide group with pyridine-amides and lactams.

PubMed

Bolla, Geetha; Nangia, Ashwini

2015-11-04

SMBA was selected as a bifunctional sulfa drug to design ternary cocrystals with pyridine amides and lactam coformers. Supramolecular assembly of five ternary cocrystals of p-sulfonamide benzoic acid with nicotinamide and 2-pyridone is demonstrated and reproducible heterosynthons are identified for crystal engineering.

Telotristat Ethyl, a Tryptophan Hydroxylase Inhibitor for the Treatment of Carcinoid Syndrome.

PubMed

Kulke, Matthew H; Hörsch, Dieter; Caplin, Martyn E; Anthony, Lowell B; Bergsland, Emily; Öberg, Kjell; Welin, Staffan; Warner, Richard R P; Lombard-Bohas, Catherine; Kunz, Pamela L; Grande, Enrique; Valle, Juan W; Fleming, Douglas; Lapuerta, Pablo; Banks, Phillip; Jackson, Shanna; Zambrowicz, Brian; Sands, Arthur T; Pavel, Marianne

2017-01-01

Purpose Preliminary studies suggested that telotristat ethyl, a tryptophan hydroxylase inhibitor, reduces bowel movement (BM) frequency in patients with carcinoid syndrome. This placebo-controlled phase III study evaluated telotristat ethyl in this setting. Patients and Methods Patients (N = 135) experiencing four or more BMs per day despite stable-dose somatostatin analog therapy received (1:1:1) placebo, telotristat ethyl 250 mg, or telotristat ethyl 500 mg three times per day orally during a 12-week double-blind treatment period. The primary end point was change from baseline in BM frequency. In an open-label extension, 115 patients subsequently received telotristat ethyl 500 mg. Results Estimated differences in BM frequency per day versus placebo averaged over 12 weeks were -0.81 for telotristat ethyl 250 mg ( P < .001) and ‒0.69 for telotristat ethyl 500 mg ( P < .001). At week 12, mean BM frequency reductions per day for placebo, telotristat ethyl 250 mg, and telotristat ethyl 500 mg were -0.9, -1.7, and -2.1, respectively. Responses, predefined as a BM frequency reduction ≥ 30% from baseline for ≥ 50% of the double-blind treatment period, were observed in 20%, 44%, and 42% of patients given placebo, telotristat ethyl 250 mg, and telotristat ethyl 500 mg, respectively. Both telotristat ethyl dosages significantly reduced mean urinary 5-hydroxyindole acetic acid versus placebo at week 12 ( P < .001). Mild nausea and asymptomatic increases in gamma-glutamyl transferase were observed in some patients receiving telotristat ethyl. Follow-up of patients during the open-label extension revealed no new safety signals and suggested sustained BM responses to treatment. Conclusion Among patients with carcinoid syndrome not adequately controlled by somatostatin analogs, treatment with telotristat ethyl was generally safe and well tolerated and resulted in significant reductions in BM frequency and urinary 5-hydroxyindole acetic acid.

(S)-N-[1-(5-Benzyl-sulfan-yl-1,3,4-oxa-diazol-2-yl)-2-phenyl-eth-yl]-4-methyl-benzene-sulfonamide.

PubMed

Syed, Tayyaba; Hameed, Shahid; Jones, Peter G

2011-11-01

The title compound, C(24)H(23)N(3)O(3)S(2), crystallizes with two independent mol-ecules in the asymmetric unit. They differ essentially in the orientation of the tolyl rings, between which there is π-π stacking (centroid-centroid distance = 3.01 Å). The absolute configuration was confirmed by the determination of the Flack parameter [x = 0.008 (9)]. In the crystal, mol-ecules are connected by two classical N-H⋯N hydrogen bonds and two weak but very short C-H⋯O(sulfon-yl) inter-actions, forming layers lying parallel to the bc plane.

Effect of perfluorooctane sulfonate on the conformation of wheat germ acid phosphatase.

PubMed

Xu, Dongmei; Jin, Jianchang; Shen, Tong; Wang, Yanhua

2013-11-01

Fluorescence spectroscopy was used to study the quenching mechanism, the type of force and the binding sites of perfluorooctane sulfonate (PFOS) on wheat germ acid phosphatase (ACPase). The results showed that the quenching effect of PFOS on ACPase was mainly due to a static quenching mechanism that occurred via the formation of hydrogen bonds and van der Waals forces. The results from synchronous fluorescence spectroscopy demonstrated that PFOS interacts with ACPase close to the tryptophan residues. In addition, synchronous fluorescence spectroscopy also showed that PFOS increases the hydrophobicity of the microenvironment of the tyrosine residues, hence decreasing the local polarity.

Perfluorocarbon compounds: transmitting liquids for infrared laser tissue ablation

NASA Astrophysics Data System (ADS)

Frenz, Martin; Pratisto, Hans S.; Toth, Cynthia A.; Jansen, E. Duco; Altermatt, Hans J.; Welch, Ashley J.; Weber, Heinz P.

1996-05-01

One concern during IR-laser ablation of tissue under water is the mechanical injury that may be induced in tissue due to rapid bubble expansion and collapse or due to strong laser-induced pressure waves. The objective of this study was to evaluate the feasibility of using a liquid which is transparent to the IR-region of the spectrum in order to minimize these undesired mechanical side-effects. As transmitting medium perfluorocarbon liquid was used. Free- running Er:YAG and Ho:YAG laser pulses were delivered into the liquid via a 400 micrometers fiber. Bubble formation during the ablation process was recorded with fast flash photography while pressure transients were measured with a needle hydrophone. The effect of the surrounding material (air, water, perfluorooctane) on the tissue response of chicken breast was evaluated in vitro using histology. It was observed that a large bubble (up to 6 mm in diameter) was formed under perfluorooctane driven by the ablation products. This bubble, however, does not generate a pressure wave when collapsing. Although perfluorooctane only shows a weak absorption for infrared radiation, laser-induced thermal lensing in the liquid strongly decreases the radiant exposure and therefore the ablation efficiency.

Rotational isomers of N-(β-phenylpropionyl)alanine ethyl dithioester: a Raman spectroscopic and MO study

NASA Astrophysics Data System (ADS)

Fausto, R.; Teixeira-Dias, J. J. C.; Tonge, P. J.; Carey, P. R.

1994-07-01

Raman spectra of N-(β-phenylpropionyl)alanine ethyl dithioester (C 6H 5CH 2CH 2C(O)NHCH(CH 3)C(S)SC 2H 5) in CCl 4 and CH 3CN solutions were measured as a function of temperature and the enthalpy differences (Δ H) between rotational isomers differing by internal rotation around the NHCH(CH 3) and CH(CH 3)C(S) bonds (forms A, B and C 5) were evaluated from relative band intensities. The spectroscopic results are consistent with a greater thermodynamical stability of the B-type conformer, where the N and S (thiol) atoms are in close contact. In addition, a comparison of the measured Δ H(A-B) for the present molecules with previously reported values for a series of similar glycine-based ethyl dithioesters shows that the presence of the extra CH 3 group at the α-carbon atom leads to a stabilization of the B-type conformer relative to the A-type form in the alanine-based dithioester. Semiempirical AM1 molecular orbital calculations were also performed on the title molecule and on its glycine analogue, N(β-phenylpropionyl)glycine ethyl dithioester. In general terms, the results of these calculations agree with the experimental findings, thus providing good theoretical support for the experimental data.

Gradient x Isocratic Elution CCC on the Isolation of Verbascoside and Other Phenylethanoids: Influence of the Complexity of the Matrix.

PubMed

Leitão, Gilda Guimarães; Pinto, Shaft Correa; de Oliveira, Danilo Ribeiro; Timoteo, Patrícia; Guimarães, Michelle Guedes; Cordova, Wilmer H Perera; Leitão, Suzana Guimarães

2015-11-01

Verbascoside is a phenylethanoid glycoside widely distributed in nature, especially among the order Lamiales, occurring in numerous plants that are constituents of folk medicine preparations. This natural compound, previously isolated by our group from the ethyl acetate extract of Lantana trifolia using the gradient approach in countercurrent chromatography, was now isolated from the butanol extract of the same plant and from Lippia alba f. intermedia (Verbenaceae) using countercurrent chromatography in either gradient or isocratic elution modes. The ethyl acetate extract of L. alba, rich in phenylethanoids and flavonoids, was fractionated using countercurrent chromatography in the step-gradient elution approach. The four-step solvent system was composed of n-hexane-ethyl acetate-n-butanol-water (4 : 10 : X : 10), where X = 1 (solvent system A), 3 (solvent system B), 5 (solvent system C), and 7 (solvent system D), and allowed for the isolation of verbascoside along with other phenylethanoids and flavonoids from both plants. Verbascoside and 2'-O-β-apiosylverbascoside were further isolated from the n-butanol extract of L. trifolia using the solvent system ethyl acetate-n-butanol-water 10 : 2 : 10 on an isocratic run. The difference in the complexity of the two plant extracts demanded different purification steps, which included a second high-speed countercurrent chromatography purification using the isocratic elution mode. Georg Thieme Verlag KG Stuttgart · New York.

2'-O-[2-[2-(N,N-Dimethylamino)ethoxy]ethyl] Modified Antisense Oligonucleotides: Symbiosis of Charge Interaction Factors and Stereoelectronic Effects

DOE Office of Scientific and Technical Information (OSTI.GOV)

Prhavc, M.; Prakash, T.P.; Minasov, G.

Oligonucleotides with a novel, 2'-O-[2-[2-(N,N-dimethylamino)ethoxy]ethyl] (2'-O-DMAEOE) modification have been synthesized. This modification, a cationic analogue of the 2'-O-(2-methoxyethyl) (2'-O-MOE) modification, exhibits high binding affinity to target RNA (but not to DNA) and exceptional resistance to nuclease degradation. Analysis of the crystal structure of a self-complementary oligonucleotide containing a single 2'-O-DMAEOE modification explains the importance of charge factors and gauche effects on the observed antisense properties. 2'-O-DMAEOE modified oligonucleotides are ideal candidates for antisense drugs.

Multiresidue analysis of 22 sulfonamides and their metabolites in animal tissues using quick, easy, cheap, effective, rugged, and safe extraction and high resolution mass spectrometry (hybrid linear ion trap-Orbitrap).

PubMed

Abdallah, H; Arnaudguilhem, C; Jaber, F; Lobinski, R

2014-08-15

A new high performance liquid chromatography-high resolution mass spectrometry (HPLC-HRMS) method was developed for a simultaneous multi-residue analysis of 22 sulfonamides (SAs) and their metabolites in edible animal (pig, beef, sheep and chicken) tissues. Sample preparation was optimized on the basis of the "QuEChERS" protocol. The analytes were identified using their LC retention times and accurate mass; the identification was further confirmed by multi-stage high mass accuracy (<5ppm) mass spectrometry. The performance of the method was evaluated according to the EU guidelines for the validation of screening methods for the analysis of veterinary drugs residues. Acceptable values were obtained for: linearity (R(2)<0.99), limit of detection (LOD, 3-26μg/kg), limit of quantification (LOQ, 11-88μg/kg), accuracy (recovery 88-112%), intra- and inter-day precision 1-14 and 1-17%, respectively, decision limit (CCα) and detection capability (CCβ) around the maximum residue limits (MRL) of SAs (100μg/kg). The method was validated by analysis of a reference material FAPAS-02188 "Pig kidney" with ǀ Z-scoreǀ<0.63. The method was applied to various matrices (kidney, liver, muscle) originated from pig, beef, sheep, and chicken) allowing the simultaneous quantification of target sulfonamides at concentration levels above the MRL/2 and the identification of untargeted compounds such as N(4)-acetyl metabolites using multi-stage high mass accuracy mass spectrometry. Copyright © 2014 Elsevier B.V. All rights reserved.

Increased levels of the acetaldehyde-derived DNA adduct N 2-ethyldeoxyguanosine in oral mucosa DNA from Rhesus monkeys exposed to alcohol

PubMed Central

Balbo, Silvia; Juanes, Rita Cervera; Khariwala, Samir; Baker, Erich J.; Daunais, James B.; Grant, Kathleen A.

2016-01-01

Alcohol is a human carcinogen. A causal link has been established between alcohol drinking and cancers of the upper aerodigestive tract, colon, liver and breast. Despite this established association, the underlying mechanisms of alcohol-induced carcinogenesis remain unclear. Various mechanisms may come into play depending on the type of cancer; however, convincing evidence supports the concept that ethanol’s major metabolite acetaldehyde may play a major role. Acetaldehyde can react with DNA forming adducts which can serve as biomarkers of carcinogen exposure and potentially of cancer risk. The major DNA adduct formed from this reaction is N 2-ethylidenedeoxyguanosine, which can be quantified as its reduced form N 2-ethyl-dG by LC-ESI-MS/MS. To investigate the potential use of N 2-ethyl-dG as a biomarker of alcohol-induced DNA damage, we quantified this adduct in DNA from the oral, oesophageal and mammary gland tissues from rhesus monkeys exposed to alcohol drinking over their lifetimes and compared it to controls. N 2-Ethyl-dG levels were significantly higher in the oral mucosa DNA of the exposed animals. Levels of the DNA adduct measured in the oesophageal mucosa of exposed animals were not significantly different from controls. A correlation between the levels measured in the oral and oesophageal DNA, however, was observed, suggesting a common source of formation of the DNA adducts. N 2-Ethyl-dG was measured in mammary gland DNA from a small cohort of female animals, but no difference was observed between exposed animals and controls. These results support the hypothesis that acetaldehyde induces DNA damage in the oral mucosa of alcohol-exposed animals and that it may play role in the alcohol-induced carcinogenic process. The decrease of N 2-ethyl-dG levels in exposed tissues further removed from the mouth also suggests a role of alcohol metabolism in the oral cavity, which may be considered separately from ethanol liver metabolism in the investigation of ethanol-related cancer risk. PMID:27056945

Perfluoroalkyl Acids (PFAAs) and Selected Precursors in the Baltic Sea Environment: Do Precursors Play a Role in Food Web Accumulation of PFAAs?

PubMed

Gebbink, Wouter A; Bignert, Anders; Berger, Urs

2016-06-21

The present study examined the presence of perfluoroalkyl acids (PFAAs) and selected precursors in the Baltic Sea abiotic environment and guillemot food web, and investigated the relative importance of precursors in food web accumulation of PFAAs. Sediment, water, zooplankton, herring, sprat, and guillemot eggs were analyzed for perfluoroalkane sulfonic acids (PFSAs; C4,6,8,10) and perfluoroalkyl carboxylic acids (PFCAs; C6-15) along with six perfluoro-octane sulfonic acid (PFOS) precursors and 11 polyfluoroalkyl phosphoric acid diesters (diPAPs). FOSA, FOSAA and its methyl and ethyl derivatives (Me- and EtFOSAA), and 6:2/6:2 diPAP were detected in sediment and water. While FOSA and the three FOSAAs were detected in all biota, a total of nine diPAPs were only detected in zooplankton. Concentrations of PFOS precursors and diPAPs exceeded PFOS and PFCA concentrations, respectively, in zooplankton, but not in fish and guillemot eggs. Although PFOS precursors were present at all trophic levels, they appear to play a minor role in food web accumulation of PFOS based on PFOS precursor/PFOS ratios and PFOS and FOSA isomer patterns. The PFCA pattern in fish could not be explained by the intake pattern based on PFCAs and analyzed precursors, that is, diPAPs. Exposure to additional precursors might therefore be a dominant exposure pathway compared to direct PFCA exposure for fish.

Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives.

PubMed

Antoniadis, Constantinos D; Blake, Alexander J; Hadjikakou, Sotiris K; Hadjiliadis, Nick; Hubberstey, Peter; Schröder, Martin; Wilson, Claire

2006-08-01

The structures of four selenium analogues of the antithyroid drug 6-n-propyl-2-thiouracil [systematic name: 2,3-dihydro-6-n-propyl-2-thioxopyrimidin-4(1H)-one], namely 6-methyl-2-selenouracil, C(5)H(6)N(2)OSe (1), 6-ethyl-2-selenouracil, C(6)H(8)N(2)OSe (2), 6-n-propyl-2-selenouracil, C(7)H(10)N(2)OSe (3), and 6-isopropyl-2-selenouracil, C(7)H(10)N(2)OSe (4), are described, along with that of the dichloromethane monosolvate of 6-isopropyl-2-selenouracil, C(7)H(10)N(2)OSe.CH(2)Cl(2) (4.CH(2)Cl(2)). The extended structure of (1) is a two-dimensional sheet of topology 6(3) with a brick-wall architecture. The extended structures of (2) and (4) are analogous, being based on a chain of eight-membered R(8)(6)(32) hydrogen-bonded rings. In (3) and (4.CH(2)Cl(2)), R(2)(2)(8) hydrogen bonding links molecules into chains. 6-n-Propyl-2-selenouracil.I(2), C(7)H(10)N(2)OSe.I(2) (7), is a charge-transfer complex with a ;spoke' structure, the extended structure of which is based on a linear chain formed principally by intermolecular N-H...O hydrogen bonds. Re-crystallization of 6-ethyl-2-selenouracil or (7) from acetone gave crystals of the diselenides [N-(6'-ethyl-4'-pyrimidone)(6-ethyl-2-selenouracil)(2)(Se-Se)].2H(2)O (9.2H(2)O) or [N-(6'-n-propyl-4'-pyrimidone)(6-n-propyl-2-selenouracil)(2)(Se-Se)] (10), respectively: these have similar extended chain structures formed via N-H...O and C-H...O hydrogen bonds, stacked to give two-dimensional sheets. Re-crystallization of (7) from methanol/acetonitrile led via deselenation to the formation of crystals of 6-n-propyl-2-uracil (11), in which six symmetry-related molecules combine to form a six-membered R(6)(6)(24) hydrogen-bonded ring, with each pair of molecules linked by an R(2)(2)(8) motif.

Investigation of antigen-antibody interactions of sulfonamides with a monoclonal antibody in a fluorescence polarization immunoassay using 3D-QSAR models

USDA-ARS?s Scientific Manuscript database

A three-dimensional quantitative structure-activity relationship (3D-QSAR) model of sulfonamide analogs binding a monoclonal antibody (MAbSMR) produced against sulfamerazine was carried out by Distance Comparison (DISCOtech), comparative molecular field analysis (CoMFA), and comparative molecular si...

Highly broad-specific and sensitive enzyme-linked immunosorbent assay for screening sulfonamides: Assay optimization and application to milk samples

USDA-ARS?s Scientific Manuscript database

A broad-specific and sensitive immunoassay for the detection of sulfonamides was developed by optimizing the conditions of an enzyme-linked immunosorbent assay (ELISA) in regard to different monoclonal antibodies (MAbs), assay format, immunoreagents, and several physicochemical factors (pH, salt, de...

STUDIES ON THE MECHANISM OF RECOVERY IN PNEUMOCOCCAL PNEUMONIA

PubMed Central

Wood, W. Barry; McLeod, Charlotte; Irons, Edwin N.

1946-01-01

The phagocytosis which occurs in the lungs of rats receiving sulfonamide is due neither to an opsonizing action of the sulfonamides nor to type-specific antibody. The evidence presented indicates that the destruction of the pneumococci is brought about by a phagocytic mechanism independent of both opsonization and capsular injury. PMID:19871576

Hydroxide as general base in the saponification of ethyl acetate.

PubMed

Mata-Segreda, Julio F

2002-03-13

The second-order rate constant for the saponification of ethyl acetate at 30.0 degrees C in H(2)O/D(2)O mixtures of deuterium atom fraction n (a proton inventory experiment) obeys the relation k(2)(n) = 0.122 s(-1) M(-1) (1 - n + 1.2n) (1 - n + 0.48n)/(1 - n + 1.4n) (1 - n + 0.68n)(3). This result is interpreted as a process where formation of the tetrahedral intermediate is the rate-determining step and the transition-state complex is formed via nucleophilic interaction of a water molecule with general-base assistance from hydroxide ion, opposite to the direct nucleophilic collision commonly accepted. This mechanistic picture agrees with previous heavy-atom kinetic isotope effect data of Marlier on the alkaline hydrolysis of methyl formate.

Simultaneous occurrence of nitrates and sulfonamide antibiotics in two ground water bodies of Catalonia (Spain)

NASA Astrophysics Data System (ADS)

García-Galán, M. ^a. Jesús; Garrido, Teresa; Fraile, Josep; Ginebreda, Antoni; Díaz-Cruz, M. Silvia; Barceló, Damià

2010-03-01

SummaryIn the present work the occurrence of 19 selected sulfonamides, including one acetylated metabolite, was investigated in ground water samples taken from two ground water bodies in Catalonia (Plana de Vic and La Selva). Both include areas designated as nitrate vulnerable zones, according to Directive 91/676/EEC. A fully automated analytical methodology based on on-line solid-phase extraction-liquid chromatography-tandem mass spectrometry (on-line SPE-LC-MS/MS) was developed for this purpose. The high selectivity and sensitivity achieved (limits of detection between 0.005 and 0.8 ng/L) permitted to demonstrate the ubiquity of these antibiotics in both ground water bodies. Results showed a wide range of concentrations, from 0.01 ng/L up to 3460.57 ng/L. Since sulfonamides are related to livestock veterinary practices, they can be used as a specific indicator of manure contamination. However, the presence of sulfonamides appeared not to be directly related to the concentration of nitrates, as it is reflected on the low correlation coefficients found.

Competitive sorption affinity of sulfonamides and chloramphenicol antibiotics toward functionalized biochar for water and wastewater treatment.

PubMed

Ahmed, Mohammad Boshir; Zhou, John L; Ngo, Huu Hao; Guo, Wenshan; Johir, Md Abu Hasan; Belhaj, Dalel

2017-08-01

Competitive sorption of sulfamethazine (SMT), sulfamethoxazole (SMX), sulfathiazole (STZ) and chloramphenicol (CP) toward functionalized biochar (fBC) was highly pH dependent with maximum sorption at pH ∼4.0-4.25. Equilibrium data were well represented by the Langmuir and Freundlich models in the order STZ>SMX>CP>SMT. Kinetics data were slightly better fitted by the pseudo second-order model than pseudo first-order and intra-particle-diffusion models. Maximum sorptive interactions occurred at pH 4.0-4.25 through H-bonds formations for neutral sulfonamides species and through negative charge assisted H-bond (CAHB) formation for CP, in addition to π-π electron-donor-acceptor (EDA) interactions. EDA was the main mechanism for the sorption of positive sulfonamides species and CP at pH<2.0. Sorption of negative sulfonamides species and CP at pH>7.0 was regulated by H-bond formation and proton exchange with water by forming CAHB, respectively. The results suggested fBC to be highly efficient in removing antibiotics mixture. Copyright © 2017 Elsevier Ltd. All rights reserved.

Assessing the sorption and leaching behaviour of three sulfonamides in pasture soils through batch and column studies.

PubMed

Srinivasan, Prakash; Sarmah, Ajit K

2014-09-15

We investigated the sorption potential and transport behaviour of three sulfonamides, namely, sulfamethoxazole (SMO), sulfachloropyridazine (SCP) and sulfamethazine (SM), and a conservative bromide tracer (Br(-)) in two undisturbed soil columns collected from the dairy farming regions in the North Island of New Zealand. Based on the low log Koc values obtained from the sorption study, all three sulfonamides are likely to have high mobility, making them a potential threat to surface and ground water. Soil column studies also showed that the mobility of the sulfonamides varied among soils and antibiotic type. Sulfonamides exhibited a mobility pattern similar to that of conservative Br(-) tracer. Considerable retardation was observed for the Hamilton soil, and the delayed peak arrival time (or maxima) was due to the role of sorption-related retention processes under saturated flow conditions. Residual antibiotic concentrations for SMO and SCP were detected in all soil sections including at 18 cm depth, while no resident concentration of SM was detected at any depth in the entire length of the core for both soils. The deterministic, physical equilibrium model (CXTFIT) described the peak arrival time as well as the maximum concentration of the antibiotic breakthrough curves reasonably, but showed some underestimation at the advanced stages of the leaching process. There was a significant difference in the model estimated retardation factors obtained from column study and the experimental retardation factors obtained from the conventional batch sorption experiments. Copyright © 2014 Elsevier B.V. All rights reserved.

Residues of selected antibiotics in the South Moravian Rivers, Czech Republic.

PubMed

Jarova, Katerina; Vavrova, Milada; Koleckarova, Alice

2015-01-01

The aim of this study was to assess the contamination level of aquatic ecosystems of the Oslava and the Jihlava Rivers, and of the Nove Mlyny Water Reservoir, situated in the South Moravian Region (Czech Republic), by residues of selected veterinary pharmaceuticals. We isolated and determined 10 sulfonamide antibiotics in samples of surface water and bottom sediments using optimized analytical methods. A representative number of sampling sites in the entire basin of selected waters were chosen. Samples were collected particularly near the larger cities in order to assess their possible impact to the aquatic ecosystems. Extraction, pre-concentration and purification of samples were performed using optimized methods of solid phase extraction and pressurized solvent extraction. Final identification and quantification were carried out by high-performance liquid chromatography coupled with diode array detector. The concentration of sulfonamides in water samples were all under the limit of detection. Regarding sediment samples, sulfadimidine was found at most sampling sites; its highest values were recorded in the Jihlava River (up to 979.8 µg.kg(-1) dry matter). Other frequently detected sulfonamides were sulfamethoxazole and sulfamerazine. Most other sulfonamides were under the limit of detection or limit of quantification. Monitoring of antibiotic residues in the environment, especially in the aquatic ecosystem, is a current topic due to the growing worldwide use in both human and veterinary medicine. According to obtained results, we document the pollution of selected rivers and water reservoir by particular sulfonamides which basically reflects their application in veterinary medicine.

Occurrence and transport of tetracycline, sulfonamide, quinolone, and macrolide antibiotics in the Haihe River Basin, China.

PubMed

Luo, Yi; Xu, Lin; Rysz, Michal; Wang, Yuqiu; Zhang, Hao; Alvarez, Pedro J J

2011-03-01

The occurrence and transport of 12 antibiotics (from the tetracycline, sulfonamide, quinolone, and macrolide families) was studied in a 72-km stretch of the Haihe River, China, and in six of its tributaries. Aqueous and sediment samples were analyzed by HPLC-MS/MS. Sulfonamides were detected at the highest concentrations (24-385 ng/L) and highest frequencies (76-100%). Eight of the 12 antibiotics likely originated from veterinary applications in swine farms and fishponds, and concentrations at these sources (0.12-47 μg/L) were 1-2 orders of magnitude higher than in the effluent of local wastewater treatment plants. Sulfachloropyridazine (SCP) was detected in all swine farm and fishpond samples (maximum concentration 47 μg/L), which suggests its potential usefulness to indicate livestock source pollution in the Haihe River basin. Hydrological and chemical factors that may influence antibiotic distribution in the Haihe River were considered by multiple regression analysis. River flow rate exerted the most significant effect on the first-order attenuation coefficient (K) for sulfonamides, quinolones, and macrolides, with higher flow rates resulting in higher K, probably due to dilution. For tetracyclines, sediment total organic matter and cation exchange capacity exerted a greater impact on K than flow rate, indicating that adsorption to sediments plays an important role in attenuating tetracycline migration. Overall, the predominance of sulfonamides in the Haihe River underscores the need to consider regulating their veterinary use and improving the management and treatment of associated releases.

Evaluation of ionic liquids supported on silica as a sorbent for fully automated online solid-phase extraction with LC-MS determination of sulfonamides in bovine milk samples.

PubMed

da Silva, Meire Ribeiro; Mauro Lanças, Fernando

2018-03-10

Sulfonamides are antibiotics widely used in the treatment of diseases in dairy cattle. However, their indiscriminate use for disease control may lead to their presence in tissues and milk and their determination requires a sample preparation step as part of an analytical approach. Among the several sample preparation techniques available, those based upon the use of sorptive materials have been widely employed. Recently, the application of ionic liquids immobilized on silica surfaces or polymeric materials has been evaluated for such an application. This manuscript addresses the evaluation of silica-based ionic liquid obtained by a sol-gel synthesis process by basic catalysis as sorbent for online solid-phase extraction with liquid chromatography and electrospray ionization time-of-flight mass spectrometry for sulfonamides determination. Infrared vibrational spectroscopy confirmed the presence of the ionic liquid on the silica surface, suggesting that the ionic liquid was anchored on to the silica surface. Other sorbents varying the ionic liquid alkyl chain were also synthesized and evaluated by off-line solid-phase extraction in the sulfonamide extraction. As the length of the alkyl chain increased, the amount of extracted sulfonamides decreased, possibly due to a decrease in the electrostatic interaction caused by the reduction in the polarity, as well as the presence of a hexafluorophosphate anion that increases the hydrophobic character of the material. The use of 1-butyl-3-methylimidazolium hexafluorophosphate as a selective ionic liquid sorbent enabled the isolation and sulfonamide preconcentration in bovine milk by online solid-phase extraction with liquid chromatography and electrospray ionization time-of-flight mass spectrometry. The limit of quantification for the method developed was 5-7, 5 μg/mL, with extraction recoveries ranging between 74 and 93% and intra- and interassay between 1.5-12.5 and 2.3-13.1, respectively. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

N-(2-Allyl-4-eth­oxy-2H-indazol-5-yl)-4-methyl­benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Viale, Maurizio; Saadi, Mohamed; El Ammari, Lahcen

2014-01-01

The indazole ring system of the title compound, C19H21N3O3S, is almost planar (r.m.s. deviation = 0.0192 Å) and forms dihedral angles of 77.99 (15) and 83.9 (3)° with the benzene ring and allyl group, respectively. In the crystal, centrosymmetrically related mol­ecules are connected by pairs of N—H⋯O hydrogen bonds into dimers, which are further linked by C—H⋯O hydrogen bonds, forming columns parallel to the b axis. PMID:24860413

N-(1-Allyl-3-chloro-4-eth­oxy-1H-indazol-5-yl)-4-methyl­benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Bouissane, Latifa; Saadi, Mohamed; El Ammari, Lahcen

2014-01-01

In the title compound, C19H20ClN3O3S, the benzene ring is inclined to the indazole ring system by 51.23 (8)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers which stack in columns parallel to [011]. The atoms in the allyl group are disordered over two sets of sites with an occupancy ratio of 0.624 (8):0.376 (8). PMID:24940237

Effect of different fractions from hydroalcoholic extract of Black Maca (Lepidium meyenii) on testicular function in adult male rats.

PubMed

Yucra, Sandra; Gasco, Manuel; Rubio, Julio; Nieto, Jessica; Gonzales, Gustavo F

2008-05-01

To evaluate the effect of different fractions of Black Maca (Lepidium meyenii), obtained from the hydroalcoholic extract, on spermatogenesis. Animal study. Animal and laboratory facilities at a university. Forty two adult male rats from the Holtzman strain (3 months old). Hydroalcoholic extract of Black Maca was partitioned with the following solvents: petroleum ether, chloroform, ethyl acetate, n-butanol, and water to obtain each fraction. Forty-two rats were divided in different groups according the fraction administered and vehicle. The hydroalcoholic extract of Black Maca and its fractions and vehicle were given orally by gavage for 7 days. Daily sperm production, epididymal sperm count, and sperm count in the vas deferens. Daily sperm production was higher in the ethyl acetate group compared with all other groups. The epididymal sperm count was higher in rats treated with ethyl acetate fraction compared with rats treated with vehicle (control), petroleum ether, n-butanol, or water fractions. The sperm count in vas deferens was lower in rats treated with ethyl acetate, petroleum ether, or water fractions compared with the control group; thus, the sperm count in vas deferens in rats treated with chloroform and n-butanol fractions was higher than in the petroleum ether group. The greatest effect on spermatogenesis was observed in the ethyl acetate fraction from the hydroalcoholic extract of Black Maca, suggesting that the compounds related to the beneficial effect on sperm production of Black Maca are presented in this fraction. Antioxidant components could play a role in the effect of increased epididymal sperm concentration observed in the model.

76 FR 72311 - Hazardous Waste Management System; Identification and Listing of Hazardous Waste; Final Exclusion

Federal Register 2010, 2011, 2012, 2013, 2014

2011-11-23

... waste in any State with delisting authorization, Eastman Chemical must obtain delisting authorization... benzene, ethyl ether, methyl isobutyl ketone, n-butyl alcohol, cyclohexane, methanol. F005 Toluene, methyl... Isobutyl alcohol. U147 Maleic anhydride. U154 Methanol. U159 Methyl ethyl ketone. U161 Methyl isobutyl...

Cotinus coggyria: a rich source of antioxidants.

PubMed

Riaz, Tauheeda; Abbasi, Muhammad Athar; Aziz-ur-Rehman; Rubab, Kaniz; Shahzadi, Tayyaba; Ajaib, Muhammad; Khan, Khalid Mohammed

2012-07-01

Methanolic extract of Cotinus coggyria Scop. was mixed in distilled water and partitioned first with the n-hexane, then with chloroform, then ethyl acetate and at the end with n-butanol. The phytochemical screening of plant showed presence of the phenolics, cardiac glycosides and flavonoides in large amount in the chloroform, n-butanol and ethyl acetate soluble fraction. Antioxidant activity of these four fractions and the left behind aqueous fraction was measured by four methods such as: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity, ferric thiocyanate assay, ferric reducing antioxidant power (FRAP) assay and total antioxidant activity. Total phenolics were also measured. Noteworthy antioxidant potential was shown by the chloroform, n-butanol and ethyl acetate soluble fraction showed. Ethyl acetate fraction showed highest % inhibition of the DPPH radical when compared with the other studied fractions i.e. 81.64 ± 1.29% inhibition of the DPPH radical at the concentration of 30 μg/ml. Its IC(50) value was found to be 15.58 ± 0.09 μg/ml, comparative to the butylated hydroxytoluene (BHT), which has IC(50) value 12.6 ± 0.85μg/ml. This fraction also showed the highest lipid peroxidation inhibition (61.41 ± 1.16%), as well as highest values of FRAP (697.76 ± 1.98 μg of trolox equivalents) total antioxidant activity (1.02 ± 0.09) and total phenolic contents (229.34 ± 0.57) comparative to the other studied fractions. The chloroform and n-butanol soluble fraction also showed good results for all the studied antioxidant assays.

Acquired toxoplasmosis after orthotopic heart transplantation in a sulfonamide-allergic patient.

PubMed

Sanchez Mejia, Aura; Debrunner, Mark; Cox, Elaine; Caldwell, Randall

2011-01-01

We report the case of a young adult with a history of an allergic reaction to a sulfonamide antibiotic who developed toxoplasmosis after his second orthotopic heart transplant. As a result of this drug allergy, the patient did not receive prophylaxis with trimethoprim and sulfamethoxazole. He was successfully treated with clindamycin, pyrimethamine, and folic acid.

Hydroxylamine-O-sulfonamide is a versatile lead compound for the development of carbonic anhydrase inhibitors.

PubMed

Di Fiore, Anna; Vergara, Alessandro; Caterino, Marco; Alterio, Vincenzo; Monti, Simona M; Ombouma, Joanna; Dumy, Pascal; Vullo, Daniela; Supuran, Claudiu T; Winum, Jean-Yves; De Simone, Giuseppina

2015-07-21

Hydroxylamine-O-sulfonamide, a molecule incorporating two zinc-binding groups (ZBGs), has been investigated as a carbonic anhydrase inhibitor (CAI) by means of kinetic, crystallographic and Raman spectroscopy studies, highlighting interesting results on its mechanism of action. These data can be exploited to design new, effective and selective CAIs.

Simultaneous determination of 13 fluoroquinolone and 22 sulfonamide residues in milk by a dual-colorimetric enzyme-linked immunosorbent assay

USDA-ARS?s Scientific Manuscript database

Enzyme-linked immunosorbent assays (ELISAs) usually focus on the detection of a single analyte or a single group of analytes, e.g., fluoroquinolones or sulfonamides. However, it is often necessary to simultaneously monitor the two classes of antimicrobial residues in different food matrices. In th...

Inhibition of the α-carbonic anhydrase from Vibrio cholerae with amides and sulfonamides incorporating imidazole moieties.

PubMed

De Vita, Daniela; Angeli, Andrea; Pandolfi, Fabiana; Bortolami, Martina; Costi, Roberta; Di Santo, Roberto; Suffredini, Elisabetta; Ceruso, Mariangela; Del Prete, Sonia; Capasso, Clemente; Scipione, Luigi; Supuran, Claudiu T

2017-12-01

We discovered novel and selective sulfonamides/amides acting as inhibitors of the α-carbonic anhydrase (CA, EC 4.2.1.1) from the pathogenic bacterium Vibrio cholerae (VchCA). This Gram-negative bacterium is the causative agent of cholera and colonises the upper small intestine where sodium bicarbonate is present at a high concentration. The secondary sulfonamides and amides investigated here were potent, low nanomolar VchCA inhibitors whereas their inhibition of the human cytosolic isoforms CA I and II was in the micromolar range or higher. The molecules represent an interesting lead for antibacterial agents with a possibly new mechanism of action, although their CA inhibition mechanism is unknown for the moment.

Bromidotetra-kis-(1H-2-ethyl-5-methyl-imidazole-κN)copper(II) bromide.

PubMed

Godlewska, Sylwia; Baranowska, Katarzyna; Socha, Joanna; Dołęga, Anna

2011-12-01

The Cu(II) ion in the title compound, [CuBr(C(6)H(10)N(2))(4)]Br, is coordinated in a square-based-pyramidal geometry by the N atoms of four imidazole ligands and a bromide anion in the apical site. Both the Cu(II) and Br(-) atoms lie on a crystallographic fourfold axis. In the crystal, the [CuBr(C(6)H(10)N(2))(4)](+) complex cations are linked to the uncoordinated Br(-) anions (site symmetry [Formula: see text]) by N-H⋯Br hydrogen bonds, generating a three-dimensional network. The ethyl group of the imidazole ligand was modelled as disordered over two orientations with occupancies of 0.620 (8) and 0.380 (8).

Effect of fluorinated groups on photooxidative stability of polymeric protectives applied on marble.

PubMed

Chiantore, O; Poli, T; Colombo, C; Peruzzi, R; Toniolo, L

2001-01-01

Some new protective copolymers and a commercial one have been tested on Candoglia marble, a very low porosity stone. Two of the polymers contained a partially fluorinated methacrylic monomer, 2,2,2 trifluoro ethyl methacrylate (TFEMA), in combination with either an acrylic, methyl acrylate (MA) or a vinyl ether, n-butyl vinyl ether (n-BVE) unit. Two copolymers, ethyl methacrylate/n-butyl vinyl ether and ethyl methacrylate (EMA)/methyl acrylate (Paraloid B72), were non-fluorinated and similar in compositions and molar ratio. The aim of the work is to test the copolymers and compare the performances of fluorinated new polymers with the non fluorinated one and with the largely used commercial product. The results obtained demonstrate that the introduction, even in limited amounts, of fluorine atoms in the side ester groups of methacrylic type polymers really improves their protective effect and the durability of the stone treatments. The best results were obtained with the copolymer TFEM/MA which is the fluorinated homologous of Paraloid B72.

Spectrophotometric Determination of Nitrogen Oxides in the Air with 2-N-Ethyl-5-Naphthol-7-Sulfonic Acid

NASA Astrophysics Data System (ADS)

Huang, Y.; Shi, W.; Zhang, C.; Wen, H.

2017-09-01

For the determination of nitrogen oxides in the air, the structure of diazo and coupling compounds was studied and tested by experiments. The conditions and methods of diazo and coupling reactions were investigated. Furthermore, a spectrophotometric method using sulfanilamide as a diazo compound and 2-N-ethyl-5-naphthol-7-sulfonic acid (N-ethyl J acid) as a coupling compound was proposed. The maximum absorption wavelength of sulfanilamide-Nethyl J acid azo compound was at 478 nm. The molar absorptivity was 4.31 × 104 L/(mol × cm) with a recovery of 98.7-100.9% and RSD of 1.85%. For nitrogen oxides, the determinate limit of this measurement was 0.015 mg/m3 and the determinate range 0.024-2.0 mg/m3. Moreover, a high degree of correlation was observed between the results obtained by the proposed method and the standard methods. The proposed method can be easily applied to determine nitrogen oxides in the air.

Cytostatic action of two nitrosoureas derived from cysteamine.

PubMed Central

Bourut, C.; Chenu, E.; Godenèche, D.; Madelmont, J. C.; Maral, R.; Mathé, G.; Meyniel, G.

1986-01-01

2-Chloroethyl nitrosocarbamoylcystamine or ICIG-1325 (CNCC) is a lipid-soluble isomeric mixture of nitrosoureas. Its dose-effect relationship on L1210 leukaemia is characterized by a large maximally efficient dose-range (MEDR), greater than that of other nitrosoureas. CNCC also demonstrated significant therapeutic activity on intracerebrally (i.c.) transplanted L1210 leukaemia and on six transplanted solid tumours, TM2 mammary carcinoma, M555 ovarian carcinoma, B16 melanoma, glioma 26, 3LL, Lewis lung carcinoma and colon 26 carcinoma. It was inactive on fibrosarcoma ICIG-Ci4. Its antitumour activity spectrum is wider than that of the related compounds 2-[3-(2-chloroethyl) 3-nitrosoureido]D-glucopyranose (CZT), (chloro-2-ethyl)-1(ribofuranosyl-isopropylidene-2'-3' paranitrobenzoate-5')-3 nitrosourea (RFCNU), and (chloro-2-ethyl)-1 (ribopyranosyl triacetate-2'-3'-4')-3 nitrosourea (RPCNU). A study of its metabolic disposition in animals has shown that CNCC undergoes extensive first-pass metabolism leading to the formation of four main plasma metabolites. These metabolites are water-soluble nitrosoureas that arose from the bioreduction of the disulphide bridge followed by the methylation and the oxidation of the thiol groups. Experimental screening was performed with these chemically synthesized metabolites. Both N'-(2-chloroethyl)-N-[2-(methylsulphinyl)ethyl]-N'-nitrosourea (CMSOEN2) and N'-(2-chloroethyl)-N-[2-(methylsulphonyl)ethyl]-N'-nitrosourea (CMSO2EN2) are very active on L1210 leukaemia grafted intraperitoneally (i.p.) and i.c., L40 leukaemia, B16 melanoma, glioma 26 and Lewis lung carcinoma. Their effectiveness is better than that of the parent compound CNCC. In addition,the percentage of mice cured after CMSOEN2 or CMSO2EN2 treatment is increased especially on B16 melanoma and glioma 26.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:3801787

Ruthenium(II) arene complexes with chelating chloroquine analogue ligands: Synthesis, characterization and in vitro antimalarial activity†

PubMed Central

Glans, Lotta; Ehnbom, Andreas; de Kock, Carmen; Martínez, Alberto; Estrada, Jesús; Smith, Peter J.; Haukka, Matti; Sánchez-Delgado, Roberto A.; Nordlander, Ebbe

2012-01-01

Three new ruthenium complexes with bidentate chloroquine analogue ligands, [Ru(η6-cym)(L1)Cl]Cl (1, cym = p-cymene, L1 = N-(2-((pyridin-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine), [Ru(η6-cym)(L2)Cl]Cl (2, L2 = N-(2-((1-methyl-1H-imidazol-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine) and [Ru(η6-cym)(L3)Cl] (3, L3 = N-(2-((2-hydroxyphenyl)methylimino)ethyl)-7-chloroquinolin-4-amine) have been synthesized and characterized. In addition, the X-ray crystal structure of 2 is reported. The antimalarial activity of complexes 1–3 and ligands L1, L2 and L3, as well as the compound N-(2-(bis((pyridin-2-yl)methyl)amino)ethyl)-7-chloroquinolin-4-amine (L4), against chloroquine sensitive and chloroquine resistant Plasmodium falciparum malaria strains was evaluated. While 1 and 2 are less active than the corresponding ligands, 3 exhibits high antimalarial activity. The chloroquine analogue L2 also shows good activity against both the choloroquine sensitive and the chloroquine resistant strains. Heme aggregation inhibition activity (HAIA) at an aqueous buffer/n-octanol interface (HAIR50) and lipophilicity (D, as measured by water/n-octanol distribution coefficients) have been measured for all ligands and metal complexes. A direct correlation between the D and HAIR50 properties cannot be made because of the relative structural diversity of the complexes, but it may be noted that these properties are enhanced upon complexation of the inactive ligand L3 to ruthenium, to give a metal complex (3) with promising antimalarial activity. PMID:22249579

Effect of total hydroalcholic extract of Nigella sativa and its n-hexane and ethyl acetate fractions on ACHN and GP-293 cell lines.

PubMed

Shahraki, Samira; Khajavirad, Abolfazl; Shafei, Mohammad Naser; Mahmoudi, Mahmoud; Tabasi, Nafisa Sadat

2016-01-01

Medicinal plants are noted for their many advantages including the ability to treat diseases such as cancer. In this study, we examined the antitumor effect of the medicinal plant Nigella sativa on the morphology, survival, and apoptosis of ACHN (human renal adenocarcinoma) and GP-293 (normal renal epithelial) cell lines. From a hydroalcoholic extract of N. sativa, n-hexane and ethyl acetate fractions were extracted. Cells were treated with various concentrations of total hydroalcholic extract and n-hexane and ethyl acetate fractions; cell viability, morphological changes, and apoptosis were then determined. Results were presented as mean ± standard error of the mean (SEM). One-way analysis of variance (ANOVA) was applied for the statistical analysis of the data. The total extract and the fractions in a dose- and time-dependent manner reduced the cell viability in ACHN with no effect on the GP-293 cell line. In addition, the total extract resulted in more morphological changes in the ACHN cells compared to the GP-293 cells. The effect of the total extract in inducing apoptosis after 48 hours in the ACHN cell line was greater than in GP-293. In addition, the effect of the two fractions was lower than the total extract at all used concentrations. Therefore, the effect of total extract and n-hexane and ethyl acetate fractions of N. sativa on cell viability and apoptosis in the ACHN cell line is greater than in the GP-293 cell line. However, the effect of the total extract is higher than either of the two fractions on their own.

40 CFR Table 2 to Subpart Ggg of... - Partially Soluble HAP

Code of Federal Regulations, 2012 CFR

2012-07-01

... Trichloroethylene Chloroethane (ethyl chloride) Trimethylpentane Vinyl acetate Xylene (p) Vinyl chloride N-hexane... Methylene chloride Allyl chloride N,N-dimethylaniline Benzene Propionaldehyde Benzyl chloride Propylene...

40 CFR Table 2 to Subpart Ggg of... - Partially Soluble HAP

Code of Federal Regulations, 2011 CFR

2011-07-01

... Trichloroethylene Chloroethane (ethyl chloride) Trimethylpentane Vinyl acetate Xylene (p) Vinyl chloride N-hexane... Methylene chloride Allyl chloride N,N-dimethylaniline Benzene Propionaldehyde Benzyl chloride Propylene...

40 CFR Table 2 to Subpart Ggg of... - Partially Soluble HAP

Code of Federal Regulations, 2010 CFR

2010-07-01

... Trichloroethylene Chloroethane (ethyl chloride) Trimethylpentane Vinyl acetate Xylene (p) Vinyl chloride N-hexane... Methylene chloride Allyl chloride N,N-dimethylaniline Benzene Propionaldehyde Benzyl chloride Propylene...

N-(3-Chloro-1-methyl-1H-indazol-5-yl)-4-methylbenzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Amiri, Ouafa; Saadi, Mohamed; El Ammari, Lahcen

2014-01-01

The asymmetric unit of the title compound, C15H14ClN3O2S, contains two independent mol­ecules showing different conformations: in one mol­ecule, the indazole ring system makes a dihedral angle of 51.5 (1)° with the benzene ring whereas in the other, the indazole unit is almost perpendicular to the benzene ring [dihedral angle 77.7 (1)°]. In the crystal, the mol­ecules are linked by N—H⋯N and N—H⋯O hydrogen bonds, forming a set of four mol­ecules linked in pairs about an inversion centre. PMID:24764895

N-(3-Chloro-4-eth-oxy-1-methyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Hannioui, Abdellah; Saadi, Mohamed; El Ammari, Lahcen

2014-06-01

The indazole ring system of the title compound, C17H18ClN3O4S, is almost planar (r.m.s. deviation = 0.0113 Å) and forms dihedral angles of 32.22 (8) and 57.5 (3)° with the benzene ring and the mean plane through the 4-eth-oxy group, respectively. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into inversion dimers, which are further linked by π-π inter-actions between the diazole rings [inter-centroid distance = 3.4946 (11) Å], forming chains parallel to [101].

Liquid chromatography-tandem mass spectrometry analysis of perfluorooctane sulfonate and perfluorooctanoic Acid in fish fillet samples.

PubMed

Paiano, Viviana; Fattore, Elena; Carrà, Andrea; Generoso, Caterina; Fanelli, Roberto; Bagnati, Renzo

2012-01-01

Perfluorooctane sulfonate (PFOS) and perfluorooctanoic (PFOA) acid are persistent contaminants which can be found in environmental and biological samples. A new and fast analytical method is described here for the analysis of these compounds in the edible part of fish samples. The method uses a simple liquid extraction by sonication, followed by a direct determination using liquid chromatography-tandem mass spectrometry (LC-MS/MS). The linearity of the instrumental response was good, with average regression coefficients of 0.9971 and 0.9979 for PFOS and PFOA, respectively, and the coefficients of variation (CV) of the method ranged from 8% to 20%. Limits of detection (LOD) were 0.04 ng/g for both the analytes and recoveries were 90% for PFOS and 76% for PFOA. The method was applied to samples of homogenized fillets of wild and farmed fish from the Mediterranean Sea. Most of the samples showed little or no contamination by perfluorooctane sulfonate and perfluorooctanoic acid, and the highest concentrations detected among the fish species analyzed were, respectively, 5.96 ng/g and 1.89 ng/g. The developed analytical methodology can be used as a tool to monitor and to assess human exposure to perfluorinated compounds through sea food consumption.

Quantification of four major metabolites of embryotoxic N-methyl- and N-ethyl-2-pyrrolidone in human urine by cooled-injection gas chromatography and isotope dilution mass spectrometry.

PubMed

Schindler, Birgit K; Koslitz, Stephan; Meier, Swetlana; Belov, Vladimir N; Koch, Holger M; Weiss, Tobias; Brüning, Thomas; Käfferlein, Heiko U

2012-04-17

N-Methyl- and N-ethyl-2-pyrollidone (NMP and NEP) are frequently used industrial solvents and were shown to be embryotoxic in animal experiments. We developed a sensitive, specific, and robust analytical method based on cooled-injection (CIS) gas chromatography and isotope dilution mass spectrometry to analyze 5-hydroxy-N-ethyl-2-pyrrolidone (5-HNEP) and 2-hydroxy-N-ethylsuccinimide (2-HESI), two newly identified presumed metabolites of NEP, and their corresponding methyl counterparts (5-HNMP, 2-HMSI) in human urine. The urine was spiked with deuterium-labeled analogues of these metabolites. The analytes were separated from urinary matrix by solid-phase extraction and silylated prior to quantification. Validation of this method was carried out by using both, spiked pooled urine samples and urine samples from 56 individuals of the general population with no known occupational exposure to NMP and NEP. Interday and intraday imprecision was better than 8% for all metabolites, while the limits of detection were between 5 and 20 μg/L depending on the analyte. The high sensitivity of the method enables us to quantify NMP and NEP metabolites at current environmental exposures by human biomonitoring.

Multiresidue Method for Quantification of Sulfonamides and Trimethoprim in Tilapia Fillet by Liquid Chromatography Coupled to Quadrupole Time-of-Flight Mass Spectrometry Using QuEChERS for Sample Preparation.

PubMed

Nunes, Kátia S D; Assalin, Márcia R; Vallim, José H; Jonsson, Claudio M; Queiroz, Sonia C N; Reyes, Felix G R

2018-01-01

A multiresidue method for detecting and quantifying sulfonamides (sulfapyridine, sulfamerazine, sulfathiazole, sulfamethazine, sulfadimethoxine, sulfamethoxazole, and sulfamethoxypyridazine) and trimethoprim in tilapia fillet ( Oreochromis niloticus ) using liquid chromatography coupled to mass spectrometry was developed and validated. The sample preparation was optimized using the QuEChERS approach. The chromatographic separation was performed using a C18 column and 0.1% formic acid in water and acetonitrile as the mobile phase in the isocratic elution mode. Method validation was performed based on the Commission Decision 2002/657/EC and Brazilian guideline. The validation parameters evaluated were linearity ( r  ≥ 0.99); limits of detection (LOD) and quantification (LOQ), 1 ng·g -1 and 5 ng·g -1 , respectively; intraday and interdays precision (CV lower than 19.4%). The decision limit (CC α 102.6-120.0 ng·g -1 and 70 ng·g -1 for sulfonamides and trimethoprim, respectively) and detection capability (CC β 111.7-140.1 ng·g -1 and 89.9 ng·g -1 for sulfonamides and trimethoprim, respectively) were determined. Analyses of tilapia fillet samples from fish exposed to sulfamethazine through feed (incurred samples) were conducted in order to evaluate the method. This new method was demonstrated to be fast, sensitive, and suitable for monitoring sulfonamides and trimethoprim in tilapia fillet in health surveillance programs, as well as to be used in pharmacokinetics and residue depletion studies.

Multiresidue Method for Quantification of Sulfonamides and Trimethoprim in Tilapia Fillet by Liquid Chromatography Coupled to Quadrupole Time-of-Flight Mass Spectrometry Using QuEChERS for Sample Preparation

PubMed Central

Nunes, Kátia S. D.; Assalin, Márcia R.; Vallim, José H.; Jonsson, Claudio M.; Queiroz, Sonia C. N.

2018-01-01

A multiresidue method for detecting and quantifying sulfonamides (sulfapyridine, sulfamerazine, sulfathiazole, sulfamethazine, sulfadimethoxine, sulfamethoxazole, and sulfamethoxypyridazine) and trimethoprim in tilapia fillet (Oreochromis niloticus) using liquid chromatography coupled to mass spectrometry was developed and validated. The sample preparation was optimized using the QuEChERS approach. The chromatographic separation was performed using a C18 column and 0.1% formic acid in water and acetonitrile as the mobile phase in the isocratic elution mode. Method validation was performed based on the Commission Decision 2002/657/EC and Brazilian guideline. The validation parameters evaluated were linearity (r ≥ 0.99); limits of detection (LOD) and quantification (LOQ), 1 ng·g−1 and 5 ng·g−1, respectively; intraday and interdays precision (CV lower than 19.4%). The decision limit (CCα 102.6–120.0 ng·g−1 and 70 ng·g−1 for sulfonamides and trimethoprim, respectively) and detection capability (CCβ 111.7–140.1 ng·g−1 and 89.9 ng·g−1 for sulfonamides and trimethoprim, respectively) were determined. Analyses of tilapia fillet samples from fish exposed to sulfamethazine through feed (incurred samples) were conducted in order to evaluate the method. This new method was demonstrated to be fast, sensitive, and suitable for monitoring sulfonamides and trimethoprim in tilapia fillet in health surveillance programs, as well as to be used in pharmacokinetics and residue depletion studies. PMID:29686929

Development and validation of a liquid chromatography-UV detection method for the determination of sulfonamides in fish muscle and shrimp according to European Union Decision 2002/657/EC.

PubMed

Granja, Rodrigo H M M; De Lima, Andreia C; Salerno, Alessandro G; Wanschel, Amarylis C B A

2013-01-01

Sulfonamides are one class of antimicrobial agents used in aquaculture production. Sulfonamides are often overused because they are inexpensive and readily available. Their presence at a concentration above the legal limits is a potential hazard to human health. Brazilian authorities have included in the National Regulatory Monitoring Program the control of the three most widely used sulfonamides in aquaculture production, i.e., sulfathiazole, sulfamethazine, and sulfadimethoxine. An LC method with UV detection for the determination of residual sulfonamides in fish muscle, using sulfapyridine as an internal standard has been developed and validated. The validation was performed according to the Brazilian Regulation 24/2009 (equivalent to European Union Decision 2002/657/EC). The method meets the Brazilian regulatory requirement that establishes criteria and procedures for determination of parameters such as decision limit (CCalpha), detection capability (CCbeta), precision, and recovery. For fish muscle, CCalpha was determined at 3.63, 2.91, and 7.46 microg/kg for sulfathiazole, sulfamethazine, and sulfadimethoxine, respectively. CCbeta was 9.39, 14.54, and 9.39 microg/kg for sulfathiazole, sulfamethazine, and sulfadimethoxine, respectively. For shrimp, CCalpha was 11.5, 8.67, and 4.46 microg/kg for sulfathiazole, sulfamethazine, and sulfadimethoxine, respectively. CCbeta was 18, 11.93, and 5.24 microg/kg for sulfathiazole, sulfamethazine, and sulfadimethoxine, respectively. A complete statistical analysis was performed on the results obtained. The results indicate that the method is robust when subjected to day-to-day analytical variations.

Discovery of N-[4-(1H-Pyrazolo[3,4-b]pyrazin-6-yl)-phenyl]-sulfonamides as Highly Active and Selective SGK1 Inhibitors

PubMed Central

2014-01-01

From a virtual screening starting point, inhibitors of the serum and glucocorticoid regulated kinase 1 were developed through a combination of classical medicinal chemistry and library approaches. This resulted in highly active small molecules with nanomolar activity and a good overall in vitro and ADME profile. Furthermore, the compounds exhibited unusually high kinase and off-target selectivity due to their rigid structure. PMID:25589934

Discovery of N-[4-(1H-Pyrazolo[3,4-b]pyrazin-6-yl)-phenyl]-sulfonamides as Highly Active and Selective SGK1 Inhibitors.

PubMed

Halland, Nis; Schmidt, Friedemann; Weiss, Tilo; Saas, Joachim; Li, Ziyu; Czech, Jörg; Dreyer, Matthias; Hofmeister, Armin; Mertsch, Katharina; Dietz, Uwe; Strübing, Carsten; Nazare, Marc

2015-01-08

From a virtual screening starting point, inhibitors of the serum and glucocorticoid regulated kinase 1 were developed through a combination of classical medicinal chemistry and library approaches. This resulted in highly active small molecules with nanomolar activity and a good overall in vitro and ADME profile. Furthermore, the compounds exhibited unusually high kinase and off-target selectivity due to their rigid structure.

An Efficient Amide-Aldehyde-Alkene Condensation: Synthesis for the N-Allyl Amides.

PubMed

Quan, Zheng-Jun; Wang, Xi-Cun

2016-02-01

The allylamine skeleton represents a significant class of biologically active nitrogen compounds that are found in various natural products and drugs with well-recognized pharmacological properties. In this personal account, we will briefly discuss the synthesis of allylamine skeletons. We will focus on showing a general protocol for Lewis acid-catalyzed N-allylation of electron-poor N-heterocyclic amides and sulfonamide via an amide-aldehyde-alkene condensation reaction. The substrate scope with respect to N-heterocyclic amides, aldehydes, and alkenes will be discussed. This method is also capable of preparing the Naftifine motif from N-methyl-1-naphthamide or methyl (naphthalene-1-ylmethyl)carbamate, with paraformaldehyde and styrene in a one-pot manner. © 2016 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Fluorescence Spectrometric Determination of Drugs Containing α-Methylene Sulfone/Sulfonamide Functional Groups Using N-Methylnicotinamide Chloride as a Fluorogenic Agent.

PubMed

Elokely, Khaled M; Eldawy, Mohamed A; Elkersh, Mohamed A; El-Moselhy, Tarek F

2011-01-01

A simple spectrofluorometric method has been developed, adapted, and validated for the quantitative estimation of drugs containing α-methylene sulfone/sulfonamide functional groups using N(1)-methylnicotinamide chloride (NMNCl) as fluorogenic agent. The proposed method has been applied successfully to the determination of methyl sulfonyl methane (MSM) (1), tinidazole (2), rofecoxib (3), and nimesulide (4) in pure forms, laboratory-prepared mixtures, pharmaceutical dosage forms, spiked human plasma samples, and in volunteer's blood. The method showed linearity over concentration ranging from 1 to 150 μg/mL, 10 to 1000 ng/mL, 1 to 1800 ng/mL, and 30 to 2100 ng/mL for standard solutions of 1, 2, 3, and 4, respectively, and over concentration ranging from 5 to 150 μg/mL, 10 to 1000 ng/mL, 10 to 1700 ng/mL, and 30 to 2350 ng/mL in spiked human plasma samples of 1, 2, 3, and 4, respectively. The method showed good accuracy, specificity, and precision in both laboratory-prepared mixtures and in spiked human plasma samples. The proposed method is simple, does not need sophisticated instruments, and is suitable for quality control application, bioavailability, and bioequivalency studies. Besides, its detection limits are comparable to other sophisticated chromatographic methods.

1-(2-Cyano­ethyl)-2-(2-pyrid­yl)-1H,3H-benzimidazol-3-ium perchlorate

PubMed Central

Li, Yan; Tang, Xiaoliang; Chen, Jiayu; Wu, Daxiang; Liu, Weisheng

2010-01-01

The title compound, C15H13N4 +·ClO4 −, comprises a nonplanar 1-(2-cyano­ethyl)-2-(2-pyrid­yl)-1H,3H-benzimidazol-3-ium cation [dihedral angle between the imidazole and pyridine rings = 22.5 (8)°] and a perchlorate anion. The cation is formed by protonation of the N atom of the benzimidazole ring. A charged N—H⋯O hydrogen bond connects the anion and cation, and inter­molecular C—H⋯O and C—H⋯N inter­actions contribute to the crystal packing. PMID:21579831

Development of an UPLC-MS/MS Sulfonamide Multi-residue Method and its Application to Water, Manure Slurry, and Soils from Swine Rearing Facilities

USDA-ARS?s Scientific Manuscript database

An analytical method was developed using ultra performance liquid chromatography-triple quadrupole-tandem mass spectrometry (UPLC-TQ-MS/MS) to simultaneously analyze 14 sulfonamides (SA) in six minutes. Despite the rapidity of the assay the system was properly re-equilibrated in this time. No carryo...

Mixture toxicity of six sulfonamides and their two transformation products to green algae Scenedesmus vacuolatus and duckweed Lemna minor.

PubMed

Białk-Bielińska, Anna; Caban, Magda; Pieczyńska, Aleksandra; Stepnowski, Piotr; Stolte, Stefan

2017-04-01

Since humans and ecosystems are continually exposed to a very complex and permanently changing mixture of chemicals, there is increasing concern in the general public about the potential adverse effects they may cause. Among all "emerging pollutants", pharmaceuticals in particular have raised great environmental concern. For these reasons the aim of our study was to evaluate the mixture toxicity of six antimicrobial sulfonamides (SAs) and their two most commonly identified degradation products - sulfanilic acid (SNA) and sulfanilamide (SN) - to limnic green algae Scenedesmus vacuolatus and duckweed Lemna minor. The ecotoxicological data for the single toxicity of SNA and SN towards selected organisms are presented. The concept of Concentration Addition (CA) was applied to estimate the effects, and less than additive effects were observed. In general terms, it seems sufficiently precautionary for the aquatic environment to consider the toxicity of a sulfonamide mixture as additive. The Concentration Addition model proves to be a reasonable worst-case estimation. Such a comparative study on the mixture toxicity of sulfonamides and their transformation products has been presented for the first time. Copyright © 2017 Elsevier Ltd. All rights reserved.

Development of an immunoaffinity column method using broad-specificity monoclonal antibodies for simultaneous extraction and cleanup of quinolone and sulfonamide antibiotics in animal muscle tissues.

PubMed

Li, Cun; Wang, Zhanhui; Cao, Xingyuan; Beier, Ross C; Zhang, Suxia; Ding, Shuangyang; Li, Xiaowei; Shen, Jianzhong

2008-10-31

This paper describes a novel mixed-bed immunoaffinity column (IAC) method. The IAC was produced by coupling anti-quinolone and anti-sulfonamide broad-specificity monoclonal antibodies to Sepharose 4B for simultaneously isolating 13 quinolones (QNs) and 6 sulfonamides (SAs) from swine and chicken muscle tissues, followed by antibiotic determination using liquid chromatography-tandem mass spectrometry (LC-MS/MS). A new broad-specificity Mab (B1A4E8) toward sulfonamides was produced using sulfamethoxazole as hapten that demonstrated cross-reactivities to 6 SAs in the range of 31-112%. IAC optimized conditions were found that allowed the IAC to be reused for selective binding of both SAs and QNs. Recoveries of all 19 antibiotics from animal muscle ranged from 72.6 to 107.6%, with RSDs below 11.3% and 15.4% for intra-day and inter-day experiments, respectively. The limit of quantification ranged from 0.5 to 3.0ng/g. The strategy used here for a mixed-bed IAC may be used to study other compounds and more than two classes of analytes simultaneously.

Laser desorption single-conformation UV and IR spectroscopy of the sulfonamide drug sulfanilamide, the sulfanilamide-water complex, and the sulfanilamide dimer.

PubMed

Uhlemann, Thomas; Seidel, Sebastian; Müller, Christian W

2017-06-07

We have studied the conformational preferences of the sulfonamide drug sulfanilamide, its dimer, and its monohydrated complex through laser desorption single-conformation UV and IR spectroscopy in a molecular beam. Based on potential energy curves for the inversion of the anilinic and the sulfonamide NH 2 groups calculated at DFT level, we suggest that the zero-point level wave function of the sulfanilamide monomer is appreciably delocalized over all four conformer wells. The sulfanilamide dimer, and the monohydrated complex each exhibit a single isomer in the molecular beam. The isomeric structures of the sulfanilamide dimer and the monohydrated sulfanilamide complex were assigned based on their conformer-specific IR spectra in the NH and OH stretch region. Quantum Theory of Atoms in Molecules (QTAIM) analysis of the calculated electron density in the water complex suggests that the water molecule is bound side-on in a hydrogen bonding pocket, donating one O-HO[double bond, length as m-dash]S hydrogen bond and accepting two hydrogen bonds, a NHO and a CHO hydrogen bond. QTAIM analysis of the dimer electron density suggests that the C i symmetry dimer structure exhibits two dominating N-HO[double bond, length as m-dash]S hydrogen bonds, and three weaker types of interactions: two CHO bonds, two CHN bonds, and a chalcogen OO interaction. Most interestingly, the molecular beam dimer structure closely resembles the R dimer unit - the dimer unit with the greatest interaction energy - of the α, γ, and δ crystal polymorphs. Interacting Quantum Atoms analysis provides evidence that the total intermolecular interaction in the dimer is dominated by the short-range exchange-correlation contribution.

Genotoxic, Cytotoxic, Antigenotoxic, and Anticytotoxic Effects of Sulfonamide Chalcone Using the Ames Test and the Mouse Bone Marrow Micronucleus Test

PubMed Central

Borges, Flávio Fernandes Veloso; Bernardes, Aline; Perez, Caridad Noda; Silva, Daniela de Melo e

2015-01-01

Chalcones present several biological activities and sulfonamide chalcone derivatives have shown important biological applications, including antitumor activity. In this study, genotoxic, cytotoxic, antigenotoxic, and anticytotoxic activities of the sulfonamide chalcone N-{4-[3-(4-nitrophenyl)prop-2-enoyl]phenyl} benzenesulfonamide (CPN) were assessed using the Salmonella typhimurium reverse mutation test (Ames test) and the mouse bone marrow micronucleus test. The results showed that CPN caused a small increase in the number of histidine revertant colonies in S. typhimurium strains TA98 and TA100, but not statistically significant (p > 0.05). The antimutagenicity test showed that CPN significantly decreased the number of His+ revertants in strain TA98 at all doses tested (p < 0.05), whereas in strain TA100 this occurred only at doses higher than 50 μg/plate (p < 0.05). The results of the micronucleus test indicated that CPN significantly increased the frequency of micronucleated polychromatic erythrocytes (MNPCE) at 24 h and 48 h, revealing a genotoxic effect of this compound. Also, a significant decrease in polychromatic/normochromatic erythrocyte ratio (PCE/NCE) was observed at the higher doses of CPN at 24 h and 48 h (p < 0.05), indicating its cytotoxic action. CPN co-administered with mitomycin C (MMC) significantly decreased the frequency of MNPCE at almost all doses tested at 24 h (p < 0.05), showing its antigenotoxic activity, and also presented a small decrease in MNPCE at 48 h (p > 0.05). Additionally, CPN co-administered with MMC significantly increased PCE/NCE ratio at all doses tested, demonstrating its anticytotoxic effect. In summary, CPN presented genotoxic, cytotoxic, antigenotoxic, and anticytotoxic properties. PMID:26335560

Metabolism of amosulalol hydrochloride in man: quantitative comparison with laboratory animals.

PubMed

Kamimura, H; Sasaki, H; Kawamura, S

1985-05-01

The metabolism of amosulalol hydrochloride, (+/-)-5-[1-hydroxy-2-[[2-(o-methoxyphenoxy)ethyl]amino]ethyl]-2- methylbenzenesulphonamide hydrochloride, was studied in man and laboratory animals. Humans excreted 30.1% of dose as unchanged drug, and the sulphate conjugate of a 5-hydroxy metabolite, (+/-)-5-[1-hydroxy-2-[[2-(5-hydroxy-2-methoxyphenoxy)ethyl]-amino] ethyl]-2-methylbenzenesulphonamide, was the major metabolite. Amosulalol hydrochloride was extensively metabolized in animals with 10% or less excreted as unchanged drug. Hydroxylation of the 2-methyl group and O-demethylation of the o-methoxyphenoxy group were preferred in rats, and oxidative C-N cleavage yielding o-methoxyphenoxyacetic acid (M-5) preceded other reactions in dogs. Monkeys excreted almost equal amounts of the 5-hydroxy and 4-hydroxy metabolites as well as M-5.

Synthesis and Purification of Tunable High Tg Electro-Optical Polymers by Ring Opening Metathesis Polymerization

DTIC Science & Technology

2011-09-01

The amic acid was dissolved in DMF (100 mL) at 100 °C. Acetic anhydride (14.8 g, 0.145 mol) and anhydrous sodium acetate (0.8 g, 0.01 mol) were...exo-N-[(E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethyl benzoate ] nadimide (5). DPTS (0.44 g, 1.41 mmol), exo-N-(p-Carboxyphenyl...agent for a Ru-based catalyst when extracted with aqueous sodium bicarbonate (28, 29). We reasoned that MNA could enhance the solubility of the

Antiviral evaluation of plants from Brazilian Atlantic Tropical Forest.

PubMed

Andrighetti-Fröhner, C R; Sincero, T C M; da Silva, A C; Savi, L A; Gaido, C M; Bettega, J M R; Mancini, M; de Almeida, M T R; Barbosa, R A; Farias, M R; Barardi, C R M; Simões, C M O

2005-06-01

The antiviral activity of six medicinal plants from Brazilian Atlantic Tropical Forest was investigated against two viruses: herpes simplex virus type 1 (HSV-1) and poliovirus type 2 (PV-2). Cuphea carthagenensis and Tillandsia usneoides extracts showed the best antiherpes activity. T. usneoides dichloromethane, ethyl acetate and n-butanol extracts, and Lippia alba n-butanol extract showed inhibition of HSV-1, strain 29R/acyclovir resistant. In addition, only L. alba ethyl acetate extract showed antipoliovirus activity. These results corroborate that medicinal plants can be a rich source of potential antiviral compounds.

Vanillin as a modulator agent in SMART test: inhibition in the steps that precede N-methyl-N-nitrosourea-, N-ethyl-N-nitrosourea-, ethylmethanesulphonate- and bleomycin-genotoxicity.

PubMed

Sinigaglia, Marialva; Lehmann, Maurício; Baumgardt, Paula; do Amaral, Viviane Souza; Dihl, Rafael Rodrigues; Reguly, Maria Luíza; de Andrade, Heloísa Helena Rodrigues

2006-09-05

Vanillin (VA), the world's major flavoring compound used in food industry and confectionery products - that has antimutagenic and anticarcinogenic activity against a variety of mutagenic/carcinogenic agents - was tested for the interval between the formation of premutational lesion and it is finalization as a DNA lesion. The overall findings using co-treatment protocols in SMART test suggest that VA can lead to a significant protection against the general genotoxicity of ethylmethanesulphonate (EMS), N-ethyl-N-nitrosourea (ENU), N-methyl-N-nitrosourea (MNU) and bleomycin sulphate (BLEO). Considering MNU, ENU and EMS the desmutagenic activity observed could result from VA-stimulation of detoxification, via induction of glutathione S-transferase. However, the protector effect related to BLEO could be attributed to its powerful scavenger ability, which has the potential to prevent oxidative damage induced by BLEO.

Occurrence and transport of acetochlor in streams of the Mississippi River Basin

USGS Publications Warehouse

Clark, G.M.; Goolsby, D.A.

1999-01-01

The herbicide acetochlor [2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6- methylphenyl) acetamide] was first used on corn (Zea mays L.) in the USA during the growing season of 1994. By 1996, it was the third most heavily used corn herbicide in the midwestern USA. During the growing season of 1997, 78% of 375 samples collected at 32 stream sites in the Mississippi River Basin contained detectable concentrations of acetochlor. However, concentrations in only 2% of the samples exceeded 2 ??g/L, the maximum annual average concentration allowable in public water supplies derived primarily from surface water. The largest acetochlor concentrations were detected in streams draining basins in parts of Illinois, Indiana, and Iowa. The median concentration of acetochlor in streams was about 10% that of atrazine (6- chloro-N-ethyl-N-isopropyl-1,3,5-triazine-2,4-diamine), about 25% that of metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide], about 50% that of cyanazine [2-[[4-chloro-6-(ethylamino)-1,3,5- triazin-2-yl]amino]-2-methylpropionitrile], and about threefold that of alachlor [2-chloro-2',6'-diethyl-N-(methoxymethyl) acetanilide]. Load estimates indicate that, during the growing season of 1997, agricultural subbasins draining areas of Illinois, Indiana, and Iowa contributed about 37000 kg, or 74%, of the 50 000 kg of acetochlor measured in streams of the Mississippi River Basin.

Preparation of the monomers of gingerols and 6-shogaol by flash high speed counter-current chromatography.

PubMed

Qiao, Qingliang; Du, Qizhen

2011-09-09

The flash high speed counter-current chromatographic (FHSCCC) separation of gingerols and 6-shogaol was performed on a HSCCC instrument equipped with a 1200-ml column (5 mm tubing i.d.) at a flow rate of 25 ml/min. The performance met the FHSCCC feature that the flow rate of mobile phase (ml) is equal to or greater than the square of the diameter of the column tubing (mm). The separation employed the upper phase of stationary phase of the n-hexane-ethyl acetate-methanol-water (3:2:2:3, v/v) as the stationary phase. A stepwise elution was performed by eluting with the lower phase of n-hexane-ethyl acetate-methanol-water (3:2:2:3, v/v) for first 90 min and the lower phase of the n-hexane-ethyl acetate-methanol-water (3:2:6:5, v/v) for the second 90 min. In each separation 5 g of the ethyl acetate extract of rhizomes of ginger was loaded, yielding 1.96 g of 6-gingerol (98.3%), 0.33 g of 8-gingerol (97.8%), 0.64 g of 6-shogaol (98.8%) and 0.57 g of 10-gingerol (98.2%). The separation can be expected to scale up to industrial separation. Copyright © 2010 Elsevier B.V. All rights reserved.

Sorption of perfluoroalkyl substances (PFASs) to an organic soil horizon - Effect of cation composition and pH.

PubMed

Campos Pereira, Hugo; Ullberg, Malin; Kleja, Dan Berggren; Gustafsson, Jon Petter; Ahrens, Lutz

2018-09-01

Accurate prediction of the sorption of perfluoroalkyl substances (PFASs) in soils is essential for environmental risk assessment. We investigated the effect of solution pH and calculated soil organic matter (SOM) net charge on the sorption of 14 PFASs onto an organic soil as a function of pH and added concentrations of Al 3+ , Ca 2+ and Na + . Often, the organic C-normalized partitioning coefficients (K OC ) showed a negative relationship to both pH (Δlog K OC /ΔpH = -0.32 ± 0.11 log units) and the SOM bulk net negative charge (Δlog K OC  = -1.41 ± 0.40 per log unit mol c g -1 ). Moreover, perfluorosulfonic acids (PFSAs) sorbed more strongly than perfluorocarboxylic acids (PFCAs) and the PFAS sorption increased with increasing perfluorocarbon chain length with 0.60 and 0.83 log K OC units per CF 2 moiety for C 3 -C 10 PFCAs and C 4 , C 6 , and C 8 PFSAs, respectively. The effects of cation treatment and SOM bulk net charge were evident for many PFASs with low to moderate sorption (C 5 -C 8 PFCAs and C 6 PFSA). However for the most strongly sorbing and most long-chained PFASs (C 9 -C 11 and C 13 PFCAs, C 8 PFSA and perfluorooctane sulfonamide (FOSA)), smaller effects of cations were seen, and instead sorption was more strongly related to the pH value. This suggests that the most long-chained PFASs, similar to other hydrophobic organic compounds, are preferentially sorbed to the highly condensed domains of the humin fraction, while shorter-chained PFASs are bound to a larger extent to humic and fulvic acid, where cation effects are significant. Copyright © 2018 The Authors. Published by Elsevier Ltd.. All rights reserved.

Emission of poly and perfluoroalkyl substances, UV-filters and siloxanes to air from wastewater treatment plants.

PubMed

Shoeib, Mahiba; Schuster, Jasmin; Rauert, Cassandra; Su, Ky; Smyth, Shirley-Anne; Harner, Tom

2016-11-01

The potential of wastewater treatment plants (WWTPs) to act as sources of poly and perfluoroalkyl substances (PFASs), volatile methyl siloxanes (VMSs) and organic UV-filters to the atmosphere was investigated. Target compounds included: PFASs (fluorotelomer alcohols (FTOHs), perfluorooctane sulfonamides/sulfonamidoethanols (FOSAs/FOSEs), perfluroalkyl sulfonic acids (PFSAs) and perfluroalkyl carboxylic acids (PFCAs)), cyclic VMSs (D3 to D6), linear VMSs (L3 to L5) and eight UV-filters. Emissions to air were assessed at eight WWTPs using paired sorbent-impregnated polyurethane foam passive air samplers, deployed during summer 2013 and winter 2014. Samplers were deployed on-site above the active tank and off-site as a reference. Several types of WWTPs were investigated: secondary activated sludge in urban areas (UR-AS), secondary extended aeration in towns (TW-EA) and facultative lagoons in rural areas (RU-LG). The concentrations of target compounds in air were ∼1.7-35 times higher on-site compared to the corresponding off-site location. Highest concentrations in air were observed at UR-AS sites while the lowest were at RU-LG. Higher air concentrations (∼2-9 times) were observed on-site during summer compared to winter, possibly reflecting enhanced volatilization due to higher wastewater temperatures or differences in influent wastewater concentrations. A significant positive correlation was obtained between concentrations in air and WWTP characteristics (influent flow rate and population in the catchment of the WWTP); whereas a weak negative correlation was obtained with hydraulic retention time. Emissions to air were estimated using a simplified dispersion model. Highest emissions to air were seen at the UR-AS locations. Emissions to air (g/year/tank) were highest for VMSs (5000-112,000) followed by UV-filters (16-2000) then ΣPFASs (10-110). Copyright © 2016. Published by Elsevier Ltd.

Elevated levels of short carbon-chain PFCAs in breast milk among Korean women: Current status and potential challenges.

PubMed

Kang, Habyeong; Choi, Kyungho; Lee, Haeng-Shin; Kim, Do-Hee; Park, Na-Youn; Kim, Sunmi; Kho, Younglim

2016-07-01

Breast milks can be contaminated with perfluoroalkyl substances (PFASs). Exposure to PFASs during early stages of life may lead to adverse health effects among breastfed infants. To date, perfluorootanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) have been most frequently measured PFASs in breast milks worldwide. Information on shorter carbon-chain PFASs in breast milk is scarce. In this study, breast milks were sampled from 264 Korean lactating women, and measured for seventeen PFASs, including ten perfluoroalkyl carboxylates (PFCAs), four perfluoroalkyl sulfonates, and three perfluoroalkyl sulfonamides. PFOA and PFOS were detected in 98.5% of the breast milk samples, with median concentrations of 0.072 and 0.050ng/mL, respectively. Perfluoropentanoic acid (PFPeA), perfluorohexanoic acid (PFHxA), and perfluoroheptanoic acid (PFHpA) were detected in higher frequencies, ranging between 67.4% and 81.8%. The concentrations of short carbon-chain PFCAs in breast milk such as PFPeA and PFHxA were the highest ever reported to date, and were comparable to that of PFOS. Concentrations of shorter chain PFCA in breast milk tended to be higher among the women with longer lactation period, while those of PFOA showed the opposite trend, suggesting a possibility that breastfeeding might be an important route of excretion for PFOA among lactating women. Fish consumption and the use of consumer products, e.g., skin care products, cosmetics and non-stick coated cooking utensils, were identified as significant predictors of PFAS concentrations in breast milk. Health risks associated with PFOA and PFOS exposure through breastfeeding were estimated negligible, however, risks of the short carbon-chain PFCAs could not be assessed because of lack of relevant toxicological information. Further efforts for source identification and exposure management measures for shorter chain PFCAs are necessary. Copyright © 2016 Elsevier Inc. All rights reserved.

Antiangiogenic effects and mechanisms of trans-ethyl p-methoxycinnamate from Kaempferia galanga L.

PubMed

He, Zhi-Heng; Yue, Grace Gar-Lee; Lau, Clara Bik-San; Ge, Wei; But, Paul Pui-Hay

2012-11-14

Kaempferia galanga L. (Zingiberaceae) is an aromatic herb and a popular spice used as a condiment in Asian cuisine. The ethanol extract of the dried plant and its successive four subfractions were investigated on zebrafish model by quantitative endogenous alkaline phosphatase assay. Both n-hexane and ethyl acetate fractions had antiangiogenic activity, and two major active components (trans-ethyl p-methoxycinnamate and kaempferol) showed potent antiangiogenic effects on wild-type zebrafish. Because of its much stronger effect and no antiangiogenic activity reported, trans-ethyl p-methoxycinnamate was further investigated for its action mechanism. It dose dependently inhibited vessel formation on both wild- and Tg(fli1a:EGFP)y1-type zebrafish embryos. The semiquantitative reverse transcription polymerase chain reaction assay suggested that trans-ethyl p-methoxycinnamate affects multiple molecular targets related to angiogenesis. In vitro, it specifically inhibited the migration and tube formation of human umbilical vein endothelial cells. In vivo, it could block bFGF-induced vessel formation on Matrigel plug assay.

Potential of mangrove Avicennia rumphiana extract as an antioxidant agent using multilevel extraction

NASA Astrophysics Data System (ADS)

Sulmartiwi, L.; Pujiastuti, D. Y.; Tjahjaningsih, W.; Jariyah

2018-04-01

Avicennia rumphiana is one of abundant mangrove found in Indonesia. Multilevel extraction methods were simultaneously conducted to screen the antioxidant activity from mangrove. The leaves, fruits and barks were consequently extracted using n-hexane, ethyl acetate and ethanol. The presence of phenolic, flavonoids and tannins compounds were characterized by quantitative and qualitative phytochemical assay as well as the antioxidant activity was examined using DPPH-free radical scavenging assay. The phytochemical test revealed that all of the extracts showed positive result. The fruits extract exhibited the highest phenolic, flavonoid and tannin (23.86 mg/g, 13.77 mg/g and 74.63 mg/g), respectively. The extracts were further confirmed for antioxidant using IC50 value and revealed that ethyl acetate extract has antioxidant activity better than n-hexane and ethyl acetate extract. Furthermore, this study indicated that mangrove Avicennia rumphiana could be subsequently explored for other biological activities due to their potential secondary metabolites.

Design and Synthesis of Piperazine Sulfonamide Cores Leading to Highly Potent HIV-1 Protease Inhibitors.

PubMed

Bungard, Christopher J; Williams, Peter D; Schulz, Jurgen; Wiscount, Catherine M; Holloway, M Katharine; Loughran, H Marie; Manikowski, Jesse J; Su, Hua-Poo; Bennett, David J; Chang, Lehua; Chu, Xin-Jie; Crespo, Alejandro; Dwyer, Michael P; Keertikar, Kartik; Morriello, Gregori J; Stamford, Andrew W; Waddell, Sherman T; Zhong, Bin; Hu, Bin; Ji, Tao; Diamond, Tracy L; Bahnck-Teets, Carolyn; Carroll, Steven S; Fay, John F; Min, Xu; Morris, William; Ballard, Jeanine E; Miller, Michael D; McCauley, John A

2017-12-14

Using the HIV-1 protease binding mode of MK-8718 and PL-100 as inspiration, a novel aspartate binding bicyclic piperazine sulfonamide core was designed and synthesized. The resulting HIV-1 protease inhibitor containing this core showed an 60-fold increase in enzyme binding affinity and a 10-fold increase in antiviral activity relative to MK-8718 .

Molecular Basis of Sulfonamide and Trimethoprim Resistance in Fish-Pathogenic Aeromonas Isolates ▿

PubMed Central

Kadlec, Kristina; von Czapiewski, Ellen; Kaspar, Heike; Wallmann, Jürgen; Michael, Geovana Brenner; Steinacker, Ulrike; Schwarz, Stefan

2011-01-01

Sulfonamide-trimethoprim-resistant Aeromonas salmonicida and motile Aeromonas spp. from diseased fish of the GERM-Vet study carried the sul1 gene together with mostly cassette-borne trimethoprim resistance genes, including the novel gene dfrA28. The seven dfrA and dfrB genes identified were located mostly in class 1 integrons which commonly harbored other gene cassettes. PMID:21764945

Synthesis and property of solvatochromic fluorophore based on D-pi-A molecular system: 2-[[3-cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene]malononitrile dye.

PubMed

Son, Young-A; Gwon, Seon-Yeong; Lee, Sue-Yoen; Kim, Sung-Hoon

2010-01-01

2-[[3-Cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene]malononitrile styryl dye was prepared by the condensation of 4-[(2-hydroxy-ethyl)-methyl-amino]-benzaldehyde (donor moiety) with 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (acceptor moiety). The corresponding design, synthesis and solvatochromic characteristics of the intramolecular charge-transfer (ICT) dye chromophore were discussed and determined. Optical properties such as absorption and fluorescence emission spectra were monitored in several solvent media with different polarity. In this determination, the prepared dye chromophore showed positive solvatochromism effect and the resulting solvatochromic characteristics were studied with semiempirical calculations. The energy potentials of this dye chromophore such as HOMO and LUMO values were calculated by computational simulation approaches using Material Studio 4.3. Furthermore, the functions as a molecular switching sensor with pH stimulation of alkali-acid addition were determined in DMSO, which was operated by deprotonation/protonation effects based on intramolecular charge-transfer system. Copyright 2009 Elsevier B.V. All rights reserved.

Icosapent ethyl (eicosapentaenoic acid ethyl ester): Effects on remnant-like particle cholesterol from the MARINE and ANCHOR studies.

PubMed

Ballantyne, Christie M; Bays, Harold E; Philip, Sephy; Doyle, Ralph T; Braeckman, Rene A; Stirtan, William G; Soni, Paresh N; Juliano, Rebecca A

2016-10-01

Remnant-like particle cholesterol (RLP-C) is atherogenic and may increase atherosclerotic cardiovascular disease risk. Icosapent ethyl is a high-purity prescription eicosapentaenoic acid ethyl ester (approved as an adjunct to diet to reduce triglyceride [TG] levels in adult patients with TGs ≥500 mg/dL [≥5.65 mmol/L] at 4 g/day). In the MARINE and ANCHOR studies, icosapent ethyl reduced TG and other atherogenic lipid parameter levels without increasing low-density lipoprotein cholesterol (LDL-C) levels. This exploratory analysis evaluated the effects of icosapent ethyl on calculated and directly measured RLP-C. MARINE (TGs ≥500 and ≤2000 mg/dL [≥5.65 mmol/L and ≤22.6 mmol/L]) and ANCHOR (TGs ≥200 and <500 mg/dL [≥2.26 and <5.65 mmol/L] despite statin-controlled LDL-C) were phase 3, 12-week, double-blind studies that randomized adult patients to icosapent ethyl 4 g/day, 2 g/day, or placebo. This analysis assessed median percent change from baseline to study end in directly measured (immunoseparation assay) RLP-C levels (MARINE, n = 218; ANCHOR, n = 252) and calculated RLP-C levels in the full populations. Icosapent ethyl 4 g/day significantly reduced directly measured RLP-C levels -29.8% (p = 0.004) in MARINE and -25.8% (p = 0.0001) in ANCHOR versus placebo, and also reduced directly measured RLP-C levels to a greater extent in subgroups with higher versus lower baseline TG levels, in patients receiving statins versus no statins (MARINE), and in patients receiving medium/higher-intensity versus lower-intensity statins (ANCHOR). Strong correlations were found between calculated and directly measured RLP-C for baseline, end-of-treatment, and percent change values in ANCHOR and MARINE (0.73-0.92; p < 0.0001 for all). Icosapent ethyl 4 g/day significantly reduced calculated and directly measured RLP-C levels versus placebo in patients with elevated TG levels from the MARINE and ANCHOR studies. Copyright © 2016 The Authors. Published by Elsevier Ireland Ltd.. All rights reserved.

Canine superficial bacterial folliculitis: current understanding of its etiology, diagnosis and treatment.

PubMed

Bloom, Paul

2014-02-01

Superficial bacterial folliculitis (SBF) is more common in the dog than other mammalian species. Until recently, a successful outcome in cases of canine SBF was possible by administering a potentiated amoxicillin, a first generation cephalosporin or a potentiated sulfonamide. Unfortunately, this predictable susceptibility has changed, because methicillin resistant Staphylococcus pseudintermedius (MRSP) and Staphylococcus aureus (MRSA) are becoming more prevalent in canine SBF cases. The increasing frequency of multidrug resistance complicates the selection of antimicrobial therapy. Antimicrobial agents that were once rarely used in cases of canine SBF, such as amikacin, rifampicin and chloramphenicol, are becoming the drugs of choice, based on bacterial culture and susceptibility testing. Furthermore, changes in antimicrobial susceptibility have helped to re-emphasize the importance of a multimodal approach to treatment of the disease, including topical therapy. Due to the increasing frequency of identification of highly resistant Staphylococcus spp., topical antimicrobial therapy, including the use of diluted sodium hypochlorite (bleach), is becoming necessary to successfully treat some cases of canine SBF. Other important antiseptics that can be used include chlorhexidine, benzoyl peroxide, ethyl lactate, triclosan and boric acid/acetic acid. This review discusses the diagnostic and therapeutic management of canine SBF, with a special emphasis on treating methicillin resistant staphylococcal infections. Copyright © 2013 Elsevier Ltd. All rights reserved.

Efficient SO2 capture by amine functionalized PEG.

PubMed

Yang, Dezhong; Hou, Minqiang; Ning, Hui; Zhang, Jianling; Ma, Jun; Han, Buxing

2013-11-07

Polyethylene glycols (PEGs) are a class of non-toxic, non-volatile, biocompatible, and widely available polymers. In this work, we synthesized N-ethyl-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2-aminoethanol (EE3AE) that combines the properties of PEG and amines, and N-decyl-N-ethyl-2-aminoethanol (DEAE). Their performances to capture SO2 were studied at different temperatures, pressures, and absorption times. The interaction between the absorbents and SO2 were characterized by NMR and FTIR techniques. It was demonstrated that both EE3AE and DEAE could absorb SO2 efficiently, and there existed chemical and physical interactions between the absorbents and SO2. In particular, the absorption capacity of EE3AE could be as high as 1.09 g SO2 per g EE3AE at 1 atm. The absorption capacity of EE3AE was much larger than that of DEAE because the ether group in the EE3AE interacted with SO2 more strongly than the alkyl group in the DEAE. The SO2 absorbed by EE3AE could be stripped out by bubbling N2 or by applying a vacuum and the EE3AE could be reused. Moreover, both absorbents exhibited a high SO2-CO2 selectivity.

Review of Vaccinia Virus and Baculovirus Viability Versus Virucides

DTIC Science & Technology

2008-03-01

21 disinfectant. Sugimoto and Toyoshima (1979) reported on the inactivation of VACV by Na-Cocoyi-L-Arginine Ethyl Ester, DL- Pyroglutamic Acid Salt...12, pp 473-475. Sugimoto, Y.; Toyoshima, S. N"-Cocoyi-L-Arginine Ethyl Ester, DL- Pyroglutamic Acid Salt, as an Inactivator of Hepatitis B Surface...20 5.1.3 Ascorbic Acid ....................................................................... 20 5.1.4 Dithiothreitol Reducing Agent

Synthesis and serotonergic activity of substituted 2, N-benzylcarboxamido-5-(2-ethyl-1-dioxoimidazolidinyl)-N, N-dimethyltryptamine derivatives: novel antagonists for the vascular 5-HT(1B)-like receptor.

PubMed

Moloney, G P; Martin, G R; Mathews, N; Milne, A; Hobbs, H; Dodsworth, S; Sang, P Y; Knight, C; Williams, M; Maxwell, M; Glen, R C

1999-07-15

The synthesis and vascular 5-HT(1B)-like receptor activity of a novel series of substituted 2, N-benzylcarboxamido-5-(2-ethyl-1-dioxoimidazolidinyl)-N, N-dimethyltryptamine derivatives are described. Modifications to the 5-ethylene-linked heterocycle and to substituents on the 2-benzylamide side chain have been explored. Several compounds were identified which exhibited affinity at the vascular 5-HT(1B)-like receptor of pK(B) > 7.0, up to 100-fold selectivity over alpha(1)-adrenoceptor affinity and 5-HT(2A) receptor affinity, and which exhibited a favorable pharmacokinetic profile. N-Benzyl-3-[2-(dimethylamino)ethyl]-5-[2-(4,4-dimethyl-2, 5-dioxo-1-imidazolidinyl)ethyl]-1H-indole-2-carboxamide (23) was identified as a highly potent, silent (as judged by the inability of angiotensin II to unmask 5-HT(1B)-like receptor-mediated agonist activity in the rabbit femoral artery), and competitive vascular 5-HT(1B)-like receptor antagonist with a plasma elimination half-life of approximately 4 h in dog plasma and with good oral bioavailability. The selectivity of compounds from this series for the vascular 5-HT(1B)-like receptors over other receptor subtypes is discussed as well as a proposed mode of binding to the receptor pharmacophore. It has been proposed that the aromatic ring of the 2, N-benzylcarboxamide group can occupy an aromatic binding site rather than the indole ring. The resulting conformation allows an amine-binding site to be occupied by the ethylamine nitrogen and a hydrogen-bonding site to be occupied by one of the hydantoin carbonyls. The electronic nature of the 2,N-benzylcarboxamide aromatic group as well as the size of substituents on this aromatic group is crucial for producing potent and selective antagonists. The structural requirement on the 3-ethylamine side chain incorporating the protonatable nitrogen is achieved by the bulky 2, N-benzylcarboxamide group and its close proximity to the 3-side chain.

Novel 4-(4-substituted-thiazol-2-ylamino)-N-(pyridin-2-yl)-benzenesulfonamides as cytotoxic and radiosensitizing agents.

PubMed

Ghorab, Mostafa M; Ragab, Fatma A; Heiba, Helmy I; Agha, Hebaallah M; Nissan, Yassin M

2012-01-01

A series of novel 4-(4-substituted-thiazol-2-ylamino)-N-(pyridin-2-yl) benzene-sulfonamides were synthesized and screened for their cytotoxic activity against human breast cancer cell line (MCF-7). Compounds 6, 7, 9, 10, 11, and 14 displayed significant activity against MCF-7 when compared to doxorubicin, which was used as a reference drug. The synergistic effect of Gamma radiation for the most active derivatives 7, 9, and 11 was also studied and their IC(50) values markedly decreased to 11.9 μM, 11.7 μM, and 11.6 μM, respectively.

Crystal structure of N-(3-chloro-1-methyl-1H-indazol-5-yl)-4-meth­oxy­benzene­sulfonamide

PubMed Central

Chicha, Hakima; Rakib, El Mostapha; Gamouh, Ahmed; Saadi, Mohamed; El Ammari, Lahcen

2014-01-01

In the title compound, C15H14ClN3O3S, the dihedral angle between the planes of the indazole ring system (r.m.s. deviation = 0.007 Å) and the benzene ring is 89.05 (7)°. The meth­oxy C atom deviates from its attached ring by 0.196 (3) Å. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops. The dimers are connected into [010] chains by C—H⋯O inter­actions. PMID:25309293

Mechanistic link between uptake of sulfonamides and bacteriostatic effect: model development and application to experimental data from two soil microorganisms.

PubMed

Focks, Andreas; Klasmeier, Jörg; Matthies, Michael

2010-07-01

Sulfonamides (SA) are antibiotic compounds that are widely used as human and veterinary pharmaceuticals. They are not rapidly biodegradable and have been detected in various environmental compartments. Effects of sulfonamides on microbial endpoints in soil have been reported from laboratory incubation studies. Sulfonamides inhibit the growth of sensitive microorganisms by competitive binding to the dihydropteroate-synthase (DHPS) enzyme of folic acid production. A mathematical model was developed that relates the extracellular SA concentration to the inhibition of the relative bacterial growth rate. Two factors--the anionic accumulation factor (AAF) and the cellular affinity factor (CAF)--determine the effective concentration of an SA. The AAF describes the SA uptake into bacterial cells and varies with both the extra- and intracellular pH values and with the acidic pKa value of an SA. The CAF subsumes relevant cellular and enzyme properties, and is directly proportional to the DHPS affinity constant for an SA. Based on the model, a mechanistic dose-response relationship is developed and evaluated against previously published data, where differences in the responses of Pseudomonas aeruginosa and Panthoea agglomerans toward changing medium pH values were found, most likely as a result of their diverse pH regulation. The derived dose-response relationship explains the pH and pKa dependency of mean effective concentration values (EC50) of eight SA and two soil bacteria based on AAF and CAF values. The mathematical model can be used to extrapolate sulfonamide effects to other pH values and to calculate the CAF as a pH-independent measure for the SA effects on microbial growth. Copyright (c) 2010 SETAC.

Deciphering the Bacterial Microbiome in Huanglongbing-Affected Citrus Treated with Thermotherapy and Sulfonamide Antibiotics

PubMed Central

Powell, Charles A.; Duan, Yongping; Shatters, Robert; Fang, Jingping; Zhang, Muqing

2016-01-01

Huanglongbing (HLB) is a serious citrus disease that threatens the citrus industry. In previous studies, sulfonamide antibiotics and heat treatment suppressed ‘Candidatus Liberibacter asiaticus’ (Las), but did not completely eliminate the Las. Furthermore, there are few reports studying the bacterial microbiome of HLB-affected citrus treated by heat and sulfonamide antibiotics. In this study, combinations of heat (45°C or 40°C) and sulfonamide treatment (sulfathiazole sodium–STZ, or sulfadimethoxine sodium—SDX) were applied to HLB-affected citrus. The bacterial microbiome of HLB-affected citrus following thermotherapy and/or chemotherapy was characterized by PhyloChipTMG3-based metagenomics. Our results showed that the combination of thermotherapy at 45°C and chemotherapy with STZ and SDX was more effective against HLB than thermotherapy alone, chemotherapy alone, or a combination of thermotherapy at 40°C and chemotherapy. The PhyloChipTMG3-based results indicated that 311 empirical Operational Taxonomic Units (eOTUs) were detected in 26 phyla. Cyanobacteria (18.01%) were dominant after thermo-chemotherapy. Thermotherapy at 45°C decreased eOTUs (64.43%) in leaf samples, compared with thermotherapy at 40°C (73.96%) or without thermotherapy (90.68%) and it also reduced bacterial family biodiversity. The eOTU in phylum Proteobacteria was reduced significantly and eOTU_28, representing “Candidatus Liberibacter,” was not detected following thermotherapy at 45°C. Following antibiotic treatment with SDX and STZ, there was enhanced abundance of specific eOTUs belonging to the families Streptomycetaceae, Desulfobacteraceae, Chitinophagaceae, and Xanthomonadaceae, which may be implicated in increased resistance to plant pathogens. Our study further develops an integrated strategy for combating HLB, and also provides new insight into the bacterial microbiome of HLB-affected citrus treated by heat and sulfonamide antibiotics. PMID:27171468

Surface runoff and transport of sulfonamide antibiotics and tracers on manured grassland.

PubMed

Burkhardt, Michael; Stamm, Christian; Waul, Christopher; Singer, Heinz; Müller, Stephan

2005-01-01

Despite their common use in animal production the environmental fate of the veterinary sulfonamide antibiotics after excretion is only poorly understood. We performed irrigation experiments to investigate the transport of these substances with surface runoff on grassland. Liquid manure from pigs treated with sulfadimidine was spiked with sulfadiazine, sulfathiazole, the herbicide atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine), and the conservative tracer bromide and spread onto eight plots. Four plots received the same amounts of the spiked substances in aqueous solution (controls). Apart from the application matrix we varied the time between application and irrigation. Manure increased the runoff volume up to six times compared with the controls. It seemed that manure enhanced the runoff by sealing the soil surface. On manured plots the relative antibiotic concentrations in runoff were higher than on the controls, reaching an average of 0.3% (sulfadiazine), 0.8% (sulfathiazole), and 1.4% (sulfadimidine) of the input concentrations after a 1-d contact time. The corresponding values on the controls were 0.16% for sulfadiazine and 0.08% for sulfathiazole. After 3 d, the maximum values on the manured plots were even higher, whereas they had fallen below the limit of quantification on the controls. As a consequence, the sulfonamide losses were 10 to 40 times larger on the manured plots. The relative mobility of the sulfonamides on the control plots followed the trend expected from their chromatographic separation but the opposite was found on the manured plots. Hence it is important to consider explicitly the physical and chemical effects of manure when assessing the environmental fate of sulfonamides.

A survey of levels of ethyl carbamate in alcoholic beverages in 2009-2012, Hebei Province, China.

PubMed

Liu, Yinping; Wang, Shuhui; Hu, Ping

2013-01-01

Results of a survey of levels of ethyl carbamate (EC) (urethane) in alcoholic beverages carried out in four successive years from 2009 to 2012 by gas chromatography-mass spectrometry (GC/MS) are presented. The beverages were purchased for sampling from Hebei Province of China, including eight main areas of production. The samples comprised wines (n = 212), grain spirits (n = 143) and wine sauces (n = 164). The data show that the average EC content in these kinds of alcoholic beverages remains nearly constant over the years. The results provide valuable data for food authorities to establish maximum limits for EC in China.

Identification of bicyclic hexafluoroisopropyl alcohol sulfonamides as retinoic acid receptor-related orphan receptor gamma (RORγ/RORc) inverse agonists. Employing structure-based drug design to improve pregnane X receptor (PXR) selectivity.

PubMed

Gong, Hua; Weinstein, David S; Lu, Zhonghui; Duan, James J-W; Stachura, Sylwia; Haque, Lauren; Karmakar, Ananta; Hemagiri, Hemalatha; Raut, Dhanya Kumar; Gupta, Arun Kumar; Khan, Javed; Camac, Dan; Sack, John S; Pudzianowski, Andrew; Wu, Dauh-Rurng; Yarde, Melissa; Shen, Ding-Ren; Borowski, Virna; Xie, Jenny H; Sun, Huadong; D'Arienzo, Celia; Dabros, Marta; Galella, Michael A; Wang, Faye; Weigelt, Carolyn A; Zhao, Qihong; Foster, William; Somerville, John E; Salter-Cid, Luisa M; Barrish, Joel C; Carter, Percy H; Dhar, T G Murali

2018-01-15

We disclose the optimization of a high throughput screening hit to yield benzothiazine and tetrahydroquinoline sulfonamides as potent RORγt inverse agonists. However, a majority of these compounds showed potent activity against pregnane X receptor (PXR) and modest activity against liver X receptor α (LXRα). Structure-based drug design (SBDD) led to the identification of benzothiazine and tetrahydroquinoline sulfonamide analogs which completely dialed out LXRα activity and were less potent at PXR. Pharmacodynamic (PD) data for compound 35 in an IL-23 induced IL-17 mouse model is discussed along with the implications of a high Y max in the PXR assay for long term preclinical pharmacokinetic (PK) studies. Copyright © 2017 Elsevier Ltd. All rights reserved.

Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II.

PubMed

Kılıcaslan, Soner; Arslan, Mustafa; Ruya, Zeynep; Bilen, Çigdem; Ergün, Adem; Gençer, Nahit; Arslan, Oktay

2016-12-01

Sulfonamide-bearing thiazole compounds were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase I and II were evaluated. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of the 12 synthesized sulfonamide (5a-l) on the hydratase and esterase activities of these isoenzymes (hCA-I and hCA-II) were studied in vitro. In relation to these activities, the inhibition equilibrium constants (Ki) were determined. The results showed that all the synthesized compounds inhibited the CA isoenzyme activity. Among them 5b was found to be the most active (IC50 = 0.35 μM; Ki: 0.33 μM) for hCA I and hCA II.

N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide hemi-hydrate.

PubMed

Chicha, Hakima; Kouakou, Assoman; Rakib, El Mostapha; Saadi, Mohamed; El Ammari, Lahcen

2013-01-01

The fused five- and six-membered rings in the title compound, C17H16ClN3O3S·0.5H2O, are practically coplanar, with the maximum deviation from the mean plane being 0.057 (3) Å for the C atom bound to the exocyclic N atom. The indazole system makes a dihedral angle of 66.18 (12)° with the plane through the benzene ring, and it is nearly perpendicular to the allyl group, as indicated by the N-N-C-C torsion angle of 79.2 (3)°. In the crystal, the water mol-ecule, lying on a twofold axis, forms O-H⋯N and accepts N-H⋯O hydrogen bonds. Additional C-H⋯O hydrogen bonds contribute to the formation of a chain along the b-axis direction.

Subacute exposure to N-ethyl perfluorooctanesulfonamidoethanol results in the formation of perfluorooctanesulfonate and alters superoxide dismutase activity in female rats.

PubMed

Xie, Wei; Wu, Qian; Kania-Korwel, Izabela; Tharappel, Job C; Telu, Sanjay; Coleman, Mitchell C; Glauert, Howard P; Kannan, Kurunthachalam; Mariappan, S V S; Spitz, Douglas R; Weydert, Jamie; Lehmler, Hans-Joachim

2009-10-01

Perfluorooctanesulfonamides, such as N-ethyl perfluorooctanesulfonamidoethanol (N-EtFOSE), are large scale industrial chemicals but their disposition and toxicity are poorly understood despite significant human exposure. The hypothesis that subacute exposure to N-EtFOSE, a weak peroxisome proliferator, causes a redox imbalance in vivo was tested using the known peroxisome proliferator, ciprofibrate, as a positive control. Female Sprague-Dawley rats were treated orally with N-EtFOSE, ciprofibrate or corn oil (vehicle) for 21 days, and levels of N-EtFOSE and its metabolites as well as markers of peroxisome proliferation and oxidative stress were assessed in serum, liver and/or uterus. The N-EtFOSE metabolite profile in liver and serum was in good agreement with reported in vitro biotransformation pathways in rats and the metabolite levels decreasing in the order perfluorooctanesulfonate > perfluorooctanesulfonamide ~ N-ethyl perfluorooctanesulfonamidoacetate > perfluorooctanesulfonamidoethanol approximately N-EtFOSE. Although N-EtFOSE treatment significantly decreased the growth rate, increased relative liver weight and activity of superoxide dismutases (SOD) in liver and uterus (total SOD, CuZnSOD and MnSOD), a metabolic study revealed no differences in the metabolome in serum from N-EtFOSE-treated and control animals. Ciprofibrate treatment increased liver weight and peroxisomal acyl Co-A oxidase activity in the liver and altered antioxidant enzyme activities in the uterus and liver. According to NMR metabolomic studies, ciprofibrate treated animals had altered serum lipid profiles compared to N-EtFOSE-treated and control animals, whereas putative markers of peroxisome proliferation in serum were not affected. Overall, this study demonstrates the biotransformation of N-EtFOSE to PFOS in rats that is accompanied by N-EtFOSE-induced alterations in antioxidant enzyme activity.

Subacute Exposure to N-Ethyl Perfluorooctanesulfonamidoethanol Results in the Formation of Perfluorooctanesulfonate and Alters Superoxide Dismutase Activity in Female Rats

PubMed Central

Xie, Wei; Wu, Qian; Kania-Korwel, Izabela; Tharappel, Job C.; Telu, Sanjay; Coleman, Mitchell C.; Glauert, Howard P.; Kannan, Kurunthachalam; Santhana Mariappan, S. V.; Spitz, Douglas R.; Weydert, Jamie; Lehmler, Hans-Joachim

2009-01-01

Perfluorooctanesulfonamides, such as N-ethyl perfluorooctanesulfonamidoethanol (N-EtFOSE), are large scale industrial chemicals but their disposition and toxicity are poorly understood despite significant human exposure. The hypothesis that subacute exposure to N-EtFOSE, a weak peroxisome proliferator, causes a redox imbalance in vivo was tested using the known peroxisome proliferator, ciprofibrate, as a positive control. Female Sprague-Dawley rats were treated orally with N-EtFOSE, ciprofibrate or corn oil (vehicle) for 21 days, and levels of N-EtFOSE and its metabolites as well as markers of peroxisome proliferation and oxidative stress were assessed in serum, liver and/or uterus. The N-EtFOSE metabolite profile in liver and serum was in good agreement with reported in vitro biotransformation pathways in rats and the metabolite levels decreasing in the order perfluorooctanesulfonate ≫ perfluorooctanesulfonamide ∼ N-ethyl perfluorooctanesulfonamidoacetate ≫ perfluorooctanesulfonamidoethanol ∼ N-EtFOSE. Although N-EtFOSE treatment significantly decreased the growth rate, increased relative liver weight and activity of superoxide dismutases (SOD) in liver and uterus (total SOD, CuZnSOD and MnSOD), a metabolic study revealed no differences in the metabolome in serum from N-EtFOSE-treated and control animals. Ciprofibrate treatment increased liver weight and peroxisomal acyl Co-A oxidase activity in the liver and altered antioxidant enzyme activities in the uterus and liver. According to NMR metabolomic studies, ciprofibrate treated animals had altered serum lipid profiles compared to N-EtFOSE-treated and control animals, whereas putative markers of peroxisome proliferation in serum were not affected. Overall, this study demonstrates the biotransformation of N-EtFOSE to PFOS in rats that is accompanied by N-EtFOSE-induced alterations in antioxidant enzyme activity. PMID:19544052

(S)-N-{1-[5-(4-Chloro-benzyl-sulfanyl)-1,3,4-oxadiazol-2-yl]eth-yl}-4-methyl-benzene-sulfonamide.

PubMed

Syed, Tayyaba; Hameed, Shahid; Jones, Peter G

2011-10-01

The title compound, C(18)H(18)ClN(3)O(3)S(2), adopts by folding the form of a distorted disc. Inter-planar angles are 29.51 (7) and 63.43 (7)° from the five-membered ring to the aromatic systems and 34.80 (6)° between these two latter rings. The absolute configuration was confirmed by determination of the Flack parameter. In the crystal, the mol-ecules are linked by four hydrogen bonds, one classical (N-H⋯N) and three 'weak' (C-H⋯O), forming layers parallel to the ac plane; these are in turn linked in the third dimension by Cl⋯N [3.1689 (16) Å] and Cl⋯O [3.3148 (13) Å] contacts to the heterocyclic ring.

QSAR studies on carbonic anhydrase inhibitors: a case of ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides.

PubMed

Agrawal, Vijay K; Sharma, Ruchi; Khadikar, Padmakar V

2002-09-01

QSAR studies on modelling of biological activity (hCAI) for a series of ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides have been made using a pool of topological indices. Regression analysis of the data showed that excellent results were obtained in multiparametric correlations upon introduction of indicator parameters. The predictive abilities of the models are discussed using cross-validation parameters.

Accumulation of sulfonamide resistance genes in arable soils due to repeated application of manure containing sulfadiazine.

PubMed

Heuer, Holger; Solehati, Qodiah; Zimmerling, Ute; Kleineidam, Kristina; Schloter, Michael; Müller, Tanja; Focks, Andreas; Thiele-Bruhn, Sören; Smalla, Kornelia

2011-04-01

Two soils were amended three times with pig manure. The abundance of sulfonamide resistance genes was determined by quantitative PCR 2 months after each application. In both soils treated with sulfadiazine-containing manure, the numbers of copies of sul1 and sul2 significantly increased compared to numbers after treatments with antibiotic-free manure or a control and accumulated with repeated applications.

New superacid synthesized (fluorinated) tertiary benzenesulfonamides acting as selective hCA IX inhibitors: toward a new mode of carbonic anhydrase inhibition by sulfonamides.

PubMed

Métayer, Benoît; Mingot, Agnès; Vullo, Daniella; Supuran, Claudiu T; Thibaudeau, Sébastien

2013-07-11

Tertiary substituted (fluorinated) benzenesulfonamides were synthesized in superacid HF/SbF5 and tested as inhibitors of human carbonic anhydrases (hCAs, EC 4.2.1.1). Strong selectivity toward tumor-associated hCA IX, without inhibiting the offtarget hCA II, was observed, pointing out to a new mechanism of action compared to classical sulfonamides.

Determination of sulfonamide antibiotics and metabolites in liver, muscle and kidney samples by pressurized liquid extraction or ultrasound-assisted extraction followed by liquid chromatography-quadrupole linear ion trap-tandem mass spectrometry (HPLC-QqLIT-MS/MS).

PubMed

Hoff, Rodrigo Barcellos; Pizzolato, Tânia Mara; Peralba, Maria do Carmo Ruaro; Díaz-Cruz, M Silvia; Barceló, Damià

2015-03-01

Sulfonamides are widely used in human and veterinary medicine. The presence of sulfonamides residues in food is an issue of great concern. Throughout the present work, a method for the targeted analysis of 16 sulfonamides and metabolites residue in liver of several species has been developed and validated. Extraction and clean-up has been statistically optimized using central composite design experiments. Two extraction methods have been developed, validated and compared: i) pressurized liquid extraction, in which samples were defatted with hexane and subsequently extracted with acetonitrile and ii) ultrasound-assisted extraction with acetonitrile and further liquid-liquid extraction with hexane. Extracts have been analyzed by liquid chromatography-quadrupole linear ion trap-tandem mass spectrometry. Validation procedure has been based on the Commission Decision 2002/657/EC and included the assessment of parameters such as decision limit (CCα), detection capability (CCβ), sensitivity, selectivity, accuracy and precision. Method׳s performance has been satisfactory, with CCα values within the range of 111.2-161.4 µg kg(-1), limits of detection of 10 µg kg(-1) and accuracy values around 100% for all compounds. Copyright © 2014 Elsevier B.V. All rights reserved.

Simultaneous detection of antibacterial sulfonamides in a microfluidic device with amperometry.

PubMed

Won, So-Young; Chandra, Pranjal; Hee, Tak Seong; Shim, Yoon-Bo

2013-01-15

A highly sensitive and robust method for simultaneous detection of five sulfonamide drugs is developed by integrating the preconcentration and separation steps in a microfluidic device. An ampetrometry is performed for the selective detection of sulfonamides using an aluminum oxide-gold nanoparticle (Al(2)O(3)-AuNPs) modified carbon paste (CP) electrode at the end of separation channel. The preconcentration capacity of the channel is enhanced by using the field amplified sample stacking and the field amplified sample injection techniques. The experimental parameters affecting the analytical performances, such as pH, % of Al(2)O(3), volume of AuNPs, buffer concentration, and water plug length are optimized. A reproducible response is observed during the multiple injections of samples with RSDs<4%. The calibration plots are linear with the correlation coefficient between 0.991 and 0.997 over the range between 0.01 and 2025pM. The detection limits of five drugs are determined to be between 0.91 (±0.03) and 2.21 (±0.09)fM. The interference effects of common biological compounds are also investigated and the applicability of the method to the direct analysis of sulfonamides in real meat samples is successfully demonstrated. Long term stability of the modified electrode was also investigated. Copyright © 2012 Elsevier B.V. All rights reserved.

40 CFR Table 36 to Subpart G of... - Compound Lists Used for Compliance Demonstrations for Enhanced Biological Treatment Processes...

Code of Federal Regulations, 2011 CFR

2011-07-01

.... Trichlorobenzene 1,2,4. Dimethylaniline N,N. Trichlorophenol 2,4,6 Epichlorohydrin. Triethylamine Ethyl Acrylate. Ethylbenzene. Ethylene Oxide. Ethylene Dibromide. Hexachlorobutadiene. Hexachloroethane. Hexane-n. Methyl...

40 CFR Table 36 to Subpart G of... - Compound Lists Used for Compliance Demonstrations for Enhanced Biological Treatment Processes...

Code of Federal Regulations, 2014 CFR

2014-07-01

.... Trichlorobenzene 1,2,4. Dimethylaniline N,N. Trichlorophenol 2,4,6 Epichlorohydrin. Triethylamine Ethyl Acrylate. Ethylbenzene. Ethylene Oxide. Ethylene Dibromide. Hexachlorobutadiene. Hexachloroethane. Hexane-n. Methyl...

40 CFR Table 36 to Subpart G of... - Compound Lists Used for Compliance Demonstrations for Enhanced Biological Treatment Processes...

Code of Federal Regulations, 2012 CFR

2012-07-01

.... Trichlorobenzene 1,2,4. Dimethylaniline N,N. Trichlorophenol 2,4,6 Epichlorohydrin. Triethylamine Ethyl Acrylate. Ethylbenzene. Ethylene Oxide. Ethylene Dibromide. Hexachlorobutadiene. Hexachloroethane. Hexane-n. Methyl...

40 CFR Table 36 to Subpart G of... - Compound Lists Used for Compliance Demonstrations for Enhanced Biological Treatment Processes...

Code of Federal Regulations, 2013 CFR

2013-07-01

.... Trichlorobenzene 1,2,4. Dimethylaniline N,N. Trichlorophenol 2,4,6 Epichlorohydrin. Triethylamine Ethyl Acrylate. Ethylbenzene. Ethylene Oxide. Ethylene Dibromide. Hexachlorobutadiene. Hexachloroethane. Hexane-n. Methyl...

Bromidotetra­kis­(1H-2-ethyl-5-methyl­imidazole-κN 3)copper(II) bromide

PubMed Central

Godlewska, Sylwia; Baranowska, Katarzyna; Socha, Joanna; Dołęga, Anna

2011-01-01

The CuII ion in the title compound, [CuBr(C6H10N2)4]Br, is coordinated in a square-based-pyramidal geometry by the N atoms of four imidazole ligands and a bromide anion in the apical site. Both the CuII and Br− atoms lie on a crystallographic fourfold axis. In the crystal, the [CuBr(C6H10N2)4]+ complex cations are linked to the uncoordinated Br− anions (site symmetry ) by N—H⋯Br hydrogen bonds, generating a three-dimensional network. The ethyl group of the imidazole ligand was modelled as disordered over two orientations with occupancies of 0.620 (8) and 0.380 (8). PMID:22199662

Sensitive determination of sulfonamides in environmental water by capillary electrophoresis coupled with both silvering detection window and in-capillary optical fiber light-emitting diode-induced fluorescence detector.

PubMed

Ji, Hongyun; Wu, Yu; Duan, Zhijuan; Yang, Feng; Yuan, Hongyan; Xiao, Dan

2017-02-01

A new detector, silvering detection window and in-capillary optical fiber light-emitting diode-induced fluorescence detector (SDW-ICOF-LED-IFD), is introduced for capillary electrophoresis (CE). The strategy of the work was that half surface of the detection window was coated with silver mirror, which could reflect the undetected fluorescence to the photomultiplier tube to be detected, consequently enhancing the detection sensitivity. Sulfonamides (SAs) are important antibiotics that achieved great applications in many fields. However, they pose a serious threat on the environment and human health when they enter into the environment. The SDW-ICOF-LED-IFD-CE system was used to determine fluorescein isothiocyanate (FITC)-labeled sulfadoxine (SDM), sulfaguanidine (SGD) and sulfamonomethoxine sodium (SMM-Na) in environmental water. The detection results obtained by the SDW-ICOF-LED-IFD-CE system were compared to those acquired by the CE with in-capillary optical fiber light-emitting diode-induced fluorescence detection (ICOF-LED-IFD-CE). The limits of detection (LODs) of SDW-ICOF-LED-IFD-CE and ICOF-LED-IFD-CE were 1.0-2.0 nM and 2.5-7.7 nM (S/N = 3), respectively. The intraday (n = 6) and interday (n = 6) precision of migration time and corresponding peak area for both types of CE were all less than 0.86% and 3.68%, respectively. The accuracy of the proposed method was judged by employing standard addition method, and recoveries obtained were in the range of 92.5-102.9%. The results indicated that the sensitivity of the SDW-ICOF-LED-IFD-CE system was improved, and that its reproducibility and accuracy were satisfactory. It was successfully applied to analyze SAs in environmental water. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

PubMed

Chicha, Hakima; Rakib, El Mostapha; Chigr, Mohamed; Saadi, Mohamed; El Ammari, Lahcen

2014-09-01

The 3-chloro-1H-indazole system in the title mol-ecule, C17H16ClN3O2S, is almost planar, with the largest deviation from the mean plane being 0.029 (2) Å for one of the N atoms. This system is nearly perpendicular to the allyl chain, as indicated by the C-C-N-N torsion angle of -90.1 (6)° between them. The allyl group is split into two fragments, the major component has a site occupancy of 0.579 (7). The indazole system makes a dihedral angle of 47.53 (10)° with the plane through the benzene ring. In the crystal, mol-ecules are connected by N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Surface sulfonamide modification of poly(N-isopropylacrylamide)-based block copolymer micelles to alter pH and temperature responsive properties for controlled intracellular uptake.

PubMed

Cyphert, Erika L; von Recum, Horst A; Yamato, Masayuki; Nakayama, Masamichi

2018-06-01

Two different surface sulfonamide-functionalized poly(N-isopropylacrylamide)-based polymeric micelles were designed as pH-/temperature-responsive vehicles. Both sulfadimethoxine- and sulfamethazine-surface functionalized micelles were characterized to determine physicochemical properties, hydrodynamic diameters, zeta potentials, temperature-dependent size changes, and lower critical solution temperatures (LCST) in both pH 7.4 and 6.8 solutions (simulating both physiological and mild low pH conditions), and tested in the incorporation of a proof-of-concept hydrophobic antiproliferative drug, paclitaxel. Cellular uptake studies were conducted using bovine carotid endothelial cells and fluorescently labeled micelles to evaluate if there was enhanced cellular uptake of the micelles in a low pH environment. Both variations of micelles showed enhanced intracellular uptake under mildly acidic (pH 6.8) conditions at temperatures slightly above their LCST and minimal uptake at physiological (pH 7.4) conditions. Due to the less negative zeta potential of the sulfamethazine-surface micelles compared to sulfadimethoxine-surface micelles, and the proximity of their LCST to physiological temperature (37°C), the sulfamethazine variation was deemed more amenable for clinically relevant temperature and pH-stimulated applications. Nevertheless, we believe both polymeric micelle variations have the capacity to be implemented as an intracellular drug or gene delivery system in response to mildly acidic conditions. © 2018 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 106A: 1552-1560, 2018. © 2018 Wiley Periodicals, Inc.

Characterization of Integrons and Sulfonamide Resistance Genes among Bacteria from Drinking Water Distribution Systems in Southwestern Nigeria.

PubMed

Adesoji, Ayodele T; Ogunjobi, Adeniyi A; Olatoye, Isaac O

2017-01-01

The emergence of antibiotic resistance among pathogenic bacteria in clinical and environmental settings is a global problem. Many antibiotic resistance genes are located on mobile genetic elements such as plasmids and integrons, enabling their transfer among a variety of bacterial species. Water distribution systems may be reservoirs for the spread of antibiotic resistance. Bacteria isolated from raw, treated, and municipal tap water samples from selected water distribution systems in south-western Nigeria were investigated using the point inoculation method with seeded antibiotics, PCR amplification, and sequencing for the determination of bacterial resistance profiles and class 1/2 integrase genes and gene cassettes, respectively. sul1,sul2, and sul3 were detected in 21.6, 27.8, and 0% of the isolates, respectively (n = 162). Class 1 and class 2 integrons were detected in 21.42 and 3.6% of the isolates, respectively (n = 168). Genes encoding resistance to aminoglycosides (aadA2, aadA1, and aadB), trimethoprim (dfrA15, dfr7, and dfrA1), and sulfonamide (sul1) were detected among bacteria with class 1 integrons, while genes that encodes resistance to strepthothricin (sat2) and trimethoprim (dfrA15) were detected among bacteria with class 2 integrons. Bacteria from these water samples are a potential reservoir of multidrug-resistant traits including sul genes and mobile resistance elements, i.e. the integrase gene. © 2016 S. Karger AG, Basel.

anti-Selective Asymmetric Henry Reaction Catalyzed by a Heterobimetallic Cu-Sm-Aminophenol Sulfonamide Complex.

PubMed

Li, Yang; Deng, Ping; Zeng, Youmao; Xiong, Yan; Zhou, Hui

2016-04-01

A novel heterobimetallic Cu/Sm/aminophenol sulfonamide complex has been developed by a convenient one-pot method for the anti-selective asymmetric Henry reaction. The corresponding anti-β-nitro alcohols are obtained in up to 99% yield, >30:1 dr, and 98% ee. The results of control experiments and ESI-MS analysis of the complex indicate that the monomeric bimetallic Cu/Sm/1 complex would be the active species.

Reduction in lipophilicity improved the solubility, plasma–protein binding, and permeability of tertiary sulfonamide RORc inverse agonists

DOE Office of Scientific and Technical Information (OSTI.GOV)

Fauber, Benjamin P.; René, Olivier; de Leon Boenig, Gladys

2014-08-01

Using structure-based drug design principles, we identified opportunities to reduce the lipophilicity of our tertiary sulfonamide RORc inverse agonists. The new analogs possessed improved RORc cellular potencies with >77-fold selectivity for RORc over other nuclear receptors in our cell assay suite. The reduction in lipophilicity also led to an increased plasma–protein unbound fraction and improvements in cellular permeability and aqueous solubility.