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1.
Franz Mlynek Markus Himmelsbach Wolfgang Buchberger Christian W. Klampfl 《Electrophoresis》2021,42(4):482-489
The (tentative) identification of unknown drug-related phase II metabolites in plants upon drug uptake remains a challenging task despite improved analytical instrument performance. To broaden the knowledge of possible drug metabolization, a fast-screening approach for the tentative identification of drug-related phase II metabolites is presented in this work. Therefore, an in silico database for the three non-steroidal anti-inflammatory drugs (ketoprofen, mefenamic acid, and naproxen) and a sub-group of their theoretical phase II metabolites (based on combinations with glucose, glucuronic acid, and malonic acid) was created. Next, the theoretical exact masses (protonated species and ammonia adducts) were calculated and used as precursor ions in an autoMS/MS measurement method. The applicability of this workflow was tested on the example of eleven edible plants, which were hydroponically grown in solutions containing the respective drug at a concentration level of 20 mg/L. For the three drugs investigated this led to the tentative identification of 41 metabolites (some of them so far not described in this context), such as combinations of hydroxylated mefenamic acid with up to four glucose units or hydroxylated mefenamic acid with two glucose and three malonic acid units. 相似文献
2.
Natalia Migowska Piotr Stepnowski Monika Paszkiewicz Marek Gołębiowski Jolanta Kumirska 《Analytical and bioanalytical chemistry》2010,397(7):3029-3034
Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most common groups of pharmaceuticals detected in environmental
matrices. Although several derivatization procedures have been employed in the gas chromatographic analysis of NSAIDs, the
application of trimethylsilyldiazomethane has never yet been reported. This work has studied the derivatization of widely
used NSAIDs (ibuprofen, ketoprofen and naproxen) by trimethylsilyldiazomethane. Special emphasis was placed on the influence
of temperature and reaction time on the reaction yield, and on the determination of the instrumental detection limit. The
results are compared with those obtained by methylation using boron trifluoride methanol solution, and by silylation with
a mixture of N,O-bis(trimethylsilyl)trifluoroacetamide and trimethylchlorosilane (99:1, v/v) and with N-methyl-N-[tert-butyldimethylsilyl]trifluoroacetamide. The derivatization of ibuprofen, ketoprofen and naproxen by trimethylsilyldiazomethane
was shown to be simple, fast, efficient, and suitable for trace analysis (the respective instrumental detection limits for
ibuprofen naproxen, and ketoprofen were 2, 4, and 4 ng). Trimethylsilyldiazomethane can be used as an alternative reagent
for determining acidic drugs in environmental matrices. 相似文献
3.
Benedicte Soulet Annick Tauxe Joseph Tarradellas 《International journal of environmental analytical chemistry》2013,93(10):659-667
Five acidic drugs (clofibric acid, ibuprofen, ketoprofen, mefenamic acid and diclofenac) were chosen in order to determine their behavior in a sewage treatment plant (STP). An analytical method using solid phase extraction (SPE) and a gas chromatograph coupled with a mass spectrometer (GC-MS) was used. The results show that four pharmaceuticals (clofibric acid, ketoprofen, mefenamic acid and diclofenac) are not well removed by treatment in Swiss STPs. Maximum concentration in the effluent was determined for mefenamic acid up to 1.0 µg/L. This component seems to be relevant in Swiss STPs effluents and we can expect its presence in surface waters. 相似文献
4.
Supercritical fluid chromatography (SFC) was investigated for the separation of non-steroidal anti-inflammatory agents (NSAIs). Three different stationary phases (SB-methyl-100, SB-biphenyl-30, and SB-cyanopropyl-50) were compared for the separation of the compounds. Baseline separation of a flufenamic acid, mefenamic acid, fenbufen and indomethacin mixture was achieved on the SB-biphenyl-30 column using a pressure gradient. A mixture containing flufenamic acid, mefenamic acid, acetylsalicylic acid, ketoprofen and fenbufen and another mixture containing ibuprofen, fenoprofen, naproxen, ketoprofen and tolmetin were well separated on the SB-cyanopropyl-50 column using pressure gradients. Typical analysis time for a mixture of NSAIs on the biphenyl or cyanopropyl column was approximately 20-25 min. Application of the method using the biphenyl column to the determination of NSAIs present in selected commercial dosage forms was demonstrated. 相似文献
5.
P C Ioannou N V Rusakova D A Andrikopoulou K M Glynou G M Tzompanaki 《The Analyst》1998,123(12):2839-2843
Terbium sensitized fluorescence was used to develop a sensitive and simple spectrofluorimetric method for the determination of the anthranilic acid derivatives furosemide and mefenamic and tolfenamic acids. The method makes use of radiative energy transfer from anthranilates to terbium ions in alkaline methanolic solutions. Optimum conditions for the formation of the anthranilate-Tb3+ complexes were investigated. Under optimized conditions, the detection limits are 6 x 10(-9), 1.4 x 10(-8) and 9.0 x 10(-9) mol l-1 for furosemide, mefenamic acids and tolfenamic acid, respectively. The range of application is 2.5 x 10(-8)-5.0 x 10(-5) mol l-1 for all three drugs. The method was successfully applied to the determination of furosemide and mefenamic and tolfenamic acids in serum after extraction of the samples with ethyl acetate, evaporation of the organic layer under a stream of nitrogen at 40 degrees C and reconstitution of the residue with alkaline methanolic terbium solution prior to instrumental measurement. The mean recoveries from serum samples spiked with furosemide (5.0 x 10(-7), 2.0 x 10(-6) and 8.0 x 10(-6) mol l-1), mefenamic acid (3.0 x 10(-6), 9.0 x 10(-6) and 3.0 x 10(-5) mol l-1) and tolfenamic acid (3.1 x 10(-6), 12.5 x 10(-6) and 2.5 x 10(-5) mol l-1) were 96 +/- 8, 101 +/- 5 and 98 +/- 7%, respectively. The within-run precision (RSD) for the method for two serum samples of each drug varied from 2 to 8% and the day-to-day precision for two concentration levels varied from 2 to 13%. 相似文献
6.
《Comptes Rendus Chimie》2016,19(8):963-970
In the last few decades, the presence of pharmaceutical products in the environment is known under the name of emerging contaminants. These substances can enter the aquatic environment via different sources, as parent compounds, metabolites or a combination of both. In this work, we have investigated the presence of four pharmaceutical active compounds belonging to the group of Non-Steroidal Anti-Inflammatory Drugs (NSAIDs), in wastewater, surface water and drinking water of Algiers, which have a direct impact on the Mediterranean Sea. The target analytes (ibuprofen (IBU), naproxen (NAP), ketoprofen (KET), and diclofenac (DIC)), were extracted from the water samples by using Solid Phase Extraction Oasis® HLB Cartridges; the identification and quantification were realized by Gas Chromatography–Mass Spectrometry (GC–MS). To obtain the best resolution and precision, N-methyl-N-(trimethylsilyl) trifluoroacetamide (MSTFA) was used as the derivatization reagent and ibuprofen-d3 was used as the internal standard. The obtained recoveries were good, ranging from 82% for ketoprofen to 120% for naproxen with relatively small standard deviations (≤20%). The target compounds were detected in wastewater, influent/effluent with concentrations ranging from 155.5 to 6554 ng/L, implicating removal efficiencies of wastewater treatment plants (WWTPs), between 30.3 and 95%. The surface water was also contaminated with pharmaceuticals from 72.9 ng/L for diclofenac to 228.3 ng/L for naproxen. In addition, the occurrence of ibuprofen and ketoprofen in drinking water, at concentrations of 142.1 and 110.9 ng/L, respectively, attracts concerns about possible impacts on human health. 相似文献
7.
Alejandro Lapresta-Fernández Piotr J. Cywinski Artur J. Moro Gerhard J. Mohr 《Analytical and bioanalytical chemistry》2009,395(6):1821-1830
We present the synthesis of fluorescent acrylamide nanoparticles (FANs) capable of recognizing non-steroidal anti-inflammatory
drugs (NSAIDs) in buffered aqueous solutions. Within this important group, we selected naproxen, one of the 2-arylpropionic
acids (profens), due to its use for the treatment of moderate pain, fever, and inflammation. The nanosensors were prepared
under mild conditions of inverse microemulsion polymerization using aqueous acrylamide as the monomer and N,N′-methylenebisacrylamide as the cross-linker, employing the surfactants polyoxyethylene-4-lauryl ether (Brij?30) and sodium
bis(2-ethylhexyl)sulfosuccinate in hexane. Furthermore, a fluorescent monomer, (E)-4-[4-(dimethylamino)styryl]-1-[4-(methacryloyloxymethyl)benzyl]pyridinium chloride (mDMASP) has been synthesized and incorporated
into the nanoparticles. The nanosensors exhibit a broad absorbance at around 460 nm and a structureless fluorescence band
with maximum at 590 nm in 0.5 M phosphate buffer (pH = 7.2). The recognition process is performed on the basis of ionic interactions
which are monitored by the fluorescence increase at 590 nm upon addition of different concentrations of naproxen. The FANs
show a size distribution in the range of 20–80 nm, with a hydrodynamic diameter of 34 nm. In order to assess the selectivity
of the FANs, a systematic study was conducted on the effect produced by drugs and biomolecules that could interfere with the
analysis of naproxen. 相似文献
8.
Daniel de la Pea Cristina Martí Santi Noneil Luis A. Martínez Miguel A. Miranda 《Photochemistry and photobiology》1997,65(5):828-832
Abstract— Time-resolved near infrared emission studies have been carried out on a series of nonsteroidal anti inflammatory 2-arylpropionic acids, in order to assess their ability to photosensitize the production of singlet molecular oxygen O2(1Δg). Benoxaprofen, naproxen, tiaprofenic acid, suprofen, ketoprofen and carprofen showed quantum yields for this process (φΔ) in the range 0.2-0.7 in acetonitrile. Deprotonation of the propionic acid moiety in mixtures of acetonitrile-ethanol (4:1) basified with KOH produced a systematic decrease in φΔ for all compounds with the exception of naproxen. This effect was even more dramatic in D2O-based phosphate buffer, where no singlet oxygen could be detected for benoxaprofen, ketoprofen or carprofen. The above results are consistent with the occurrence of competing photochemical reactions of 2-arylpropionic acids in different media and particularly with the enhanced photodecarboxylation from the carboxylate anions. 相似文献
9.
Ingrida Tumosien? Zigmuntas Jonas Beresnevi?ius 《Monatshefte für Chemie / Chemical Monthly》2009,43(9):1523-1528
Abstract
Reaction of 3,3′-[(4-alkoxyphenyl)imino]bis(propanoic acid hydrazides) with CS2 in alkaline solution and subsequent acidification gave 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(1,3,4-oxadiazole-2(3H)-thiones). The same dihydrazides on reaction with phenyl isocyanates or phenyl isothiocyanates were converted to bis[N′-(phenylaminocarbonyl)propanoic acid hydrazides] and bis[N′-(phenylaminocarbonothioyl)propanoic acid hydrazides], which underwent cyclization in alkaline medium to produce 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-ones) and their 3-thio analogues, whereas in sulfuric acid or POCl3 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(N-phenyl-1,3,4-oxadiazol-2-amines) and 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(N-phenyl-1,3,4-thiadiazol-2-amines) were obtained. 相似文献10.
The tetraphosphine all‐cis‐1,2,3,4‐tetrakis(diphenylphosphinomethyl)cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl]2 affords an efficient catalyst of the coupling of 2‐chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2‐arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross‐coupling reactions of methyl 2‐chloroacrylate with arylboronic acids give simple access to 2‐phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen. 相似文献
11.
Acylation of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with the acyl chlorides of naproxen, ibuprofen, and 2-phenylpropionic acid has been found to lead to efficient kinetic resolution with predominant formation of the (S,S)-(R,R)-diastereoisomers. The highest acylation stereoselectivity was found in toluene at -20°C. No significant kinetic resolution of N-(sec-butyl)aniline and 2-methylpiperidine was achieved by using 2-arylpropionyl chlorides. 相似文献
12.
Alina A. Beloborodova Vasily S. Minkov Elena V. Boldyreva 《Acta Crystallographica. Section C, Structural Chemistry》2016,72(12):997-1001
The loop diuretic furosemide is used widely in the treatment of congestive heart failure and edema, and is practically insoluble in water. The physicochemical and pharmacokinetic properties of drugs can be modified by preparing the drug in an appropriate solid‐state form. A new solvate of furosemide with dimethylacetamide (DMA) {systematic name: 4‐chloro‐2‐[(furan‐2‐yl)methylamino]‐5‐sulfamoylbenzoic acid N,N‐dimethylacetamide disolvate}, C12H11ClN2O5S·2C4H9NO, (I), is reported. The channeled structure formed on slow crystallization contains DMA solvent molecules in its channels. This structure adds to the evidence of varied conformations observed across all known structures, so supporting the idea that this flexible molecule has conformational lability. The current structure also differs from those of other previously known furosemide solvates in the number of solvent molecules per furosemide molecule, viz. 2:1 instead of 1:1. Desolvation of (I) gives the most stable form of furosemide, i.e. Form I. 相似文献
13.
Concern is growing over the contamination of the environment with pharmaceutical residues, among which non-steroidal anti-inflammatory
drugs (NSAIDs) are one of the most abundant groups. Their widespread appearance in the aquatic environment is because of their
high consumption and their incomplete removal during wastewater treatment. Because effective operation of wastewater-treatment
plants is important for minimising the release of xenobiotic compounds, for example pharmaceutical products, into the aquatic
environment, our study focuses on removal of commonly used NSAIDs (ibuprofen, naproxen, ketoprofen, diclofenac) and clofibric
acid in a specially designed small-scale pilot wastewater treatment plant (PWWTP). This study shows that, except for diclofenac,
steady-rate removal of NSAIDs over a two-year monitoring period has been achieved. Elimination of the compounds in the PWWTP
was ≥87% for ibuprofen, naproxen and ketoprofen but only 49–59% for diclofenac. We also studied clofibric acid. Results after
one month of operation revealed 30% elimination with no sign of adaptation by the biomass. Also described are degradation
products of diclofenac, which we were able to identify because of the similarity of their mass spectra with those in the NIST
library and by comparing the retention times of different compounds. Although the structures of these compounds were confirmed
with a high probability (99%), we still need to compare the fragmentation of authentic compounds with degradation products
formed under our experimental conditions. Degradation products of ibuprofen, naproxen, ketoprofen, and clofibric acid were
found but these must be identified by use of high-resolution mass spectrometry and analysis of authentic compounds. 相似文献
14.
Thiocarbamoylation of 5-aminosalicylic acid with tetramethylthiuram disulfide afforded 5-(N′,N′-dimethylthioureido)salicyclic acid. Treatment of the latter with mineral acids or Ac2O gave 5-isothiocyanatosalicylic acid whose reaction with ethanolamine yielded 5-[N′-(2-hydroxyethyl)thioureido]salicylic acid. The latter underwent cyclization under the action of TsOH to form 5-(2-thiazolin-2-ylamino)salicylic
acid.
For Part 2, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2315–2318, December, 1999. 相似文献
15.
In this paper, naproxen was intercalated into Zn–Al layered double hydroxides (LDHs) by ion exchange method to obtain naproxen/LDHs
nanohybrids. The effects of the contact time, the composition, and the structural charge density (σ
S,T
) and the specific surface area of LDHs, and pH value on the uptake of naproxen on LDHs, and the release of naproxen from
the naproxen/LDHs nanohybrids were investigated. The adsorption isotherm curves of naproxen on the LDHs obey the Langmuir
equation, and apparent monolayer capacity (A
m) in units of mmol m−2 increases with the increase of the σ
S,T
value of the LDHs samples. The release rate of naproxen from the naproxen/LDHs nanohybrids decreases with the increase of
the σ
S,T
value of the LDHs samples and is much lower than that of naproxen troche, indicating that the naproxen/LDHs nanohybrid is
an efficient drug-controlled release system. In the pH range of 6~11.5, the uptake amount (A
eq) of naproxen on the LDHs decreases with the increase of pH value. The A
m values of LDHs(Cl−) are much higher than that of , which may contribute to that LDHs(Cl−), which has a stronger anion exchange ability than . The naproxen molecules are possibly adsorbed on each surface of the basal layer of LDHs. In other words, a bilayer is formed
in the gallery of LDHs. 相似文献
16.
Two diimide-dicarboxylic acids, 2,2-bis[N-(4-carboxyphenyl)phthalimidyl]hexafluoropropane (p-I) and 2,2,-bis[N-(3-carboxyphenyl)phthalimidyl]hexafluoropropane (m-I), were prepared by azeotropic condensation of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride and p-aminobenzoic acid or m-aminobenzoic acid at a 1:2 molar ratio in N,N-dimethylacetamide/toluene. Two series of organosoluble and colorless poly(amide–imide)s were synthesized from diimide–diacid
p-I or m-I with ten kinds of aromatic diamines by direct polycondensation using triphenyl phosphite and pyridine as condensing agents.
The thin films cast from N,N-dimethylacetamide were measured by UV–vis spectroscopy and Macbeth color-eye colorimetery, the cutoff wavelengths of almost
all the films were below 400 nm (361–389 nm) and the values of the parameter b* were between 15.31 and 34.72; these polymers are much lighter in color than other analogous polymers. Almost all the polymer
were soluble in N-methyl-2-pyrrolodone, N,N-dimethylacetamide, N,N-dimethylformamide and dimethyl sulfoxide, and some polymers could dissolve in less polar solvents, such as dioxane and tetrahydrofuran,
etc. The cast films exhibited yield strengths of 95–131 MPa, tensile strengths ranging from 92 to 130 MPa, elongations at
break from 9 to 27%, and initial moduli from 2.1 to 3.3 GPa. The poly(amide–imide)s had glass-transition temperatures between
259 and 328°C and 10%-weight-loss temperatures above 510 °C in nitrogen and air, indicating excellent thermal stability.
Received: 25 April 2001 Accepted: 27 June 2001 相似文献
17.
J. Migdalski B. Bas T. Blaz J. Golimowski A. Lewenstam 《Journal of Solid State Electrochemistry》2009,13(1):149-155
A procedure for an all-plastic electrochemical cell comprising miniaturized planar indicator and reference electrodes is described.
All electrodes are based on conducting polymers, are fully integrated, and contain no internal electrolyte. The reference
microsensors were deposited via electrochemical polymerization from a water solution containing the monomer 3,4-ethylenedioxythiophene
(EDOT) or 1-methylpyrrole (MPy) and a biochemical buffer 3-(N-morpholino) propanesulfonic acid [MOPS], 2-(N-morpholino) ethanesulfonic acid [MES], or 2-hydroxy-5-sulfobenzoic acid [SSA]). Ion-sensitive microelectrodes were prepared
by the deposition of the ion-sensitive membrane solution (Ca2+, K+, and Cl−) directly onto the mediating poly-EDOT (PEDOT), PEDOT–SSA, PEDOT–MES, PEDOT–MOPS, or poly-MPy–MOPS layers. 相似文献
18.
Pulse radiolysis of an aqueous solution of mono-valent thallium ion and mixed solutions of Tl+/Ag+ in the presence of various amino polycarboxylic acids such as trans-1,2-diaminocyclohexane-N,N,N′,N′-tetraacetic acid (DCTA), diethylenetriaminepentaacetic acid (DTPA), N-(2-hydroxyethyl)ethylenediaminetriacetic acid (HEDTA) and triethylenetetraminehexaacetic acid (TTHA) has been carried out.
Abnormal valence states of Tl ions were generated. It is concluded that DCTA, DTPA, HEDTA and TTHA decrease the redox potential
of Tl ions in aqueous solutions. It was observed that the electron transfer from complexed Tl2+ to Ag+ varied in the range 7.5 × 108 to 1.0 × 109, depending on the type of complexing ligand. Electron transfer from Tl2+ to Ag+ lead to the formation of silver atoms, which agglomerate further to form silver colloid. 相似文献
19.
Enantioseparations of racemic nonsteroidal anti-inflammatory drugs (naproxen, ibuprofen, ketoprofen, flurbiprofen, suprofen,
indoprofen, cicloprofen, and carprofen) were performed by nano-liquid chromatography, employing achiral capillary columns
and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CD) or hydroxylpropyl-β-cyclodextrin (HP-β-CD) as a chiral mobile phase additive (CMPA). Working
under the same experimental conditions (in terms of mobile phase and linear velocity), the performance of a RP-C18 monolithic
column was compared with that of a RP-C18 packed column of the same dimensions (100 μm i.d. × 10 cm). Utilizing a mobile phase
composed of 30% ACN (v/v) buffered with 50 mM sodium acetate at pH 3, and containing 30 mM TM-β-CD, the monolithic column
provided faster analysis but lower resolution than the packed column. This behavior was ascribed to the high permeability
of the monolithic column, as well as to its minor selectivity. HP-β-CD was chosen as an alternative to TM-β-CD. Employing
the monolithic column, the effects of different parameters such as HP-β-CD concentration, mobile phase composition, and pH
on the retention factor and the chiral resolution of the analytes were studied. For the most of the analytes, enantioresolution
(which ranged from R
s = 1.80 for naproxen to R
s = 0.86 for flurbiprofen) was obtained with a mobile phase consisting of sodium acetate buffer (25 mM, pH 3), 10% MeOH, and
15 mM HP-β-CD. When the same experimental conditions were used with the packed column, no compound eluted within 1 h. Upon
increasing the percentage of organic modifier to favor analyte elution, only suprofen eluted within 30 min, with an R
s value of 1.14 (20% MeOH). Replacing MeOH with ACN resulted in a loss of enantioresolution, except for naproxen (R
s = 0.89). 相似文献
20.
Manuel Snchez‐Chaves Gerardo Martínez Enrique Lpez Madruga Carmen Fernndez‐Monreal 《Journal of polymer science. Part A, Polymer chemistry》2002,40(8):1192-1199
Free‐radical copolymerization of glycidyl methacrylate (GMA) with N‐vinylpyrrolidone (VPD) was carried out at 50 °C using 3.0 mol · L?1 of N,N′‐dimethylformamide solution and 9.0 · 10?3 mol · L?1 of 2,2′‐azobisisobutyronitrile as an initiator. The modification reaction of GMA‐VPD copolymers with a model bioactive carboxylic acid, 6‐methoxy‐α‐methyl‐2‐naphthaleneacetic acid (naproxen), was studied in the homogeneous phase using basic catalysts. The influence of the type of catalyst and the GMA content was evaluated. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1192–1199, 2002 相似文献