Preparation of stable isotope-labeled 2-nitrobenzaldehyde derivatives of four metabolites of nitrofuran antibiotics and their comprehensive characterization by UV, MS, and NMR techniques.

doi:10.1021/JF034536Q

Paper

Preparation of stable isotope-labeled 2-nitrobenzaldehyde derivatives of four metabolites of nitrofuran antibiotics and their comprehensive characterization by UV, MS, and NMR techniques.

Published Sep 18, 2003 · T. Delatour, E. Gremaud, P. Mottier

Journal of agricultural and food chemistry

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19

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Abstract

A convenient method is presented for the preparation of the carbon-13-labeled 2-nitrobenzaldehyde derivatives of the nitrofuran metabolites 3-amino-2-oxazolidinone (AOZ), semicarbazide (SC), 1-aminohydantoin (AH), and 3-amino-5-morpholinomethyl-2-oxazolidinone (AMOZ), with the purpose of using them as internal standards for the quantification of trace levels of nitrofuran residues by liquid chromatography-tandem mass spectrometry in foods of animal origin. The synthesis encompasses the nitration of [1,2,3,4,5,6-(13)C(6)]toluene prior to chromyl compound-mediated oxidation of the methyl group into the corresponding aldehyde. The four metabolites of nitrofuran antibiotics were derivatized independently with the resulting ring-labeled 2-nitrobenzaldehyde (NBA) to obtain the target compounds. Both the isotopically enriched and native substances were used to perform a comprehensive fragmentation study by electrospray ionization (ESI) collision-induced dissociation (CID) mass spectrometry (MS). Full characterization of the nitrofuran derivatives was accomplished with ultraviolet (UV) and exhaustive nuclear magnetic resonance (NMR) analysis. A major advantage of the described procedure is that it can be extended to the preparation of other carbon-13-labeled derivatives of metabolites of nitrofuran antibiotics.

Study Snapshot

This study presents a method for preparing carbon-13-labeled 2-nitrobenzaldehyde derivatives of nitrofuran metabolites, which can be used as internal standards for quantifying trace levels of nitrofuran residues in foods of animal origin.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Preparation of stable isotope-labeled 2-nitrobenzaldehyde derivatives of four metabolites of nitrofuran antibiotics and their comprehensive characterization by UV, MS, and NMR techniques.

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References

Citations

Determination of four nitrofuran metabolites in gelatin Chinese medicine using dispersive solid phase extraction and pass-through solid phase extraction coupled to ultra high performance liquid chromatography-tandem mass spectrometry.

The study developed a validated analytical method for detecting and quantifying nitrofuran metabolites in gelatin Chinese medicine, with a limit of detection of 0.2 g/kg and a quantification limit of 0.6 g/kg.

Determination of nitrofuran metabolites in shrimp muscle by liquid chromatography-photo diode array detection

This HPLC-DAD method effectively detects nitrofuran metabolites in shrimp muscle tissue, meeting EU requirements for food exports.

On the Extraction of Antibiotics from Shrimps Prior to Chromatographic Analysis

Different extraction methods for antibiotics from shrimps have been developed, aiming to monitor residue levels for routine regulatory analysis.

An optimized method for the accurate determination of nitrofurans in chicken meat using isotope dilution–liquid chromatography/mass spectrometry

The optimized method using isotope dilution-liquid chromatography/tandem mass spectrometry accurately determines low-level metabolite residues of nitrofuran antibiotics in chicken meat, providing reliable reference values for quality control in general testing laboratories.

Determination of nitrofuran and chloramphenicol residues by high resolution mass spectrometry versus tandem quadrupole mass spectrometry.

This study developed a UHPLC-HRMS method for detecting and quantifying nitrofuran and chloramphenicol residues in various animal-based food products, with validation for muscle, liver, kidney, fish, honey, eggs, and milk.

Determination of Nitrofurans Residue in Fishery Products Using High Performance Liquid Chromatography

This study developed a sensitive HPLC method to detect nitrofurans residue in fishery products, improving the safety of commercial fishery products in China.

Development of molecularly imprinted polymers for the binding of nitrofurantoin.

Molecularly imprinted polymers effectively recognize nitrofurantoin, with binding constants 630+/-104 and 830+/-146 M(-1), with cross reactivity determined by hydrogen bonds to the functional monomer.

Limits of suspicion, recognition and confirmation as concepts that account for the confirmation transitions at the detection limit for quantification by liquid chromatography-tandem mass spectrometry.

The limit of detection (LOD) in liquid chromatography-tandem mass spectrometry can be split into three concepts: limit of suspicion (LOS), recognition (LOR), and confirmation (LOC), with applications and drawbacks.

Determination of nitrofurans in animal feeds by liquid chromatography-UV photodiode array detection and liquid chromatography-ionspray tandem mass spectrometry.

This method effectively detects and confirms very low concentrations of nitrofurans in animal feed, potentially preventing nitrofuran residues in meat and other edible products.