CN108760950B - Method for determining nitrofuran metabolite - Google Patents
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Abstract
The invention discloses a method for determining nitrofuran metabolites, which comprises the derivation steps: taking a sample to be detected, adding an organic solution of dimethylamino naphthalene sulfonyl chloride, and heating in a water bath to obtain a derivative sample; and (3) filtering: filtering the derived sample to obtain an impurity-removed sample; the determination step comprises: and (4) performing liquid chromatography tandem mass spectrometry on the impurity-removed sample. According to the method for determining the nitrofuran metabolites, the sample to be detected is derived by using the dimethylamino naphthalene sulfonyl chloride, and the generated nitrofuran dimethylamino naphthalene sulfonamide compound after the derivation is not easy to hydrolyze and has good stability, so that the determination can be performed without using an internal standard compound, the detection cost is reduced, the detection time is shortened, and the efficiency is higher.
Description
Technical Field
The invention relates to the technical field of analytical chemistry, in particular to a method for determining nitrofuran metabolites.
Background
Nitrofurans belongs to one of veterinary drug residue detection items. Nitrofurans have a broad antimicrobial spectrum, a strong bactericidal ability, a good drug resistance and a low price, and have been widely used in the prevention and treatment of infectious diseases of livestock, poultry, pets, aquatic animals and other cultured animals, and as a feed additive for the prevention and treatment of gastrointestinal diseases of pigs, cattle, poultry and bees caused by salmonella and escherichia, and as a livestock growth promoter.
The nitrofurans raw medicine is metabolized quickly in the organism and has short half-life period, so that the nitrofurans raw medicine is metabolized quickly in the organism after being used by livestock and poultry, and is difficult to detect. The nitrofuran raw medicine mainly comprises furazolidone, furaltadone, nitrofurantoin and nitrofural, main metabolites of the nitrofuran raw medicine are respectively 3-amino-2-oxazolidinone, 3-amino-5-morpholinomethyl-2-oxazolidinone, 1-amino-hydantoin and semicarbazide, and the metabolites and proteins are combined stably and can remain in biological tissues for a long time, so the residual condition of the nitrofuran medicine can be reflected by utilizing the detection of the nitrofuran metabolite.
Research shows that nitrofurans have great harm to human body and are one kind of matter with potential carcinogenesis, teratogenesis and mutation induction. Therefore, the control of furan substances is very strict in all countries in the world, and all countries have clear regulations on monitoring standards.
At present, the main methods for detecting the 4 nitrofuran metabolites at home and abroad are liquid chromatography, liquid tandem mass spectrometry and the like. Among them, the tandem mass spectrometry is the most accurate and widely used detection method.
However, the existing liquid phase tandem mass spectrometry for detecting the furan metabolite has the following defects: during the determination, 2-nitrobenzaldehyde is adopted to derive 4 nitrofuran metabolites, and after derivation, an imine compound is generated, and then the determination is carried out. However, the generated imine compound is easy to hydrolyze and has poor stability, and an internal standard compound needs to be added, so that the detection cost is increased; meanwhile, the retention time of the sample after derivatization is not long, and the detection accuracy is influenced.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a method for measuring a nitrofuran metabolite, wherein a sample to be measured is derived by using dimethylamino naphthalene sulfonyl chloride, and a nitrofuran dimethylamino naphthalene sulfonamide compound generated after the derivation is not easy to hydrolyze and has good stability, so that an internal standard compound is not needed for measurement, the detection cost is reduced, the detection time is shortened, and the efficiency is higher.
The purpose of the invention is realized by adopting the following technical scheme:
a method of determining a nitrofuran metabolite, comprising:
and (3) a derivation step: taking a sample to be detected, adding an organic solution of dimethylamino naphthalene sulfonyl chloride, and heating in a water bath to obtain a derivative sample;
The determination step comprises: subjecting the derivatized sample to liquid chromatography tandem mass spectrometry.
Further, the method also comprises the following filtering steps: and filtering the derived sample to obtain an impurity-removed sample, and performing liquid chromatography tandem mass spectrometry on the impurity-removed sample.
Further, in the filtration step, the derivatized sample is filtered through a filter having a pore size of 0.2 to 0.8. mu.m.
Further, the pore size of the filter membrane is 0.45 μm.
Further, in the derivatization step, the organic solution of the dimethylamino naphthalenesulfonyl chloride is dimethylamino naphthalenesulfonyl chloride acetonitrile solution.
Further, in the derivatization step, 1-3mL of water sample to be tested is taken, 0.1-0.3mL of organic solution of dimethylamino naphthalene sulfonyl chloride is added, and the mixture is heated in a water bath at 80-100 ℃ for 50-70min to obtain a derivatization sample.
Further, the concentration of the organic solution of dimethylaminonaphthalenesulfonyl chloride is 10000 mg/L.
Further, in the measuring step, the measuring conditions of the liquid chromatography are: waters ACQUITYUPLC BEH C18Chromatography column, 50mm x 2.1mm,1.7 μm; the column temperature is 40 ℃; the sample volume is 1 mu L; the flow rate is 0.3 mL/min; gradient elution with 0.1% formic acid water solution as mobile phase A and methanol as mobile phase B;
The conditions for mass spectrometry were: scanning positive ions; capillary voltage 1.5 kV; the ion source temperature is 150 ℃; removing the solvent gas by 500 ℃; the flow rate of the desolventizing agent is 800L/h; the air flow of the air curtain is 50L/h; and (4) detecting in a multi-reaction monitoring mode.
Further, in the liquid chromatography determination, the procedure of gradient elution is as follows: 0-1min, 85% A; 1-2min, 85% A-15% A; 2-3-min, 15% A; 3-4min, 15% A-85% A; 4-5min, 85% A.
Further, the desolvation gas is nitrogen gas during mass spectrometry;
the nitrofuran metabolites include: 3-amino-2-oxazolidinyl ketones, 1-amino-hydantoin, semicarbazide, and 5-methylmorpholin-3-amino-2-oxazolidinyl ketones; wherein, the ion pair parameters of the 3-amino-2-oxazolidinyl ketone are 336/171 and 336/236, and the quantitative ion parameter is 336/171; ion pair parameters of 1-amino-hydantoin were 349/171, 349/236, quantitative ion parameter was 349/171; the ion pair parameters of the semicarbazide are 309/309 and 309/171, and the quantitative ion parameter is 309/171; ion pair parameters of 5-methylmorpholine-3-amino-2-oxazolidinyl ketone are 435/170, 435/234, 435/171, and quantitative ion parameter is 435/170.
Compared with the prior art, the invention has the beneficial effects that:
(1) The method for determining the nitrofuran metabolites firstly reports that 4 nitrofuran metabolites are determined by derivatization of the dimethylamino naphthalene sulfonyl chloride at home and abroad, and the nitrofuran dimethylamino naphthalene sulfonamide compound generated after derivatization is not easy to hydrolyze and has better stability than an imine compound, so that subsequent determination can be performed without using an internal standard compound, thereby reducing the detection cost, shortening the detection time and having higher efficiency.
(2) According to the method for determining the nitrofuran metabolite, the derivative of the nitrofuran metabolite has a good linear relation with the peak area within the mass concentration range of 10-500 mu g/L, and the correlation coefficient r of the derivative is greater than 0.9995; moreover, the detection limit is calculated to be 1 mug/L according to the detection limit of the method which is 10 times of the signal-to-noise ratio, the detection limit is low, and the sensitivity is high; meanwhile, the detection method has high recovery rate and good precision.
Drawings
FIG. 1 is a chromatogram of 4 nitrofuran metabolites as provided in example 1 of the present invention;
FIG. 2 shows the chemical formula of the derivatization process of 4 nitrofuran metabolites in example 1 of the present invention.
Detailed Description
The present invention will be further described with reference to the accompanying drawings and the detailed description, and it should be noted that any combination of the embodiments or technical features described below can be used to form a new embodiment without conflict.
A method of determining a nitrofuran metabolite, comprising:
and (3) a derivation step: taking a sample to be detected, adding an organic solution of dimethylamino naphthalene sulfonyl chloride, and heating in a water bath to obtain a derivative sample;
the determination step comprises: and (4) carrying out liquid chromatography tandem mass spectrometry on the derivative sample.
As a further embodiment, the method further comprises the step of filtering: and filtering the derivative sample to obtain an impurity-removed sample, and performing liquid chromatography tandem mass spectrometry on the impurity-removed sample.
As a further embodiment, in the filtration step, the derivatized sample is filtered through a filter having a pore size of 0.2 to 0.8. mu.m.
As a further embodiment, the pore size of the filter is 0.45. mu.m.
As a further embodiment, in the derivatizing step, the organic solution of dimethylaminonaphthalenesulfonyl chloride is a dimethylaminonaphthalenesulfonyl chloride acetonitrile solution.
As a further embodiment, in the derivatization step, 1-3mL of a water sample to be tested is taken, 0.1-0.3mL of an organic solution of dimethylamino naphthalene sulfonyl chloride is added, and the mixture is heated in a water bath at 80-100 ℃ for 50-70min to obtain a derivatization sample.
As a further embodiment, the concentration of the organic solution of dimethylaminonaphthalenesulfonyl chloride is 10000 mg/L.
As a further embodiment, in the measuring step, the measuring conditions of the liquid chromatography are: waters ACQUITY UPLC BEH C 18Chromatography column, 50mm x 2.1mm,1.7 μm; the column temperature is 40 ℃; the sample size is 1 mu L; the flow rate is 0.3 mL/min; gradient elution with 0.1% formic acid water solution as mobile phase A and methanol as mobile phase B;
the conditions for mass spectrometry were: scanning positive ions; the capillary voltage is 1.5 kV; the ion source temperature is 150 ℃; removing the solvent gas by 500 ℃; the flow rate of the desolventizing agent is 800L/h; the air flow of the air curtain is 50L/h; and (4) detecting in a multi-reaction monitoring mode.
As a further embodiment, the procedure for gradient elution in liquid chromatography assay is: 0-1min, 85% A; 1-2min, 85% A-15% A; 2-3-min, 15% A; 3-4min, 15% A-85% A; 4-5min, 85% A. (that is, the mobile phase is composed of 85% A and 15% B at 0-1 min; the mobile phase is composed of 85% A-15% A and 15% B-85% B at 1-2 min; the same principle holds for the rest of the periods.)
When mass spectrometry is carried out, the detection method adopts positive ion scanning, 0.1% formic acid aqueous solution and methanol are used as mobile phases, so that the formation of positive ions is facilitated, and the proportion of a low organic phase to a high organic phase is increased gradually during gradient elution, so that the elution of a substance to be detected is facilitated, and the good retention time is obtained.
In a further embodiment, the desolvation gas is nitrogen gas during mass spectrometry;
Nitrofuran metabolites include: 3-amino-2-oxazolidinyl ketones, 1-amino-hydantoin, semicarbazide, and 5-methylmorpholin-3-amino-2-oxazolidinyl ketones; wherein, the ion pair parameters of the 3-amino-2-oxazolidinyl ketone are 336/171 and 336/236, and the quantitative ion parameter is 336/171; ion pair parameters for 1-amino-hydantoin were 349/171, 349/236, quantitative ion parameters were 349/171; the ion pair parameters of the semicarbazide are 309/309 and 309/171, and the quantitative ion parameter is 309/171; ion pair parameters of 5-methylmorpholine-3-amino-2-oxazolidinyl ketone are 435/170, 435/234, 435/171, and quantitative ion parameter is 435/170.
According to the method for determining the nitrofuran metabolite provided by the embodiment of the invention, the sample to be detected is derived by using the dimethylamino naphthalene sulfonyl chloride, and the generated nitrofuran dimethylamino naphthalene sulfonamide compound after the derivation is not easy to hydrolyze and has better stability than an imine compound, so that subsequent determination can be performed without using an internal standard compound, the detection cost is reduced, meanwhile, the detection time of the method is shortened, and the efficiency is higher. In addition, the derivatives of the 4 kinds of nitrofuran metabolites have good linear relation with the peak area within the mass concentration range of 10-500 mug/L, and the correlation coefficients r are all larger than 0.9995; and the detection limit is calculated to be 1 mug/L according to the detection limit of the method which is 10 times of the signal-to-noise ratio, the detection limit is low, and the sensitivity is high; meanwhile, the detection method has high recovery rate and good precision.
The following are specific examples of the present invention, and raw materials, equipments and the like used in the following examples can be obtained by purchasing them unless otherwise specified.
Example 1:
a method of determining a nitrofuran metabolite, comprising:
and (3) a derivation step: taking 1mL of water sample to be detected, adding 0.1mL of 10000mg/L dimethylamino naphthalene sulfonyl chloride acetonitrile solution, and heating in a water bath at 100 ℃ for 60min to obtain a derivative sample (shown in figure 2, the derivative process of 4 nitrofuran metabolites);
and (3) filtering: filtering the derived sample by using a filter membrane with the aperture of 0.45 mu m to obtain an impurity-removed sample;
the determination step comprises: performing liquid chromatography tandem mass spectrometry on the impurity-removed sample;
liquid chromatography conditions Waters ACQUITY UPLC BEH C18Chromatography column, 50mm x 2.1mm,1.7 μm; the column temperature is 40 ℃; the sample volume is 1 mu L; the flow rate is 0.3 mL/min; mobile phase a was 0.1% formic acid in water and mobile phase B was methanol, gradient elution: 0-1min, 85% A; 1-2min, 85% A-15% A; 2-3-min, 15% A; 3-4min, 15% A-85% A; 4-5min, 85% A;
mass spectrum conditions, positive ion scanning; the capillary voltage is 1.5 kV; the ion source temperature is 150 ℃; removing the solvent gas by 500 ℃; the flow rate of desolventizing gas (nitrogen) is 800L/h; the air flow of the air curtain is 50L/h; multiple Reaction Monitoring (MRM) mode detection; ion pair parameters of 3-amino-2-oxazolidinyl ketone are 336/171, 336/236, quantitative ion parameter is 336/171; ion pair parameters of 1-amino-hydantoin were 349/171, 349/236, quantitative ion parameter was 349/171; the ion pair parameters of the semicarbazide are 309/309 and 309/171, and the quantitative ion parameter is 309/171; ion pair parameters of 5-methylmorpholine-3-amino-2-oxazolidinyl ketone are 435/170, 435/234, 435/171, and quantitative ion parameter is 435/170.
As shown in FIG. 1, the peak-forming effects of the 4 kinds of nitrofuran metabolites were found to be good in FIG. 1.
Example 2:
example 2 differs from example 1 in that:
in the derivation step, 2mL of water sample to be tested is added with 0.2mL of 10000mg/L dimethylamino naphthalene sulfonyl chloride acetonitrile solution and heated in a water bath at 90 ℃ for 50 min.
The rest is the same as in embodiment 1.
Example 3:
example 3 differs from example 1 in that: in the derivation step, 3mL of water sample to be tested is added with 0.3mL of 10000mg/L dimethylamino naphthalene sulfonyl chloride acetonitrile solution and heated in a water bath at 80 ℃ for 70 min.
The rest is the same as in embodiment 1.
Effect evaluation and Performance detection
1. Linear range and detection limit
Preparing 1.0mL of standard curve solutions of the nitrofuran metabolites of 5 mu g/L, 10 mu g/L, 20 mu g/L, 50 mu g/L and 100 mu g/L by using 10mg/L of standard solutions of the nitrofuran metabolites, adding 0.1mL of 10000mg/L of dimethylamino naphthalene sulfonyl chloride acetonitrile solution, and carrying out water bath in a water bath at 100 ℃ for 60 min; after derivatization, liquid chromatography tandem mass spectrometry was performed as described in example 1.
The result shows that the derivative of the nitrofuran metabolite has a good linear relation with the peak area within the mass concentration range of 10-500 mu g/L (detailed in the following table 1), and the correlation coefficient r of the derivative is greater than 0.9995. The detection limit is generally determined as the detection limit by a method, and the detection limit is calculated to be 1 mug/L according to the method detection limit which is 10 times of the signal-to-noise ratio.
TABLE 14 Linear equation for nitrofuran metabolites
| Linear equation of state | Coefficient of correlation | |
| 3-amino-2-oxazolidinyl ketones | y＝8026.27x+9852.27 | 0.9999 |
| 1-amino-hydantoins | y＝4935.22x+5986.29 | 0.9998 |
| Semicarbazide | y＝1765.17x+76.23 | 0.9999 |
| 5-methylmorpholin-3-amino-2-oxazolidinyl ketones | y＝3954.32x+1388.55 | 0.9996 |
2. Recovery and precision
The water quality samples which are determined to be free of nitrofuran metabolites are selected and divided into three groups.
Three groups of samples were added at three concentrations of 10. mu.g/L, 20. mu.g/L, and 50. mu.g/L, respectively, and the addition recovery rate experiments were performed according to the methods of examples 1 to 3, and the recovery rates were calculated.
The three concentrations were measured in parallel 3 times, and the relative standard deviation RSD was calculated, and the results of recovery and precision are shown in Table 2.
TABLE 2 recovery and precision experimental results
From the data in table 1, the method for measuring the nitrofuran metabolites provided by the embodiment of the present invention has high recovery rate and good precision, wherein the best test result obtained in example 1 is the best example.
The above embodiments are only preferred embodiments of the present invention, and the protection scope of the present invention is not limited thereby, and any insubstantial changes and substitutions made by those skilled in the art based on the present invention are within the protection scope of the present invention.
Claims (8)
1. A method of determining a nitrofuran metabolite, wherein said nitrofuran metabolite comprises: 3-amino-2-oxazolidinyl ketones, 1-amino-hydantoin, semicarbazide, and 5-methylmorpholin-3-amino-2-oxazolidinyl ketones; the method comprises the following steps:
and (3) a derivation step: taking a water sample to be detected, adding an organic solution of dimethylamino naphthalene sulfonyl chloride, and heating in a water bath to obtain a derivative sample;
the determination step comprises: subjecting the derivatized sample to liquid chromatography tandem mass spectrometry;
the measurement conditions of the liquid chromatography are as follows: waters ACQUITY UPLC BEH C18Chromatography column, 50mm × 2.1mm,1.7 μm; the column temperature is 40 ℃; sample size of 1 muL; the flow rate is 0.3 mL/min; gradient elution with 0.1% formic acid water solution as mobile phase A and methanol as mobile phase B; the procedure for the gradient elution was: 0-1min, 85% A; 1-2min, 85% A-15% A; 2-3-min, 15% A; 3-4min, 15% A-85% A; 4-5min, 85% A;
the conditions for mass spectrometry were: scanning positive ions; the capillary voltage is 1.5 kV; the ion source temperature is 150 ℃; removing the solvent gas by 500 ℃; the flow rate of the desolventizing agent is 800L/h; the air flow of the air curtain is 50L/h; and (4) detecting in a multi-reaction monitoring mode.
2. The method for measuring a nitrofuran metabolite according to claim 1, further comprising the step of filtering: and filtering the derivative sample to obtain an impurity-removed sample, and performing liquid chromatography tandem mass spectrometry on the impurity-removed sample.
3. The method for the determination of a nitrofuran metabolite according to claim 2, wherein, in the filtration step, the derivatized sample is filtered with a filter having a pore size of 0.2 to 0.8 μm.
4. The method for the determination of a nitrofuran metabolite according to claim 3, wherein the pore size of the filter is 0.45 μm.
5. The method for measuring a nitrofuran metabolite according to claim 1, wherein in the derivatizing step, the organic solution of dimethylaminonaphthalenesulfonyl chloride is a dimethylaminonaphthalenesulfonyl chloride acetonitrile solution.
6. The method for measuring a nitrofuran metabolite as claimed in claim 1, wherein in the derivatization step, 1-3mL of a water sample to be measured is taken, 0.1-0.3mL of an organic solution of dimethylaminonaphthalenesulfonyl chloride is added, and the mixture is heated in a water bath at 80-100 ℃ for 50-70min to obtain a derivatization sample.
7. The method for measuring a nitrofuran metabolite according to claim 6, wherein the concentration of the organic solution of dimethylaminonanaphthalenesulfonyl chloride is 10000 mg/L.
8. The method for measuring a nitrofuran metabolite according to claim 1, wherein the desolvation gas is nitrogen gas during mass spectrometry;
Ion pair parameters for 3-amino-2-oxazolidinyl ketones are 336/171, 336/236, quantitative ion parameters are 336/171; ion pair parameters for 1-amino-hydantoin were 349/171, 349/236, quantitative ion parameters were 349/171; the ion pair parameters of the semicarbazide are 309/309 and 309/171, and the quantitative ion parameter is 309/171; ion pair parameters of 5-methylmorpholin-3-amino-2-oxazolidinyl ketone were 435/170, 435/234, 435/171, quantitative ion parameter was 435/170.
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