CN108918745A - A kind of method of succinylcholine chloride and its metabolite in detection food - Google Patents
A kind of method of succinylcholine chloride and its metabolite in detection food Download PDFInfo
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Abstract
The invention discloses a kind of methods of succinylcholine chloride and its metabolite in detection food.This method uses reverse phase solid phase extraction-ultra performance liquid chromatography-mass spectrum/mass spectrometric hyphenated technique, establishes succinylcholine chloride and its accurate qualitative and quantitative analysis method of metabolite chlorination amber list choline in animal derived food.The method established provides the detection foundation of science for the emergency disposal of food safety public health emergency.
Description
Technical field
The invention belongs to detection technique fields.It is produced more particularly to succinylcholine chloride in a kind of detection food and its metabolism
The method of object.
Background technique
Succinylcholine chloride (Succinylcholine Chloride), also known as Suxamethonium Chloride, Scoline, department can
Woods, bis- [N, N, N- trimethyl the second ammoniums] two of the entitled dichloride 2,2 '-[(Isosorbide-5-Nitrae-dioxy-Isosorbide-5-Nitrae-butylidene) bis- (oxygen)] of chemistry are hydrated
Object, molecular formula are C14H30Cl2N2O4·2H2O.It is a kind of depolarising type muscle relaxant, can produce stable depolarization effect, draw
Play skeletal muscle relaxation.Mesostate chlorination succinyl list gallbladder can be hydrolyzed to by pseudocholinesterase in blood rapidly into internal
Alkali is one of the anaesthetic that the mankind have found earliest, belongs to B grades of organic toxic articles, country's one kind controlled drug.In recent years, it is some not
Method molecule is fabricated to dartlike weapon for stealing dog or poisoning and interferes them using the feature that succinylcholine chloride is rapid-action, toxicity is big
The dog of crime, due in the dog body poisoned with poison can residual chloride succinylcholine if having eaten these dog meats just have food peace
Full hidden danger.
Mainly there are fluorescence spectrophotometry, the chromatography of ions, infrared light to the detection method of succinylcholine chloride at present
Spectrometry, chemical colour reaction reaction method, titration, liquid chromatography and mass spectrography.These methods are largely for chlorination succinyl
Choline raw drug analysis, has certain limitation.Because succinylcholine chloride content is very high in raw medicine, the sensitivity to method
It is required with detection limit not high.And it is animal derived it is necessary to consider to detect succinylcholine chloride residual quantity in animal derived food
The complexity of food substrate, it is relatively just very high to the requirement of its separation and concentration, but there are complex pretreatments for existing method, quantitatively not
Succinylcholine chloride can be metabolized as chlorination succinylcholine in vivo in the problems such as accurate, especially animal derived food,
Therefore existing method is not able to satisfy the testing requirements of succinylcholine chloride and its metabolite trace in animal derived food,
Therefore it is badly in need of establishing the detection technique of succinylcholine chloride and its metabolite in a kind of animal derived food.
Summary of the invention
The purpose of the present invention is intended to the shortcomings that overcoming existing succinylcholine chloride detection technique, establishes a kind of animal derived
The detection technique of succinylcholine chloride and its metabolite in food.This method is food safety public health emergency
Emergency disposal provides the detection foundation of science.
In order to achieve the above objectives, the present invention adopts the following technical solutions：
The present invention provides a kind of method of succinylcholine chloride and its metabolite in detection food, and this method includes：
1) sample pre-treatments
It weighs homogeneous sample to be placed in centrifuge tube, according to 1g:20-50μL:1-2mL:25 μ g/mL are added in the ratio of 1-2mL
Paraoxon working solution, 0.1mol/L hydrochloric acid and Extraction buffer, mix through tissue refiner, then vortex mixing, temperature are lower than 4 DEG C
Under the conditions of be centrifuged, take supernatant, it is to be clean, wherein the Extraction buffer be 25mmol/L ammonium formate 40mmol/L HFBA water
Solution, ammonium hydroxide tune pH to 3.0；
It takes on the reverse phase solid phase extraction column of the supernatant load after activation, elutes extraction column with leacheate, sufficiently take out
It after dry, is eluted with methanol, collects eluent, it is 1 with volume ratio that eluent, which is blown to nitrogen at 45 DEG C or less and is closely done,:64-59:
The formic acid of 35-40:Acetonitrile:Aqueous dissolution residue is analyzed after filtering for UPLC-MS/MS, wherein the leacheate is
5mmol/L ammonium formate 5mmol/L HFBA aqueous solution, formic acid tune pH to 3.0；
2) it measures：
The drafting of a standard working curve
It weighs succinylcholine chloride and chlorination amber list choline standard items is made into standard solution, then take appropriate described
Standard solution is configured to the standard working solution of series of concentrations with blank sample matrix solution, analyzes through UPLC-MS/MS, with fixed
Amount ion peak areas is ordinate, and concentration is that abscissa draws standard working curve, obtains standard working curve regression equation；Its
In, the blank sample matrix solution is the sample without the succinylcholine chloride and its metabolite surveyed, through above-mentioned
Resulting solution after step 1) processing；
B chromatographic condition
Chromatographic column is Acquity UPLC BEH HILIC, and mobile phase is acetonitrile (A) and 0.1% formic acid 5mmol/L formic acid
Aqueous ammonium (B) is shown in Table 1 using gradient elution mode, and 35 DEG C of column temperature；
1 gradient elution program of table
C Mass Spectrometry Conditions
Ion source is electric spray ion source, using positive ionization mode, polyion reaction monitoring, capillary voltage：1.5kV；
Ion source temperature：150℃；Desolvation temperature：500℃；Desolventizing gas flow：900L/h；Cone hole backflow airflow amount：150L/
h；Succinylcholine chloride and its metabolite chlorination amber list choline is qualitative, quota ion and collision energy are shown in Table 2；
2 Choline Chloride Succinate of table and its main mass spectrometry parameters of metabolite
Note：Band * is quota ion
D is quantitatively and/or qualitatively measured.
Further, in the above method, it is 1-2 that the activation method of reverse phase solid phase extraction column, which is with volume ratio,:1 methanol and
The mixed solution of Extraction buffer is activated.
Further, reverse phase solid phase extraction column is 33 μm of polymeric of Strata-X.
Further, quantitative determination is specially：The sample solution injection UPLC-MS/MS that step 1) obtains is measured,
The chromatographic peak area for measuring target compound in sample liquid calculates chlorination succinyl gallbladder in sample solution according to standard working curve
The concentration of alkali and its metabolite chlorination amber list choline, is calculated from the formula succinylcholine chloride and its metabolism in sample
The content of product chlorinated amber list choline.
Further, qualitative determination is specially：Detecting step 1) target compound in obtained sample liquid, with retention time and
Characteristic ion carries out qualitative with chromatographic peak area relative abundance corresponding to quota ion.It is required that target compound in tested sample
Retention time and standard working solution in target compound retention time relative deviation less than 20%；Sample characteristic ion
The relative abundance of relative abundance mixed standard solution suitable with concentration is consistent, and relative abundance deviation is no more than the regulation of table 3, then may be used
There are corresponding measured objects in judgement sample.
With respect to the maximum allowable offset of abundance of ions when 3 qualitative determination of table
Further, in step 1), using 0.22 μm of organic filter membrane when filtering.
Present invention employs 25 μ g/mL paraoxon working solutions, 0.1mol/ that specific quantity is added in the sample in the above method
The mode that L hydrochloric acid, Extraction buffer extract sample.For example, according to 1g:20μL:1mL:25 μ g/ are added in the ratio of 1mL
ML paraoxon working solution, 0.1mol/L hydrochloric acid and Extraction buffer；According to 1g:30μL:1mL:25 μ g/mL are added in the ratio of 1mL
Paraoxon working solution, 0.1mol/L hydrochloric acid and Extraction buffer；According to 1g:40μL:1mL:25 μ g/mL couple are added in the ratio of 1mL
Oxygen phosphorus working solution, 0.1mol/L hydrochloric acid and Extraction buffer；According to 1g:50μL:2mL:25 μ g/mL are added to oxygen in the ratio of 2mL
Phosphorus working solution, 0.1mol/L hydrochloric acid and Extraction buffer etc..Because by testing choline in discovery meat to blank dog meats mark-on
Esterase can persistently digest target compound, to cause the target compound detection rate of recovery very low, paraoxon is added can be effective
Inhibit the enzymatic hydrolysis of succinylcholine chloride.Since succinylcholine chloride can exist in acid medium with cationic form, have
Conducive to extracting and purify, therefore acidification Extraction buffer is used to extract it.It, can be effective simultaneously by the way of refrigerated centrifuge
Remove the albumen and fat in animal derived food.
Present invention employs reverse phase solid phase extraction column purification technologies in the above method.Due to the composition ten of animal derived food
Divide complexity, especially contains high protein, high-fat ingredient, the detection of severe jamming test substance, it is solid that present invention employs reverse phases
Phase extraction column purification techniques, to have the function that sample purification.Matrix interference is not only effectively removed, but also target compound is equal
There is the higher rate of recovery.
The present invention uses formic acid in the above method：Acetonitrile：Water (1:64-59:35-40) solution dissolved residue is because multiple
Solvent watr-proportion influences less chlorination succinylcholine, but when watr-proportion reaches 60%, response intensity is obvious
Decline；Solvent watr-proportion is redissolved to be affected to succinylcholine chloride, as watr-proportion increases, succinylcholine chloride
Response intensity is remarkably reinforced, but considers chromatographic column solvent effect, and watr-proportion should not be too large, therefore uses formic acid：Acetonitrile：Water
(1:64-59:35-40) solution dissolved residue, in some embodiments of the present invention, such as with volume ratio be 1:59:40
Formic acid:Acetonitrile:Aqueous dissolution residue；It is 1 with volume ratio:62:37 formic acid:Acetonitrile:Aqueous dissolution residue etc..
The present invention draws standard working curve using standard working solution in the above method.Due to consideration that this method is external standard
Method and sample substrate effect, while in view of due to that may contain in succinylcholine chloride and its metabolite residue influence and dog meats
There is its metabolite, so being configured to hybrid standard using the target compound to blank sample matrix solution addition various concentration
Working solution overcomes the matrix effect of some samples, improves qualitative, quantitative accuracy and reliability.
The influence that different flow visualizings separate target compound is investigated, research shows that using 0.1% formic acid acetonitrile
When solution and 0.1% formic acid 5mmol/L formic acid aqueous ammonium are as mobile phase, isolated effect is very bad, and use acetonitrile and
When 0.1% formic acid 5mmol/L formic acid aqueous ammonium is as mobile phase, succinylcholine chloride and its metabolite can be good at
It is separated.According to the physicochemical property of succinylcholine chloride and its metabolin, positive ionization mode, polyion reaction prison are used
It surveys, it is ensured that fast qualitative, it is precisely quantitative.
Beneficial effects of the present invention are as follows：
The present invention establishes reverse phase solid phase extraction-ultra performance liquid chromatography-matter by the optimization to experiment condition for the first time
The side of succinylcholine chloride and its metabolin chlorination amber list choline residual quantity in spectrum/mass spectrometric determination animal derived food
Method.After sample extracts refrigerated centrifuge using acidity HFBA solution, supernatant crosses reverse phase solid phase extraction column purification, effectively overcomes
Matrix interference and reduce loss caused by sample pre-treatments, it is ensured that the accuracy of qualitative and quantitative analysis result.Chlorination amber
The concentration of amber phatidylcholine and chlorination amber list choline is linear good within the scope of 1.5 μ g/L-15 μ g/L.In a tool of the invention
In body embodiment, as sampling amount 5.0g, constant volume 1.0mL, the detection of succinylcholine chloride and chlorination amber list choline
It is limited to 0.2 μ g/kg, is quantitatively limited to 0.6 μ g/kg.Method average recovery rate in 92.3%-103.6%, RSD is 2.5%~
6.9%.Sample pre-treatments of the present invention are simple, and extraction efficiency is relatively high, good separating effect, favorable reproducibility, the sensitivity of method and
Detection limit is able to satisfy the requirement of poisonous substance retention analysis, and use easy to spread.The present invention only needs 5 minutes just to complete whole points
From detection, can fast qualitative, detection efficiency is improved, so that the present invention is more suitable for the detection of public health emergency.
Detailed description of the invention
The standard chromatogram of Fig. 1 Choline Chloride Succinate and its metabolite.
Fig. 2 blank sample chromatogram.
Fig. 3 positive sample succinylcholine chloride and chlorination amber list choline chromatogram.
Specific embodiment
Instrument and reagent used in the embodiment of the present invention：
Ultra performance liquid chromatography-tandem mass spectrum combined instrument (UPLC-MS/MS) (Waters TQS, the U.S.), refrigerated centrifuge
(CF16RN, Hitachi, Ltd), MS3 type eddy mixer (IKA, Germany), nitrogen evaporator (OA.SYS, OA.JNC), acidometer
(FE20, METTLER), solid-phase extracting instrument；Succinylcholine chloride and its metabolite chlorination amber list choline standard items, are purchased
From German Dr.Ehrenstorfer company, purity is >=99.0%；(chromatographically pure, U.S. Fisher are public for methanol, acetonitrile, formic acid
Department)；Ammonium formate (chromatographically pure, German CNW company)；Ammonium hydroxide, hyptafluorobutyric acid (HFBA), hydrochloric acid (excellent pure grade, northization)；Strata-X
33 μm of polymeric reverse phase solid phase extraction columns：The equivalent column of 200mg/3mL or other.
Leacheate：5mmol/L ammonium formate 5mmol/L HFBA aqueous solution, formic acid tune pH to 3.0.0.0315g is weighed respectively
Ammonium formate and 0.107g HFBA pure water are settled to 100.0mL, then with first acid for adjusting pH to 3.0.
Extraction buffer：25mmol/L ammonium formate 40mmol/L HFBA aqueous solution, ammonium hydroxide tune pH to 3.0.It weighs respectively
0.158g ammonium formate and 0.856g HFBA pure water are settled to 100.0mL, then adjust pH to 3.0 with ammonium hydroxide.
The detection of succinylcholine chloride and its metabolite chlorination amber list choline residual quantity in 1 dog meats of embodiment
1) sample pre-treatments
Homogeneous sample 5g (being accurate to 0.01g) is weighed, is placed in 50mL polypropylene centrifuge tube, 100 μ L, 25 μ g/mL is added
Paraoxon working solution, 5mL 0.1mol/L hydrochloric acid, 5mL Extraction buffer, the vortex mixing 10min after tissue refiner mixes
Afterwards, 10000r/min is centrifuged 10min (temperature is lower than 4 DEG C), takes supernatant, to be clean.
6mL methanol and 3mL Extraction buffer activated solid extraction column are first used, then takes the load of 5mL supernatant in Solid Phase Extraction
On column, pillar is eluted with 4mL leacheate, after sufficiently draining, is eluted with 4mL methanol, collects eluent, eluent is at 45 DEG C or less
It is blown to nitrogen and is closely done, with 1mL formic acid：Acetonitrile：Water (1:59:40) solution dissolved residue crosses 0.22 μm of organic phase filter membrane filtering
(spectrogram is shown in Fig. 1, Fig. 2 and Fig. 3) is analyzed for LC-MS/MS afterwards.
2) standard solution is prepared
Standard reserving solution：0.0100g succinylcholine chloride and chlorination amber list choline standard items are accurately weighed respectively, are used
Pure water is settled to 10.0mL, is configured to the standard reserving solution that concentration is 1mg/mL, saves in -20 DEG C of refrigerators, validity period 12 months.
Standard solution：Each 1mL of standard reserving solution is taken respectively, is settled to 100.0mL with acetonitrile, is made into hybrid standard use
Liquid, each component concentration are 10 μ g/mL.4 DEG C of this standard solution preservations, validity period 3 months.
3) it measures：
The drafting of a standard working curve
Standard solution is configured to 1.5,3.0,6.0,9.0,12.0,15.0ng/mL series with blank sample extracting solution
Standard working solution.It is analyzed through UPLC-MS/MS, using quota ion peak area as ordinate, concentration is that abscissa draws standard work
Curve obtains standard working curve regression equation.
B chromatographic condition
Chromatographic column is Acquity UPLC BEH HILIC (2.1mm × 100mm, 1.7 μm, Waters, US)；Stream
Dynamic is mutually -0.1% formic acid 5mmol/L formic acid aqueous ammonium of acetonitrile, and flow velocity 0.3mL/min is shown in Table using gradient elution mode
1, total run time 5.5min；35 DEG C of column temperature, 2 μ L of sample volume.
C Mass Spectrometry Conditions
Ion source is electric spray ion source, positive ion mode, polyion reaction monitoring, capillary voltage：1.5kV；Ion
Source temperature：150℃；Desolvation temperature：500℃；Desolventizing gas flow：900L/h；Cone hole backflow airflow amount：150L/h.Chlorine
Change succinylcholine and the qualitative of chlorination amber list choline, quota ion and collision energy, orifice potential are shown in Table 4.
4 succinylcholine chloride of table and the qualitative of chlorination amber list choline, quota ion and collision energy
4) it calculates
Choline Chloride Succinate and its metabolite residual quantity are calculated by formula (1) in sample.
In formula：
X --- the content of succinylcholine chloride and chlorination amber list choline in sample, unit are ng/kg, μ g/
kg；
C --- the concentration of component to be measured in measurement liquid, unit is nanograms per milliliter, ng/mL；
V --- constant volume, unit are milliliter, mL；
M --- sample sample weighting amount, unit be gram, g；
10 --- it is sample extracting solution volume, mL；
5 --- volume, mL are measured for sample.
According to standard working curve, the concentration of succinylcholine chloride and chlorination amber list choline in sample solution is calculated,
It is calculated from the formula the content of succinylcholine chloride and chlorination amber list choline in sample.
Embodiment 2
The succinylcholine chloride and chlorination amber list choline standard series that various concentration is prepared with vehicle solution, are adopted
It is analyzed with UPLC-MS/MS, obtains the range of linearity, regression equation and related coefficient (r) and detection limit.By the method for the present invention
Sample treatment is carried out, the 3 horizontal succinylcholine chlorides and chlorination amber list choline of different content are added in matrix sample
Mixed standard solution, each addition concentration is measured in parallel 6 times, measures precision and accuracy.
1) range of linearity, regression equation, detection limit and quantitative limit
The concentration of succinylcholine chloride and chlorination amber list choline is linear good within the scope of 1.5 μ g/L-15 μ g/L.When
When sampling amount 5.0g, constant volume 1.0mL, the detection of succinylcholine chloride and chlorination amber list choline is limited to 0.2 μ g/kg,
Quantitatively it is limited to 0.6 μ g/kg.See Table 5 for details.
5 succinylcholine chloride of table and the chlorination amber list choline range of linearity and detection limit
2) preci-sion and accuracy is tested
The mixing of the 3 horizontal succinylcholine chlorides and chlorination amber list choline of different content is added in matrix sample
Standard solution, each addition concentration are measured in parallel 6 times, measure precision and accuracy, succinylcholine chloride and chlorination amber
For single choline recovery of standard addition in 92.3%-103.6%, the RSD measured is 2.5%-6.9%.The accuracy and precision of method
Degree is able to satisfy the requirement of sitotoxismus object retention analysis (see Table 6 for details).
6 succinylcholine chloride of table and chlorination amber list choline preci-sion and accuracy test result (n=6)
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention may be used also on the basis of the above description for those of ordinary skill in the art
To make other variations or changes in different ways, all embodiments can not be exhaustive here, it is all to belong to this hair
The obvious changes or variations that bright technical solution is extended out are still in the scope of protection of the present invention.
Claims (6)
1. a kind of method of succinylcholine chloride and its metabolite in detection food, which is characterized in that this method includes：
1) sample pre-treatments
It weighs homogeneous sample to be placed in centrifuge tube, according to 1g:20-50μL:1-2mL:25 μ g/mL are added to oxygen in the ratio of 1-2mL
Phosphorus working solution, 0.1mol/L hydrochloric acid and Extraction buffer, mix through tissue refiner, then vortex mixing, temperature are lower than 4 DEG C of conditions
Lower centrifugation, takes supernatant, to be clean, wherein the Extraction buffer is that 25mmol/L ammonium formate 40mmol/L HFBA is water-soluble
Liquid, ammonium hydroxide tune pH to 3.0；
It takes on the reverse phase solid phase extraction column of the supernatant load after activation, elutes extraction column with leacheate, after sufficiently draining,
It is eluted with methanol, collects eluent, it is 1 with volume ratio that eluent, which is blown to nitrogen at 45 DEG C or less and is closely done,:64-59:35-40
Formic acid:Acetonitrile:Aqueous dissolution residue is analyzed after filtering for UPLC-MS/MS, wherein the leacheate is 5mmol/L first
Sour ammonium 5mmol/L HFBA aqueous solution, formic acid tune pH to 3.0；
2) it measures：
The drafting of a standard working curve
It weighs succinylcholine chloride and chlorination amber list choline standard items is made into standard solution, then take the appropriate standard
The standard working solution of series of concentrations is configured to blank sample matrix solution using liquid, is analyzed through UPLC-MS/MS, with it is quantitative from
Sub- peak area is ordinate, and concentration is that abscissa draws standard working curve, obtains standard working curve regression equation；
B chromatographic condition
Chromatographic column is Acquity UPLC BEH HILIC, and mobile phase is that acetonitrile A and 0.1% formic acid 5mmol/L ammonium formate are water-soluble
Liquid B, using gradient elution mode, 35 DEG C of column temperature；
C Mass Spectrometry Conditions
Ion source is electric spray ion source, using positive ionization mode, polyion reaction monitoring, capillary voltage：1.5kV；Ion
Source temperature：150℃；Desolvation temperature：500℃；Desolventizing gas flow：900L/h；Cone hole backflow airflow amount：150L/h；
D is quantitatively and/or qualitatively measured.
2. the method according to claim 1, wherein the activation method of reverse phase solid phase extraction column is to be with volume ratio
1-2:1 methanol and the mixed solution of Extraction buffer are activated.
3. the method according to claim 1, wherein reverse phase solid phase extraction column is 33 μm of Strata-X
polymeric。
4. the method according to claim 1, wherein quantitative determination is specially：The sample that step 1) is obtained is molten
Liquid injection UPLC-MS/MS is measured, and measures the chromatographic peak area of target compound in sample liquid, according to standard working curve, meter
The concentration of succinylcholine chloride and its metabolite chlorination amber list choline in sample solution is calculated, sample is calculated from the formula
The content of middle succinylcholine chloride and its metabolite chlorination amber list choline.
5. the method according to claim 1, wherein qualitative determination is specially：Detecting step 1) obtained sample liquid
Middle target compound is determined with chromatographic peak area relative abundance corresponding to retention time and characteristic ion and quota ion
Property.
6. the method according to claim 1, wherein in step 1), using 0.22 μm of organic filter membrane when filtering.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111060490A (en) * | 2019-12-25 | 2020-04-24 | 安徽中科赛飞尔科技有限公司 | SERS detection method of succinylcholine chloride |
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| JP2002223794A (en) * | 1998-12-02 | 2002-08-13 | Azwell Inc | Method for measuring activity of platelet activating factor acetyl hydrolase |
| US20100221756A1 (en) * | 2007-09-11 | 2010-09-02 | Buhlmann Laboratories Ag | Allergy test based on flow cytometric analysis |
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