CN106770765A - The detection method and application of a kind of albendazole and its metabolin - Google Patents
The detection method and application of a kind of albendazole and its metabolin Download PDFInfo
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- CN106770765A CN106770765A CN201611193712.5A CN201611193712A CN106770765A CN 106770765 A CN106770765 A CN 106770765A CN 201611193712 A CN201611193712 A CN 201611193712A CN 106770765 A CN106770765 A CN 106770765A
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Abstract
The invention discloses a kind of detection method for detecting albendazole and its metabolin, belong to drug measurement techniques field.The detection method of the albendazole and its metabolin is to utilize 2,6 BHTs and NaOH to extract albendazole and its metabolin in sample, is detected using high performance liquid chromatography GC-MS afterwards；Described 2, the concentration of 6 BHTs is 1%；The concentration of the NaOH solution is 50%.The beneficial effects of the invention are as follows：This method is not only applicable to animal muscle, applies also for the detection of the complex matrices such as liver, and reagent toxicity used in the present invention is small, low cost, saves the time, moreover it is possible to efficiently reduce the extraction to impurity, simplifies purifying step；Detected using high performance liquid chromatography tandem mass spectrum method, high with sensitivity compared to single high performance liquid chromatography, reproducible, the low advantage of test limit.
Description
Technical field
The invention belongs to drug measurement techniques field, and in particular to the detection method of a kind of albendazole and its metabolin and
Using.
Background technology
At present, using big solvents of toxicity such as ether, acetonitriles in the method for detection albendazole, or acetonitrile is directly used
Extract, these methods not only make sample extraction insufficient, and target compound is easily destroyed in extraction process, so that
Influence quantitative result.
The content of the invention
In order to solve the problems of the prior art, the present invention is adopted the technical scheme that：
The detection method of a kind of albendazole and its metabolin, sample is extracted using BHT and NaOH
In albendazole and its metabolin, detected using high performance liquid chromatography GC-MS afterwards；2, the 6- di-t-butyls pair
The concentration of cresols is 1%；The concentration of the NaOH solution is 50%.
On the basis of such scheme, the detection method step of the albendazole and its metabolin is as follows：
1) extraction purification
Sample 5.00g is weighed, 5mL water, 150 μ L 50%NaOH solution and 1mL 1%2,6- di-t-butyl is added to first
Phenol, vortex mixed adds 20mL ethyl acetate, and vibration 1min ultrasonic extractions 20min, 4000r/min centrifugation 5min takes supernatant
Liquid, to adding 10mL ethyl acetate to repeat to extract once in residue, in pear shape bottle, 40 DEG C of revolvings are extremely to merge supernatant twice
It is dry；To 6mL acetonitrile saturation n-hexanes are added in the pear shape bottle after being spin-dried for, vibration is mixed, poured into centrifuge tube, then in pear shape bottle
2mL acetonitriles are added, is poured into centrifuge tube in the lump after the ultrasound that is vortexed 1min, the hydrochloric acid of 6mL 0.1mol/L is molten to being added in centrifuge tube
Liquid, vortex 2min, 4000r/min centrifugation 5min, removes n-hexane layer, standby；If emulsification, ultrasound and with suction pipe stir after from
The heart；
2) column purification is purified
After activating PCX solid-phase extraction columns with 5mL methyl alcohol and 5mL water balances, take extract solution and cross PCX decontaminating columns, 3mL is used respectively
Water and 3mL methyl alcohol drip washing, then with 15mL volumetric concentrations for 5% ammoniacal liquor methanol solution is eluted, the eluent of reception is in 40 DEG C of rotations
Steam to after doing；1mL methyl alcohol and 1mL water are separately added into, are vortexed, cross 0.22 μm of nylon leaching film, it is to be measured；
3) high performance liquid chromatography GC-MS detection
Mass spectrometry parameters：Ion gun AJS ESI sources；Gas Temp：325℃；Gas Flow：10L/min；Sheath Gas
Temp350℃；Sheath Gas flow：11L/min；
Liquid phase parameter：A is 0.1% aqueous formic acid, and B is methyl alcohol.
On the basis of such scheme, the detection method of the albendazole and its metabolin is applied to detect animal derived
Albendazole and its metabolin in food.
On the basis of such scheme, the animal derived food is muscle, eggs, newborn class, liver and kidney.
Beneficial effects of the present invention：
Extract albendazole and its metabolin with BHT and NaOH in the inventive method, toxicity compared with
It is small；Additionally, albendazole and its metabolin in aqueous in alkalescence, add mass concentration for the 50%NaOH aqueous solution can make Ah
Parbendazole and its metabolin are extracted into molecular state beneficial to organic reagent；Addition mass concentration is 1%2,6- di-t-butyls to first
Phenol can protect albendazole not oxidized；Ethyl acetate is the organic reagent of low pole, and its addition is conducive to albendazole
Extract and impurity extract lack；Acetonitrile saturation n-hexane is used for removing the grease type impurity in sample, adds hydrochloric acid to make acetysalicylic acid phenobarbital
PCX is conducive to purify column purification into ionic condition up to azoles；5% ammoniacal liquor methyl alcohol is in strong basicity, can be adsorbed PCX decontaminating columns during wash-out
Albendazole replace.
Method of the present invention detection range is wider, and compared to the single-matrix of other method, this method is not only applicable to
Animal muscle and be also applied for the detection of the complex matrices such as liver, it is well known that animal's liver contain many albumen, fat,
Carbohydrate, vitamin and mineral matter, purification is not reclaimed totally on target compound influences very big；The method of the present invention uses 2,6- bis-
Butylated Hydroxytoluene, NaOH and ethyl acetate save the time as extract solution, small toxicity, low cost, and it is right to efficiently reduce again
The extraction of impurity, simplifies purifying step；This method uses Agilent PCX solid phase extraction columns, it is also possible to domestic PCX pillars generation
Replace, effectively reduce testing cost；Detected using high performance liquid chromatography-tandem mass method, compared to single efficient liquid phase
Chromatogram, reproducible, test limit low advantage high with sensitivity.
Brief description of the drawings
The measure of Fig. 1 albendazole -2- amino sulfone retention times, wherein ordinate are response, and abscissa is retention time.
Fig. 2 albendazole -2- amino sulfone quantitative and qualitatives ion is detailed, and wherein ordinate is response, when abscissa is to retain
Between.
Fig. 3 albendazole -2- amino sulfone mass spectrograms, wherein ordinate are response, and abscissa is m/z.
The measure of Fig. 4 albendazole-sulfoxide retention times, wherein ordinate are response, and abscissa is retention time.
Fig. 5 albendazole-sulfoxide quantitative and qualitatives ion is detailed, and wherein ordinate is response, and abscissa is retention time.
Fig. 6 albendazole-sulfoxide mass spectrograms, wherein ordinate are response, and abscissa is m/z.
The measure of Fig. 7 Albendazole sulfone retention times, wherein ordinate are response, and abscissa is retention time.
Fig. 8 Albendazole sulfone quantitative and qualitatives ion is detailed, and wherein ordinate is response, and abscissa is retention time.
Fig. 9 Albendazole sulfone mass spectrograms, wherein ordinate are response, and abscissa is m/z.
The measure of Figure 10 albendazole retention times, wherein ordinate are response, and abscissa is retention time.
Figure 11 albendazole quantitative and qualitatives ion is detailed, and wherein ordinate is response, and abscissa is retention time.
Figure 12 albendazole mass spectrograms, wherein ordinate are response, and abscissa is m/z.
The standard curve of Figure 13 albendazole -2- amino sulfones, wherein ordinate are peak area response, and abscissa reaches for acetysalicylic acid phenobarbital
Azoles -2- amino sulfone concentration.
The standard curve of Figure 14 albendazole-sulfoxides, wherein ordinate are peak area response, and abscissa is sub- albendazole
Sulfone concentration.
The standard curve of Figure 15 Albendazole sulfones, wherein ordinate are peak area response, and abscissa is that Albendazole sulfone is dense
Degree.
The standard curve of Figure 16 albendazoles, wherein ordinate are peak area response, and abscissa is albendazole concentration.
Figure 17 albendazoles and its metabolin quota ion S/N scheme, and wherein ordinate is response, when abscissa is to retain
Between, albendazole -2- amino sulfone, albendazole-sulfoxide, Albendazole sulfone, albendazole are followed successively by from top to bottom.
Specific embodiment
The term for being used in the present invention, unless otherwise specified, typically has those of ordinary skill in the art usual
The implication of understanding.
With reference to specific embodiment, and with reference to the data further detailed description present invention.Following examples are to be
The present invention is illustrated, rather than limits the scope of the present invention by any way.
Embodiment
1. the preparation of standard liquid
The preparation of 1.1 storing solutions
10.00mg albendazoles, albendazole -2- amino sulfone, albendazole-sulfoxide and Albendazole sulfone are weighed respectively
Standard items, are dissolved into methyl alcohol, constant volume to 10mL, used as the storing solution (be placed in -18 DEG C stored refrigerated) of 1000mg/L.
The preparation of interstitial fluid in 1.2 standards
1mL albendazoles, albendazole -2- amino sulfone, albendazole-sulfoxide and Albendazole sulfone mark are accurately measured respectively
The storing solution of quasi- product, is dissolved into methyl alcohol, constant volume to 10mL, (is placed in -18 DEG C of refrigerations to protect as interstitial fluid in the standard of 100mg/L
Deposit).
The preparation of 1.3 standard working curves
The standard liquid for being configured to 1,5,10,20,50,100 μ g/L with interstitial fluid in standard (uses methyl alcohol+water (v/v=1:1) it is fixed
Hold), as the standard liquid of working curve.
2. sample treatment
2.1 extraction purifications
Sample 5.00g is weighed, 5mL water, 150 μ L 50%NaOH solution and 1mL 1%2,6- di-t-butyl is added to first
Phenol, vortex mixed adds 20mL ethyl acetate, and vibration 1min ultrasonic extractions 20min, 4000r/min centrifugation 5min takes supernatant
Liquid, to adding 10mL ethyl acetate to repeat to extract once in residue, in pear shape bottle, 40 DEG C of revolvings are extremely to merge supernatant twice
It is dry；To 6mL acetonitrile saturation n-hexanes are added in the pear shape bottle after being spin-dried for, vibration is mixed, poured into centrifuge tube, then in pear shape bottle
2mL acetonitriles are added, is poured into centrifuge tube in the lump after the ultrasound that is vortexed 1min, the hydrochloric acid of 6mL 0.1mol/L is molten to being added in centrifuge tube
Liquid, vortex 2min, 4000r/min centrifugation 5min, removes n-hexane layer, standby；If emulsification, ultrasound and with suction pipe stir after from
The heart；
2.2 purification column purifications
After activating PCX solid-phase extraction columns with 5mL methyl alcohol and 5mL water balances, take extract solution and cross PCX decontaminating columns, 3mL is used respectively
Water and 3mL methyl alcohol drip washing, then with 15mL volumetric concentrations for 5% ammoniacal liquor methanol solution is eluted, the eluent of reception is in 40 DEG C of rotations
Steam to after doing；1mL methyl alcohol and 1mL water are separately added into, are vortexed, cross 0.22 μm of nylon leaching film, it is to be measured；
3. high performance liquid chromatography GC-MS detection
The high performance liquid chromatography GC-MS for using is Agilent LC-MSMS 1290/6460；
Mass spectrometry parameters：Ion gun AJS ESI sources；Gas Temp：325℃；Gas Flow：10L/min；Sheath Gas
Temp350℃；Sheath Gas flow：11L/min.
Liquid phase parameter：A is 0.1% aqueous formic acid, and B is methyl alcohol.Eluent gradient is as shown in table 1：
The eluent gradient of table 1
| Time | Methanol concentration |
| 1.00 | 20 |
| 2.00 | 100 |
| 4.00 | 100 |
| 4.01 | 20 |
| 5.5 | 20 |
4. result and analysis
4.1 mass spectral results
The mass spectral results of albendazole and its metabolin are as shown in table 2：
The mass spectral results of table 2
4.2 specificities
4.2.1 the specificity of albendazole -2- amino sulfone
50ppb albendazole -2- amino sulfone determines retention time by C18 chromatogram post separations.As shown in figure 1, when retaining
Between about 2.4min, and chromatogram peak shape preferably, noiseless peak occurs, and wherein abscissa is retention time, and ordinate is response.
Albendazole -2- amino sulfone quantitative and qualitatives ion is detailed as shown in Fig. 2 wherein ordinate is response, and abscissa is
Retention time.
As shown in figure 3, machine on 1ppm albendazole -2- amino sulfones, is optimized by mass spectrum and obtains 3 ion pairs, ordinate
It is response, abscissa is m/z.
4.2.2 the specificity of albendazole-sulfoxide
50ppb albendazole-sulfoxides determine retention time by C18 chromatogram post separations.As shown in figure 4, retention time is about
It is 2.9min, and the peak shape of chromatogram is preferable, noiseless peak occurs, and wherein abscissa is retention time, and ordinate is response.
Albendazole-sulfoxide quantitative and qualitative ion is detailed as shown in figure 5, wherein ordinate is response, when abscissa is to retain
Between.
As shown in fig. 6, machine on 1ppm albendazole-sulfoxides, is optimized by mass spectrum and obtain 3 ion pairs, ordinate is sound
Should, abscissa is m/z.
4.2.3 the specificity of Albendazole sulfone
50ppb Albendazole sulfones determine retention time by C18 chromatogram post separations.As shown in fig. 7, retention time is about
2.9min, and the peak shape of chromatogram is preferable, noiseless peak occurs.Wherein abscissa is retention time, and ordinate is response.
Albendazole sulfone quantitative and qualitative ion is detailed as shown in figure 8, wherein ordinate is response, when abscissa is to retain
Between.
As shown in figure 9, machine on 1ppm Albendazole sulfones, is optimized by mass spectrum and obtain 3 ion pairs, ordinate is response,
Abscissa is m/z.
4.2.4 the specificity of albendazole
50ppb Albendazole sulfones determine retention time by C18 chromatogram post separations.As shown in Figure 10, retention time is about
3.159min, and the peak shape of chromatogram is preferable, noiseless peak occurs, and abscissa is retention time, and ordinate is response.
Albendazole quantitative and qualitative ion is detailed as shown in figure 11, and wherein ordinate is response, and abscissa is retention time.
As shown in figure 12, machine on 1ppm albendazoles, is optimized by mass spectrum and respectively obtains 3 ion pairs, and ordinate is response,
Abscissa is m/z.
4.3 standard curves
4.3.1 the standard curve of albendazole -2- amino sulfone
Precision draws albendazole -2- amino sulfone standard items, and it is 1,5 to be diluted to series concentration with 50% methanol aqueous solution,
10,20,50,100ng/mL standard liquids, difference sample introduction is determined, with peak area response as ordinate, albendazole -2- amino sulfones
Concentration is abscissa.As shown in figure 13, the regression equation for obtaining albendazole -2- amino sulfones is Y=1378.144404*X-
594.187990, R2=0.9999, from coefficient correlation, in 1ng/mL~100ng/mL standard curve ranges of linearity,
UPLC-MSMS methods determine linear relationship well, and this standard curve can be used for accurate quantitative analysis.
4.3.2 the standard curve of albendazole-sulfoxide
Precision draws albendazole-sulfoxide standard items, and it is 1,5,10,20 to be diluted to series concentration with 50% methanol aqueous solution,
50,100ng/mL standard liquids, difference sample introduction is determined, and with peak area response as ordinate, albendazole-sulfoxide concentration is horizontal seat
Mark.As shown in figure 14, the regression equation for obtaining albendazole-sulfoxide is Y=519.827117*X-28.361658, R2=
0.9998, from coefficient correlation, in 1ng/mL~100ng/mL standard curve ranges of linearity, UPLC-MSMS methods determine line
Sexual intercourse is good, and this standard curve can be used for accurate quantitative analysis.
4.3.3 the standard curve of Albendazole sulfone
Precision draws Albendazole sulfone standard items, and it is 1,5,10,20 to be diluted to series concentration with 50% methanol aqueous solution,
50,100ng/mL standard liquids, difference sample introduction is determined, and with peak area response as ordinate, Albendazole sulfone concentration is abscissa.
As shown in figure 15, the regression equation for obtaining Albendazole sulfone is Y=1384.923769*X-533.206880, R2=0.9998,
From coefficient correlation, in 1ng/mL~100ng/mL standard curve ranges of linearity, it is good that UPLC-MSMS methods determine linear relationship
Good, this standard curve can be used for accurate quantitative analysis.
4.3.4 albendazole
Precision draws albendazole standard items, and it is 1,5,10,20,50 to be diluted to series concentration with 50% methanol aqueous solution,
100ng/mL standard liquids, difference sample introduction is determined, and with peak area response as ordinate, albendazole concentration is abscissa.As schemed
Shown in 16, the regression equation for obtaining albendazole is Y=8382.358953*X-2437.446609, R2=0.9999, by correlation
Coefficient is visible, and in 1ng/mL~100ng/mL standard curve ranges of linearity, UPLC-MSMS methods determine linear relationship well, this
Standard curve can be used for accurate quantitative analysis.
4.4 detection limits
The standard items of the albendazole and its metabolin that contain 1.0 μ g/kg equivalent to sample, premenstrual place are added in matrix
Machine testing in reason, calculates its signal to noise ratio (S/N) ＞ 10, as shown in figure 17.
Measure detection of the inventive method to albendazole and its metabolin and be limited to 1.0 μ g/kg.
4.5 checking matrix and the rate of recovery
The checking of matrix and the rate of recovery is as shown in table 3：
The checking of the matrix of table 3 and the rate of recovery
Commercially beef, pork liver, pig kidney, do mark-on and test back from supermarket purchase egg, raw milk, crucian matrix
Between yield 70%-90%, illustrate that this method has good stability.
5. conclusion
The albendazole and its metabolin in animal sources matrix are measured by with UPLC-LCMSMS methods, it is determined that
Extracted using BHT, NaOH and ethyl acetate, n-hexane purifying, PCX pillars are purified, and make Ah
Parbendazole and its metabolin chromatographic peak reach baseline separation, and peak shape is good, and test limit is low, and sensitivity is high, and method reclaims stabilization, this
Study as the measure of the albendazole in animal sources matrix and its metabolite residue amount establishes a kind of reliably analysis method.
Claims (4)
1. the detection method of a kind of albendazole and its metabolin, it is characterised in that：Using BHT and
NaOH extracts the albendazole and its metabolin in sample, is detected using high performance liquid chromatography GC-MS afterwards；Described 2,
The concentration of 6- BHTs is 1%；The concentration of the NaOH solution is 50%.
2. the detection method of albendazole and its metabolin according to claim 1, it is characterised in that：Step is as follows：
1) extraction purification
Sample 5.00g is weighed, 5mL water, 150 μ L 50%NaOH solution and 1mL 1%2,6- BHT, whirlpool is added
Rotation mixing, adds 20mL ethyl acetate, and vibration 1min ultrasonic extractions 20min, 4000r/min centrifugation 5min takes supernatant, to
10mL ethyl acetate is added to repeat to extract once in residue, in pear shape bottle, 40 DEG C of revolvings are to dry to merge supernatant twice；Xiang Xuan
6mL acetonitrile saturation n-hexanes are added in pear shape bottle after dry, vibration is mixed, poured into centrifuge tube, then to adding 2mL in pear shape bottle
Acetonitrile, pours into centrifuge tube in the lump after the ultrasound that is vortexed 1min, to the hydrochloric acid solution that 6mL 0.1mol/L are added in centrifuge tube, is vortexed
2min, 4000r/min are centrifuged 5min, remove n-hexane layer, standby；If emulsification, ultrasound and with suction pipe stir after be centrifuged；
2) column purification is purified
After activating PCX solid-phase extraction columns with 5mL methyl alcohol and 5mL water balances, take extract solution and cross PCX decontaminating columns, respectively with 3mL water and
3mL methyl alcohol drip washing, then with 15mL volumetric concentrations for 5% ammoniacal liquor methanol solution is eluted, the eluent of reception is rotated extremely in 40 DEG C
After dry；1mL methyl alcohol and 1mL water are separately added into, are vortexed, cross 0.22 μm of nylon leaching film, it is to be measured；
3) high performance liquid chromatography GC-MS detection
Mass spectrometry parameters：Ion gun AJS ESI sources；Gas Temp：325℃；Gas Flow：10L/min；Sheath Gas
Temp350℃；Sheath Gas flow：11L/min；
Liquid phase parameter：A is 0.1% aqueous formic acid, and B is methyl alcohol.
3. the application of albendazole according to claim 1 or claim 2 and its metabolism object detecting method, it is characterised in that：For examining
The albendazole and its metabolin surveyed in animal derived food.
4. the application of albendazole and its metabolism object detecting method according to claim 3, it is characterised in that：The animal sources
Property food be muscle, eggs, newborn class, liver and kidney.
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