CN103063756B - Method for separating antiulcer medicament by double-chiral selector capillary electrophoresis method - Google Patents
Method for separating antiulcer medicament by double-chiral selector capillary electrophoresis method Download PDFInfo
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Abstract
The invention provides a method for separating an antiulcer medicament by a double-chiral selector capillary electrophoresis method, and relates to a method for separating the antiulcer medicament. The invention provides a method for separating and analyzing four antiulcer medicaments (the pantoprazole, the omeprazole, the lansoprazole and the tentoprzole) by the double-chiral selector capillary electrophoresis method. Cu (II) and L-histidine complex, and hydroxypropyl-beta-cyclodextrin with a certain proportion are taken as the chiral selector, and an enantiomer can be separated by the four medicaments by the capillary electrophoresis method. According to the method, the plurality of chiral selectors are used, the method is higher in separation effect due to the synergistic effect of the chiral selectors, and is simple to operate, the chiral selectors are low in price, and a sample and a reagent are small in dosage. The method can be used for the in-vivo analysis of the antiulcer medicaments, and the optical purity detection of the products, and the technical support and guarantee can be provided for the research of the administration of the medicaments and the single enantiomer.
Description
Technical field
The present invention relates to a kind of method that separates anti-ulcer medicament, particularly relate to the method for a kind of pair of chiral selector capillary electrophoresis separation anti-ulcer medicament.
Background technology
Capillary Electrophoresis (capillary electrophoresis, CE) is called again high performance capillary electrophoresis (high-performance capillary electrophoresis, HPCE) because it has the advantage such as efficient, quick, easy.It is taking high-voltage dc as driving force, with charged particle by a kind of New Electrophoresis Technique separating in the kapillary that do not coexist of its partition factor, there is it and have that clastotype is many, separating column effect is high, analysis speed is fast, easy and simple to handle, sample and the advantage such as reagent consumption is few, environmental pollution is little, thereby enjoys favor in chiral separation research.
The method chiral selector kind is many, common selective agent has cyclodextrin, chiral crown ether, large cyclohexanol peptide antibiotics, linear polysaccharide, protein, chiral surfaces activating agent and ligand exchange compound etc., can also use multiple chiral selectors simultaneously, utilize its synergy to strengthen separating effect, and method is simple, quick, cost is low.At present, do not adopt two chiral selector capillary electrophoresis to separate the report containing sulfoxide radicals chipal compounds both at home and abroad.
Proton pump inhibitor (PPIs) comprises Pantoprazole, Omeprazole, Lansoprazole and Tenatoprazole.PPIs is mainly used in treating duodenal ulcer, stomach is burst, the diseases relevant to gastric acid secretion such as ulcer, reflux esophagitis.PPIs has similar molecular structure, has a chiral sulfur atom center in molecule, has R, two enantiomters of S, and because two enantiomorphs have similar physicochemical property, conventional method is difficult to separate, therefore the clinical form mainly with raceme is used.But many clinical testings prove, raceme administration is irrational, and exploitation single enantiomer anti-ulcer medicament is imperative.That at present this type of medicine chiral isolation analysis method has been reported has Chiral stationary phase liquid chromatography method, Mobile Phase Additives high performance liquid chromatography, ligand exchange capillary electrophoresis, a chiral additives capillary electrophoresis, rarely has with the hands property selective agent capillary electrophoresis to realize separation.
Summary of the invention
The object of the present invention is to provide a kind of pair of chiral selector capillary electrophoresis to separate the method for anti-ulcer medicament.Taking Cu(II) and L-Histidine complex and HP-β-CD be chiral selector, compartment analysis Pantoprazole, Omeprazole, Lansoprazole and tenatoprazole enantiomers.Body inner analysis and optical purity of products for this type of antiulcer chiral drug detect, for research and development and the single enantiomer administration of this type of chirality medicine provide technical support and guarantee.
The object of the invention is to be achieved through the following technical solutions:
A kind of pair of chiral selector capillary electrophoresis separates the method for anti-ulcer medicament, for a kind of method that separates Pantoprazole, Omeprazole, Lansoprazole and Tenatoprazole raceme, the method is used two chiral selector capillary electrophoresis to separate and is drawn azoles drug enantiomer, and its chiral selector used has two kinds: one is Cu(II) and L-Histidine; Another kind is HP-β-CD, said method comprising the steps of:
A. the configuration of sample and running buffer: preparation sample stock solution is called gets Pantoprazole, Omeprazole, Lansoprazole and Tenatoprazole raceme sample powder 10 mg, put in the brown volumetric flask of 10 mL, dissolve and be settled to scale with the methyl alcohol after filtering, shaking up; Obtain the storing solution that sample concentration is 1 mg/mL ,-20
oCrefrigerator store; Sample test solution: in the brown volumetric flask of sample thief storing solution 1 mL respectively to 10 mL,, shake up to scale with methanol constant volume, obtain 100 μ g/mL test liquids, 4
oCrefrigerator store; Running buffer: take successively sodium dihydrogen phosphate, HP-β-CD, Schweinfurt green and L-Histidine 0.0195 g, 0.05 g, 0.050 g, 0.0582 g and be placed in 50 mL beakers, adding 25 mL redistilled waters dissolves, be adjusted to pH 5.0 with 0.1 M sodium hydroxide solution and 10% phosphoric acid, obtain running buffer, for subsequent use after 0.45 μ m filtering with microporous membrane;
B. prepare separate apparatus: detachment process is carried out in quartz capillary, choose the kapillary of internal diameter 50 μ m, intercept segment length 53 cm, obtain detection window removing polyimide layer capillaceous apart from port 8 cm places, new kapillary needs to rinse and activation before use, while analysis continuously, before each analysis, use successively each 10 min of flushing of 10%HCl, 1MNaOH, redistilled water and running buffer successively;
C. sample introduction: separation condition is set before sample introduction, and separation voltage 15 kV, detect wavelength 290 nm; Tenatoprazole 306 nm, sample introduction height 10 cm, sample injection time 10 s, anodal sample introduction negative pole detects; Between sample introduction, respectively rush post 5 min with running buffer and redistilled water successively, then carry out sample introduction next time.
Described a kind of pair of chiral selector capillary electrophoresis separates the method for anti-ulcer medicament, when described sample operation running buffer and sample all through 0.45 μ m filtering with microporous membrane, and ultrasonic degas, sample dissolves with methyl alcohol, 4 DEG C of Refrigerator stores are for subsequent use.
A kind of pair of described chiral selector capillary electrophoresis separates the method for anti-ulcer medicament, described electrophoretic separation Pantoprazole, Omeprazole, Lansoprazole enantiomorph: running buffer: 5 mmol/L sodium dihydrogen phosphates, containing mg/Mlhp-β-CD, 15 mmol/L L-Histidines and 10 mmol/L Schweinfurt greens, are adjusted to pH 5.0; Separation voltage: 15 kV; Ultraviolet detects wavelength: 290 nm.
A kind of pair of described chiral selector capillary electrophoresis separates the method for anti-ulcer medicament, described electrophoretic separation tenatoprazole enantiomers: running buffer: 5 mmol/L sodium dihydrogen phosphates, containing 20 mg/Mlhp-β-CD, 15 mmol/L L-Histidines and 10 mmol/L Schweinfurt greens, are adjusted to pH 5.0; Separation voltage: 15 kV; Ultraviolet detects wavelength: 306 nm.
A kind of pair of described chiral selector capillary electrophoresis separates the method for anti-ulcer medicament, and described instrument is prepared: kapillary overall length 53 cm, effective length 45 cm, internal diameter: 50 mm; New kapillary needs to rinse and activation before use, while analysis continuously, uses successively each 10 min of flushing of 10%HCl, 1MNaOH, redistilled water and running buffer before each analysis; Between sample introduction, respectively rush post 5 min with running buffer and redistilled water successively, then carry out sample introduction next time.
Described a kind of pair of chiral selector capillary electrophoresis separates the method for anti-ulcer medicament, and described chiral selector has two kinds: one is Cu(II) and the complex of L-Histidine, coordination ratio is 1:1.5; Another kind is HP-β-CD.
Advantage of the present invention and effect are:
The present invention adopts that two chiral selector capillary electrophoresis selectivity are good, separation efficiency is high, simple to operate, cost is low, environmentally friendly, few and cheap being easy to get of chiral selector consumption, can detect for the body inner analysis of this type of antiulcer chiral drug and optical purity, provide technical support and guarantee for researching and developing this type of chirality medicine and single enantiomer administration.
Brief description of the drawings
Fig. 1 is that the two chiral selector capillary electrophoresis of the present invention separate pantoprazole enantiomers chromatogram;
Fig. 2 is that the two chiral selector capillary electrophoresis of the present invention separate omeprazole enantiomer chromatogram;
Fig. 3 is that the two chiral selector capillary electrophoresis of the present invention separate Lansoprazole enantiomorph chromatogram;
Fig. 4 is that the two chiral selector capillary electrophoresis of the present invention separate tenatoprazole enantiomers chromatogram.
Embodiment
Below in conjunction with embodiment, the present invention is described in detail.
The present invention applies a kind of high-performance capillary electrophoresis technology, the compartment analysis of enantiomers of chiral drugs, be specially the chiral isolation analysis method of Pantoprazole, Omeprazole, Lansoprazole and four kinds of anti-ulcer medicament racemies of Tenatoprazole, the method with the hands property selective agent capillary electrophoresis separates several azole drug enantiomorphs that draw.
The method of capillary electrophoresis compartment analysis antiulcer class chiral drug of the present invention, deposition condition is using a certain proportion of Cu(II) and L-Histidine complex, HP-β-CD as chiral selector, taking sodium dihydrogen phosphate as buffer solution (pH 4.0 ~ 6.0), separation voltage 15 kV; It is 290 nm (wherein Tenatoprazole is 306 nm) that ultraviolet detects wavelength.
Chiral selector of the present invention is selected from: HP-β-CD, beta-schardinger dextrin-and sulfobutyl ether-beta-cyclodextrin, Cu(II) and L-Histidine.Optimal selection HP-β-CD, Cu(II) and L-Histidine.Chiral selector central ion Cu(II) and the ratio of ligand L-histidine be 1:1 ~ 1:2, most preferably 1:1.5.Buffer solution is selected from the mixed liquor of borax, ammonium acetate, sodium dihydrogen phosphate, ammonium dihydrogen phosphate (ADP), sodium hydrogen phosphate, boric acid etc. and above-mentioned solution different proportion, preferably phosphoric acid sodium dihydrogen, ammonium dihydrogen phosphate (ADP), most preferably sodium dihydrogen phosphate.PH value of buffer solution is 4.0 ~ 6.0, and preferably pH value is 4.5 ~ 5.5, and most preferably pH value is 5.0.Deposition condition separation voltage is 5 ~ 25 kV, preferably 10 ~ 20 kV, most preferably 15 kV.
Two chiral selector capillary electrophoresis method for separating and analyzing of Pantoprazole of the present invention, Omeprazole, Lansoprazole and Tenatoprazole
,comprise sample configuration, 2 steps of EC separation condition be set:
A. sample configuration: the configuration of sample stock solution: precision takes Pantoprazole, Omeprazole, Lansoprazole and Tenatoprazole sample powder 10 mg respectively, put in the brown volumetric flask of 10 mL, dissolve and be settled to scale with the methyl alcohol after filtering, shake up.Obtain the storing solution that each sample concentration is 1 mg/mL ,-20
oCrefrigerator store.The preparation of sample test solution: precision measures in the brown volumetric flask of each sample storing solution 1 mL respectively to 10 mL,, shakes up to scale with methanol constant volume, obtains 100 μ g/mL test liquids, 4
oCrefrigerator store.
B. CLEC separation condition: running buffer: 5 mmol/L sodium dihydrogen phosphates, 20 mg/mL HP-β-CDs, 15 mmol/L L-Histidines, 10 mmol/L Schweinfurt greens, pH 5.0, then ultrasonic degas after the membrane filtration of 0.45 μ m.
Capillary column: overall length 53 cm, effective length 45 cm, internal diameter 50 μ m; Wash post mode: capillary column respectively rinses sample introduction after 10 min with 0.1 mol/L sodium hydroxide solution, redistilled water, running buffer successively; After respectively rinsing 5 min with redistilled water, running buffer between sample introduction, carry out next sample introduction.Input mode: siphon sample introduction, anodal sample introduction negative pole detects; Sample introduction difference in height: 10 cm; Sample injection time: 10 s; Column temperature: room temperature.Detect wavelength: 290 nm(Tenatoprazole 306 nm); Separation voltage: 15kV.
Fig. 1 is that two chiral selector capillary electrophoresis separate pantoprazole enantiomers chromatograms, and two enantiomorph analysis times, degree of separation was greater than 4.2 in 19 minutes.
Fig. 2 is that two chiral selector capillary electrophoresis separate omeprazole enantiomer chromatograms, and two enantiomorph analysis times, degree of separation was greater than 5.0 in 17 minutes.
Fig. 3 is that two chiral selector capillary electrophoresis separate Lansoprazole enantiomorph chromatograms, and two enantiomorph analysis times, degree of separation reached 6.2 in 20 minutes.
Fig. 4 is that two chiral selector capillary electrophoresis separate Lansoprazole enantiomorph chromatograms, and two enantiomorph analysis times, degree of separation reached 3.9 in 18 minutes.
Embodiment mono-:
1, precision takes Pantoprazole, Omeprazole, each 10 mg of Lansoprazole raceme, puts respectively in the brown volumetric flask of 10 mL, dissolves and is settled to scale with methyl alcohol, shakes up.Obtain the storing solution that each sample concentration is 1 mg/mL ,-20
oCrefrigerator store.Precision measures in the brown volumetric flask of each sample storing solution 1 mL respectively to 10 mL,, shakes up to scale with methanol constant volume, obtains 100 μ g/mL test liquids, for subsequent use after 0.45 μ m filtering with microporous membrane.
2, preparation 5 mMNaH
2pO
4make running buffer containing 20 mg/mL HP-β-CDs, 10 mM Schweinfurt greens and 15 mML-histidines, use 10%H
3pO
4be adjusted to pH 5.0 with 0.1 MNaOH, through 0.45 μ m filtering with microporous membrane, and ultrasonic degas is for subsequent use.Capillary column is walked baseline after rinsing 10 min with 0.1 MNaOH, redistilled water and above-mentioned running buffer are each successively, after baseline is steady, (2 min left and right) adopts siphon sample introduction, sample introduction height 10 cm, sample injection time 10 s, anodal sample introduction negative pole detects, and records electrophoretogram.Between sample introduction, respectively rush post 5 min with redistilled water and running buffer successively, walk baseline 2 min left and right, then enter next sample.Separation voltage: 15 kV, ultraviolet detects wavelength: 290 nm.Separation electrophoresis figure is as Fig. 2, Fig. 3, Fig. 4, and Pantoprazole, Omeprazole, Lansoprazole respectively reach baseline separation.
Embodiment bis-:
1, precision takes each 10 mg of Tenatoprazole raceme, puts respectively in the brown volumetric flask of 10 mL, dissolves and is settled to scale with methyl alcohol, shakes up.Obtain the storing solution that each sample concentration is 1 mg/mL ,-20
oCrefrigerator store.Precision measures in the brown volumetric flask of each sample storing solution 1 mL respectively to 10 mL,, shakes up to scale with methanol constant volume, obtains 100 μ g/mL test liquids, for subsequent use after 0.45 μ m filtering with microporous membrane.
2, preparation 5 mM NaH
2pO
4make running buffer containing 20 mg/mL HP-β-CDs, 10 mM Schweinfurt greens and 15 mM L-Histidines, use 10%H
3pO
4be adjusted to pH 5.0 with 0.1 M NaOH, through 0.45 μ m filtering with microporous membrane, and ultrasonic degas is for subsequent use.Capillary column is walked baseline after rinsing 10 min with 0.1 M NaOH, redistilled water and above-mentioned running buffer are each successively, after baseline is steady, (2 min left and right) adopts siphon sample introduction, sample introduction height 10 cm, sample injection time 10 s, anodal sample introduction negative pole detects, and records electrophoretogram.Between sample introduction, respectively rush post 5 min with redistilled water and running buffer successively, walk baseline 2 min left and right, then enter next sample.Separation voltage: 15 kV, ultraviolet detects wavelength: 306 nm.
Claims (1)
1. the method for two chiral selector capillary electrophoresis separation anti-ulcer medicaments, for a kind of method that separates Pantoprazole, Omeprazole, Lansoprazole and Tenatoprazole raceme, it is characterized in that, the method is used two chiral selector capillary electrophoresis to separate and is drawn azoles drug enantiomer, its chiral selector used has two kinds: one is Cu(II) and the complex of L-Histidine, coordination ratio is 1:1.5; Another kind be hydroxypropyl-
-cyclodextrin; Said method comprising the steps of:
A. the configuration of sample and running buffer: preparation sample stock solution is called gets Pantoprazole, Omeprazole, Lansoprazole and Tenatoprazole raceme sample powder 10 mg, put in the brown volumetric flask of 10 mL, dissolve and be settled to scale with the methyl alcohol after filtering, shaking up; Obtain the storing solution that sample concentration is 1 mg/mL ,-20 DEG C of Refrigerator stores; Sample test solution: in the brown volumetric flask of sample thief storing solution 1 mL respectively to 10 mL,, shake up to scale with methanol constant volume, obtain 100 μ g/mL test liquids, 4 DEG C of Refrigerator stores; Running buffer: take successively sodium dihydrogen phosphate, hydroxypropyl-
-cyclodextrin, Schweinfurt green and L-Histidine 0.0195 g, 0.05 g, 0.050 g, 0.0582 g are placed in 50 mL beakers, adding 25 mL redistilled waters dissolves, be adjusted to pH 5.0 with 0.1 M sodium hydroxide solution and 10% phosphoric acid, obtain running buffer, for subsequent use after 0.45 μ m filtering with microporous membrane;
B. prepare separate apparatus: detachment process is carried out in quartz capillary, choose the kapillary of internal diameter 50 μ m, intercept segment length 53 cm, obtain detection window removing polyimide layer capillaceous apart from port 8 cm places, new kapillary needs to rinse and activation before use, while analysis continuously, before each analysis, use successively each 10 min of flushing of 10%HCl, 1MNaOH, redistilled water and running buffer successively;
C. sample introduction: separation condition is set before sample introduction, and separation voltage 15 kV, detect wavelength 290 nm; Tenatoprazole 306 nm, sample introduction height 10 cm, sample injection time 10 s, anodal sample introduction negative pole detects; Between sample introduction, respectively rush post 5 min with running buffer and redistilled water successively, then carry out sample introduction next time;
Described electrophoretic separation Pantoprazole, Omeprazole, Lansoprazole enantiomorph: running buffer: 5 mmol/L sodium dihydrogen phosphates containing 20 mg/mL hydroxypropyls-
-cyclodextrin, 15 mmol/L L-Histidines and 10 mmol/L Schweinfurt greens, be adjusted to pH 5.0; Separation voltage: 15 kV; Ultraviolet detects wavelength: 290 nm;
Described electrophoretic separation tenatoprazole enantiomers: running buffer: 5 mmol/L sodium dihydrogen phosphates containing 20 mg/mL hydroxypropyls-
-cyclodextrin, 15 mmol/L L-Histidines and 10 mmol/L Schweinfurt greens, be adjusted to pH 5.0; Separation voltage: 15 kV; Ultraviolet detects wavelength: 306 nm;
Described instrument is prepared: kapillary overall length 53 cm, effective length 45 cm, internal diameter: 50 mm; New kapillary needs to rinse and activation before use, while analysis continuously, uses successively each 10 min of flushing of 10%HCl, 1MNaOH, redistilled water and running buffer before each analysis; Between sample introduction, respectively rush post 5 min with running buffer and redistilled water successively, then carry out sample introduction next time.
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| CN106000101B (en) * | 2016-06-15 | 2018-10-26 | 沈阳化工大学 | A kind of method of separation of phenylalanine, tyrosine and tryptophan raceme |
| CN107037154A (en) * | 2017-04-26 | 2017-08-11 | 苏州海科医药技术有限公司 | The chiral LC MS/MS high-flux detection methods of Pantoprazole in human plasma |
| CN108181392B (en) * | 2017-12-23 | 2020-09-04 | 贝克诺顿(浙江)制药有限公司 | Method for separating and detecting enantiomer in omeprazole |
| CN114486444B (en) * | 2022-02-07 | 2024-02-20 | 洛阳师范学院 | Capillary electrophoresis separation method of atenolol non-racemate mixture |
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| CN102703923A (en) * | 2012-05-21 | 2012-10-03 | 沈阳化工大学 | Method for separating lansoprazole and omeprazole racemates |
| CN102703922A (en) * | 2012-05-21 | 2012-10-03 | 沈阳化工大学 | Method for separating pantoprazole from tenatoprazole drug raceme |
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| CN102703923A (en) * | 2012-05-21 | 2012-10-03 | 沈阳化工大学 | Method for separating lansoprazole and omeprazole racemates |
| CN102703922A (en) * | 2012-05-21 | 2012-10-03 | 沈阳化工大学 | Method for separating pantoprazole from tenatoprazole drug raceme |
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