CN115290800B - Method for splitting antofloxacin enantiomer by chiral stationary phase method - Google Patents
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Abstract
The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a method for splitting antofloxacin enantiomer by a chiral stationary phase method, which comprises the steps of preparing a mixed reference substance solution of levorotatory antofloxacin and dextrorotatory antofloxacin, carrying out analysis and detection by adopting an HPLC method and a chiral column as a chromatographic column and a copper sulfate solution-isopropanol as a mobile phase, wherein the volume ratio of the copper sulfate solution to the isopropanol in the mobile phase is 87-93. According to the method, HPLC chromatographic conditions are optimized, the chiral chromatographic column is adopted to realize the separation of the levorotatory antofloxacin and the dextrorotatory antofloxacin, the method is good in separation effect, small in interference, high in speed, good in repeatability of detection results, high in precision, low in detection limit, and capable of measuring the content of the dextrorotatory body, so that the dextrorotatory body in the antofloxacin hydrochloride tablet is strictly controlled.
Description
Technical Field
The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a method for splitting an antofloxacin enantiomer by a chiral stationary phase method.
Background
The levo-antofloxacin and the dextro-antofloxacin are enantiomers, wherein the levo-antofloxacin is an active ingredient of the medicine antofloxacin hydrochloride. The antofloxacin hydrochloride is a new medicine which is autonomously developed in China, belongs to quinolone medicines, the antibacterial action of the antofloxacin after structural modification is superior to that of ofloxacin and ciprofloxacin, the introduction of amino groups can enable the antofloxacin to effectively reduce photosensitive toxicity, the cardiac toxicity is even lower than that of moxifloxacin, and the safety is high.
The drug antofloxacin hydrochloride contains a single levorotatory isomer, in order to control the drug quality, the dextrorotatory antofloxacin in the antofloxacin hydrochloride tablet needs to be controlled, but the control precondition is that the levorotatory antofloxacin and the dextrorotatory antofloxacin are separated. At present, few reports about the determination of levorotatory antofloxacin and dextrorotatory antofloxacin are reported, for example, in the prior art (Hongjian, picramon; detection of enantiomer impurities in levorotatory antofloxacin hydrochloride by an efficient capillary electrophoresis method [ J ]. Analysis and test report, 006: 888-890 in 2007), although the resolution of enantiomers of levorotatory antofloxacin and dextrorotatory antofloxacin is realized by adopting an efficient capillary electrophoresis method, peaks of levorotatory antofloxacin and dextrorotatory antofloxacin cannot reach baseline separation, and the detection precision (RSD is more than 2%) and the detection limit are both low. Therefore, a method for simply, quickly and accurately separating the levorotatory antofloxacin and the dextrorotatory antofloxacin is urgently needed.
Disclosure of Invention
The invention aims to provide a method for splitting an antofloxacin enantiomer by a chiral stationary phase method, which has the advantages of simple solution preparation, convenient operation, high splitting speed, high precision and low detection limit, can be used for determining the content of dextro-antofloxacin, and is suitable for controlling dextro isomer in an antofloxacin hydrochloride tablet.
Before researching the invention, the antofloxacin enantiomer is resolved by utilizing a chiral mobile phase additive method, although the method has certain advantages compared with the prior art, chiral amino acid and copper sulfate with higher concentration are added into the chiral mobile phase, the pH value needs to be adjusted to 3.5 by using sodium hydroxide to meet the separation effect, but the mobile phase is easy to produce precipitate after being placed for a period of time under the pH condition, needs to be filtered again before each use, and simultaneously, the balance time is longer, so that the chromatographic column is easy to be damaged; in addition, the mobile phase also contains a higher proportion of organic phase, which is not environment-friendly. In order to reduce the use of an organic phase and the damage of a chromatographic column and reduce the complicated operation of preparing a mobile phase, the inventor uses a chiral stationary phase resolution method to replace a chiral mobile phase additive resolution method to solve the problems. The specific scheme is as follows:
the invention provides a method for splitting antofloxacin enantiomer by a chiral stationary phase method, which comprises the steps of firstly preparing a mixed reference substance solution of levo-antofloxacin and dextro antofloxacin, adopting an HPLC method, taking a chiral column as a chromatographic column, and taking a copper sulfate solution-isopropanol as a mobile phase for analysis and detection; the volume ratio of the copper sulfate solution to the isopropanol in the mobile phase is 87-93. Specifically, the chiral chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column.
In the technical scheme, resolution of levorotatory antofloxacin and dextrorotatory antofloxacin is realized by optimizing HPLC chromatographic conditions and using a Fenomei 3126 (D) -penicillamine chiral chromatographic column. The stationary phase of the chiral chromatographic column is formed by tightly combining reversed-phase filler with chiral selection ligand D-penicillamine through a hydrophobic effect, copper ions with a certain concentration are added into a mobile phase, and reversible metal complexes are formed by the copper ions, the chiral selection ligand D-penicillamine and a substance to be detected respectively during sample analysis.
Further, in the technical scheme, the volume ratio of the copper sulfate solution to the isopropanol in the mobile phase is 87-90; the volume ratio is preferably 90.
Further, in the technical scheme, the concentration of the copper sulfate solution is 2.8mmol/L.
In the technical scheme, the copper sulfate solution-isopropanol is used as the mobile phase, the preparation is simple, the pH of the mobile phase does not need to be adjusted, the precipitate cannot be separated out after long-term storage, and the chromatographic column cannot be damaged.
Further, in the above technical solution, the wavelength in the HPLC detection is 301nm.
Further, in the above technical scheme, the column temperature is 30-40 ℃ in HPLC detection.
Furthermore, in the above technical scheme, the sample amount is 20 μ L in the HPLC detection.
Further, in the above technical scheme, the flow rate is 1.0mL/min in the HPLC detection, and the specification of the chromatographic column is 250 × 4.6mm.
Further, in the above technical solution, the preparation method of the mixed reference solution comprises: the method comprises the steps of precisely weighing a levorotatory antofloxacin reference substance and a dextrorotatory antofloxacin reference substance, placing the levorotatory antofloxacin reference substance and the dextrorotatory antofloxacin reference substance into a measuring bottle, adding a mobile phase for dissolving and diluting to prepare reference substance stock solutions containing the levorotatory antofloxacin and the dextrorotatory antofloxacin with the concentrations of 1000 mu g/mL respectively, and then taking a proper amount of the reference substance stock solutions to prepare mixed reference substance solutions containing the levorotatory antofloxacin and the dextrorotatory antofloxacin with the concentrations of 300 mu g/mL respectively.
The invention also provides application of the method for splitting the antofloxacin enantiomer by the chiral stationary phase method in quality detection of the antofloxacin hydrochloride tablets.
Further, in the technical scheme, a proper amount of antofloxacin hydrochloride tablet samples are precisely weighed, the antofloxacin hydrochloride tablets are placed in a measuring bottle, the mobile phase solution is added for ultrasonic dissolution, the solution is filtered to obtain a test sample solution, and then the HPLC method is adopted for detection.
Compared with the prior art, the method has the beneficial effects that:
1. according to the invention, the separation of levo-antofloxacin and dextro-antofloxacin is realized by optimizing HPLC (high performance liquid chromatography) chromatographic conditions and adopting chiral chromatography, and the adopted chromatographic conditions have the advantages of good separation effect, small interference, high speed, good repeatability of detection results and low detection limit.
2. The resolution method provided by the invention not only can be used for resolving levo-antofloxacin and dextro-antofloxacin, but also can be used for determining the content of dextro isomer in the antofloxacin hydrochloride tablet, so that the dextro isomer in the antofloxacin hydrochloride tablet is strictly controlled, and the quality of the antofloxacin hydrochloride tablet can be effectively monitored.
3. The resolution method has simple and convenient pretreatment, does not need to filter the mobile phase subsequently, is convenient to use and environment-friendly, and has good precision and repeatability and is superior to the high-efficiency capillary electrophoresis method.
Drawings
FIG. 1 is a chromatogram of example 1 of the present invention, wherein the left peak is dextro-antofloxacin and the right peak is levo-antofloxacin;
FIG. 2 is a chromatogram of example 2 of the present invention, in which the left peak is dextroantofloxacin and the right peak is levoantofloxacin;
FIG. 3 is a chromatogram of example 3 of the present invention, in which the left peak is dextroantofloxacin and the right peak is levoantofloxacin;
FIG. 4 is a chromatogram of example 4 of the present invention, in which the left peak is dextroantofloxacin and the right peak is levoantofloxacin;
FIG. 5 is a chromatogram of example 5 of the present invention, wherein the left peak is dextro-antofloxacin and the right peak is levo-antofloxacin;
fig. 6 is a typical chromatogram of the test solution in example 6 of the present invention, in which the left peak is dextroantofloxacin and the right peak is levoantofloxacin.
Detailed Description
The above technical features of the present invention and the technical features (as the embodiment examples) described in detail below can be combined with each other to form a new or preferred technical solution, but the present invention is not limited to these embodiments, and the embodiments do not limit the present invention in any way.
The experimental procedures in the following examples are conventional unless otherwise specified. The formulations according to the following examples are all ordinary commercial products and can be obtained by commercial purchase, unless otherwise specified.
The invention is described in further detail below with reference to the figures and examples:
laboratory instruments and reagents:
1. instrument for measuring the position of a moving object
LC-20AD XR HPLC, with diode array detector (Shimadzu corporation, japan), METTLER MS205DU electronic balance.
2. Reagent
The test solution comprises dextro-antofloxacin reference substances (the source is Chinese food and drug inspection institute, the batch number is 130466-201101, and the content is 90.0 percent), levo-antofloxacin reference substances (the source is Chinese food and drug inspection institute, the batch number is 130457-201101, and the content is 90.9 percent), isopropanol is chromatographically pure, and other reagents are analytically pure.
Antofloxacin hydrochloride tablets (production enterprise: anhui Global pharmaceutical industry Co., ltd., specification: 0.1g, lot No. 190117, average tablet weight 0.181g, active ingredient is single antofloxacin levo).
Preparation of the solution:
respectively and precisely weighing 27.47mg and 27.58mg of levorotatory antofloxacin and dextrorotatory antofloxacin reference substances, putting the levorotatory antofloxacin and the dextrorotatory antofloxacin reference substances into a 25mL measuring flask, adding a mobile phase for dissolving, diluting to a scale, and shaking up to obtain reference substance stock solutions (respectively containing levorotatory antofloxacin and dextrorotatory antofloxacin with the concentration of about 1000 mug/mL).
Example 1
A method for resolving antofloxacin enantiomer by a chiral stationary phase method comprises the following steps:
taking a reference substance stock solution, adding a mobile phase to prepare a mixed reference substance solution containing levorotatory antofloxacin and dextrorotatory antofloxacin with the concentration of about 300 mu g/mL;
the following chromatographic conditions were used for the determination:
mobile phase: 2.8mmol/L copper sulfate solution-isopropanol (90: 10);
flow rate: 1.0mL/min;
detection wavelength: 301nm;
sample introduction amount: 20 mu L of the solution;
column temperature: 40 ℃;
the chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column (250X 4.6 mm).
The resulting chromatogram is shown in FIG. 1, and the chromatographic parameters are shown in Table 1.
Example 2
A method for splitting antofloxacin enantiomer by a chiral stationary phase method comprises the following steps:
taking a reference substance stock solution, adding a mobile phase to prepare a mixed reference substance solution containing levorotatory antofloxacin and dextrorotatory antofloxacin with the concentration of about 300 mu g/mL;
the following chromatographic conditions were used for the determination:
mobile phase: 2.8mmol/L copper sulfate solution-isopropanol (87: 13);
flow rate: 1.0mL/min;
detection wavelength: 301nm;
sample introduction amount: 20 mu L of the solution;
column temperature: 30 ℃;
the chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column (250X 4.6 mm).
The chromatogram obtained is shown in FIG. 2, and the chromatographic parameters are shown in Table 1.
Example 3
A method for resolving antofloxacin enantiomer by a chiral stationary phase method comprises the following steps:
taking a reference substance stock solution, adding a mobile phase to prepare a mixed reference substance solution containing levorotatory antofloxacin and dextrorotatory antofloxacin with the concentration of about 300 mu g/mL;
the following chromatographic conditions were used for the determination:
mobile phase: 2.8mmol/L copper sulfate solution-isopropanol (90: 10);
flow rate: 1.0mL/min;
detection wavelength: 301nm;
sample injection amount: 20 mu L of the solution;
column temperature: 30 ℃;
the chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column (250X 4.6 mm).
The chromatogram obtained is shown in FIG. 3, and the chromatographic parameters are shown in Table 1.
Example 4
A method for resolving antofloxacin enantiomer by a chiral stationary phase method comprises the following steps:
taking a reference substance stock solution, adding a mobile phase to prepare a mixed reference substance solution containing levorotatory antofloxacin and dextrorotatory antofloxacin with the concentration of about 300 mu g/mL;
the following chromatographic conditions were used for the determination:
mobile phase: 2.8mmol/L copper sulfate solution-isopropanol (93: 7);
flow rate: 1.0mL/min;
detection wavelength: 301nm;
sample injection amount: 20 mu L of the solution;
column temperature: 40 ℃;
the chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column (250X 4.6 mm).
The chromatogram obtained is shown in FIG. 4, and the chromatographic parameters are shown in Table 1.
Example 5
A method for resolving antofloxacin enantiomer by a chiral stationary phase method comprises the following steps:
taking a reference substance stock solution, adding a mobile phase to prepare a mixed reference substance solution containing levo-antofloxacin and dextro-antofloxacin with the concentration of about 300 mu g/mL respectively;
the following chromatographic conditions were used for the determination:
mobile phase: 2.8mmol/L copper sulfate solution (containing 40mmol/L ammonium acetate, pH adjusted to 5.0 with glacial acetic acid) -isopropanol (90: 10);
flow rate: 1.0mL/min;
detection wavelength: 301nm;
sample introduction amount: 20 mu L of the solution;
column temperature: 40 ℃;
the chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column (250X 4.6 mm).
The chromatogram obtained is shown in FIG. 5, and the chromatographic parameters are shown in Table 1.
TABLE 1 chromatographic parameters
As can be seen from fig. 1 to 5 and the data in table 1, the separation degree of levo-antofloxacin and dextro-antofloxacin resolved under the chromatographic conditions is good, and particularly, the analysis time of the embodiments 1 to 3 is short, the speed is high, and the sensitivity is high.
In example 4, the ratio of the mobile phase solution was different from that in example 1, the separation degrees of levo-antofloxacin and dextro-antofloxacin were also better, but the retention time was increased more than in the best example 1, and at the same time, the peak height of dextro-antofloxacin was too much decreased, which easily resulted in the deterioration of sensitivity.
In example 5, ammonium acetate and glacial acetic acid were added to the mobile phase, which gave better resolution and tailing factor, except that the analysis time was longer than in the best example 1, and the mobile phase contained higher concentrations of ammonium acetate and acetic acid, which gave a noisier baseline and a worse peak height for dextro-antofloxacin than in example 1.
Example 6
1. Preparation of the Standard Curve
Appropriate amounts of reference stock solutions of levo-antofloxacin and dextro-antofloxacin were prepared into mixed reference solutions with concentrations of about 1000, 800, 700, 500, 300, 200, 100, 10, 1, 0.5. Mu.g/mL, respectively, and the solutions were measured under the chromatographic conditions in example 1, respectively, and chromatograms were recorded. And performing linear regression by taking the concentrations (x) of the levo-antofloxacin and the dextro-antofloxacin as abscissa and the peak areas of the levo-antofloxacin and the dextro-antofloxacin as ordinate (y).
The levo-antofloxacin concentration is in a good linear relation with the peak area between about 0.5 and 1000 mu g/mL, and the regression equation is y =8.4988 multiplied by 10 4 x–4.5782×10 5 ，R²= 0.9997。
The concentration of the dextro-antofloxacin is between about 0.5 and 500 mu g/mL and has good linear relation with the peak area, and the regression equation is y = 7.7719 multiplied by 10 4 x–1.5223×10 5 ，R²= 0.9999。
2. Precision test
And taking a proper amount of reference substance stock solutions of the levorotatory antofloxacin and the dextrorotatory antofloxacin to prepare mixed reference substance solutions with the concentrations of the levorotatory antofloxacin and the dextrorotatory antofloxacin of about 300 mu g/mL, measuring according to the chromatographic conditions in the embodiment 1 and recording a chromatogram map. The mixed reference substance solution is continuously injected into a sample 6 needles, and the RSD of the peak areas of the levo-antofloxacin and the dextro-antofloxacin is 0.7 percent and 0.3 percent, which indicates that the precision of the method is good.
3. Quantitative limit and detection limit
Taking a proper amount of reference substance stock solution of the levo-antofloxacin and the dextro-antofloxacin to prepare mixed reference substance solution with the concentrations of the levo-antofloxacin and the dextro-antofloxacin being about 2 mu g/mL respectively, diluting the mixed reference substance solution into solution with the concentrations of the levo-antofloxacin and the dextro-antofloxacin being about 0.5 mu g/mL and 0.15 mu g/mL respectively by using a mobile phase, respectively determining according to the chromatographic conditions in the embodiment 1, and recording a chromatogram. As a result, the peak signal-to-noise ratios of the levo-antofloxacin and the dextro-antofloxacin respectively meet the requirements of 10: 1 and 3: 1. In the method, the detection limit and the quantification limit of the levo-antofloxacin and the dextro-antofloxacin are respectively 0.5 mu g/mL and 0.15 mu g/mL.
4. Reproducibility and sample determination
The antofloxacin hydrochloride tablets are taken and ground, about 18mg is precisely weighed, the ground antofloxacin hydrochloride tablets are placed into a 10mL measuring flask, mobile phase ultrasound is added to dissolve the antofloxacin hydrochloride tablets, the obtained solution is filtered to be used as a test solution, and 6 parts of the antofloxacin hydrochloride tablets are prepared in parallel. 1mL of the solution was measured out precisely, placed in a 100mL measuring flask, dissolved by ultrasonic wave with a mobile phase, and filtered to obtain a control solution. Taking the test solution and the control solution, respectively measuring according to the chromatographic conditions in the example 1, and recording the chromatogram, wherein a typical chromatogram of the test solution is shown in figure 6. The content of the dextro-antofloxacin in the antofloxacin hydrochloride tablets is calculated according to a self control method, and the result is 0.053 percent and the RSD is 1.0 percent. (wherein, the content of the dextro-antofloxacin = (peak area of the dextro-antofloxacin test sample/peak area of the levo-antofloxacin control solution) × 100%).
In conclusion, the separation of levo-antofloxacin and dextro-antofloxacin is realized by optimizing HPLC chromatographic conditions and adopting a Fenomei 3126 (D) -penicillamine chiral chromatographic column, and the adopted chromatographic conditions have the advantages of good separation effect, small interference, high speed, good repeatability of detection results, high precision and low detection limit; the resolution method can also be used for measuring the content of the dextroisomer in the antofloxacin hydrochloride tablets, so that the dextroisomer in the antofloxacin hydrochloride tablets can be strictly controlled, and the quality of the antofloxacin hydrochloride tablets can be effectively monitored.
Finally, it should be emphasized that the above-described preferred embodiments of the present invention are merely examples of implementations, rather than limitations, and that many variations and modifications of the invention are possible to those skilled in the art, without departing from the spirit and scope of the invention.
Claims (5)
1. A method for splitting antofloxacin enantiomer by a chiral stationary phase method is characterized in that a mixed reference substance solution of levo-antofloxacin and dextro-antofloxacin is prepared, an HPLC method is adopted, a chiral column is used as a chromatographic column, and a copper sulfate solution-isopropanol is used as a mobile phase for analysis and detection; the volume ratio of the copper sulfate solution to the isopropanol in the mobile phase is 87-93;
the concentration of the copper sulfate solution is 2.8mmol/L;
the chromatographic column is a Fenomei 3126 (D) -penicillamine chiral chromatographic column with the specification of 250 multiplied by 4.6mm;
in HPLC detection, the wavelength is 301nm; the column temperature is 30-40 ℃; the sample injection amount is 20 mu L; the flow rate was 1.0 mL/min.
2. The method for resolving antofloxacin enantiomer by the chiral stationary phase method as claimed in claim 1, wherein the volume ratio of the copper sulfate solution to the isopropanol in the mobile phase is 87-90.
3. The method for resolving antofloxacin enantiomer by the chiral stationary phase method according to claim 1, wherein the preparation method of the mixed reference substance solution comprises the following steps: the method comprises the steps of precisely weighing a levorotatory antofloxacin reference substance and a dextrorotatory antofloxacin reference substance, placing the levorotatory antofloxacin reference substance and the dextrorotatory antofloxacin reference substance into a measuring bottle, adding a mobile phase for dissolving and diluting to prepare reference substance stock solutions containing the levorotatory antofloxacin and the dextrorotatory antofloxacin with the concentrations of 1000 mu g/mL respectively, and then taking a proper amount of the reference substance stock solutions to prepare mixed reference substance solutions containing the levorotatory antofloxacin and the dextrorotatory antofloxacin with the concentrations of 300 mu g/mL respectively.
4. Use of the method according to any one of claims 1 to 3 in quality detection of antofloxacin hydrochloride tablets.
5. The application of claim 4, wherein a proper amount of antofloxacin hydrochloride tablet samples are precisely weighed, placed in a measuring flask, added with the mobile phase solution for ultrasonic dissolution, filtered to obtain a test solution, and then detected by an HPLC method.
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