CN114660214B - Liquid chromatography detection method of semaglutin and application thereof - Google Patents
Liquid chromatography detection method of semaglutin and application thereof Download PDFInfo
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- CN114660214B CN114660214B CN202210152353.8A CN202210152353A CN114660214B CN 114660214 B CN114660214 B CN 114660214B CN 202210152353 A CN202210152353 A CN 202210152353A CN 114660214 B CN114660214 B CN 114660214B
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- 238000001514 detection method Methods 0.000 title claims abstract description 35
- 238000004811 liquid chromatography Methods 0.000 title claims abstract description 28
- 239000012535 impurity Substances 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000010828 elution Methods 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims abstract description 6
- 239000008055 phosphate buffer solution Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- UNXNGGMLCSMSLH-UHFFFAOYSA-N dihydrogen phosphate;triethylazanium Chemical compound OP(O)(O)=O.CCN(CC)CC UNXNGGMLCSMSLH-UHFFFAOYSA-N 0.000 claims description 6
- 230000002950 deficient Effects 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 4
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 claims description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 2
- 235000019800 disodium phosphate Nutrition 0.000 claims description 2
- 239000006012 monoammonium phosphate Substances 0.000 claims description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 claims description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 239000008363 phosphate buffer Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 11
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 14
- 230000014759 maintenance of location Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
- 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 1
- DLSWIYLPEUIQAV-UHFFFAOYSA-N Semaglutide Chemical compound CCC(C)C(NC(=O)C(Cc1ccccc1)NC(=O)C(CCC(O)=O)NC(=O)C(CCCCNC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CCC(NC(=O)CCCCCCCCCCCCCCCCC(O)=O)C(O)=O)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CCC(N)=O)NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)C(CC(C)C)NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(NC(=O)C(CC(O)=O)NC(=O)C(CO)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)C(NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)C(C)(C)NC(=O)C(N)Cc1cnc[nH]1)C(C)O)C(C)O)C(C)C)C(=O)NC(C)C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CCCNC(N)=N)C(=O)NCC(O)=O DLSWIYLPEUIQAV-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229950011186 semaglutide Drugs 0.000 description 1
- 108010060325 semaglutide Proteins 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000001195 ultra high performance liquid chromatography Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
A liquid chromatography detection method of semaglutin and application thereof belong to the technical field of pharmaceutical chemistry. The invention provides a liquid chromatography detection method of semaglutin, which comprises the following steps: phosphate buffer solution is used as a mobile phase A, a mixed solution of an organic solvent and water is used as a mobile phase B, a single chromatographic column is used as a stationary phase, a detector is an ultraviolet detector, and high performance liquid chromatography gradient elution of the semaglutin is adopted. The invention also provides application of the liquid chromatography detection method in detection and identification of impurities generated in the process of production or storage of the semaglutin. The method only needs to use common liquid chromatography, only needs one chromatographic column to finish the liquid chromatography detection of the semaglutin, and the detection number is large, the separation degree is high, and most of the detection numbers reach 1.5.
Description
Technical Field
The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a liquid chromatography detection method of semaglutin and application thereof.
Background
Semaglutide (CAS number 900463-68-2) is a new generation of long-acting GLP-1 analogues developed by Norand Norde corporation, is used for treating type II diabetes, has the effects of reducing blood sugar and protecting cardiovascular, and is the drug with the best blood sugar reducing and weight reducing effects in the current GLP-1 drugs.
During the production and storage of polypeptides, a series of impurities are produced, such as semaglutinin, which is prone to produce the following impurities during the production and storage: D-His 1 Racemized impurity, des-Aib 2 Defective impurity, plus-Gly 4 And (5) impurities. The presence of these impurities jeopardizes the patient's use, so a simple, fast and feasible detection method must be established to detect the quality of semaglutin.
At present, a technology for detecting semaglutin is disclosed, for example, CN201910685612 discloses an ultra-high performance liquid chromatography analysis method of semaglutin. However, the existing detection method has particularly high requirements on instruments and equipment and chromatographic columns, complex and complicated mobile phase matching, and has low separation degree on impurities and main peaks and between impurities.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to design and provide a liquid chromatography detection method of semaglutin and application thereof. Aiming at the physicochemical characteristics of the semaglutin, the invention provides the semaglutin detection method which has good separation effect, strong operability and low requirements on instruments and equipment and chromatographic columns.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a liquid chromatography detection method of semaglutin is characterized in that phosphate buffer solution is used as a mobile phase A, a mixed solution of organic reagent and water is used as a mobile phase B, a single chromatographic column is used as a stationary phase, a detector is an ultraviolet detector, and semaglutin is eluted by adopting a high performance liquid chromatography gradient.
The liquid chromatography detection method of the semaglutin is characterized in that the chromatographic column comprises a C18 reverse phase chromatographic column or a C8 reverse phase chromatographic column, preferably a C8 reverse phase chromatographic column.
The liquid chromatography detection method of the semaglutin is characterized in that the packed particle size of the chromatographic column is 3.5-10 mu m, and the packed particle size is preferably 3.5 mu m.
The liquid chromatography detection method of the semaglutin is characterized in that the phosphate buffer solution comprises at least one of triethylamine phosphate, monoammonium phosphate, dipotassium phosphate and disodium phosphate, preferably the phosphate buffer solution is triethylamine phosphate, and the organic reagent in the mobile phase B is at least one of acetonitrile, methanol, ethanol and isopropanol, preferably acetonitrile.
The liquid chromatography detection method of the semaglutin is characterized in that the volume ratio of the organic reagent to water in the mixed solution of the organic reagent and the water is 7:3-9:1, and the volume ratio of the organic reagent to the water is preferably 8:2.
the liquid chromatography detection method of the semaglutin is characterized in that the gradient range of the mobile phase B is 40-65%.
The liquid chromatography detection method of the semaglutin is characterized in that the column temperature is 25-35 ℃, preferably 30 ℃ in the gradient elution process, the flow rate is 0.4-0.8 mL/min, and the flow rate is preferably 0.7mL/min.
The liquid chromatography detection method of the semaglutin is characterized in that the wavelength of the ultraviolet detector is 220nm.
The liquid chromatography detection method of the semaglutin is applied to detection and identification of impurities generated in the process of producing or storing the semaglutin.
The use is characterized in that the impurity comprises D-His 1 Racemized impurity, des-Aib 2 Defective impurity, plus-Gly 4 And (5) impurities.
Compared with the prior art, the invention has the following beneficial effects:
1. the prior art requires the use of ultra-high liquid phase methods, and the method of the invention requires only the use of conventional liquid chromatography.
2. In the prior art, the chromatographic columns are used in combination, and only one chromatographic column is needed in the method.
3. The prior art has the defects of limited number of detected impurities, low separation degree, high detection number and high separation degree, and most of the impurities reach 1.5.
Drawings
FIG. 1 is a schematic diagram of the method of example 1 for detecting the presence of D-His 1 And Plus-Gly 4 Chromatograms of two impurity semaglutin samples;
FIG. 2 is a schematic diagram of example 2 application of the method to detect a protein containing D-His 1 、Des-Aib 2 And Plus-Gly 4 Chromatograms of three impurity semaglutin samples;
FIG. 3 is a prior art method of comparative example 1 for detecting a protein containing D-His 1 And Plus-Gly 4 Chromatograms of two impurity semaglutin samples.
Detailed Description
The following detailed description of the present invention will be made in detail to make the above objects, features and advantages of the present invention more apparent, but should not be construed to limit the scope of the present invention.
Example 1:
chromatographic conditions:
(a) Instrument: agilent 1260 high performance liquid chromatograph.
(b) Chromatographic column: agilent C18 column, 4.6 mm. Times.150 mm,3.5 μm.
(c) Detection wavelength: 220nm.
(d) Flow rate: 0.7mL/min.
(e) Sample injection amount: 20. Mu.L.
(f) Column temperature: 30 ℃.
(g) Acquisition time: 46min.
(i) Mobile phase a:50mmol/L triethylamine phosphate (pH 4.5); mobile phase B methanol water=9:1.
(j) Elution conditions: table 1 below.
TABLE 1 gradient elution
Separation effect: as shown in fig. 1 and table 2, 3 impurities were separated, and the degree of separation was greater than 1.5. Wherein the D-His is isolated at a retention time of 9.185min 1 Racemized impurity, plus-Gly is separated when retention time is 11.349min 4 And (5) impurities.
TABLE 2 high performance liquid chromatography detection results for example 1
Example 2:
chromatographic conditions:
(a) Instrument: agilent 1260 high performance liquid chromatograph.
(b) Chromatographic column: agilent C8 column, 4.6 mm. Times.150 mm,3.5 μm.
(c) Detection wavelength: 220nm.
(d) Flow rate: 0.7mL/min.
(e) Sample injection amount: 20. Mu.L.
(f) Column temperature: 30 ℃.
(g) Acquisition time: 46min.
(i) Mobile phase a:50mmol/L triethylamine phosphate (pH 4.5); mobile phase B acetonitrile, water=8:2.
(j) Elution conditions: table 3 below.
TABLE 3 gradient elution
Separation effect: as shown in fig. 2 and table 4, 4 impurities were separated, and the degree of separation was greater than 1.5. Wherein the D-His is isolated at a retention time of 9.178min 1 Racemization impurityThe Des-Aib is obtained by separating at 10.557min 2 Defective impurities, plus-Gly, are separated at a retention time of 12.269min 4 And (5) impurities.
TABLE 4 high performance liquid chromatography detection results for example 2
Comparative example 1:
chromatographic conditions:
(a) Instrument: ACQUITY CLASS-H (Wterse).
(b) Chromatographic column: the C8 column and the C4 column are connected in series.
(c) Detection wavelength: 214nm.
(d) Flow rate: 0.3mL/min.
(e) Sample injection amount: 20. Mu.L.
(f) Column temperature: 50 ℃.
(g) Acquisition time: 120min.
(i) Mobile phase a:10mmol/L sodium perchlorate and 1mmol/L potassium hexafluorophosphate, and regulating pH to 3.0 with perchloric acid; mobile phase B acetonitrile.
(j) Elution conditions: table 5 below.
TABLE 5 gradient elution
Separation effect: as shown in fig. 3 and table 6, 3 impurities were separated, and the degree of separation was less than 1.5. Wherein the D-His is isolated at a retention time of 18.759min 1 Racemized impurity, des-Aib is separated when retention time is 20.832min 2 Defective impurities, plus-Gly, are separated at a retention time of 23.582min 4 And (5) impurities.
TABLE 6 high performance liquid chromatography test results for comparative example 1
Claims (8)
1. A liquid chromatography detection method of semaglutin is characterized in that phosphate buffer solution is used as a mobile phase A, a mixed solution of organic reagent and water is used as a mobile phase B, a single chromatographic column is used as a stationary phase, a detector is an ultraviolet detector, and semaglutin is eluted by adopting a high performance liquid chromatography gradient;
the phosphate buffer solution comprises at least one of triethylamine phosphate, monoammonium phosphate, dipotassium phosphate and disodium phosphate;
the organic reagent is acetonitrile or methanol;
the chromatographic column comprises a C18 reverse phase chromatographic column or a C8 reverse phase chromatographic column;
the volume ratio of the organic reagent to the water in the mixed solution of the organic reagent and the water is 7:3-9:1;
the column temperature is 25-35 ℃ and the flow rate is 0.4-0.8 mL/min in the gradient elution process;
the wavelength of the ultraviolet detector is 220 nm;
the liquid chromatography detection method is used for detecting the semaglutin and the D-His in the semaglutin 1 Racemized impurity, des-Aib 2 Defective impurity, plus-Gly 4 Impurities;
the conditions of the gradient elution are as follows:
。
2. The method for detecting a semaglutin liquid chromatography according to claim 1, wherein said chromatographic column is a C8 reversed phase chromatographic column.
3. The method for detecting a semaglutin liquid chromatography according to claim 1, wherein the packed particle size of the column is 3.5 to 10 μm.
4. The method for liquid chromatography detection of semaglutin according to claim 1, wherein the packed particle size of the chromatographic column is 3.5 μm.
5. The method for liquid chromatography detection of semaglutin according to claim 1, wherein the phosphate buffer is triethylamine phosphate and the organic reagent is acetonitrile.
6. The method for detecting semaglutin by liquid chromatography according to claim 1, wherein the volume ratio of the organic reagent to water in the mixed solution of the organic reagent and water is 8:2.
7. The method for detecting the semaglutin by liquid chromatography according to claim 1, wherein the column temperature is 30 ℃ and the flow rate is 0.7mL/min in the gradient elution process.
8. Use of the liquid chromatography detection method of semaglutin according to any one of claims 1-7 for detecting and identifying impurities generated during the production or storage of semaglutin.
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| CN115326956B (en) * | 2022-08-09 | 2024-02-27 | 成都普康生物科技有限公司 | Separation detection method for homolog impurities in cable Ma Lutai modifier |
| CN116298027A (en) * | 2022-12-28 | 2023-06-23 | 江苏诺泰澳赛诺生物制药股份有限公司 | Liquid chromatography detection method and application of genotoxic impurities |
| CN116425858B (en) * | 2023-03-01 | 2024-04-19 | 浙江大学 | Fluorescence-modified semaglutin derivative and preparation method and application thereof |
| CN116500172B (en) * | 2023-06-29 | 2023-09-05 | 成都普康唯新生物科技有限公司 | Detection method of amine solvent in acidic substrate |
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| CN109456401A (en) * | 2018-12-03 | 2019-03-12 | 成都诺和晟泰生物科技有限公司 | A kind of synthetic method of Suo Malu peptide |
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