CN108037220A - A kind of separation method of nucleosides and alkali radical species and its application - Google Patents
A kind of separation method of nucleosides and alkali radical species and its application Download PDFInfo
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- CN108037220A CN108037220A CN201810077898.0A CN201810077898A CN108037220A CN 108037220 A CN108037220 A CN 108037220A CN 201810077898 A CN201810077898 A CN 201810077898A CN 108037220 A CN108037220 A CN 108037220A
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- nucleosides
- radical species
- alkali radical
- separation method
- salt
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
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- 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
- G01N30/72—Mass spectrometers
Abstract
The invention discloses the separation method and its application of a kind of nucleosides and alkali radical species.The present invention separates nucleosides and alkali radical species using high performance liquid chromatography, the amino chromatographic column for the amide groups Bonded Phase that the chromatographic column in the high performance liquid chromatography is bonded for three keys；Mobile phase in the high performance liquid chromatography is salt-containing solution and polar organic solvent；The nucleosides and alkali radical species are adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine.The separation method is easy to operate, can be kept completely separate six kinds of nucleosides and alkali radical species, and peak shape is good, and is disturbed from other organic impurities, high sensitivity, simple and quick.
Description
Technical field
The present invention relates to the separation method and its application of a kind of nucleosides and alkali radical species.
Background technology
In the past 20 years, as the progress of biotechnology, nucleic acid series product, including nucleotide, nucleosides and its derivative obtain
To widely using.Wherein nucleoside compound illustrates the unique effect do not replaced in antiviral, anti-tumor aspect.The U.S.
Mostly it is nucleoside derivate in the anti-AIDS drug of FDA approvals.Nucleoside medicine is expected to become after sulfa drug and antibiotic
The medicine that a new generation afterwards plays an important roll.
For a new class of medicine, the research to its metabolite seems with monitoring to be even more important, especially nucleoside medicine
Metabolite be endogenous material.Adenine, guanine, cytimidine and uracil are the final of ribonucleic acid (RNA) metabolism
Product.Adenine, guanine, cytimidine and thymidine be DNA (DNA) metabolism final product, hypoxanthine
It is the intermediate product of RNA metabolism.
At present, measure nucleosides and alkali radical species mainly use high performance liquid chromatography, but there are problems with：Due to
Such compositional polarity is big, and general chromatographic column is extremely difficult to preferably retain, and appearance time is too early, larger by impurity peaks interference, point
It is poor from effect, especially for the Chinese medicine and prescribed preparation of complicated component, in order to reach separating effect, frequently with the stream of Gao Shuixiang
Dynamic phase, or containing ion-pairing agent be mobile phase, long-time service be easy to cause the decline of chromatographic column column effect, the lost of life.
Thus, in the case where chromatographic column not being lost, how fast and effeciently nucleosides and alkali radical species to be separated,
It is this area urgent problem to be solved.
The content of the invention
The technical problems to be solved by the invention are the existing method complexity for isolating and purifying nucleosides and alkali radical species, are deposited
Be difficult to reach in complex sample efficiently separate, chromatographic condition is harsh, long-time service is big to chromatographic column damage, peak shape is poor, sensitivity
The problems such as low, poor repeatability, so as to provide separation method and its application of a kind of nucleosides and alkali radical species.The separation method
It is easy to operate, a variety of nucleosides and alkali radical species can be kept completely separate, peak shape is good, and is disturbed from other organic impurities, spirit
Sensitivity is high, simple and quick.
The present invention provides a kind of nucleosides and the separation method of alkali radical species, it includes following steps：Using efficient liquid
Phase chromatography separates nucleosides and alkali radical species, you can；
The amino chromatographic column for the amide groups Bonded Phase that chromatographic column in the high performance liquid chromatography is bonded for three keys, example
Such as XBridge Amide columns；
Mobile phase in the high performance liquid chromatography is salt-containing solution and polar organic solvent；
The nucleosides and alkali radical species are adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine.
In the present invention, the species of salt can be the species used in mobile phase routine in this area, example in the salt-containing solution
Such as ammonium formate and/or ammonium acetate.
In the present invention, formic acid can be also contained in the salt-containing solution.The concentration of the formic acid can be that this area is conventional
Concentration, such as 0.1%, the percentage refers to percent by volume.
In the present invention, the concentration of salt can be the concentration of this area routine, such as 10mmol/L in the salt-containing solution.
In the present invention, the salt-containing solution can be the ammonium formate containing 5mmol/L, the ammonium acetate of 5mmol/L and 0.1%
Formic acid aqueous solution, the percentage refers to percent by volume.
In the present invention, 0.1% formic acid can be also contained in the polar organic solvent, the percentage refers to volume basis
Than.
In the present invention, the property of the amino chromatographic column for the amide groups Bonded Phase that the polar organic solvent can be bonded according to three keys
It can carry out conventional selection, such as acetonitrile.
In the present invention, the high performance liquid chromatography can use gradient elution, the brackish water during gradient elution
The volume ratio of solution and the polar organic solvent can be 8:92~50:50.
In the present invention, in the gradient elution, the mobile phase ratio changes with time scope can be as shown in table 1：
Table 1
Those skilled in the art know, in the gradient elution, in different time sections, the mobile phase linearly changes.
In the present invention, the adenosine, cytidine, guanosine, adenine, the sample of hypoxanthine and guanine are generally with solution shape
Formula exists.Solvent in the solution may be selected from aqueous solution or, the mixed solution of acetonitrile and water.
In the present invention, the conventional flow velocity when flow velocity of the mobile phase can be this area HPLC detection and analysis, such as 0.3~
1.5mL/min, then such as 0.4mL/min.
In the present invention, the sample size of the high performance liquid chromatography can be the conventional sample introduction of this area HPLC detection and analysis
Amount, the μ L of such as 1 μ L~5, then such as 2 μ L.
In the present invention, the filler particles degree of the chromatographic column can be the granularity of this area routine, such as 1.7 μm~5 μm,
In another example 3.5 μm.The length of the chromatographic column can be the length of this area routine, such as 50mm~250mm, in another example 100mm.
In the present invention, the column temperature of the chromatographic column can be the column temperature of this area routine, such as 25~40 DEG C, in another example 35
℃。
In the present invention, the high performance liquid chromatograph in the high performance liquid chromatography can use the conventional high-performance liquid of this area
Chromatography, such as 3000 liquid chromatographs of Thermo scientific DionexUltiMate.
Present invention also offers a kind of application of separation method in the analysis detection of nucleosides and alkali radical species, its
Comprise the steps of：High performance liquid chromatograph in the high performance liquid chromatography and detector are combined, to nucleosides and base
Class material carries out analysis detection, you can；Nucleosides and the alkali radical species are adenosine, cytidine, guanosine, adenine, hypoxanthine
And guanine.
In the application, the detector can be mass detector.
The mass detector can be the three-in-one combined high-resolution matter of quadrupole rod-electrostatic field orbit trap-linear ion hydrazine
Spectrometer, such as the Orbitrap Fusion Lumos mass spectrographs of Thermo Scientific.
Ion gun in the mass detector can use ESI ion guns.
It is described present invention also offers a kind of application of separation method in nucleosides and base class content of material measure
Alkali radical species are adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine.
The nucleosides and the method for measuring of base class content of material can be the content test method of this area routine.
The determinand of nucleosides and the alkali radical species can be possible fast containing adenosine, cytidine, guanosine, adenine, secondary Huang
The medium of purine and guanine, such as Pericarpium Trichosanthis injection.The Pericarpium Trichosanthis injection is limited for the first biochemical medicine company of Shanghai medicine-feeding
Company produces.
On the basis of common knowledge of the art, above-mentioned each optimum condition, can be combined, each preferably real up to the present invention
Example.
The reagents and materials used in the present invention are commercially available.
The positive effect of the present invention is：
(1) separation method provided by the invention is easy to operate, can be by adenosine, cytidine, guanosine, adenine, hypoxanthine
It is kept completely separate with guanine, peak shape is good, and is disturbed from other organic impurities, high sensitivity, simple and quick.
(2) separation method provided by the invention is except can be fast to adenosine, cytidine, guanosine, adenine, hypoxanthine and bird
Outside purine is separated, it can be additionally used in the analysis detection of adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine, also
It can be further used for the assay of adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine.
Embodiment
The present invention is further illustrated below by the mode of embodiment, but does not therefore limit the present invention to the reality
Apply among a scope.The experimental method of actual conditions is not specified in the following example, according to conventional methods and conditions, or according to business
Product specification selects.
The present invention is further illustrated below by the mode of embodiment, but does not therefore limit the present invention to the reality
Apply among a scope.The experimental method of actual conditions is not specified in the following example, according to conventional methods and conditions, or according to business
Product specification selects.
Embodiment 1
1st, the preparation of test sample
Take each reference substance of adenosine, cytidine, guanosine, adenine, hypoxanthine, guanine appropriate, it is accurately weighed, add water to be made
Concentration is the storing solution of 1mg/ml, and accurate each reference substance storing solution of absorption is diluted with water constant volume in right amount in same measuring bottle respectively
To scale, the mixed solution that concentration is 1 μ g/ml is obtained, with one times of dilution in acetonitrile up to nucleosides and base class material mixing reference substance
Solution,
2nd, chromatographic condition and method
Liquid chromatograph：Thermo-Fisher UltiMate 3000series high performance liquid chromatographs
Chromatographic column：ACQUITYXBridge Amide (100mm × 2.1mm, 3.5 μm)
Mobile phase：It is respectively with acetonitrile (containing 0.1% formic acid) and water (ammonium formate containing 5mM, 5mM ammonium acetates, 0.1% formic acid)
Mobile phase A and B.
Gradient elution：
Table 1
Column temperature：35℃；
Flow velocity：0.4mL/min；
Sample size：2μL；
Testing conditions：
Mass spectrograph：Quadrupole rod-three-in-one combined type high-resolution mass spectrometer (the UHPLC- of electrostatic field orbit trap-linear ion hydrazine
Orbitrap Fusion Lumos HRMS)
Electric spray ion source (ESI) positive ion mode detects, spray voltage 3.8KV, 350 DEG C of ion source temperature, sheath air-flow
Fast 35Arb, secondary air speed 10Arb, 350 DEG C of capillary temperature.First mass spectrometric data, mass range m/z70 are gathered using FT
~700, resolution ratio 120K, auto gain control (AGC) are 100 000, are split using high energy inducing lysis (HCD) mode
Solution, normalize collision energy 30%, using FT gather second order ms data, resolution ratio 30K, using " Top Speed " algorithms into
Row data dependence scans, and ionic strength is higher than 2.5e4Primary ion carries out two level fragmentation, and the dynamic exclusion time is 6s.
Data acquisition and processing (DAP) uses 4.0 softwares of Xcalibur.
3. testing result
The retention time of adenosine is 2.975min, and the retention time of cytidine is 6.154min, and the retention time of guanosine is
7.045min, the retention time of adenine are 3.512min, and hypoxanthic retention time is 4.631min, the reservation of guanine
Time is 5.413min.Separating degree is more than 1.5, and peak shape is good, does not trail, and does not protract.
Embodiment 2
1st, the preparation of test sample
Pericarpium Trichosanthis injection (the biochemical pharmaceutcal corporation, Ltd's production of Shanghai medicine-feeding first) 1ml is taken, 50ml is diluted with water to, mixes
It is even, with one times of dilution in acetonitrile, to obtain the final product.
2nd, chromatographic condition and method
With embodiment 1.
3. testing result
The retention time of adenosine is 2.975min, and the retention time of cytidine is 6.154min, and the retention time of guanosine is
7.045min, the retention time of adenine are 3.512min, and hypoxanthic retention time is 4.631min, the reservation of guanine
Time is 5.413min.Separating degree is more than 1.5, and peak shape is good, does not trail, and does not protract.
Comparative example 1
As different from Example 1, chromatographic column is replaced with into common C18 columns (Agilent poroshell 120SB-C18
2.7 μm, 3.0 × 75mm), mobile phase：With acetonitrile (containing 0.1% formic acid) and water (ammonium formate containing 5mM, 5mM ammonium acetates, 0.1% first
Acid) it is respectively mobile phase A and B.Following gradient elution mode is used at the same time：
Table 2
Other operate the mode of operation in equal reference implementation example 1, adenosine, cytidine, guanosine, adenine, hypoxanthine and bird
Purine cannot get baseline separation, and retain on a column poor, and retention time is within 1 minute.
Comparative example 2
As different from Example 2, Mobile phase B is replaced with into the aqueous solution containing 0.1% formic acid, while used with Gradient
Type of elution：
Table 3
Other operate the mode of operation in equal reference implementation example 2, adenosine, cytidine, guanosine, adenine, hypoxanthine and bird
Purine cannot get baseline separation.
Comparative example 3
1st, the preparation of test sample
With embodiment 2.
2nd, chromatographic condition and method
Liquid chromatograph：Waters Acquity Ultra-Performance LC-Synapt G2quadrupole
Time-of-flight (Q/TOF) LC-MS instrument (Waters, US)；
Chromatographic column：Waters Acquity UPLC HSS T3 chromatographic columns (2.1mm × 100mm, 1.8 μm), equipped with pre-column
WatersAcquity HSS T3VanGuard (2.1mm × 5mm, 1.8 μm)；
Mobile phase：With water (A) and acetonitrile (B) for mobile phase
Gradient elution：
Table 4
| Time (min) | Mobile phase B (%, v/v) |
| 0~2 | 5 |
| 2~12 | 5~40 |
| 12~18 | 40~90 |
| 18~21 | 90~5 |
| 21~25 | 5 |
Column temperature：45℃；
Flow velocity：0.3 ml/min；
Sample size：5μl；
Mass Spectrometry Conditions：It is respectively using electric spray ion source (ESI), positive and negative ion both of which measure, each parameter：Hair
Tubule voltage -2.5kV (ESI-) ,+3 kV (ESI+)；The V of taper hole voltage -25 (ESI-) ,+30 V (ESI+)；Ion source temperature
120℃；350 DEG C of desolvation temperature；50 L/h of taper hole throughput；600 L/h of desolventizing gas (N2) flow velocity；Argon gas is as collision
Gas；50~1500 Da of mass number detection range, low collision energy passage：4 eV；High collision energy passage：10~30 eV energy
Measure gradient.
3rd, testing result
The retention time of guanosine is 1.48min in nucleosides material, and the retention time of adenosine is 2.66min, is not separated
To cytidine；The retention time of xanthine is 1.22min in alkali radical species, and the retention time of adenine is 1.55min, is not separated
Obtain guanine；Guanosine does not obtain baseline separation with adenine.
Claims (10)
1. the separation method of a kind of nucleosides and alkali radical species, it is characterised in that it includes following steps：Using high-efficient liquid phase color
Spectrometry separates nucleosides and alkali radical species, you can；
The amino chromatographic column for the amide groups Bonded Phase that chromatographic column in the high performance liquid chromatography is bonded for three keys；
Mobile phase in the high performance liquid chromatography is salt-containing solution and polar organic solvent；
The nucleosides and alkali radical species are adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine.
2. the separation method of nucleosides as claimed in claim 1 and alkali radical species, it is characterised in that the three keys bonding
The amino chromatographic column of amide groups Bonded Phase is XBridge Amide columns；
The species of salt is ammonium formate and/or ammonium acetate in the salt-containing solution；
And/or the concentration of salt is 10mmol/L in the salt-containing solution.
3. the separation method of nucleosides as claimed in claim 1 and alkali radical species, it is characterised in that the salt-containing solution
And/or containing formic acid in the polar organic solvent, the concentration of the formic acid is preferably 0.1%, and percentage refers to volume hundred
Divide ratio.
4. the separation method of nucleosides as claimed in claim 1 and alkali radical species, it is characterised in that the adenosine, cytidine, bird
Glycosides, adenine, hypoxanthine and guanine exist in the form of a solution, the solvent in the solution for aqueous solution or, acetonitrile and water
Mixed solution；
The salt-containing solution is the aqueous solution of the ammonium formate containing 5mmol/L, the ammonium acetate of 5mmol/L and 0.1% formic acid,
The percentage refers to percent by volume；
And/or the polar organic solvent is acetonitrile.
5. the separation method of nucleosides as claimed in claim 1 and alkali radical species, it is characterised in that the high-efficient liquid phase color
Spectrometry uses gradient elution, and the volume ratio of salt-containing solution and the polar organic solvent described in during the gradient elution is
8:92~50:50.
6. the separation method of nucleosides as claimed in claim 1 and alkali radical species, it is characterised in that the stream of the mobile phase
Speed is 0.3~1.5mL/min, is preferably 0.4mL/min；
It is preferably 2 μ L and/or the sample size of the high performance liquid chromatography is the μ L of 1 μ L~5；
It it is preferably 3.5 μm and/or the filler particles degree of the chromatographic column is 1.7 μm~5 μm；
It is preferably 100mm and/or the length of the chromatographic column is 50mm~250mm；
It it is preferably 35 DEG C and/or the column temperature of the chromatographic column is 25~40 DEG C；
And/or the high performance liquid chromatograph in the high performance liquid chromatography is Thermo scientific
3000 liquid chromatographs of DionexUltiMate.
It is 7. a kind of if the separation method of claim 1~6 any one of them nucleosides and alkali radical species is in nucleosides and base class
Application in species analysis detection, it is characterised in that it includes following steps：By the efficient liquid in the high performance liquid chromatography
Chromatography is combined with detector, and analysis detection is carried out to nucleosides and alkali radical species, you can；Nucleosides and the alkali radical species
For adenosine, cytidine, guanosine, adenine, hypoxanthine and guanine.
8. application as claimed in claim 7, it is characterised in that the detector is mass detector, is preferably three-in-one group
The Orbitrap Fusion Lumos mass spectrographs of mould assembly high-resolution mass spectrometer, more preferably Thermo Scientific.
It is 9. a kind of if the separation method of claim 1~6 any one of them nucleosides and alkali radical species is in nucleosides and base class
Application in content of material measure, nucleosides and the alkali radical species are adenosine, cytidine, guanosine, adenine, hypoxanthine and bird
Purine.
10. application as claimed in claim 9, it is characterised in that the determinand of nucleosides and the alkali radical species is PERICARPIUM TRICHOSANTHIS
Parenteral solution.
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| CN108593807A (en) * | 2018-06-12 | 2018-09-28 | 大连民族大学 | A method of purine content in marine product is detected based on high performance liquid chromatography |
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| CN111351891A (en) * | 2020-05-06 | 2020-06-30 | 陕西中医药大学 | Method for detecting nucleoside and amino acid components in safflower |
| CN113552251A (en) * | 2021-07-01 | 2021-10-26 | 浙江义谱检验检测技术服务有限公司 | Method for detecting nucleotide in dietary supplement product based on nucleotide rapid nutrition supplement |
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| CN111351891A (en) * | 2020-05-06 | 2020-06-30 | 陕西中医药大学 | Method for detecting nucleoside and amino acid components in safflower |
| CN113552251A (en) * | 2021-07-01 | 2021-10-26 | 浙江义谱检验检测技术服务有限公司 | Method for detecting nucleotide in dietary supplement product based on nucleotide rapid nutrition supplement |
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