CN105021738B - Method for analyzing content of Abeta plaque imaging agent precursor AV-45-OTS through micellar electrokinetic chromatography - Google Patents
Method for analyzing content of Abeta plaque imaging agent precursor AV-45-OTS through micellar electrokinetic chromatography Download PDFInfo
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Abstract
The invention discloses a method for analyzing the content of Abeta plaque imaging agent precursor AV-45-OTS through micellar electrokinetic chromatography and belongs to the technical field of analytical chemistry. The content of the AV-45-OTS can be easily and conveniently measured through a capillary electrophoresis method. An effective analysis means is provided for controlling the quality of a drug box, which is not reported in correlational research. 1 mg of the AV-45-OTS is precisely weighed and dissolved in 0.5 mL of chromatographic pure tetrahydrofuran and 1.5 ml of 25 mmol/L borax-10 mmol/L SDS solution, sample injection at the voltage of 10 kv is performed, the voltage is kept unchanged, the sample injection time is changed, linear regression is performed on the sample injection time at the peak area, the linear relation is good when the sample injection time is 8-16 s, the regression equation is y=112958x-525878, and the correlation coefficient r2 is equal to 0.9909. Compared with HPLC, the micellar electrokinetic chromatography has the main advantages that separation efficiency is high, the efficiency can be 500,000 theoretical plate number/m and is ten times that of the HPLC; the micellar electrokinetic chromatography has other advantages that speed is high, the quantity of samples in use is small, consumption of reagents is small, and running cost can be reduced.
Description
Technical field
A kind of method that micella Electrokinetic Chromatography analyzes A β plaque block imaging agent precursor AV-45-OTS contents, belongs to point
Analysis technical field of chemistry.
Background technology
With Chinese population aging, Alzheimer disease (AD) increases year by year, become the elderly relaying cerebrovascular disease it
The second common neuropathy afterwards, has a strong impact on the old age quality of life of the elderly, brings huge to society and family
Financial burden.The pathogenesis of AD is failed to understand, currently without healing medicine.Correct diagnosis is only made in early days, is adopted an effective measure
Delay the state of an illness, the quality of life of the elderly could be improved, society and family's pressure is reduced.At present clinic thinks amyloid-beta
(β-amyloid protein, A β) aggregation is the major pathologic features of AD.Foreign countries adopt functional image intracerebral aβ protein patch
Aggregation carries out the diagnosis of early stage AD.At present FDA ratifies for clinical aβ protein patch imageable agents medicine box18F-AV45 is by the U.S.
Avid companies develop, and it can specifically bind A β plaque block, can be with significant difference by positron emission fault (PET) imaging
AD patient and the volunteer of cognitive health, such that it is able to early diagnose AD.
18F-AV45 is by labelled precursor (E) -2- (2- (2- (2- tolysulfonyl epoxide ethyoxyls) ethyoxyl) ethoxies
Base) -5- (4- tert-Butoxycarbonylmethyl aminostyryls) pyridine（AV-45-OTS）Jing18F marks are prepared from.
Highly purified kit is the key of PET clinical diagnosis medications.Obtain the PET developers of high top coal drawing18F-AV-
45, in addition to controlling flag condition, another key part is in complex sign precursor（AV-45-OTS）In strict control precursor
Purity, including reaction intermediate（AV-45-OH）Content, highly purified kit could be obtained.The purpose of the present invention is to build
A kind of vertical simply and easily Micellar Capillary Electrophoresis method determines the content of AV-45-OTS, is that the quality control of medicine box is provided with
The analysis means of effect, correlative study has no report.
The HPLC methods analysis AV-45 contents of document report, using acetonitrile:Ammoniom-Acetate (85:15) it is mobile phase, peak type is present
Conditions of streaking, peak is wider, it is impossible to efficiently separate impurity.The HPLC methods of improvement make buffer using phosphate, add three second
Amine improves conditions of streaking, but use of the salting liquid to chromatographic column and instrument has very high requirement.Due in AV-45-OTS structures
Containing BOC（Tertbutyloxycarbonyl protection group）And OTS（P-toluenesulfonyl）Two blocking groups so that molecular structure polarity drops significantly
Low, the analysis method such as common high performance liquid chromatography is relatively inaccessible to preferably separation.
The content of the invention
It is an object of the invention to provide a kind of analyze A β plaque block imaging agent precursor AV-45- using micella Electrokinetic Chromatography
The method of OTS contents.It is to set up the content that a kind of simply and easily capillary electrophoresis method determines AV-45-OTS, is medicine box
Quality control provides effective analysis means, and correlative study has no report.
Using micella Electrokinetic Chromatography（MECC）, with Surfactant SDS（SDS）It is added to boron
Sand buffer solution system forms micella, improves separating degree, has reached efficiently quickly separation detection.
Technical scheme：A kind of micella Electrokinetic Chromatography analyzes A β plaque block imaging agent precursor AV-45-OTS
The method of content, Micellar Capillary Electrophoresis analysis condition：Detection wavelength is 254nm, and ultraviolet detection, input mode is 10kv voltages
Sample introduction, 8～16s of sample injection time, separation voltage is 22kv, 25 DEG C of capillary column temperature, and running buffer is：25mmol/L boraxs-
10mmol/LSDS, pH=9.0, buffer solution and sample solution are filtered with 0.22 m micropores syringe filters；
From the 45cm × 50 m quartz capillary columns of non-coating；New capillaries post first successively with methyl alcohol flushing 10min, steams
Distilled water rinses 5min, and 1M NaOH solutions rinse 30min, distilled water flushing 5min, finally again with running buffer flushing 15min；
With distilled water and running buffer 2min is respectively rinsed before sample introduction successively；
Precision weigh sample AV-45-OTS 1mg be dissolved in 0.5mL chromatogram pure tetrahydrofuran+1.5mL 25mmol/L boraxs-
In 10mmol/L SDS solution, 10kv voltage sample introductions, keep voltage it is constant, change sample injection time, respectively 8s, 10s, 12s,
14s, 16s, the more long then sampling volume of sample injection time is more, repeats sample introduction three times, and sample injection time is linearly returned with peak area
Return, be as a result that linear relationship is good in the range of 8～16s in sample injection time, regression equation is y=112958x-525878, related
Coefficient r2= 0.9909。
Take be dried constant weight reference substance AV-45-OTS it is appropriate, it is accurately weighed, with the dissolving of 0.5mL chromatograms pure tetrahydrofuran+
1.5mL 25mmol/L borax -10mmol/L SDS are configured to the solution of AV-45-OTS 0.5mg/mL, are calculated as W controls, as
Contrast solution；Separately weigh sample in right amount, same procedure is configured to the solution containing tested AV-45-OTS samples 0.5mg/mL, is calculated as W
Sample, as sample solution；Determine by above-mentioned chromatographic condition, gained peak area is respectively S controls, S samples, by external standard method
The content of AV-45-OTS is in calculating sample：（S samples/S controls）×（W control/W samples）×100%.
Beneficial effects of the present invention：Compared with HPLC, the major advantage of micella Electrokinetic Chromatography is that separative efficiency is high,
Its efficiency can reach 500000 theoretical cam curves/m, be 10 times of HPLC.Another advantage is that speed is fast, amount of samples and reagent
Consume few, it is possible to decrease operating cost.
Description of the drawings
The Capillary Electrophoresis figure of Fig. 1 50mmol/L PBS-10mmol/L ammonium acetate dicyandiamide solutions.
The Capillary Electrophoresis figure of Fig. 2 25mmol/L borax buffer systems.
The Capillary Electrophoresis figure of Fig. 3 25mmol/L borax -10mmol/L SDS dicyandiamide solutions.
The Capillary Electrophoresis figure of Fig. 4 25mmol/L borax -10mmol/L CTAB dicyandiamide solutions.
The impact that Fig. 5 main peaks retention time changes with borate concentration.
Fig. 6 25mmol/L borax -10mmol/L SDS（pH=9.0）The Capillary Electrophoresis figure of dicyandiamide solution.
Fig. 7 retention times with voltage variation diagram.
Fig. 8 AV-45-OTS reference substance Capillary Electrophoresis chromatograms.
Fig. 9 intermediate A V-45-OH Capillary Electrophoresis chromatograms.
Figure 10 solvents tetrahydrofuranes（It is blank）Capillary Electrophoresis chromatogram.
Figure 11 AV-45-OTS Capillary Electrophoresis chromatograms.
Figure 12 AV-45-OTS calibration curves.
Specific embodiment
Embodiment 1, capillary is selected and pre-processed：
From the 45cm × 50 m quartz capillary columns of non-coating；New capillaries post first successively with methyl alcohol flushing 10min, steams
Distilled water rinses 5min, and 1M NaOH solutions rinse 30min, distilled water flushing 5min, finally again with running buffer flushing 15min；
With distilled water and running buffer 2min is respectively rinsed before sample introduction successively.
The impact of embodiment 2, sample solvent：
Sample AV-45-OTS compares indissoluble, can not be completely dissolved using methyl alcohol, this kind of organic solvent of acetonitrile, is completely dissolved
Add many this kind of organic solvents, sample introduction finds negative peak phenomenon occur, and repetition sample introduction is very unstable, is not suitable as sample molten
Agent.Sample can be completely dissolved using chromatogram pure tetrahydrofuran, and consumption is few.And tetrahydrofuran aprotic, Bu Huiying
The electrostatic interaction with micella is rung so as to affect the migration of solute.Consider sample solution in solvent must and running buffer
Dissolve each other, most at last sample tetrahydrofuran is diluted after dissolving with borate buffer solution for we.That is 1mg AV-45-OTS+0.5mL chromatograms
Sample introduction after pure tetrahydrofuran+1.5mL 25mmol/L borax -10mmol/L SDS dilutions, peak shape is preferable.
Embodiment 3, chromatographic condition optimizes：
The selection of 3.1 buffer systems
Knowable to Electrokinetic Chromatography distribution mechanism, there is distribution in solute, therefore change between micellar phase and mobile phase
Become buffer system to solute distribution coefficient, and then will produce impact to the retention of capacity factor measure and solute.Experiment is examined first
The species of buffer solution is examined, phosphate buffer (PBS), PBS- ammonium acetate systems, borax buffer system has been respectively adopted and is tested,
As a result show that AV-45-OTS main peak does not occur in PBS buffer systems；In PBS- ammonium acetate systems, there is obvious peak to occur, but
Peak shape is very wide, and has negative peak（See Fig. 1）；Using borax buffer system, there is obvious main peak, peak type is compared with PBS- ammonium acetates system point
It is sharp（Fig. 2）.Compared with PBS systems or PBS- ammonium acetate systems, peak type has very big improvement, therefore selects borax system to delay
Rush solution.
The selection of 3.2 surfactant types
Select certain surfactant to form micella in Electrokinetic Chromatography and be used as pseudo-stationary phase, pseudo-stationary phase
Select and change in HPLC fixing phase and there is identical effect, but the former is more easy.The selection of surfactant types exists
Electrokinetic Chromatography is extremely crucial in separating, and different surfactant systems will produce different interactions, make micella
Different solubility are produced to solute, while also making them there are different concentration class and shape, these factors will all affect solute
Distribution between pseudo-stationary phase and mobile phase is separated so as to affect it.
We are respectively adopted SDS, beta-schardinger dextrin, cetyl trimethyl quaternary amine bromine（CTAB）As pseudo-stationary phase test,
It was found that with beta-schardinger dextrin not appearance；CTAB is cationic surfactant, and because changing the symbol of Zeta electric potential electric osmose is result in
The change in stream direction so that appearance time is long and can not efficiently separate with impurity；SDS peak types are sharp, go out within 10min
Peak, and can efficiently separate with impurity（Fig. 3）.Therefore, we select SDS as the additive of Electrokinetic Chromatography.
3.3 the impact of borate concentration
The ionic strength of buffer solution has very important impact to detached selectivity.We select the mmol/L of concentration 10
SDS, and keep constant, the experiment of 10,15,20,25,30,35,40,45,50mmol/L boraxs is adjusted respectively, find borate concentration
Very big is affected on main peak retention time.When borate concentration is more than 50mmol/L, because electric current is too high, cause leakage of current, do not go out
Peak；, in 10mmol/L, because concentration is too low, electric current is unstable for borate concentration, sometimes almost without electric current.Main peak retention time
See Fig. 5 with the change of borate concentration.Consider, select borate concentration to be that 25mmol/L is more suitable.
The selection of 3.4 pH
In Electrokinetic Chromatography, pH value is a particularly important influence factor, and it is directly affected in electrokinetic chromatography
The speed of charge-carrying component migration.The net velocity of electric osmose is also relevant with pH.In pH=5, micella net velocity close to zero, component
Migration precision is poor；In pH<When 5, electric osmose very little, when it swims the speed for flowing less than micella, net flow direction can change.
Consider that AV-45-OTS contains two blocking groups, show stronger hydrophobicity, be unfavorable for that distribution is exchanged under low pH situations.Cause
We adjust pH in borax-SDS buffer systems and are respectively 6.0,7.0,8.0,9.0,10.0,11.0 tests this, as a result find
With moving after pH increases, when pH >=10, response accordingly diminishes appearance time.Therefore, consider, select pH to be 9.0 more
Properly（See Fig. 6）, main peak retention time is 8.968min.
The impact of 3.5 SDS concentration
Retention time of the solute in Micellar Capillary Electrophoresis is also affected by micellar concentration used.In critical micelle concentration
On, the increase of surfactant will increase the concentration of micella, equivalent to the amount or volume that increase fixer in HPLC；Work as SDS
When concentration reaches certain value and exceedes its critical micelle concentration, then molecular association forms ball-shape micella.For uncharged particle,
Retention time increases with the increase of micella content.It is different from the interaction of micella with different hydrophobic neutral particles,
So as to reach separation.The strong active force of hydrophobicity is just big, and the time stayed in micellar phase is just long, because micellar phase absolute velocity very
It is little, therefore the retention time of component is just long, conversely, more the resting in buffer solution of component is moved by the speed of electric osmose, retains
Time is shorter.Holding borate concentration is 25mmol/L, and SDS concentration is adjusted respectively for 5,10,15,25,50 mmol/L tests.When
When SDS concentration is 5mmol/L, peak type is too little；When SDS concentration select for 50mmol/L when, excessive concentration, not appearance；When SDS it is dense
Spend for 10mmol/L to 15mmol/L when, appearance time is between 8min to 10min, and peak type is preferable；Therefore, selection concentration is
10mmol/L SDS are the most suitable.Buffer system is 25mmol/L borax -10mmol/L SDS（See Fig. 6）.
The selection of the voltage of embodiment 4.
Voltage plays an important role as detached power in capillary electrophoresis separation.With the increasing of operating voltage
Plus, the absolute value of EOF and electrophoresis flow velocity degree all increases, and transit time shortens.Although the increase of electrophoresis flow velocity degree is with particle institute
It is electrically charged and different, but due to EOF speed typically much deeper than swimming flow velocity degree, the gross migration speed for therefore behaving as particle is accelerated.
Select buffer solution 25mmol/L borax -10mmol/L SDS mixed liquors（pH9.0）, investigate sample AV-45-OTS and
Separation situation of intermediate A V-45-OH under 10,15,20,22,25kv voltages, when voltage is more than 25kv, disengaging time contracting
It is short, but separating degree reduction, electric current is easily revealed, and unstability of base line is fixed.When voltage is less than 20kv, disengaging time is more long, experiment
Main peak and impurity peaks have suitable retention time and separating degree during middle selection 22kv.Retention time is shown in Fig. 7 with the change of voltage.
The specificity of the method for embodiment 5
Figure（8-11）For AV-45-OTS reference substances, AV-45-OTS samples, solvent four under the conditions of selected Capillary Electrophoresis
Hydrogen furans（It is blank）, intermediate A V-45-OH Capillary Electrophoresis chromatogram, under this experiment condition, AV-45-OTS and centre
Body is efficiently separated, and blank solvent does not disturb the measure of principal component.
Embodiment 6, linear relationship and test limit are determined
Precision weigh sample AV-45-OTS 1mg be dissolved in 0.5mL chromatogram pure tetrahydrofuran+1.5mL 25mmol/L boraxs-
In 10mmol/L SDS, 10kv voltage sample introductions, keep pressure it is constant, change sample injection time, respectively 8s, 10s, 12s, 14s,
16s, the more long then sampling volume of sample injection time is more, repeats sample introduction three times, and linear regression is carried out to sample injection time with peak area, ties
Fruit is that linear relationship is good in the range of 8～16s in sample injection time, and regression equation is y=112958x-525878, coefficient correlation
r2= 0.9909.It is in good linear relationship in the range of 8～16s to be in sample injection time（Calibration curve is shown in Figure 12）.Minimum detection
Measure as 0.05ng（S/N≥3）.
Embodiment 7, repeatability and accuracy are determined
The AV-45-OTS samples that mass concentration is 0.5mg/mL are taken, in the case where keeping voltage constant, changes sample introduction
Time, respectively 10s, 12s, 14s, 6 measure of continuous sample introduction calculate relative standard deviation RSD of peak area and retention time,
Repeatability and the accuracy under the conditions of this is investigated with this.The integral area RSD of three sample injection times is respectively 2.08%, 1.87%,
2.53%, retention time RSD is 0.86%, 0.42%, 0.57%.
Embodiment 8, sample amounts is analyzed
Take be dried constant weight reference substance AV-45-OTS it is appropriate, it is accurately weighed, with the dissolving of 0.5mL chromatograms pure tetrahydrofuran+
1.5mL 25mmol/L borax -10mmol/L SDS are configured to the solution of AV-45-OTS 0.5mg/mL, are calculated as W controls, as
Contrast solution.Separately weigh sample appropriate, same procedure is configured to containing tested AV-45-OTS samples 0.5mg/mL（W samples）It is molten
Liquid is used as need testing solution.Determine by above-mentioned chromatographic condition, gained peak area is respectively S controls, S samples, calculates by external standard method
The content of AV-45-OTS is in sample：（S samples/S controls）×（W control/W samples）×100%.
The sample determination result of table 1（n=3）
Claims (1)
1. a kind of method that micella Electrokinetic Chromatography analyzes A β plaque block imaging agent precursor AV-45-OTS contents, its feature exists
In：Micellar Capillary Electrophoresis analysis condition：Detection wavelength is 254nm, and ultraviolet detection, input mode is 10kv voltage sample introductions, is entered
8～16s of sample time, separation voltage is 22kv, 25 DEG C of capillary column temperature, and running buffer is：25mmol/L borax -10mmol/L
SDS, pH=9.0, buffer solution and sample solution are filtered with 0.22 m micropores syringe filters；
From the 45cm × 50 m quartz capillary columns of non-coating；New capillaries post is first successively with methyl alcohol flushing 10min, distilled water
5min is rinsed, 1M NaOH solutions rinse 30min, distilled water flushing 5min, finally again with running buffer flushing 15min；Sample introduction
It is front respectively to rinse 2min with distilled water and running buffer successively；
Precision weigh sample AV-45-OTS 1mg be dissolved in 0.5mL chromatogram pure tetrahydrofuran+1.5mL 25mmol/L boraxs-
In 10mmol/L SDS solution, 10kv voltage sample introductions, keep voltage it is constant, change sample injection time, respectively 8s, 10s, 12s,
14s, 16s, the more long then sampling volume of sample injection time is more, repeats sample introduction three times, and sample injection time is linearly returned with peak area
Return, be as a result that linear relationship is good in the range of 8～16s in sample injection time, regression equation is y=112958x-525878, related
Coefficient r2= 0.9909；Abscissa x is the sample injection time s seconds, and ordinate y is peak area；
Take be dried constant weight reference substance AV-45-OTS it is appropriate, it is accurately weighed, with 0.5mL chromatogram pure tetrahydrofuran dissolving+1.5mL
25mmol/L borax -10mmol/L SDS are configured to the solution of AV-45-OTS 0.5mg/mL, are calculated as W controls, molten as compareing
Liquid；Separately weigh sample in right amount, same procedure is configured to the solution containing tested AV-45-OTS samples 0.5mg/mL, is calculated as W samples,
As sample solution；Determine by above-mentioned chromatographic condition, gained peak area is respectively S controls, S samples, calculates by external standard method
The content of AV-45-OTS is in sample：（S samples/S controls）×（W control/W samples）×100%；
W is compareed and W samples point carve the concentration for representing reference substance solution and need testing solution, and unit is mg/mL.
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| CN101544584A (en) * | 2008-03-26 | 2009-09-30 | 中国医学科学院放射医学研究所 | Method for preparing precursor of Alzheimer disease imaging agent |
| CN103497217A (en) * | 2013-09-26 | 2014-01-08 | 北京师范大学 | 2-aryl benzothiazole compound with high affinity with A(beta) plaque and preparation method and application thereof |
| CN103645254A (en) * | 2013-11-28 | 2014-03-19 | 江苏省原子医学研究所 | Method for analyzing content of A beta plaque developer precursor AV45 |
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| CN101544584A (en) * | 2008-03-26 | 2009-09-30 | 中国医学科学院放射医学研究所 | Method for preparing precursor of Alzheimer disease imaging agent |
| CN103497217A (en) * | 2013-09-26 | 2014-01-08 | 北京师范大学 | 2-aryl benzothiazole compound with high affinity with A(beta) plaque and preparation method and application thereof |
| CN103645254A (en) * | 2013-11-28 | 2014-03-19 | 江苏省原子医学研究所 | Method for analyzing content of A beta plaque developer precursor AV45 |
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