CN107621501A - The LC/MS/MS combination method detection kits of free fatty in serum - Google Patents
The LC/MS/MS combination method detection kits of free fatty in serum Download PDFInfo
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Abstract
The invention provides a kind of LC/MS/MS of free fatty in serum to be combined method detection kit, including quality-control product, Isotopic Internal Standard extract solution, dilution, conversion fluid, redissolution liquid and Mobile Phase Additives.This kit can detect a variety of free fatties simultaneously, and the used time is short, and detection efficiency is high.
Description
Technical field
The invention belongs to Mass Spectrometer Method field, and specifically, the present invention relates to the LC/MS/MS of free fatty in serum
Combination method detection kit and its application.
Background technology
Free fatty (Free Fatty Acid, FFA) is also known as non-esterified fatty acid (Non-esterified Fatty
Acid, NEFA), be adipose tissue lipid metaboli product, be made up of oleic acid, palmitic acid, linoleic acid etc., be the hydrolysis of triglycerides
Product, most of free fatty is combined with seralbumin to be present in blood.As the intermediate product of fat metabolism, dissociate
Aliphatic acid is the donor of Cell membrane lipids structure and prostaglandin synthesis, and one of important energy substance of human body.
Serum free fatty acid has been found the hair with the systemic disease such as cardiovascular and cerebrovascular, breathing, digestion, endocrine, immune
Raw, development and tumour and the traumatic energetic supersession that stress wait are in close relations, meanwhile, the metabolic disorder of free fatty with
The judgement of the diseases such as insulin resistance, hyperinsulinemia, hypertension, diabetes B plays the role of important.Free fatty
Antimer lipid metaboli that can be sensitive is metabolized, the detection of free fatty also contributes to the early diagnosis of coronary atherosclerosis
And assessment.In addition, free fatty (FFA) metabolic index can also distinguish benign breast cancer patient and healthy control group.
Therefore, human serum FFA qualitative, quantitative and quick measure, is respectively provided with to medical basic research and clinical examination
Important meaning.FFA method is more in measure serum at present, such as enzyme process, titration, colorimetric method, atom AAS, height
Liquid chromatography, gas chromatography etc. are pressed, the method for most of measure aliphatic acid is the gas phase by determining fatty acid methyl ester
Chromatography.And free fatty acid determination reagent kit existence and stability is bad in the market, measurement range is inconsistent, the range of linearity
The shortcomings of narrow.
In summary, this area there is an urgent need to develop new detection sensitivity it is higher and can simultaneous quantitative detection blood
The technology of free fatty in clear.
The content of the invention
It is an object of the invention to provide in a kind of serum free fatty LC/MS/MS combination method detection kit and
It is applied.
First aspect present invention, there is provided a kind of high performance liquid chromatography MS detection kit, including:
(1) quality-control product, the 5-8 kind free fatties being selected from the group are contained in the quality-control product:16 carbon monoenoic acids, 18
Carbon monoenoic acid, octadecadienoic acid, octatecatrienoic acid, 20 carbon monoenoic acids, eicosatetraenoic acid, eicosapentaenoic acid or two
Dodecahexaene acid;
(2) Isotopic Internal Standard extract solution, the Isotopic Internal Standard extract solution include methanol, ethyl acetate;
(3) dilution, described dilution are acetonitrile;
(4) conversion fluid, described conversion fluid are chloroacetic chloride and 3- pyridyl-methanamines;
(5) liquid is redissolved, described redissolution liquid is ethanol;With
(6) Mobile Phase Additives A, described Mobile Phase Additives A are saturated monocarboxylic acid.
In another preference, the kit also includes the part being selected from the group:(7) 96 hole reaction plates or (8) explanation
Book.
In another preference, described kit also includes:For establishing the bovine serum albumin(BSA) matrix of standard curve.
In another preference, the Mobile Phase Additives A is selected from the group:Formic acid, acetic acid, propionic acid, butyric acid or its group
Close.
In another preference, the Mobile Phase Additives A is formic acid.
Second aspect of the present invention, there is provided a kind of to be determined by high performance liquid chromatography MS in taken biological sample
The method of the amount of free fatty, including step:
(i) free fatty and internal standard are ionized by using APCI (APCI), produced respectively
The raw free fatty and the interior target at least one precursor ion;
(ii) produce respectively one or more fragments of precursor ion described in the free fatty and the interior target from
Son;With
(iii) the caused fatty acids metabolism thing and the interior target in comparison step (i) or (ii) or both
The amount of one or more ions is to determine the amount of the free fatty in the biological sample;
Wherein, methylamine is added in the mobile phase in chromatogram detection process.
In another preference, in the step (i), matter/lotus of the precursor ion is than be selected from the group one or more
It is individual:345.3、373.3、371.3、369.3、401.3、395.3、393.3、419.3、389.3、387.3、403.3、424.3.
In another preference, in the step (ii), the fragment ion include matter/lotus ratio be 92.0 ± 0.5 from
Son.
In another preference, in the step (ii), the fragment ion matter/lotus is than be selected from the group one or more
It is individual:92.0、92.1、92.2.
In another preference, the liquid chromatogram is eluted using gradient mode, and liquid phase chromatogram condition includes:
Chromatographic column:Synergi Polar-RP(2.0×50mm,5μm);
Column temperature:40℃;
Flow velocity:500μL/min;
Mobile phase A:By 1:Mobile Phase Additives A- formic acid is added to the aqueous solution by 1000 ratio;
Mobile phase B:By 1:Mobile Phase Additives A- formic acid is added to methanol solution by 1000 ratio.
It should be understood that within the scope of the present invention, above-mentioned each technical characteristic of the invention and have in below (eg embodiment)
It can be combined with each other between each technical characteristic of body description, so as to form new or preferable technical scheme.As space is limited, exist
This no longer tires out one by one states.
Brief description of the drawings
Fig. 1 is 16 carbon monoenoic acid canonical plottings.
Fig. 2 is 18 carbon monoenoic acid canonical plottings.
Fig. 3 is octadecadienoic acid canonical plotting.
Fig. 4 is octatecatrienoic acid canonical plotting.
Fig. 5 is 20 carbon monoenoic acid canonical plottings.
Fig. 6 is eicosatetraenoic acid canonical plotting.
Fig. 7 is eicosapentaenoic acid canonical plotting.
Fig. 8 is docosahexaenoic acid canonical plotting.
Embodiment
The present inventor and in-depth study, is surprised to find that a kind of LC/ of free fatty in serum first by extensive
MS/MS is combined method detection kit.The present invention is completed on this basis.
Term explanation
Unless otherwise defined, otherwise whole technologies used herein are respectively provided with such as art of the present invention with scientific terminology
The identical meanings that are generally understood that of those of ordinary skill.
As used herein, in use, term " about " means that the value can be from enumerating in the numerical value specifically enumerated is mentioned
Value, which changes, is not more than 1%.For example, as used herein, statement " about 100 " include 99 and 101 and between whole values (for example,
99.1st, 99.2,99.3,99.4 etc.).
As used herein, term " containing " or " including (including) " can be open, semi-enclosed and enclosed.Change
Yan Zhi, the term also include " substantially by ... form " or " by ... form ".
Detection method:LC/MS/MS analysis methods
As used herein, " liquid chromatography " (LC) refers to when fluid is equably by the post or logical of trickle separated material
The method of one or more compositional selectings delay of fluid solution when crossing capillary channel filtering.Delay is due to when the fluid phase
The component of mixture is in one or more stationary phases and bulk fluid (bulk fluid) during for stationary phase (or multiple) movement
Distribution between (i.e. mobile phase)." liquid chromatography " includes Reversed-phase liquid chromatography (RPLC), high performance liquid chroma- tography (HPLC) and height
Turbulent flow liquid chromatography (HTLC).
As used herein, " mass spectrography " (MS) refers to the analytical technology of the Quality Identification compound by them.MS technologies
Generally comprising (1) makes compound be ionized to form charging cpd;(2) detect the molecular weight of charging cpd and calculate matter lotus
Than (m/z).Compound can be ionized and detected by any suitable means." mass spectrograph " generally comprises electro-dissociator and ion detection
Device.
In the present invention, using the isotope of free fatty as internal standard, sample is extracted using derivative reagent:First passing through addition has
Machine reagent extracts to free fatty, then adds derivative reagent chloroacetic chloride and 3- pyridyl-methanamines are derived, and forms pyrrole
After acridine compound carries out electro-spray ionization processing, using liquid chromatography-tandem mass spectrometry instrument directly to the free-fat in sample
Acid is detected.
Record chromatogram and detect peak area and the internal standard peak area of sample free fatty, and calculate free fatty and
The ratio of its internal standard peak area, standard song is drawn with peak area ratio (y) by indicating concentration (x) to reference substance free fatty
Line and fit standard curvilinear equation, then the ratio of the peak area of the free fatty of sample to be tested and internal standard peak area is substituted into and intended
The calibration curve equation of conjunction, you can calculate the concentration of the free fatty in sample.
Detection method
It is prepared by one, internal standards extract solution:
The amount of Isotopic Internal Standard extraction working solution is calculated according to this test specimen amount, by 1:100 put forward the internal standard of concentration
Take liquid to be diluted with dilution, pay attention to fully mixing.
Extraction:Take 100 μ L human serums to add in 500 μ L internal standard extract solutions, centrifuged after fully mixing, then pipette supernatant
Into 96 hole reaction plates, nitrogen drying.
It is derivative:100 μ L conversion fluid is added into 96 hole reaction plates of drying, after fully mixing, room temperature derives 1 hour.
Redissolve:Add 50 μ L and redissolve liquid, fully mix.
Two, liquid-phase conditions
1. chromatographic condition
(1) chromatographic column:Synergi Polar-RP(2.0×50mm,5μm)
(2) mobile phase:
Mobile phase A:By 1:Mobile Phase Additives A- formic acid is added in the aqueous solution by 1000 ratio.
Mobile phase B:By 1:Mobile Phase Additives A- formic acid is added in methanol solution by 1000 ratio.
(3) flow velocity:500μL/min
(4) column temperature:40℃
(5) gradient elution:0-0.1min:Mobile phase B is 30%;0.1-5.5min:Mobile phase B is 30%-98%;5.5-
6.5min:Mobile phase B is 98%;6.5-6.51min:Mobile phase B is 98%-30%;6.51-8.0min:Mobile phase B is
30%.
2. Mass Spectrometry Conditions
API3200, electric spray ion source (ESI), cation MRM scanning analysis.
Source parameters:Atomization gas (Gas 1):65psi;Gas curtain gas (CUR):25psi;Collision gas (CAD):6;Auxiliary adds
Hot gas (Gas2):60psi;Ion source voltage (IS):5500v;Ion source temperature (TEM):600 DEG C, Q1/Q3 ion channels are as follows
Shown in table 1, wherein Q1 is precursor ion mass-to-charge ratio, and Q3 is fragment ion mass-to-charge ratio:
Table 1
Compound | Q1(amu) | Q3(amu) |
16 carbon monoenoic acids | 345.3 | 92.0 |
18 carbon monoenoic acids | 373.3 | 92.2 |
Octadecadienoic acid | 371.3 | 92.2 |
Octatecatrienoic acid | 369.3 | 92.0 |
20 carbon monoenoic acids | 401.3 | 92.0 |
Eicosatetraenoic acid | 395.3 | 92.0 |
Eicosapentaenoic acid | 393.3 | 92.0 |
Docosahexaenoic acid | 419.3 | 92.0 |
Octadecadienoic acid-13C18 | 389.3 | 92.2 |
Octatecatrienoic acid-13C18 | 387.3 | 92.2 |
Eicosatetraenoic acid-d8 | 403.3 | 92.0 |
Docosahexaenoic acid-d5 | 424.3 | 92.1 |
Main advantages of the present invention are:
(1) kit of the invention can detect the content of free fatty in serum, and operating process is easy, the used time is short,
Detection sensitivity is high.
(2) the standard curve linear dependence of free fatty is high in this kit detection serum, therefore testing result is accurate
Degree is high.
All purpose instrument and reagent
1. all purpose instrument
Liquid chromatograph (Shimadzu Corporation LC), including solution transfer pump (LC-20AD), on-line degassing instrument (DGU-20A3),
Automatic sampler (SIL-20A HT), controller (CBM-20A), column oven (CTO-20A).
Mass spectrograph (API3200, Applied biosystems), electric spray ion source (ESI), quadrupole rod quality of connecting
Analyzer.
Data handling system is Analyst softwares (Applied biosystems, software version number 1.6.2).
Turbula shaker (Vortex-Genie 2, Scientific Industries, Inc);Small desk freezes at a high speed
Centrifuge (TGL-16M, Hunan instrument);Micro-analytical balance (XPE26, Mettler-Toledo Instrument (Shanghai) Co., Ltd.);It is ultrapure
Water dispenser (Millipore).Isothermal vibration instrument;Nitrogen evaporator;96 orifice plate oscillators.
2. kit forms
3. free fatty title
4. reagent
Methanol (Fisher Scientific, HPLC);Acetonitrile (Fisher Scientific, HPLC);(match is silent to fly formic acid
Generation that);Ethyl acetate (Fisher Scientific, HPLC);Dichloromethane (analyzes pure, the limited public affairs of Chinese medicines group chemical reagent
Department);Chloroacetic chloride (Sigma);3- pyridyl-methanamines;Water is ultra-pure water.
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention
Rather than limitation the scope of the present invention.The experimental method of unreceipted actual conditions in the following example, generally according to conventional strip
Part, such as Sambrook et al., molecular cloning:Laboratory manual (New York:Cold Spring Harbor
Laboratory Press, 1989) condition described in, or according to the condition proposed by manufacturer.Unless otherwise indicated, it is no
Then percentage and number are percentage by weight and parts by weight.
Embodiment 1:Human serum sample carries out the detection of free fatty
1. sample pre-treatments
(1) at room temperature, 100 μ L samples to be tested are accurately pipetted in 1.5mL centrifuge tubes;
(2) 50 μ L extract solutions 1 are added, vortex mixed 0.5min, add 600 μ L extract solutions 2;
(3) it is vortexed and mixes 5min, high speed centrifugation 5min;
(4) 400 μ L of supernatant liquid are shifted in another centrifuge tube, gentle N2Drying;
(5) 200 μ L conversion fluids 1, vortex mixed 1min are added, room temperature derives 30min;Gentle N2Drying;
(6) 200 μ L conversion fluids 2, vortex mixed 1min are added, room temperature derives 5min;Gentle N2Drying;
(7) 500 μ L are added and redissolves liquid (F5), vortex mixed 5min;
(8) LC-MS/MS sample introductions are analyzed.
2. standard curve sample preparation
This experiment is mainly used in the detection of 8 kinds of free fatties in clinically serum, and matrix is used as by the use of bovine serum albumin(BSA)
Standard curve is prepared, avoids matrix effect most possibly.
Table 2 below is the comparison of internal standard peak area of 8 kinds of compounds in methanol solution and bovine serum albumin(BSA), is not had substantially
There is difference, matrix effect is substantially absent from.
Table 2
Sample names | Blank | C3 | C2 | C1 | QCL | QCH |
C16:1 | 1.23E+07 | 1.38E+07 | 1.33E+07 | 1.03E+07 | 1.36E+07 | 1.10E+07 |
C18:1 | 5.45E+04 | 6.68E+04 | 5.32E+04 | 3.46E+04 | 5.62E+04 | 3.67E+04 |
C18:2 | 1.23E+07 | 1.38E+07 | 1.33E+07 | 1.03E+07 | 1.36E+07 | 1.10E+07 |
C18:3 | 2.89E+05 | 3.64E+05 | 3.42E+05 | 2.45E+05 | 3.42E+05 | 2.62E+05 |
C20:1 | 1.23E+07 | 1.38E+07 | 1.33E+07 | 1.03E+07 | 1.36E+07 | 1.10E+07 |
C20:4 | 5.45E+04 | 6.68E+04 | 5.32E+04 | 3.46E+04 | 5.62E+04 | 3.67E+04 |
C20:5 | 1.23E+07 | 1.38E+07 | 1.33E+07 | 1.03E+07 | 1.36E+07 | 1.10E+07 |
C22:6 | 4.18E+04 | 5.14E+04 | 4.13E+04 | 2.48E+04 | 4.48E+04 | 2.89E+04 |
3. quantitative analysis
The method for drafting of standard curve:Using the sign concentration of 8 reference substances as abscissa (x), with the reality of 8 reference substances
The ratio for detecting peak area and respective internal standard peak area is ordinate (y), draws standard curve.
The fitting of calibration curve equation:Sign concentration (x) is linearly returned with the peak area ratio (y) of 8 reference substances
Return.Regression equation can be obtained:Y=a+bx, wherein y are ordinate, and x is abscissa, and a is intercept, and b is slope.
Detect the calculating of sample results:The ratio of the actual peak area and internal standard peak area that detect sample is substituted into above-mentioned mark
Directrix curve equation, calculate the concentration of testing compound in detection sample.
The range of linearity of compound should include normal population concentration range, and the linear model in this research is given in table 3 below
Enclose.
Table 3
Compound | The range of linearity (uM) |
16 carbon monoenoic acids | 2~200 |
18 carbon monoenoic acids | 5~500 |
Octadecadienoic acid | 10~1000 |
Octatecatrienoic acid | 1~100 |
20 carbon monoenoic acids | 0.2~20 |
Eicosatetraenoic acid | 4~400 |
Eicosapentaenoic acid | 0.2~20 |
Docosahexaenoic acid | 2~200 |
Table 4 below is the concentration of 8 kinds of compounds in a patient:
Table 4
Compound | Concentration (μM) |
16 carbon monoenoic acids | 11.6 |
18 carbon monoenoic acids | 102.0 |
Octadecadienoic acid | 139.3 |
Octatecatrienoic acid | 14.9 |
20 carbon monoenoic acids | 1.9 |
Eicosatetraenoic acid | 13.1 |
Eicosapentaenoic acid | 0.8 |
Docosahexaenoic acid | 9.4 |
Fig. 1-Fig. 8 is respectively 16 carbon monoenoic acids, 18 carbon monoenoic acids, octadecadienoic acid, octatecatrienoic acid, 20
Carbon monoenoic acid, eicosatetraenoic acid, eicosapentaenoic acid, the canonical plotting of docosahexaenoic acid, it can be seen that standard is bent
Line linear dependence is high, and the testing result degree of accuracy is high.
All it is incorporated as referring in this application in all documents that the present invention refers to, it is independent just as each document
It is incorporated as with reference to such.In addition, it is to be understood that after the above-mentioned instruction content of the present invention has been read, those skilled in the art can
To be made various changes or modifications to the present invention, these equivalent form of values equally fall within the model that the application appended claims are limited
Enclose.
Claims (10)
- A kind of 1. high performance liquid chromatography MS detection kit, it is characterised in that including:(1) quality-control product, the 5-8 kind free fatties being selected from the group are contained in the quality-control product:16 carbon monoenoic acids, 18 carbon one Olefin(e) acid, octadecadienoic acid, octatecatrienoic acid, 20 carbon monoenoic acids, eicosatetraenoic acid, eicosapentaenoic acid or 22 Carbon acid;(2) Isotopic Internal Standard extract solution, the Isotopic Internal Standard extract solution include methanol, ethyl acetate;(3) dilution, described dilution are acetonitrile;(4) conversion fluid, described conversion fluid are chloroacetic chloride and 3- pyridyl-methanamines;(5) liquid is redissolved, described redissolution liquid is ethanol;With(6) Mobile Phase Additives A, described Mobile Phase Additives A are saturated monocarboxylic acid.
- 2. kit as claimed in claim 1, it is characterised in that the kit also includes the part being selected from the group:(7)96 Hole reaction plate or (8) specification.
- 3. kit as claimed in claim 1, it is characterised in that described kit also includes:For establishing standard curve Bovine serum albumin(BSA) matrix.
- 4. kit as claimed in claim 1, it is characterised in that the Mobile Phase Additives A is selected from the group:Formic acid, acetic acid, Propionic acid, butyric acid or its combination.
- 5. kit as claimed in claim 1, it is characterised in that the Mobile Phase Additives A is formic acid.
- 6. a kind of method that the amount of free fatty in taken biological sample is determined by high performance liquid chromatography MS, Including step:(i) free fatty and internal standard are ionized by using APCI (APCI), produces institute respectively State free fatty and the interior target at least one precursor ion;(ii) one or more fragment ions of precursor ion described in the free fatty and the interior target are produced respectively;With(iii) the caused fatty acids metabolism thing and the interior target are a kind of in comparison step (i) or (ii) or both Or the amount of a variety of ions is to determine the amount of the free fatty in the biological sample;Wherein, methylamine is added in the mobile phase in chromatogram detection process.
- 7. method as claimed in claim 6, it is characterised in that in the step (i), matter/lotus of the precursor ion is than choosing From the one or more of the following group:345.3、373.3、371.3、369.3、401.3、395.3、393.3、419.3、389.3、 387.3、403.3、424.3。
- 8. method as claimed in claim 6, it is characterised in that in the step (ii), the fragment ion includes matter/lotus ratio For 92.0 ± 0.5 ion.
- 9. method as claimed in claim 6, it is characterised in that in the step (ii), the fragment ion matter/lotus ratio is selected from The one or more of the following group:92.0、92.1、92.2.
- 10. method as claimed in claim 6, it is characterised in that the liquid chromatogram is eluted using gradient mode, liquid chromatogram Condition includes:Chromatographic column:Synergi Polar-RP(2.0×50mm,5μm);Column temperature:40℃;Flow velocity:500μL/min;Mobile phase A:By 1:Mobile Phase Additives A- formic acid is added to the aqueous solution by 1000 ratio;Mobile phase B:By 1:Mobile Phase Additives A- formic acid is added to methanol solution by 1000 ratio.
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