CN108107103A - The MS probe of glutamate receptor and its space distribution rule detection method in brain tissue - Google Patents
The MS probe of glutamate receptor and its space distribution rule detection method in brain tissue Download PDFInfo
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Abstract
Space distribution rule detection method the present invention relates to a kind of MS probe of glutamate receptor and its in brain tissue.The glutamate receptor MS probe is made of two parts, and a part is glutamic acid, the glutamic acid or N methylaspartic acids of the protection of N methylaspartic acids, tertiary butyl, and another part is fluorenes methoxy carbonyl acyl group group.The present invention using semiconductor nano material electrophilic group in generated photoelectron tunnel-effect and MS probe molecule under laser irradiation electron capture ability, light induced electron is captured by the lacked electron atom in electrophilic group and triggers the fracture of adjacent α chemical bond, different MS probe molecules generate identical 165.0702 Da of fragment ion m/z, and the quantitative comparison of different probe molecule space distribution can be realized by measuring signal strength size；MS probe molecule of the present invention can be combined with the given activity cavity of glutamate receptor, had the ability for penetrating blood-brain barrier, can be provided new approaches and new technology for drug screening.
Description
Technical field
The invention belongs to mass spectrum imaging fields, and in particular to a kind of glutamate receptor MS probe and high-resolution molecular imaging
Method.
Background technology
Mass spectrum imaging is a kind of using ion full scan and the novel molecular image method of image reconstruction technique, be can be applied to
Measure distribution and metabolic rule of the drug in different tissues.Due to mass spectrum be based on the measure to gaseous state charged ion, because
This neutral molecule will all be first converted into the electrically charged ion of gaseous state and carry out mass spectroscopy.However, the vaporization of different molecular and
Ionizability is different, therefore the quantitative relationship between its absolute mass signal intensity and content is poor, realizes different molecular
Mass spectrum quantitative analysis is always the insoluble problem of mass spectrum.
Conventional MALDI (Matrix Assisted Laser Desorption Ionization) is to pass through sample molecule
Protonation or deprotonation or form complex with metal ion and become cation or anion and carry out mass spectroscopy, by
Different with ionizability in the vaporization of various molecules, the quantitative relationship between absolute mass signal and content is bad.Tradition
Stable isotope labeling method can only solve the problems, such as quantitative analysis of the identical molecule in different samples, it is impossible to solve different points
Quantitative comparison problem between son, and the quantitative of different molecular is of great significance to the mass spectrum imaging of full scan.
The content of the invention
The present invention is in view of the deficiencies of the prior art, and it is an object of the present invention to provide the MS probe of a kind of glutamate receptor and its in brain
Space distribution rule detection method in tissue.
For achieving the above object, the technical solution adopted by the present invention is：
A kind of glutamate receptor MS probe, is made of two parts, and a part is glutamic acid, n-methyl-aspartate, uncle
The glutamic acid or n-methyl-aspartate of butyl protection, another part are fluorenes methoxy carbonyl acyl group group, and the MS probe divides
Subformula is shown below：
In said program, trigger specific chemical bond fission after the MS probe capture light induced electron, generate identical
Fragment ion m/z 165.0702Da.
Space distribution rule detection method of the above-mentioned glutamate receptor MS probe in brain tissue, includes the following steps：
1) Image Acquisition film is made in nano semiconductor material；
2) MS probe wiring solution-forming is injected in brain tissue, taking-up brain tissue is fabricated to tissue and cuts after a period of time
Histotomy is then attached on the Image Acquisition film of step 1) preparation, and Image Acquisition film is fixed on sample by piece
Target；
3) the low mass region quality of fatty acid mixt correction mass spectrograph negative ion mode is utilized；
4) sample target is put into sample bin, adjusts laser parameter and electrostatic field size, set the scanning model of mass analyzer
It encloses, the Image Acquisition film surface of histotomy is pasted with using laser beam flying, matter is measured by time-of-flight mass analyzer
Lotus ratio, signal strength is measured by detector, and obtaining spatial distribution of the MS probe in brain tissue by image reconstruction is imaged.
In said program, the detection method further includes：Step 5) detects the letter of each MS probe by detector
Number intensity carries out quantitative comparison according to signal strength size to spatial distribution of the different MS probe molecules in histotomy.
In said program, the nano semiconductor material is (Bi2O3)0.07(CoO)0.03(ZnO)0.9、AlN、SiO2、SiC、
ZnS、Bi2Te3、Bi2Se3Or Bi2S3。
In said program, the setting principle of the laser parameter is：It is big according to the property of nano semiconductor material and energy gap
It is small, correspondingly optical maser wavelength is selected, the energy gap of nano semiconductor material is made to be less than laser photon energy.
In said program, the electrostatic field is by sample target voltage, six grades of bar voltages, ion extraction voltage and slit voltage group
Into according to the property of nano semiconductor material and MS probe property setting sample target and slit voltage difference.
In said program, when using (Bi2O3)0.07(CoO)0.03(ZnO)0.9It is used to swash during nano semiconductor material
The a length of 355nm of light wave, sample target voltage are 87 volts, and slit voltage is 107 volts.The different laser wave of different material selections
Long, sample target voltage and slit voltage make the photoelectron of MS probe capture biphase interface transfer, and providing energy visits mass spectrum
The fracture of chemical bond further occurs for pin molecule, and the anion of gained moves in electrostatic field to high potential direction, through slit
With extraction pole, through six grades of bars and level Four bar focuses on and quality sorting.
In said program, the mass spectrum is full scan pattern.
Fluorenes methoxy carbonyl acyl group with strong Polarography is rolled into a ball and combined with glutamic acid, n-methyl-aspartate by the present invention
MS probe is formed, is advised using spatial distribution of the more different probe molecule of high-resolution molecular imaging method in brain tissue
It restrains, the electrophilic group in probe molecule has dual function, first, the photoelectricity using its lacked electron atom capture interfacial migration
Son triggers specific chemical bond fission, and different probe molecule is made to generate identical fragment ion m/z 165.0702Da, can be right
Spatial distribution of the different probe molecule in histotomy carries out quantitative comparison；It second is that can be with the specific work with glutamate receptor
Property cavity combine, inhibit the closing of S1 and S2 structural domains, and with passing through the ability of blood-brain barrier.This probe point will be injected
The mouse brain slice of son is attached at semiconductor nanomembrane surface, under the irradiation of Ultra-Violet Laser, due to this probe molecule
Trapped electron ability possessed by strong electrophilic group, light induced electron is by this electrophilic caused by Nanometer Semiconductor Films surface
Lacked electron atom capture in subbase group, and trigger the fracture of adjacent alpha-position chemical bond, different probe molecules generates identical
Fragment ion m/z 165.0702Da, these ions through entrance slit and extraction pole, using six grades of bars, level Four bar focus on
Afterwards, mass/charge ratio is measured by time-of-flight mass analyzer.Due to different probe molecules generate identical fragment from
Son, therefore distribution of the mass spectrum imaging method quantitative comparison different probe molecule in mouse brain can be used.Since mass spectrum is set as bearing
After ion mode has the function of that full scan, the method can also measure drug injection, the changing rule of other ions.
Required related reagent formula is as follows in MS probe high-resolution imaging method of the present invention：
1) preparation of MS probe solution：It chooses comprising 50mmol/L NH4HCO3Physiological saline for solvent, mass spectrum is visited
Pin dissolves, and it is 75mM to make its concentration.
2) preparation of Image Acquisition film：By (Bi2O3)0.07(CoO)0.03(ZnO)0.9Nano semiconductor material, which is positioned over, leads
On the aluminium strip or copper strips of electricity, Image Acquisition film is made under 10MPa pressure, and the Image Acquisition film of preparation is close to and consolidated
Due to metal sample target, the generation of bubble is avoided.
3) preparation of mass spectrograph negative ion mode mass calibration standard solution：Nine kinds of free fatties are included into C6：0, C8：
0, C10：0, C12：0, C14：0, C16：0, C18：0, C20：0 and C22：0 is dissolved in n-hexane so that these aliphatic acid it is dense
It spends for 5mg/mL.
4) preparation of mouse anesthesia and mouse brain cleaning solution：The anesthesia that pure 100% diethyl ether solution is used as mouse is analyzed, will be divided
It analyses pure NaCl to be dissolved in pure water, it is 0.9% to make its concentration, and the physiological saline of configuration is used for the cleaning of mouse external brain bloodstain, cold
Be hidden in -4 DEG C it is spare.
Heretofore described negative ion mode mass calibration method is as described below, by the Image Acquisition film of preparation tightly
It attaches and is fixed on sample target surface, the Fatty acid standards liquid of configuration is placed directly in Image Acquisition film table with liquid-transfering gun
Face, is put into high vacuum system after drying, setting laser, electrostatic field and mass analyzer parameter, scanning laser, caused by measure
Anion carries out the mass calibration of instrument using the accurate mass of each free fatty.
Beneficial effects of the present invention are as follows：
(1) compared with existing mass spectrum imaging method, the present invention is produced under laser irradiation using semiconductor nano material
Photoelectron tunnel-effect and MS probe molecule in electrophilic group electron capture ability, generate different probe molecules
Identical fragment ion, therefore can realize the quantitative comparison of different probe molecule space distribution；Simultaneously as quality analysis utensil
There is full scan function, the present invention can also measure the spatial distribution of other ions simultaneously, convenient for measuring caused by MS probe molecule
Histotomy in other ions the variation in spatial distribution；
(2) MS probe of the present invention can be combined with the given activity cavity of glutamate receptor, by comparing not homogeneity
Spatial distribution of the probe molecule in brain tissue is composed, a kind of new approaches and new technology can be provided for the screening of drug；
(3) glutamate receptor MS probe of the present invention is novel in design, simple and easy to get, used reagent green ring
It protects；Imaging method operating process of the present invention is simple and is easy to control, and analyze speed is fast, can reduce the inhibition effect of coexisting ion
Should be with the fuel factor of laser, radiationless and Pollution by Chemicals, spatial resolution is high, and mass accuracy is high, and reappearance is high, especially suitable
Together in the relevant drug screening of glutamate receptor.
Description of the drawings
Fig. 1 is that the mass spectroscopy molecular of aliphatic acid in 1 obtained mouse brain of embodiment is imaged, and mouse is not injected in embodiment 1
MS probe of the present invention.
Fig. 2 is MS probe molecular structure used in embodiment 2, is the tertiary fourth combined with fluorenes methoxy carbonyl acyl group group respectively
Base protects the tertiary butyl protection n-methyl-aspartate of glutamic acid and the combination of fluorenes methoxy carbonyl acyl group group.
Fig. 3 is the anion spectrogram of 2 gained of embodiment, and the abscissa of spectrogram is mass-to-charge ratio, and ordinate is signal strength.
Fig. 4 is 2 obtained MS probe of embodiment (tertiary butyl combined with fluorenes methoxy carbonyl acyl group group protects glutamic acid)
Imaging and spatial distribution of the aliphatic acid in mouse brain coexists.
Fig. 5 is MS probe molecular structure used in embodiment 3, is the paddy ammonia combined with fluorenes methoxy carbonyl acyl group group respectively
The n-methyl-aspartate that acid and fluorenes methoxy carbonyl acyl group group combine.
Fig. 6 is the imaging of 3 obtained MS probe molecule of embodiment (glutamic acid combined with fluorenes methoxy carbonyl acyl group group)
And spatial distribution of the aliphatic acid in mouse brain coexists.
Specific embodiment
For a better understanding of the present invention, with reference to the embodiment content that the present invention is furture elucidated, but the present invention
Content is not limited solely to the following examples.
Embodiment 1
The high-resolution molecular imaging of other endogenous materials in the mouse brain of MS probe was not injected, operating procedure is such as
Under：
1) preparation of Image Acquisition film：By (Bi2O3)0.07(CoO)0.03(ZnO)0.9Nano semiconductor material, which is positioned over, leads
On the aluminium strip or copper strips of electricity, Image Acquisition film is made under 10MPa pressure, the Image Acquisition film of preparation is close to and fixed
In metal sample target, the generation of bubble is avoided；
2) preanesthesia solution and preparation tissue-wash solution：Absolute ether is analyzed as anesthetic, weighs and analyzes pure NaCl,
It is dissolved in pure water, obtains the cleaning solution that physiological saline is used as murine brain bloodstain, refrigerate spare in -4 DEG C；
3) brain is taken out, with the physiological saline prepared by step 2) by after mouse anesthesia with the anesthetic that step 2) prepares
Clean bloodstain；
4) after mouse brain obtained by step 3) is freezed as freezing microtome section and fast-refrigerating point, 20 microns of thick thin slices are cut into；
5) histotomy obtained by step 4) is put into Image Acquisition film surface prepared by step 1), sample target is put into
Instrument is analyzed, and adjusts sample target, six grades of bars, extraction plate, slit voltage, it is 20 to make the voltage difference between sample target and slit
Volt；
6) laser parameter, scanning laser are set, laser photon energy should be greater than the energy gap of semi-conducting material；
7) by spectrogram C6 obtained by step 6)：0, C8：0, C10：0, C12：0, C14：0, C16：0, C18：0, C20：0 He
C22：0 exact mass is corrected；
8) molecular imaging of the brain endogenous substance of mouse：Scanning laser measures mass-to-charge ratio by time-of-flight mass analyzer, by
Detector measures signal strength, and gathered data obtains molecular imaging by image reconstruction.
The results are shown in Figure 1 for molecular imaging, as can be seen from Figure 1：The brain endogenous aliphatic acid of mouse can be carried with the present invention
The method of confession measures, and there is no the probe molecules of the present invention for mouse intracerebral.
Embodiment 2
MS probe (protect glutamic acid and rolled into a ball with fluorenes methoxy carbonyl acyl group and combined by the tertiary butyl combined with fluorenes methoxy carbonyl acyl group group
Tertiary butyl protection n-methyl-aspartate) spatial distribution imaging in mouse brain, operating procedure is as follows successively：
1) probe molecule solutions are prepared：Weigh respectively with fluorenes methoxy carbonyl acyl group group combine tertiary butyl protection glutamic acid and with
The tertiary butyl protection n-methyl-aspartate that fluorenes methoxy carbonyl acyl group group combines, is dissolved in containing 50Mm NH4HCO3Physiological saline
In, it is 75mM to make its concentration；
2) step 1) acquired solution is positioned over Image Acquisition film surface with pipettor, after solvent is evaporated completely, by sample
Product target is put into instrument and is analyzed, and adjusts sample target, six grades of bars, extraction plate, slit voltage, makes the electricity between sample target and slit
Pressure difference is 20 volts；
3) laser parameter, scanning laser are set, laser photon energy should be greater than the energy gap of semi-conducting material；It is in wavelength
Under the laser irradiation of 355nm, anion is generated after MS probe molecule capture photoelectron, obtains anion spectrogram；
4) by spectrogram C6 obtained by step 3)：0, C8：0, C10：0, C12：0, C14：0, C16：0, C18：0, C20：0 He
C22：0 exact mass is corrected, and obtains the spectrogram of two kinds of mass spectrum probe molecules in the negative ion mode.
Mass spectral results are as shown in figure 3, Fig. 3 illustrates to protect glutamic acid mass spectrum with the tertiary butyl that fluorenes methoxy carbonyl acyl group group combines
Probe and the tertiary butyl protection n-methyl-aspartate MS probe combined with fluorenes methoxy carbonyl acyl group group generate identical broken
Piece ion m/z 165.0702Da.The signal strength of different MS probes is detected by detector, according to signal strength size pair
Spatial distribution of the different MS probe molecules in histotomy is compared, it can be achieved that the distribution of different probe molecule space is determined
Amount compares.
The tertiary butyl combined obtained by step 1) with fluorenes methoxy carbonyl acyl group group is also protected glutamic acid mass spectrum by the present embodiment simultaneously
Probe solution by intravenous injection in mouse, after a time after, mouse brain is taken out and cleaned, then 20 are cut into freezing-microtome
Histotomy after micron；Gained histotomy is attached at Image Acquisition film surface, sample target is put into instrument is divided
Analysis adjusts sample target, six grades of bars, extraction plate, slit voltage, and it is 20 volts to make the voltage difference between sample target and slit；Setting
Laser parameter, scanning laser, laser photon energy should be greater than the energy gap of semi-conducting material；It is irradiated in the laser that wavelength is 355nm
Under, anion is generated after MS probe molecule capture photoelectron, obtains anion spectrogram；Use C6：0, C8：0, C10：0, C12：0,
C14：0, C16：0, C18：0, C20：0 and C22：0 exact mass is corrected anion spectrogram；It is finally brain endogenous to mouse
Substance carries out molecular imaging：Scanning laser measures mass-to-charge ratio by time-of-flight mass analyzer, and it is strong to measure signal by detector
Degree, gathered data obtain molecular imaging by image reconstruction.
The results are shown in Figure 4 for molecular imaging, as can be seen from Figure 4：The tertiary butyl combined with fluorenes methoxy carbonyl acyl group group is protected
Distribution of the glutamic acid in mouse brain can be measured with method provided by the invention, this probe molecule can pass through blood-brain barrier,
Reach the specific region of mouse brain.
Embodiment 3
MS probe molecule (glutamic acid combined with fluorenes methoxy carbonyl acyl group group and the N- first combined with fluorenes methoxy carbonyl acyl group group
Base-aspartic acid) spatial distribution imaging in mouse brain, operating procedure is as follows successively：
1) probe molecule solutions are prepared：Weigh respectively with fluorenes methoxy carbonyl acyl group group combine glutamic acid and with fluorenes methoxy carbonyl acyl
The n-methyl-aspartate that group combines, is dissolved in containing 50Mm NH4HCO3Physiological saline in, make its concentration be 75mM；
2) by MS probe solution obtained by step 1) by being injected intravenously in mouse；
3) mouse brain obtained by step 2) is taken out and cleaned, then 20 microns of thick histotomies are cut into freezing-microtome；
4) histotomy obtained by step 3) is attached at Image Acquisition film surface, sample target is put into instrument is divided
Analysis adjusts sample target, six grades of bars, extraction plate, slit voltage, and it is 20 volts to make the voltage difference between sample target and slit；
5) laser parameter, scanning laser are set, laser photon energy should be greater than the energy gap of semi-conducting material；It is in wavelength
Under the laser irradiation of 355nm, anion is generated after MS probe molecule capture photoelectron, obtains anion spectrogram；
6) by spectrogram C6 obtained by step 5)：0, C8：0, C10：0, C12：0, C14：0, C16：0, C18：0, C20：0 He
C22：0 exact mass is corrected；
7) mouse intracerebral MS probe molecule and the molecular imaging of other endogenous materials：Scanning laser, gathered data pass through
Image reconstruction obtains molecular imaging.
The results are shown in Figure 6 for the molecular imaging of glutamic acid MS probe combined with fluorenes methoxy carbonyl acyl group group, can be with from Fig. 6
Find out：Distribution of the glutamic acid combined with fluorenes methoxy carbonyl acyl group group in mouse brain can be measured with method provided by the invention, this
A probe molecule can pass through blood-brain barrier, reach the specific region of mouse brain.By compared with Fig. 4, can quantitatively judge with
The tertiary butyl that fluorenes methoxy carbonyl acyl group group combines protects glutamic acid than the probe molecule that no tertiary butyl is protected in identical mouse brain area
Domain has higher concentration.
Obviously, above-described embodiment is only intended to clearly illustrate made example, and is not the limitation to embodiment.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And the obvious variation or change therefore amplified
It moves within still in the protection domain of the invention.
Claims (9)
1. a kind of MS probe of glutamate receptor, which is characterized in that be made of two parts, a part for glutamic acid, N- methyl-
Aspartic acid, tertiary butyl protection glutamic acid or n-methyl-aspartate, another part be fluorenes methoxy carbonyl acyl group group, the matter
The molecular structural formula of spectrum probe is shown below：
2. the MS probe of glutamate receptor according to claim 1, which is characterized in that the MS probe capture photoproduction electricity
Trigger specific chemical bond fission after son, generate identical fragment ion m/z 165.0702Da.
3. space distribution rule detection side of the MS probe of any glutamate receptor of claim 1~2 in brain tissue
Method, which is characterized in that include the following steps：
1) Image Acquisition film is made in nano semiconductor material；
2) MS probe wiring solution-forming is injected in brain tissue, brain tissue is taken out after a period of time and is fabricated to histotomy, with
Histotomy is attached on the Image Acquisition film of step 1) preparation afterwards, and Image Acquisition film is fixed on sample target；
3) the low mass region quality of fatty acid mixt correction mass spectrograph negative ion mode is utilized；
4) sample target is put into sample bin, adjusts laser parameter and electrostatic field size, set the scanning range of mass analyzer, profit
The Image Acquisition film surface of histotomy is pasted with laser beam flying, mass-to-charge ratio is measured by time-of-flight mass analyzer,
Signal strength is measured by detector, obtaining spatial distribution of the MS probe in brain tissue by image reconstruction is imaged.
4. space distribution rule detection method of the MS probe of glutamate receptor in brain tissue according to claim 3,
It is characterized in that, the detection method further includes：Step 5) detects the signal strength of each MS probe, root by detector
Quantitative comparison is carried out to spatial distribution of the different MS probe molecules in histotomy according to signal strength size.
5. space distribution rule detection method of the MS probe of glutamate receptor in brain tissue according to claim 3,
It is characterized in that, the nano semiconductor material is (Bi2O3)0.07(CoO)0.03(ZnO)0.9、AlN、SiO2、SiC、ZnS、
Bi2Te3、Bi2Se3Or Bi2S3。
6. space distribution rule detection method of the MS probe of glutamate receptor in brain tissue according to claim 3,
It is characterized in that, the setting principle of the laser parameter is：According to the property of nano semiconductor material and energy gap size, phase is selected
Ground optical maser wavelength is answered, the energy gap of nano semiconductor material is made to be less than laser photon energy.
7. space distribution rule detection method of the MS probe of glutamate receptor in brain tissue according to claim 3,
It is characterized in that, the electrostatic field is made of sample target voltage, six grades of bar voltages, ion extraction voltage and slit voltage, according to
Property and MS probe property the setting sample target and slit voltage difference of nano semiconductor material.
8. space distribution rule detection method of the MS probe of glutamate receptor in brain tissue according to claim 3,
It is characterized in that, as use (Bi2O3)0.07(CoO)0.03(ZnO)0.9During nano semiconductor material, used optical maser wavelength is
355nm, sample target voltage are 87 volts, and slit voltage is 107 volts.
9. space distribution rule detection method of the MS probe of glutamate receptor in brain tissue according to claim 3,
It is characterized in that, the mass spectrum is full scan pattern.
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