CN101750449A - Lipoprotein capillary coating and the preparation method thereof - Google Patents
Lipoprotein capillary coating and the preparation method thereof Download PDFInfo
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- CN101750449A CN101750449A CN200810240105A CN200810240105A CN101750449A CN 101750449 A CN101750449 A CN 101750449A CN 200810240105 A CN200810240105 A CN 200810240105A CN 200810240105 A CN200810240105 A CN 200810240105A CN 101750449 A CN101750449 A CN 101750449A
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Abstract
The invention relates to a lipoprotein capillary coating and the preparation method thereof. The coating can be prepared with the physisorphtion and chemical bonding methods. In the physisorphtion, a noncovalent interaction between lipoprotein solution with a concentration ranging from 0.01 to 10mg/ml and the internal wall of a capillary is performed and the lipoprotein solution is self-assembled to the internal surface to form the coating. In the chemical bonding method, the capillary is modified with aminopropyl siloxane and the amino is introduced and then the glutaraldehyde or N, N-DSS or 1-ethide-3-(3-dimethyl aminopropyl)-carbodiimide/N-hydroxysuccinimide is used as the resin acceptor to covalently connect the amino on the capillary wall with the amino acid residues on the lipoprotein on the conditions of buffer solution with a pH ranging from 4 to 9 and lipoprotein with a concentration ranging from 0.1 to 10mg/ml for the purpose of obtain the lipoprotein coating. The coating preserves the biological activity, can be used for suppressing the absorption and electroosmotic adjustment on the surface of the capillary and also can be used for biochemical separation analysis.
Description
Technical field
The present invention relates to lipoprotein capillary coating and preparation method thereof, be applicable to that Capillary Electrophoresis and electrochromatography carry out biochemical compartment analysis, clinical diagnosis and environmental contaminants oxicity analysis.
Background technology
Capillary Electrophoresis (CE) and capillary electric chromatogram (CEC) technology are the products that the electrophoretic techniques with classics combines with modern microtrabeculae chromatographic separation technology, it makes analysis science enter from the microlitre level that to receive premium on currency flat, and makes single cell analysis and even single molecule analysis become possibility.In recent years, fast development along with life science and Environmental Health field, Capillary Electrophoresis and electrochromatographic technique show unique application advantage at aspects such as the Analysis and Identification of biomacromolecule (as the separating of protein, dna fragmentation and sequential analysis etc.), clinical disease diagnosis and clinical drug monitoring, metabolism research, pathological studies, and the parent who extensively wins researcher looks at.
Although CE and CEC technology have obtained the development of advancing by leaps and bounds current, along with deepening constantly and continuous upgrading that people require information accuracy, accuracy of scientific research purpose, this technology also is faced with more severe technological challenge.For example, biological sample or the complex matrices irreversible adsorption problem on kapillary is to carry out one of crucial difficult point that often runs into when relevant biomacromolecule is studied.Because the irreversible adsorption of biomacromolecule causes capillary wall surface zeta potential potential change, causes problems such as separating effect decline, poor reproducibility, accuracy reduction, even cause the loss of biological sample and kapillary to damage when serious.
In order to overcome this difficult problem, people have proposed some effective improvement measures, as adopting the electrophoresis buffer solution of high ionic strength, select extreme pH condition (pH＜2.5 or＞10), but the most generally accepted at present be the capillary coating scheme.The capillary coating technology mainly is meant methods such as adopting physics coating or chemical bonding, forms the method for one or more layers coating material at capillary tube inner wall.According to the preparation method and the application model of coating, capillary coating can be divided into dynamic coating and permanent coating.Surfactant and some polymkeric substance receive much concern as the capillary coating material.Yet most of reported method all can cause protein denaturation or loss of activity to some extent, becomes the blemish in an otherwise perfect thing in a lot of researchs.The scholar Lucy that Canadianizes has equaled development in recent years semi-permanent phosphide type coating in the separation efficiency and stability of satisfaction guaranted, has also been realized excellent biological compatibility, for this research field has been injected new vitality.Phosphatide is a kind of coating material with good biocompatibility, is furtherd investigate and reports in recent years.Yet the structure of good phospholipid bilayer coating structure highly depends on the coating condition, such as the size and the type of the phospholipid capsule bubble of self assembly formation, and this has limited the practical application of this method greatly.
Protein is a kind of natural endogenous, biocompatible biomacromolecule.Protein as the capillary coating material, except suppressing to adsorb and regulate and control the function of electric osmose, also will be produced a new function that using value is arranged, promptly be used as the testing tool of antibody and drug screening, clinical diagnosis.
The present invention is based on above-mentioned purpose, as coating material, adopt two kinds of methods of physics self assembly and chemical bonding to prepare to have the capillary coating of the active and biocompatibility of lipoprotein respectively with lipoprotein.Compare with phospholipid bilayer, the structure of lipoprotein coating is more simple, direct, good stability, and the coating function is also more wide.
Lipoprotein is the class transport protein in blood and the cell membrane, mainly is made up of liposome and apolipoprotein.Because the difference of its structure and density, supercentrifugation commonly used is divided into plasma lipoprotein: chylomicron (CM), very low density lipoprotein (VLDL) (VLDL), low-density lipoprotein (LDL), high-density lipoprotein (HDL) (HDL).The function of chylomicron is the transhipment ectogenous fat; The function of very low density lipoprotein (VLDL) is a transhipment endogenous fat; The function of low-density lipoprotein is the transhipment cholesterol; The function of high-density lipoprotein (HDL) is transhipment endogenous cholesterol and phosphatide.The function of lipoprotein is closely related with its structure.Most of lipoprotein is by formations such as phosphatide, apolipoprotein (as Apo B and Apo E etc.), cholesterol and cholesterol esters.With the low-density lipoprotein is example, and the phosphatide and the apolipoprotein (Apo B) that are distributed in molecular surface respectively account for 1/4 proportion in structure is formed.
Therefore, the present invention is fixed to different lipoprotein on the kapillary, both can suppress the irreversible adsorption brought by the silicon hydroxyl effectively, can carry out the applied research relevant with the lipoprotein function again.By experiment, show that tentatively lipoprotein coating transport mechanism and free radical in the biochemical compartment analysis of protein, environmental pollution object cause and have certain using value aspect the egg white injury.Correspondingly, think and also will have a good application prospect at aspects such as clinical diagnosis, antibody and drug screening, Environmental Health effect studies.
Summary of the invention
The present invention relates to lipoprotein capillary coating and preparation method thereof, its purpose is to develop a kind of big molecular coatings, and keep certain biologically active and biocompatibility, make it both to can be used for the inhibition and the electric osmose regulation and control of capillary surface absorption, can be used for concrete application such as biochemical analysis and clinical detection again.Lipoprotein comprises very low density lipoprotein (VLDL), low-density lipoprotein, high-density lipoprotein (HDL) and chylomicron.
Another object of the present invention is to provide the preparation method of above-mentioned lipoprotein coating, this method is simple to operate, is easy to keep the active and stable of lipoprotein.
The preparation of lipoprotein capillary coating involved in the present invention can be passed through two kinds of methods and realize, i.e. physisorphtion (or claiming self-assembly method) and chemical bonding.
The principle of physisorphtion (self-assembly method) preparation lipoprotein capillary coating: at certain density buffer solution (0.1-100mM, pH 4-9) and under temperature (4-37 ℃) condition, make noncovalent interactions such as lipoprotein (concentration 0.01-10mg/mL) is hydrophobic with the silicon hydroxyl generation of quartz or glass capillary inwall, electrostatic attraction, thereby self-assembling to inner wall surface forms binding layer; Use the unconjugated lipoprotein of damping fluid flush away then, make lipoprotein capillary coating.
Chemical bonding prepares the principle of lipoprotein capillary coating: earlier according to sol-gel technique, with silylating reagents such as gamma-aminopropyl-triethoxy-silane or γ-An Bingjisanjiayangjiguiwans kapillary is carried out modification, introduce amino reactive group, make amido modified kapillary; Then with excessive glutaraldehyde or N, N-succinyl amino-carbon acid esters (DSC) or disuccinimidyl suberate (DSS) or 1-ethyl-3-(3-dimethyl aminopropyl)-carbodiimides/N-hydroxy-succinamide system (EDC/NHS) are coupling agent, under the condition of certain pH value of buffer solution (pH 4-9), temperature (4-37 ℃) and lipoprotein concentration (0.1-10mg/mL), amino on the covalently bound kapillary and the amino acid residue on the lipoprotein are fixed to capillary tube inner wall with lipoprotein; Use the unconjugated lipoprotein of damping fluid flush away at last, make lipoprotein capillary coating.
Lipoprotein capillary coating involved in the present invention and preparation method have following characteristics: have excellent biological compatibility, be applicable to separation and the analysis of biomacromolecule; The activity that keeps lipoprotein can be simulated biological membrane and carry out repercussion study between itself and biomacromolecule, the micromolecule, can be used for clinical diagnosis and pharmacological research; Can come electric osmose is regulated and control by selecting electrophoretic buffer according to the isoelectric point (pI5-6) of lipoprotein; Have phosphatide and apolipoprotein isoreactivity component, can be the design of pharmaceutical carrier and the mechanism of the interior transportation of exogenous material body research tool is provided.
Description of drawings
Fig. 1 prepares the synthetic route synoptic diagram of lipoprotein coating for chemical bonding.
Fig. 2 is the graph of a relation that pH of buffer and low-density lipoprotein coating produce electric osmose.
Fig. 3 is used for the separate colors spectrogram of protein for lipoprotein capillary coating.
Embodiment
Lipoprotein capillary coating and preparation method thereof illustrates with following embodiment.
Before preparation lipoprotein coating, at first to carry out pre-service capillaceous.Kapillary is used chromatographically pure washed with methanol 1 hour earlier, and then with 1mol/L NaOH flushing 1-2 hour, washed with de-ionized water kapillary 15 minutes with 1mol/L hydrochloric acid flushing 1-2 hour, was used deionized water rinsing 15 minutes more at last, and high pure nitrogen dries up standby.After pre-service is finished, carry out the preparation of lipoprotein coating.
Embodiment 1 physisorphtion prepares the low-density lipoprotein capillary coating
Take by weighing the low-density lipoprotein freeze-dried powder of 5.0mg, fully be dissolved in the 25mmoL phosphate buffered solution (pH=7.4) of 5.0mL, be mixed with the coating solution of 1.0mg/mL.With this coating solution under 10psi pressure by through pretreated kapillary 15 minutes, seal the kapillary two ends with silicon rubber then, be perfused with above-mentioned low-density lipoprotein coating solution in the kapillary, under room temperature, left standstill 2-4 hour.The can coating solution is sealed the kapillary two ends once more, in leaving standstill more than 2 hours under the room temperature.After finishing aforesaid operations, washed kapillary 30 minutes, remove the low-density lipoprotein that does not combine with tube wall with 25mmoL phosphate buffered solution (pH=7.4), kapillary two ends silicone rubber seal, and place 4 ℃ of preservations in the refrigerator.
High-density lipoprotein (HDL), very low density lipoprotein (VLDL), chylomicron and mixing lipoprotein coating synthetic schemes are identical with aforesaid operations, only need the low-density lipoprotein coating solution is replaced to corresponding lipoprotein solutions.
The preparation capillaceous that embodiment 2 aminopropyls are modified
Pipette the γ-An Bingjisanjiayangjiguiwan of 0.1mL, be dissolved in the mixed solution of water (spirit of vinegar transfer pH 5)-methyl alcohol (2: 8, volume ratio) of 1.0mL, fully charge into rapidly in the pretreated kapillary behind the mixing, with kapillary two ends silicone rubber seal, reaction is 2-4 hour under the room temperature.After reaction was finished, successively with methyl alcohol, water flushing kapillary each 30 minutes, kapillary placed in 105-120 ℃ the baking oven ageing dry more than 2 hours under the high pure nitrogen protection then.By above-mentioned treatment step, obtain the kapillary that aminopropyl is modified.
Embodiment 3 is that the chemical bonding of coupling agent prepares the low-density lipoprotein capillary coating with the glutaraldehyde
Pipette the glutaraldehyde water solution of 0.5mL 50%, join in the 25mmoL phosphate buffered solution (pH=7.4) of 4.5mL, fully behind the mixing, under the pressure of 5psi, charge into by the aminopropyl of embodiment 2 preparations and modify kapillary, with silicone rubber seal kapillary two ends, be statically placed in room temperature reaction 2-6 hour after 1 hour.The glutaraldehyde solution of using 25mmoL phosphate buffered solution (pH=7.4) will react not most is then gone out, and obtains the kapillary of pentanedial decoration.
According to the low-density lipoprotein coating solution of the described method preparation of embodiment 1 1.0mg/mL, this solution is charged into above-mentioned in the kapillary that glutaraldehyde was handled, seal two ends after 30 minutes, continuation was reacted 2-4 hour under room temperature.In this course of reaction, the aldehyde radical generation covalent effect of lipoprotein and glutaraldehyde generates schiff bases formula compound.Going out with the lipoprotein coating solution that phosphate buffered solution will be reacted not most, is sodium cyanoborohydride solution (in the 25mmoL phosphate buffer, the pH 6.4) flushing 20 minutes of 0.5mg/mL again with concentration.With silicone rubber seal kapillary two ends, under room temperature, continue reaction 4-8 hour, unsettled schiff bases construction recovery is become more stable imine structure (seeing accompanying drawing 1).Use 25mmoL phosphate buffered solution (pH=7.4) that reactant liquor is gone out at last, obtain the capillary coating of low-density lipoprotein.As not using immediately, must place 4 ℃ of preservations of refrigerator.
High-density lipoprotein (HDL), very low density lipoprotein (VLDL), chylomicron and mixing lipoprotein coating synthetic schemes are identical with aforesaid operations, only need the low-density lipoprotein coating solution is replaced to corresponding lipoprotein solutions.
Embodiment 4 is with N, and N-succinyl amino-carbon acid esters (DSC) prepares the high-density lipoprotein (HDL) capillary coating for coupling agent
The DSC that takes by weighing 5.0mg is dissolved in the 5mL acetonitrile, fully mixing.Above-mentioned solution is charged into the aminopropyl that is prepared by embodiment 2 modify in the kapillary, use silicone rubber seal kapillary two ends after 20 minutes, and place 45 ℃ of water-baths reactions 2-4 hour.After question response is finished, use acetonitrile, deionized water and 25mmoL phosphate buffer (pH 7.4) flushing kapillary 10 minutes successively.
According to the high-density lipoprotein (HDL) coating solution of the described method preparation of embodiment 1 1.0mg/mL, this solution is charged into above-mentioned in the kapillary that DSC handled, under room temperature, reacted 2-4 hour.After question response is finished, washed kapillary 30 minutes, obtain the capillary coating (seeing accompanying drawing 1) of high-density lipoprotein (HDL) with 25mmoL phosphate buffer (pH 7.4).As not using immediately, must place 4 ℃ of preservations of refrigerator.
Low-density lipoprotein, very low density lipoprotein (VLDL), chylomicron and mixing lipoprotein coating synthetic schemes are identical with aforesaid operations, only need the high-density lipoprotein (HDL) coating solution is replaced to corresponding lipoprotein solutions.
Embodiment 5 is that coupling agent prepares the high-density lipoprotein (HDL) capillary coating with disuccinimidyl suberate (DSS)
It is identical with embodiment 4 with DSS to be that coupling agent prepares the operation of very low density lipoprotein (VLDL) capillary coating, only must be with N, and N-succinyl amino-carbon acid esters is replaced by DSS (seeing accompanying drawing 1).
Low-density lipoprotein, very low density lipoprotein (VLDL), chylomicron and mixing lipoprotein coating synthetic schemes are identical with aforesaid operations, only need the high-density lipoprotein (HDL) coating solution is replaced to corresponding lipoprotein solutions.
Take by weighing the very low density lipoprotein (VLDL) of 5.0mg, be dissolved in the 25mmoL phosphate buffer (pH 6.0) of 5mL; Add 2.0mg EDC and 3.0mg NHS in this solution successively, the whirlpool concussion is 5 minutes under the room temperature, leaves standstill 25 minutes.Above-mentioned solution is charged into the aminopropyl that is prepared by embodiment 2 modify in the kapillary, with silicone rubber seal kapillary two ends, 4 ℃-25 ℃ reactions are more than 4 hours after 15 minutes.After question response is finished, washed kapillary 30 minutes, obtain the capillary coating (seeing accompanying drawing 1) of very low density lipoprotein (VLDL) with 25mmoL phosphate buffer (pH 7.4).
High-density lipoprotein (HDL), low-density lipoprotein, chylomicron and mixing lipoprotein coating synthetic schemes are identical with aforesaid operations, only need the very low density lipoprotein (VLDL) coating solution is replaced to corresponding lipoprotein solutions.
By physisorption (self assembly) the type lipoprotein capillary coating of embodiment 1 preparation and the chemical bond mould assembly lipoprotein capillary coating of embodiment 3-5 preparation close electric osmose control behavior is arranged.By the lipoprotein capillary coating of above-mentioned embodiment preparation, can be according to the control of the difference realization of using electrophoretic buffer to electric osmose.The computing formula of electric osmose mobility is:
Electric osmose (cm
2/ Vs)=kapillary length overall (cm) * effective length (cm)/[voltage (V) * transit time (s)]
With physisorption type and chemical bond mould assembly low-density lipoprotein coating is example, selected experiment condition is: coatings capillary pipe internal diameter 50 μ m, length overall 50cm, effective length 40cm, apply voltage 15kV, with N, N '-dimethyl formamide (DMF) is the electric osmose label, sample introduction pressure 0.5psi, sample injection time 5 seconds.With this understanding, if with electrophoretic buffer (25mmoL phosphate buffer) pH value when 4 change to pH 8 gradually, the change (seeing accompanying drawing 2) of direction and order of magnitude will take place in the electric osmose mobility.And the intersection point of linear fit curve and X-axis (pH value) is between 5.3-5.5, and is approaching with the isoelectric point (pI is about 5.5) of low-density lipoprotein.
Experiment show the controllability of lipoprotein capillary coating to electric osmose.These characteristics can and be separated the operating parameter that purpose provides flexible and convenient for different analyses, thereby improve separation efficiency and analysis speed.
The biochemistry that embodiment 8 lipoprotein capillary coatings are used for protein separates and analysis
Adopt the low-density lipoprotein coating of chemical bonding preparation, pair cell pigment c (Cyt c), lysozyme (Lys), 4 kinds of basic proteins of ribonuclease A (RNase A) and the former A of Chymetin (α-Chy A) separate.Deposition condition: capillary inner diameter 50 μ m, length overall 50cm, effective length 40cm, applying voltage+15kV, is electrophoretic buffer with 25mmoL phosphate solution (pH 7.4), each protein concentration 0.2mg/mL in the biased sample, sample introduction pressure 0.5psi, sample injection time 5 seconds.The result shows, under above-mentioned deposition condition, more than 4 kinds of alkaline proteins reach complete electrophoretic separation, degree of separation is greater than 1.5 (seeing accompanying drawing 3).The separation efficiency of protein is 8700-124000 piece theoretical tray/rice, the recovery is between 82%-96%, in the daytime be 1.2%-5.7% (seeing Table 1) with withinday precision relative standard deviation (RSD), satisfy the requirement of biochemical separation of above-mentioned alkaline protein and qualitative and quantitative analysis.
Except that having hydrophobic and electrostatic interaction, also may there be certain affinity interaction between lipoprotein coating and the analyte.The lipoprotein coating has good architectural feature and biocompatibility, can Profilin matter etc. the irreversible adsorption of biomacromolecule on capillary wall, the biochemistry that is applicable to protein separates and analyzes.
The performance of table 1 low-density lipoprotein capillary coating electrophoretic separation protein
Embodiment 9 low-density lipoprotein capillary coatings are used for the research of free-radical oxidation micromechanism of damage
Adopt the low-density lipoprotein coatings capillary pipe, research bivalent cupric ion (Cu
2+) induce the free-radical oxidation of low-density lipoprotein to damage.Deposition condition: capillary inner diameter 50 μ m, length overall 50cm, effective length 40cm, apply voltage+15kV, with 25mmoL phosphate solution (pH 7.4) is electrophoretic buffer, is the electric osmose label with 0.2%DMF, each protein concentration 0.2mg/mL in the biased sample, sample introduction pressure 0.5psi, sample injection time 5 seconds.CuSO
4The preparation of solution: take by weighing the anhydrous cupric sulfate of 8.0mg (50 μ mol), be dissolved in the 25mmoL phosphate buffer (pH 7.4) of 10mL, be mixed with the CuSO of 5 μ mol
4Solution.The oxidative modification of low-density lipoprotein coating: with above-mentioned CuSO
4Solution pours respectively in 3 measure-alike low-density lipoprotein coatings capillary pipes, and sealing both ends places 37 ℃ of water-baths to hatch respectively 2,6 and 12 hours.After reaction is finished, will manage interior solution with electrophoretic buffer and go out, and continue flushing 20-30 minute, and insert capillary electrophoresis apparatus at last and carry out electric osmose mensuration and Separation of Proteins.
Measure electric osmose according to embodiment 7 described methods, carry out Separation of Proteins according to embodiment 8 described methods.The oxygenation efficiency of amounting to of lipoprotein represents with the relative variation of electroosmotic flow, i.e. [(Cu
2+Electric osmose after the oxidation-not oxidation electric osmose)/not oxidation electric osmose] * 100%.The result shows, bivalent cupric ion (Cu
2+) can induce the free-radical oxidation of low-density lipoprotein to damage, and along with also increase thereupon of oxygenation efficiency is amounted in the growth in processing time, the stability decreases of lipoprotein coating is to the also significantly reduction (seeing Table 2) of efficient of Separation of Proteins.
The oxidative modification of lipoprotein is one of main inducing that causes arteriosclerosis, and the existence of free radical can promote the oxidative damage of lipoprotein.Utilize lipoprotein capillary coating can carry out the research of damage of lipoprotein free-radical oxidation and arteriosclerosis pathogenesis.
Table 2Cu
2+Relation between the coating performance variation that causes and the free-radical oxidation of lipoprotein
Claims (5)
1. a lipoprotein capillary coating is characterized in that, capillary tube inner wall is fixed with one or more layers lipoprotein; Lipoprotein comprises high-density lipoprotein (HDL), low-density lipoprotein, very low density lipoprotein (VLDL) and chylomicron.
2. the preparation method of a lipoprotein capillary coating is characterized in that, can lipoprotein be fixed to capillary tube inner wall by the physisorption (or claiming self-assembly method) and the method for chemical bonding, forms lipoprotein capillary coating.
3. lipoprotein capillary coating according to claim 1 is characterized in that, has components such as phosphatide, apolipoprotein, cholesterol ester, remains with the activity of lipoprotein.
4. the method for lipoprotein capillary coating according to claim 2, it is characterized in that, the principle of physisorphtion (or claiming self-assembly method) is: at buffer solution (0.1-100mM, pH 4-9) and under temperature (4-37 ℃) condition, make noncovalent interactions such as lipoprotein (concentration 0.01-10mg/ml) is hydrophobic with the silicon hydroxyl generation of quartz or glass capillary inwall, electrostatic attraction, thereby self-assemble to inner wall surface, make lipoprotein capillary coating.
5. the method for lipoprotein capillary coating according to claim 2, it is characterized in that, the chemical bonding ratio juris is: adopt silylating reagents such as gamma-aminopropyl-triethoxy-silane or γ-An Bingjisanjiayangjiguiwan that kapillary is carried out modification earlier, introduce amino reactive group; Then with excessive glutaraldehyde or N, N-succinyl amino-carbon acid esters (DSC) or disuccinimidyl suberate (DSS) or 1-ethyl-3-(3-dimethyl aminopropyl)-carbodiimides/N-hydroxy-succinamide system (EDC/NHS) are coupling agent, under the condition of pH value of buffer solution (pH 4-9), temperature (4-37 ℃) and lipoprotein concentration (0.1-10mg/mL), amino on the covalently bound kapillary and the amino acid residue on the lipoprotein, thus lipoprotein is fixed to capillary tube inner wall.
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Application publication date: 20100623 |