CN109865315A - A kind of organic-inorganic hybrid mesoporous material coating preparation method as chromatographic stationary phases - Google Patents
A kind of organic-inorganic hybrid mesoporous material coating preparation method as chromatographic stationary phases Download PDFInfo
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Abstract
A kind of preparation method and application of the organic-inorganic hybrid mesoporous material coating as chromatographic stationary phases.The organic-inorganic hybrid mesoporous material coating is based on sol-gel method, using the silylating reagent with double bond as monomer, in capillary tube inner wall original position, controllable " growth " hybrid mesoporous coating;Then the method for using click chemistry, preparation have different hydrophobic chromatographic stationary phases.Compared with traditional capillary inner wall coating, organic-inorganic hybrid mesoporous material coating large specific surface area of the invention, with double bond abundant, significantly improve stationary phase key and density, separative efficiency can be effectively improved, improves column capacity, and coating thickness is controllable, to can easily be accommodated separating property, the separation of different hydrophobicity analysis objects can be used for.
Description
Technical field
The present invention relates to chromatographic stationary phases and separation analysis fields, including have different hydrophobic hybrid inorganic-organics
Mesoporous material and preparation method and application in chromatographic isolation field.
Background technique
Proteomics research played an important role in terms of disclosing biological phenomena, finding disease targets, mesh
Before have become one of hot spot of rear era gene life science (Mallick, P., Nat.Biotechnol., 2010,28,
695-709).However, proteomics research faces lot of challenges: (1) kinds of protein is various in complex biological system, and
There is also isomers and posttranslational modification for many protein;(2) concentration dynamic range is very wide, and many low abundance proteins are difficult to examine
It surveys;(3) certain sample sizes with researching value are extremely low.Therefore, develop high-resolution, highly sensitive protein stripping technique is carved
Do not allow to delay.
Nanoliter level chromatography-electrospray-ionization/mass spectrometry joint technology has few consumption sample amount, high resolution, sensitivity height etc. excellent
Point is currently widely used for the separation identification of protein, and gradually as one of the important tool of proteomics research (Lin
C.W.,Anal.Chem.,2016,88,8484-8494).Wherein, capillary separation column is one of critical component.Ultra-fine internal diameter hair
Tubule splitter (internal diameter is less than 20 μm) can significantly be mentioned guaranteeing the flow velocity for passing through reduction mobile phase in the case where efficiently separating
The Ionization Efficiency of high electrospray ionization mass spectrum, thus improve Mass Spectrometer Method sensitivity (Smith, R.D., Acc.Chem.Res.,
2004,37,269-278);Peak capacity can be improved in the length for increasing capillary separation column simultaneously, to improve to complex sample
Analysis ability.Therefore, the ultra-fine internal diameter capillary tube splitter of recent overlength is concerned in protein component from identification field.
Capillary open tubular column is using capillary inner surface coating as stationary phase, with preparation is simple, permeability is good, back-pressure
It is small, extremely adsorb the features such as small, be particularly suitable for trace samplings analysis.It is divided into polymer coating according to the property of coating, pure silicon glue applies
Layer and organic inorganic hybridization coating, wherein polymer has many advantages, such as that pH tolerance range is wide, is easy to modify, is vdiverse in function, still
Specific surface area is small, pore-size distribution is uneven (Forster S., J.Chromatogr.A, 2012,1265,88-94;Forster
S.,J.Chromatogr.A,2013 1315,127–134).Silica-gel coating has large specific surface area, and through-hole and mesopore size can
With independent regulation, and high mechanical strength, column effect is high, also has be widely applied very much at present, but that there are still mechanical strengths is low,
The disadvantage that easy swelling and aperture are difficult to control.Organic-inorganic hybridization monolithic column combines the advantages of the two, such as prepares simple, machine
Tool intensity is high, stability is good and large specific surface area etc., and the shortcomings that both overcome to a certain extent, therefore divides in chromatography
Play the role of from field very important.
Summary of the invention
The hybrid integral material large specific surface area of sol-gel method preparation, and have micropore, mesoporous and through-hole three-dimensional more
Grade pore structure, can meet the chromatographic isolation demand of small molecule and macromolecular.In addition, the material has high mechanical strength, chemistry steady
Qualitative good, good penetrability and the advantage for preparing favorable reproducibility." sulfydryl-double bond " click chemistry is utilized to react, in its surface modification
Different hydrophobic functional groups, realize efficiently separating for different analytes.Meanwhile it is simultaneous with mass spectrum through capillary column in incorporating ultrafine
Capacitive is good, high sensitivity advantage, has developed a kind of capillary column of ultra-fine internal diameter of overlength, for constructing nanoliter level liquid phase color
Spectrum-electrospray ionization mass spectrum system, to realize the hypersensitivity analysis of low abundance proteins in complex proteins sample.
To achieve the above object, the technical solution adopted by the present invention are as follows:
Based on sol gel reaction, hybridization mesoporous material is obtained in capillary tube inner wall in-situ polymerization.Then on the surface of the material
Different stationary phases are clicked, the ultra-fine capillary column of overlength is prepared, in conjunction with liquid phase-mass spectrometric hyphenated technique, efficient, highly sensitive analysis
Trace samplings.
Described has different hydrophobic organic-inorganic hybrid mesoporous materials, and specific preparation process is as follows:
(1) capillary surface activates: each leading into the lye, distilled water, the acid solution of pH<2, distilled water of pH>12, reacts
0.5~5h is dry;Wherein lye includes one of sodium hydroxide, potassium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate or two
Kind or more;Acid solution includes one or more of sulfuric acid, hydrochloric acid, nitric acid, acetic acid.
(2) preparation of organic-inorganic hybrid mesoporous material: sol gel reaction solution (v/v) is poured into capillary,
30~70 DEG C of reactions 5~for 24 hours.Wherein template includes ionic surfactant such as cetyltrimethylammonium bromide
(CTAB), cetyl chloride ammonium (CTAC), nonionic surface active agent such as P123, F127, F108, polyethylene glycol (PEG)
One or more of;Organic solvent includes ethyl acetate, acetone, dimethylformamide, ethyl alcohol, methanol, one in water
It plants and two or more;Catalyst includes formic acid, acetic acid, trifluoroacetic acid, propionic acid or ethamine, ethylenediamine, triethylamine;Vinyl front three
Oxysilane, allyltriethoxysilane, allyltrimethoxysilanis, 3- (trimethoxy first silicon substrate) propyl acrylate,
1- (trimethylsiloxy group) cyclohexene, bis- (triethoxy silicon substrate) one or both of ethylene and bridged silane reagent with
On.
The content of silylating reagent in sol gel reaction solution with double bond is 5~40% (v/v), catalyst
Content of rubbing is 1/100~1/10 times of monomer;The ratio of organic solvent and water is 1~50.
(3) click-reaction: the solution of click-reaction includes initiator, organic solvent, mercapto monomers;Initiator is AIBN;
Organic solvent includes one of ethyl acetate, acetone, dimethylformamide, ethyl alcohol, methanol and two or more;Mercapto monomers packet
Include one of glutathione, mercaptoethanol, butanethiol, spicy thioalcohol, Stearyl mercaptan and two or more.
Mercapto monomers content is 1/1000~1/100 in the solution of click chemistry reaction;The molar ratio of initiator and monomer
For 1%-10%.
(4) chromatographic column with the organic-inorganic hybrid mesoporous material of different hydrophobicitys that the method prepares, can
Separation analysis for biomolecule in proteomics.
The present invention has the advantage that
1. the present invention prepares hybridization mesoporous material coating using sol-gel method, layer thickness uniformity is good, and can pass through monomer
Concentration accurately controls material thickness.
2. hybridization mesoporous material prepared by the present invention has micropore, mesoporous and through-hole three-dimensional multistage pore structure, provides rich
Rich specific surface area effectively improves the volume containing the sample and separative efficiency of capillary open tubular column.
3. hybridization mesoporous material prepared by the present invention has double bond abundant with skeletal internal on the surface of the material, significantly mentions
High stationary phase key and density;Can click has different hydrophobic stationary phases, to make coat multifunctional.
Detailed description of the invention
The preparation flow figure of the hybridization mesoporous material of Fig. 1 Stearyl mercaptan modification;
Fig. 2 prepares the thickness controllability characterization of hybridization mesoporous material;
The influence that Fig. 3 material thickness separates trace BSA Peptides;
Fig. 4 material extracts the application in the separation of proteolysis peptide in trace HeLa.
Specific embodiment
Method provided by the invention is described in detail below by embodiment, but the invention is not limited in any way.
Embodiment 1
1, the preparation of hybridization mesoporous material
As shown in Figure 1, being prepared by following process:
1) capillary activates: being successively passed through 1M NaOH 2h, distilled water 10min, 1M HCl 2h, distilled water 10min.Most
After methanol rinses 30min afterwards, N2Drying overnight.
2) 5mg CTAC, 20 μ L water, 120 μ L methanol, 75 μ L BTSEY, 45 μ the preparation of hybridization mesoporous material: are accurately weighed
L VTMS, 5 μ L triethylamines pour into the capillary of activation, 40 DEG C of isothermal reaction 12h after mixing.After the reaction was completed, ethyl alcohol
Rinse 1h.
3) it is grafted the polymer brush of C18 functional group: accurately weighing 3mg AIBN, 20mg Stearyl mercaptan, 750 μ L second
Alcohol pours into the capillary of activation, 60 DEG C of isothermal reaction 12h after mixing.After the reaction was completed, ethyl alcohol rinses 1h.
2, influence of the monomer concentration for hybridization mesoporous material thickness
Polymerize in addition, different silylating reagent concentration are respectively adopted in 10 μm of capillaries, such as 10%, 15%,
20%, 25%, 30%, 35% (v:v) is measured thickness using scanning electron microscope.
Such as Fig. 2, according to electron microscope, thickness is uniform, and thickness has extraordinary linear increase relationship, this is mainly base
In both sides reason: on the one hand, monomer reaction efficiency is identical;On the other hand, ultra-fine interior fast through capillary inner transmission matter speed.Cause
This obtains the polymer brush thickness of needs by the control of monomer concentration.
3, ultra-fine internal diameter capillary tube column is analyzed for the separation of trace BSA Peptides
1) proteolysis sample preparation
1mg protein (BSA or HeLa extract albumen) is dissolved in 100 μ L 8M urea, it is molten that 8 μ L 1M DTT are added
Liquid, after mixing, 56 DEG C of denaturation 2h.0.0037g IAA is added after solution is cooling, is protected from light room temperature reaction 40min, after being settled to 1mL,
40 μ L 1M trypsase, 37 DEG C of enzymatic hydrolysis 12h are added.After sample centrifugation, desalination, freeze-drying are added 1mL water and redissolve peptide fragment, system
Obtain 1mg/mL protein digestion product.
2) difference thickness open tubular column efficiently separates trace standard protein enzymolysis product
By the capillary open tubular column of above-mentioned preparation, for the separation of 200pg BSA Peptides, as a result as shown in figure 3, showing
Preparation chromatographic column efficiently separates ability and high sensitivity.Thickness influences significantly the column effect of open tubular column, this is depended primarily on
Diffusion of the hydrophobicity and analyte of brush-type material in stationary phase.With the increase of material thickness, specific surface abundant is provided
Product, is conducive to the reservation of analyte.But monomer concentration continues growing, and will form integral material, permeability decline.Finally, it determines
Monomer concentration is 30%, is used to prepare capillary open tubular column.
Chromatographic condition: column length 1.5m;Flow velocity: 20nL/min;Gradient: 0-2min, 0-2%B;2-32min, 2-22%B;
32-34min, 22-80%B.The wherein aqueous solution (1 ‰ formic acid, v/v) of 2% acetonitrile of A phase, the aqueous solution (1 ‰ of 98% acetonitrile of B phase
Formic acid, v/v).
4, ultra-fine internal diameter capillary tube column extracts the separation analysis of proteolysis peptide for trace HeLa
Above-mentioned optimal capillary column is used for the separation of 25ng HeLa Peptides.As a result as shown in figure 4, identifying egg altogether
White 2000, there is very high column effect and sensitivity, the capillary column for illustrating that we prepare has in terms of trace samplings separation
There is extraordinary application prospect.
Chromatographic condition: column length 3m;Flow velocity: 20nL/min;Gradient: 0-2min, 0-2%B;2-32min, 2-22%B;32-
34min, 22-80%B.The wherein aqueous solution (1 ‰ formic acid, v/v) of 2% acetonitrile of A phase, aqueous solution (1 ‰ first of 98% acetonitrile of B phase
Acid, v/v).
Embodiment 2
As shown in Figure 1, preparing the ultra-fine capillary column of overlength by following process:
1) capillary activates: being successively passed through 1M NaOH 2h, distilled water 10min, 1M H2SO42h, distilled water 10min.Most
After methanol rinses 30min afterwards, N2Drying overnight.
2) 5mg CTAC, 20 μ L water, 120 μ L methanol, 75 μ L BTSEY, 45 μ the preparation of hybridization mesoporous material: are accurately weighed
L VTMS pours into the capillary of activation, 40 DEG C of isothermal reaction 12h after mixing.After the reaction was completed, ethyl alcohol rinses 1h.
3) it is grafted the polymer brush of C18 functional group: accurately weighing 3mg AIBN, 20mg HSC18, 750 μ L ethyl alcohol, mixing is equal
After even, the capillary of activation, 60 DEG C of isothermal reaction 12h are poured into.After the reaction was completed, ethyl alcohol rinses 1h.
The ultra-fine internal diameter capillary tube column of the overlength of preparation obtains the effect of column similar in embodiment 1, has for peptide fragment very efficient
Separating capacity.
Embodiment 3
As shown in Figure 1, preparing the ultra-fine capillary column of overlength by following process:
1) capillary activates: being successively passed through 1M NaOH 2h, distilled water 10min, 1M HCl 2h, distilled water 10min.Most
After methanol rinses 30min afterwards, N2Drying overnight.
2) 10mg CTAC, 20 μ L water, 120 μ L methanol, 75 μ L BTSEY, 45 preparation of hybridization mesoporous material: are accurately weighed
μ L VTMS pours into the capillary of activation, 40 DEG C of isothermal reaction 12h after mixing.After the reaction was completed, ethyl alcohol rinses 1h.
3) it is grafted the polymer brush of C18 functional group: accurately weighing 3mg AIBN, 20mg HSC18, 750 μ L ethyl alcohol, mixing is equal
After even, the capillary of activation, 60 DEG C of isothermal reaction 12h are poured into.After the reaction was completed, ethyl alcohol rinses 1h.
The ultra-fine internal diameter capillary tube column of the overlength of preparation obtains the effect of column similar in embodiment 1, has for peptide fragment very efficient
Separating capacity.
Embodiment 4
As shown in Figure 1, preparing the ultra-fine capillary column of overlength by following process:
1) capillary activates: being successively passed through 1M NaOH 2h, distilled water 10min, 1M HCl 2h, distilled water 10min.Most
After methanol rinses 30min afterwards, N2Drying overnight.
2) 5mg CTAC, 20 μ L water, 120 μ L methanol, 60 μ L BTSEY, 60 μ the preparation of hybridization mesoporous material: are accurately weighed
L VTMS pours into the capillary of activation, 40 DEG C of isothermal reaction 12h after mixing.After the reaction was completed, ethyl alcohol rinses 1h.
3) it is grafted the polymer brush of C18 functional group: accurately weighing 3mg AIBN, 20mg HSC18, 750 μ L ethyl alcohol, mixing is equal
After even, the capillary of activation, 60 DEG C of isothermal reaction 12h are poured into.After the reaction was completed, ethyl alcohol rinses 1h.
The ultra-fine internal diameter capillary tube column of the overlength of preparation obtains the effect of column similar in embodiment 1, has for peptide fragment very efficient
Separating capacity.
Embodiment 5
As shown in Figure 1, preparing the ultra-fine capillary column of overlength by following process:
1) capillary activates: being successively passed through 1M NaOH 2h, distilled water 10min, 1M HCl 2h, distilled water 10min.Most
After methanol rinses 30min afterwards, N2Drying overnight.
2) 5mg CTAC, 20 μ L water, 120 μ L methanol, 75 μ L BTSEY, 45 μ the preparation of hybridization mesoporous material: are accurately weighed
L VTMS pours into the capillary of activation, 40 DEG C of isothermal reaction 12h after mixing.After the reaction was completed, ethyl alcohol rinses 1h.
3) it is grafted the polymer brush of C18 functional group: accurately weighing 3mg AIBN, 15mg HSC18, 750 μ L ethyl alcohol, mixing is equal
After even, the capillary of activation, 60 DEG C of isothermal reaction 12h are poured into.After the reaction was completed, ethyl alcohol rinses 1h.
The ultra-fine internal diameter capillary tube column of the overlength of preparation obtains the effect of column similar in embodiment 1, has for peptide fragment very efficient
Separating capacity.
Claims (9)
1. a kind of preparation method of the organic-inorganic hybrid mesoporous material coating as chromatographic stationary phases, it is characterised in that:
(1) capillary tube inner wall is activated using bronsted lowry acids and bases bronsted lowry;
(2) sol-gel solution, hybrid coating of the preparation containing abundant double bond are prepared;
(3) method for using click chemistry, is bonded different stationary phases, obtains with different hydrophobic hybrid inorganic-organics
Chromatographic column.
2. preparation method described in accordance with the claim 1, it is characterised in that:
In step (1) the capillary tube inner wall activation method soda acid activation, it is characterised in that: quartz ampoule be successively passed through lye,
Distilled water, acid solution, distilled water, methanol, are then dried.
3. preparation method according to claim 2, it is characterised in that:
In the step (1), lye include sodium hydrate aqueous solution, potassium hydroxide, barium hydroxide, sodium carbonate, in potassium carbonate
It is one or more kinds of;Acid solution includes one or more of sulfuric acid, hydrochloric acid, nitric acid, acetic acid;
The range of the lye pH is more than or equal to 12;
The range of the acid solution pH is less than or equal to 2.
4. preparation method described in accordance with the claim 1, it is characterised in that:
In the step (2), sol gel reaction solution is formulated as follows, including template, organic solvent, water, catalyst and
Silylating reagent composition with double bond;
The template includes ionic surfactant such as cetyltrimethylammonium bromide (CTAB), cetyl chloride ammonium
(CTAC), nonionic surface active agent such as P123, F127, F108, polyethylene glycol (PEG);
The organic solvent include one of ethyl acetate, acetone, dimethylformamide, ethyl alcohol, methanol, water and two kinds with
On;
The catalyst includes formic acid, acetic acid, trifluoroacetic acid, propionic acid or ethamine, ethylenediamine, triethylamine.
5. the preparation method of the organic-inorganic hybrid mesoporous material coating as chromatographic stationary phases according to claim 4,
It is characterized by:
In the step (2), the content of the silylating reagent in sol gel reaction solution with double bond is 5~40% (v/
V), the molar content of catalyst is monomer 1/100~1/10;The ratio of organic solvent and water is 1~50 (v/v);
The silylating reagent with double bond includes the silylating reagent of terminal olefin base, comprising: vinyl trimethoxy silicon
Alkane, allyltriethoxysilane, allyltrimethoxysilanis, 3- (trimethoxy first silicon substrate) propyl acrylate, 1- (front three
Base siloxy) cyclohexene, bis- (triethoxy silicon substrate) one or more of ethylene and bridged silane reagent.
6. preparation method described in accordance with the claim 1, it is characterised in that:
30-70 DEG C of reaction temperature in capillary of step (2) sol gel reaction solution, reaction time 5-24h;Reaction
After the completion, ethyl alcohol rinses 0.2~5h.
7. preparation method described in accordance with the claim 1, it is characterised in that:
The solution of click-reaction described in step (3) includes initiator, organic solvent, mercapto monomers etc.;
The initiator is AIBN;
Organic solvent includes one of ethyl acetate, acetone, dimethylformamide, ethyl alcohol, methanol and two or more;
The mercapto monomers include one of glutathione, mercaptoethanol, butanethiol, spicy thioalcohol, Stearyl mercaptan and
It is two or more.
8. preparation method according to claim 6, it is characterised in that: mercapto monomers content in the solution of click chemistry reaction
For 1/1000~1/100 (w/w);The molar ratio of initiator and monomer is 1%-10%;After the reaction was completed, ethyl alcohol rushes click chemistry
Wash 0.2~5h.
9. having different hydrophobic organic-inorganic hybrid mesoporous material chromatographic columns that can be used for albumen described in a kind of claim 8
The separation analysis of biomolecule in matter group.
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CN117225385A (en) * | 2023-11-13 | 2023-12-15 | 天津赛飞乐生物技术有限公司 | Preparation method and application of surface modified porous oxide chromatographic material |
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