CN106009012B - Nano-titanium dioxide loads Serine imprinted polymer lamellae and its preparation method - Google Patents

Nano-titanium dioxide loads Serine imprinted polymer lamellae and its preparation method Download PDF

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CN106009012B
CN106009012B CN201610396244.5A CN201610396244A CN106009012B CN 106009012 B CN106009012 B CN 106009012B CN 201610396244 A CN201610396244 A CN 201610396244A CN 106009012 B CN106009012 B CN 106009012B
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titanium dioxide
serine
lamellae
imprinted polymer
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李辉
张月
王素素
龚美叶
龚梦婷
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Hubei Chuang Chuang Biological Technology Co ltd
Shenzhen Pengbo Information Technology Co ltd
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Jishou University
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Abstract

For the present invention using nano-titanium dioxide as carrier, L serines are template, and L Serine molecule imprinted polymers are prepared for using surface imprinted method.Titanium dioxide surface is activated by using salpeter solution, then the titanium dioxide activated with γ MAPS modifications, increases surface of solids functional group, improve the ability of carrier surface grafting L serine imprinted polymers.The lamellae that gained molecularly imprinted polymer is prepared into, with the n-butanol glacial acetic acid water of 0.1% ninhydrin (V/V, 4:1:1) it is solvent, when being detached for chiral compound L and D serines, relative Rf value is more than 2.0, the two efficiently separates, it solves the problems, such as that conventional lamellae stationary phase and conventional liquid phase chromatographic stationary phases can not detach, realizes the molecular engram thin layer separation of chiral amino acid compound.The present invention provides a kind of new material and method for the chiral resolution of serine and separation analysis.

Description

Nano-titanium dioxide loads Serine imprinted polymer lamellae and its preparation method
Technical field
The present invention relates to a kind of nano-titanium dioxide area load Serine imprinted polymer lamellae and its preparation sides Method.
Background technology
Molecularly imprinted polymer（MIP）Be by molecular imprinting technology synthesize to specific target molecules (template molecule) and Its analogue has the polymer of specific recognition and selective absorption.MIP preparation principles：By microsphere（Template point Son）It mixes with suitable function monomer, and is polymerized using crosslinking agent, the formation degree of cross linking is very high around microsphere three Crosslinked high molecular polymer network is tieed up, is then again removed the molecule of trace with method appropriate, finally obtained polymer As molecularly imprinted polymer.MIP has the properties such as identity, structure effect precordainment, practicability, therefore it extracts in chromatography solid phase It takes, clinical medicine analysis, many fields such as chemobionics sensor are with a wide range of applications.Currently, synthetic molecules print The method of mark polymer is mainly mass polymerization, microemulsion polymerization method, situ aggregation method and surface grafting polymerization method etc..
Serine also known as beta-hydroxy alanine, there are two kinds of isomers of levo form and raceme, including L- ammonia for serine Acid and D-Ser.It contributes to the generation of immunoglobulin and antibody, maintains the immune system of health.In addition, serine exists It all plays an important role in the synthesis of the sheath for manufacturing processing, musculature and encirclement nerve cell of cell membrane.Serine It is that and can derive after the phosphorylated effect of Serine hydroxyl and provide in addition to being the precursor of purine biosynthesis, thymidine, choline The Phosphoserine of important physiological function is one of main component of phosphatide.The researcher of Britain's Beatson Cancer Institutes sends out Existing serine can significantly weaken growth and the proliferative capacity of cancer cell.Conventional liquid phase chromatographic stationary phases and thin-layer chromatography can not be real The fractionation of existing serine chipal compounds.
Nano-titanium dioxide is a kind of multi-crystalline compounds, mainly there is three kinds of Detitanium-ore-type, rutile-type, brookite type crystalline substances Type.Titanium dioxide has many Optimalities such as fusing point is low, absorbing properties are good, surface-active is big, grain size is small, large specific surface area Matter, after nano-titanium dioxide is surface-treated and is chemically modified, can effective grafting molecules imprinted polymer, improve molecule The molecular recognition dynamics and molecular recognition efficiency of imprinted polymer and target compound.
Invention content
In order to overcome the deficiencies of the prior art, we synthesize Serine imprinted polymer using surface grafting polymerization method, will Nano TiO 2 and template molecule after pretreatment（Serine）It is dissolved in suitable acetonitrile-DMSO（4:1,v/v）In mixed solution, Initiator A IBN, function monomer (4-vinylpridine) and crosslinking agent EGDMA is added, ultrasonic degassing is carried out after being sufficiently mixed, is led to Enter nitrogen to seal rapidly after removing the oxygen in solution, is reacted under the conditions of 333K waters bath with thermostatic control and obtain trace polymerization afterwards for 24 hours Object.It is dried in vacuo with elution after crushing, grinding, screening, it is spare.The molecularly imprinted polymer that this method obtains is to print Mark molecule has relatively good evident characteristics and selectivity, chiral L- and D-Ser to have compared with high separating efficiency.
Serine imprinted polymer lamellae is loaded to obtain nano-titanium dioxide, the present invention takes following technique to walk Suddenly：
（1）The pretreatment of nano-titanium dioxide：Accurately weigh 6.0g nano-TiOs2It is placed at a temperature of 353K and toasts 12h, it is cold But, volume V is measured1The concentrated nitric acid solution of=20mL, move to be configured in the volumetric flask of 100mL concentration 3.2mol/L nitric acid it is molten Liquid, then by nano-TiO2It is immersed in the salpeter solution of 3.2mol/L after 12h, it is de- that precipitation is washed with deionized water after vacuum filtration To pH 7.0, at a temperature of 333K, it is dried in vacuo 6h, it is spare；
（2）The surface modification of nano-titanium dioxide：Weigh the activated nano-TiOs of 2.0g2, 4 mL γ-MAPS- first are added Mixed alkoxide solution [V/V, 1:1], 12h is reacted at a temperature of 313K, it is cooling, it grinds, and use 50mL methanol and water washing de- successively Solid, it is dry, it is spare；
（3）The preparation of nano-titanium dioxide surface grafting imprinted polymer：It is accurate weigh that 400mg surface modifications cross receive Rice TiO2, 10mL acetonitriles-DMSO (4 is added:1) in mixed solution, 0.2mmol Serines are added in stirring, are added 0.8mmol function monomers 4-VP（4-vinylpridine）With the initiator of 4.00 mmol crosslinking agents EGDMA and 60.00 mg AIBN after being sufficiently mixed, is transferred in EP pipes, and ultrasound 15 min of degassing are passed through 15 min of nitrogen, seal, EP pipes are put into 60 DEG C 24 h of polymerisation in thermostat water bath crushes the bulk polymer of gained, and 200-400 purpose polymers are collected in sieving Grain, uses methanol-acetic acid（9/1, v/v）Solution elutes 8 times, and again with methanol elutes 4 times, and after filtering, solid is put into vacuum drying Case dries 24 h to get molecularly imprinted polymer in 60 DEG C；
（4）The preparation of molecularly imprinted polymer lamellae：Weigh the sanlose of 5.0g（CMC-Na）It is dissolved in In 1000mL water, it is configured to 0.5% sanlose（CMC-Na）Aqueous solution falls suitable tlc silica gel Enter CMC-Na it is water-soluble after be stirred continuously, be modulated into thick silica gel homogenate.Weigh the addition of m=0.060g molecularly imprinted polymers It into above-mentioned silica gel homogenate, grinds well, rapidly coating on ready glass plate, the lamellae after coating is placed in 30 DEG C of baking ovens Middle drying.
The separation of molecular engram thin layer carries out according to the following procedure：(1) L- and each 16.0mg of D-Ser are weighed, is dissolved in respectively In 100.0mL deionized waters, it is configured to a concentration of 0.160 mg mL-1L- and D-Ser sample solution.(2) by lamellae The polymer at edge shaves, on the baseline apart from lamellae lower end 0.5cm, with two kinds of same time points of sample solution of capillary pair Sample puts about 1cm at a distance between point.(3) lamellae lower end is put into n-butanol-glacial acetic acid-water containing 0.1% ninhydrin （V/V, 4:1:1）In solvent, lamellae is taken out after 15 minutes, spontaneously dries 5 minutes, respective spot is observed under ultraviolet lamp Position, and the Rf value R both calculatedf。
Compared with prior art, the beneficial effects of the present invention are：
Nano-titanium dioxide surface is handled with salpeter solution, then with after γ-MAPS modifications, improves the table of solid particle Face imprinting effect, the molecular recognition performance of enhancing gained molecularly imprinted polymer；Using Serine as template, with nano-TiO2For Serine molecularly imprinted polymer lamellae prepared by carrier, with n-butanol-glacial acetic acid-water containing 0.1% ninhydrin（V/V, 4:1:1）For solvent when, Serine and D-Ser can be efficiently separated, the transplanting that compares is more than 2.0, solves conventional thin The problem that layer stationary phase and conventional liquid phase chromatographic stationary phases can not detach, the molecular engram for realizing chiral amino acid compound are thin Layer separation.The present invention provides a kind of new material and method for the chiral resolution of serine and separation analysis.The present invention obtains Lamellae can be additionally used in the extracting and developing of Serine and analysis in Cortex Eucommiae extracting solution, by Eucommia Samples solution and standard ammonia Base acid while point sample, are placed in ethyl acetate-glacial acetic acid-water containing 0.1% ninhydrin（V/V, 4:1:1）After being unfolded in solvent, By being observed under ultraviolet lamp, the polymer containing Serine is scraped, with 2.0mL methanol-acetic acids（9:1,v/v）Mixed solution soaks 4h is steeped, after supersound process, supernatant liquor is can use and carries out ultraviolet detection and analyze Serine content.
Specific implementation mode
Serine imprinted polymer lamellae is loaded to nano-titanium dioxide below and its preparation method is described in detail.
（1）The pretreatment of nano-titanium dioxide：Accurately weigh 6.0g nano-TiOs2It is placed at a temperature of 353K and toasts 12h, it is cold But, volume V is measured1The concentrated nitric acid solution of=20mL, move to be configured in the volumetric flask of 100mL concentration 3.2mol/L nitric acid it is molten Liquid, then by nano-TiO2It is immersed in the salpeter solution of 3.2mol/L after 12h, it is de- that precipitation is washed with deionized water after vacuum filtration To pH 7.0, at a temperature of 333K, it is dried in vacuo 6h, it is spare；
（2）The surface modification of nano-titanium dioxide：Weigh the activated nano-TiOs of 2.0g2, 4 mL γ-MAPS- first are added Mixed alkoxide solution [V/V, 1:1], 12h is reacted at a temperature of 313K, it is cooling, it grinds, and use 50mL methanol and water washing de- successively Solid, it is dry, it is spare；
（3）The preparation of nano-titanium dioxide surface grafting imprinted polymer：It is accurate weigh that 400mg surface modifications cross receive Rice TiO2, 10mL acetonitriles-DMSO (4 is added:1) in mixed solution, 0.2mmol Serines are added in stirring, are added 0.8mmol function monomers 4-Vp（4-vinylpridine）With the initiator of 4.00 mmol crosslinking agents EGDMA and 60.00 mg AIBN after being sufficiently mixed, is transferred in EP pipes, and ultrasound 15 min of degassing are passed through 15 min of nitrogen, seal, EP pipes are put into 60 DEG C 24 h of polymerisation in thermostat water bath crushes the bulk polymer of gained, and 200-400 molecules of interest traces are collected in sieving Polymer uses methanol-acetic acid（9/1, v/v）Solution elutes 8 times, and again with methanol elutes 4 times, and after filtering, solid is put into vacuum Drying box dries 24 h to get molecularly imprinted polymer in 60 DEG C；
（4）The preparation of molecularly imprinted polymer lamellae：Weigh the sanlose of 5.0g（CMC-Na）It is dissolved in In 1000mL water, it is configured to 0.5% sanlose（CMC-Na）Aqueous solution falls suitable tlc silica gel Enter CMC-Na it is water-soluble after be stirred continuously, be modulated into thick silica gel homogenate.Weigh the addition of m=0.060g molecularly imprinted polymers It into above-mentioned silica gel homogenate, grinds well, rapidly coating on ready glass plate, the lamellae after coating is placed in 30 DEG C of baking ovens Middle drying.
Lamellae obtained above is used to test the separation efficiency of L- and D-Ser and for Serine in Cortex Eucommiae Extracting and developing and analysis.By L- and D-Ser standard solution difference point sample on molecular engram lamellae, and by lamellae N-butanol-glacial acetic acid-water containing 0.1% ninhydrin is put into lower end（V/V, 4:1:1）In solvent, thin layer is taken out after 15 minutes Plate spontaneously dries 5 minutes, the position of respective spot is observed under ultraviolet lamp, and calculates the Rf value R of the twof.For Cortex Eucommiae sample The application of product, by Eucommia Samples solution and standard amino acid simultaneously point sample on lamellae, being placed in the acetic acid containing 0.1% ninhydrin Ethyl ester-glacial acetic acid-water（V/V, 4:1:1）It, will be poly- containing Serine by observing in the UV lamp after being unfolded in solvent It closes object to scrape, with 2.0mL methanol-acetic acids（9:1,v/v）Mixed solution impregnates 4h, after supersound process, takes supernatant liquor, carries out purple Outer detection and analysis measure Serine concentration.
Above-described embodiment is not intended to limit the present invention in any form, any technical person familiar with the field, In the case of not departing from technical solution of the present invention range, all technical solution of the present invention is done using the technology contents of the disclosure above Go out many possible changes and modifications, or is revised as the equivalent embodiment of equivalent variations.Therefore, every without departing from the technology of the present invention The content of scheme, technical spirit any simple modifications, equivalents, and modifications made to the above embodiment according to the present invention, It should fall in the range of technical solution of the present invention is protected.

Claims (3)

1. a kind of preparation method of nano-titanium dioxide area load Serine imprinted polymer lamellae, it is characterised in that packet Containing following steps：
（1）The activation of nano-titanium dioxide：Accurately weigh 6.0g nano-TiOs2It is placed at a temperature of 353K and toasts 12h, it is cooling, it measures Volume V1The concentrated nitric acid solution of=20mL moves to the salpeter solution that concentration 3.2mol/L is configured in the volumetric flask of 100mL, then will Nano-TiO2It is immersed in the salpeter solution of 3.2mol/L, is filtered by vacuum after 12h, solid is washed with deionized to pH 7.0, And solid is dried in vacuo 6h at a temperature of 333K, it is spare；
（2）The surface modification of nano-titanium dioxide：Weigh the activated nano-TiOs of 2.0g2, it is 1 that 4 mL volume ratios, which are added,:1 γ-MAPS- methanol mixed solutions, react 12h at a temperature of 313K, cooling, grind, and use 50mL methanol and water washing de- successively Solid, it is dry, it is spare；
（3）Nano-titanium dioxide surface grafting molecularly imprinted polymer：Accurately weigh the nano-TiO that 400mg surface modifications are crossed2, It is added to 10mL 4:In 1 acetonitrile-DMSO mixed solutions, 0.2mmol Serines are added in stirring, and 0.8mmol functions are added The initiator A IBN of monomer 4-VP, 4.00 mmol crosslinking agents EGDMA and 60.00 mg after being sufficiently mixed, are transferred in EP pipes, are surpassed Sound 15 min of degassing, are passed through 15 min of nitrogen, seal, EP pipes are put into 24 h of polymerisation in 60 DEG C of thermostat water baths, by institute It obtains bulk polymer to grind, be sieved, collect the solid particle between -400 mesh of 200 mesh, be 9 with volume ratio:1 methanol-acetic acid is molten Liquid elutes 8 times, and again with methanol elutes 4 times, and filtered solid is put into vacuum drying chamber in 60 DEG C of dry 24 h to get molecule Imprinted polymer；
（4）The preparation of molecularly imprinted polymer lamellae：The sanlose for weighing 5.0g is dissolved in 1000mL water, is matched 0.5% sanlose aqueous solution is made, suitable tlc silica gel is poured into sanlose water It is stirred continuously after solution, is modulated into thick silica gel homogenate, weighed m=0.060g molecularly imprinted polymers and be added to above-mentioned silicon It in glue homogenate, grinds well, rapidly coating on ready glass plate, the lamellae after coating is placed in 30 DEG C of baking ovens dry.
2. the nano-titanium dioxide area load Serine imprinted polymer thin layer that method obtains according to claim 1 Plate.
3. a kind of method carrying out chiral resolution and separation analysis to serine, it is characterised in that：By L- and D-Ser standard Substance solution nano-titanium dioxide described in claim 2 loads on Serine imprinted polymer lamellae while point sample, sets In the volume ratio containing 0.1% ninhydrin be 4:1:After being unfolded in the solvent of 1 ethyl acetate-glacial acetic acid-water, in the UV lamp Spot is observed, the transplanting that compares of two kinds of compounds is more than 2.0, realizes chiral resolution and the separation of L- and D-Ser compound Analysis, the polymer after separation at respective spot is scraped off, and is 9 with 2.0mL volume ratios:1 methanol-acetic acid mixed solution 4h is impregnated, after supersound process, supernatant liquor is taken, carries out ultraviolet detection analysis, the rate of recovery of two kinds of chipal compounds can be measured.
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CN109991291A (en) * 2019-04-04 2019-07-09 蚌埠学院 A kind of preparation method of Serine molecular engram sensor
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CN102993389A (en) * 2012-11-30 2013-03-27 中南大学 Optical intelligent silicagel surface molecularly imprinted microsphere and preparation method thereof
CN103949228A (en) * 2014-05-09 2014-07-30 河北大学 Preparation method of molecularly-imprinted magnetic silica microsphere with hydrophilic external surface
CN105348440A (en) * 2015-10-27 2016-02-24 上海中医药大学 Oblongifolin C molecularly imprinted polymer, and preparation method and application thereof

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* Cited by examiner, † Cited by third party
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CN102993389A (en) * 2012-11-30 2013-03-27 中南大学 Optical intelligent silicagel surface molecularly imprinted microsphere and preparation method thereof
CN103949228A (en) * 2014-05-09 2014-07-30 河北大学 Preparation method of molecularly-imprinted magnetic silica microsphere with hydrophilic external surface
CN105348440A (en) * 2015-10-27 2016-02-24 上海中医药大学 Oblongifolin C molecularly imprinted polymer, and preparation method and application thereof

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