CN114989688A - Cyclodextrin porous polymer material solid phase micro-extraction probe and preparation method and application thereof - Google Patents
Cyclodextrin porous polymer material solid phase micro-extraction probe and preparation method and application thereof Download PDFInfo
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C09D133/20—Homopolymers or copolymers of acrylonitrile
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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- C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
- C09D105/16—Cyclodextrin; Derivatives thereof
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Abstract
The invention relates to the technical field of solid-phase microextraction, and particularly discloses a cyclodextrin porous polymer material solid-phase microextraction probe as well as a preparation method and application thereof. The cyclodextrin porous polymer material solid phase microextraction probe comprises a steel wire and a surface coating on the steel wire, wherein the surface coating is a cyclodextrin porous polymer material; the cyclodextrin porous polymer material comprises heptaamino-beta cyclodextrin and terephthalaldehyde. According to the invention, the cyclodextrin porous polymer material is used as the adsorbent of the solid phase microextraction probe surface coating, the material combines the advantages of the polymer material such as porosity and high specific surface area and the effective inclusion effect of cyclodextrin on purine, the purine extraction performance is still kept with high sensitivity and high enrichment performance under a high-polarity aqueous phase matrix, and the cyclodextrin porous polymer material can be applied to the detection and enrichment of purine in an aqueous phase biological sample.
Description
Technical Field
The invention relates to the technical field of solid-phase microextraction, in particular to a cyclodextrin porous polymer material solid-phase microextraction probe and a preparation method and application thereof.
Background
Solid-phase microextraction (SPME) is a novel sample pretreatment technology invented by janussz Pawliszyn, the university of luo, canada, in the early nineties of the last nineties, and was known as one of the most great inventions in the nineties. Compared with the traditional solid phase extraction technology, the SPME has the advantages of simple and convenient operation, easy realization of on-site sampling analysis and the like. In addition, the advantages of high efficiency, low detection limit and the like also make the method one of the most widely applied techniques in the sample pretreatment technology adopted at present.
The principle of solid phase microextraction is based on the distribution ratio of analyte between extraction coating and sample solution, so that the analyte can enter the extraction coating to achieve the purpose of enrichment and separation. Thus, extraction coating is a key factor in determining the extraction efficiency of SPME technology. Since most of biological samples are aqueous phases, and most of biological metabolites are polar or high-polar substances, how to advance polarity analytes from the high-polarity aqueous phases is also a challenge of the solid-phase microextraction technology. Most of SPME probes produced commercially at present are suitable for enriching nonpolar or weakly polar analytes, and have great vacancy in the development of SPME probes suitable for enriching polar analytes.
Therefore, it is necessary to provide an SPME probe material with good biocompatibility and high adsorption efficiency to polar analytes.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a cyclodextrin porous polymer material solid-phase microextraction probe and a preparation method and application thereof. According to the invention, a cyclodextrin porous polymer material is used as an adsorbent of a solid phase microextraction probe surface coating, and the adsorption efficiency of the material on purine is improved by utilizing the porosity of a covalent framework structure and the inclusion effect of cyclodextrin and purine. The probe can be applied to the analysis and detection of purine in a complex sample.
In order to achieve the purpose, the invention adopts the technical scheme that:
in a first aspect, the invention provides a cyclodextrin porous polymer material solid phase microextraction probe, which comprises a steel wire and a surface coating on the steel wire, wherein the surface coating is made of a cyclodextrin porous polymer material; the cyclodextrin porous polymer material comprises heptaamino-beta cyclodextrin and terephthalaldehyde in a mass ratio of (5-5.2): 1.0.
The core of the solid-phase microextraction technology lies in the extraction coating on the extraction probe, and the cyclodextrin porous polymer material is used as the adsorbent of the solid-phase microextraction probe surface coating, and the cyclodextrin porous polymer material is combined with the advantages of the polymer material such as porosity and high specific surface area and the effective inclusion effect of cyclodextrin on purine, so that the high sensitivity and high enrichment performance are still maintained on the extraction performance of purine under a high-polarity aqueous phase matrix, and the cyclodextrin porous polymer material can be applied to the detection and enrichment of purine in an aqueous phase biological sample. However, when the common cyclodextrin contacts water, hydrate is formed, and the cyclodextrin is difficult to be directly used as an adsorbent to extract a water sample.
As a preferred embodiment of the solid-phase microextraction probe of the cyclodextrin porous polymer material, the cyclodextrin porous polymer material is synthesized at normal temperature, and the preparation method specifically comprises the following steps:
ethanol and water are used as solvents, heptaamino-beta-cyclodextrin and terephthalaldehyde are used as reaction monomers, strong ammonia water is added as a catalyst to synthesize a polymer material, the polymer material and methanol are mixed and vibrated, and a product is centrifugally collected to obtain a cyclodextrin porous polymer material; wherein the mass ratio of the terephthalaldehyde to the strong ammonia water is 1.0 (22-23).
The average pore diameter of the cyclodextrin porous polymer material is 2-2.5 nm, and the specific surface area is 300-350 m 2/g. Specifically, the specific surface area is 318.9m2/g, the pore diameter is 2.18nm, and the high specific surface area promotes the cyclodextrin porous polymer material to be fully contacted with a sample solution, so that the cyclodextrin porous polymer material has a certain promotion effect on the extraction of analytes.
Preferably, the volume ratio of the ethanol to the water in the preparation process of the cyclodextrin porous polymer material is 1: 1.
In the preparation process of the cyclodextrin porous polymer material, the reaction temperature is room temperature, and the reaction time is 48 hours.
As a preferred embodiment of the solid-phase microextraction probe of the cyclodextrin porous polymer material, in the preparation method of the cyclodextrin porous polymer material, the concentration of the heptaamino-beta-cyclodextrin at the beginning of the reaction is (2.23-2.33) g/L; the concentration of the catalyst concentrated ammonia water added at the beginning of the reaction is 147 mmol/L. Preferably, the mass fraction of concentrated ammonia is 25% wt.
As a preferred embodiment of the cyclodextrin porous polymer material solid-phase microextraction probe, the surface coating has the thickness of 5-50 μm and the length of 1-2 cm.
The invention provides a preparation method of the cyclodextrin porous polymer material solid-phase microextraction probe, which comprises the following steps:
s1, synthesizing a polymer material by using ethanol and water as solvents, heptaamino-beta-cyclodextrin and terephthalaldehyde as reaction monomers and adding concentrated ammonia water as a catalyst;
s2, mixing and oscillating the polymer material and methanol, centrifuging and collecting a product to obtain a cyclodextrin porous polymer material;
s3, mixing the cyclodextrin porous polymer material with the polymer solution to obtain a mixed solution, extending the steel wire into the mixed solution, dipping, lifting and drying to obtain the cyclodextrin porous polymer material solid-phase microextraction probe.
Preferably, the diameter of the steel wire is 480 mu m, the length of the steel wire is 3-4 cm, and the dipping and pulling times are 1-4 times.
As a preferred embodiment of the preparation method of the present invention, the mass ratio of the heptaamino-beta-cyclodextrin, terephthalaldehyde and strong ammonia water is (5-5.2):1.0: (22-23).
As a preferred embodiment of the preparation method of the present invention, in the step S2, the mass ratio of the polymer material to the methanol is 1 (50-100), preferably 1: 100.
As a preferred embodiment of the preparation method, the polymer solution is a polyacrylonitrile/N, N-dimethylformamide solution, the mass ratio of polyacrylonitrile in the polyacrylonitrile/N, N-dimethylformamide solution is 5-12%, and preferably the mass ratio of polyacrylonitrile in the polyacrylonitrile/N, N-dimethylformamide solution is 10%.
The concentration of the polymer solution affects the uniformity of dispersion of subsequent materials in the solution and can affect the morphology of the probe. When the polymer solution is too thin and a lifting experiment is carried out, the thickness of a coating layer loaded on a steel wire is too thin, beads are easy to hang, and the appearance of the coating layer is uneven; the concentration of the solution is too high, the thickness of the coating which is pulled once is too thick, and the material is difficult to disperse in the polymer solution, so that the material agglomeration is easily caused, and the reproducibility and the performance of the probe are influenced. Therefore, based on a large number of research experiments, when the mass ratio of polyacrylonitrile to polyacrylonitrile in the N, N-dimethylformamide solution is 5-12%, the cyclodextrin porous polymer material is mixed with the polymer solution, so that the load material can be maximized as much as possible, the material performance can be maximized, and the mass ratio of the cyclodextrin porous polymer material to the polymer solution can be controlled to be 1 (5-50). When the mass ratio of polyacrylonitrile in the polyacrylonitrile/N, N-dimethylformamide solution is 10%, the performance of the obtained cyclodextrin porous polymer material solid-phase microextraction probe is optimal.
As a preferred embodiment of the preparation method, the mass ratio of the cyclodextrin porous polymer material to the polymer solution is 1 (5-50), and more preferably, the mass ratio of the cyclodextrin porous polymer material to the polymer solution is 1: 10.
In the preparation process of the cyclodextrin porous polymer material solid-phase microextraction probe, the reaction temperature is room temperature, and the reaction time is 48 hours.
The cyclodextrin porous polymer material solid phase microextraction probe of the invention needs to be purified in methanol for 5-10min before each use.
The invention also provides an application of the cyclodextrin porous polymer material solid-phase microextraction probe in enrichment detection of purine in biological samples.
Compared with the prior art, the invention has the following beneficial effects:
the preparation of the cyclodextrin porous polymer material is simple and convenient to operate, and the obtained NCP introduces cyclodextrin monomers under the advantages of retaining the high specific surface area, porosity and the like of the NCP material, so that the effective inclusion effect of cyclodextrin and purine enhances the purine adsorption performance of the material, thereby improving the purine adsorption efficiency. The cyclodextrin porous polymer material solid-phase microextraction probe provided by the invention has the advantages of excellent purine extraction performance, strong enrichment performance, low sensitivity and the like. The cyclodextrin porous polymer material solid-phase microextraction probe provided by the invention can be used for effectively detecting purine in a biological sample.
Drawings
FIG. 1 is a graph of isothermal adsorption and desorption curves of the cyclodextrin porous polymer material of example 1;
FIG. 2 is a microscopic morphology chart I of the cyclodextrin porous polymer material solid-phase microextraction probe characterized by a scanning electron microscope in example 1;
FIG. 3 is a microscopic morphology chart II of the cyclodextrin porous polymer material solid-phase microextraction probe characterized by a scanning electron microscope in example 1;
FIG. 4 is a MALDI-resistant plot of the cyclodextrin porous polymer material solid phase microextraction probe of example 1;
FIG. 5 is a graph comparing the solid phase microextraction probes of the cyclodextrin porous polymer material and commercial probes (PDMS, PA, PDMS/DVB) in example 1 with the extraction performance of 6 purines.
Detailed Description
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to the accompanying drawings and specific embodiments.
In the following examples, the experimental methods used were all conventional methods unless otherwise specified, and the materials, reagents and the like used were commercially available unless otherwise specified.
Example 1A solid-phase microextraction probe made of a cyclodextrin porous polymer material and a preparation method thereof
The preparation method of the cyclodextrin porous polymer material solid phase microextraction probe comprises the following steps:
1) preparation of cyclodextrin porous polymer material:
68.6mg of heptamino-beta-cyclodextrin and 13.4mg of terephthalaldehyde are weighed into a 50mL beaker, 30mL of ethanol-water mixed solvent (1: 1, v: v) is added into the beaker, ultrasonic treatment is carried out for 30min to uniformly disperse the system, 300 mu L of concentrated ammonia water (25% wt) is added as a catalyst, after reaction for 48h, the mixture is centrifuged, then ethanol and water are used for washing for three times in sequence, the obtained NCP material is dispersed into 50mL of methanol, and the NCP material is shaken for 48h to remove unreacted substances in holes. The material was then dried in a vacuum oven. Is denoted as beta-CD-NCP.
2) Preparing a cyclodextrin porous polymer material solid phase microextraction probe:
(1) cutting stainless steel fiber into 4cm length, sequentially soaking in ultrapure water and methanol, performing ultrasonic treatment at room temperature for 15min, taking out, and naturally drying.
(2) Mixing 15.6mg polyacrylonitrile and 140mg N, N-dimethylformamide uniformly, and performing ultrasonic treatment for 15min to obtain uniformly dissolved polyacrylonitrile/N, N-dimethylformamide solution.
(3) Weighing 15.6mg of prepared beta-CD-NCP material, adding the beta-CD-NCP material into the system (2), uniformly stirring, and performing ultrasonic treatment for 15min to uniformly disperse the beta-CD-NCP material.
(4) And (3) extending 1cm of the front end of the stainless steel fiber pretreated in the step (1) into the uniform system obtained in the step (3), and slowly lifting upwards to obtain the beta-CD-NCP/polyacrylonitrile mixed coating with a uniform surface.
(5) The fiber was placed in an oven at 80 ℃ to dry for 1 hour. Taking out, and repeating the operation until the thickness of the coating reaches the requirement. Soaking the fiber with the length of 1cm and the thickness of 5-50 mu m of the surface coating in methanol overnight to remove impurities contained in the coating, and taking out for later use to prepare the cyclodextrin porous polymer material solid-phase microextraction probe.
Referring to FIG. 1, an adsorption-desorption curve chart of the beta-CD-NCP material shows that the prepared beta-CD-NCP material has an average pore diameter of 2-2.5 nm and a specific surface area of 300-350 m 2 (ii) in terms of/g. Specifically, the specific surface area was 318.9m 2 (ii)/g, pore diameter 2.18 nm. The high specific surface area promotes the material to be fully contacted with the sample solution, and has certain promotion effect on the extraction of the analyte.
The cavity of the cyclodextrin is 0.8nm, the average pore diameter of the NCP material is about 2.18nm, and the size of six purine molecules selected in the work is less than 0.9nm, so that purine can enter the pores of the prepared NCP material to achieve the adsorption effect. The material prepared by combining the advantages of inclusion effect of cyclodextrin on purine and the like can efficiently adsorb the target analyte purine.
From the fig. 2 and 3, the micro-topography of the prepared beta-CD-NCP solid phase micro-extraction probe characterized by a scanning electron microscope can be observed.
Example 2 anti-deposition Effect of Cyclodextrin porous Polymer Material solid phase micro-extraction probes on proteins
The anti-deposition effect of the cyclodextrin porous polymer material solid-phase microextraction probe prepared in the embodiment 1 of the invention on protein is explored.
The cyclodextrin porous polymer material solid-phase microextraction probe prepared in the embodiment 1 of the invention is extracted from a serum sample which is diluted ten times by PBS solution. And washing the extracted probe with flowing ultrapure water for 10s to remove an extraction phase on the probe, slightly wiping the probe with dust-free paper, and immersing the probe in 80 microliters of desorption solvent for desorption. The desorption solution obtained is analyzed by a matrix assisted laser desorption tandem time of flight mass spectrometer (MALDI-TOF MS), the added matrix is 10mg/mL DHB (30% acetonitrile, 0.1% trifluoroacetic acid), and mass spectrogram analysis of the matrix and the desorption solution when m/z is between 1000-10000 is compared, the result is shown in figure 4, no obvious peak appears when m/z is more than 1000 in the desorption solution, and the prepared probe has good anti-protein deposition effect.
Example 3 application of Cyclodextrin porous Polymer Material solid phase microextraction Probe in extraction analysis of purine
The solid phase microextraction probe of the cyclodextrin porous polymer material prepared in example 1 of the present invention, and the extraction capacities of the commercial PDMS extraction probe (Sulpelco), PA extraction probe (Sulpelco) and PDMS/DVB extraction probe (Sulpelco) for 6 purines were determined.
The solid-phase microextraction probe of the cyclodextrin porous polymer material prepared in the embodiment 1 of the invention, a commercial PDMS extraction probe, a PA extraction probe and a PDMS/DVB extraction probe are respectively extracted in a buffer solution with the concentration of 100ppb of 6 purines (Xanthine, Hypoxanthine, Xanthine, Guanosine, guananine and Adenine) for 30min, the extracted probe is washed for 10 seconds by flowing ultrapure water, the probe is placed in 80 microliter desorption liquid for desorption for 30min and then taken out, the desorption liquid enters an HPLC-MS/MS instrument for analysis, and the peak areas of all substances are compared, so that the adsorption capacities of different probes on different analytes are compared, and the result is shown in figure 5.
Experimental results show that the adsorption performance of the cyclodextrin porous polymer material solid-phase microextraction probe on the 6 measured purines is higher than that of a commercial extraction probe, and the cyclodextrin porous polymer material solid-phase microextraction probe has good extraction performance on the purines.
In conclusion, the prepared cyclodextrin porous polymer material (beta-CD-NCP) is used as the adsorbent of the solid phase microextraction probe surface coating, and the material is combined with the porosity of the polymer compound material and the effective inclusion effect of cyclodextrin and purine, can effectively capture purine molecules in a high-polarity water phase sample, improves the purine adsorption efficiency of the material, and can be applied to the detection and enrichment of purine in a complex biological sample.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. A cyclodextrin porous polymer material solid phase micro-extraction probe is characterized by comprising a steel wire and a surface coating on the steel wire, wherein the surface coating is a cyclodextrin porous polymer material; the cyclodextrin porous polymer material comprises heptaamino-beta cyclodextrin and terephthalaldehyde.
2. The cyclodextrin porous polymer material solid phase microextraction probe of claim 1, wherein the cyclodextrin porous polymer material is synthesized at room temperature, and the specific preparation method comprises the following steps:
ethanol and water are used as solvents, heptamino-beta-cyclodextrin and terephthalaldehyde are used as reaction monomers, strong ammonia water is added as a catalyst to synthesize a polymer material, the polymer material and methanol are mixed and vibrated, and a product is centrifugally collected to obtain a cyclodextrin porous polymer material; wherein the mass ratio of the terephthalaldehyde to the strong ammonia water is 1.0 (22-23).
3. The cyclodextrin porous polymer material solid-phase microextraction probe of claim 2, wherein in the preparation method of the cyclodextrin porous polymer material, the concentration of heptamino-beta-cyclodextrin at the beginning of the reaction is (2.23-2.33) g/L; the concentration of the catalyst concentrated ammonia water added at the beginning of the reaction is 147 mmol/L.
4. The cyclodextrin porous polymer material solid phase microextraction probe of claim 1, wherein the surface coating has a thickness of 5-50 μ ι η and a length of 1-2 cm.
5. The method for preparing a cyclodextrin porous polymer material solid phase microextraction probe according to any one of claims 1-4, comprising the steps of:
s1, synthesizing a polymer material by using ethanol and water as solvents, heptaamino-beta-cyclodextrin and terephthalaldehyde as reaction monomers and adding concentrated ammonia water as a catalyst;
s2, mixing and oscillating the polymer material and methanol, centrifuging and collecting a product to obtain a cyclodextrin porous polymer material;
s3, mixing the cyclodextrin porous polymer material with the polymer solution to obtain a mixed solution, extending the steel wire into the mixed solution, dipping, lifting and drying to obtain the cyclodextrin porous polymer material solid-phase microextraction probe.
6. The method according to claim 5, wherein the mass ratio of the heptaamino-beta-cyclodextrin, the terephthalaldehyde and the concentrated ammonia water is (5-5.2):1.0: (22-23).
7. The method of claim 5, wherein in the step S2, the mass ratio of the polymer material to the methanol is 1 (50-100).
8. The preparation method according to claim 5, wherein the polymer solution is a polyacrylonitrile/N, N-dimethylformamide solution, and the mass ratio of polyacrylonitrile in the polyacrylonitrile/N, N-dimethylformamide solution is 5-12%, preferably 10%.
9. The preparation method according to claim 5, wherein the mass ratio of the cyclodextrin porous polymer material to the polymer solution is 1 (5-50), and more preferably, the mass ratio of the cyclodextrin porous polymer material to the polymer solution is 1: 10.
10. Use of the cyclodextrin porous polymer material solid phase microextraction probe of any one of claims 1-4 for the enrichment detection of purines in a biological sample.
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| CN116586047A (en) * | 2023-07-07 | 2023-08-15 | 生态环境部华南环境科学研究所(生态环境部生态环境应急研究所) | Polymer coated fiber, preparation method and application thereof in detection of trace polycyclic aromatic hydrocarbon |
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| CN114522445A (en) * | 2022-01-04 | 2022-05-24 | 广东省科学院测试分析研究所(中国广州分析测试中心) | Preparation method and application of core-shell structure composite material solid phase micro-extraction probe |
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| CN113209952A (en) * | 2021-05-08 | 2021-08-06 | 中国药科大学 | Chiral covalent organic framework membrane and preparation method and application thereof |
| CN114522445A (en) * | 2022-01-04 | 2022-05-24 | 广东省科学院测试分析研究所(中国广州分析测试中心) | Preparation method and application of core-shell structure composite material solid phase micro-extraction probe |
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| CN116586047B (en) * | 2023-07-07 | 2023-10-13 | 生态环境部华南环境科学研究所(生态环境部生态环境应急研究所) | Polymer coated fiber, preparation method and application thereof in detection of trace polycyclic aromatic hydrocarbon |
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