CN115078612A - Analysis method for detecting chemicals based on modified Cr-MOF - Google Patents

Analysis method for detecting chemicals based on modified Cr-MOF Download PDF

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CN115078612A
CN115078612A CN202210613692.1A CN202210613692A CN115078612A CN 115078612 A CN115078612 A CN 115078612A CN 202210613692 A CN202210613692 A CN 202210613692A CN 115078612 A CN115078612 A CN 115078612A
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丁利
张泽霖
王领娟
陈卓
马琳琳
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Changsha University of Science and Technology
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Abstract

The invention relates to an analysis method for detecting chemicals based on modified Cr-MOF, which utilizes a dispersed solid phase extraction technology, adopts modified Cr-MOF solid phase extraction to exclude proteins in biological samples and enrich risperidone, quetiapine, aripiprazole and metabolites thereof, namely 9-hydroxy risperidone, N-dealkylated quetiapine and dehydroaripiprazole, and carries out high performance liquid chromatography detection. According to the method, ethylenediamine is grafted on the basis of MIL-101(Cr) to form modified Cr-MOF, so that the enrichment efficiency of risperidone, quetiapine, aripiprazole and metabolites thereof is improved, and proteins in a biological sample system are excluded, so that the step of protein precipitation is omitted. The method has the advantages of simple operation, pretreatment time and cost saving, good extraction effect, cheap and easily-obtained raw materials, environment-friendly application and wide market prospect, and the material used by the method is expected to become a special material for extracting the biological sample.

Description

Analysis method for detecting chemicals based on modified Cr-MOF
Technical Field
The invention belongs to the field of chemical detection, and relates to an analysis method for detecting chemicals based on modified Cr-MOF.
Background
According to the current data of the world health organization, psychiatric disorders (i.e., schizophrenia or bipolar disorder, manifested by hallucinations, delusions, or paranoia) affect approximately 8300 million people worldwide. A range of antipsychotic drugs has emerged to provide effective treatment of the symptoms of various psychiatric disorders. Antipsychotic drugs may produce side effects on the human body in many ways, and the kinds of drugs, the doses consumed, or individual differences of patients vary, but most have common side effects. Therefore, blood concentration monitoring is particularly important in psychiatry. Can be used for effective clinical management of patients receiving psychotropic medication. Avoid medical complications and poisoning, and have no reaction or non-compliance. Therefore, it is necessary to enhance the detection of psychotropic drugs in blood concentration monitoring.
The blood concentration monitoring is to analyze the concentration of the drug to be measured in blood by taking the pharmacokinetic principle as a guide so as to evaluate the curative effect or determine the administration scheme, so that the administration scheme is individualized, the therapeutic level of the drug is improved, and the clinical safe, effective and reasonable administration is achieved. Since serum contains a large amount of protein and the concentration of psychotropic drugs in blood is generally low, and patients often use other drugs, which may interfere with the analysis, the pretreatment method must have high selectivity and high sensitivity to accurately determine the nature and quantity of the subsequent analysis. In the prior art, the conventional method for analyzing and detecting the psychotropic drugs is a pretreatment technology combined with a high performance liquid chromatography, and the pretreatment method for detecting the psychotropic drugs in serum mainly comprises liquid-liquid extraction (LLE), Protein Precipitation (PP) and Solid Phase Extraction (SPE). At present, the commonly adopted liquid-liquid extraction method has the problems of excessive use of organic reagents, low extraction rate and the like; the protein precipitation has the defects of low protein precipitation efficiency, easy blockage of high performance liquid chromatography, interference analysis of other medicines and the like; the solid phase extraction method has the disadvantages of long extraction time, complicated steps (protein removal and extraction are needed firstly), easy blockage of an extraction column, need of special equipment and the like.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, and designs an analysis method for detecting chemicals based on modified Cr-MOF, which utilizes a Dispersed Solid Phase Extraction (DSPE) technology and simultaneously adopts the modified Cr-MOF as a solid phase extraction material.
The Dispersive Solid Phase Extraction (DSPE) is a novel sample pretreatment technology developed based on nano materials. In recent years, many researchers introduce MOFs materials into a dispersion solid phase extraction method as an adsorbent, and the MOFs materials are porous coordination polymers which are self-assembled by metal ions and organic ligands through coordination bonds and have the characteristics of large specific surface area, changeable and adjustable structure, stable chemical properties and the like.
In order to achieve the above object, the present invention provides an analytical method for detecting chemicals based on modified Cr-MOF, comprising: the method comprises the steps of removing protein from a serum sample to be detected by a dispersive solid-phase extraction technology, enriching, and carrying out ultraviolet detection to obtain the concentration of a related medicament, and specifically comprises the following steps:
1) taking the modified Cr-MOF in a centrifugal tube, adding a buffer solution and serum into the centrifugal tube, swirling to uniformly disperse the modified Cr-MOF in a sample, centrifuging for 4-6min at 80000-10000r/min, and pouring out a supernatant; wherein the ratio of the buffer solution to the serum is 4: 1;
2) adding an elution solution into the precipitate obtained in the step 1), performing vortex, performing full elution, centrifuging for 5min at 8000r/min, pouring the supernatant into a new centrifugal tube, blowing nitrogen for drying, re-dissolving by using a re-solution, dispersing uniformly, and performing high performance liquid chromatography detection on the prepared reaction system.
The preparation method of the modified Cr-MOF in the step 1) comprises the following steps:
s1, dissolving chromium nitrate nonahydrate and terephthalic acid in ultrapure water, dropwise adding a hydrofluoric acid aqueous solution with the mass fraction of 40%, and fully stirring to dissolve the chromium nitrate nonahydrate, the terephthalic acid, the ultrapure water and the hydrofluoric acid aqueous solution in a mass ratio of (80-90) to (30-40) to 1 (10-20);
s2, reacting the mixture prepared in the step 1) in a solvent thermal reaction kettle at the temperature of 210 ℃ and 230 ℃ for 7-9h, and washing the prepared mixture with DMF and hot ethanol;
s3, soaking the sample obtained in the step 2) in absolute ethyl alcohol for 18-22h, washing and drying after the reaction is finished, then putting the sample into 30mmol/L ammonium fluoride solution for reaction for 9-11h at the temperature of 58-62 ℃, washing with warm deionized water, and carrying out vacuum drying at the temperature of 90-110 ℃ overnight to obtain purified Cr-MOF;
s4, dissolving the purified Cr-MOF in absolute ethyl alcohol, continuously adding ethylenediamine, transferring into a reaction kettle for reaction, washing with the ethyl alcohol for multiple times after the reaction is finished, and carrying out vacuum drying at 90-11 ℃ for 10-14h to obtain the modified Cr-MOF.
In the step 1), the buffer solution is an acidic aqueous solution.
The pH value of the buffer solution is 3-5.
The elution solution in the step 2) is methanol solution, methanol solution with 2% acetic acid by volume, acetonitrile or acetone.
The complex solution in the step 2) is acetonitrile water solution;
the volume ratio of acetonitrile to water in the acetonitrile water solution is 1: 4.
The detection conditions of the high performance liquid chromatography in the step 2) are as follows: the method adopts 50mm multiplied by 2.1mm of waters ACQUity UPLC C18 and 1.7um as a chromatographic column; the detector is a diode array ultraviolet detector, and the measuring wavelength is 250 nm; sample injection amount of the autosampler: 20 uL; the mobile phase A is: 975ml of ultrapure water +25ml of 2M ammonium acetate solution +1ml of formic acid +1ml of triethylamine, mobile phase B being acetonitrile.
The psychotropic drugs are risperidone, quetiapine, N-dealkylated quetiapine, dehydroaripiprazole, aripiprazole and 9-hydroxyrisperidone which is a metabolite of the aripiprazole.
In the step S4, the reaction conditions of the reaction in the reaction vessel are: reacting for 10-14h at 85-95 ℃.
The mass ratio of the purified Cr-MOF to the ethylenediamine in the step S4 is 50: 1-2.
The invention has the following advantages:
the method has the advantages of simple operation, saved pretreatment time and cost, good extraction effect, environmental protection, cheap and easily obtained raw materials, environment-friendly application and wide market prospect, and the material is expected to become a special material for biological sample extraction.
Drawings
FIG. 1 is a transmission electron micrograph of the Cr-MOF material MIL-101 and the modified Cr-MOF of example 1.
FIG. 2 Infrared picture of Cr-MOF material MIL-101 and modified Cr-MOF from example 1.
FIG. 3 is the UV chromatogram of 6 psychotropic drugs in example 2.
FIG. 4 is a graph showing the effect of the amount of adsorbent used on the extraction in example 4.
FIG. 5 is a graph showing the effect of pH on extraction of the buffer of example 5.
FIG. 6 is a graph showing the effect of extraction time on the extraction efficiency in example 6.
FIG. 7 shows the effect of the type of eluent on the extraction in example 7.
Detailed Description
The following examples further illustrate the invention but are not intended to limit the invention thereto.
Example 1
Preparation of modified Cr-MOF:
firstly, 800mg of chromium nitrate nonahydrate and 332mg of terephthalic acid are dissolved in 9.5ml of ultrapure water, 0.1ml of hydrofluoric acid (40 w/w%) is dripped, and the mixture is fully stirred and dissolved; reacting the prepared mixture in a solvothermal reaction kettle at 220 ℃ for 8h, and washing the prepared mixture after the reaction is finished with DMF (dimethyl formamide) and hot ethanol;
and soaking the washed material in absolute ethyl alcohol at 100 ℃ for 20h, washing and drying after the reaction is finished, then putting the material into an ammonium fluoride solution of 30mmol/L for reaction at 60 ℃ for 10h, washing with warm deionized water, and vacuum drying at 100 ℃ overnight to obtain the purified Cr-MOF (MIL-101).
Weighing 0.3g of purified MIL-101, dissolving in 30ml of absolute ethanol, adding 0.18ml of ethylenediamine, transferring into a reaction kettle, reacting for 12h at 90 ℃, washing with ethanol for multiple times after the reaction is finished, and vacuum drying for 12h at 100 ℃ to obtain the modified Cr-MOF.
As shown in FIGS. 1 and 2, FIG. 1 is a transmission electron micrograph of the obtained unmodified and modified Cr-MOF, and FIG. 2 is an infrared micrograph of the unmodified and modified Cr-MOF.
Example 2
In this example, the modified Cr-MOF prepared in example 1 was used for dispersed solid phase extraction.
The method comprises the following steps of performing dispersed solid phase extraction by using modified Cr-MOF, and analyzing three psychotropic drugs and metabolites thereof in a biological sample by combining high performance liquid chromatography, wherein the specific steps are as follows:
and (2) putting 9mg of modified Cr-MOF into a 1.5ml centrifuge tube, adding 800ml of buffer solution (PH is 3) and 200ml of serum (the concentration of six psychotropic drugs in the total system is 200ng/ml), vortexing for 5min to uniformly disperse the modified Cr-MOF in a sample, centrifuging for 5min at 8000r/min, pouring off the supernatant, and reserving the precipitate for later use.
Adding 1ml of methanol solution of 2% ammonia water into the precipitate, vortexing for 8min, centrifuging for 5min at 8000r/min after full washing, pouring the supernatant into a new centrifugal tube, blowing nitrogen for drying, and then using 1ml of ultrapure water: acetonitrile (80: 20) is redissolved and dispersed uniformly, and the prepared reaction system is subjected to high performance liquid chromatography detection, wherein the conditions of the high performance liquid chromatography are as follows:
detection conditions of high performance liquid chromatography: water acquisition UPLC C18(50mm × 2.1mm, 1.7um) is selected as chromatographic column; the detector is a diode array ultraviolet detector, and the measuring wavelength is 250 nm; sample injection amount of the autosampler: 10 ul. Mobile phase a (975ml ultrapure water + 252M ammonium acetate solution +1ml formic acid +1ml triethylamine), mobile phase B was acetonitrile and the elution procedure was as follows:
Figure BDA0003673603140000061
the results of the tests of this example are shown in the following table:
Figure BDA0003673603140000062
example 3
Testing the exclusion effect of modified Cr-MOF on proteins:
preparing 1mg/mL bovine serum albumin solution to simulate serum environment, respectively weighing 9mg of modified Cr-MOF in a 1.5mL centrifuge tube, adding 1mL bovine serum albumin solution, vortexing for 5min, centrifuging for 5min at 8000r/min, and taking supernatant in a new centrifuge tube.
And (2) determining protein in the supernatant by adopting a Folin-phenol method, putting 0.25mL of solution in the supernatant after enrichment and centrifugation into a test tube, adding 0.25mL of ultrapure water for diluting by one time, then adding 2.5mL of Folin-phenol reagent, uniformly mixing, standing at room temperature for 10min, then adding 0.25mL of Folin-phenol reagent B, immediately uniformly mixing, standing at room temperature for 30min, measuring the absorbance value at the wavelength of 500nm, and calculating the protein concentration in a sample system after medium enrichment by contrasting a standard curve.
The removal rate of the modified Cr-MOF protein is calculated by adopting the following formula:
BSA rejection(％)＝C 0 /C f ×100
C 0 postSPE supernatant concentration, C f- Initial concentration
The protein exclusion rate of the modified Cr-MOF is measured to be 92.93%, which shows that the modified Cr-MOF has better protein exclusion effect, and the protein in the serum sample system is excluded from the material while the drug is enriched, so that the step of precipitating the protein by using an organic solvent in the traditional solid phase extraction method is left.
Example 4
Effect of adsorbent dosage on drug recovery:
this example investigates the effect of adsorbent dosage on drug recovery. 3, 5, 7, 9, 11, 13 and 15mg of modified Cr-MOF are respectively weighed in 1mL of biological samples, and the concentration of six spiritual types in the samples is 200 ng/mL. From the results of FIG. 4, it can be seen that the recovery rates of risperidone, 9-hydroxyrisperidone, N-dealkylquetiapine, and aripiprazole increased with the increase of the adsorbent dosage when the dosage of the modified Cr-MOF was increased from 1mg to 9mg, indicating that the adsorption sites increased and the adsorption amount increased accordingly with the increase of the dosage of the modified Cr-MOF; however, when the amount of the adsorbent is more than 9mg, and then the amount of the modified Cr-MOF is increased, the extraction recovery rates of risperidone, 9-hydroxyrisperidone, N-dealkylated quetiapine and aripiprazole are all reduced, the extraction recovery rate of dehydroaripiprazole is increased, the recovery rate of quetiapine is basically unchanged, and the optimal amount of the extractant is 9mg in consideration of various factors.
Example 5
Effect of buffer pH on drug recovery:
this example investigates the effect of buffer pH on the surface adsorption site activity of the adsorbent. The results of extraction recovery rates under the conditions that the pH of the buffer solution is 3, 5, 7, 9 and 11 are respectively considered, and the results in FIG. 5 show that the recovery rates of six psychotropic drugs are basically gradually reduced from pH 3 to pH 11; due to protonation of the modified Cr-MOF under acidic conditions, electrostatic interaction occurs with the basic drug; the optimum pH of the extraction buffer is 3.
Example 6
Effect of extraction time on drug recovery
In the embodiment, the influence of the extraction time on the drug recovery rate is researched, the extraction time can influence the adsorption balance between the drug to be detected and the modified MOF material and influence the drug extraction recovery rate, the recovery rate conditions of six spirits when the extraction time is respectively 1min, 2 min, 5min, 8min and 11min are examined, the results of fig. 6 show that the recovery rates of all the drugs are increased when the extraction time is increased from 1min to 5min, and after the extraction time is continuously prolonged, the recovery rates of the rest drugs are reduced except for the increase of 9-hydroxyrisperidone, which indicates that the adsorption is balanced, so that the optimal extraction time is 5 min.
Example 7
Investigation of the type of eluent on the recovery of the drug
In this example, the influence of different elution solvents on the elution efficiency of the drug to be detected adsorbed on the modified Cr-MOF was studied, and in this example, the influence of three pure organic solvents, namely methanol, acetonitrile and acetone, on the extraction recovery rate was studied, and the results in fig. 7 show that methanol has the best elution efficiency for the three psychotropic drugs and their metabolites, and therefore methanol is the best elution solvent.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. An analysis method for detecting chemicals based on modified Cr-MOF is characterized in that: the method comprises the steps of removing protein from a serum sample to be detected by a dispersive solid-phase extraction technology, enriching, and carrying out ultraviolet detection to obtain the concentration of a related medicament, and specifically comprises the following steps:
1) taking the modified Cr-MOF in a centrifugal tube, adding a buffer solution and serum into the centrifugal tube, swirling to uniformly disperse the modified Cr-MOF in a sample, centrifuging for 4-6min at 80000-10000r/min, and pouring out a supernatant; wherein the ratio of the buffer solution to the serum is 4: 1;
2) adding an elution solution into the precipitate obtained in the step 1), performing vortex, performing full elution, centrifuging for 5min at 8000r/min, pouring the supernatant into a new centrifugal tube, blowing nitrogen for drying, re-dissolving by using a re-solution, dispersing uniformly, and performing high performance liquid chromatography detection on the prepared reaction system.
2. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: the preparation method of the modified Cr-MOF in the step 1) comprises the following steps:
s1, dissolving chromium nitrate nonahydrate and terephthalic acid in ultrapure water, dropwise adding a hydrofluoric acid aqueous solution with the mass fraction of 40%, and fully stirring to dissolve the chromium nitrate nonahydrate, the terephthalic acid, the ultrapure water and the hydrofluoric acid aqueous solution in a mass ratio of (80-90) to (30-40) to 1 (10-20);
s2, reacting the mixture prepared in the step 1) in a solvent thermal reaction kettle at the temperature of 210 ℃ and 230 ℃ for 7-9h, and washing the prepared mixture with DMF and hot ethanol;
s3, soaking the sample obtained in the step 2) in absolute ethyl alcohol for 18-22h, washing and drying after the reaction is finished, then putting the sample into an ammonium fluoride solution for reaction for 9-11h at the temperature of 58-62 ℃, washing with warm deionized water, and carrying out vacuum drying at the temperature of 90-110 ℃ overnight to obtain purified Cr-MOF;
s4, dissolving the purified Cr-MOF in absolute ethyl alcohol, continuously adding ethylenediamine, transferring into a reaction kettle for reaction, washing with the ethyl alcohol for multiple times after the reaction is finished, and carrying out vacuum drying at 90-11 ℃ for 10-14h to obtain the modified Cr-MOF.
3. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: in the step 1), the buffer solution is an acidic aqueous solution.
4. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: the pH value of the buffer solution is 3-5.
5. The method of claim 1, wherein the method comprises the following steps: the elution solution in the step 2) is methanol solution, methanol solution with 2% ammonia water by volume ratio, acetonitrile or acetone.
6. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: the complex solution in the step 2) is acetonitrile water solution;
the volume ratio of acetonitrile to water in the acetonitrile water solution is 1: 4.
7. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: the detection conditions of the high performance liquid chromatography in the step 2) are as follows: using water ACQUity UPLC C18 50mm × 2.1mm, 1.7um as chromatographic column; the detector is a diode array ultraviolet detector, and the measuring wavelength is 250 nm; sample injection amount of the autosampler: 20 uL; the mobile phase A is: 975ml of ultrapure water +25ml of 2M ammonium acetate solution +1ml of formic acid +1ml of triethylamine, mobile phase B being acetonitrile.
8. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: the psychotropic drugs are risperidone, quetiapine, N-dealkylated quetiapine, dehydroaripiprazole, aripiprazole and 9-hydroxyrisperidone which is a metabolite of the aripiprazole.
9. The modified Cr-MOF based assay method for the detection of chemicals according to claim 2, characterized in that: in the step S4, the reaction conditions of the reaction in the reaction vessel are: reacting for 10-14h at 85-95 ℃.
10. The modified Cr-MOF based assay method for the detection of chemicals according to claim 1, characterized in that: the mass ratio of the purified Cr-MOF to the ethylenediamine in the step S4 is 50: 1-2.
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