CN112321763A - Casidone derivative molecularly imprinted polymer and preparation method and application thereof - Google Patents
Casidone derivative molecularly imprinted polymer and preparation method and application thereof Download PDFInfo
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Abstract
A molecularly imprinted polymer of a cassidone derivative and a preparation method and application thereof are synthesized by a non-covalent precipitation method by taking 1- (4-methylphenyl) -2-dimethylamino-1-acetone as a template molecule, methacrylic acid as a functional monomer, Ethylene Glycol Dimethacrylate (EGDMA) as a cross-linking agent and Azobisisobutyronitrile (AIBN) as an initiator. The invention can prepare the polymer with good stability and large adsorption capacity, and has strong selective binding capacity on the molecule of the carsinone derivative.
Description
Technical Field
The invention relates to a technology in the field of molecular imprinting, in particular to a cathinone derivative molecular imprinting polymer and a preparation method and application thereof.
Background
According to the 2019 world drug report, about 2.7 hundred million people take drugs each year, nearly 3500 million people are addicted, and nearly 60 million people directly die of drug abuse. Among them, the New Psychoactive Substances (NPS) are the "third generation drugs" that have been introduced worldwide since the 21 st century after the traditional drugs (such as opium, marijuana, coca and derivatives thereof) and the New synthetic drugs (such as methamphetamine, ecstasy, magical, etc.). With the rapid development of economic globalization and social informatization, the abuse problem of new mental active substances is increasingly severe. Casidone belongs to monoamine alkaloids, has a chemical name of 2-amino-1-phenyl-1-acetone, has a molecular structure and a pharmacological action similar to those of amphetamine stimulants, and can generate a euphoric effect. The synthesized casitone derivatives are artificial compounds developed based on casitone structures in the late 1920 years, one more ketone group structure is arranged on a carbon atom at the beta position of a benzene ring, the casitone derivatives belong to new psychoactive substances, and up to 148 types of casitone synthesized substances are found by 2017. The synthetic casitone derivatives are usually white or brown powders in appearance, very close to bath salts, and are generally distributed on the market under the names of bath salts, vegetable fertilizers and the like. As a central nervous system stimulant, the stimulant mainly generates the effect of simulating the traditional narcotic ***e, amphetamine or methamphetamine by regulating the concentration of dopamine, norepinephrine or 5-hydroxytryptamine, so as to cause a series of mental symptoms such as irritability, dysphoria, psychomimetic symptoms and the like, and is accompanied with serious side effects of a nervous system, a cardiovascular system and a respiratory system.
The methods commonly used for detecting the novel psychic active substances of the casinoses comprise chemical detection methods, chromatography, mass spectrometry, capillary electrophoresis, immunoassay and the like, and although the methods have certain sensitivity and accuracy, the methods have obvious defects, such as poor specificity and sensitivity of the chemical detection methods; the problems of complex pretreatment, long time consumption, large reagent dosage and the like exist in the chromatography and mass spectrometry, and simultaneously, due to the loss of some newly appeared standard substances of the cassiophenone substances, the chromatographic analysis can not realize synchronous confirmation; the immunoassay method needs a specially-made imported kit, and the acquisition of the biological enzyme is difficult, the cost is high, the experimental conditions are harsh, and the like; the capillary electrophoresis method has a low throughput and thus has poor preparation ability. Therefore, the development and screening of a synthetic method for detecting the cassidone derivatives, which has the advantages of strong specificity, high sensitivity, low cost and convenient use, is of great significance.
Molecular Imprinting Technology (MIT), also known as Molecular template technology, is a technology for preparing polymers with specific and specific recognition effects on a specific target molecule, and is a family edge branch developed by combining the advantages of polymer chemistry, material chemistry, Molecular recognition, biochemistry and other disciplines in recent years. The molecular engram polymer is usually prepared by taking a certain compound as a template, carrying out cross-linking polymerization in the presence of a functional monomer and a cross-linking agent, and after the polymerization is finished, washing away the template molecules which are connected by covalent bonds or non-covalent bonds to form 'cavities' which are complementary to the spatial structure of the original engram molecule and have multiple action sites. The imprinted polymer with the memory function can selectively adsorb the imprinted molecules. Therefore, compared with other traditional separation detection technologies, the MIT technology has the advantages of being good in structure predetermination, specific identification, selectivity and practicability and the like.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a cathinone derivative molecularly imprinted polymer, a preparation method and application thereof, and the polymer with good stability and large adsorption capacity can be prepared, and has strong selective binding capacity on cathinone derivative molecules.
The invention is realized by the following technical scheme:
the invention relates to a preparation method of a cathinone derivative molecularly imprinted polymer, which is characterized in that 1- (4-methylphenyl) -2-dimethylamino-1-acetone, namely 4-MDMC is used as a template molecule, methacrylic acid is used as a functional monomer, Ethylene Glycol Dimethacrylate (EGDMA) is used as a cross-linking agent, and Azobisisobutyronitrile (AIBN) is used as an initiator, and the molecularly imprinted polymer is synthesized by a non-covalent precipitation method.
The molecular structure of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone is as follows:
The non-covalent precipitation method comprises the following specific steps: completely dissolving template molecules and functional monomers in acetonitrile at room temperature, sequentially adding a cross-linking agent and an initiator, ultrasonically dispersing, blowing with nitrogen to remove oxygen, stirring at constant temperature in a water bath heating environment, fully reacting to obtain a white blocky compound, and finally grinding and eluting the template molecules to obtain Molecularly Imprinted Polymers (MIPs).
The elution template molecule is characterized in that: and eluting the template molecules in the ground polymer by using a methanol-acetic acid mixed solution.
The eluted template molecules are preferably further washed with methanol to neutrality after elution and dried.
The mol ratio of the template molecule to the functional monomer is preferably 1: 4.
The preferable dosage of the acetonitrile is 5-10 mL.
The time for ultrasonic dispersion is preferably 10-15 min.
The molar ratio of the template molecule to the cross-linking agent is preferably 1: 10.
The amount of the initiator is preferably 10 mg.
The methanol-acetic acid mixed solution preferably has a methanol-acetic acid volume ratio of 9: 1.
The water bath is used for heating, and the heating is preferably carried out for 24 hours at the temperature of 70 ℃.
The adsorption quantity of the cassidone derivative imprinted molecular polymer to 1- (4-methylphenyl) -2-dimethylamino-1-acetone is 0.42-2.76 mg/g.
The invention relates to application of the molecularly imprinted polymer, which is used for detecting the adsorption performance of 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
The adsorption performance detection specifically comprises the following steps: and (3) fully mixing the molecularly imprinted polymer with a methanol solution containing the 1- (4-methylphenyl) -2-dimethylamino-1-acetone to be detected, measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant in the mixed solution by HPLC, and calculating the adsorption quantity of the cathinone derivative molecularly imprinted polymer to the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
The adsorption capacity Q is (0.01 mg/mL-C)e) X 10mL/10mg, wherein: ceThe concentration of 1- (4-methylphenyl) -2-dimethylamino-1-propanone in the supernatant was determined.
The methanol solution containing the 1- (4-methylphenyl) -2-dimethylamino-1-acetone to be detected is preferably 10mL of the methanol solution of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone with the concentration of 0.01 mg/mL.
The dosage of the molecular engram polymer is preferably 10 mg.
The sufficient mixing means that: the mixed solution was shaken at room temperature for 12 h.
The supernatant fluid is: sucking 1mL of the mixed solution after full mixing, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant.
Technical effects
The method takes methacrylic acid as a functional monomer, prepares the cathinone derivative molecularly imprinted polymer with a recognition hole by a non-covalent precipitation polymerization method, and applies the cathinone derivative molecularly imprinted polymer to qualitative and quantitative detection and analysis of the cathinone derivative.
Compared with the prior art, the method is simple and easy to operate, the prepared Casidone derivative imprinted molecular polymer has good stability, and has specific adsorption on 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
Drawings
FIG. 1 is a synthetic route diagram according to the present invention;
FIG. 2 is a Fourier transform infrared (FT-IR) spectrum of a molecularly imprinted polymer of a casitone derivative synthesized in example 1 of the present invention before and after elution;
FIG. 3 is a graph showing adsorption kinetics of a molecularly imprinted polymer of a casitone derivative prepared in example 1 on 1- (4-methylphenyl) -2-dimethylamino-1-propanone.
Detailed Description
Example 1
As shown in fig. 1, the present embodiment includes the following steps:
step 1) dissolving 0.1mmol of template molecule 1- (4-methylphenyl) -2-dimethylamino-1-acetone and 0.4mmol of functional monomer methacrylic acid in 5mL of acetonitrile, performing ultrasonic treatment for 10min to accelerate dissolution, and performing prepolymerization for 12h at room temperature to ensure that the functional monomer and the template molecule fully act;
step 2) adding 1mmol of cross-linking agent ethylene glycol dimethacrylate and 10mg of initiator azobisisobutyronitrile, performing ultrasonic treatment for 10min to fully dissolve substances in the system and degas for 10min, introducing nitrogen for 10-15 min to remove oxygen, sealing, and stirring in a constant-temperature water bath at 70 ℃ to react for 24h to obtain a white block polymer;
and 3) grinding, screening and settling the white blocks, performing Soxhlet extraction by using a methanol-acetic acid mixed solution (volume ratio of 9:1) as an extraction solvent, removing template molecules and unreacted substances, repeatedly washing the white blocks to be neutral by using methanol to remove residual acetic acid, and performing vacuum drying for 48 hours to obtain the imprinted polymer replacing the template molecules.
The invention relates to a cathinone derivative molecularly imprinted polymer prepared by the method, and the molecular structure of the cathinone derivative molecularly imprinted polymer is
The molecularly imprinted polymer prepared by the method is subjected to adsorption performance detection, and the method specifically comprises the following steps:
step 1) adding 10mg of a cathinone derivative molecularly imprinted polymer into 10mL of 0.01mg/mL 1- (4-methylphenyl) -2-dimethylamino-1-acetone methanol solution, shaking for 12h at room temperature, sucking 1mL of mixed solution, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant;
and 2) measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant obtained in the step by using HPLC (high performance liquid chromatography), and calculating the adsorption quantity of the molecularly imprinted polymer of the cathinone derivative on the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
The adsorption quantity Q of the molecularly imprinted polymer of the cassidone derivative to the 1- (4-methylphenyl) -2-dimethylamino-1-acetone is equal to (0.01 mg/mL-C)e) X 10mL/10mg, wherein: ceIs the concentration of 1- (4-methylphenyl) -2-dimethylamino-1-propanone in the supernatant; by calculation, the adsorption amount of the molecularly imprinted polymer of the cathinone derivative to 1- (4-methylphenyl) -2-dimethylamino-1-propanone was 2.76 mg/g.
As shown in FIG. 2, 2954cm is shown-1Is located at 1719cm and is C-H stretching vibration peak-1At 1452cm, C ═ O stretching vibration peak on carboxyl group-1Is treated as a stretching vibration peak of a benzene ring framework, and is eluted at 1640cm-1The C ═ O stretching vibration peak at the molecule of the casitone derivative disappeared, indicating that the template molecule had eluted.
As shown in FIG. 3, the adsorption of the molecularly imprinted polymer of the cathinone derivative to 1- (4-methylphenyl) -2-dimethylamino-1-acetone is close to the maximum value within 5min, and the adsorption amount is almost unchanged along with the prolonging of time, namely the adsorption amount reaches the balance, which shows that the molecularly imprinted polymer has better adsorption kinetics, because the molecularly imprinted polymer of the cathinone derivative prepared by the non-covalent precipitation method has a better spatial structure, and the time for the template molecule to enter the hole matched with the shape and the binding group of the molecularly imprinted polymer is shorter, so that the molecularly imprinted polymer has a faster adsorption speed.
Example 2
The embodiment comprises the following steps:
step 1) dissolving 0.1mmol of template molecule 1- (4-methylphenyl) -2-dimethylamino-1-acetone and 0.6mmol of functional monomer methacrylic acid in 5mL of acetonitrile, performing ultrasonic treatment for 10min to accelerate dissolution, and performing prepolymerization for 12h at room temperature to ensure that the functional monomer and the template molecule fully act;
step 2) adding 1mmol of cross-linking agent ethylene glycol dimethacrylate and 10mg of initiator azobisisobutyronitrile, ultrasonically dissolving and degassing substances in the system fully for 10min, introducing nitrogen for 10-15 min to remove oxygen, sealing, stirring and reacting for 24h in a constant-temperature water bath at 70 ℃, and obtaining a white block polymer after polymerization;
and 3) grinding, screening and settling the white blocks, performing Soxhlet extraction by using a methanol-acetic acid mixed solution (volume ratio of 9:1) as an extraction solvent, removing template molecules and unreacted substances, repeatedly washing the white blocks to be neutral by using methanol to remove residual acetic acid, and performing vacuum drying for 48 hours to obtain the imprinted polymer replacing the template molecules.
The detection of the adsorption performance of the prepared cathinone derivative molecularly imprinted polymer comprises the following steps:
step 1) adding 10mg of a cathinone derivative molecularly imprinted polymer into 10mL of 0.01mg/mL 1- (4-methylphenyl) -2-dimethylamino-1-acetone methanol solution, shaking for 12h at room temperature, sucking 1mL of mixed solution, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant;
and step 2) measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant obtained in the step 1 by using HPLC (high performance liquid chromatography), and calculating the adsorption quantity of the molecularly imprinted polymer of the cathinone derivative on the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
In this example, the adsorption amount of the molecularly imprinted polymer of the Casidone derivative to 1- (4-methylphenyl) -2-dimethylamino-1-propanone was 0.42 mg/g.
Example 3
The embodiment comprises the following steps:
step 1) dissolving 0.1mmol of template molecule 1- (4-methylphenyl) -2-dimethylamino-1-acetone and 1mmol of functional monomer methacrylic acid in 5mL of acetonitrile, performing ultrasonic treatment for 10min to accelerate dissolution, and performing prepolymerization for 12h at room temperature to ensure that the functional monomer and the template molecule fully act;
step 2) adding 1mmol of cross-linking agent ethylene glycol dimethacrylate and 10mg of initiator azobisisobutyronitrile, ultrasonically dissolving and degassing substances in the system fully for 10min, introducing nitrogen for 10-15 min to remove oxygen, sealing, stirring and reacting for 24h in a constant-temperature water bath at 70 ℃, and obtaining a white block polymer after polymerization;
and 3) grinding, screening and settling the white blocks, performing Soxhlet extraction by using a methanol-acetic acid mixed solution (volume ratio of 9:1) as an extraction solvent, removing template molecules and unreacted substances, repeatedly washing the white blocks to be neutral by using methanol to remove residual acetic acid, and performing vacuum drying for 48 hours to obtain the imprinted polymer replacing the template molecules.
The detection of the adsorption performance of the prepared cathinone derivative molecularly imprinted polymer comprises the following steps:
step 1) adding 10mg of a cathinone derivative molecularly imprinted polymer into 10mL of 0.01mg/mL 1- (4-methylphenyl) -2-dimethylamino-1-acetone methanol solution, shaking for 12h at room temperature, sucking 1mL of mixed solution, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant;
and step 2) measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant obtained in the step 1 by using HPLC (high performance liquid chromatography), and calculating the adsorption quantity of the molecularly imprinted polymer of the cathinone derivative on the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
In this example, the adsorption amount of the molecularly imprinted polymer of the Casidone derivative to 1- (4-methylphenyl) -2-dimethylamino-1-propanone was 0.56 mg/g.
Example 4
The embodiment comprises the following steps:
step 1) dissolving 0.1mmol of template molecule 1- (4-methylphenyl) -2-dimethylamino-1-acetone and 0.4mmol of functional monomer methacrylic acid in 5mL of acetonitrile, performing ultrasonic treatment for 10min to accelerate dissolution, and performing prepolymerization for 12h at room temperature to ensure that the functional monomer and the template molecule fully act;
step 2) adding 2mmol of crosslinking agent ethylene glycol dimethacrylate and 10mg of initiator azobisisobutyronitrile, ultrasonically dissolving and degassing substances in the system fully for 10min, introducing nitrogen for 10-15 min to remove oxygen, sealing, stirring and reacting for 24h in a constant-temperature water bath at 70 ℃, and obtaining a white block polymer after polymerization;
and 3) grinding, screening and settling the white blocks, performing Soxhlet extraction by using a methanol-acetic acid mixed solution (volume ratio of 9:1) as an extraction solvent, removing template molecules and unreacted substances, repeatedly washing the white blocks to be neutral by using methanol to remove residual acetic acid, and performing vacuum drying for 48 hours to obtain the imprinted polymer replacing the template molecules.
The detection of the adsorption performance of the prepared cathinone derivative molecularly imprinted polymer comprises the following steps:
step 1) adding 10mg of a cathinone derivative molecularly imprinted polymer into 10mL of 0.01mg/mL 1- (4-methylphenyl) -2-dimethylamino-1-acetone methanol solution, shaking for 12h at room temperature, sucking 1mL of mixed solution, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant;
and step 2) measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant obtained in the step 1 by using HPLC (high performance liquid chromatography), and calculating the adsorption quantity of the molecularly imprinted polymer of the cathinone derivative on the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
In this example, the adsorption amount of the molecularly imprinted polymer of the Casidone derivative to 1- (4-methylphenyl) -2-dimethylamino-1-propanone was 1.80 mg/g.
Example 5
The embodiment comprises the following steps:
step 1) dissolving 0.1mmol of template molecule 1- (4-methylphenyl) -2-dimethylamino-1-acetone and 0.6mmol of functional monomer methacrylic acid in 5mL of acetonitrile, performing ultrasonic treatment for 10min to accelerate dissolution, and performing prepolymerization for 12h at room temperature to ensure that the functional monomer and the template molecule fully act;
step 2) adding 3mmol of crosslinking agent ethylene glycol dimethacrylate and 10mg of initiator azobisisobutyronitrile, ultrasonically dissolving and degassing substances in the system fully for 10min, introducing nitrogen for 10-15 min to remove oxygen, sealing, stirring and reacting for 24h in a constant-temperature water bath at 70 ℃, and obtaining a white block polymer after polymerization;
and 3) grinding, screening and settling the white blocks, performing Soxhlet extraction by using a methanol-acetic acid mixed solution (volume ratio of 9:1) as an extraction solvent, removing template molecules and unreacted substances, repeatedly washing the white blocks to be neutral by using methanol to remove residual acetic acid, and performing vacuum drying for 48 hours to obtain the imprinted polymer replacing the template molecules.
The detection of the adsorption performance of the prepared cathinone derivative molecularly imprinted polymer comprises the following steps:
step 1) adding 10mg of a cathinone derivative molecularly imprinted polymer into 10mL of 0.01mg/mL 1- (4-methylphenyl) -2-dimethylamino-1-acetone methanol solution, shaking for 12h at room temperature, sucking 1mL of mixed solution, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant;
and step 2) measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant obtained in the step 1 by using HPLC (high performance liquid chromatography), and calculating the adsorption quantity of the molecularly imprinted polymer of the cathinone derivative on the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
In this example, the adsorption amount of the molecularly imprinted polymer of the Casidone derivative to 1- (4-methylphenyl) -2-dimethylamino-1-propanone was 0.79 mg/g.
Compared with the prior art, the molecularly imprinted polymer of the cassidone derivative obtained by the method has the advantages of high adsorption capacity, good stability, fast mass transfer and the like, can avoid the obvious defects of the conventional detection method when being applied to the actual detection of the cassidone derivative, has the characteristics of strong specificity, high sensitivity, low cost, convenient use and the like, and has very important significance for the detection of new psychoactive substances of the cassidone in actual samples.
The foregoing embodiments may be modified in many different ways by those skilled in the art without departing from the spirit and scope of the invention, which is defined by the appended claims and all changes that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (10)
1. A preparation method of a cathinone derivative molecularly imprinted polymer is characterized in that 1- (4-methylphenyl) -2-dimethylamino-1-acetone is used as a template molecule, methacrylic acid is used as a functional monomer, ethylene glycol dimethacrylate is used as a cross-linking agent, and azobisisobutyronitrile is used as an initiator, and a non-covalent precipitation method is adopted to synthesize the molecularly imprinted polymer;
the molecular structure of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone is as follows:
2. the method for preparing a molecularly imprinted polymer of a casitone derivative according to claim 1, wherein the non-covalent precipitation method is specifically: completely dissolving template molecules and functional monomers in acetonitrile at room temperature, sequentially adding a cross-linking agent and an initiator, ultrasonically dispersing, blowing with nitrogen to remove oxygen, stirring at constant temperature in a water bath heating environment, fully reacting to obtain a white blocky compound, and finally grinding and eluting the template molecules to obtain the molecularly imprinted polymer.
3. The method of claim 2, wherein the elution template molecule is selected from the group consisting of: and eluting the template molecules in the ground polymer by using a methanol-acetic acid mixed solution.
4. The method for preparing a molecularly imprinted polymer of a casitone derivative according to any of the preceding claims, wherein the molar ratio of the template molecule to the functional monomer is 1: 4;
the using amount of the acetonitrile is 5-10 mL;
the ultrasonic dispersion time is 10-15 min;
the molar ratio of the template molecules to the cross-linking agent is 1: 10;
the dosage of the initiator is 10 mg;
the methanol-acetic acid mixed solution is prepared by mixing methanol and acetic acid in a volume ratio of 9: 1.
5. A molecularly imprinted polymer of a Cascade derivative, which is prepared by the method of any one of the preceding claims, wherein the adsorption amount of the molecularly imprinted polymer of the Cascade derivative to 1- (4-methylphenyl) -2-dimethylamino-1-propanone is 0.42-2.76 mg/g.
6. Use of a molecularly imprinted polymer according to any of the preceding claims for the detection of the adsorption properties of 1- (4-methylphenyl) -2-dimethylamino-1-propanone.
7. The use of claim 6, wherein the adsorption performance test is as follows: and (3) fully mixing the molecularly imprinted polymer with a methanol solution containing the 1- (4-methylphenyl) -2-dimethylamino-1-acetone to be detected, measuring the concentration of the 1- (4-methylphenyl) -2-dimethylamino-1-acetone in the supernatant in the mixed solution by HPLC, and calculating the adsorption quantity of the cathinone derivative molecularly imprinted polymer to the 1- (4-methylphenyl) -2-dimethylamino-1-acetone.
8. The use according to claim 7, wherein the amount of adsorbed Q ═ C (0.01 mg/mL-C)e) X 10mL/10mg, wherein: ceThe concentration of 1- (4-methylphenyl) -2-dimethylamino-1-propanone in the supernatant was determined.
9. The use according to claim 6, wherein the methanol solution containing 1- (4-methylphenyl) -2-dimethylamino-1-propanone to be tested is 10mL of 1- (4-methylphenyl) -2-dimethylamino-1-propanone at a concentration of 0.01 mg/mL.
10. The use according to claim 6, wherein the supernatant is: sucking 1mL of the mixed solution after full mixing, adding the mixed solution into a 2mL centrifuge tube, centrifuging for 20min, and taking supernatant.
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| CN114878660A (en) * | 2022-04-29 | 2022-08-09 | 上海市刑事科学技术研究院 | Graphene oxide surface molecularly imprinted composite material, preparation method and application |
| CN115144489A (en) * | 2022-06-09 | 2022-10-04 | 大连海事大学 | Application of virtual template molecularly imprinted polymer in detection of synthesized casitone drugs |
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| CN115144489A (en) * | 2022-06-09 | 2022-10-04 | 大连海事大学 | Application of virtual template molecularly imprinted polymer in detection of synthesized casitone drugs |
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