CN115855906A - Method for detecting amphetamine in drugs based on anthracene-based probe - Google Patents
Method for detecting amphetamine in drugs based on anthracene-based probe Download PDFInfo
- Publication number
- CN115855906A CN115855906A CN202211650429.6A CN202211650429A CN115855906A CN 115855906 A CN115855906 A CN 115855906A CN 202211650429 A CN202211650429 A CN 202211650429A CN 115855906 A CN115855906 A CN 115855906A
- Authority
- CN
- China
- Prior art keywords
- anthracene
- based probe
- amphetamine
- dicyanoethylene
- aldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Landscapes
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention provides a method for detecting amphetamine in drugs by using an anthracene-based probe, which respectively takes aldehyde group and dicyanovinyl group as identification groups, anthracene as a luminescence center and benzothiadiazole as a pi-bridge and can be obtained by Suzuki coupling and Kenaughel condensation reaction. Wherein, the fluorescence color of the anthracene-based probe taking the aldehyde group as the identification group changes from orange to yellow before and after the amphetamine is added; an anthracene-based probe taking dicyanovinyl as a recognition group changes the fluorescent color from dark red to yellow before and after the amphetamine is added; both probes exhibited ratiometric fluorescent signals. In order to facilitate the field practical detection application, the probe is loaded on a sponge substrate to prepare an analysis card, after the amphetamine solution is dripped, the fluorescence color is changed from orange to green, the colorimetric effect is changed from orange to light yellow, and the detection is not interfered by other common drugs, amine substances and the like. The invention has the advantages of high sensitivity, high specificity, rapidness and visualization, and has wide application prospect in drug field analysis.
Description
Technical Field
The invention belongs to the field of drug detection, and provides a method for detecting amphetamine in drugs by using an anthracene-based probe. The probe has low detection limit, strong anti-interference performance and short reaction time, and can realize the purpose of detecting the amphetamine in drugs by fluorescence in real time at low cost.
Background
Drugs harm the health of human bodies and easily induce other crimes, and in actual vending and abuse scenes, the characteristics of complex and changeable components and forms, strong camouflage and the like of the drugs bring great challenges for field detection.
Amphetamine (Amphetamine), which belongs to an analeptic psychotropic drug, is a strong addictive drug, which is mainly used for preventing dopamine inhibitor from releasing to enable people to have a euphoric experience, so that the Amphetamine has serious smuggling and abuse, becomes a representative second type of synthetic drugs, realizes high sensitivity, quick response and selective field detection, and has great significance for strictly controlling abuse, transportation, buying and selling of the drugs and further effectively reducing crimes.
Compared with other drug field detection modes, the method comprises the following steps: the optical sensing method mainly based on colorimetric and fluorescence technologies can change the stacking state or chemical structure of the identification group by utilizing the selective interaction between the designed identification group and a target molecule, and the generated change optical signal intensity is accumulated to output a detectable visual signal.
The invention discloses a method for detecting amphetamine in drugs based on an anthracene-based probe, which realizes high-specificity and high-sensitivity on-site rapid fluorescence detection of the phenylpropylamine in the form of a detection reagent or a sponge analysis card by using the probe with anthracene as a fluorophore, benzothiadiazole as a pi-bridge and aldehyde group or dicyanovinyl group as a reaction site.
Disclosure of Invention
The invention aims to provide a method for detecting amphetamine in drugs based on anthracene-based probes, wherein two anthracene-based probes in the method can realize ratiometric fluorescence detection of amphetamine in drugs. The two anthracene-based probes respectively take aldehyde groups and dicyanovinyl groups as recognition groups, anthracene as a luminescence center and diazosulfide as a pi-bridge, and can be obtained through Suzuki coupling and Kenaohnerl condensation reaction. Wherein, the fluorescence color of the anthracene-based probe taking the aldehyde group as the identification group changes from orange to yellow before and after the amphetamine is added; an anthracene-based probe taking dicyanovinyl as a recognition group changes the fluorescent color from dark red to yellow before and after the amphetamine is added; both probes exhibited ratiometric fluorescent signals. In order to facilitate the field practical detection application, the dicyanoethylene-anthracene-based probe is loaded on a sponge substrate to prepare an analysis card, after the amphetamine solution is dripped, the fluorescence color is changed from orange to green, the colorimetric effect is changed from orange to light yellow, and the detection is not interfered by other common drugs, amine substances and the like. The invention has the advantages of high sensitivity, high specificity, rapidness and visualization, and has wide application prospect in drug field analysis.
The invention discloses a method for detecting amphetamine in drugs based on an anthryl probe, which comprises the following steps:
preparing a detection reagent:
a. weighing 2-anthraceneboronic acid and 7-bromo-4-aldehyde benzo [ C ] [1,2,5] thiadiazole according to a molar ratio of 1:1, placing the weighed materials into a 100mL three-neck flask, adding 10mL of toluene, 5mL of pure water and 10mL of tert-butyl alcohol, controlling the reaction temperature to be 85 ℃ and stirring under the protection of nitrogen atmosphere, then slowly adding sodium carbonate and a catalyst tetrakis (triphenylphosphine) palladium, and reacting for 36 hours in a dark place;
b. after the reaction is finished, washing the reaction product to be neutral by using a dilute hydrochloric acid solution, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, carrying out suction filtration and spin drying to obtain an aldehyde-anthracene-based probe crude product, and sequentially carrying out methanol recrystallization and column chromatography purification to obtain an orange solid, namely the aldehyde-anthracene-based probe;
c. b, placing the aldehyde-anthracene-based probe and malononitrile obtained in the step b into a 100mL three-neck flask according to a molar ratio of 1:1, adding 1mL of pyridine and 10mL of toluene, controlling the reaction temperature to be 60 ℃ and stirring under the protection of nitrogen atmosphere, and reacting for 24 hours in a dark place;
d. after the reaction is finished, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, performing suction filtration and spin drying to obtain a crude product of the dicyanoethylene-anthracene-based probe, and sequentially performing methanol recrystallization and column chromatography purification on the crude product to obtain a red solid as the dicyanoethylene-anthracene-based probe;
e. respectively dissolving the aldehyde-anthracene-based probe obtained in the step b and the dicyanoethylene-anthracene-based probe obtained in the step d in tetrahydrofuran, and preparing an aldehyde-anthracene-based probe solution and a dicyanoethylene-anthracene-based probe solution with the concentration of 0.01-1mmol/L after ultrasonic dissolution to obtain two detection reagents for identifying amphetamine;
detection of amphetamine with aldehyde-anthracene-based probe:
f. e, putting 450 mu L of the 0.05mmol/L aldehyde-anthracene-based probe solution obtained in the step e into a test tube, adding 50 mu L of amphetamine solution with the concentration of 5mmol/L, after full reaction, recording a fluorescence spectrum and an optical photo under the 365nm ultraviolet light excitation condition, and observing the signal change of a fluorescence characteristic emission peak before and after the reaction;
detecting the amphetamine by using a dicyanoethylene-anthracene-based probe:
g. e, putting 450 mu L of the 0.05mmol/L dicyanoethylene-anthracene-based probe solution obtained in the step e into a test tube, then adding 50 mu L amphetamine solution with the concentration of 5mmol/L, after full reaction, recording a fluorescence spectrum and an optical photo under the 365nm ultraviolet light excitation condition, and observing the signal change of a fluorescence characteristic emission peak before and after the reaction;
or soaking the polyurethane sponge in 0.1mmol/L dicyanoethylene-anthracene-based probe solution, taking out the polyurethane sponge after complete soaking, drying the polyurethane sponge in an oven at 40 ℃, and obtaining the sponge analysis card loaded with the dicyanoethylene-anthracene-based probe after complete volatilization of the solvent; and (3) sucking 20 mu L of the amphetamine solution to be detected, dripping the amphetamine solution to be detected on a sponge analysis card loaded with a dicyanoethylene-anthracene-based probe, and observing colorimetric and fluorescent changes under the conditions of sunlight and 365nm illumination.
The invention relates to a method for detecting amphetamine in drugs based on an anthracene-based probe, wherein the chemical names of an aldehyde-anthracene-based probe and a dicyanoethylene-anthracene-based probe are respectively 7- (anthracene-2-yl) benzo [2,1-c ] [1,2,5] thiadiazacyclo-4-formaldehyde (short for aldehyde-anthracene-based probe) and 2- { [7- (anthracene-2-yl) benzo [2,1-c ] [1,2,5] thiadiazacyclo-4-yl ] methylidene } malononitrile (short for dicyanoethylene-anthracene-based probe), and the aldehyde-anthracene-based probe and the dicyanoethylene-anthracene-based probe can be obtained by Suzuki coupling and Kennavelal condensation reaction, and the chemical structural formulas (I) and (II) corresponding to the aldehyde-anthracene-based probe and the dicyanoethylene-anthracene-based probe are respectively:
according to the method for detecting the amphetamine in the drugs by using the anthracene-based probe, the anthracene-based probe respectively taking aldehyde group and dicyanovinyl group as response groups can realize the ratio fluorescence detection of the amphetamine in the drugs. Wherein the naked eye detection limit of the dicyanoethylene-anthracene-based probe to the phenylpropylamine can reach 60 mu mol/L, and the detection linear range is 20-500 mu mol/L. When the sponge analysis card loaded with the dicyanoethylene-anthracene-based probe is used for field detection application simulation, the fluorescence color of the sponge analysis card is changed from orange to green within 60s of the dropwise addition of the narcotic amphetamine, the colorimetric effect is changed from orange to light yellow, and other common narcotic and amine substances have no obvious interference on detection of the phenylpropylamine. The invention has no special limitation when in use, can quickly finish qualitative detection without pretreatment of an object to be detected at room temperature, has simple operation, economy and practicality, high specificity and sensitivity and stable and repeatable results, and has the advantages of easy practical application and popularization in the field of on-site instant detection.
The anthracene-based probe has response groups of aldehyde group and dicyanovinyl group to the phenylpropylamine. In the presence of amphetamine, both probes exhibited more pronounced ratiometric fluorescence changes, i.e., orange to yellow (aldehyde-anthracene-based probes) and dark red to yellow (dicyanoethylene-anthracene-based probes); when the probe is loaded on a sponge substrate to prepare an analysis card, after the amphetamine solution is dripped, obvious fluorescence response change can occur within 60s, and simultaneously, a color comparison phenomenon that orange color is changed into faint yellow color is presented; the probe has good identification capability on the phenylpropylamine, and the detection of the phenylpropylamine is not interfered by other common drugs, amine substances and the like. The invention provides a good research foundation and an effective investigation means for the rapid on-site analysis of drugs.
The invention relates to a method for detecting amphetamine in drugs by using anthracene-based probe fluorescence, which has the detection principle that: the amido of the object to be detected is subjected to nucleophilic attack on the double bond of the aldehyde group or the dicyanovinyl group of the anthracene-based probe molecule to generate addition reaction, then further elimination reaction is carried out to remove water or malononitrile to form a double bond, and the conversion from the probe to the product molecular structure corresponds to the change of the fluorescence color.
Drawings
FIG. 1 shows the detection effect of the aldehyde-anthracene-based probe and the dicyanoethylene-anthracene-based probe on phenylpropylamine in example 1 of the present invention;
FIG. 2 shows the detection effect of different concentrations of dicyanoethylene-anthracene-based probe molecules on p-propylamine in example 2 of the present invention;
FIG. 3 is a graph showing fluorescence changes before and after reaction of amphetamine in a series of concentrations detected by a dicyanoethylene-anthracene-based probe molecule in example 3 of the present invention, and a correlation between the fluorescence changes and the concentration of amphetamine;
FIG. 4 shows the detecting effect of dicyanoethylene-anthracene-based probe molecules in detecting amphetamine and other common amines in example 4 of the present invention;
FIG. 5 shows the detection effect of the dicyanoethylene-anthracene-based probe-sponge-based assay on captopril in example 5 of the present invention;
FIG. 6 is a graph showing the effect of response time of the dicyanoethylene-anthracene-based probe-sponge-based assay for captopril in example 6 of the present invention;
FIG. 7 is a graph showing the detection effect of the dicyanoethylene-anthracene-based probe-sponge-based assay for captopril and other common drugs in example 7 of the present invention.
Detailed Description
The present invention will be further illustrated by the following specific examples, but the present invention is not limited to these examples.
Example 1
Preparation of aldehyde-anthracene-based probe:
a. weighing 0.901mmol of 2-anthracene boric acid, 0.200g of 2-anthracene boric acid and 0.900mmol and 0.218g of 7-bromo-4-aldehyde benzo [ C ] [1,2,5] thiadiazole according to a molar ratio of 1:1, placing the weighed materials into a 100mL three-neck flask, adding 10mL of toluene, 5mL of pure water and 10mL of tert-butyl alcohol, controlling the reaction temperature to be 85 ℃ under the protection of nitrogen atmosphere, stirring, slowly adding 2.698mmol of sodium carbonate, 0.286g of sodium carbonate and 0.043mmol and 0.050g of tetrakis (triphenylphosphine) palladium as a catalyst, and reacting for 36 hours in a dark place;
b. after the reaction is finished, washing the reaction product to be neutral by using a dilute hydrochloric acid solution, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, carrying out suction filtration and spin drying to obtain an aldehyde-anthracene-based probe crude product, and sequentially carrying out methanol recrystallization and column chromatography purification to obtain an orange solid, namely the aldehyde-anthracene-based probe;
preparation of dicyanoethylene-anthracene-based probe:
c. b, placing the aldehyde-anthracene-based probe and malononitrile obtained in the step b into a 100mL three-neck flask according to a molar ratio of 1:1, adding 1mL of pyridine and 10mL of toluene, controlling the reaction temperature to be 60 ℃ and stirring under the protection of nitrogen atmosphere, and reacting for 24 hours in a dark place;
d. after the reaction is finished, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, performing suction filtration and spin drying to obtain a crude product of the dicyanoethylene-anthracene-based probe, and sequentially performing methanol recrystallization and column chromatography purification on the crude product to obtain a red solid as the dicyanoethylene-anthracene-based probe;
preparing a detection reagent:
e. respectively dissolving the aldehyde-anthracene-based probe obtained in the step b and the dicyanoethylene-anthracene-based probe obtained in the step d in tetrahydrofuran, and preparing an aldehyde-anthracene-based probe solution and a dicyanoethylene-anthracene-based probe solution with the concentration of 0.05-1mmol/L after ultrasonic dissolution to obtain two detection reagents for identifying amphetamine;
the detection effect of the aldehyde-anthracene-based probe molecule on the phenylpropylamine in the tetrahydrofuran solvent is as follows:
f. e, putting 450 mu L of the 0.05mmol/L aldehyde-anthracene-based probe solution obtained in the step e into a test tube, adding 50 mu L of amphetamine solution with the concentration of 5mmol/L, after full reaction, selecting the excitation wavelength to be 365nm, recording a fluorescence spectrum and taking a fluorescence picture; the detection effect of the aldehyde-anthracene-based probe molecule on the p-propylamine in the tetrahydrofuran solvent is shown in figure 1, under the irradiation of a 365nm ultraviolet lamp, the fluorescence color of the reagent is changed from orange to yellow, in addition, the fluorescence wavelength is determined by a fluorescence spectrometer to be 365nm, the fluorescence characteristic peak is shifted from 650nm blue to about 590nm, and the fluorescence change of the phenomenon is obvious.
The detection effect of dicyanoethylene-anthracene-based probe molecules on the phenylpropylamine in a tetrahydrofuran solvent is as follows:
g. e, putting 450 mu L of the 0.05mmol/L dicyanoethylene-anthracene-based probe solution obtained in the step e into a test tube, then adding 5mmol/L amphetamine solution, after full reaction, selecting the excitation wavelength to be 365nm, recording a fluorescence spectrum and taking a fluorescence picture; the detection effect of dicyanoethylene-anthracene-based probe molecules on the p-propylamine in the tetrahydrofuran solvent is shown in figure 1, under the irradiation of a 365nm ultraviolet lamp, the fluorescence color of a reagent is changed from red to yellow, in addition, the fluorescence wavelength is determined by a fluorescence spectrometer, the selected excitation wavelength is 365nm, the fluorescence characteristic peak is shifted from 735nm blue to about 590nm, and the fluorescence change of the phenomenon is obvious.
Example 2
The detection effect of dicyanoethylene-anthracene-based probe molecules with different concentrations on the phenylpropylamine is as follows:
preparing a detection reagent: dissolving the dicyanoethylene-anthracene-based probe prepared in the step d of the embodiment 1 in a tetrahydrofuran solution to prepare dicyanoethylene-anthracene-based probe solutions with the concentrations of 0.01, 0.05, 0.125, 0.25, 0.5 and 1mmol/L respectively, and then putting 450 mu L of dicyanoethylene-anthracene-based probe solution with the corresponding concentration in a test tube to obtain a detection reagent;
preparing an amphetamine standard solution: tetrahydrofuran is used as a solvent to prepare an amphetamine standard solution with the concentration of 5 mmol/L;
and (3) detection process: b, sucking 50 mu L of the amphetamine standard solution obtained in the step b, adding the amphetamine standard solution into the detection reagents with different probe concentrations obtained in the step a, after full reaction, selecting the excitation wavelength to be 365nm, recording the fluorescence spectrum and taking a fluorescence picture;
and (3) detection effect: the detection effect of the tetrahydrofuran solution of dicyanoethylene-anthracene-based probe molecules with different concentrations on the phenylpropylamine is shown in fig. 2. Under the irradiation of a 365nm ultraviolet lamp, the fluorescence colors of the reagents are changed into yellow after reaction; under the condition that the concentration of the probe is respectively 0.01, 0.05, 0.125, 0.25, 0.5 and 1mmol/L, the fluorescence change before and after the reaction of the amphetamine is detected by a reagent is obvious, and the detection of the cyclophanamine in the concentration range by the dicyanoethylene-anthracene-based probe is effective.
Example 3
Detecting a series of concentrations of amphetamine by using a dicyanoethylene-anthracene-based probe:
preparing a detection reagent: dissolving the dicyanoethylene-anthracene-based probe prepared in the step d of example 1 in a tetrahydrofuran solution to prepare a dicyanoethylene-anthracene-based probe solution with the concentration of 0.05mmol/L, and putting 450 mu L of the dicyanoethylene-anthracene-based probe solution in a test tube to obtain a detection reagent;
preparing an amphetamine standard solution: tetrahydrofuran is used as solvent to prepare amphetamine standard solution with the concentration of 0.2, 0.4, 0.6, 0.8, 1.0, 1.5, 2.0, 3.0, 4.0 and 5.0 mmol/L;
and (3) detection process: adding 50 mu L of prepared amphetamine standard solution into a detection reagent, after full reaction, selecting an excitation wavelength of 365nm, measuring a fluorescence spectrum, and making a correction curve according to the amphetamine content corresponding to the ratio of the fluorescence intensity at a product characteristic peak 590nm to a probe characteristic peak 735 nm;
and (3) detection effect: as shown in figure 3, the variation of the intensity ratio of the characteristic peak of the product after the reaction of detecting the amphetamine in the tetrahydrofuran solvent system and the characteristic peak of the probe shows a good linear relationship with the variation of the concentration of the amphetamine within the range of 20-500 mu mol/L, so the probe molecule can quantitatively detect the amphetamine molecule.
Example 4
Detecting the amphetamine and amine interferents thereof by using a dicyanoethylene-anthracene-based probe:
preparing a detection reagent: dissolving the dicyanoethylene-anthracene-based probe prepared in the step d of example 1 in tetrahydrofuran to prepare a dicyanoethylene-anthracene-based probe solution with the concentration of 0.05mmol/L, and putting 450 mu L of the dicyanoethylene-anthracene-based probe tetrahydrofuran solution with the concentration of 0.05mmol/L into a test tube to obtain a detection reagent;
preparing a solution of a substance to be detected: tetrahydrofuran is used as a solvent, and other common amines such as aniline, diphenylamine, triethylamine, dimethylaniline, sulfanilamide, ammonia water, L-glutamine, p-toluidine and triethanolamine are used as interference substances for detecting the amphetamine to prepare a solution with the corresponding concentration of 50 mmol/L;
and (3) detection process: adding 50 mu L of 50mmol/L common other amines or 5mmol/L amphetamine into the configured detection reagent, after full reaction, selecting the excitation wavelength to be 365nm, and recording a fluorescence spectrum and an optical photo;
and (3) detection effect: the detection effect of the dicyanoethylene-anthracene-based probe on detection of the amphetamine and the amine interferent thereof is shown in fig. 4, the color of the detection reagent is changed from dark red to yellow due to the addition of the amphetamine, the fluorescence characteristic peak is blue-shifted from 735nm to about 590nm, and other common amines have no obvious interference on detection, which indicates that the dicyanoethylene-anthracene-based probe molecule has good selectivity on the phenylpropylamine.
Example 5
The detection effect of the sponge-based dicyanoethylene-anthracene-based probe molecule for detecting the amphetamine methanol solution is as follows:
preparing a dicyanoethylene-anthracene-based probe composite sponge substrate: dissolving the dicyanoethylene-anthracene-based probe prepared in the step d of the embodiment 1 in a tetrahydrofuran solution to prepare a dicyanoethylene-anthracene-based probe solution with the concentration of 0.1mmol/L, then soaking a polyurethane sponge in the obtained dicyanoethylene-anthracene-based probe solution, taking out the polyurethane sponge after complete soaking, placing the polyurethane sponge in an oven for drying at the temperature of 40 ℃, and obtaining a sponge analysis card loaded with a solid dicyanoethylene-anthracene-based probe after the solvent is completely volatilized;
preparing an amphetamine standard solution: methanol is used as a solvent to prepare an amphetamine standard solution with the concentration of 5 mmol/L;
and (3) detection process: dropwise adding 20 mu L of prepared amphetamine standard solution on the obtained sponge analysis card, after full contact reaction, respectively irradiating with white light and 365nm ultraviolet light, observing colorimetric fluorescence effect and taking a picture;
and (3) detection effect: the detection effect of the sponge-supported dicyanoethylene-anthracene-based probe molecule for detecting the amphetamine solution is shown in fig. 5, the colorimetric effect is changed from orange to light yellow, the fluorescent color is changed from orange to green, and the colorimetric and fluorescent changes are obvious.
Example 6
Response time of sponge-based supported dicyanoethylene-anthracene-based probe molecule to phenylpropylamine
Preparing a dicyanoethylene-anthracene-based probe composite sponge substrate: dissolving the dicyanoethylene-anthracene-based probe prepared in the step d of the embodiment 1 in a tetrahydrofuran solution to prepare a dicyanoethylene-anthracene-based probe solution with the concentration of 0.1mmol/L, then soaking a polyurethane sponge in the obtained dicyanoethylene-anthracene-based probe solution, taking out the polyurethane sponge after complete soaking, placing the polyurethane sponge in an oven for drying at the temperature of 40 ℃, and obtaining a sponge analysis card loaded with a solid dicyanoethylene-anthracene-based probe after the solvent is completely volatilized;
preparing an amphetamine standard solution: preparing an amphetamine standard solution with the concentration of 5mmol/L by using methanol as a solvent;
and (3) detection process: dripping 20 mu L of prepared amphetamine standard solution on a sponge analysis card, irradiating by 365nm ultraviolet light, and respectively taking fluorescence pictures at 0, 30, 60, 120 and 180 s;
and (3) detection effect: the response time of the sponge-based supported dicyanoethylene-anthracene-based probe molecule to 5mmol/L amphetamine is shown in FIG. 6, the fluorescence color of the sponge-based supported dicyanoethylene-anthracene-based probe molecule changes from orange to green within 60s, and the response time is less than 60s.
Example 7
Sponge substrate-supported dicyanoethylene-anthracene-based probe molecule for detecting amphetamine and other common drugs
Preparing a dicyanoethylene-anthracene-based probe composite sponge substrate: dissolving the dicyanoethylene-anthracene-based probe prepared in the step d of the embodiment 1 in a tetrahydrofuran solution to prepare a dicyanoethylene-anthracene-based probe solution with the concentration of 0.1mmol/L, then soaking a polyurethane sponge in the obtained dicyanoethylene-anthracene-based probe solution, taking out the polyurethane sponge after complete soaking, placing the polyurethane sponge in an oven for drying at the temperature of 40 ℃, and obtaining a sponge analysis card loaded with a solid dicyanoethylene-anthracene-based probe after the solvent is completely volatilized;
preparing a solution of a substance to be detected: preparing interfering substance methanol solution with corresponding concentration of 1mg/mL and amphetamine methanol solution with methanol as solvent and other common drugs such as methamphetamine, cocaine, morphine, barbital, K powder, ecstasy, magical, opium or marijuana as interfering substances for amphetamine detection;
and (3) detection process: dropwise adding the obtained 20 mu L of 1mg/mL other common drugs and amphetamine on the configured sponge analysis card, after full reaction, irradiating by 365nm ultraviolet light to observe fluorescence change and take a fluorescence picture;
and (3) detection effect: specific recognition of the sponge-based supported dicyanoethylene-anthracene-based probe molecule on the phenylpropylamine is shown in fig. 7, when 20 mu L of 1mg/mL amphetamine methanol solution is dripped on the sponge-based analysis card, the fluorescence color of the analysis card changes from orange to green within 60s, and other drugs have no obvious response, which indicates that the dicyanoethylene-anthracene-based probe molecule has good selectivity on the phenylpropylamine and has the potential of field application.
Claims (1)
1. A method for detecting amphetamine in drugs based on an anthracene-based probe is characterized by comprising the following steps:
preparing a detection reagent:
a. weighing 2-anthracene boric acid and 7-bromo-4-aldehyde benzo [ C ] [1,2,5] thiadiazole according to a molar ratio of 1:1, placing the weighed materials into a three-neck flask of 100mL, adding 10mL toluene, 5mL pure water and 10mL tert-butyl alcohol, controlling the reaction temperature to be 85 ℃ under the protection of nitrogen atmosphere, stirring, slowly adding sodium carbonate and a catalyst tetrakis (triphenylphosphine) palladium, and reacting 36h in a dark place;
b. after the reaction is finished, washing the reaction product to be neutral by using a dilute hydrochloric acid solution, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, carrying out suction filtration and spin drying to obtain an aldehyde-anthracene-based probe crude product, and sequentially carrying out methanol recrystallization and column chromatography purification to obtain an orange solid, namely the aldehyde-anthracene-based probe;
c. placing the aldehyde-anthracene-based probe and malononitrile obtained in the step b into a three-neck flask of 100mL according to a molar ratio of 1:1, adding 1mL pyridine and 10mL toluene, controlling the reaction temperature to be 60 ℃ and stirring under the protection of nitrogen atmosphere, and reacting 24h in a dark place;
d. after the reaction is finished, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, carrying out suction filtration and spin drying to obtain a crude product of the dicyanoethylene-anthracene-based probe, and sequentially carrying out methanol recrystallization and column chromatography purification to obtain a red solid as the dicyanoethylene-anthracene-based probe;
e. respectively dissolving the aldehyde-anthracene-based probe obtained in the step b and the dicyanoethylene-anthracene-based probe obtained in the step d in tetrahydrofuran, and preparing an aldehyde-anthracene-based probe solution and a dicyanoethylene-anthracene-based probe solution with the concentration of 0.01-1mmol/L after ultrasonic dissolution to obtain two detection reagents for identifying amphetamine;
detection of amphetamine with aldehyde-anthracene-based probe:
f. e, putting 450 mu L of the aldehyde-anthracene-based probe solution obtained in the step e into a test tube, then adding 50 mu L of an amphetamine solution to be detected, after full reaction, recording a fluorescence spectrum and an optical photo under the excitation condition of 365nm ultraviolet light, and observing the signal change of a fluorescence characteristic emission peak before and after the reaction;
detecting the amphetamine by using a dicyanoethylene-anthracene-based probe:
g. e, putting 450 mu L of the dicyanoethylene-anthracene-based probe solution obtained in the step e into a test tube, then adding 50 mu L of an amphetamine solution to be detected, after full reaction, recording a fluorescence spectrum and an optical photo under the excitation condition of 365nm ultraviolet light, and observing the signal change of a fluorescence characteristic emission peak before and after the reaction;
or soaking the polyurethane sponge in 0.1mmol/L dicyanoethylene-anthracene-based probe solution, taking out the polyurethane sponge after complete soaking, drying the polyurethane sponge at the temperature of 40 ℃ in an oven, and obtaining the sponge analysis card loaded with the dicyanoethylene-anthracene-based probe after the solvent is completely volatilized; 20 mu L of the amphetamine solution to be detected is absorbed and dripped on a sponge analysis card loaded with a dicyanoethylene-anthracene-based probe, and the colorimetric and fluorescent changes are observed under the conditions of sunlight and 365nm illumination.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211650429.6A CN115855906A (en) | 2022-12-21 | 2022-12-21 | Method for detecting amphetamine in drugs based on anthracene-based probe |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211650429.6A CN115855906A (en) | 2022-12-21 | 2022-12-21 | Method for detecting amphetamine in drugs based on anthracene-based probe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115855906A true CN115855906A (en) | 2023-03-28 |
Family
ID=85653389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211650429.6A Pending CN115855906A (en) | 2022-12-21 | 2022-12-21 | Method for detecting amphetamine in drugs based on anthracene-based probe |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115855906A (en) |
-
2022
- 2022-12-21 CN CN202211650429.6A patent/CN115855906A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Shyamal et al. | Aggregation induced emission based “turn-off” fluorescent chemosensor for selective and swift sensing of mercury (II) ions in water | |
| CN108246271B (en) | Preparation method of molecularly imprinted polymer microspheres for detecting 2, 4, 6-trinitrophenol | |
| CN100360932C (en) | Reagent for detecting mercury ion in water and its preparation method | |
| Nakamura et al. | Fluorometric sensing of biogenic amines with aggregation‐induced emission‐active tetraphenylethenes | |
| Wang et al. | A naked-eye and ratiometric near-infrared probe for palladium via modulation of a π-conjugated system of cyanines | |
| Shang et al. | A high performance fluorescent arylamine sensor toward lung cancer sniffing | |
| Huang et al. | A novel anthracene-based receptor: highly sensitive fluorescent and colorimetric receptor for fluoride | |
| Yin et al. | A new aggregation-induced emission active red-emitting fluorescent sensor for ultrarapidly, selectively and sensitively detecting hydrazine and its multiple applications | |
| Fu et al. | Reversible and “fingerprint” fluorescence differentiation of organic amine vapours using a single conjugated polymer probe | |
| CN109879776A (en) | A kind of application of the sour cyanines derivative in water solubility side and its synthetic method and detection aldehyde compound | |
| Hu et al. | A rhodamine-based dual chemosensor for the naked-eye detection of Hg 2+ and enhancement of the fluorescence emission for Fe 3+ | |
| CN106518763B (en) | The fluorescence probe and its synthetic method of a kind of optional ratio's formula detection cyanide ion and application | |
| CN101672780B (en) | Analytical method for detecting trace mercury in aqueous medium based on the color change of fluorescence | |
| Zhang et al. | Highly efficient nerve agents fluorescent film probe based on organic/inorganic hybrid silica nanoparticles | |
| Peng et al. | Double-site-based a smart fluorescent sensor for logical detecting of sulphides and its imaging evaluation of living organisms | |
| CN106397319A (en) | Fluorescent probe for proportionally detecting hydrazine, method for synthesizing fluorescent probe and application thereof | |
| CN111808130B (en) | Fluorescent probe synthesis and application for detecting diethyl chlorophosphate | |
| CN113004256B (en) | Ratio type probe for detecting mercury ions and preparation method and application thereof | |
| CN114516836A (en) | Fluorescent probe material, preparation method thereof and method for detecting sulfide | |
| Kayani et al. | Ratiometric Lanthanide Metal‐Organic Frameworks (MOFs) for Smartphone‐Assisted Visual Detection of Food Contaminants and Water: A Review | |
| CN106317062B (en) | A kind of preparation and application for the Ratiometric fluorescent probe for determining cadmium ion | |
| CN109320537A (en) | A kind of soluble two-photon fluorescence probe and its preparation method and application of for flour and in vivo benzoyl peroxide detection | |
| CN109020999A (en) | A kind of preparation and application of two pyroles near-infrared pH fluorescence probe of the boron of fluorine containing piperidyl | |
| Khan | Synthesis and Applications of Fluorescent Chemosensors: A Review | |
| Karakuş et al. | Fluorescein based three-channel probe for the selective and sensitive detection of CO32− ions in an aqueous environment and real water samples |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |