CN109115749A - A kind of Broadspectrum specificity molecularly imprinted polymer, chemical luminescence reagent kit and the detection method and application of quinolone drugs - Google Patents
A kind of Broadspectrum specificity molecularly imprinted polymer, chemical luminescence reagent kit and the detection method and application of quinolone drugs Download PDFInfo
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- CN109115749A CN109115749A CN201810912456.3A CN201810912456A CN109115749A CN 109115749 A CN109115749 A CN 109115749A CN 201810912456 A CN201810912456 A CN 201810912456A CN 109115749 A CN109115749 A CN 109115749A
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- molecularly imprinted
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/76—Chemiluminescence; Bioluminescence
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Abstract
The invention discloses a kind of Broadspectrum specificity molecularly imprinted polymers of quinolone drugs, and using it as recognition component chemical luminescence reagent kit, detection method and application.For the molecularly imprinted polymer with pipemidic acid for false molecular template, the Broadspectrum specificity molecularly imprinted polymer of synthesis can identify 8 kinds of quinolone drugs.The chemical luminescence reagent kit prepared based on the molecularly imprinted polymer can carry out multi-residue determination to this 8 kinds of quinolone drugs in meat tissue, and reusable, improve detection sensitivity, shorten detection time, reduce testing cost.
Description
Technical field
The present invention relates to animal food safety fields, and in particular to a kind of molecule that can capture 8 kinds of quinolone drugs
The detection method and application of imprinted polymer, the chemical luminescence reagent kit thus prepared and the kit.
Background technique
Quinolone drugs is a kind of chemical synthesis antibacterials, and such drug toxicity is low, has a broad antifungal spectrum, antibacterial activity
By force, it is widely used in the treatment of animals and humans various bacterial disease.Common kind has Enrofloxacin, sarafloxacin, cyclopropyl husky
Star, Lomefloxacin, Ofloxacin, pefloxacin, single promise sand star, Marbofloxacin.As quinolone drugs is supported in food animal
A large amount of uses during growing, they in animal derived food caused by residue problem attract extensive attention.Du-6859a
The residual of object is likely to result in long-term a small amount of intake of consumer, causes the adverse reactions such as blood disease, osteoporosis, allergy, more
For the serious is the drug resistances that can induce humanized pathogenic bacteria.Therefore, it is necessary to pay attention to such drug in animal derived food
Residue problem.USA and EU all defines the maximum residue limit of such drug, and the Ministry of Agriculture has also issued fluorine quinoline promise
The maximum residue limit of ketone drug.
Currently, there is many methods that can detect to the residual of quinolone drugs, wherein immunoassay is simple, square
Just, the screening that can be used for batch samples, it is widely used in testing agency of base.But core reagent-antibody of immunoassay
The immunoassay or commercialization immunologic function test reagent for needing 4-6 months production cycles, and being established using antibody as recognition component
Box is disposable.Therefore, detection method/product gesture having the advantages that immunoassay, can be recycled is developed to exist
It must go.
Molecularly imprinted polymer is a kind of chemical synthesis material, can be formed have to specific objective object in the synthesis process
There is the three-dimensional lumen of specific recognition capability, therefore, referred to as " plastics antibody ".Moreover, the molecularly imprinted polymer preparation phase is short
It (1-2 weeks), at low cost, repeatable is recycled.Chemoluminescence method is that one kind is easy to operate, analysis speed fast (10-30 seconds)
Detection method, remolding sensitivity conventional immunological assays are higher, and agents useful for same is chemical reagent, not by factors such as temperature, times
It influences.Currently, there are a small number of documents to use the drug original shape of quinolone drugs for molecular template both at home and abroad, corresponding molecule is synthesized
Imprinted polymer is as recognition component for establishing chemiluminescence detecting method.But these methods are all made of double pump flow injection mould
Formula, operation sequence is complicated, not can be carried out batch screening, i.e., can only singly be detected to multiple samples.Secondly, having reported
The method in road can only detect a certain quinolone drugs.In addition, the sensitivity of these methods can not be to the quinolones of trace
Medicament residue is detected.
Therefore, the advantages of molecularly imprinted polymer, immunoassay, chemoluminescence method three, is combined, with molecular engram
Polymer is the chemoluminescence method that recognition component is established on common microwell plate or develops kit then have analysis speed
Fastly, easy to operate, high sensitivity can be recycled, be suitable for the characteristics of batch sample screening.But up to the present, both at home and abroad
Not for the correlative study report of the chemoluminescence method or kit based on molecularly imprinted polymer of quinolone drugs.
Summary of the invention
It is an object of the present invention to provide a kind of molecularly imprinted polymers of the Broadspectrum specificity of quinolone drugs, should
Molecularly imprinted polymer can capture a variety of quinolone drugs, and can be directly used for the inspection of chemiluminometry
It surveys.
To achieve the goals above, the present invention adopts the following technical scheme that:
A kind of molecularly imprinted polymer of the Broadspectrum specificity of quinolone drugs, it is characterised in that it prepares by the following method, with
Lower raw material presses the meter of substance:
(a) 1 part of false molecular template pipemidic acid, 5 ~ 7 parts of function monomer methacrylic acids, 20 ~ 30 parts of initiator azo two is different
Butyronitrile and 20 ~ 30 parts of crosslinking agent ethylene glycol dimethacrylate are placed in solvent, and 60 ~ 70 DEG C are reacted 10 ~ 12 hours, are obtained
To solid particulate matter；
(b) solid particulate matter is placed in Soxhlet extractor, with extracting solution continuous backflow 12 ~ 24 hours, by the false mould
Plate molecule pipemidic acid extracts；
(c) by after the solid particulate matter drying after step (b) reaction, the molecular engram of the Broadspectrum specificity of quinolone drugs is obtained
Polymer.
Preferably, solvent used in the step (a) is chloroform, extracting solution used in step (b) be methanol with
The mixed solution of acetic acid, and the volume ratio of methanol and acetic acid is 9:0.5 ~ 2.
It is a further object to provide a kind of chemiluminescence examinations of the Broadspectrum specificity of quinolone drugs detection
Agent box, the kit can accurately detect a variety of quinolone drugs, and it is convenient to operate, as a result reliably.For this purpose, of the invention
It adopts the following technical scheme that:
A kind of chemical luminescence reagent kit of the Broadspectrum specificity detection of quinolone drugs, the chemical luminescence reagent kit is with aforementioned point
Sub- imprinted polymer is that identification agent is with bis- (2,4,6- trichlorophenyl) oxalates and hydrogen peroxide using imidazoles as catalyst
Chemical illuminating reagent according to luminous intensity and testing concentration there is proportionate relationship to make detection to testing concentration.
The present invention also provides the detection methods using above-mentioned chemical luminescence reagent kit to quinolone drugs, including walk as follows
It is rapid:
(a) above-mentioned molecularly imprinted polymer is suspended in weight percent is then to be added in 0.3 ~ 2% poly-vinyl alcohol solution
Into the aperture of opaque polystyrene titer plates, place 1 ~ 2 hour；
(b) quinolone drugs to be detected or sample extracting solution are added in the aperture of the polystyrene titer plates, room
Temperature is placed 5 ~ 50 minutes；
(c) aperture of the polystyrene titer plates is washed, removes impurity and without captured quinolone drugs；
(d) will be bis- (2,4,6- trichlorophenyl) oxalate, imidazoles and hydrogen peroxide be added to the small of the polystyrene titer plates
The polystyrene titer plates are placed in Chemiluminescence Apparatus or multi-function microplate reader by Kong Zhong, read the values of chemiluminescence of each aperture.
Preferably, it in the step (c), is washed with aperture of the ethyl alcohol to the polystyrene titer plates.
The present invention provides a kind of above-mentioned chemical luminescence reagent kit in detection Enrofloxacin, sarafloxacin, Ciprofloxacin, Lome
The application of Sha Xing, Ofloxacin, pefloxacin, single promise sand star, Marbofloxacin field.
The beneficial effects of the present invention are: being false molecular template with pipemidic acid, the wide spectrum for having synthesized quinolone drugs is special
Property molecularly imprinted polymer, can identify 8 common kinds of such drug simultaneously: Enrofloxacin, sarafloxacin, cyclopropyl are husky
Star, Lomefloxacin, Ofloxacin, pefloxacin, single promise sand star, Marbofloxacin.Using the molecularly imprinted polymer as recognition component
The chemical luminescence reagent kit of preparation more to the progress of 8 kinds of quinolone drugs in animal muscle can remain, is quick, sensitive inspection
It surveys, to realize that the field quick detection of quinolones medicament relict is laid a good foundation, can ensure that animality is eaten in a wider context
Product safety.In addition, since the tolerance that molecularly imprinted polymer changes chemical/physical condition is strong, it is provided by the invention
Chemical luminescence reagent kit may be reused, and greatly reduce testing cost, reduce resource waste, and it is green to meet current social
The trend of color sustainable development.
Detailed description of the invention
Fig. 1 be control without molecular template when the electron-microscope scanning picture of polymer that synthesizes；
Fig. 2 is the electron-microscope scanning picture of the molecularly imprinted polymer of this patent preparation；
Fig. 3 is capture effect of the molecularly imprinted polymer to 7 kinds of quinolone drugs of this patent preparation；
Fig. 4 is the concentration of Ciprofloxacin detection and the standard curve of OD value.
Specific embodiment
Below by specific embodiment, the present invention will be further described, presses the meter of substance below:
1 molecularly imprinted polymer synthesis example 1 of embodiment
(a) by 1 part of false molecular template pipemidic acid, 5 parts of function monomer methacrylic acids, 20 parts of initiator azodiisobutyronitrile and
20 parts of crosslinking agent ethylene glycol dimethacrylate is placed in chloroform solvent, and 60 DEG C are reacted 12 hours, obtains solid particle
Object；
(b) solid particulate matter is placed in Soxhlet extractor, with methanol and acetic acid (9:1, V/V) extracting solution continuous backflow 12
Hour, the false template molecule pipemidic acid of trace is extracted；
(c) by after the solid particulate matter drying after step (b) reaction, the molecular engram of the Broadspectrum specificity of quinolone drugs is obtained
Polymer.
2 molecularly imprinted polymer synthesis example 2 of embodiment
(a) by 1 part of false molecular template pipemidic acid, 7 parts of function monomer methacrylic acids, 30 parts of initiator azodiisobutyronitrile and
30 parts of crosslinking agent ethylene glycol dimethacrylate is placed in chloroform solvent, and 70 DEG C are reacted 10 hours, obtains solid particle
Object；
(b) solid particulate matter is placed in Soxhlet extractor, with methanol and acetic acid (9:2, V/V) extracting solution continuous backflow 24
Hour, the false template molecule pipemidic acid of trace is extracted；
(c) by after the solid particulate matter drying after step (b) reaction, the molecular engram of the Broadspectrum specificity of quinolone drugs is obtained
Polymer.
3 molecularly imprinted polymer synthesis example 3 of embodiment
(a) by 1 part of false molecular template pipemidic acid, 6 parts of function monomer methacrylic acids, 25 parts of initiator azodiisobutyronitrile and
25 parts of crosslinking agent ethylene glycol dimethacrylate is placed in chloroform solvent, and 65 DEG C are reacted 11 hours, obtains solid particulate matter；
(b) solid particulate matter is placed in Soxhlet extractor, with methanol and acetic acid (9:0.5, V/V) extracting solution continuous backflow
18 hours, the false template molecule pipemidic acid of trace is extracted；
(c) by after the solid particulate matter drying after step (b) reaction, the molecular engram for obtaining the Broadspectrum specificity of quinolone medicine is poly-
Close object.
The electron microscope photo scanning of molecularly imprinted polymer prepared by this example is as shown in Fig. 2, its surface is more as seen from Figure 2
Hole can identify quinolone drugs for the cavity that template molecule trace is formed；It is distinguished with this, if do not used
Above-mentioned vacation molecular template, the electron microscope photo scanning of the polymer synthesized is as shown in Figure 1, its surfacing, smooth, without hole
Gap cannot identify quinolone drugs.The Electronic Speculum of molecularly imprinted polymer prepared by embodiment 1 and embodiment 2 is swept
It is similar with Fig. 2 situation in this example to retouch photo.
Capture validity check of the above-mentioned molecularly imprinted polymer of embodiment 4 to seven kinds of quinolone drugs
The molecularly imprinted polymer particle that quinolone drugs is directed to prepared by embodiment 3 is placed in empty solid phase as filler
In extraction column, by 7 kinds of drugs (1=Ofloxacin, 2=Ciprofloxacin, 3=pefloxacin, 4=Lomefloxacin, 5=En Nuosha
Star, 6=sarafloxacin, 7=mono- promise sand star) standard items mixed solution be added on the column, liquid flows out naturally.Then first is used
The medicament elution that alcohol/acetic acid solution (9:1, V/V) will be adsorbed, eluent are detected with ultra-performance liquid chromatography.Chromatogram (figure
3) show the ability that the polymer there are the above-mentioned 7 kinds of drugs of specific adsorption.Also there are similar results to the experiment of Marbofloxacin.It attempts
Similar experiment is carried out with the non-quinolone drugs such as amantadine, sulfamido, beta-stimulants, tetracycline, chloramphenicol, phenthazine,
It was found that this molecular imprinting polymer does not adsorb these drugs.Therefore, which is made in the aperture of microwell plate
For recognition component, the kit being assembled into can adsorb above-mentioned 8 kinds of quinolone drugs.It, can be quick by luminesceence analysis
Screen in sample to be tested whether there are also at least one of above-mentioned 8 kinds of quinolone drugs.
The composition of 5 chemical luminescence reagent kit of embodiment
Chemical luminescence reagent kit includes following composition:
Molecularly imprinted polymer prepared by embodiment 1,2 or 3 can capture quinolone drugs as identification agent, be
Detection provides basis；
Bis- (2,4,6- trichlorophenyl) oxalates and hydrogen peroxide, both as chemical illuminating reagent；
Imidazoles plays catalytic action to reaction, it is made quickly to shine as catalyst；
After shining, according to luminous intensity and testing concentration there is proportional relationship to do to testing concentration using Chemiluminescence Apparatus
It detects out.
Embodiment 6 utilizes the detection method of mentioned reagent box quinolone drugs
Detection method is as follows:
(a) previous molecular imprinted polymer is suspended in weight percent is to be then added in 0.3 ~ 2% poly-vinyl alcohol solution
In the aperture of polystyrene titer plates, place 1 ~ 2 hour；
(b) quinolone drugs to be detected or sample extracting solution are added in the aperture of polystyrene titer plates, room temperature is put
It sets 5 ~ 50 minutes；
(c) aperture of the polystyrene titer plates is washed, removes impurity and without captured quinolone drugs；
(d) will be bis- (2,4,6- trichlorophenyl) oxalate, imidazoles and hydrogen peroxide be added sequentially to the polystyrene titer plates
Aperture in, which is placed in Chemiluminescence Apparatus or multi-function microplate reader, read each aperture chemistry hair
Light value.
(e) according to whether there is luminous value, judge whether containing 8 kinds of quinolone drugs used in embodiment 4 at least
It is a kind of.
After above-mentioned molecularly imprinted polymer-chemical luminescence reagent kit is washed with methanol/acetic acid, reusable 5 times.
This example illustrates that this kit disposably can quickly screen in sample to be tested whether contain above-mentioned quinolone drugs
It is one or more, for not luminescence phenomenon sample explanation be free of above-mentioned 8 kinds of quinolone drugs, for there is luminescence phenomenon
Sample, can be analyzed again by specific type and content of the high performance liquid chromatography to contained quinolone drugs.Cause
This, this kit greatly improves the screening efficiency to sample.
The detection effect of 7 chemical luminescence reagent kit of embodiment
By taking Ciprofloxacin as an example, by drug standards with sample extracting solution carry out series of concentrations dilution (0.01,0.05,0.1,
0.5,1.0,5.0,10,50 ng/mL), it is then respectively added to be surrounded by the different apertures of molecularly imprinted polymer, by above-mentioned
Method is tested.The result shows that being in good linear relationship between drug concentration and values of chemiluminescence, illustrate to use the kit
When, the concentration of drug can be calculated by the OD value of measurement, accuracy with higher, experimental result such as Fig. 4
It is shown.
Above-described embodiment is the explanation conceived to the utility model and realized, is not intended to limit it, in present inventive concept
Under, without the technical solution that substantially converts still in protection scope.
Claims (6)
1. a kind of molecularly imprinted polymer of the Broadspectrum specificity of quinolone drugs, it is characterised in that it prepares by the following method,
Following raw material presses the meter of substance:
(a) 1 part of false molecular template pipemidic acid, 5 ~ 7 parts of function monomer methacrylic acids, 20 ~ 30 parts of initiator azo two is different
Butyronitrile and 20 ~ 30 parts of crosslinking agent ethylene glycol dimethacrylate are placed in solvent, and 60 ~ 70 DEG C are reacted 10 ~ 12 hours, are obtained
To solid particulate matter；
(b) solid particulate matter is placed in Soxhlet extractor, with extracting solution continuous backflow 12 ~ 24 hours, by the false mould
Plate molecule pipemidic acid extracts；
(c) by after the solid particulate matter drying after step (b) reaction, the molecular engram of the Broadspectrum specificity of quinolone drugs is obtained
Polymer.
2. molecularly imprinted polymer as described in claim 1, it is characterised in that: solvent used in the step (a) is
Chloroform, extracting solution used in step (b) is the mixed solution of methanol and acetic acid, and the volume ratio of methanol and acetic acid is 9:
0.5~2。
3. the chemical luminescence reagent kit that a kind of Broadspectrum specificity of quinolone drugs detects, it is characterised in that the chemiluminescence
Kit is using molecularly imprinted polymer of any of claims 1 or 2 as identification agent, using imidazoles as catalyst, with bis- (2,4,6-
Trichlorophenyl) oxalate and hydrogen peroxide be chemical illuminating reagent, proportionate relationship is had according to luminous intensity and testing concentration
Detection is made to testing concentration.
4. using chemical luminescence reagent kit as claimed in claim 3 to the detection method of quinolone drugs, it is characterised in that packet
Include following steps:
(a) molecularly imprinted polymer of any of claims 1 or 2 is suspended in weight percent is 0.3 ~ 2% poly-vinyl alcohol solution
In, it is then added in the aperture of opaque polystyrene titer plates, places 1 ~ 2 hour；
(b) quinolone medicine to be detected or sample extracting solution are added in the aperture of the polystyrene titer plates, room temperature
It places 5 ~ 50 minutes；
(c) aperture of the polystyrene titer plates is washed, removes impurity and without captured quinolone drugs；
(d) will be bis- (2,4,6- trichlorophenyl) oxalate, imidazoles and hydrogen peroxide be added to the small of the polystyrene titer plates
The polystyrene titer plates are placed in Chemiluminescence Apparatus or multi-function microplate reader by Kong Zhong, read the values of chemiluminescence of each aperture.
5. method as claimed in claim 4, which is characterized in that in the step (c), titrated with ethyl alcohol to the polystyrene
The aperture of plate is washed.
6. chemical luminescence reagent kit as claimed in claim 3 is husky in detection Enrofloxacin, sarafloxacin, Ciprofloxacin, Lome
The application of star, Ofloxacin, pefloxacin, single promise sand star, Marbofloxacin field.
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| CN201810912456.3A CN109115749A (en) | 2018-08-12 | 2018-08-12 | A kind of Broadspectrum specificity molecularly imprinted polymer, chemical luminescence reagent kit and the detection method and application of quinolone drugs |
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Cited By (2)
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| CN112362797A (en) * | 2020-10-26 | 2021-02-12 | 浙江国正检测技术有限公司 | Method for detecting quinolone drugs in feed |
| CN114259991A (en) * | 2021-12-21 | 2022-04-01 | 河南省商业科学研究所有限责任公司 | Molecular imprinting material for efficiently adsorbing and removing fluoroquinolone antibiotics and preparation method and application thereof |
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| CN114259991B (en) * | 2021-12-21 | 2022-12-09 | 河南省商业科学研究所有限责任公司 | Molecular imprinting material for efficiently adsorbing and removing fluoroquinolone antibiotics and preparation method and application thereof |
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Application publication date: 20190101 |