CN108507993A - A kind of interior decorating molecule pipe is the method for chemical sensor detection forbidden drug - Google Patents
A kind of interior decorating molecule pipe is the method for chemical sensor detection forbidden drug Download PDFInfo
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- CN108507993A CN108507993A CN201810337992.5A CN201810337992A CN108507993A CN 108507993 A CN108507993 A CN 108507993A CN 201810337992 A CN201810337992 A CN 201810337992A CN 108507993 A CN108507993 A CN 108507993A
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- chemical sensor
- concentration
- forbidden drug
- component
- fluorescence intensity
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
Abstract
The present invention provides a kind of method that interior decorating molecule pipe detects forbidden drug for chemical sensor, the side is using interior decorating molecule pipe provided by the invention as chemical sensor, the chemical sensor and sample are mixed to get mixed solution, test the fluorescence intensity of the mixed solution.The method can be in aqueous phase system to four kinds of forbidden drugs, that is ephedrine, Xin Fulin, phenacetin and procaine is quick, simple and sensitive detection, the method is in competitive sports to having very important application prospect in anti-depressant detection, judicial domain.
Description
Technical field
The invention belongs to drug tests, it is that chemical sensor detects forbidden drug to be related to a kind of interior decorating molecule pipe
Method.
Background technology
The abuse of forbidden drug has become a very serious social concern.Ephedrine does not synthesize the original of methamphetamine still
Material is classified as prescription medicine by China, and is also the excitant of amphetamine, forbids sportsman to make by WORLD ANTI-DOPING AGENCY
With limiting in its urine no more than 10 μ g/mL.Although pungent forint is a kind of natural sympathomimetic amine stimulants, but
Also the detection project for being put into WORLD ANTI-DOPING AGENCY in 2018.Procaine and phenacetin because its analgesic effect and it is low at
Originally it is widely used in the dopant of cocaine, the cocaine containing dopant may result in even more serious after being abused
Adverse reaction.Therefore it is very heavy to having in anti-depressant detection, judicial domain in competitive sports that these compounds are detected
The application wanted.However now, Gas Chromatography-mass Spectrometry (GC/MS), liquid chromatography/mass spectrometry (LC/MS), LC/ are substantially utilized
MS/MS, the technical methods such as high performance liquid chromatography (HPLC) detect Xin Fulin, procaine, phenacetin and ephedrine, this
A little traditional methods are not only time-consuming and laborious but also cost is high, are not suitable for very much being applied to competitive sports and judicial domain.
The present invention in order to solve these problems, has invented decorating molecule pipe within one kind and having passed through fluorescence light as chemical sensor thus
The intuitive variation of spectrum, to achieve the purpose that these drugs of quick, easy and batch detection.
Invention content
For the technical problems in the prior art, a kind of interior decorating molecule pipe of present invention offer is that chemical sensor is examined
The method for surveying forbidden drug, the method can in aqueous phase system to four kinds of forbidden drugs, i.e., ephedrine, Xin Fulin, it is non-that
Western fourth and procaine is quick, simple and sensitive detection, the method in competitive sports to anti-depressant detection, judicial lead
There is very important application prospect in domain.
In order to achieve the above objectives, the present invention uses following technical scheme：
The present invention provides a kind of method of chemical sensor detection forbidden drug, and the method is：By Formulas I and/or Formula II
Shown compound is mixed to get mixed solution as chemical sensor, by the chemical sensor and sample, described in test
The fluorescence intensity of mixed solution；
Wherein, R CH2CO2 —·NH4 +。
As currently preferred technical solution, the forbidden drug includes Xin Fulin, procaine, phenacetin or fiber crops
In yellow alkali any one or at least two combination, the combination is typical but non-limiting examples have：Pungent forint and Proca
The combination of cause, the combination of procaine and phenacetin, the combination of Na Xiding and ephedrine, the combination of ephedrine and Xin Fulin or
The combination etc. of pungent forint, procaine, phenacetin and ephedrine.
The present invention is through many experiments, decorating molecule pipe and a variety of drug knots in two kinds shown in the Formulas I and/or Formula II that use
Conjunction is tested, filtered out Xin Fulin, procaine, phenacetin or ephedrine these four forbidden drugs can with Formulas I and/
Or Formula II compound represented combines, and generates fluorescence response.Show shown in Formulas I and/or Formula II that the present invention uses by test
Two kinds in decorating molecule pipe to the binding constants of Xin Fulin, procaine, phenacetin and ephedrine all 104M-1More than,
Maximum is binding constants of the compound shown in Formulas I to procaine, has nearly reached 106M-1。
In the present invention, the detection method contains only one of above-mentioned four kinds of forbidden drugs of one-component in the sample being tested
When, can be qualitative and quantitatively detect the forbidden drug in sample and its content.And when containing in tested sample, there are many above-mentioned
When four kinds of forbidden drugs, it only can qualitatively determine and contain forbidden drug in sample, and determine specific substance and its content needs and match
Other methods are closed to be tested.
For the tested sample of one of above-mentioned four kinds of forbidden drugs for containing only one-component, the present invention can provide detection quilt
The method of forbidden drug concentration, the described method comprises the following steps in test sample sheet：
(1) by etc. amount of substance chemical sensor concentration different from what is known one-component forbidden drug solution mix
Mixed solution is obtained, the fluorescence intensity of mixed solution is tested, and calculates one-component forbidden drug concentration and fluorescence intensity
Fit equation；
(2) step (1) under the same conditions, the chemical sensor and one-component forbidden drug solution to be measured are mixed
It closes, tests the fluorescence intensity of mixed solution, bring the fluorescence intensity into fit equation that step (1) obtains, you can obtain and wait for
Survey one-component forbidden drug concentration.
As currently preferred technical solution, the one-component forbidden drug of step (1) the known various concentration is molten
The number of samples of liquid is more than or equal to 3.
Preferably, a concentration of 0~80 μM of the one-component forbidden drug solution of step (1) the known various concentration,
Such as 0 μM, 10 μM, 15 μM, 20 μM, 25 μM, 30 μM, 35 μM, 40 μM, 45 μM, 50 μM, 55 μM, 60 μM, 65 μM, 70 μM, 75 μM or
80 μM etc., it is not limited to cited numerical value, other interior unrequited numerical value of the numberical range are equally applicable.
Preferably, a concentration of 10,15 μM of the one-component forbidden drug solution of step (1) the known various concentration,
20 μM, 25 μM, 30 μM, 40 μM, 50 μM and 80 μM.
As currently preferred technical solution, the test temperature of step (1) and step (2) is 10~40 DEG C, such as 10 DEG C,
15 DEG C, 20 DEG C, 25 DEG C, 30 DEG C, 35 DEG C or 40 DEG C etc., it is not limited to cited numerical value, in the numberical range, other are not
The numerical value enumerated is equally applicable, preferably 25 DEG C.
As currently preferred technical solution, chemical sensor is dense in step (1) and step (2) described mixed solution
Degree is 1 × 10-6~1 × 10-5M, such as 1 × 10-6M、2×10-6M、3×10-6M、4×10-6M、5×10-6M、6×10-6M、7×
10-6M、8×10-6M、9×10-6M or 1 × 10-5M etc., it is not limited to cited numerical value, in the numberical range, other are not
The numerical value enumerated is equally applicable, and preferably 5 × 10-6M。
In the present invention, in 25 DEG C and chemical sensor a concentration of 5 × 10-6Under conditions of M, by the method for step (1)
It can be found that forbidden drug in a certain range with fluorescence intensity journey linear relationship.
In 25 DEG C and chemical sensor a concentration of 5 × 10-6Under conditions of M, when chemical sensor is compound shown in Formulas I
When, the range of linearity of Xin Fulin is 0~50 μM, and the range of linearity of procaine is 0~30 μM, and the range of linearity of phenacetin is
0~30 μM, the range of linearity of ephedrine is 0~80 μM.
In 25 DEG C and chemical sensor a concentration of 5 × 10-6Under conditions of M, when chemical sensor is chemical combination shown in Formula II
When object, the range of linearity of procaine is 0~80 μM, and the range of linearity of phenacetin is 0~40 μM, the range of linearity of ephedrine
It is 0~80 μM.
Compared with prior art, the present invention at least has the advantages that：
The present invention provides a kind of method that interior decorating molecule pipe detects forbidden drug for chemical sensor, the method Chinese style
Compound shown in I is respectively 1.4,0.7,0.3 to the detectable limit (LOD) of Xin Fulin, procaine, phenacetin and ephedrine
With 0.5 μ g/mL, compound shown in Formula II is respectively 3.1 to the detectable limit (LOD) of procaine, phenacetin and ephedrine,
0.6 and 1.1 μ g/mL, wherein compound shown in Formulas I limit the detection limit of ephedrine far below WORLD ANTI-DOPING AGENCY
Sportsman's urine Ephedrine content no more than 10 μ g/mL standard, therefore the method in competitive sports to emerging
There is very important application prospect in the detection of agent, the judicial domain of putting forth energy.
Description of the drawings
Fig. 1 is the fitting a straight line figure of Xin Fulin concentration and the fluorescence intensity of compound shown in formula I that embodiment 1 obtains；
Fig. 2 is the fitting a straight line figure of procaine concentration and the fluorescence intensity of compound shown in formula I that embodiment 2 obtains；
Fig. 3 is the fitting a straight line figure of procaine concentration and the fluorescence intensity of compound shown in formula II that embodiment 3 obtains；
Fig. 4 is the fitting a straight line figure of phenacetin concentration and the fluorescence intensity of compound shown in formula I that embodiment 4 obtains；
Fig. 5 is the fitting a straight line figure of phenacetin concentration and the fluorescence intensity of compound shown in formula II that embodiment 5 obtains；
Fig. 6 is the fitting a straight line figure of Chinese ephedra alkali concentration and the fluorescence intensity of compound shown in formula I that embodiment 6 obtains；
Fig. 7 is the fitting a straight line figure of Chinese ephedra alkali concentration and the fluorescence intensity of compound shown in formula II that embodiment 7 obtains；
Fig. 8 is fluorescence spectra of the compound in nikethamidum aqueous solution shown in formula I；
Fig. 9 is fluorescence spectra of the compound in nikethamidum aqueous solution shown in formula II；
Figure 10 is fluorescence spectra of the compound in PHENYLEPHRINE HYDROCHLORIDE aqueous solution shown in formula I；
Figure 11 is fluorescence spectra of the compound in PHENYLEPHRINE HYDROCHLORIDE aqueous solution shown in formula II.
The present invention is described in more detail below.But following examples is only the simple example of the present invention, not generation
Table or limitation the scope of the present invention, protection scope of the present invention are subject to claims.
Specific implementation mode
Technical solution to further illustrate the present invention below with reference to the accompanying drawings and specific embodiments.
For the present invention is better described, it is easy to understand technical scheme of the present invention, of the invention is typical but non-limiting
Embodiment is as follows：
Embodiment 1
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas I-6M aqueous solution) is added in the version of 96 holes, then
The pungent folin solution for the various concentration that 50 μ L are prepared with simulation urine is sequentially added, the concentration of each sample ephedrine is respectively
0, it 15,20,25,30,40,50 and 80 μM, is detected with fluorescence reader, testing conditions are excitation wavelength 350nm, launch wavelength
403nm is repeated 12 times.Its result is illustrated in fig. 1 shown below.
It will be seen from figure 1 that detectable limit 1.4 μ g/mL of the interior decorating molecule pipe shown in formula I to Xin Fulin, the range of linearity
It is 0~50 μM.
Embodiment 2
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas I-6M aqueous solution) is added in the version of 96 holes, then
Sequentially add the liquor procainae hydrochloridi for the various concentration that 50 μ L are prepared with simulation urine, the concentration of each sample ephedrine
It respectively 0,15,20,25,30,40,50 and 80 μM, is detected with fluorescence reader, testing conditions are excitation wavelength 350nm, transmitting
Wavelength 403nm, is repeated 12 times.Its result is illustrated in fig. 2 shown below.
Figure it is seen that detectable limit 0.7 μ g/mL of the interior decorating molecule pipe shown in formula I to procaine hydrochloride, line
Ranging from 0~30 μM of property.
Embodiment 3
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas II-6M aqueous solution) is added in the version of 96 holes, so
Sequentially add the liquor procainae hydrochloridi for the various concentration that 50 μ L are prepared with simulation urine afterwards, each sample ephedrine it is dense
Degree is respectively 0,15,20,25,30,40,50 and 80 μM, is detected with fluorescence reader, and testing conditions are excitation wavelength 350nm, hair
The long 403nm of ejected wave, is repeated 12 times.Its result is illustrated in fig. 3 shown below.
From figure 3, it can be seen that detectable limit 3.1 μ g/mL of the interior decorating molecule pipe shown in formula II to procaine hydrochloride, line
Ranging from 0~80 μM of property.
Embodiment 4
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas I-6M aqueous solution) is added in the version of 96 holes, then
Sequentially add the phenacetin solution for the various concentration that 50 μ L are prepared with simulation urine, the concentration difference of each sample ephedrine
It is 0,15,20,25,30,40,50 and 80 μM, is detected with fluorescence reader, testing conditions is excitation wavelength 350nm, launch wavelength
403nm is repeated 12 times.Its result is illustrated in fig. 4 shown below.
From fig. 4, it can be seen that detectable limit 0.3 μ g/mL of the interior decorating molecule pipe shown in formula I to phenacetin, linear model
Enclose is 0~30 μM.
Embodiment 5
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas II-6M aqueous solution) is added in the version of 96 holes, so
The phenacetin solution for the various concentration that 50 μ L are prepared with simulation urine, the concentration point of each sample ephedrine are sequentially added afterwards
Wei not be 0,15,20,25,30,40,50 and 80 μM, it is detected with fluorescence reader, testing conditions are excitation wavelength 350nm, transmitted wave
Long 403nm, is repeated 12 times.Its result is illustrated in fig. 5 shown below.
From fig. 5, it can be seen that detectable limit 0.6 μ g/mL of the interior decorating molecule pipe shown in formula II to phenacetin, linear model
Enclose is 0~40 μM.
Embodiment 6
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas I-6M aqueous solution) is added in the version of 96 holes, then
The ephedrine solution for the various concentration that 50 μ L are prepared with simulation urine is sequentially added, the concentration of each sample ephedrine is respectively
0, it 15,20,25,30,40,50 and 80 μM, is detected with fluorescence reader, testing conditions are excitation wavelength 350nm, launch wavelength
403nm is repeated 12 times.Its result is illustrated in fig. 6 shown below.
From fig. 6, it can be seen that detectable limit 0.5 μ g/mL of the interior decorating molecule pipe shown in formula I to ephedrine, the range of linearity
It is 0~80 μM.
Embodiment 7
At 25 DEG C, by interior decorating molecule pipe (5 × 10 shown in 100 μ L formulas II-6M aqueous solution) is added in the version of 96 holes, so
The ephedrine hydrochloride solution for the various concentration that 50 μ L are prepared with simulation urine, the concentration of each sample ephedrine are sequentially added afterwards
It respectively 0,15,20,25,30,40,50 and 80 μM, is detected with fluorescence reader, testing conditions are excitation wavelength 350nm, transmitting
Wavelength 403nm, is repeated 12 times.Its result is illustrated in fig. 7 shown below.
From figure 7 it can be seen that detectable limit 1.1 μ g/mL of the interior decorating molecule pipe shown in formula II to ephedrine hydrochloride, linearly
Ranging from 0~80 μM.
Embodiment 8
At 25 DEG C, the nikethamidum (aqueous solution) of 2mM is added drop-wise to interior decorating molecule pipe (5 × 10 shown in formula I-6M)
It in aqueous solution, is detected with luminoscope, testing conditions are excitation wavelength 330nm, launch wavelength 403nm.The following Fig. 8 institutes of its result
Show.
From figure 8, it is seen that interior decorating molecule pipe shown in formula I responds nikethamidum unstressed configuration.
Embodiment 9
At 25 DEG C, the nikethamidum (aqueous solution) of 2mM is added drop-wise to interior decorating molecule pipe (5 × 10 shown in formula II-6M)
It in aqueous solution, is detected with luminoscope, testing conditions are excitation wavelength 330nm, launch wavelength 403nm.The following Fig. 9 institutes of its result
Show.
From fig. 9, it can be seen that interior decorating molecule pipe shown in formula II responds nikethamidum unstressed configuration.
Embodiment 10
At 25 DEG C, by the PHENYLEPHRINE HYDROCHLORIDE (aqueous solution) of 2mM be added drop-wise to interior decorating molecule pipe shown in formula I (5 ×
10-6M it in aqueous solution), is detected with luminoscope, testing conditions are excitation wavelength 330nm, launch wavelength 403nm.Its result is as follows
Shown in Figure 10.
From fig. 10 it can be seen that interior decorating molecule pipe shown in formula I responds PHENYLEPHRINE HYDROCHLORIDE unstressed configuration.
Embodiment 11
At 25 DEG C, the PHENYLEPHRINE HYDROCHLORIDE (aqueous solution) of 2mM is added drop-wise to interior decorating molecule pipe (5 shown in formula II
×10-6M it in aqueous solution), is detected with luminoscope, testing conditions are excitation wavelength 330nm, launch wavelength 403nm.Its result is such as
Shown in lower Figure 11.
It can be seen from figure 11 that interior decorating molecule pipe shown in formula II responds PHENYLEPHRINE HYDROCHLORIDE unstressed configuration.
Applicant states that the present invention illustrates the detailed construction feature of the present invention by above-described embodiment, but the present invention is simultaneously
It is not limited to above-mentioned detailed construction feature, that is, does not mean that the present invention has to rely on above-mentioned detailed construction feature and could implement.Institute
Belong to those skilled in the art it will be clearly understood that any improvement in the present invention, to the equivalence replacement of component selected by the present invention
And the increase of accessory, the selection etc. of concrete mode, it all falls within protection scope of the present invention and the open scope.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail can carry out a variety of simple variants to technical scheme of the present invention within the scope of the technical concept of the present invention, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can
The combination of energy no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Claims (6)
1. a kind of interior decorating molecule pipe is the method that chemical sensor detects forbidden drug, which is characterized in that the method is：It will
Compound shown in Formulas I and/or Formula II be mixed to get with sample as chemical sensor, by the chemical sensor mix it is molten
Liquid tests the fluorescence intensity of the mixed solution；
Wherein, R CH2CO2 -·NH4 +。
2. according to the method described in claim 1, it is characterized in that, the forbidden drug include Xin Fulin, procaine, it is non-that
In western fourth or ephedrine any one or at least two combination.
3. a kind of side of the chemical sensor detection one-component forbidden drug concentration in 2 the method using claims 1 or 2
Method, which is characterized in that the described method comprises the following steps：
(1) by etc. the one-component forbidden drug solution of chemical sensor concentration different from what is known of amount of substance be mixed to get
Mixed solution, tests the fluorescence intensity of mixed solution, and makes the fitting side of one-component forbidden drug concentration and fluorescence intensity
Journey；
(2) step (1) under the same conditions, the chemical sensor is mixed with one-component forbidden drug solution to be measured,
The fluorescence intensity for testing mixed solution, brings the fluorescence intensity into fit equation that step (1) obtains, you can obtain list to be measured
One component forbidden drug concentration.
4. according to the method described in claim 3, it is characterized in that, the one-component of step (1) the known various concentration is disobeyed
The number of samples for prohibiting drug solution is more than or equal to 3；
Preferably, a concentration of 0~80 μM of the one-component forbidden drug solution of step (1) the known various concentration；
Preferably, the one-component forbidden drug solution of step (1) the known various concentration a concentration of 10,15,20,25,
30,40,50 and 80 μM.
5. method according to claim 3 or 4, which is characterized in that the test temperature of step (1) and step (2) be 10~
40℃。
6. to go 3-5 any one of them methods according to right, which is characterized in that step (1) and step (2) described mixed solution
A concentration of the 1 × 10 of middle chemical sensor-6~1 × 10-5M, preferably 5 × 10-6M。
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| CN201810337992.5A CN108507993B (en) | 2018-04-16 | 2018-04-16 | Method for detecting forbidden drugs by taking internal modification molecular tube as chemical sensor |
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| CN201810337992.5A CN108507993B (en) | 2018-04-16 | 2018-04-16 | Method for detecting forbidden drugs by taking internal modification molecular tube as chemical sensor |
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| CN109705131A (en) * | 2019-01-23 | 2019-05-03 | 南方科技大学 | A kind of macrocycle molecule and its preparation method and application |
| CN113845486A (en) * | 2021-08-26 | 2021-12-28 | 南方科技大学 | Anthracene-based macrocyclic molecules, and preparation method and application thereof |
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| CN109705131A (en) * | 2019-01-23 | 2019-05-03 | 南方科技大学 | A kind of macrocycle molecule and its preparation method and application |
| CN113845486A (en) * | 2021-08-26 | 2021-12-28 | 南方科技大学 | Anthracene-based macrocyclic molecules, and preparation method and application thereof |
| CN113845486B (en) * | 2021-08-26 | 2023-09-26 | 南方科技大学 | Anthracene-based macrocyclic molecule, and preparation method and application thereof |
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| CN108507993B (en) | 2022-03-25 |
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