CN107084974A - Application of the DNA Mimetic Peroxidases in 2 hydroxyphenyl fluorene chemiluminescence detections - Google Patents

Application of the DNA Mimetic Peroxidases in 2 hydroxyphenyl fluorene chemiluminescence detections Download PDF

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CN107084974A
CN107084974A CN201710225593.5A CN201710225593A CN107084974A CN 107084974 A CN107084974 A CN 107084974A CN 201710225593 A CN201710225593 A CN 201710225593A CN 107084974 A CN107084974 A CN 107084974A
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dna
hydroxyphenyl
detection
fluorenes
mixed
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CN107084974B (en
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梁刚
李安
满燕
靳欣欣
潘立刚
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Beijing Academy of Agriculture and Forestry Sciences
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BEIJING AGRICULTURAL QUALITY STANDARDS AND TESTING TECHNOLOGY RESEARCH CENTER
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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
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/76—Chemiluminescence; Bioluminescence
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00—Sampling; Preparing specimens for investigation
    • G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/38—Diluting, dispersing or mixing samples

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  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Health & Medical Sciences (AREA)
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  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
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Abstract

The invention belongs to detection technique field, propose that the DNA in application of the DNA Mimetic Peroxidases in the chemiluminescence detection of 2 hydroxyphenyl fluorenes, the DNA Mimetic Peroxidases has G tetrad nucleotide sequences.The present invention also proposes a kind of 2 hydroxyphenyl fluorene chemical luminescence detection methods of application DNA Mimetic Peroxidases.The present invention proposes application of the DNA Mimetic Peroxidases in the chemiluminescence detection of 2 hydroxyphenyl fluorenes, foundation, the DNA bioanalytical methods for improving and having developed 2 hydroxyphenyl fluorene pollutants, may be either that Environmental Health risk assessment and employment security are assessed and provide reference, a kind of new highly sensitive, inexpensive detection method is developed simultaneously, to improving the significant and preferable application value of existing detection technique means.

Description

Application of the DNA Mimetic Peroxidases in 2- hydroxyphenyl fluorene chemiluminescence detections
Technical field
The invention belongs to detection technique field, and in particular to a kind of chemical luminescence detection method for 2- hydroxyphenyl fluorenes.
Background technology
Fluorenes is widely used in medicine, such as anodyne, sedative, antihypertensive as a kind of important industrial chemicals Deng, the synthesis of agricultural chemicals, herbicide, dyestuff, lucite etc., this is also the important channel of human body fluorenes exposure.Into in human body Fluorenes can be metabolized by internal enzyme, can be also degraded by microorganisms in environmental system, and its main catabolite is 2- hydroxyphenyl fluorenes.Grind Study carefully and show, cause it same due to effect hydroxy activated in 2- hydroxyphenyl fluorenes with metabolism toxicity.In addition, 2- hydroxyls in human body The level of fluorenes and the exposure level of fluorenes have positive correlation, thus 2- hydroxyphenyl fluorenes also be typically one kind be widely used in assess fluorenes it is sudden and violent The flat biomarker of dew, can provide data supporting for Human Health Risk early warning and employment security assessment etc..Therefore, scientific research Worker needs urgently to develop a kind of quick, simple, sensitive 2- hydroxyphenyl fluorenes detection method, with important researching value.
It is presently used for detecting that the method for 2- hydroxyphenyl fluorenes mainly uses large-scale instrument and equipment, such as liquid chromatography, liquid phase Chromatograph-mass spectrometer coupling method, gas chromatography-mass spectrometry etc..But these traditional analysis methods still have several drawbacks it Place, such as needs to handle sample before chromatography is carried out, and takes longer.In addition, expensive tester and in test When need trained professional and technical personnel, instrument to place when the conditions such as place also limit instrumental method outer analysis sample out of office Using.In this case, the detection method for developing simple, cheap, efficient 2- hydroxyphenyl fluorenes is imperative.DNA bio-sensings Utensil have it is quick, simple, cheap, can in-site detecting the features such as, on this basis, Liang seminars devise DNA enzymatic and repaiied first Adorn electrochemica biological sensor[1], based on the effect of enzymatic hydrogen peroxide oxidation 2- hydroxyphenyl fluorenes, its indissoluble thing generated is deposited on Electrode surface, causes film resistance to increase, and the detection to 2- hydroxyphenyl fluorenes is successfully realized by analysis means of Electrode with Electrochemical Impedance Spectroscopy.So And, some shortcomings part is still suffered from using electrochemical DNA bio-sensing method detection 2- hydroxyphenyl fluorenes, such as needs first to prepare before detection DNA modification electrode, the modification makes detection cycle elongated, greatly reduces the efficiency of analysis detection；While electrode modification film The performance of material, the stability of modified membrane can also influence the accuracy of measurement result；Difference, electricity between electrode modification film batch Difference between pole etc. can produce influence to measurement result.The method for detecting 2- hydroxyphenyl fluorenes is thus analytical chemistry and environmental recovery bonds Difficult point research topic, seeking a kind of method of quicker, simple, accurate, sensitive, efficient detection 2- hydroxyphenyl fluorenes has Important meaning, also there is very big challenge.
Chemoluminescence method has the advantages that the sample preparation cycle is short, detection is quick, amount of samples is few, response is strong, is one Plant more satisfactory fast detecting method.With going deep into for recognizing DNA, researcher finds G- tetrad DNA and hemin molecules G- tetrads/hemin compounds can be formed with reference to after, the compound has the catalytic activity of class peroxide mould enzyme, claimed Be class Mimetic Peroxidase DNA enzymatic, the DNA enzymatic has extremely strong catalytic activity, can be catalyzed hydrogen peroxide oxidation luminol Produce chemiluminescence[2], based on this, the DNA enzymatic has been widely used in bio-sensing analysis field.But up to the present, still There is not the research for carrying out optical detection to 2- hydroxyphenyl fluorenes pollutant based on peroxide mould enzyme dna enzyme to report.
Bibliography
1.Liang G.,Liu,X.H.,2015.G-quadruplex based impedimetric2- hydroxyfluorene biosensor using hemin as a peroxidase enzyme mimic.Microchim.Acta 182(13),2233-2240.
2.Kosman,J.,Juskowiak,B.,2011.Peroxidase-mimicking DNAzymes for biosensing applications:A review.Anal.Chim.Acta 707,7-17.
The content of the invention
For the weak point of this area, it is an object of the invention to propose DNA Mimetic Peroxidases in 2- hydroxyphenyl fluorenes Chemiluminescence detection in application.
Second object of the present invention is to propose a kind of 2- hydroxyphenyl fluorenes chemiluminescence inspection of application DNA Mimetic Peroxidases Survey method.
The technical scheme for realizing above-mentioned purpose of the present invention is：
Application of the DNA Mimetic Peroxidases in the chemiluminescence detection of 2- hydroxyphenyl fluorenes, it is characterised in that the DNA DNA in Mimetic Peroxidase has G- tetrad nucleotide sequences.
G- tetrad DNA and hemin molecule can form G- tetrads/hemin compounds after combining, and the DNA enzymatic has Catalytic activity is high, production cost is low, easily prepared and storage, it is thermally-stabilised good the advantages of.We with peroxide mould enzyme dna enzyme- System coexists for chemiluminescence probe in hydrogen peroxide-luminol three, realizes the chemoluminescence method detection to 2- hydroxyphenyl fluorenes.
Further, in the DNA Mimetic Peroxidases DNA sequence be PW17, Tel22, PS2.M, T30695, One kind in sequence shown in PS2.M2.
The DNA powder specifically used can be PW17DNA, and its nucleotides sequence is classified as：GGGTAGGGCGGGTTGGG.
In practical application, other DNA sequence dnas with continuous G sequence can be used to be replaced, for example:
Tel22:AGGGTTAGGG TTAGGGTTAG GG；
PS2.M:GTGGGTAGGGCGGGTTGG；
T30695:GGGTGGGTGGGTGGGT；
PS2.M2:GGGTAGGGCGGGTTGGGT。
The present invention also proposes a kind of 2- hydroxyphenyl fluorene chemical luminescence detection methods of application DNA Mimetic Peroxidases, including Following steps：
(1) it is Mimetic Peroxidase DNA enzymatic and the mixed merga pass vortex oscillator of luminol solution is uniform；
(2) after testing sample 2- hydroxyphenyl fluorene cushioning liquid is diluted, with H2O2Solution is well mixed；
(3) mixed solution for preparing step (1) is placed in chemiluminescence detection pond, then that the mixing of step (2) is molten Liquid is added rapidly in chemiluminescence detection pond, and chemiluminescence signal detection is carried out immediately.
Wherein, in the mixed luminescence system obtained by step (3), the concentration of DNA enzymatic is 1-300nM, and the concentration of luminol is 0.1-100 μM, H2O2The concentration of solution is 1-10mM.
Preferably, the DNA Mimetic Peroxidases are prepared by the following method：
S1：DNA cushioning liquid is dissolved, mixed with vortex oscillator, and 1- is handled in 80-90 DEG C of water-bath 30min, takes out, natural cooling is placed in natural cooling at room temperature, standby；
S2：The DNA solution for taking step S1 to prepare is added in centrifuge tube, and cushioning liquid is added thereto, is incubated after 0.1-5h, Hemin is added, is mixed with vortex oscillator, 0.1-10h is placed, obtains DNA Mimetic Peroxidases.
Wherein, DNA and hemin concentration ratio is 1 in described DNA Mimetic Peroxidases：1.0-1.5.
Preferably, the pH value of the mixed luminescence system of structure is 7.5-12；The cushioning liquid is by Tris, KClO4, phosphorus Acid, citric acid, hydrochloric acid, potassium chloride, KH2PO4, K2HPO4In two kinds or three kinds prepare and obtain.
It is highly preferred that the pH value of the colorimetric detection system is 8.5-10, the cushioning liquid is by Tris and KClO4Prepare And obtain.
Described 2- hydroxyphenyl fluorene chemical luminescence detection methods, in addition to step：Utilize the 2- hydroxyphenyl fluorenes of normal gradients concentration Prepare and mix luminescence system, carry out chemiluminescence signal detection, build standard curve, bring the detected value of testing sample into meter Calculate, quantitative analysis is carried out to the 2- hydroxyphenyl fluorenes pollutant of testing sample.
The beneficial effects of the present invention are：
The present invention proposes application of the DNA Mimetic Peroxidases in the chemiluminescence detection of 2- hydroxyphenyl fluorenes, sets up, perfect May be either that Environmental Health risk assessment and employment security are assessed with the DNA bioanalytical methods for having developed 2- hydroxyphenyl fluorene pollutants Reference is provided, while a kind of new highly sensitive, inexpensive detection method of exploitation, has weight to improving existing detection technique means Want meaning and preferable application value.
The present invention is established with one kind based on the inspection of Mimetic Peroxidase DNA enzymatic-hydrogen peroxide-luminol chemiluminescence system Survey the chemiluminescence method of 2- hydroxyphenyl fluorene pollutants, the chemoluminescence method has that the cycle is short, the low, sample for preparing simple, quick, cost The advantages of product consumption is few, sensitivity is high.Quick detection for environmental system 2- hydroxyphenyl fluorene pollutants provides a kind of new detection Method, this is to improve existing 2- hydroxyphenyl fluorenes pollutant monitoring technical elements significant, while having widened peroxide mould Intend application of the enzyme dna enzyme in analytical chemistry field.
Brief description of the drawings
Fig. 1 is the chemiluminescence CL spectrum of different system of determination in the embodiment of the present invention 4；A, which is represented, contains luminol, H2O2、 Mimetic Peroxidase DNA enzymatic buffer solution system；B, which is represented, contains luminol, H2O2, 2- hydroxyphenyl fluorenes, Mimetic Peroxidase DNA enzymatic buffer solution system.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
Unless otherwise specified, the conventional meanses that technological means used in embodiment is well known to those skilled in the art.
Below in conjunction with the accompanying drawings and specific embodiment the invention will be further described.
The G- tetrads of embodiment 1/Hemin Mimetic Peroxidases
By solid DNA powder pH=8.5,20mM Tris-HClO4Cushioning liquid dissolves, and is mixed with vortex oscillator, 5min in 85 DEG C of water-bath is placed in, is taken out, natural cooling at room temperature is stood.
Take appropriate above-mentioned DNA solution to be added in centrifuge tube, pH=8.5,20mMTris-KClO are added thereto4Solution is dilute Release to 5 μm of ol/L, be incubated after 2h, add 6 μm of ol/L hemin, mixed with vortex oscillator, place 2h, obtain concentration for 5 μ Mol/L G- tetrads/hemin compounds, as class peroxide mould enzyme dna enzyme.
Embodiment 2
With 20mM, pH 9.0 Tris-KClO4Buffer preparation Mimetic Peroxidase containing 300nM DNA enzymatic and 50 μM The mixed solution of luminol, is designated as A liquid；Prepare 20mMH2O2Solution, is designated as B liquid；Mixed preparing H containing 20mM2O2And 10 μM of 2- The mixed solution of hydroxyphenyl fluorene, is designated as C liquid.
1st, take the 800 above-mentioned cushioning liquid of μ L to be added in cell, take the μ L of A liquid 100 to be added in chemiluminescence detection pond, Then take 100 μ L B liquid to add in chemiluminescence detection pond, carry out chemical luminescent detecting (Fig. 1 a lines).
2nd, take the 800 above-mentioned cushioning liquid of μ L to be added in cell, take the μ L of A liquid 100 to be added in chemiluminescence detection pond, Then take 100 μ L C liquid to add in chemiluminescence detection pond, carry out chemical luminescent detecting (Fig. 1 b lines).
From figure 1 it appears that when there is luminol, hydrogen peroxide, Mimetic Peroxidase DNA enzymatic in measure system, Chemiluminescence signal (chemiluminescence intensity, CL intensity) is very strong (a lines), illustrates that Mimetic Peroxidase DNA enzymatic can Chemiluminescence is produced to be effectively catalyzed luminol, hydrogen peroxide system；In the presence of containing 2- hydroxyphenyl fluorenes, chemical luminous system chemistry Luminous signal is remarkably decreased (b lines), so as to realize the detection to 2- hydroxyphenyl fluorenes according to the change of signal.
Influences of the pH of embodiment 3 to chemiluminescence signal
The mixed luminescence system of different pH value is set, chemiluminescence detection is carried out according to the identical method of embodiment 2.Its In, cushioning liquid is respectively the Tris-KCl buffer solutions that pH value is 7.5, and Tris-KCl buffer solutions that pH value is 8.5, pH value are 9.0 Tris-KClO4The Tris-KCl buffer solutions that Tris-KCl buffer solutions that buffer solution, pH value are 10.0, pH value are 12.0.
When the pH value for mixing luminescence system is 7.5-12, obvious luminous signal can detect.
When the pH value of the mixing luminescence system is 8.5-10, luminous signal is stronger.
Embodiment 4
1st, Mimetic Peroxidase DNA enzymatic prepared by embodiment 1 is mixed with luminol solution using vortex oscillator It is even；
2nd, by 2- hydroxyphenyl fluorenes Tris-KClO4After solution dilution, with H2O2Solution is well mixed；
3rd, the mixed solution obtained by step 1 is placed in chemiluminescence detection pond, is then quickly added into the mixing obtained by step 2 Solution carries out chemiluminescence signal detection in detection cell.
Wherein, in order to verify influence of the various concentrations 2- hydroxyphenyl fluorenes to luminous signal, by the 2- hydroxyls for adding different volumes Base fluorenes solution cause the 2- hydroxyphenyl fluorene concentration in mixing system be respectively 0nmol/L, 10nmol/L, 20nmol/L, 50nmol/L, 100nmol/L、200nmol/L、500nmol/L、1000nmol/L、50000nmol/L.Simultaneously in mixed luminescence system：G- tetra- The concentration of conjuncted/Hemin Mimetic Peroxidases is 30nM, K+Concentration be 20mM, H2O2Concentration be 2mM, luminol it is dense Spend for 5 μM.
The chemiluminescence intensity of the different mixing luminescence systems of detection, is shown in Table 1.
Table 1 and chemiluminescence intensity after the effect of various concentrations 2- hydroxyphenyl fluorenes
Embodiment 5
2- hydroxyphenyl fluorenes in embodiment 2, other conditions such as luminol, H are replaced with 9- hydroxyphenyl fluorenes2O2, G- tetrads/ The chemical luminous system condition such as Hemin Mimetic Peroxidase cushioning liquid be the same as Example 1, determines and adds various concentrations 9- hydroxyls Fluorenes system chemiluminescence intensity.Chemiluminescence intensity changing value is shown in Table 2.
Table 2 changes with chemiluminescence intensity after the effect of various concentrations 9- hydroxyphenyl fluorenes
The present embodiment in kind detects the close 9- hydroxyphenyl fluorenes of structure, with 9- hydroxyphenyl fluorene change in concentration, lights strong Degree change differs markedly from 2- hydroxyphenyl fluorenes, illustrates that this method has specificity to 2- hydroxyphenyl fluorenes, thus has good practical application valency Value.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art For member, without departing from the technical principles of the invention, some improvements and modifications can also be made, these improvements and modifications Also it should be regarded as protection scope of the present invention.
SEQUENCE LISTING
<110>Beijing Research Center For Agricultural Standards and Testing
<120>Application of the DNA Mimetic Peroxidases in 2- hydroxyphenyl fluorene chemiluminescence detections
<130> KHP171111859.4TQ
<160> 5
<170> PatentIn version 3.3
<210> 1
<211> 17
<212> DNA
<213>Artificial sequence
<400> 1
gggtagggcg ggttggg 17
<210> 2
<211> 22
<212> DNA
<213>Artificial sequence
<400> 2
agggttaggg ttagggttag gg 22
<210> 3
<211> 18
<212> DNA
<213>Artificial sequence
<400> 3
gtgggtaggg cgggttgg 18
<210> 4
<211> 16
<212> DNA
<213>Artificial sequence
<400> 4
gggtgggtgg gtgggt 16
<210> 5
<211> 18
<212> DNA
<213>Artificial sequence
<400> 5
gggtagggcg ggttgggt 18

Claims (9)

  1. Application of the 1.DNA Mimetic Peroxidases in the chemiluminescence detection of 2- hydroxyphenyl fluorenes, it is characterised in that the DNA mistakes DNA in oxide analogue enztme has G- tetrad nucleotide sequences.
  2. 2. application according to claim 1, it is characterised in that DNA sequence is in the DNA Mimetic Peroxidases One kind in sequence shown in PW17, Tel22, PS2.M, T30695, PS2.M2.
  3. 3. the 2- hydroxyphenyl fluorene chemical luminescence detection methods of a kind of application DNA Mimetic Peroxidases, it is characterised in that including as follows Step：
    (1) it is Mimetic Peroxidase DNA enzymatic and the mixed merga pass vortex oscillator of luminol solution is uniform；
    (2) after testing sample 2- hydroxyphenyl fluorene cushioning liquid is diluted, with H2O2Solution is well mixed；
    (3) mixed solution for preparing step (1) is placed in chemiluminescence detection pond, then that the mixed solution of step (2) is fast Speed is added in chemiluminescence detection pond, and chemiluminescence signal detection is carried out immediately.
  4. 4. 2- hydroxyphenyl fluorenes chemical luminescence detection method according to claim 3, it is characterised in that mixed obtained by step (3) Close in luminescence system, the concentration of DNA enzymatic is 1-300nM, and the concentration of luminol is 0.1-100 μM, H2O2The concentration of solution is 1- 10mM。
  5. 5. 2- hydroxyphenyl fluorenes chemical luminescence detection method according to claim 3, it is characterised in that the DNA peroxide Analogue enztme is prepared by the following method：
    S1：DNA cushioning liquid is dissolved, mixed with vortex oscillator, and 1-30min is handled in 80-90 DEG C of water-bath, is taken Go out, natural cooling, be placed in natural cooling at room temperature, it is standby；
    S2：The DNA solution for taking step S1 to prepare is added in centrifuge tube, and cushioning liquid is added thereto, is incubated after 0.1-5h, is added Hemin, is mixed with vortex oscillator, is placed 0.1-10h, is obtained DNA Mimetic Peroxidases.
  6. 6. 2- hydroxyphenyl fluorenes chemical luminescence detection method according to claim 5, it is characterised in that described DNA peroxidating DNA and hemin concentration ratio is 1 in thing analogue enztme：1.0-1.5.
  7. 7. the 2- hydroxyphenyl fluorene chemical luminescence detection methods according to claim any one of 3-6, it is characterised in that structure it is mixed The pH value for closing luminescence system is 7.5-12；The cushioning liquid is by Tris, KClO4, phosphoric acid, citric acid, hydrochloric acid, potassium chloride, KH2PO4, K2HPO4In two kinds or three kinds prepare and obtain.
  8. 8. 2- hydroxyphenyl fluorenes chemical luminescence detection method according to claim 7, it is characterised in that the mixed luminescence system PH value be 8.5-10, the cushioning liquid is by Tris and KClO4Prepare and obtain.
  9. 9. the 2- hydroxyphenyl fluorene chemical luminescence detection methods according to claim any one of 3-6, it is characterised in that utilize standard Prepared by the 2- hydroxyphenyl fluorenes of gradient concentration mixes luminescence system, carries out chemiluminescence signal detection, builds standard curve, will treat test sample The detected value of product brings calculating into, and quantitative analysis is carried out to the 2- hydroxyphenyl fluorenes pollutant of testing sample.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102680549A (en) * 2012-04-17 2012-09-19 北京师范大学 Method for measuring 9-hydroxy fluorine based on electrochemistry hairpin DNA biosensor
CN104062288A (en) * 2014-07-09 2014-09-24 北京师范大学 Chemiluminiscence-based detection method of naphthylamine compound
CN104165914A (en) * 2014-09-06 2014-11-26 北京师范大学 Method for determining 2-hydroxyfluorene based on DNA biosensor
CN105806831A (en) * 2016-03-04 2016-07-27 北京农业质量标准与检测技术研究中心 Method for detecting chlorophenol pollutants by utilizing chemiluminescent method

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102680549A (en) * 2012-04-17 2012-09-19 北京师范大学 Method for measuring 9-hydroxy fluorine based on electrochemistry hairpin DNA biosensor
CN104062288A (en) * 2014-07-09 2014-09-24 北京师范大学 Chemiluminiscence-based detection method of naphthylamine compound
CN104165914A (en) * 2014-09-06 2014-11-26 北京师范大学 Method for determining 2-hydroxyfluorene based on DNA biosensor
CN105806831A (en) * 2016-03-04 2016-07-27 北京农业质量标准与检测技术研究中心 Method for detecting chlorophenol pollutants by utilizing chemiluminescent method

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