CN105866083A - Peroxynitrite ion detection probe as well as preparation method and application thereof - Google Patents
Peroxynitrite ion detection probe as well as preparation method and application thereof Download PDFInfo
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- CN105866083A CN105866083A CN201610217114.0A CN201610217114A CN105866083A CN 105866083 A CN105866083 A CN 105866083A CN 201610217114 A CN201610217114 A CN 201610217114A CN 105866083 A CN105866083 A CN 105866083A
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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"
- G01N2021/6432—Quenching
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Abstract
The invention discloses a peroxynitrite ion detection probe as well as a preparation method and application thereof. The peroxynitrite ion detection probe comprises a fluorescent nano material and an enzyme, wherein the enzyme is combined with the fluorescent nano material, has an oxidation-reduction property and can be selectively oxidized by peroxynitrite ions to form an oxidized enzyme; after the fluorescent nano material is radiated by excited light, electrons in an excited state can be transferred to the oxidized enzyme and cannot turn back to a base state, and then fluorescent light of the fluorescent nano material can be quenched. As an inorganic light-emitting material is adopted as fluorophore, the peroxynitrite ion detection probe disclosed by the invention is intense in light emission, good in stability and less prone to photo-bleach; the surface of the probe is modified with the enzyme with oxidation-reduction property, and the enzyme can be selectively oxidized by ONOO<->, so that the probe is not interfered by other active oxygen (ROS) or active nitrogen (RNS), and is excellent in specificity.
Description
Technical field
Present invention relates particularly to a kind of peroxynitrite (ONOO-) detect probe, its preparation method and application, such as in inspection
Survey the purposes during peroxynitrite selectively measures in living things system.
Background technology
Peroxynitrite (ONOO-) it is to be reacted, by nitric oxide and superoxide anion, a kind of strong oxidizing property thing generated in vivo
Matter.It is probably nitric oxide and produces the important step of pathology damage effect.At present, it has been found that damage at shock, ischemia-reperfusion
The diseases such as wound, atherosclerosis, degenerative brain disorder there is ONOO-Existence.Therefore, develop for ONOO-'s
Highly sensitive, high selectivity fluorescent probe is used for ONOO-Detection analysis with imaging to Physiologic Studies by significant.
At present, most detection ONOO-Fluorescent probe be all based on organic dyestuff and design, by rolling into a ball altogether at organic fluorescence
ONOO in valency coupling-Identification functional group, it is achieved selective enumeration method ONOO-Purpose, but, organic fluorescence probe has one
Settle finally sex-limited, such as, synthesize difficulty, easy photobleaching.Along with the development of materialogy, various inorganic fluorescent are nanocrystalline to be synthesized successively
Come, such as semiconductor-quantum-point, up-conversion luminescent material, noble metal cluster, silicon quantum dot, fluorescent carbon point etc., such luminescent material
The advantages such as having luminescent properties excellent, synthesis is simple, and physico-chemical property is stable, may be used for designing various fluorescent probe.But, structure
Build the ONOO nanocrystalline based on inorganic fluorescent-The report of probe is the most rarely found.
Summary of the invention
Present invention is primarily targeted at offer a kind of peroxynitrite detection probe, its preparation method and application, to overcome
Deficiency of the prior art.
For realizing aforementioned invention purpose, the technical solution used in the present invention includes:
The embodiment of the present invention provides a kind of peroxynitrite detection probe, comprising: fluorescent nano material, Yi Jiyu
Enzyme that described fluorescent nano material combines, that there is oxidation-reduction quality；Described enzyme can be by peroxynitrite selectivity oxygen
Change the enzyme forming oxidation state, and when described fluorescent nano material is after the light radiation that is excited, and the electrons being in excited state is transferred to
The enzyme of described oxidation state and ground state can not be returned to, cause the fluorescent quenching of described fluorescent nano material.
The embodiment of the present invention additionally provides the preparation method of a kind of peroxynitrite detection probe, including:
React with described fluorescent nano material with coupling reagent, make described fluorescent nano material surface form the first active group,
The second active group in described enzyme is made to react with the first active group being distributed in described fluorescent nano material surface, thus
Make described enzyme and described inorganic fluorescent material surface by chemical bonds, form described peroxynitrite detection probe.
Further, described first active group includes that carboxyl, described second active group include amino, but be not limited to this.
The embodiment of the present invention additionally provides a kind of test kit, including:
Described peroxynitrite detection probe,
And, auxiliary reagent, at least be suitable to make, described in peroxynitrite selective oxidation, there is oxidation-reduction quality for formation
Enzyme and form the liquid phase environment of the enzyme of oxidation state.
The embodiment of the present invention additionally provides the detection method of a kind of peroxynitrite, including:
Probe will may be detected at selected liquid-phase system by sample containing peroxynitrite with above-mentioned peroxynitrite
In be sufficiently mixed, by observing the fluorescent quenching degree of wherein fluorescent nano material, it is achieved to peroxynitrite contained in described sample
The detection of radical ion；
Wherein, described selected liquid-phase system is the enzyme being suitable to make have oxidation-reduction quality described in peroxynitrite selective oxidation
And form the liquid-phase system of the enzyme of oxidation state.
Further, when in described selected liquid phase environment the initial concentration of peroxynitrite be 3*10-6～5*10-4mol/L
Time, the fluorescent quenching degree of described fluorescent nano material is linear with the concentration of peroxynitrite.
Compared with prior art, the invention have the advantages that
1) the peroxynitrite detection probe provided uses phosphor as fluorogen, and it is luminous strong, stability
Good, it is difficult to photobleaching, on its surface is modified after coenzyme, it is possible to by ONOO-Selective oxidation, and will not be by other active oxygens
(ROS) or active nitrogen (RNS) interference, have excellence specificity, may be used for ONOO-Homogeneous, highly sensitive with high selectivity
Detection.
2) the peroxynitrite detection probe preparation method provided is simple, and raw material sources are extensive, beneficially large-scale production.
3) the peroxynitrite detection method provided is easy and simple to handle, it is not necessary to complex device, detection range width, detection limit up to
Sub-micromolar level, highly sensitive, accuracy is good.
Accompanying drawing explanation
In order to be illustrated more clearly that the embodiment of the present invention or technical scheme of the prior art, embodiment or prior art will be retouched below
In stating, the required accompanying drawing used is briefly described, it should be apparent that, the accompanying drawing in describing below is only described in the present invention
Some embodiments, for those of ordinary skill in the art, on the premise of not paying creative work, it is also possible to according to these
Accompanying drawing obtains other accompanying drawing.
Fig. 1 is to modify fluorescent carbon point (CDs) with coenzyme (NADH) in the present invention one exemplary embodiments and build formation ONOO-
The schematic diagram of fluorescence nano detection probe (being called for short nano-probe as follows)；
Fig. 2 is the infrared absorpting light spectra in the present invention one exemplary embodiments before and after fluorescent carbon point and coenzyme (NADH) coupling；
Fig. 3 be in the present invention one exemplary embodiments nano-probe to variable concentrations ONOO-Fluorescent quenching spectrogram；
Fig. 4 be in the present invention one exemplary embodiments nano-probe to ONOO-Specificity select test figure.
Detailed description of the invention
For making the object, technical solutions and advantages of the present invention clearer, below in conjunction with the accompanying drawings the detailed description of the invention of the present invention is entered
Row describes in detail.The example of these preferred implementations is illustrated in the accompanying drawings.The basis shown in accompanying drawing and described with reference to the accompanying drawings
The embodiment of invention is merely exemplary, and the present invention is not limited to these embodiments.
Here, also, it should be noted in order to avoid having obscured the present invention because of unnecessary details, illustrate only in the accompanying drawings
With according to the closely-related structure of the solution of the present invention and/or process step, and eliminate other details little with relation of the present invention.
A kind of peroxynitrite detection probe (also known as ONOO that one aspect of the embodiment of the present invention provides-Fluorescence nano is examined
Probing pin, following is called for short " probe ") including: fluorescent nano material, and be combined with described fluorescent nano material, there is oxidation
The enzyme of reproducibility；Described enzyme can be formed the enzyme of oxidation state by peroxynitrite selective oxidation, and when described fluorescence is received
Rice material is after the light radiation that is excited, and the electrons being in excited state is transferred to the enzyme of described oxidation state and can not return to ground state, leads
Cause the fluorescent quenching of described fluorescent nano material.
Further, described fluorescent nano material preferable autofluorescence carbon quantum dot, graphene quantum dot, semiconductor-quantum-point, on
Inorganic and/or the luminous organic materials such as changing luminous material, noble metal cluster, Fluorescent silicon nanoparticle and polymer fluorescent nano granule
In any one, but be not limited to this.
Further, described enzyme preferable autoreduction type cozymase (NADH), cytochrome C, nicotiamide, thiamine,
Riboflavin, haemachrome, dismutase, 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine. and derivant, ubiquinone etc. have in the enzyme of oxidation-reduction quality any one or
Two or more combinations, but it is not limited to this.Especially preferred, described enzyme is selected from coenzyme.
Further, described coenzyme is combined with described fluorescent nano material surface by chemical bond.
Further, described fluorescent nano material surface distributed has carboxyl, and its antioxygenic property is more excellent.
The present invention combines (particularly covalent modification) to fluorescent nano material surface by coenzyme etc. has the enzyme of oxidation-reduction quality
Structure defines a kind of electron transfer type nano-probe, at ONOO-In the presence of, the enzyme in described probe is selectively oxidized to its oxygen
Changing state, the enzyme of oxidation state is excellent electron acceptor, when fluorescent nano material is after the light radiation that is excited, is in the electronics of excited state
It is transferred to the enzyme of oxidation state, thus ground state can not be returned to, cause fluorescent quenching, its fluorescent quenching and ONOO-Concentration at certain model
Enclose (such as 3*10-6～5*10-4Mol/L) in linear, so can reach detection by quantitative ONOO-Purpose, and sensitive
Degree can reach sub-micromolar level.Particularly, when at ONOO-In the case of coexisting with Typical reactive oxygen, reactive nitrogen species, by
The probe of the present invention remains to specific detection ONOO-, and substantially without substantially doing by Typical reactive oxygen, reactive nitrogen species etc.
Disturb.
The embodiment of the present invention additionally provides the preparation method of a kind of peroxynitrite detection probe, including:
React with described fluorescent nano material with coupling reagent, make described fluorescent nano material surface form the first active group,
The second active group in described coenzyme is made to react with the first active group being distributed in described fluorescent nano material surface, thus
Make described coenzyme and described inorganic fluorescent material surface by chemical bonds, form described peroxynitrite detection probe.
Further, described first active group includes that carboxyl, described second active group include amino.
Wherein, the consumption of described fluorescent nano material can be that (preferably greater than 5 are less than or equal to 20 weight to 0～20 weight portions
Part), the consumption of described enzyme can be 5～100 weight portions (preferably greater than 0 is less than or equal to 100 weight portions), described coupling
The consumption of reagent can be 0～100 weight portions (preferably greater than 5 are less than or equal to 100 weight portions).
The embodiment of the present invention additionally provides a kind of test kit, including:
Above-mentioned peroxynitrite detection probe,
And, auxiliary reagent, at least be suitable to make coenzyme described in peroxynitrite selective oxidation form oxidation for formation
The liquid phase environment of state coenzyme.
The embodiment of the present invention additionally provides the detection method of a kind of peroxynitrite, including:
Probe will may be detected at selected liquid-phase system by sample containing peroxynitrite with above-mentioned peroxynitrite
In be sufficiently mixed, by observing the fluorescent quenching degree of wherein fluorescent nano material, it is achieved to peroxynitrite contained in described sample
The detection of radical ion；
Wherein, to form oxidation state for being suitable to make coenzyme described in peroxynitrite selective oxidation auxiliary for described selected liquid-phase system
The liquid-phase system of enzyme.
Further, when in described selected liquid phase environment the initial concentration of peroxynitrite be 3*10-6～5*10-4mol/L
Time, the fluorescent quenching degree of described fluorescent nano material is linear with the concentration of peroxynitrite.
Below in conjunction with drawings and Examples the technical solution of the present invention is further explained explanation.
In examples below, as a example by modifying NADH with fluorescent carbon quantum dot (being called for short fluorescent carbon point or carbon point, CDs), structure
Build high selective enumeration method ONOO-Fluorescent nano probe.
Refering to shown in Fig. 1, the synthesis technique of described fluorescent nano probe includes: uses mode known to industry to synthesize surface and has carboxylic
The fluorescent carbon point of base, is then passed through activation and 3-aminobenzene boric acid coupling reaction, then passes through boric acid-phenol recognition principle by NADH group
Install to carbon point surface.
More specifically, the synthesis technique of described fluorescent nano probe may include steps of:
1, fluorescent carbon point and the coupling of NADH: use common labelling technique, NADH is modified fluorescent carbon point surface.Ginseng
Read Fig. 1, first the carboxyl on fluorescent carbon point surface is activated, specifically comprise the following steps that and take 5-20 parts by weight fluorescent carbon point and 5-
100 weight portion coupling reagents, add in MES buffer solution (concentration about 0.1M, pH value=6.1), and in shaking table, low speed rocks
Oscillation incubation reacts 30 minutes, then reactant liquor dilute NaOH solution is adjusted to neutrality, adds and above-mentioned solution equal-volume
HEPES buffer solution (concentration about 0.1M, pH value=7.2) and NADH, low speed incubation reaction 4 hours in constant-temperature table,
Finally by bag filter by the coenzyme on unmodified, and little molecule coupling agent etc. separates, after dialyse 2 days, by dialysis solution concentration, and 4 DEG C
Refrigerator store is standby, it is thus achieved that fluorescent nano probe solution.Referring to is fluorescent carbon point and coenzyme in the present embodiment shown in Fig. 2
(NADH) infrared absorpting light spectra before and after coupling.
2、ONOO-Preparation: by the H of concentration about 50mM2O2The NaNO of solution and concentration about 50mM2Solution the most freezing 30
Minute, add rapidly the most chilled hydrochloric acid of 1mL after mixing, be rapidly added the NaOH solution of concentration about 1.5mM subsequently
Coolant is reacted with cancellation, stirring reaction 30 minutes, is subsequently adding MnO2To remove the hydrogen peroxide of excess.Subsequently, by reactant liquor
With filter membrane by excess MnO2Separate, filtrate at-20 DEG C of Refrigerator stores, concentration then utilize its absorbance 302nm at and mole
Absorptance (ε 302=1670M-1cm-1) calculate.
3、ONOO-Detection: aforesaid fluorescent nano probe is added dropwise to respectively the ONOO of variable concentrations-In standard solution, and add
Enter PB buffer solution (concentration about 0.1M, pH value=7.4) constant volume to same volume, on luminoscope, then measure different sample
Fluorescence intensity, it is found that along with ONOO-Be continuously added, described fluorescent nano probe produce fluorescence can be gradually lowered,
At certain ONOO-Concentration range (3*10-6～5*10-4Mol/L), in, fluorescent quenching degree is linear with its concentration (to be referred to
Shown in Fig. 3), thus can set up the standard relationship curve of fluorescent quenching and ONOO-concentration, its detection sensitivity can reach sub-micro
Mol level.
Referring to shown in Fig. 4, when the interfering material having high concentration, (Typical reactive oxygen, reactive nitrogen species, concentration compares ONOO-High by 5
Times) and ONOO-When coexisting, the fluorescent nano probe of the present embodiment remains to specific detection ONOO-, without being disturbed by these
Substantially interfering with of material.To sum up, the fluorescent nano probe of the present invention makes full use of the optical physics that inorganic nano luminescent material is excellent
Matter, the electronics acquisition performance of the enzyme excellence of oxidation state and described enzyme are to ONOO-High specific, it is possible to realize to ONOO-Width
Concentration range, selective detection highly sensitive, high.
Should be appreciated that above-described embodiment is only technology design and the feature of the explanation present invention, its object is to allow and be familiar with technique
Personage will appreciate that present disclosure and implements according to this, can not limit the scope of the invention with this.All according to present invention essence
The equivalence that god's essence is made changes or modifies, and all should contain within protection scope of the present invention.
Claims (10)
1. peroxynitrite detection probe, it is characterised in that include fluorescent nano material and with described fluorescence nano material
The enzyme with oxidation-reduction quality that material combines；Described enzyme can be formed the enzyme of oxidation state by peroxynitrite selective oxidation,
And when described fluorescent nano material is after the light radiation that is excited, be in the electrons of excited state be transferred to described oxidation state enzyme and not
Ground state can be returned to, cause the fluorescent quenching of described fluorescent nano material.
Peroxynitrite the most according to claim 1 detection probe, it is characterised in that: described fluorescent nano material bag
Include fluorescent carbon quantum dot, graphene quantum dot, semiconductor-quantum-point, up-conversion luminescent material, noble metal cluster, fluorescence silicon nanometer
Any one in particle and polymer fluorescent nano granule.
Peroxynitrite the most according to claim 1 detection probe, it is characterised in that: described enzyme includes reduced form
Cozymase (NADH), cytochrome C, haemachrome, nicotiamide, thiamine, riboflavin, dismutase, 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine. and spread out
Any one or two or more combination in biological, ubiquinone.
Peroxynitrite the most according to claim 1 detection probe, it is characterised in that: described enzyme passes through chemical bond
Be combined with described fluorescent nano material surface.
Peroxynitrite the most according to claim 4 detection probe, it is characterised in that: described fluorescent nano material table
EDS maps has carboxyl.
6. the preparation method of the peroxynitrite detection probe according to any one of claim 1-5, it is characterised in that bag
Include:
React with described fluorescent nano material with coupling reagent, make described fluorescent nano material surface form the first active group,
The second active group in described enzyme is made to react with the first active group being distributed in described fluorescent nano material surface, thus
Make described enzyme and described inorganic fluorescent material surface by chemical bonds, form described peroxynitrite detection probe.
Preparation method the most according to claim 6, it is characterised in that: described first active group includes carboxyl, described second
Active group includes amino.
8. a test kit, it is characterised in that including:
Peroxynitrite detection probe according to any one of claim 1-5,
And, auxiliary reagent, be at least suitable to make enzyme described in peroxynitrite selective oxidation to form oxidation for being formed
The liquid phase environment of the enzyme of state.
9. the detection method of a peroxynitrite, it is characterised in that including:
To may examine with the peroxynitrite according to any one of claim 1-5 by the sample containing peroxynitrite
Probing pin is sufficiently mixed in selected liquid-phase system, by observing the fluorescent quenching degree of wherein fluorescent nano material, it is achieved to described
The detection of contained peroxynitrite in sample；
Wherein, described selected liquid-phase system is to be suitable to make the enzyme described in peroxynitrite selective oxidation form oxidation state
The liquid-phase system of enzyme.
Detection method the most according to claim 9, it is characterised in that: when in described selected liquid phase environment peroxynitrite from
The initial concentration of son is 3*10-6～5*10-4During mol/L, the fluorescent quenching degree of described fluorescent nano material and peroxynitrite from
The concentration of son is linear.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106323928A (en) * | 2016-08-18 | 2017-01-11 | 浙江理工大学 | Graphene quantum dot and ionic liquid compound and application thereof to Cr(VI) detection |
| CN106556692A (en) * | 2016-11-25 | 2017-04-05 | 云南中烟工业有限责任公司 | It is a kind of for detecting method that electronics tobacco product secretes impact to cytoactive oxygen |
| CN106932368A (en) * | 2017-01-20 | 2017-07-07 | 北京理工大学 | ONOO in a kind of carbon quantum dot targeting detection mitochondria‑Method |
| CN110044864A (en) * | 2019-05-24 | 2019-07-23 | 郑州大学 | Application of the fluorescence probe based on cumarin diketone in detection peroxynitrite |
| CN111024634A (en) * | 2019-12-26 | 2020-04-17 | 湖南大学 | Prussian blue-based nano probe and preparation method and application thereof |
| CN112924423A (en) * | 2021-01-21 | 2021-06-08 | 上海交通大学 | Graphene quantum dot-based assembled microparticle material and preparation method and application thereof |
| CN113416540A (en) * | 2021-06-09 | 2021-09-21 | 安徽融慧精准医学有限公司 | Carbon dots applied to reagent for detecting drug-induced deafness and preparation method thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106323928A (en) * | 2016-08-18 | 2017-01-11 | 浙江理工大学 | Graphene quantum dot and ionic liquid compound and application thereof to Cr(VI) detection |
| CN106556692A (en) * | 2016-11-25 | 2017-04-05 | 云南中烟工业有限责任公司 | It is a kind of for detecting method that electronics tobacco product secretes impact to cytoactive oxygen |
| CN106556692B (en) * | 2016-11-25 | 2019-01-25 | 云南中烟工业有限责任公司 | A method of influence being secreted on cell activity oxygen for detecting electronics tobacco product |
| CN106932368A (en) * | 2017-01-20 | 2017-07-07 | 北京理工大学 | ONOO in a kind of carbon quantum dot targeting detection mitochondria‑Method |
| CN110044864A (en) * | 2019-05-24 | 2019-07-23 | 郑州大学 | Application of the fluorescence probe based on cumarin diketone in detection peroxynitrite |
| CN111024634A (en) * | 2019-12-26 | 2020-04-17 | 湖南大学 | Prussian blue-based nano probe and preparation method and application thereof |
| CN112924423A (en) * | 2021-01-21 | 2021-06-08 | 上海交通大学 | Graphene quantum dot-based assembled microparticle material and preparation method and application thereof |
| CN113416540A (en) * | 2021-06-09 | 2021-09-21 | 安徽融慧精准医学有限公司 | Carbon dots applied to reagent for detecting drug-induced deafness and preparation method thereof |
| CN113416540B (en) * | 2021-06-09 | 2023-08-25 | 安徽融慧精准医学有限公司 | Carbon spot applied to detection of drug-induced deafness reagent and preparation method thereof |
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|---|---|
| CN105866083B (en) | 2019-04-05 |
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