CN106905310B - It is a kind of to detect hypochlorous fluorescence probe and its preparation method and application - Google Patents
It is a kind of to detect hypochlorous fluorescence probe and its preparation method and application Download PDFInfo
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Abstract
The present invention provides a kind of hypochlorous acid fluorescence probes being enable to respond quickly and the fluorescence probe to apply in detection aqueous solution or in biological cell existing for hypochlorous acid.When the fluorescence probe is applied to detection HClO, it is reacted with HClO, so as to cause the change of fluorescence, there is photoluminescence peak at 440nm, and fluorescence intensity is positively correlated with HClO concentration, to indicate the presence of HClO or quantitative determine the concentration of HClO, the fluorescence detection of HClO and cell imaging in biosystem can be applied to.Each synthesis step of fluorescence probe in the present invention is simple, purification of products is simple, it is strong for the specificity of HClO effect, resist a variety of chaff interferents, the quick detection of hypochlorous acid molecular probe is realized, and detects and limits low, high sensitivity, the range of linearity is wide, has broad application prospects in biomolecule detection field.
Description
Technical field
The present invention relates to one kind quickly detect hypochlorous fluorescence probe and preparation method thereof and spectrum test, cell at
Application as in, belongs to small organic molecule fluorescence probe field.
Background technique
Active oxygen (ROS) be in organism many physiology and pathologic process play extremely important effect it is some it is oxygen-containing from
By the general name of base (hydroxyl radical free radical and ultra-oxygen anion free radical etc.) and non-free radical (hypochlorous acid and hypochlorous acid etc.).Organism
It is interior that various ROS are generated by enzymatic and non-enzymatic reaction under the physiology such as oxidative stress, inflammation and pathologic condition.The biology in modern age
Medical research shows that the generation, development and the aging of body of the ROS and some diseases generated in vivo has close relationship.
Hypochlorous acid (HClO) belongs to one kind of active oxygen, as a kind of efficient fungicide, in the immune system of life
It plays an important role.The hypochlorous acid of endogenous cellular is mainly by leucocyte (such as monocyte, acidophic cell, neutrophil(e) granule
Cell etc.) in myeloperoxidase/hydrogen peroxide/chloride ion system generate.The hypochlorous acid that cell immune response generates, still
Once hypochlorous concentration is abnormal in cell, will cause including rheumatic arthritis, cardiovascular disease and cancer
A variety of diseases.Exactly because hypochlorous acid has so important physiology and pathological significance, hypochlorous detection is caused
The extensive attention of people.
Can be used for selective enumeration method hypochlorous acid/hypochlorite method has very much, such as iodometric titration, colorimetric method, chemistry
Luminescence method, coulometry, polarography and radiolysis method etc..However, these methods are often comparatively laborious, a few thing must be in organic Jie
It is carried out in matter or organic/aqueous medium, limits its application.Compared to the above, fluorescence probe is considered as biological study ideal
Means because instrument needed for fluorescence detection is relatively easy, selectivity and high sensitivity, detection range is wide, and the response time is fast
Speed, and detection process does not destroy sample, and to cells compromise also very little, fluorescence detection combination microscope can be provided in real time
As a result.
One fluorescence probe with application prospect should have change in fluorescence before and after effect obviously, to target molecule to respond
Fastly, the advantages that selectivity is good, synthesis is simple.In general, fluorescence probe consists of two parts: a part is fluorescence signal base
Group, another part is recognition group, and hypochlorous recognition site has thioether bond, azanol, anilino- etc..When probe identify target,
Chemical reaction can be converted into a spectral signal.In recent years, there is the report of hypochlorous acid fluorescence probe in more detection living cells
Road, however there are raw materials to be not easy to obtain, synthesis step and complicated for operation, anti-interference is poor, and recognition site is single etc. various asks
Topic.Therefore, it is particularly important applied to hypochlorous detection to develop new recognition site, thus to be secondary during research cytopathy
Chloric acid concentration situation of change provides visual detection instrument.
Summary of the invention
For current hypochlorous acid fluorescence probe detect problem encountered, the present invention provides one kind can resist it is dry
It disturbs, quick response, the hypochlorous acid fluorescence probe with new recognition site and preparation method thereof.
Another object of the present invention is provide fluorescence probe hypochlorous acid molecule in detection aqueous solution or in biological cell
Using.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of hypochlorous fluorescence probe of detection, has the structure as shown in following formula (I):
The synthetic route of the fluorescence probe is as follows:
The preparation method of the fluorescence probe, comprising the following steps:
(1) phenthazine is dissolved in into n,N-Dimethylformamide (DMF), sodium hydride is slowly added in 0 DEG C, stirred, in room
Temperature is lower to be added iodoethane, stirs 4-8 hours, suction filtration obtains white precipitate, i.e. N- ethyl-phenothiazine；
(2) phosphorus oxychloride is slowly added to dry DMF at 0 DEG C, room temperature reaction 2 hours is transferred to, obtains DMF solution；
Product N- ethyl-phenothiazine in step (1) is dissolved in dichloroethanes, is added in above-mentioned DMF solution, after reaction 1 hour, is risen
Temperature continues back flow reaction 12-18 hours to 80-100 DEG C；Reaction solution is extracted with dichloromethane, after anhydrous sodium sulfate is dry, column layer
Analyse isolated N- ethyl-phenothiazine -2- formaldehyde；
(3) N- ethyl-phenothiazine -2- formaldehyde, 2- mercaptoaniline and sodium pyrosulfite are added in the reaction flask containing DMF,
It is heated to reflux under nitrogen atmosphere, reaction to contact plate detection raw material disappears, and extracts, concentration, it is glimmering that column chromatography for separation obtains hypochlorous acid
Light probe.
In the synthetic method of above-mentioned fluorescence probe, phenthazine in step (1): the molar ratio of iodoethane is 2:2-3；Step
(3) N- ethyl-phenothiazine -2- formaldehyde in: the molar ratio of 2- hydroxyanilines is 2:2-3.
In the synthetic method of above-mentioned fluorescence probe, reflux temperature is 80-100 DEG C in step (2).
When the fluorescence probe is applied to detection hypochlorous acid, fluorescence probe unstressed configuration itself or fluorescence are very weak, with secondary chlorine
After acid reaction, the compound with formula (II) is generated, fluorescence is made to change, is used for qualitative detection hypochlorous acid.Detect hypochlorous acid
When solution, excitation wavelength 360nm, with gradually increasing for hypochlorous acid content, the photoluminescence peak at 440nm gradually increases
By force；When detecting hypochlorous acid in cell, excitation wavelength 405nm has photoluminescence peak at 440nm.It is glimmering within the scope of a certain concentration
Luminous intensity is linearly positively correlated with hypochlorous acid concentration, to realize the hypochlorous concentration of quantitative determination.The fluorescence probe can answer
For hypochlorous sensing detection in aqueous solution or biosystem；The sensing detection includes fluorescence detection and cell imaging.
The invention has the following advantages that each synthesis step of probe is simple, purification of products is simple；To the special of hypochlorous acid reaction
One property is strong, resists a variety of chaff interferents, realizes the quick detection of hypochlorous acid molecular probe, high sensitivity, and detection limits low, the range of linearity
Extensively.Specificity and significant color change based on hypochlorous acid probe in the present invention can be used as in display aqueous solution and biological
Specificity indicator existing for intracellular hypochlorous acid molecule can carry out real-time qualitative detection and content sensing detection.So this hair
Bright is that one kind is simple, and quickly, sensitive hypochlorous acid molecular specificity detection reagent has wide in biomolecule detection field
Application prospect.
Detailed description of the invention
Fig. 1 is one middle probe NS-ClO of embodiment1H NMR spectra；
Fig. 2 is variation of the probe NS-ClO fluorescence intensity with HCLO concentration；
Fig. 3 is the relationship of probe NS-ClO fluorescence intensity Yu HCLO concentration；
Fig. 4 is that probe NS-ClO fluorescence intensity changes with time；
Fig. 5 is probe NS-ClO selectivity histogram；
Fig. 6 is the fluorescence imaging that probe NS-ClO is applied to cell exogenous HClO；
Fig. 7 is the fluorescence imaging that probe NS-ClO is applied to endogenous HClO in cell.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System,
The number of compound corresponds to the number of compound in above scheme in embodiment.
The synthesis of 1 fluorescence probe NS-ClO of embodiment.
(1) compound 1 (0.1mmol, 201.287mg) is dissolved in 2mL DMF, is slowly added to sodium hydride in 0 DEG C
After stirring 30min, iodoethane (0.15mmol, 223.95mg) is added at room temperature in (0.15mmol, 35.6mg), and stirring 6 is small
When, suction filtration obtains white precipitate, i.e. compound 2.
(2) it by phosphorus oxychloride (2mmol, 300mg) at 0 DEG C, is slowly added in the dry DMF of 1mL, is transferred to room temperature reaction
2 hours.Compound 2 (1mmol, 229mg) is dissolved in the dichloroethanes of 1mL, is added in above-mentioned DMF solution, is reacted 1 hour
Afterwards, 90 DEG C are warming up to, is reacted 16 hours.Reaction solution is extracted with dichloromethane, and after anhydrous sodium sulfate is dry, column Chromatographic purification is obtained
To compound 3.
(3) by compound 3 (2mmol, 510mg), 2- mercaptoaniline (2mmol, 340mg) and sodium pyrosulfite (2mmol,
380mg) it is added in the reaction flask containing 15mL DMF, under nitrogen atmosphere after being heated to reflux 5h, contact plate detection reaction to original
Material disappears, and extracts, and concentration, column chromatography for separation obtains probe NS-ClO.Yield 60%.1H NMR(400MHz,CDCl3)δ8.05
(d, J=8.1Hz, 1H), 7.92-7.84 (m, 1H), 7.82 (d, J=2.1Hz, 1H), 7.51-7.44 (m, 1H), 7.40-7.33
(m, 1H), 7.19-7.10 (m, 1H), 6.97-6.86 (m, 1H), 3.97 (q, J=7.0Hz, 1H), 1.45 (t, J=7.0Hz,
1H)。
The relationship of embodiment 2 fluorescence probe NS-ClO fluorescence intensity and HClO concentration.
Fluorescence probe NS-ClO prepared by Example 1 is dissolved in DMF, and 1mmol/L stock solution is made.Containing 5%DMF
Phosphate buffer solution (PBS solution) (0.1mol/L, pH=7.5) in be added 15 μ L stock solutions, be added various concentration (0-2
×10-4μM, i.e. 0-20equiv) NaClO standard solution (i.e. spontaneous generation soda acid is flat in aqueous solution in neutral conditions by NaClO
Weighing apparatus is mobile and generates HClO, similarly hereinafter), final volume 3mL, measure its photoluminescent property (λ ex=360nm, raster width 5nm,
5nm), for fluorescence spectrum as shown in Fig. 2, abscissa is wavelength, ordinate is relative intensity of fluorescence.According to NS-ClO fluorescence intensity with
The variation of HCLO concentration is mapped, as shown in Figure 3 using HCLO concentration as abscissa by ordinate of fluorescence intensity.From the figure 3, it may be seen that
As the increase fluorescence intensity of HClO concentration gradually increases, and in 0-1 × 10-4In μM concentration range, fluorescence intensity is dense with HClO
Degree is linear to be positively correlated.
The fluorescence intensity of 3 fluorescence probe NS-ClO of embodiment changes with time.
From taken out in fluorescence probe stock solution in embodiment 2 15 μ L be added containing 5%DMF PBS solution (0.1mol/L,
PH=7.5 in), NaClO (2 × 10 is added-4μM) standard solution final volume be 3mL, measured respectively in 0-8min every 1min
Its photoluminescent property, testing conditions such as embodiment 2.For fluorescence spectrum as shown in figure 4, abscissa is wavelength, ordinate is relative fluorescence
Intensity.From fig. 4, it can be seen that be added probe NS-ClO after, be directly added into above-mentioned NaClO solution, at any time reaction 1 minute after fluorescence
Intensity increase is rapidly reached maximum, and fluorescence intensity is kept stable at 8 minutes or more, realizes the quick detection of HClO.
Selectivity of the 4 fluorescence probe NS-ClO of embodiment to different ions.
It is added in 5mL centrifuge tube from 30 μ L are taken out in embodiment 2 in fluorescence probe stock solution, is separately added into equimolar
The interfering substance standard solution of amount: glutathione, L-cysteine, homocysteine, fluorine ion, chloride ion, bromide ion,
Hydroxy radical, peroxynitrite ion, di-t-butyl peroxide, tert-butyl hydroperoxide, nitric oxide, hydrogen peroxide, nitrous
Acid group, cobalt ions, copper ion, nickel ion, one of NaClO standard solution that equimolar amounts is added, test system solution body
Product is 3mL, the fluorescence emission spectrum variation of solution is detected after 20min, as shown in Figure 4, in which: 1- is no added, 2-GSH, 3-
Cys, 4-Hcy, 5-F-, 6-Cl-, 7-Br-, 8-OH, 9-ONOO-, 10-DTBP, 11-TBHP, 12-NO, 13-H2O2, 14-NO2 -,
15-Co+, 16-Cu2+, 17-Ni+, 18-ClO-, ordinate is relative intensity of fluorescence.By Fig. 5 it can be found that other interfering substances pair
The fluorescence of probe NS-ClO has little effect, and the addition of HClO solution significantly increases the fluorescence of probe NS-ClO.
5 fluorescence probe NS-ClO of embodiment is to cell exogenous HClO fluorescence imaging.
Fluorescence probe NS-ClO is applied to the detection of HClO in HeLa cell, fluorescence imaging is carried out, as shown in fig. 6, saying
This bright fluorescence probe can be realized the detection of cell exogenous HClO.Specific steps are as follows:
A) 20 μM of probe DMF solutions are added in the culture solution for giving birth to HeLa cell and are cultivated in carbon dioxide incubator
0.5h, light field imaging, such as figure are a), it can be seen that the rough profile of cell；
B) by cell 405nm laser excitation in a), image b) is obtained；
C) it will scheme a) b) to be superimposed with figure, and obtain image c)；
D) 20 μM of probe DMF solutions are added in the culture solution for giving birth to HeLa cell and are cultivated in carbon dioxide incubator
0.5h, after HClO is added, light field imaging, such as figure are d), it can be seen that the rough profile of cell；
E) cell in d) is obtained into image e) with 405nm laser excitation；
F) it will scheme d) e) to be superimposed with figure, and obtain image f).
Cell imaging of the 6 fluorescence probe NS-ClO of embodiment to endogenous cellular HClO.
Fluorescence probe NS-ClO is applied to carry out fluorescence imaging, such as Fig. 7 to endogenic HClO in 264.7 cell of Raw
It is shown, illustrate that this fluorescence probe can carry out fluorescence imaging to HClO endogenic in cell.Specific steps are as follows:
A) 20 μM of probe DMF solutions are added in the culture solution for giving birth to 264.7 cell of Raw in carbon dioxide incubator
Middle culture 0.5h, light field imaging, such as figure are a), it can be seen that the rough profile of cell；
B) cell in a) is obtained into image with 405nm laser excitation, obtains image b)；
C) it will scheme a) b) to be superimposed with figure, and obtain image c)；
D) LPS (2 μ g/mL) and PMA (2 μ g/mL) incubation 2h first is added in 264.7 cell of Raw, then by 10 μM of probe DMF
Solution is added in the culture solution of cell, and the light field imaging obtained after 0.5h is cultivated in carbon dioxide incubator, is imaged
Figure is d), it can be seen that the rough profile of cell；
E) cell in d) is obtained into image e) with 405nm laser excitation；
F) it will scheme d) e) to be superimposed with figure, and obtain image f).
Claims (7)
1. a kind of hypochlorous fluorescence probe of detection, has the structure as shown in following formula (I):
Formula (I).
2. a kind of synthetic method of fluorescence probe described in claim 1, comprising the following steps:
(1) phenthazine is dissolved in into n,N-Dimethylformamide (DMF), sodium hydride is slowly added in 0 DEG C, stirred, at room temperature
Iodoethane is added, stirs 4-8 hours, suction filtration obtains white precipitate, i.e. N- ethyl-phenothiazine；
(2) phosphorus oxychloride is slowly added to dry DMF at 0 DEG C, room temperature reaction 2 hours is transferred to, obtains DMF solution；It will step
Suddenly product N- ethyl-phenothiazine is dissolved in dichloroethanes in (1), is added in above-mentioned DMF solution, reaction 1 hour after, heating after
It is back flow reaction 12-18 hours continuous；Reaction solution is extracted with dichloromethane, and after anhydrous sodium sulfate is dry, column chromatography for separation obtains N- second
Base phenthazine -2- formaldehyde；
(3) N- ethyl-phenothiazine -2- formaldehyde, 2- mercaptoaniline and sodium pyrosulfite are added in the reaction flask containing DMF, in nitrogen
Atmosphere is heated to reflux that the reaction was continued under enclosing, reaction to contact plate detection raw material disappears, and extracts, concentration, column chromatography for separation obtains time chlorine
Sour fluorescence probe.
3. the synthetic method of fluorescence probe according to claim 2, which is characterized in that phenthazine in step (1): iodoethane
Molar ratio be 2:2-3；N- ethyl-phenothiazine -2- formaldehyde in step (3): the molar ratio of 2- mercaptoaniline is 2:2-3.
4. the synthetic method of fluorescence probe according to claim 2, which is characterized in that reflux temperature is 80- in step (2)
100 ℃。
5. a kind of application of fluorescence probe described in claim 1 in detection hypochlorous acid, which is characterized in that the fluorescence probe is answered
For hypochlorous sensing detection in aqueous solution or biosystem, the sensing detection includes fluorescence detection and cell imaging.
6. application of the fluorescence probe according to claim 5 in detection hypochlorous acid, which is characterized in that the fluorescence probe
The excitation wavelength detected applied to hypochlorous acid in aqueous solution is 360nm, and the excitation wavelength detected applied to hypochlorous acid in cell is
405nm。
7. application of the fluorescence probe according to claim 5 in detection hypochlorous acid, which is characterized in that the probe exists
There is photoluminescence peak at 440nm, the fluorescence intensity of the probe is linearly positively correlated with hypochlorous concentration.
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| CN108997326B (en) * | 2018-09-04 | 2020-09-22 | 济南大学 | Thiol fluorescent probe and preparation method and application thereof |
| CN109535114B (en) * | 2018-12-27 | 2020-11-20 | 浙江工业大学 | Fluorescent compound sensitive to NaClO and preparation and application thereof |
| CN109928966B (en) * | 2019-02-15 | 2021-04-02 | 山东师范大学 | Metal organic framework material based on phenothiazine and preparation method and application thereof |
| CN110128371A (en) * | 2019-04-24 | 2019-08-16 | 中国科学院上海微系统与信息技术研究所 | A kind of phenthazine benzaldehyde derivative and preparation method thereof, phenthazine quinoline fluorescence probe and its preparation method and application |
| CN112694469B (en) * | 2020-11-27 | 2022-02-08 | 山西大学 | Pyrrosinyl-based HOCl fluorescent probe, and preparation method and application thereof |
| CN112500386B (en) * | 2020-11-27 | 2022-02-08 | 山西大学 | Near-infrared HClO fluorescent probe based on piroctone olamine, preparation and application thereof |
| CN115161022A (en) * | 2022-07-12 | 2022-10-11 | 皖西学院 | Cationic fluorescent carbon dots sensitively responding to hypochlorous acid and preparation method thereof |
| CN116814249B (en) * | 2023-06-25 | 2024-03-26 | 江南大学 | Method for constructing chiral nano probe based on cobalt ions and copper nano luminous clusters and application |
| CN117603203B (en) * | 2024-01-18 | 2024-04-12 | 德州学院 | Ratio fluorescent probe and preparation method and application thereof |
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