CN106243123B - A kind of fluorescence probe for detecting hydrogen peroxide and its application - Google Patents
A kind of fluorescence probe for detecting hydrogen peroxide and its application Download PDFInfo
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- CN106243123B CN106243123B CN201610613861.6A CN201610613861A CN106243123B CN 106243123 B CN106243123 B CN 106243123B CN 201610613861 A CN201610613861 A CN 201610613861A CN 106243123 B CN106243123 B CN 106243123B
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- 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"
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- 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
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Abstract
The invention discloses a kind of fluorescence probe ACR for detecting hydrogen peroxide, belong to technical field of analytical chemistry.The fluorescence probe is switch by parent, 2 azido-methyl aryl esters of Rhodamine Derivatives, its chemical structural formula such as formula (I）It is shown.The fluorescence probe synthesis of the present invention is simple, it is easy to use, it specific can be reacted with hydrogen peroxide and discharge fluorescence, there is good selectivity to hydrogen peroxide, anti-interference is preferable in the presence of other related oxides in detection hydrogen peroxide process, and the hydrogen peroxide in living cells can be detected.
Description
Technical field
The invention belongs to technical field of analytical chemistry, is related to a kind of fluorescence probe for detecting hydrogen peroxide and its application.
Background technology
Hydrogen peroxide is a kind of important reactive oxygen species, is had in living organism activity and external environment of crucial importance
Application.In natural environment, hydrogen peroxide can be used for purifying running water, when biology carries out vital movement, peroxide
Change the function that hydrogen plays immunological marker in cellular process.Caused hydrogen peroxide in biological metabolic processes
（H2O2）It is biogenic, hydrogen peroxide important role in physiology course.The research of recent years shows,
Hydrogen peroxide physiology and pathologic process can be adjusted with the role of signaling molecule, Proliferation, Differentiation and migration with cell
Process is closely bound up, and in addition, hydrogen peroxide such as inflammation, body defenses etc. in many pathologic processes also play
Important function.But many diseases are also due to caused by excessive hydrogen peroxide, such as：The diseases such as cancer, Alzheimer's disease
Disease.Therefore the hydrogen peroxide in the detection living organism and external environment of real-time quantitative has very important significance.
The inspection to hydrogen peroxide is mainly realized by modes such as colorimetric method, electrochemical process, titration, chromatographies at present
Survey, although the detection hydrogen peroxide that the above method can be sensitive and selective, their most complex operations, by dry
Disturbing factor influences big, time-consuming effort again, can not realize to the hydrogen peroxide in organism in real time, rapid, in situ quantitation analysis and
Detection.Therefore it is badly in need of design at present and develops new hydrogen peroxide detection method.In recent years, people passed through fluorescence probe method
And the combination of laser confocal imaging technology, it is " visible, fixed that the hydrogen peroxide in biological tissue and living cells has been carried out well
Amount, in real time " detection.Research shows that fluorescence probe method has easily operation, high selectivity and sensitivity, good biofacies
Capacitive, the advantages that also making detection object exempt from destruction, it is widely used in the fields such as chemistry, biology, environment and medical science.
The fluorescence probe of detection hydrogen peroxide mainly has boric acid and borate ester fluorescence probe and sulfonic acid esters fluorescence probe,
2', 7'- dichlorofluorescin（2', 7'-dichlorodihydrofluorescein, DCFH）It is a kind of traditional detection
ROS probe, its own unstressed configuration, when its being oxidized property material is oxidized to 2', 7'- dichlorofluoresceins（2',7'-
Dichlorofluorescein, DCF）When, that is, send intense fluorescence.However, this fluorescence probe is not only to intracellular reactive
Oxygen has response, also there is response to other oxidation materials, sensitivity and all poor to the selectivity of different oxidizing substances.Pass through
It is incorporated into using boric acid base group or borate as the reaction site of probe in fluorophore molecule and cleverly solves this worry.By
In the fluorescence that boric acid base group or borate energy quencher fluorophore are sent, thus molecular probe only send in itself faint fluorescence or
Do not light, and after hydrogen peroxide and boric acid base group or borate react, borate is hydrolyzed into as hydroxyl, is then sent
Fluorescence.It is improved so fluorescence probe can be used as reaction site by introducing borate to the selectivity of hydrogen peroxide.
Chang groups are reported using fluorescein as illuminophore, the fluorescein using borate group as fluorescence reaction site
Double borate fluorescence probe PF of class1（J Am Chem Soc, 2004, 126: 15392-15393.）, the probe is to peroxide
Other reactive oxygen compounds of the response ratio of change hydrogen are high more than 500 times, can detect the mistake of the intracellular micromole's level of human embryonic kidney
Hydrogen oxide, reaction mechanism are as follows：
。
Novel fluorescence the probe FS-1 and FS-2 that Tang Bo problems are combined into（B volumes of Chinese science:Chemistry, 2009,39
(6): 473-480.）Can be with the PNF-1 probes of detection ultra-oxygen anion free radical（Chem Bio Chem, 2007, 8:
453-458.）It is used in combination while goes to detect living cells hydrogen peroxide and ultra-oxygen anion free radical（Wherein FS-2 transmitting
Wavelength is 520 nm）.FS-2 and PNF-1 is respectively as detection hydrogen peroxide and the probe of ultra-oxygen anion free radical, its fluorescence
Spectrum is not interfere with each other, and is realized well while is detected the operation of ultra-oxygen anion free radical and hydrogen peroxide in living cells.Should
Probe has strong response to hydrogen peroxide in the case where simulating physiological condition, shows good selectivity, and will not by etc.
The other biological material of amount and the interference of active oxygen.Learn that mouse peritoneal macrophages are containing difference by cell imaging experiment
Cultivated in the nutrient solution of concentration of hydrogen peroxide or add after being stimulated by PMA after probe FS-1 and FS-2 show it is bright green glimmering
Light, and sensitivity is very high, and the concentration of hydrogen peroxide change to micromole's rank in cell can also produce response.Experiment card above
Understand that probe FS-1 and FS-2 have high film penetrating power and good selectivity and sensitivity.The probe is to study
The signal transduction path of hydrogen oxide mediation provides certain analysis method, and specific testing mechanism is as follows：
。
In summary, acted on to further disclose and probe into hydrogen peroxide in environmental and biological materials, design synthesis
Selectivity is strong, the hydrogen peroxide fluorescence probe of high sensitivity has very important theoretical and realistic meaning.
The content of the invention
The present invention is for the deficiency in prior art, there is provided a kind of fluorescence probe that can detect hydrogen peroxide, and will
The probe application detects the imaging applications of hydrogen peroxide in living cells.
A kind of fluorescence probe ACR for detecting hydrogen peroxide of the present invention, it is characterised in that the change of the fluorescence probe
Learn structural formula such as formula（）It is shown：
。
The fluorescence probe ACR of above-mentioned detection hydrogen peroxide is prepared in the following manner：
The synthesis of intermediate A -1：To 4- lignocaines ketone acid and the trifluoroacetic acid to chloro resorcinol（TFA）Suspension
In, molecular sieve is added, is heated to 90 oC afterwards, is stirred 6 hours.Mixture is cooled to room temperature after terminating and concentrated by reaction, is obtained
To crude product, it is recrystallized in the mixed solution of petroleum ether and ethyl acetate, obtains red solid A-1.
Probe ACR synthesis：EDCI, DMAP and centre are added into the dichloromethane solution of 2- (azido-methyl) benzoic acid
Body A-1, room temperature is heated to afterwards and is stirred 12 hours.After the completion of reaction, resulting solution is poured into water and extracted with dichloromethane
Take, the organic layer of merging, with saturated common salt water washing, afterwards with anhydrous MgSO4It is dried and concentrated, obtains Red oil crude product.
Crude product purifies to obtain colorless oil as product ACR through silica gel chromatographic column.
The synthesis of the present invention is as follows：
。
The application of fluorescence probe hydrogen peroxide in living cells is detected of detection hydrogen peroxide of the present invention.
Fluorescence probe of the present invention can should be in the hydrogen peroxide in detection living cells, specific detection method be：
10 μM of ACR is added in Hela cells, is cultivated 15 minutes under 37 oC, cell does not have fluorescence substantially.Afterwards by Hela cells
After being cultivated 15 minutes under 37 oC with 10 μM of ACR, washed three times with PBS, change culture medium, then buffered by hydrogen peroxide molten
Liquid（25 μM）Culture 15 minutes, cell sends strong fluorescence.Experiment shows that ACR has good to the hydrogen peroxide in cell
Imaging acts on, and the hydrogen peroxide that may be advantageously employed in detection organism, has in biomedicine etc. important potential
Application value.
Beneficial effects of the present invention：
A kind of fluorescence probe of detection hydrogen peroxide involved in the present invention, using Rhodamine Derivatives as parent, is folded with 2-
N-methyl aryl ester is switch, can cross and simply, be used with hydrogen peroxide specific reaction, fluorescence probe of the invention synthesis
It is convenient, it specific can be reacted with hydrogen peroxide and discharge fluorescence, will not be by other phases in hydrogen peroxide process is detected
The interference of oxide is closed, there is good selectivity to hydrogen peroxide, the hydrogen peroxide in living cells can be detected, is imaged
Effect is good, and low to cytotoxicity.
Brief description of the drawings
Fig. 1 is fluorescence probe ACR1H NMR spectras.
Fig. 2 is fluorescence probe ACR13C NMR spectras.
Fig. 3 is fluorescence probe ACR selective light spectrogram.
Fig. 4 is that fluorescence probe ACR changes response light spectrogram with concentration of hydrogen peroxide.
Fig. 5 is fluorescence probe ACR response time spectrograms.
Fig. 6 is fluorescence probe ACR anti-interference test charts.
Fig. 7 is fluorescence probe ACR to Hela intracellular hydrogen peroxide detection figures.
Embodiment
The invention will be further described with reference to the accompanying drawings and examples.
Embodiment 1：
The synthesis of intermediate A -1：To 4- lignocaine ketone acids（6.0 g, 19.1 mmol）With to chloro resorcinol 15（2.8
G, 19.1 mmol）TFA（20 mL）In suspension, molecular sieve is added（2.0 g）, 90 oC are heated to afterwards, are stirred 6 hours.
Mixture is cooled to room temperature after terminating and concentrated by reaction, crude product is obtained, by it in petroleum ether：Ethyl acetate is 1：1 it is mixed
Close and recrystallized in solution, obtain red solid A-1（7.0 g, 95%）.
Probe ACR synthesis：To 2- (azido-methyl) benzoic acid（252.25 mg, 1.43 mmol）Dichloromethane（5
mL）EDCI is added in solution（341.50 mg, 1.78 mmol）, DMAP（72.54 mg, 0.59 mmol）With 4- lignocaine ketone
Acid（500.0 mg, 1.19 mmol）, room temperature is heated to afterwards and is stirred 12 hours.After the completion of reaction, resulting solution is poured into water
（30 mL）In and use dichloromethane（3 × 20 mL）Extraction, the organic layer of merging, with saturated common salt water washing, afterwards with anhydrous
MgSO4It is dried and concentrated, obtains Red oil crude product.Crude product purifies through silica gel chromatographic column（Petroleum ether：Ethyl acetate=5：
1）Obtain colorless oil as product ACR（358.81 mg, 52%）.1H NMR (400 MHz, CDCl3) δ 8.36 (dt, J =
9.2, 4.6 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.74 (tt, J = 4.1, 2.0 Hz, 1H),
7.71 - 7.69 (m, 1H), 7.69 - 7.65 (m, 1H), 7.63 (d, J = 7.2 Hz, 1H), 7.60 -
7.52 (m, 1H), 7.28 (d, J = 3.4 Hz, 2H), 6.90 (s, 1H), 6.60 (d, J = 8.9 Hz,
1H), 6.47 (d, J = 2.5 Hz, 1H), 6.41 (dd, J = 9.0, 2.6 Hz, 1H), 4.99 - 4.75
(m, 2H), 3.46 - 3.18 (m, 3H), 1.24 - 1.10 (m, 6H). 13C NMR (101 MHz, CDCl3) δ
169.25, 163.75, 152.55, 150.97, 149.80, 147.87, 138.68, 135.14, 133.96,
132.00, 129.93, 129.90, 129.21, 128.82, 128.41, 126.84, 126.79, 125.15,
124.16, 121.33, 119.04, 112.67, 108.86, 104.33, 97.57, 83.01, 52.98, 44.52,
12.49. HRMS-ESI (m / z) [M + H]+ calcd for: C32H26ClN4O5 +, 581.1513, found:
581.1523. FTIR (KBr, cm-1): 3450, 2918, 2113, 1751,1419, 1343, 1143, 1049,
811, 745.
The present invention has carried out measure of merit to the probe ACR that embodiment 1 obtains：
1. ACR is selectively analyzed
The CH of 80 equivalents of hydrogen peroxide is added in 5 μM of ACR3OH/PBS（The wherein concentration of hydrogen peroxide
For 10 mM, pH=7.4, CH3OH：PBS=5：95）, testing result such as Fig. 3, work as λex = 470 nm, λem =
During 560 nm, ACR has strong fluorescence response to hydrogen peroxide, and ACR does not almost respond to other oxidizing substances,
Illustrate that ACR has excellent selectivity to hydrogen peroxide.
2. ACR changes response analysis to concentration of hydrogen peroxide
0-200 equivalent is added in 5 μM of ACR（50 - 400 μM）Hydrogen peroxide when, fluorescence response intensity with
The increase of hydrogen peroxide addition increases in regular, testing result such as Fig. 4, as a result illustrates that ACR detects to concentration of hydrogen peroxide
Scope is wide and high sensitivity.
3. ACR is to hydrogen peroxide response time analysis
The CH of 80 equivalents of hydrogen peroxide is added in 5 μM of ACR3OH/PBS, to ACR and hydrogen peroxide
Response time is detected, and testing result such as Fig. 5, as a result shows, after hydrogen peroxide is added in 0-120 minute, ACR pairs
The fluorescence response intensity of hydrogen peroxide linearly strengthens with the increase of time, in the short period of time with regard to that can reach good fluorescence
Intensity.As a result show, ACR can be effectively applied to the detection of hydrogen peroxide to the response quickly of hydrogen peroxide.
4. ACR anti-interferences are analyzed
It is real that probe ACR has carried out competition in the presence of other disturbing molecules such as various oxidizing substances and mercaptan
Test, to detect ACR anti-interference.Testing result such as Fig. 6, in hydrogen peroxide and other biological mercaptan or other oxidizing substances
ACR still can produce stable fluorescence response to it in the case of coexisting.It is excellent that the above results show that ACR has to hydrogen peroxide
Anti-interference, efficiently can detect hydrogen peroxide in the presence of other oxidizing substances and biological thiol.
5. applications of the ACR in cell detection
The ACR for adding 10 μM in Hela cells is cultivated 15 minutes under 37 oC, testing result such as Fig. 7, by B in Fig. 7
Shown, cell does not have fluorescence substantially.After we cultivate Hela cells and 10 μM of ACR 15 minutes under 37 oC, washed with PBS
Wash three times, change culture medium, then by hydrogen peroxide cushioning liquid（25 μM）Culture 15 minutes, as shown in E in Fig. 7, cell is sent
Strong fluorescence.Experiment shows that ACR has good imaging effect to the hydrogen peroxide in cell, may be advantageously employed in detection
Hydrogen peroxide in organism, there is important potential using value in biomedicine etc..
Above-mentioned although the embodiment of the present invention is described with reference to accompanying drawing, not to the limit of invention scope
System, the art personnel should be understood that on the basis of technical scheme those skilled in the art need not pay
Go out various modifications or deformation that creative work can make still within protection scope of the present invention.
Claims (2)
- A kind of 1. fluorescence probe for detecting hydrogen peroxide, it is characterised in that the chemical structural formula of the fluorescence probe ACR（I）Institute Show：。
- 2. according to a kind of fluorescence probe of detection hydrogen peroxide described in claim 1, it is characterised in that the fluorescence probe ACR can apply to detect hydrogen peroxide in living cells.
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| CN107033158B (en) * | 2016-12-29 | 2019-04-12 | 济南大学 | A kind of colorimetric fluorescence probe and preparation method thereof of hypersensitive analysis mercury ion |
| CN107325062B (en) * | 2017-08-02 | 2020-05-12 | 浙江大学 | Fluorescent probe for detecting hydrogen peroxide activity and preparation and application thereof |
| CN108623611B (en) * | 2018-06-22 | 2020-09-25 | 北京工业大学 | Synthesis and application of fluorescent probe for detecting hydrogen peroxide |
| CN112625049A (en) * | 2020-11-06 | 2021-04-09 | 上海应用技术大学 | Azido group modified fluorescein compound and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1844124A (en) * | 2006-04-11 | 2006-10-11 | 山东师范大学 | Fluorescent probe for detecting hydrogen peroxide and its synthesis method and use |
| CN105038762A (en) * | 2015-06-04 | 2015-11-11 | 济南大学 | Ratio-dependent fluorescent probe for detecting hydrogen peroxide and application of ratio-dependent fluorescent probe |
| CN105647518A (en) * | 2016-01-29 | 2016-06-08 | 山东师范大学 | Fluorescent probe for detecting hydrogen peroxide and preparation method and application thereof |
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| CN1844124A (en) * | 2006-04-11 | 2006-10-11 | 山东师范大学 | Fluorescent probe for detecting hydrogen peroxide and its synthesis method and use |
| CN105038762A (en) * | 2015-06-04 | 2015-11-11 | 济南大学 | Ratio-dependent fluorescent probe for detecting hydrogen peroxide and application of ratio-dependent fluorescent probe |
| CN105647518A (en) * | 2016-01-29 | 2016-06-08 | 山东师范大学 | Fluorescent probe for detecting hydrogen peroxide and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| A Selective, Cell-Permeable Optical Probe for Hydrogen Peroxide in Living Cells;Michelle C. Y. et al.;《J.AM.CHEM.SOC.》;20041104;第126卷(第47期);15392-15393 * |
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