CN108623578B - Benzoxadiazole pH fluorescent probe, preparation method and application - Google Patents
Benzoxadiazole pH fluorescent probe, preparation method and application Download PDFInfo
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Abstract
The invention discloses a benzoxazole pH fluorescent probe, a preparation method and application thereof, wherein the structural formula of the fluorescent probe is as follows:
also comprises the following preparation steps of preparing 4-chloro-7-nitrobenzofurazan and 1- [ (2-pyridyl) methyl]Dissolving piperazine and triethylamine in an organic solvent, and carrying out reaction and post-treatment to obtain a fluorescent probe; the 4-chloro-7-nitrobenzofurazan and the 1- [ (2-pyridyl) methyl group]The molar ratio of piperazine is 1: 1; the volume ratio of the triethylamine to the organic solvent is 1: 10; the fluorescent probe is used for detecting the dynamic change of the pH value. The invention has simple synthesis and short time consumption, and can more conveniently and effectively detect the dynamic change of pH by utilizing colorimetric and fluorescence enhancement dual-channel probe technology.
Description
Technical Field
The invention relates to the field of applied biology, in particular to a benzoxazole pH fluorescent probe, a preparation method and application thereof.
Background
Intracellular pH is generally between 6.8-7.4, and when intracellular pH tends to be acidic, it often causes more diseases, such as inflammation, tumor, cystic fibrosis, etc. Therefore, monitoring the dynamic changes of intracellular pH (4.5-6.0) plays an important role in understanding and treating related diseases. Fluorescence spectroscopy detection techniques have unique advantages for detecting pH changes over a spatiotemporal distribution, compared to pH measurement methods such as microelectrode, NMR and absorption spectroscopy. In addition, the fluorescence probe method has the advantages of high selectivity and sensitivity, easy operability of a nondestructive analysis and detection system and the like, and has wide application in the fields of environment, chemistry, biology, medicine and the like. Most of the currently reported pH fluorescent probes are fluorescence-enhanced, but few of the fluorescent probes can detect the pH value in a colorimetric manner by observing with the naked eye. Document CN107488446A discloses a colorimetric ratio type acid-base fluorescent probe, and a preparation method and an application thereof, but the preparation method needs to be performed under a protective atmosphere, synthesis is inconvenient, synthesis time is long, and only reflux reaction time needs 4-6 hours.
Disclosure of Invention
The invention aims to solve the technical problem of providing a benzoxazole pH fluorescent probe, a preparation method and application, which are simple in synthesis and short in time consumption, and can more conveniently and effectively detect the dynamic change of the pH value by utilizing a colorimetric and fluorescence-enhanced dual-channel probe technology.
The invention comprises that the structural formula is shown as formula I:
the pH detection range of the fluorescent probe is 4.0-6.0, and when the pH value is greater than 7.0, the color of the fluorescent probe is light yellow; when the pH value is less than 7.0, the color of the fluorescent probe gradually deepens with the decrease of the pH value, gradually deepens from light yellow to dark yellow, and the color deepens with the decrease of the pH value, as shown in FIG. 2. In fig. 2, (a) the curve is a change curve of absorbance at pH 4, and the color of the sample is dark yellow; (b) the curve is the change of absorbance at pH 7.4, and the sample is light yellow in color. Therefore, the fluorescent probe of the present invention can detect pH colorimetrically.
The principle of the fluorescent probe for detecting the pH value is as follows: under an acidic condition, a 4-position nitrogen atom of piperidine in the fluorescent probe is combined with a proton, and the formula is shown as a formula II:
therefore, Photoinduced Electron Transfer (PET) in fluorescent probe molecules is realized, fluorescence enhancement and absorption spectrum of the probe compounds are obviously changed, and finally, pH value change is distinguished through color change colorimetry of the probes.
The fluorescent probe is easy to store, and can be stored at normal temperature for 10-12 months without change.
Also comprises the following synthesis steps:
(1) dissolving 4-chloro-7-nitrobenzofurazan, 1- [ (2-pyridyl) methyl ] piperazine and triethylamine in an organic solvent, reacting and mixing for 1 hour at room temperature;
(2) and (3) performing rotary evaporation on the reaction liquid, purifying the filtrate by silica gel column chromatography, and eluting by using petroleum ether and ethyl acetate in the silica gel column chromatography, wherein the volume ratio of the petroleum ether to the ethyl acetate is 4:1, thereby finally obtaining the fluorescent probe.
The molar ratio of the 4-chloro-7-nitrobenzofurazan to the 1- [ (2-pyridyl) methyl ] piperazine is 1: 1.
The volume ratio of the triethylamine to the organic solvent is 1: 10.
The fluorescent probe is used for detecting the dynamic change of the pH value.
The invention has the beneficial effects that:
(1) the fluorescent probe is simple to synthesize and consumes less time.
(2) The fluorescence and absorption spectra of the probe compound are obviously changed under different pH values, and the detection result can be identified through fluorescence or color comparison.
(3) The fluorescent probe has reversibility characteristics, which is beneficial to realizing the repeatability of probe detection and enables the probe to detect the change condition of pH value in real time.
(4) The fluorescent probe has good selectivity, is not influenced by common metal ions and anions, and has higher precision.
(5) The fluorescent probe has fast reaction and basically no influence of time on the detection effect.
(6) The fluorescent probe has low toxicity, and the concentration of the practical fluorescent probe is well controlled, so that the survival of cells is not greatly influenced.
Drawings
FIG. 1 is a reaction equation for synthesizing the fluorescent probe of the present invention.
FIG. 2 is a graph showing the UV-VIS absorption spectra of the fluorescent probe of the present invention at pH 4.1 and pH 7.4.
FIG. 3 shows a fluorescent probe of the present invention1HNMR atlas.
FIG. 4 is a graph showing the change of fluorescence intensity of the fluorescent probe of the present invention in buffers with different pH values.
FIG. 5 is a graph of the intensity of the emission peak of the fluorescent probe of the present invention as a function of pH.
FIG. 6 is a graph showing the recovery of the fluorescent probe of the present invention at pH 4.1 and 7.4.
FIG. 7 is a graph showing the toxicity test of the fluorescent probe of the present invention in cells.
FIG. 8 is a graph showing the change in fluorescence intensity of the fluorescent probe of the present invention when mixed with different analytes at pH 4.1.
FIG. 9 is a graph showing the change of fluorescence intensity with time at pH 2.26(a) and pH 4.1(b) for the fluorescent probe of the present invention.
Detailed Description
Example 1
The synthesis of the fluorescent probe comprises the following experimental steps:
(1) 4-chloro-7-nitrobenzofurazan (200mg, 1mmol), 1- [ (2-pyridyl) methyl ] piperazine (177mg, 1mmol) and triethylamine (0.5mL) were dissolved in 5mL of anhydrous dichloromethane, and the reaction mixture was stirred at room temperature for 1 hour, and the synthesis reaction equation of the fluorescent probe is shown in FIG. 1;
(2) the reaction solution was rotary evaporated and the filtrate was purified by column chromatography with a volume ratio of petroleum ether to ethyl acetate of 4:1 to give a yellow solid (296mg, yield 87%).
The nuclear magnetic resonance H spectrum of the obtained fluorescent probe is as follows:1H NMR(500MHz,CDCl3) δ (ppm):8.45(d, J ═ 8.5,1H,),7.39-7.37(m,3H),7.34-7.32(m,1H),6.31(d, J ═ 9,1H),4.15(t, J ═ 5,4H),3.63(s,1H),2.73(t, J ═ 55Hz, 4H); as shown in fig. 3.
Example 2
The experimental procedure of example 2 was the same as that of example 1 except that the molar ratio of 4-chloro-7-nitrobenzofurazan to 1- [ (2-pyridyl) methyl ] piperazine was changed to 2:1 in step (1).
It was found that the final product of example 2 was structurally identical to the final product of example 1, and the method for synthesizing the probe of the present invention is not limited to the method described in the examples.
Example 3
The experimental procedure of example 3 was the same as that of example 1 except that the molar ratio of 4-chloro-7-nitrobenzofurazan to 1- [ (2-pyridyl) methyl ] piperazine was changed to 1:2 in step (1).
It was found that the final product of example 3 was structurally identical to the final product of example 1, and the method for synthesizing the probe of the present invention is not limited to the method described in the examples.
Example 4
The experimental procedure of example 4 was the same as that of example 1 except that anhydrous dichloromethane was replaced with 2, 2-dimethylpropane liquid in step (1).
It was found that the final product of example 4 was structurally identical to the final product of example 1, and the method for synthesizing the probe of the present invention is not limited to the method described in the examples.
Example 5
To verify that the fluorescent probe has the effect of detecting pH, the following experiment was performed.
The experimental steps are as follows:
(1) dissolving the fluorescent probe obtained in example 1 in acetonitrile to obtain 1mM probe mother liquor;
(2) 3ml of PBS buffer solution with the pH values of 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.2, 4.4, 4.6, 4.8, 5.0, 5.2, 5.4, 5.6, 5.8, 6.0, 6.5, 7.0, 7.5 and 8.0 is prepared;
(3) 30uL of the probe stock solution was added to the buffer solution, delayed for 10 seconds, and the emission wavelength was measured.
As shown in FIG. 4, the fluorescent probe of the present invention shows an obvious emission peak (corresponding to an excitation wavelength of 450nm) at 550nm under different pH values, wherein the smaller the pH value, the higher the emission peak, which indicates that the fluorescent probe can perform fluorescence detection well at different pH values.
As shown in fig. 5, the emission peak is most clearly varied between pH 4.0 and 6.0, that is, in the range of pH 4.0 to 6.0, the probe of the present invention can accurately detect the variation of pH.
Example 6
To examine the reversibility characteristics of the fluorescent probe of the present invention, the following experiment was carried out.
The experimental steps are as follows:
(1) adding the fluorescent probe in the example 1 into PBS buffer;
(2) the pH of the buffer was adjusted from 7.4 to 4.1 with HCl (0.1M) and NaOH (0.1M), then from 4.1 to 7.4, and the cycle was repeated 4 times, measuring the emission wavelength at 550nm after each adjustment.
As shown in FIG. 6, the fluorescence probe of the invention has reversibility of spectral response in the pH adjustment process, and the reversibility is beneficial to realizing the repeatability of probe detection, so that the probe can detect the change situation of pH value in real time.
Example 7
To detect the toxicity of the probe, the following experiment was performed.
The experimental steps are as follows:
(1) the fluorescent probes prepared in example 1 were prepared at 37 ℃ to different concentrations: 5uM, 10uM, 20uM, 30uM, and 60 uM;
(2) weighing 0.5g of probe compound, dissolving in 100ml of Phosphate Buffered Saline (PBS), and filtering with 0.22um filter membrane to remove bacteria in the solution to obtain a probe compound solution;
(3) preparing a single cell suspension by using a culture solution containing 10% fetal calf serum, and inoculating 1000-;
(4) after 3-5 days of culture, adding 20ul of probe compound solution into each hole, continuing to incubate for 4 hours, terminating the culture, carefully absorbing and removing the supernatant liquid cultured in the holes, adding 150ul of DMSO into each hole, and shaking for 10 minutes to fully dissolve crystals;
(5) exciting with 450nm wavelength, measuring the light absorption value of each hole on an enzyme-linked immunosorbent assay instrument, recording the result, and calculating the cell survival rate.
As shown in FIG. 7, the cell survival rate decreases slowly with the increasing concentration of the fluorescent probe, and when the concentration of the fluorescent probe reaches 60uM, the cell survival rate is more than 80%, which indicates that the probe has weak toxicity, but the toxicity is low, and in the actual detection process, the cell survival cannot be greatly influenced as long as the concentration of the probe is well controlled.
Example 8
To detect the sensitivity and interference resistance of the probe, the following experiment was performed.
The experimental steps are as follows:
(1) preparing PBS (phosphate buffer solution) with pH 4.1;
(2) the following ions were added to the buffer: co2+、Fe3+、Cu2+、Ni2+、Mn2+、Cr3+、Na+、Ca2+、Mg2+、Cd2+、Li+、K+、F-、Cl-、Ac-；
(3) The fluorescent probe obtained in example 1 was added to the ion-added buffer solution, and the emission wavelength at 550nm was measured.
As shown in FIG. 8, after the common metal ions and anions are mixed with the probe solution, the fluorescence spectrum response is almost absent, which indicates that the fluorescence probe of the invention has strong anti-interference performance, and the common metal ions and anions do not influence the selectivity of the fluorescence probe to hydrogen ions, indicating that the fluorescence probe has good selectivity.
Example 9
To verify the response speed of the probe test to the pH solution, the following experiment was performed.
The experimental steps are as follows:
(1) preparing 8 parts of PBS (phosphate buffer solution) with pH 4.1;
(2) the fluorescence probe preparation completion time of the embodiment 1 is taken as a starting point, and the emission intensity at 550nm of the solution is tested at intervals, wherein the intervals are respectively as follows: 0.2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28, 30 minutes.
As shown in fig. 9, the pH of curve (a) was 2.26 and the pH of curve (b) was 4.1. As can be seen from FIG. 9, the fluorescent probe has very fast fluorescence response in the solutions with pH values of 2.26 and 4.1, and the value of the emission peak of the fluorescent probe has substantially no change with the passage of time, which indicates that the fluorescent probe of the present invention can complete the detection rapidly in a short time, and the detection effect of the fluorescent probe is not influenced by time.
Claims (6)
1. A benzoxazodiazole pH fluorescent probe is characterized in that the structural formula is shown as formula I:
2. a method for preparing the benzoxazole-based pH fluorescent probe according to claim 1, characterized in that: the method comprises the following steps: dissolving 4-chloro-7-nitrobenzofurazan, 1- [ (2-pyridyl) methyl ] piperazine and triethylamine in an organic solvent, and carrying out reaction and post-treatment to obtain the fluorescent probe.
3. The method for preparing a benzoxazole-based pH fluorescent probe according to claim 2, characterized in that: the molar ratio of the 4-chloro-7-nitrobenzofurazan to the 1- [ (2-pyridyl) methyl ] piperazine is 1: 1.
4. The method for preparing a benzoxazole-based pH fluorescent probe according to claim 2, characterized in that: the volume ratio of the triethylamine to the organic solvent is 1: 10.
5. The method for producing a benzoxazole-based pH fluorescent probe according to claim 2 or 4, characterized in that: the organic solvent is anhydrous dichloromethane.
6. Use of the benzoxazole-based pH fluorescent probe according to claim 1, characterized in that: the fluorescent probe is used for detecting the dynamic change of the pH value in non-diagnosis and treatment.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010092917A1 (en) * | 2009-02-10 | 2010-08-19 | 国立大学法人名古屋大学 | Test reagent for fluorescent observation of intestinal mucosa |
| JP2013104687A (en) * | 2011-11-10 | 2013-05-30 | Carna Biosciences Inc | Novel fluorescent probe and novel method for screening kinase inhibitor |
| CN106565694A (en) * | 2016-10-09 | 2017-04-19 | 北京化工大学 | NBD-organic amine fluorescence probe, and preparation method and application thereof |
| CN107382900A (en) * | 2017-06-30 | 2017-11-24 | 曲阜师范大学 | A kind of preparation method and applications of pH fluorescence probes |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010092917A1 (en) * | 2009-02-10 | 2010-08-19 | 国立大学法人名古屋大学 | Test reagent for fluorescent observation of intestinal mucosa |
| JP2013104687A (en) * | 2011-11-10 | 2013-05-30 | Carna Biosciences Inc | Novel fluorescent probe and novel method for screening kinase inhibitor |
| CN106565694A (en) * | 2016-10-09 | 2017-04-19 | 北京化工大学 | NBD-organic amine fluorescence probe, and preparation method and application thereof |
| CN107382900A (en) * | 2017-06-30 | 2017-11-24 | 曲阜师范大学 | A kind of preparation method and applications of pH fluorescence probes |
Non-Patent Citations (4)
| Title |
|---|
| Development of a pH-activatable fluorescent probe and its application for visualizing cellular pH change;Rong Huang et al.;《Analyst》;20121231;第137卷(第19期);第4418-4420页及supporting information * |
| Synthesis and screening of 3-substituted thioxanthen-9-one-10,10-dioxides;Pedro M.J.Lory et al.;《Bioorganic & Medicinal Chemistry Letters》;20070825;第17卷;第5940-5943页 * |
| 一个基于NBD-NH2荧光团的增强型pH 荧光探针及其细胞造影研究;李静等;《无机化学学报》;20131231;第29卷(第12期);第2528-2534页 * |
| 苯并噁二唑类荧光探针的合成及对pH的检测;张春香等;《广州化工》;20190930;第47卷(第17期);第109-111页 * |
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