CN105001858A - Novel fluorescence probe for detecting hydrogen peroxide in alkaline environment and preparation method and biological application thereof - Google Patents
Novel fluorescence probe for detecting hydrogen peroxide in alkaline environment and preparation method and biological application thereof Download PDFInfo
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Abstract
The invention discloses a novel fluorescence probe for detecting hydrogen peroxide in an alkaline environment and a preparation method thereof, and belongs to the technical field of molecular probes. The structural formula of the probe is as follow (please see the formula in the specification), and the preparation method of the hydrogen peroxide fluorescence probe is simple. The probe detects the hydrogen peroxide in the mode of fluorescence enhancement and obvious color change and can recognize the hydrogen peroxide high selectively in a water system or an organic solvent system or an organism; the fluorescence of the probe itself is weaker, an obtained solution is purple after the probe is added in water or organic solvent, and the fluorescence of the solution is obviously enhanced and the color of the solution is changed into green after the probe acts with the hydrogen peroxide. The selectivity to hydrogen peroxide detection is high, the detection sensitivity is high, and a phenomenon is obvious and convenient to recognize.
Description
Technical field
The present invention relates to fluorescent probe of hydrogen peroxide in a kind of novel detection alkaline environment and preparation method thereof and biologic applications, this fluorescent probe can in alkaline environment efficient identification hydrogen peroxide, belong to organic molecule fluorescent probe field.
Background technology
Hydrogen peroxide chemistry formula H
2o
2, relative molecular mass 34.01 is a kind of slightly acidic colourless transparent liquids.It is a kind of strong oxidizer, has oxidisability, Bleachability.Hydrogen peroxide, as a kind of important Inorganic Chemicals and fine chemical product, has significant application value at industry, food and medicine and hygiene fields.First, hydrogen peroxide, as important oxygenant, can produce the materials such as hydroxyl radical free radical under the effect of the conditions such as catalyzer, thus the organic matter in rapid degrading waste water thoroughly, therefore in wastewater treatment, there is important application.Secondly, hydrogen peroxide has bleaches function very by force, is commonly used for SYNTHETIC OPTICAL WHITNER and is applied in paper industry, textile industry.Aqueous hydrogen peroxide solution is commonly called as hydrogen peroxide, is colourless transparent liquid.Its aqueous solution has disinfection function, can be used in medical wound sterilization and environment disinfected and foodstuffs sterilisation etc.
Hydrogen peroxide also extensively exists and plays important physiological function in organism.Hydrogen peroxide can be produced by the katalysis of the metabolism of oxygen and enzyme, is one of metabolic primary product of organism.Hydrogen peroxide is neuronal signals transduction molecule, in organism, play critical function, in regulate gene expression, systemic immune response, neuronal signals transduction process, play significant role.In physiological environment, the concentration abnormality of hydrogen peroxide may cause a series of major disease, as cardiovascular disorder, diabetes, rheumatic arthritis, tumour, nervous system disorders etc.Therefore, detect significant to hydrogen peroxide in coenocorrelation.
The detection method of current hydrogen peroxide mainly contains the methods such as electrochemical method (Electrochemical Method), ultimate analysis (EA) and plasma body-mass spectrum (ICP-MS), but the Sample Preparation Procedure more complicated of these detection methods, testing process is larger to sample damage, and the on-line analysis that cannot realize organism, therefore, the Application Areas of above-mentioned detection method is restricted.Fluorescence analysis method is the emerging detection method of a class, have that detection method is quick and convenient, detection signal is sensitive, detectability is low, can realize advantages such as the on-line analyses of organism, the context of detection of hydrogen peroxide has important application prospect in environment and organism.
Still there is the shortcomings such as the kind of probe is less, detection signal is sensitive not in current hydrogen peroxide fluorescent probe, the fluorescent probe of current exploitation is mainly detected the fluorescent probe of hydrogen oxide in neutral environment, shortage can be detected the near-infrared luminous fluorescent probe of hydrogen oxide in alkaline environment, cannot realize utilizing the acid-basicity of fluorescence to regulate organism as the hydrogen peroxide in the alkaline environment in plastosome, bile, pancreatic juice detects.Based on the problems referred to above, development of new hydrogen peroxide fluorescent probe, is detected hydrogen oxide and has important researching value in aqueous systems and coenocorrelation.
Summary of the invention
For the deficiencies in the prior art, the invention provides the fluorescent probe of hydrogen peroxide in a kind of novel detection alkaline environment.The fluorescence of this probe itself is fainter, join water or organic solvent after gained solution be purple, when with hydrogen peroxide effect after, the fluorescence of solution significantly strengthens, color becomes green.
Present invention also offers the preparation method of above-mentioned fluorescent probe, this synthetic method is simple, and the product yield of preparation is high.
Present invention also offers the application of above-mentioned fluorescent probe in aqueous systems, organic solvent system or organism.
Technical scheme of the present invention is as follows:
In novel detection alkaline environment, a fluorescent probe for hydrogen peroxide, is characterized in that, probe molecule formula is C
31h
31bO
5n
+, there is the structure shown in formula (I):
（I）。
Compound name shown in formula (I) is called (E)-4-(4-borono-benzyl)-9-(2-carboxyl phenyl)-6-(dimethylamino)-1,2,3,4-tetrahydrochysene xanthenes, are called for short CS-BOH.
The preparation method of above-mentioned fluorescent probe, comprises the following steps:
(1) between general, N dimethylamine base amino-phenol and Tetra hydro Phthalic anhydride are dissolved in benzene, in 50-70 DEG C of reaction 20-30h, obtain white solid;
(2) join in the mixing solutions of pimelinketone and the 98wt% vitriol oil by step (1) gained white solid, in 45-55 DEG C of reaction 2-12h, solid ethyl alcohol recrystallization is obtained compound 1, and its structural formula is as follows:
；
(3) by compound 1 with to boric acid ester phenyl aldehyde in sour environment, after 40-70 DEG C of reaction 2-20 h, separating-purifying obtains compound shown in formula (I).
Probe synthetic route of the present invention is as follows:
In the middle of described step (1), the mol ratio of N dimethylamine base amino-phenol and Tetra hydro Phthalic anhydride is 1:1-1.5.
In described step (1), the consumption of benzene is N dimethylamine base amino-phenol 10-70 mL between every mmole.
In the mixing solutions of described step (2) cyclohexanone and the 98wt% vitriol oil, the volume ratio of pimelinketone and the 98wt% vitriol oil is 6:20-200.
In described step (3) compound 1 be 1:1-3 to the mol ratio of boric acid ester phenyl aldehyde.
The acid that in described step (3), sour environment is used is acetic acid, acetic anhydride, methylsulfonic acid, and the volume of every mmole compound 1 acid used is 10-20 ml.
The concrete grammar of separating-purifying is in described step (3): by the solution after react, solid with methylene chloride, except desolventizing, dissolves by rotary distillation, by the mixed solvent column chromatography for separation of methylene dichloride and methyl alcohol, obtains the shown compound of formula (I).
In above-mentioned novel detection alkaline environment, the fluorescent probe of hydrogen peroxide is applied to the detection of hydrogen peroxide in aqueous systems, organic solvent system or organism.Hydrogen oxide is detected in the mode that Fluorescence Increasing, color occur obviously to change.This fluorescent probe can highly selective identification hydrogen peroxide in aqueous systems, organic solvent system or organism, the fluorescence of this probe itself is fainter, join water or organic solvent after gained solution be purple, when with hydrogen peroxide effect after, the fluorescence of solution significantly strengthens, color becomes green.
Beneficial effect of the present invention is as follows:
1, the selectivity that detects hydrogen peroxide of hydrogen peroxide fluorescent probe of the present invention is high, detects sensitive height, and phenomenon is obvious, is convenient to identify.
2, the preparation method of hydrogen peroxide fluorescent probe of the present invention is simple.
Accompanying drawing explanation
The absorption spectrum of hydrogen peroxide fluorescent probe under different concns Hydrogen Peroxide when Fig. 1 is pH=10 in the embodiment of the present invention 5; Wherein nethermost curve is the absorption curve do not added under Hydrogen Peroxide, and the concentration of curve hydrogen peroxide from the bottom up increases successively, the absorption curve of uppermost curve is concentration when being 2.8 equivalents (eq) hydrogen peroxide.
The fluorescence spectrum of hydrogen peroxide fluorescent probe under different concns Hydrogen Peroxide when Fig. 2 is pH=10 in the embodiment of the present invention 5; Wherein uppermost curve is the fluorescence curve do not added under Hydrogen Peroxide, and the concentration of curve hydrogen peroxide from top to bottom increases successively, the fluorescence curve of nethermost curve is concentration when being 2.8 equivalents (eq) hydrogen peroxide.
The absorption spectrum of hydrogen peroxide fluorescent probe under different concns Hydrogen Peroxide when Fig. 3 is pH=8 in the embodiment of the present invention 6; Wherein nethermost curve is the absorption curve do not added under Hydrogen Peroxide, and the concentration of curve hydrogen peroxide from the bottom up increases successively, the absorption curve of uppermost curve is concentration when being 2.8 equivalents (eq) hydrogen peroxide.
The fluorescence spectrum of hydrogen peroxide fluorescent probe under different concns Hydrogen Peroxide when Fig. 4 is pH=8 in the embodiment of the present invention 6; Wherein uppermost curve is the fluorescence curve do not added under Hydrogen Peroxide, and the concentration of curve hydrogen peroxide from top to bottom increases successively, the fluorescence curve of nethermost curve is concentration when being 2.8 equivalents (eq) hydrogen peroxide.
Fig. 5 is the comparison diagram adding the fluorescence intensity change after different biological micromolecule in the embodiment of the present invention 7.
Embodiment
Below by specific embodiment, the present invention will be further described, but be not limited thereto.Raw materials used in embodiment, be conventional commercial products if no special instructions.
Embodiment 1
The preparation of compound 1
N dimethylamine base phenol (0.50 g between inciting somebody to action, 3.03 mmol) and Tetra hydro Phthalic anhydride (0.49 g, 3.33 mmol) in 180 mL benzene 60 DEG C of reactions within 24 hours, obtain white solid, white solid being joined 20 mL contains in the 98wt% vitriol oil of 6 ml pimelinketone again, 50 DEG C are reacted 3 hours, solid ethyl alcohol recrystallization obtains compound 1 (0.22 g, 0.45 mmol).
Synthetic route is as follows:
Embodiment 2
The preparation of the fluorescent probe of hydrogen peroxide in novel detection alkaline environment
Reaction scheme is as follows:
Preparation process, comprises step as follows:
By compound 1(0.377 g, 1.0 mmol) and to boric acid ester phenyl aldehyde (0.157 g, 1.2 mmol) in 20 ml acetic acid, in 50 DEG C of reaction 12 h, obtain dark solution, rotary distillation is except desolventizing, and solid with methylene chloride dissolves, cross column chromatography for separation with methylene dichloride and methanol mixed solvent, obtain target compound
cS-BOH; Yield: 50%.
1H NMR (400 MHz, DMSO-d6) δ 8.16 (m, 2H), 8.06 (s, 1H), 7.86 (t,
J = 7.2, 2H), 7.72 (d,
J = 8.4, 1H), 7.51 (s, 2H), 7.35 (d,
J = 7.6, 1H), 6.8 (m, 2H), 3.58 (q,
J = 6.4, 4H ), 2.8 (m, 2H), 2.07 (m, 1H), 1.67 (m, 3H), 1.23 (t,
J = 6.8, 6H ).
13C NMR (101 MHz, CDCl3) δ 169.94, 152.38, 152.09, 149.39, 146.29, 142.08, 134.56, 133.47, 131.95, 129.98, 129.38, 128.59, 127.52, 125.04, 123.45, 119.00, 110.20, 109.77, 108.93, 104.61, 97.18, 44.44, 29.70, 27.25, 22.99, 22.32, 12.55.
Embodiment 3
The preparation method of hydrogen peroxide fluorescent probe as described in Example 2, unlike:
Wherein be 3 mmol to boric acid ester phenyl aldehyde consumption, acetic acid is replaced with acetic anhydride, acid consumption be 20 mL, temperature of reaction is 60 DEG C, and the reaction times is 12 h.
Embodiment 4
The preparation method of hydrogen peroxide fluorescent probe as described in Example 2, unlike:
Wherein be 1 mmol to boric acid ester phenyl aldehyde consumption, acetic acid is replaced with methylsulfonic acid, acid consumption be 10mL, temperature of reaction is 50 DEG C, and the reaction times is 10 h.
Embodiment 5
The titration experiments of pH=10 fluorescent probe and hydrogen peroxide
In the PBS damping fluid of pH=10, add the fluorescent probe that starting point concentration is 1 mM, make the concentration of fluorescent probe in solution be 10 μMs.Then, the starting point concentration adding different amount is successively the hydrogen peroxide of 1.85 mM, the concentration of hydrogen peroxide in solution is made to be respectively 0.044 μM, 0.088 μM, 0.132 μM, 0.176 μM, 0.264 μM, 0.352 μM, 0.44 μM, 0.528 μM, 0.704 μM, 0.88 μM, 1.056 μMs, 1.232 μMs, 1.408 μMs, 1.584 μMs, 1.76 μMs, 2.2 μMs, 2.64 μMs, do not add hydrogen peroxide in contrast, leave standstill and within 0.5 hour, make hydrogen peroxide and fluorescent probe fully react.
Test the Absorption and fluorescence spectrum under different Hydrogen Peroxide respectively by absorption spectrometer and fluorescence spectrophotometer, the excitation wavelength of fluorescence spectrum is 600 nm, and emission wavelength is 660 nm, and determined wavelength is 660 nm, and result respectively as shown in Figure 1 and Figure 2.As shown in Figure 2, along with the concentration of hydrogen peroxide increases, the fluorescence intensity under 663 nm wavelength reduces gradually, illustrates that fluorescent probe can respond hydrogen peroxide.
Embodiment 6
The titration experiments of pH=8 fluorescent probe and hydrogen peroxide
In the PBS damping fluid of pH=8, add the fluorescent probe that starting point concentration is 1 mM, make the concentration of fluorescent probe in solution be 10 μMs.Then, the starting point concentration adding different amount is successively the hydrogen peroxide of 1.85 mM, the concentration of hydrogen peroxide in solution is made to be respectively 0.044 μM, 0.088 μM, 0.132 μM, 0.176 μM, 0.264 μM, 0.352 μM, 0.44 μM, 0.528 μM, 0.704 μM, 0.88 μM, 1.056 μMs, 1.232 μMs, 1.408 μMs, 1.584 μMs, 1.76 μMs, 2.2 μMs, 2.64 μMs, do not add hydrogen peroxide in contrast, leave standstill and within 0.5 hour, make hydrogen peroxide and fluorescent probe fully react.
Test the Absorption and fluorescence spectrum under different Hydrogen Peroxide respectively by absorption spectrometer and fluorescence spectrophotometer, the excitation wavelength of fluorescence spectrum is 660 nm, and emission wavelength is 720 nm, and determined wavelength is 720 nm, and result respectively as shown in Figure 3, Figure 4.As shown in Figure 4, along with the concentration of hydrogen peroxide increases, the fluorescence intensity under 720 nm wavelength strengthens gradually, illustrates that fluorescent probe can respond hydrogen peroxide.
Embodiment 7
Fluorescent probe is detected the selectivity test of hydrogen oxide
As described in Example 5, under same test condition, in solution, add other excessive bioactive small molecule, test the fluorescence spectrum added after different bioactive small molecule, excitation wavelength is 660 nm, and emission wavelength is 720 nm, determined wavelength is 720 nm, and result as shown in Figure 5.As shown in Figure 5, common bioactive small molecule is as hypochlorous acid, hydroxyl radical free radical, tertbutyl peroxide free radical, tertbutyl peroxide, Peracetic Acid, hydrogen sulfide, halfcystine, homocysteine, gsh, nitrogen protoxide, nitrite anions, nitrate radical, inferior sulfate radical, sulfate radical etc., fluorescence intensity only has hydrogen peroxide to change obviously, other biological active small molecular does not produce interference to detected result, can prove that this fluorescent probe has higher selectivity to hydrogen peroxide.
Claims (9)
1. the fluorescent probe of hydrogen peroxide in novel detection alkaline environment, it is characterized in that, probe molecule formula is C
31h
31bO
5n
+, there is the structure shown in formula (I):
（I）。
2. a preparation method for fluorescent probe according to claim 1, is characterized in that, it comprises the following steps:
(1) between general, N dimethylamine base amino-phenol and Tetra hydro Phthalic anhydride are dissolved in benzene, in 50-70 DEG C of reaction 20-30h, obtain white solid;
(2) join in the mixing solutions of pimelinketone and the 98wt% vitriol oil by step (1) gained white solid, in 45-55 DEG C of reaction 2-12h, solid ethyl alcohol recrystallization is obtained compound 1, and its structural formula is as follows:
；
(3) by compound 1 with to boric acid ester phenyl aldehyde in sour environment, after 40-70 DEG C of reaction 2-20 h, separating-purifying obtains compound shown in formula (I).
3. the preparation method of fluorescent probe according to claim 2, is characterized in that, in the middle of described step (1), the mol ratio of N dimethylamine base amino-phenol and Tetra hydro Phthalic anhydride is 1:1-1.5.
4. the preparation method of fluorescent probe according to claim 2, is characterized in that, in described step (1), the consumption of benzene is N dimethylamine base amino-phenol 10-70 mL between every mmole.
5. the preparation method of fluorescent probe according to claim 2, is characterized in that, in the mixing solutions of described step (2) cyclohexanone and the 98wt% vitriol oil, the volume ratio of pimelinketone and the 98wt% vitriol oil is 6:20-200.
6. the preparation method of fluorescent probe according to claim 2, is characterized in that, in described step (3) compound 1 be 1:1-3 to the mol ratio of boric acid ester phenyl aldehyde.
7. the preparation method of fluorescent probe according to claim 2, is characterized in that, the acid that in described step (3), sour environment is used is acetic acid, acetic anhydride, methylsulfonic acid, and the volume of every mmole compound 1 acid used is 10-20 ml.
8. the preparation method of fluorescent probe according to claim 2, it is characterized in that, the concrete grammar of separating-purifying is in described step (3): by the solution after having reacted, rotary distillation is except desolventizing, solid with methylene chloride is dissolved, by the mixed solvent column chromatography for separation of methylene dichloride and methyl alcohol, obtain compound shown in formula (I).
9. the application of fluorescent probe according to claim 1 in aqueous systems, organic solvent system or organism.
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