CN109160906B - Application of acryloyl ester compound taking thiazole as matrix as fluorescent probe and preparation method thereof - Google Patents
Application of acryloyl ester compound taking thiazole as matrix as fluorescent probe and preparation method thereof Download PDFInfo
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- CN109160906B CN109160906B CN201811260252.2A CN201811260252A CN109160906B CN 109160906 B CN109160906 B CN 109160906B CN 201811260252 A CN201811260252 A CN 201811260252A CN 109160906 B CN109160906 B CN 109160906B
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- 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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- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- 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
Abstract
An application and its preparation method of taking thiazole as the acrylic ester compound of the parent body as the fluorescent probe, the fluorescent probe BTHA prepared only has a fluorescence peak at 507nm in the mixed solution of dimethyl sulfoxide, 4-hydroxyethyl piperazine ethanesulfonic acid buffer salt and DMSO, after adding GSH gradually, the fluorescence intensity at 507nm is weakened continuously, a new fluorescence peak appears at 460nm, and the peak intensity is enhanced with GSH addition, thus realize the proportion detects GSH, have the ratio colorimetry, the characteristic of detecting GSH with high selectivity; the fluorescent probe can realize specific detection on GSH, Cys and Hcy and generate different fluorescent signals, so that the GSH, Cys and Hcy can be distinguished and visualized for detection with high selectivity, and the fluorescent probe has no response to other amino acids, anions and metal cations, has the characteristics of good selectivity and high sensitivity, and is simple in preparation method and easy to synthesize.
Description
Technical Field
The invention relates to the technical field of biological analysis, in particular to application of an acryloyl compound taking thiazole as a matrix as a fluorescent probe and a preparation method thereof.
Background
Thiol compounds (GSH, Cys, Hcy) play an important role in human physiology, Chemical Society Review,2013, (44): 6019-. Abnormal levels of cysteine (Cys) are associated with a number of diseases such as slow growth, hair loss, edema, lethargy, liver damage, loss of muscle and fat, skin lesions, etc. Abnormal homocysteine (Hcy) content may lead to cognitive disorders, cardiovascular diseases, alzheimer's disease, and the like. More specifically, in cells, GSH is the most abundant thiol in small molecules (1-10mmol), and redox equilibrium thiol groups exist between oxidized glutathione (GSSG). GSH is understood to play a key role therein, controlling oxidative stress to maintain intracellular homeostasis. In addition, its content abnormality may cause many diseases including cancer, Alzheimer's disease and cardiovascular disease and the like, Angewandte chemical International Edition,2011, (50):10690 and 10693.
The fluorescence analysis method is an important spectral analysis means for qualitatively or quantitatively analyzing substances according to the spectral characteristics or intensity change of the substances after the fluorescent molecules/probes and the analytes are reacted, and has the advantages of high sensitivity, good selectivity, simple and convenient method, rapidness, accuracy, wide linear range and the like, Chemistry,2009, (15) 5096-5103; 49-51. in recent years, with the rapid development of computer technology, material science, life science and the like, the fluorescence analysis technology plays an increasingly important role in numerous fields (such as medical research, life science and the like) and becomes an effective means of Chemical Society Reviews,2011 in the fields of environmental monitoring, drug screening, diagnosis of serious diseases and the like, (40) 3483-; chemical Society Reviews,2013, (42): 622-661. based on this, selective detection of GSH, Cys and Hcy by fluorescence analysis is very important, and most of the reported probes can not distinguish and detect the three kinds of amino acids which are common in organisms.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide the application of taking the acryloyl ester compound with thiazole as a parent body as the fluorescent probe and the preparation method thereof, which can take the acryloyl ester compound (BTHA) with thiazole as the parent body as the fluorescent probe, detect GSH with high selectivity and ratio, detect Cys and Hcy with high sensitivity, and have the characteristics of simple synthesis, sensitive detection and specific selectivity.
In order to achieve the purpose, the invention adopts the technical scheme that:
the fluorescent probe is an acryloyl compound (BTHA) taking thiazole as a parent body, and the structural formula of the fluorescent probe is shown as follows:
the fluorescent probe is applied to the selective and ratio detection of GSH in a dimethyl sulfoxide and Hepes mixed solution system.
The fluorescent probe BTHA is 5 mu mol/L, and can detect GSH in a system of 10mmol/L Hepes and 9:1 DMSO (volume/volume), wherein the GSH is 5-60 mu mol/L.
The fluorescent probe reacts with GSH, Cys and Hcy at room temperature, the change difference of the fluorescent property is obvious, and the specific phenomena are as follows: when BTHA and 10 equivalents of GSH act, the grass green fluorescence at 507nm is quenched, and the blue fluorescence at 460nm appears; when BTHA and 10 equivalents of Cys act, grass green fluorescence quenching is generated at 507nm, and no new peak appears at 460 nm; when BTHA and 10 equivalents of Hcy act, the green fluorescence at 500nm is only weakened and not completely quenched, and no new peak appears at 460 nm.
The fluorescent probe can realize specific and visual detection on GSH, Cys and Hcy in a solution, and has no response to other amino acids, anions and metal cations.
A preparation method of an acryloyl compound using thiazole as a parent body as a fluorescent probe comprises the following steps:
step 1: synthesis of 2-hydroxy-3-methoxybenzothiazole (BTMT): dissolving 4.2mmol, 0.3ml of 2-aminothiophenol, 3.2mmol and 0.48g of o-vanillin in 10ml of ethanol, and adding 1.9ml of H with the mass fraction of 30%2O2Solutions andstirring the mixture at room temperature in 0.79ml of HCl solution with the mass fraction of 37 percent, quenching the reaction solution with water after the reaction is finished, and recrystallizing the reaction solution with ethanol after vacuum drying to obtain a bright yellow solid BTMT;
step 2: synthesis of 2, 3-dihydroxybenzothiazole (BTDH): BTMT adding BBr under ice bath3BTMT and BBr3The mass ratio is 2: 3, reacting for 1-2h under the protection of nitrogen, then reacting for 22-26h at room temperature, after the reaction is finished, quenching the reaction liquid with water to obtain a yellow solid, and performing column chromatography to obtain purified BTDH;
and step 3: 2-hydroxy-3-propenyl Benzothiazole (BTHA): dissolving 1mmol BTDH in 10ml dichloromethane, adding 1mmol triethylamine and 1mmol acryloyl chloride at 0 ℃, reacting for 1-2h, and reacting at room temperature overnight, wherein the mass ratio of the triethylamine, the acryloyl chloride and the BTDH is 1.1:1: 1;
and 4, step 4: and (3) post-reaction treatment: the reaction solution is extracted by dichloromethane, washed by water and then subjected to column chromatography to obtain pure BTHA.
The reaction time of the step 1 is 1-2 h.
The amount of water for quenching in the step 1 is 10-15 ml.
The amount of water for quenching in the step 2 is 10-15 ml.
Compared with the prior art, the invention has the beneficial effects that:
the fluorescent probe BTHA prepared by the invention only has a fluorescent peak at 507nm in a mixed solution of dimethyl sulfoxide, 4-hydroxyethyl piperazine ethanesulfonic acid (Hepes) buffer salt and DMSO, the fluorescent intensity at 507nm is continuously weakened after GSH is gradually added, a new fluorescent peak appears at 460nm, and the peak intensity is increased along with the addition of GSH, so that the GSH is proportionally detected, and the interference of background fluorescence is eliminated. The fluorescent probe can act with three amino acids GSH, Cys and Hcy in a solution, realizes specificity detection on the GSH, the Cys and the Hcy, generates different fluorescent signals, realizes high-selectivity distinguishing visualization detection on the GSH, the Cys and the Hcy, has no response to other amino acids, anions and metal cations, and has the characteristics of good selectivity and high sensitivity. The preparation method is simple and easy to synthesize.
Drawings
FIG. 1 is a graph of the change in fluorescence of probe BTHA when it was added to GSH at different concentrations (a) and its linear relationship (b).
FIG. 2 is a graph (a) showing the fluorescence change of probe BTHA with different concentrations of Cys and its linear relationship (b).
FIG. 3 is a graph (a) showing the fluorescence change of the probe BTHA at different concentrations of Hcy and a linear relationship (b) thereof.
FIG. 4 is a graph showing the change of fluorescence spectra with time of 100. mu.M Cys, GSH, and Hcy, respectively, added to BTHA as a probe.
FIG. 5 is a graph of fluorescence properties of probe BTHA as a function of pH.
FIG. 6 shows that probe BTHA was added with 100. mu.M biomolecule (blank, adenosine triphosphate, vitamin C, cysteine, homocysteine, glutamic acid, leucine, valine, histidine) and 100. mu.M GSH at lambda459/λ507Histogram of fluorescence intensity at ratio.
Detailed Description
The present invention will be described in further detail with reference to examples.
A preparation method of an acryloyl compound using thiazole as a parent body as a fluorescent probe comprises the following steps:
step 1: synthesis of 2-hydroxy-3-methoxybenzothiazole (BTMT): dissolving 4.2mmol, 0.3ml of 2-aminothiophenol, 3.2mmol and 0.48g of o-vanillin in 10ml of ethanol, and adding 1.9ml of H with the mass fraction of 30%2O2Stirring the solution and 0.79ml of HCl solution with the mass fraction of 37 percent at room temperature, reacting for 1-2h, quenching the reaction solution with water after the reaction is finished, wherein the water consumption for quenching is 10-15ml, and recrystallizing with ethanol after vacuum drying to obtain the bright yellow solid BTMT.
Step 2: synthesis of 2, 3-dihydroxybenzothiazole (BTDH): BTMT adding BBr under ice bath3BTMT and BBr3The mass ratio is 2: 3, reacting for 1-2h under the protection of nitrogen, then reacting for 22-26h at room temperature, after the reaction is finished, quenching the reaction liquid by water, wherein the water consumption for quenching is 10-15ml,obtain yellow solid, and obtain purified BTDH through column chromatography.
And step 3: 2-hydroxy-3-propenyl Benzothiazole (BTHA): dissolving 1mmol BTDH in 10ml dichloromethane, adding 1mmol triethylamine and 1mmol acryloyl chloride at 0 ℃, reacting for 1-2h, wherein the mass ratio of the triethylamine, the acryloyl chloride and the BTDH is 1.1:1:1, and then reacting at room temperature overnight.
And 4, step 4: and (3) post-reaction treatment: the reaction solution is extracted by dichloromethane, washed by water and then subjected to column chromatography to obtain pure BTHA.
The prepared probe BTHA nuclear magnetic resonance hydrogen spectrum and carbon spectrum data are as follows:
1HNMR(500MHz,CDCl3)δ7.99(d,J＝8.1Hz,1H),7.95(d,J＝8.0Hz,1H),7.66(d,J＝7.9Hz,1H),7.55(t,J＝7.7Hz,1H),7.47(t,J＝7.6Hz,1H),7.27(d,J＝7.9Hz,1H),7.02(t,J＝7.9Hz,1H),6.74(d,J＝17.3Hz,1H),6.48(dd,J＝17.3,10.5Hz,1H),6.12(d,J＝10.5Hz,1H).13C NMR(126MHz,CDCl3)δ168.74,163.95,151.57,150.21,139.53,132.90,132.68,127.50,126.89,125.83,125.73,122.25,121.59,119.09,118.22.
the reaction chemical equation is as follows:
performance test of the probe BTHA.
The synthesized probe BTHA was dissolved in an anhydrous acetonitrile solution to prepare a 5mM stock solution, and then diluted to a corresponding concentration with a mixed solution of Hepes (10mM) and DMSO (v/v ═ 9:1) for the test in the later stage.
(1) Sensitivity analysis for GSH response
The BTHA concentration of the probe was 1X 10-6M was added to a Hepes/DMSO mix (pH 7.4, v/v, 1:1) test system at lambda507Has strong fluorescence at lambda459No fluorescence is generated; as indicated by the arrows in FIG. 1(a) after addition of GSH, it can be seen that as the concentration of GSH increases, lambda507Gradual decrease in fluorescence intensity, λ459The fluorescence intensity is gradually enhanced, when the GSH concentration reaches 120 mu M, the fluorescence intensity is strongDegree tends to be stable, λ459/λ507The fluorescence ratio of (a) linearly varied with the concentration of GSH as shown in FIG. 1 (b).
(2) Cys response sensitivity assay
The BTHA concentration of the probe was 1X 10-6M was added to a Hepes/DMSO mix (pH 7.4, v/v, 1:1) test system at lambda507Has strong fluorescence at lambda459No fluorescence is generated; as indicated by the arrow in FIG. 2(a) after addition of Cys, it can be seen that as Cys concentration increases, lambda507Gradual decrease in fluorescence intensity, λ459No obvious change in fluorescence intensity; lambda when Cys concentration reached 120. mu.M507The fluorescence intensity is almost completely quenched, lambda459The intensity of fluorescence is increased slightly. Lambda [ alpha ]459/λ507The fluorescence ratio of (a) linearly varied with Cys concentration as shown in FIG. 2 (b).
(3) Sensitivity analysis for Hcy response
The BTHA concentration of the probe was 1X 10-6M was added to a Hepes/DMSO mix (pH 7.4, v/v, 1:1) test system at lambda507Has strong fluorescence at lambda459No fluorescence is generated; as indicated by the arrow in FIG. 3(a) after addition of Hcy, it can be seen that as the concentration of Hcy increases, lambda507Gradual decrease in fluorescence intensity, λ459No obvious change in fluorescence intensity; lambda when Cys concentration reached 100. mu.M507The fluorescence intensity is reduced to about half of the initial value, lambda459There was no increase in fluorescence intensity. Lambda [ alpha ]459/λ507The fluorescence ratio of (a) linearly varied with the Hcy concentration is shown in FIG. 3 (b).
(4) Study of kinetics of GSH/Cys/Hcy response
The BTHA concentration of the probe was 1X 10-6M was added to a Hepes/DMSO mix (pH 7.4, v/v, 1:1) test system at lambda507Has strong fluorescence at lambda459No fluorescence was observed. As shown in FIG. 4, the kinetics of the detection of these three amino acids by the BTHA probe was investigated, and in the above test system, after GSH, Cys and Hcy (c 100. mu.M) were added, respectively, lambda was measured459The fluorescence intensity of (A) was stabilized at about t 25 min.
(5) Acid-base stability of Probe BTHA
The BTHA concentration of the probe was 1X 10-6M is in different pH solutions, the pH stability is detected, and as can be seen from fig. 5, the fluorescence intensity of the probe is not greatly changed in a physiological environment pH range (pH is 6-8), and the test system is a ratio detection in a buffer solution, so that the probe can detect GSH, Cys and Hcy in the test system at high selectivity and high sensitivity without being influenced by pH.
(6) Assay for GSH detection selectivity
The BTHA concentration of the probe was 1X 10-6M various biomolecules were added to the test system, and it can be seen from FIG. 6 that only GSH was added, the probe was fluorescent (. lamda.)459/λ507) The enhancement is obvious. In addition, the left black solid bar of FIG. 6 shows that the concentration of the probe BTHA was 1X 10-6M is added with the fluorescence intensity of other biomolecules (blank control, adenosine triphosphate, vitamin C, cysteine, homocysteine, glutamic acid, leucine, valine and histidine), so that almost no fluorescence is observed, the fluorescence intensity of GSH is added into a right dotted line column, so that the fluorescence enhancement is obviously observed to be obviously enhanced, and the GSH has good selectivity.
In conclusion, the probe BTHA has better sensitivity and selectivity, GSH can be detected with high accuracy and high sensitivity by changing the ratio of fluorescence at 507nm and 460nm, and the GSH can be detected intuitively because the fluorescence color of the probe is changed from grass green to blue after the GSH is added. The probe can detect Cys and Hcy with high sensitivity and can detect common amino acids in the three organisms with high selectivity. The probe has simple synthesis method and convenient operation, and can be applied to the respective detection of GSH, Hcy and Cys in vitro.
Claims (8)
1. An acryloyl compound BTHA taking thiazole as a matrix is characterized in that the structural formula is as follows:
2. use of a compound according to claim 1 for the preparation of a probe for the selective, ratiometric detection of GSH in a mixed solution system of dimethylsulfoxide and Hepes.
3. The use according to claim 2, wherein the fluorescent probe BTHA, at 5 μmol/L, is capable of detecting GSH at a volume/volume ratio of 9:1 in Hepes and DMSO of 10mmol/L, said GSH being in the range of 5-60 μmol/L.
4. The use of claim 2, wherein the fluorescent probe reacts with GSH, Cys and Hcy at room temperature, and the difference of the fluorescent properties is obvious, and the specific phenomenon is as follows: when BTHA and 10 equivalents of GSH act, the grass green fluorescence at 507nm is quenched, and the blue fluorescence at 460nm appears; when BTHA and 10 equivalents of Cys act, grass green fluorescence quenching is generated at 507nm, and no new peak appears at 460 nm; when BTHA and 10 equivalents of Hcy act, the green fluorescence at 500nm is only weakened and not completely quenched, and no new peak appears at 460 nm.
5. The method for preparing the thiazole-based acryloyl ester compound BTHA according to claim 1, comprising the following steps:
step 1: synthesis of (2-2 '-hydroxy-3' -methoxyphenyl) benzothiazole BTMT: dissolving 4.2mmol, 0.3ml of 2-aminothiophenol, 3.2mmol and 0.48g of o-vanillin in 10ml of ethanol, and adding 1.9ml of H with the mass fraction of 30%2O2Stirring the solution and 0.79ml of HCl solution with the mass fraction of 37% at room temperature, after the reaction is finished, quenching the reaction solution by using water, and recrystallizing by using ethanol after vacuum drying to obtain a bright yellow solid BTMT;
step 2: synthesis of 2- (2 ', 3' -dihydroxyphenyl) benzothiazole BTDH: adding BBr3 into BTMT under ice bath, wherein the mass ratio of BTMT to BBr3 is 2: 3, reacting for 1-2h under the protection of nitrogen, then reacting for 22-26h at room temperature, after the reaction is finished, quenching the reaction liquid with water to obtain a yellow solid, and performing column chromatography to obtain purified BTDH;
and step 3: 2-hydroxy-3-propenyl benzothiazole BTHA: dissolving 1mmol BTDH in 10ml dichloromethane, adding 1mmol triethylamine and 1mmol acryloyl chloride at 0 ℃, reacting for 1-2h at the mass ratio of the triethylamine to the acryloyl chloride to the BTDH of 1:1:1, and reacting at room temperature overnight;
and 4, step 4: and (3) post-reaction treatment: the reaction solution is extracted by dichloromethane, washed by water and then subjected to column chromatography to obtain pure BTHA.
6. The method for preparing the thiazole-based acryloyl ester compound BTHA according to claim 5, wherein the reaction time of the step 1 is 1-2 h.
7. The method for preparing the thiazole as the parent acryloyl ester compound BTHA according to claim 5, wherein the amount of water used for quenching in the step 1 is 10-15 mL.
8. The method for preparing the thiazole-based acryloyl ester compound BTHA according to claim 5, wherein the amount of water used for quenching in the step 2 is 10-15 ml.
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| CN108623533A (en) * | 2018-07-13 | 2018-10-09 | 济南大学 | A kind of fluorescence probe for detecting cysteine and application based on thiazole |
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| WO2013019978A1 (en) * | 2011-08-03 | 2013-02-07 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Portland State University | Fluorescence detection of cysteine and homocysteine |
| EP2719703A1 (en) * | 2012-10-12 | 2014-04-16 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Precursor molecule for the synthesis of D-luciferin |
| CN108623533A (en) * | 2018-07-13 | 2018-10-09 | 济南大学 | A kind of fluorescence probe for detecting cysteine and application based on thiazole |
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