CN111116511A - Benzothiazole biological thiol probe and preparation method and application thereof - Google Patents
Benzothiazole biological thiol probe and preparation method and application thereof Download PDFInfo
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- CN111116511A CN111116511A CN202010008193.0A CN202010008193A CN111116511A CN 111116511 A CN111116511 A CN 111116511A CN 202010008193 A CN202010008193 A CN 202010008193A CN 111116511 A CN111116511 A CN 111116511A
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- 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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- G01N21/62—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
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- 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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Abstract
The invention discloses a benzothiazole biological thiol probe with a biological thiol detection function, which is shown in a formula (I):
wherein R is hydrogen, alkyl or alkoxy. The probe of the invention has good fluorescence performance and simple synthesis, obviously enhances the fluorescence of the probe after reacting with mercaptan, shows good selectivity to the mercaptan, and can be used as a biological mercaptan fluorescent probe. In addition, the raw materials for preparing the probe are cheap and easy to obtain, the cost is low, the preparation process is simple, and the method is suitable for large-scale industrial popularization and application.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a benzothiazole biological thiol probe as well as a preparation method and application thereof.
Background
Biological thiols are mainly Glutathione (GSH), cysteine (Cys) and homocysteine (Hcy), which play a crucial role in the growth, metabolism and maintenance of the intracellular redox balance. At the same time, abnormal levels of biological thiols are closely associated with many diseases. For example, abnormalities in GSH levels are closely associated with leukocyte loss, cancer, and the like; high concentrations of Cys in an organism can lead to neurotoxicity, while low concentrations of Cys can lead to lethargy, hair loss, liver damage, etc.; high concentration Hcy in human blood is related to cardiovascular diseases and Alzheimer's disease; therefore, in order to further understand the role of thiols in biology, real-time detailed monitoring of these thiols is very necessary, which is very important for the research of related diseases.
Fluorescence imaging technology is an important research means in the biomedical field and is widely applied to imaging of molecules, cells, tissues and other different levels. The method has the advantages of good repeatability, real-time imaging and the like, and realizes in-situ real-time monitoring on target molecules. The organic small molecule fluorescent probe has become an important tool of the fluorescence imaging technology due to the characteristics of rapidness, high selectivity, good biocompatibility and the like. Many of the reported organic small molecule fluorescent probes need further improvement in photophysical or photochemical properties, and therefore, it is necessary to construct a novel fluorescent probe having excellent photophysical and photochemical properties.
Disclosure of Invention
The invention mainly aims to overcome the defects of the prior art and provide a benzothiazole fluorescent probe with biological thiol detection capability.
In order to achieve the purpose, the invention is realized by the following technical scheme:
a benzothiazole biological thiol probe has a structural general formula shown in formula (I):
in the formula (I), R is hydrogen, alkyl or alkoxy.
The benzothiazole biological thiol probe provided by the invention has larger Stokes displacement, can reduce the influence of background exciting light on fluorescence measurement, can avoid self-quenching phenomenon, and is beneficial to increasing the sensitivity of the probe and the detection reliability.
Preferably, R is alkoxy or alkyl of 1-6C.
More preferably, R is methoxy, i.e., the benzothiazole biolhiol probe is 2- (benzo [ d ] thiazol-2-yl) -6-methoxyphenyl-2, 4-dinitrobenzenesulfonate.
Another object of the present invention is to provide a method for preparing the above-mentioned benzothiazole type bio-thiol probe, in order to increase biocompatibility and strong fluorescence, the present invention first generates the corresponding 2- (benzo [ d ] thiazol-2-yl) -6-R-phenol by reacting 2-aminothiophenol with 3-R-2-hydroxybenzaldehyde; then the reaction is carried out on the triethylamine which is weak base and 2, 4-dinitrobenzene sulfonyl chloride, thus obtaining the target compound. The method comprises the following steps:
a. dissolving 2- (2-hydroxyphenyl) -3-R-group benzothiazole, triethylamine and 2, 4-dinitrobenzenesulfonyl chloride in a first solvent, and reacting at room temperature to obtain a reaction mixed solution; the R group is hydrogen, alkyl or alkoxy;
b. and adding the reaction mixed solution into a second solvent, washing, extracting, drying an organic layer by using anhydrous sodium sulfate, filtering and purifying to obtain a light yellow solid, namely the benzothiazole biological thiol probe.
The benzothiazole biological thiol probe is simple to synthesize, low in cost, strong in modifiability and wide in application prospect.
Preferably, the first solvent is dichloromethane or tetrahydrofuran, and the second solvent is water.
Preferably, the room temperature reaction time of step a is 12 hours.
Preferably, the 2- (2-hydroxyphenyl) -3-R-group benzothiazole: triethylamine: the mass ratio of 2, 4-dinitrobenzenesulfonyl chloride was 1:3: 2.
Preferably, the purification is to obtain a crude product through reduced pressure distillation, then perform column chromatography separation by using petroleum ether/ethyl acetate as a mobile phase, and perform reduced pressure distillation to obtain a light yellow solid, wherein the petroleum ether/ethyl acetate is 5-10/1 (v/v).
Preferably, the 2- (2-hydroxyphenyl) -3-R-aminobenzothiazole is 2- (2-hydroxyphenyl) -3-methoxybenzothiazole, the 2- (2-hydroxyphenyl) -3-methoxybenzothiazole and triethylamine are dissolved in a first solvent, and then the first solvent solution of the 2, 4-dinitrobenzenesulfonyl chloride is dropwise added into the first solvent solution of the 2- (2-hydroxyphenyl) -3-methoxybenzothiazole and triethylamine; the first solvent is dichloromethane.
The invention also aims to provide the application of the benzothiazole biological thiol probe in the detection of biological thiol.
Specifically, the application of the benzothiazole biological thiol probe in preparing a biological thiol detection probe and the application in preparing a thiol imaging reagent are provided.
The invention has the beneficial effects that:
compared with the prior art, the benzothiazole biological thiol probe has the following advantages:
1. the probe can selectively respond to the fluorescence of the biological thiol, provides a simple, effective and intuitive means for the monitoring and research of the biological thiol, and can be widely applied to the detection and imaging of the biological thiol;
2. the probe of the invention has the characteristics of easy synthesis, good fluorescence performance and high selectivity;
3. the preparation method has the advantages of cheap and easily-obtained raw materials, low cost and simple preparation process, and is suitable for large-scale industrial popularization and application.
Drawings
FIG. 1 is a graph showing changes in fluorescence intensity of reaction of Compound 1 of example 3 with Cys, GSH, Hcy and other amino acids;
FIG. 2 shows the addition of H to Compound 1 of example 32(ii) a plot of the change in fluorescence intensity after S;
FIG. 3 is a graph showing changes in fluorescence intensity of reaction of Compound 2 of example 4 with Cys, GSH, Hcy and other amino acids;
FIG. 4 shows the addition of H to Compound 2 of example 42Graph of change in fluorescence intensity after S.
Detailed Description
The invention is further described with reference to the drawings and the following detailed description, which are not intended to limit the invention in any way. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated. Unless otherwise indicated, reagents and materials used in the present invention are commercially available.
Example 1
2- (2-hydroxyphenyl) -3-methoxybenzothiazole (0.5mmol, 0.130g) and triethylamine (1.5mmol, 0.15g) were dissolved in 10mL of CH2Cl2And placed in a reaction flask, and 0.226g (1mmol) of 2, 4-dinitrobenzenesulfonyl chloride was dissolved in 5mL of CH2Cl2Slowly dripping acyl chloride solution into a reaction bottle at room temperature. And after the reaction of the reactants is completed, washing the reactant by using 30mL of distilled water, drying an organic layer by using anhydrous sodium sulfate, filtering and carrying out rotary evaporation to obtain a crude product. TLC purification (petroleum ether: ethyl acetate ═ 10:1) gave a pale yellow solid, i.e., the target product 3- (2-benzothiazolyl) -2-phenyl-2, 4-dinitrobenzenesulfonate (compound 1), yield: 50.26 percent.
1H NMR(500MHz,CDCl3),δ9.05(d,J＝2.5Hz,1H),8.69(dd,J＝8.6,2.5Hz,1H),7.89(d,J＝8.1Hz,1H),7.82(d,J＝8.6Hz,1H),7.42(dd,J＝11.3,4.0Hz,1H),7.34–7.29(m,1H),6.97(d,J＝8.1Hz,1H),6.92–6.87(m,1H),6.60(t,J＝8.1Hz,1H),6.38(dd,J＝8.2,1.2Hz,1H),3.92(s,3H)。
Example 2
2- (2-hydroxyphenyl) benzothiazole (0.5mmol, 0.113g) and triethylamine (1.5mmol, 0.15g) were dissolved in 10mL CH2Cl2And placed in a reaction flask, and 2, 4-dinitrobenzenesulfonyl chloride (1mmol, 0.226g) was dissolved in 5mL of CH2Cl2Slowly dripping acyl chloride solution into a reaction bottle at room temperature. And after the reaction of the reactants is completed, washing the reactant by using 30mL of distilled water, drying an organic layer by using anhydrous sodium sulfate, filtering and carrying out rotary evaporation to obtain a crude product. TLC purification (petroleum ether: ethyl acetate ═ 10:1) gave a pale yellow solid, i.e., the target product 3- (2-benzothiazolyl) -2-phenyl-2, 4-dinitrobenzenesulfonate (compound 2), yield: 55.43 percent.
1H NMR(500MHz,CDCl3),δ8.85–8.77(m,1H),8.30–8.24(m,1H),7.96(dd,J＝4.4,3.1Hz,1H),7.94–7.90(m,1H),7.81(d,J＝1.3Hz,1H),7.65(dd,J＝16.8,5.6Hz,1H),7.58(dd,J＝17.1,5.6Hz,1H),7.21–7.13(m,1H),7.03(t,J＝7.3Hz,1H),6.91(td,J＝7.4,2.5Hz,1H),6.25–6.15(m,1H)。
Example 3
To 10mM PBS buffer at pH 7.4 at room temperature, 20 μ M of compound 1 of example 1 was added, followed by 20 μ M of Cys, GSH, and Hcy, respectively, and fluorescence spectra were recorded at different times, as shown in fig. 1, where a) is a time graph of the reaction of compound 1 with Cys; B) is a time plot of compound 1 reacted with GSH; C) the time course of the reaction of compound 1 with Hcy is shown. As can be seen in FIG. 1, fluorescence increased significantly at 480nm with time; the compound 1 can be used as a ratiometric fluorescent probe of the biological thiol, so that the quantitative detection of the biological thiol is realized. After incubating compound 1 at 20. mu.M with 1mM of arginine (Arg), phenylalanine (Phe), lysine (Lys), methionine (Met), aspartic acid (Asp), leucine (Leu), threonine (Thr), alanine (Ala) and tyrosine (Tyr) for 120 minutes, the corresponding fluorescence spectra were recorded, and the fluorescence intensity at 480nm was compared with the fluorescence intensity at 480nm after incubating GSH, Cys and Hcy at 10. mu.M for 90 minutes, and D) in FIG. 1 is the fluorescence response of compound 1 to different amino acids.
FIG. 2 shows the addition of Compound 1 to H2(ii) fluorescence change profile after S; in the presence of H2After S, the fluorescence intensity of the compound 1 solution is obviously improved under the irradiation of ultraviolet light.
Example 4
To 10mM PBS buffer pH 7.4 at room temperature, 20 μ M of compound 2 of example 2 was added, followed by 20 μ M of Cys, GSH, and Hcy, respectively, and fluorescence spectra were recorded at different times. As shown in FIG. 3, A) is a time-varying graph of the reaction of Compound 2 with Cys; B) is a time plot of compound 2 reacted with GSH; C) the time course of the reaction of Compound 2 with Hcy is shown. As can be seen in FIG. 3, the fluorescence increased significantly at 480nm with increasing time; the compound 2 can be used as a ratiometric fluorescent probe of the biological thiol, so that the quantitative detection of the biological thiol is realized. After incubating compound 2 at 20. mu.M with 1mM arginine (Arg), phenylalanine (Phe), lysine (Lys), methionine (Met), aspartic acid (Asp), leucine (Leu), threonine (Thr), alanine (Ala), tyrosine (Tyr) for 120 minutes, the corresponding fluorescence spectra were recorded, and the fluorescence intensity at 480nm was compared with the fluorescence intensity at 480nm after incubating GSH, Cys, Hcy at 10. mu.M for 90 minutes, D) in FIG. 3 is the fluorescence response of compound 2 to different amino acids.
FIG. 4 shows the addition of Compound 2 to H2(ii) fluorescence change profile after S; in the presence of H2After S, the fluorescence intensity of the compound 2 solution is obviously improved under the irradiation of ultraviolet light.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (9)
1. A benzothiazole biological thiol probe has a structural general formula shown in formula (I):
in the formula (I), R is hydrogen, alkyl or alkoxy.
2. A benzothiazole biolhiol probe according to claim 1, wherein: r is alkoxy or alkyl of 1-6C.
3. A benzothiazole biolhiol probe according to claim 1, wherein: r is methoxy.
4. A method for preparing the benzothiazole bio-thiol probe of claim 1, comprising the steps of:
a. dissolving 2- (2-hydroxyphenyl) -3-R-group benzothiazole, triethylamine and 2, 4-dinitrobenzenesulfonyl chloride in a first solvent, and reacting at room temperature to obtain a reaction mixed solution; the R group is hydrogen, alkyl or alkoxy;
b. and adding the reaction mixed solution into a second solvent, washing, extracting, drying an organic layer by using anhydrous sodium sulfate, filtering and purifying to obtain a light yellow solid, namely the benzothiazole biological thiol probe.
5. The method for preparing a benzothiazole bio-thiol probe according to claim 4, wherein: the first solvent is dichloromethane or tetrahydrofuran, and the second solvent is water.
6. The method for preparing a benzothiazole bio-thiol probe according to claim 4, wherein: the 2- (2-hydroxyphenyl) -3-R-group benzothiazole: triethylamine: the mass ratio of 2, 4-dinitrobenzenesulfonyl chloride was 1:3: 2.
7. The method for preparing a benzothiazole bio-thiol probe according to claim 4, wherein: the purification is to obtain a crude product through reduced pressure distillation, then carry out column chromatography separation by taking petroleum ether/ethyl acetate as a mobile phase, and obtain a light yellow solid through reduced pressure distillation.
8. The method for preparing a benzothiazole bio-thiol probe according to claim 4, wherein: the 2- (2-hydroxyphenyl) -3-R-aminobenzothiazole is 2- (2-hydroxyphenyl) -3-methoxybenzothiazole, the 2- (2-hydroxyphenyl) -3-methoxybenzothiazole and triethylamine are dissolved in a first solvent, and then the first solvent solution of the 2, 4-dinitrobenzenesulfonyl chloride is dropwise added into the first solvent solution of the 2- (2-hydroxyphenyl) -3-methoxybenzothiazole and triethylamine; the first solvent is dichloromethane.
9. Use of the benzothiazole biolhiol probe of claim 1 in biological thiol detection and imaging.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114591264A (en) * | 2020-12-04 | 2022-06-07 | 湖南超亟检测技术有限责任公司 | Fluorescent probe for indicating pH value and preparation method and application thereof |
| CN116120257A (en) * | 2022-12-12 | 2023-05-16 | 渤海大学 | Fluorescent probe for indicating freshness of large yellow croaker as well as preparation method and application thereof |
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| CN107721922A (en) * | 2017-10-24 | 2018-02-23 | 贺州学院 | A kind of novel quinoline class biological thiol fluorescence probe and its preparation and application |
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2020
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| CN107602502A (en) * | 2017-09-29 | 2018-01-19 | 安徽农业大学 | A kind of ESIPT types fluorescence probe and application for biological thiol detection |
| CN107721922A (en) * | 2017-10-24 | 2018-02-23 | 贺州学院 | A kind of novel quinoline class biological thiol fluorescence probe and its preparation and application |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114591264A (en) * | 2020-12-04 | 2022-06-07 | 湖南超亟检测技术有限责任公司 | Fluorescent probe for indicating pH value and preparation method and application thereof |
| CN116120257A (en) * | 2022-12-12 | 2023-05-16 | 渤海大学 | Fluorescent probe for indicating freshness of large yellow croaker as well as preparation method and application thereof |
| CN116120257B (en) * | 2022-12-12 | 2024-04-30 | 渤海大学 | Fluorescent probe for indicating freshness of large yellow croaker as well as preparation method and application thereof |
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