CN117510433A - Benzothiazole organic compound and application thereof - Google Patents

Benzothiazole organic compound and application thereof Download PDF

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CN117510433A
CN117510433A CN202311471084.2A CN202311471084A CN117510433A CN 117510433 A CN117510433 A CN 117510433A CN 202311471084 A CN202311471084 A CN 202311471084A CN 117510433 A CN117510433 A CN 117510433A
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solution
organic compound
benzothiazole
compound
value
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魏蒙蒙
杨锐
张慧国
韩志达
杨希峰
郝明辉
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Changshu Institute of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • 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"
    • G—PHYSICS
    • 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
    • G01N21/645—Specially adapted constructive features of fluorimeters
    • G01N21/6456—Spatial resolved fluorescence measurements; Imaging
    • G—PHYSICS
    • 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
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
    • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
    • G01N21/80—Indicating pH value
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur

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  • Health & Medical Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Optics & Photonics (AREA)
  • Plasma & Fusion (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

The invention discloses a benzothiazole organic compound and application thereof, in particular to application of observing pH of a solution and detecting RNA under single excitation light. The chemical name of the compound is: (E) -2- (3-chloro-4-hydroxy-5-methoxystyryl) -3-methylbenzothiazole-3-iodonium salt. The organic compound has pH response characteristic, and can realize the detection of the pH value of the solution under the excitation of single excitation light. Therefore, the organic compound can be used for detecting the pH value of sewage and the biological pH value microenvironment. The compounds of the invention may also be used to detect RNA. Since the tumor microenvironment is closely related to the pH value and RNA, the compound can be used for preparing a tumor diagnosis reagent and a fluorescence imaging reagent or a radioactive imaging reagent for tumors.

Description

Benzothiazole organic compound and application thereof
Technical Field
The invention belongs to the technical field of chemical medicines, and particularly relates to a benzothiazole organic compound and application thereof.
Background
The pH value is an important index in the field of chemical industrial production, and reflects the physical quantity of the acidity and alkalinity of the solution and reflects the hydrogen ion (H + ) Is a concentration of (3). Detecting the pH of the solution allows for determination of the chemical nature of the solution, better control and regulation of the chemical reaction. The pH value can also reflect the change of microenvironment in cells, and is indistinguishable from biomolecular interactions, metabolite diffusion and signal transduction. In laboratory research and industrial production, the pH of the solution is an important quality control parameter. Thus, detecting changes in pH is of great chemical and biological importance.
At present, methods for detecting the pH value mainly comprise pH test paper, a pH meter and the like, the liquid amount required by the methods is large, and the solution is required to be in direct contact with a testing instrument, so that the pollution of the testing instrument is caused, and the change of the pH value in cells cannot be detected.
Along with the development of technology, the fluorescence method is an important method for detecting the pH of a solution and cells due to the advantages of high sensitivity, rapid response and the like. The current fluorescent probe generally detects the change of the pH value of the solution through the change of the fluorescent intensity, but the detection sensitivity of the method is not high and is easily influenced by instrument errors. The ratio type fluorescent probe can offset the influence of instrument errors through the ratio of the fluorescent intensity, and the detection accuracy is improved. When the current ratio type fluorescent probe detects the fluorescence intensity, two kinds of excitation light are needed to excite, which is easy to cause complex operation, more importantly, the excitation light is increased, the fluorescent probe is damaged by fluorescence, and fluorescence quenching is generated.
Therefore, a fluorescent compound with higher pH sensitivity needs to be designed, and under the excitation of single excitation light, the photodamage to the organic fluorescent compound is reduced by a fluorescence intensity ratio method, so that the high-sensitivity detection of the pH value of the solution is realized.
Disclosure of Invention
The invention aims to: the invention aims to provide benzothiazole organic compounds and application thereof, in particular to application of observing pH of a solution and detecting RNA under single excitation light. Since the pH and RNA in cells are associated with various diseases (cancer, etc.), the multipurpose organic compound of the present invention can be used for preparing a pH-sensitive tumor diagnostic reagent, a fluorescent imaging reagent or a radioactive imaging reagent for tumors.
The technical scheme is as follows: the aim of the invention is achieved by the following technical scheme:
the invention provides a benzothiazole organic compound, which has the chemical name: (E) -2- (3-chloro-4-hydroxy-5-methoxystyryl) -3-methylbenzothiazole-3-iodonium salt; the structural formula is as follows:
the invention also provides application of the benzothiazole organic compound in observing the pH of a solution under the excitation of single excitation light.
The compound can roughly detect the pH value of the solution under the condition of visible light.
The compound can accurately measure the pH value of the solution under a fluorescence photometer or a fluorescence spectrometer.
In a preferred embodiment of the present invention, the compound is added to the test solution by detecting the fluorescence intensity I of the solution F Then according to the equation log [ (1.5-I)/(I-0.07)]pH-5 to calculate the pH of the solution.
The pH of the solution is in the range of 3.0-9.0.
The concentration of the compound in the solution is 5-15. Mu.M. I.e.the concentration of stained cells of the compound is 5-15. Mu.M. When the concentration is measured, the concentration measuring solution has lower aggregation quenching effect and better measuring effect.
Further, the concentration of the compound in the solution was 10. Mu.M.
The benzothiazole organic compound can be used for detecting the pH value of sewage and the biological pH value microenvironment.
The invention also provides a method for detecting the pH of the solution by using the benzothiazole organic compound, which comprises the following steps:
(1) Adding the benzothiazole organic compound into a solution to be detected;
(2) Exciting under 470nm single excitation light by using fluorescence intensity detection equipment to obtain a fluorescence intensity ratio I of the solution at 530nm and 590nm;
(3) The pH of the mixed solution was directly calculated according to the equation log [ (1.5-I)/(I-0.07) ]=ph-5.
When the pH value of the solution is detected, the existing fluorescent probe is usually prepared by putting a fluorescent compound into a cuvette, exciting the fluorescent compound by light with excitation light of 405nm, and obtaining a corresponding spectrum 1 by a fluorescent spectrometer; then placing the sample into an instrument, and exciting the sample by using 543nm light to obtain a fluorescence spectrum 2 under the excitation of 543nm excitation light; two spectrum files are opened respectively, fluorescence intensity values in spectrum 1 and spectrum 2 are read, and then the fluorescence intensity ratio of the fluorescent compound at 550nm in spectrum 1 and 605nm in spectrum 2 is calculated. Finally, the pH value of the solution is calculated according to the obtained fluorescence intensity ratio.
The detection method provided by the invention directly uses 470nm single excitation light to excite, so as to obtain a corresponding spectrum, reads the fluorescence intensity value in the spectrum, and directly calculates the pH value of the solution. The benzothiazole organic compound can measure the pH value of a solution under the excitation of a single excitation light, and the existing detection method can measure the pH value only by respectively exciting two excitation lights. It can be seen that the use of the compounds of the present invention for measuring pH is simple to operate and, more importantly, reduces photodamage to the probe due to the reduced number of excitations.
The inventors further explored the use of said benzothiazole organic compounds, and found that they can be used for the detection of RNA. RNA is significant in meaning in cell life activities, and has important functions in the processes of transmission of genetic information, protein synthesis and the like. RNA is also closely related to some diseases, and thus, in vitro detection of RNA is of great importance.
Therefore, the invention also provides application of the benzothiazole organic compound in RNA detection.
The invention also provides application of the benzothiazole organic compound in preparation of RNA detection reagent.
The invention also provides application of the benzothiazole organic compound in preparing tumor diagnostic reagents, fluorescent imaging reagents or radioactive imaging reagents for tumors.
The concentration of the compound stained cells is 1-15 mu M. The concentration is dyed, the cytotoxicity is low, and the imaging effect is good.
The beneficial effects are that:
(1) The organic compound of the invention leads the molecule to have good optical performance by introducing cation structures such as benzothiazole and the like. By introducing a pH-sensitive phenolic hydroxyl group, the organic compound may give a higher sensitivity to pH. Due to the introduction of the cation salt, the fluorescence spectrum of the organic compound is red shifted, and the optical performance is excellent.
(2) Meanwhile, the benzothiazole organic compound can measure the pH value of the solution under the excitation of single excitation light. Therefore, when the compound is used for measuring the pH value, the operation is simple, and more importantly, the photodamage of the probe can be reduced due to the reduction of the excitation times. Therefore, the compound disclosed by the invention can be used for detecting the pH value of sewage and the biological pH value microenvironment.
(3) Since the pH value and RNA in cells are associated with various diseases (cancers and the like), the organic compounds of the present invention can be used for preparing RNA detection reagents, for preparing tumor diagnosis reagents, for preparing fluorescent imaging reagents or radioactive imaging reagents for tumors.
Drawings
FIG. 1 is an absorption spectrum of TBCL (10. Mu.M) in various solvents.
FIG. 2 shows the absorption spectra and pictures of TBCL (10. Mu.M) in solutions of different pH concentrations; wherein, FIG. 2 (A) is the absorption spectrum of TBCL (10. Mu.M) in solutions of different concentrations of pH; FIG. 2 (B) is a photograph of TBCL (10. Mu.M) in solutions of varying concentrations of pH.
FIG. 3 shows fluorescence spectra of TBCL (10. Mu.M) in pH solutions of different concentrations and a fitted curve; wherein, FIG. 3 (A) is a fluorescence spectrum of TBCL (10. Mu.M) in pH solutions of different concentrations; FIG. 3 (B) is a fitted curve of TBCL (10. Mu.M) at different pH values.
FIG. 4 shows fluorescence spectra of TBCL (10. Mu.M) in RNA solutions of different concentrations and a fitted curve; FIG. 4 (A) shows the absorbance spectrum in tris buffer with or without RNA in TBCL (10. Mu.M); FIG. 4 (B) is a fluorescence spectrum of TBCL (10. Mu.M) in RNA solutions of different concentrations; FIG. 4 (C) is a graph showing the fluorescence intensity of TBCL (10. Mu.M) at 570nm in RNA solutions of different concentrations; FIG. 4 (D) is a plot of TBCL (10. Mu.M) fit in RNA solutions of different concentrations.
Detailed Description
The technical scheme of the present invention is described in detail below through specific examples, but the scope of the present invention is not limited to the examples.
The materials in each example were from commercial products.
The test instrument of the absorption spectrum is a Hitachi U-2910 spectrophotometer; the fluorescence spectrometer is a Hitachi F-2700 spectrophotometer.
EXAMPLE 1 Synthesis of benzothiazole organic Compound (TBCL for short)
Wherein the substituent R is alkyl. In this embodiment, R is selected from methyl.
Benzothiazolium iodide (0.2915 g,1 mmol) and 3-chloro-4-hydroxy-5-methoxybenzaldehyde (0.186 g,1 mmol) were dissolved in 20mL of methanol and stirred in a flask for 1h. After stirring, a few drops of piperidine were added, refluxed at 85 ℃ for 8h, cooled to room temperature and washed with petroleum ether. By CH 2 Cl 2 And CH (CH) 3 OH mixture (CH) 2 Cl 2 And CH (CH) 3 OH with the volume ratio of 10:1-6:1) as eluent, and performing column chromatography separation and purification to obtain 0.16g of red solid, wherein the chemical name is: (E) -2- (3-chloro-4-hydroxy-5-methoxystyryl) -3-methylbenzothiazole-3-iodized salt, namely organic compound molecule, is called as short termTBCL。
The structure of the above-mentioned compound was confirmed by analyzing the hydrogen spectrum and carbon spectrum of the compound. The characterization results are as follows:
1 H NMR(400MHz,DMSO-d 6 )δ(ppm):8.33(d,J＝8.0Hz,1H),8.11(d,J＝8.0Hz,1H),8.0(d,J＝16.0Hz,1H),7.78-7.82(m,2H),7.68-7.72(m,2H),7.55(s,1H),4.26(s,3H),3.92(s,3H).
13 C NMR(400MHz,DMSO-d 6 ),δ(ppm):170.82,150.03,148.21,142.51,129.45,127.99,127.50,126.83,126.78,124.39,124.27,121.91,116.45,111.33,109.22,56.90,36.26。C 17 H 15 ClINO 2 S。
example 2 photophysical Property test experiments of organic Compound TBCL in different solvents
Test solutions containing 10. Mu.M TBCL were prepared using different types of organic solvents (see FIG. 1 for organic solvents), and the absorption spectra of the above solutions were measured using an ultraviolet spectrophotometer, and the results are shown in FIG. 1.
As can be seen from fig. 1: the organic compound TBCL has a large absorbance value at 350-600nm and two fluorescence peaks at 350-600nm, which indicates that the fluorescent compound can be excited by 350-600nm light, and the optimal excitation wavelengths are 405nm and 530nm.
Example 3 fluorescence test experiment of organic Compound TBCL in solutions of different pH values
The organic compound stock solution was prepared at a concentration of 1mM in DMSO. The PBS solution was adjusted to pH with hydrochloric acid and NaOH to prepare solvents of different pH (ph=3, 4, 5, 6, 7, 8, 9), and then TBCL was added to prepare test solutions containing 10 μm TBCL, respectively.
The absorption spectrum of the above solution was measured by an ultraviolet spectrophotometer, see fig. 2. The fluorescence emission spectrum is tested by a fluorescence spectrometer, and the fluorescence spectrum is fitted to obtain a corresponding curve, see fig. 3.
In FIG. 2, two absorption peaks appear in solutions with different pH values, respectively, the absorption peak at about 400nm gradually decreases and the absorption peak at about 530nm gradually increases with the increase of the pH value, which indicates that the organic compound can observe the change of the pH value of the solution through ultraviolet absorption spectrum. As can be seen from the photographed physical picture, the color of the small organic molecular compound gradually changes from yellow to red as the pH value increases. Further illustrating that the organic compound may observe the pH of the solution.
Because of the greater degree of conjugation of the structure of the compound, a significant response to fluorescence may be generated. Thus, we tested the fluorescence spectra of the probe at different pH values. As can be seen from fig. 3, when excited with a single excitation light, two fluorescence peaks appear, namely 530nm and 590nm; as the pH value increases, the fluorescence intensity at 530nm decreases, and the fluorescence intensity at 590nm does not change.
To further verify that the organic compounds can quantify the pH of the solution, the fluorescence intensities of the organic compounds at 530 and 590nm were measured, and as can be seen from fig. 3 (B), the ratio of the two was reduced, and the fitted curve was log [ (1.5-I)/(I-0.07) ]=ph-5, indicating that the probe can measure the pH of the solution.
Example 4 organic Compound TBCL detection solution pH
The method comprises the following steps:
(1) Adding TBCL into the solution to be detected, so that the concentration of the TBCL in the solution is 10 mu M;
(2) Exciting under 470nm single excitation light by using a fluorescence photometer to obtain a fluorescence intensity ratio I of the solution at 530nm and 590nm;
(3) The pH of the mixed solution was directly calculated according to the equation log [ (1.5-I)/(I-0.07) ]=ph-5.
The pH value of the solution to be measured is detected to be 6.08 by a pH meter, and the pH value is calculated to be 5.98 by the method of the embodiment. The method is reliable and has high sensitivity.
Comparative example 1 the inventors previously disclosed a compound having the structural formula:
the compound needs to be excited by two kinds of excitation light when detecting the pH of the solution. The specific method comprises the following steps:
placing the compound into a cuvette, exciting with light with excitation light of 405nm, obtaining a corresponding spectrum 1 by using a fluorescence spectrometer, then placing the compound into the instrument, and exciting with light of 543nm to obtain a fluorescence spectrum 2 under excitation of the excitation light of 543 nm; two spectral files are opened respectively, and then the fluorescence intensity ratio I of the compound in the solution to be tested in the spectrum 1 at 550nm and in the spectrum 2 at 605nm is calculated, and then the formula (log [ (Imax-I)/(I-Imin) ]=pH-pKa is carried out, and the pH value is calculated, wherein pKa=5.87, and Imax and Imin are the maximum value and the minimum value of the ratio in a fitting curve obtained by measuring the known solution.
By comparison with the method of the present invention, it can be known that: when the method is used for measuring the pH value, the operation is simple, and more importantly, the photodamage of the probe can be reduced due to the reduction of the excitation times.
Example 5 fluorescence test experiment of organic Compound TBCL in RNA solutions of different concentrations
The organic compound stock solution was prepared at a concentration of 1mM in DMSO. Different concentrations (0,100,200,300,400,500,600,700,800,1000,1200,1400,1600,1800,2000,2200,2400,2600,2800,3000,3200,3400,3600,3800,4000. Mu.M) of RNA (from calf thymus RNA) were dissolved in tris buffer and then TBCL was added separately to make a test solution containing 10. Mu.M TBCL. The above solutions were measured for absorption and fluorescence spectra with an ultraviolet-visible spectrophotometer and a fluorescence spectrometer, respectively. The results are shown in FIG. 4.
As can be seen from fig. 4 (a): when RNA was added, the compounds had absorption at 420-660nm, indicating that this range of light excitation was possible. FIG. 4 (B) shows fluorescence spectra of compound TBCL in solutions of RNAs of different concentrations, wherein the concentration of RNAs increases from bottom to top, and the fluorescence intensity increases gradually as the concentration of RNAs increases. FIG. 4 (C) is a fluorescence curve of the probe at 570nm in solutions of RNA of different concentrations. As can be seen from the fitted curve of FIG. 4 (D), the RNA binding constant thereof was 1.08X10 3 M -1 。
From this, it can be seen that the organic compound TBCL can be used to detect RNA.
As described above, although the present invention has been shown and described with reference to certain preferred embodiments, it is not to be construed as limiting the invention itself. Various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (10)

1. A benzothiazole organic compound, characterized in that the chemical name of the compound is: (E) -2- (3-chloro-4-hydroxy-5-methoxystyryl) -3-methylbenzothiazole-3-iodonium salt; the structural formula is as follows:
2. use of the benzothiazole organic compound according to claim 1 for observing pH of a solution under excitation of a single excitation light.
3. The use according to claim 2, wherein the compound detects the pH of the solution under visible light conditions.
4. The use according to claim 2, wherein the compound is added to the solution to be tested by detecting the fluorescence intensity I of the solution F Then according to the equation log [ (1.5-I)/(I-0.07)]=ph-5 to calculate the pH of the solution.
5. The use according to claim 4, wherein the pH of the solution is in the range of 3.0-9.0.
6. The use according to claim 4, wherein the concentration of the compound in solution is 5-15 μm; preferably 10 μm.
7. A method for detecting pH of a solution of benzothiazole organic compound according to claim 1, comprising the steps of:
(1) Adding the benzothiazole organic compound into a solution to be detected;
(2) Exciting under 470nm single excitation light by using fluorescence intensity detection equipment to obtain a fluorescence intensity ratio I of the solution at 530nm and 590nm;
(3) The pH of the mixed solution was directly calculated according to the equation log [ (1.5-I)/(I-0.07) ]=ph-5.
8. Use of the benzothiazole organic compound according to claim 1 for detecting RNA.
9. Use of the benzothiazole organic compound according to claim 1 for preparing an RNA detection reagent.
10. Use of the benzothiazole organic compound according to claim 1 for preparing a tumor diagnostic reagent, a fluorescent imaging reagent or a radioactive imaging reagent for tumors.
CN202311471084.2A 2023-11-07 2023-11-07 Benzothiazole organic compound and application thereof Pending CN117510433A (en)

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