CN110885312B - Golgi-targeted cysteine fluorescent probe, and preparation method and application thereof - Google Patents
Golgi-targeted cysteine fluorescent probe, and preparation method and application thereof Download PDFInfo
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
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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
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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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- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G—PHYSICS
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- 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
- G01N2021/6417—Spectrofluorimetric devices
Abstract
The invention relates to a cysteine fluorescent probe targeting a Golgi apparatus, a preparation method and an application thereof, in particular to a cysteine fluorescent probe which can be used for measuring, detecting or screening cysteine and live cell fluorescence imaging, especially can be used for measuring, detecting or screening and imaging cysteine in the Golgi apparatus, and the probe can realize at least one of the following technical effects: the targeted Golgi body positioning effect is good, cysteine is recognized with high selectivity, the response to the cysteine can be realized quickly, the ultrasensitive analysis to the cysteine can be realized, the cysteine can be detected under the physiological level condition, the anti-interference capability is strong, the synthesis is simple, and the property is stable.
Description
Technical Field
The invention belongs to the field of fluorescent probes, and particularly relates to a fluorescent probe targeting a Golgi apparatus and application thereof in a fluorescence imaging method for measuring, detecting or screening cysteine and living cells; the invention also provides a method for preparing the fluorescent probe.
Background
Cysteine is the main form of sulfur in organisms, participates in many physiological and pathological processes, and plays an important role in maintaining the redox homeostasis of biological systems. In the antioxidant defense system, cysteine can protect biomolecules in healthy cells, increase cysteine production in cells, reverse inflammation-induced cellular abnormalities, and increase cell survival by protecting cells by degrading reactive oxygen species. More importantly, some physiological and pathological processes, such as aging and neurodegenerative diseases, are associated with changes in the oxidative/antioxidant balance and cysteine levels. The golgi apparatus, an important organelle, is involved in the packaging and transport of proteins and plays an important role in the life, and the mechanism of action of cysteine in the golgi apparatus, which indirectly results from the absence of an effective technique for detecting cysteine in the golgi apparatus, has not been completely elucidated. Therefore, it is crucial to find a specific and sensitive technique for detecting cysteines in living organisms, especially in the golgi apparatus.
In view of this, it is extremely important and meaningful to develop an analytical method capable of efficiently detecting fluctuations in the content of cysteine, particularly in the Golgi apparatus. In recent years, methods for detecting cysteine have been reported as spectrophotometric methods, high performance liquid chromatography, chemiluminescence analysis methods, fluorescent probe analysis methods, and the like, and among them, fluorescent probes have been the focus of attention of researchers due to their unique advantages such as high selectivity, ultrasensitiveness, and simplicity of synthesis. The currently reported cysteine fluorescent probe analysis method still has certain defects, such as low sensitivity, poor selectivity, poor water solubility, complex synthesis and the like, and simultaneously, the Golgi apparatus cannot be targeted; and other thiol compounds in the body have similar properties with cysteine, which can potentially interfere the detection of cysteine, and the content of cysteine in the physiological environment is low. Therefore, the development of a cysteine fluorescent probe with high selectivity, interference resistance, ultrasensitiveness and a function of targeting a Golgi apparatus is a problem to be solved.
Disclosure of Invention
In view of the above, the present invention aims to provide cysteine fluorescent probes, and their preparation methods and uses, which have the characteristics of simple synthesis, high selectivity, strong anti-interference capability, and high sensitivity, and can exhibit an excellent golgi targeted localization effect, and can measure, detect, or screen and image cysteine in golgi.
Specifically, the invention provides a compound having a structure represented by formula (I):
in the compound of formula (I), R1、R2、R3、R4、R5、R6、R7And R8Is independently selected from the group consisting of a hydrogen atom, a linear or branched alkyl group, a linear or branched alkoxy group, a sulfonic acid group, an ester group and a hydroxyl group; and wherein R is1、R2、R3、R4、R5、R6、R7And R8May be the same or different.
In some embodiments of the invention, the compound of the invention is R1、R2、R3、R4、R5、R6、R7And R8A compound of formula (I) each being a hydrogen atom, having the formula:
the invention also provides a preparation method of the compound shown in the formula (I) or the formula (II), which takes the compound shown in the formula (III), 1-thiocarbonyldiimidazole and propanethiol as raw materials to carry out reaction according to the following reaction route:
in formula (I), formula (IV) and formula (III): r1、R2、R3、R4、R5、R6、R7And R8Is independently selected from the group consisting of a hydrogen atom, a linear or branched alkyl group, a linear or branched alkoxy group, a sulfonic acid group, an ester group and a hydroxyl group; and wherein R is1、R2、R3、R4、R5、R6、R7And R8May be the same or different.
In some embodiments of the invention, R is1、R2、R3、R4、R5、R6、R7And R8Are all made ofDissolving a hydrogen atom compound shown in the formula (III) and triethylamine in N, N-dimethylformamide, dropwise adding a 1, 1-thiocarbonyldiimidazole-containing N, N-dimethylformamide solution into the mixed solution, reacting at normal temperature for 6-24 hours, then adding propanethiol into the solution, wherein the molar ratio of the compound shown in the formula (III) to the propanethiol is 1:1-1:6, continuing to react at normal temperature for a period of 6-24 hours, extracting, and evaporating the solvent to dryness under reduced pressure to obtain a crude product. The crude product is continuously purified and separated to obtain the pure compound shown in the formula (I).
In some embodiments of the invention, the separation and purification method is chromatography column separation.
In some embodiments of the invention, the eluent used for the chromatographic column separation is a mixed solvent of petroleum ether and dichloromethane.
The invention also provides a fluorescent probe composition for measuring, detecting or screening cysteine, which comprises the compound of formula (I) of the invention.
In some embodiments of the invention, the compound of formula (I) has the following structure:
in some embodiments of the invention, the fluorescent probe composition further comprises a solvent, an acid, a base, a buffer solution, or a combination thereof.
The present invention also provides a method for detecting the presence of or determining the amount of cysteine in a sample comprising:
a) contacting the compound of formula (I) or formula (ii) with a sample to form a fluorescent compound;
b) determining the fluorescent properties of the fluorescent compound.
In some embodiments of the invention, the sample is a chemical sample or a biological sample.
In some embodiments of the invention, the sample is a biological sample comprising water, blood, microorganisms, or animal cells or tissues.
The invention also provides a kit for detecting the presence of cysteine in a sample or determining the amount of cysteine in a sample, comprising the compound of formula (I) or formula (II).
The invention also provides application of the compound shown in the formula (I) or the formula (II) in cell fluorescence imaging.
The invention also provides application of the compound shown in the formula (I) or the formula (II) as a fluorescent probe in targeted positioning Golgi body measurement, detection or cysteine screening.
Compared with the prior art, the invention has the following remarkable advantages and effects:
(1) high selectivity and high anti-interference ability
The hydrogen sulfide probe of the invention can selectively and specifically react with cysteine to generate a fluorescence change product, compared with other common metal ions and other substances in a living body, including but not limited to the following analytes: proline, aspartic acid, serine, alanine, valine, arginine, DL-isoleucine, methionine, glutamine, leucine, glutamic acid, threonine, histidine, potassium ions, sodium ions, calcium ions, magnesium ions, bisulfite, sulfite, sulfate, ascorbic acid and the like.
(2) High sensitivity
The cysteine fluorescent probe of the invention reacts with cysteine very sensitively, thereby being beneficial to the detection of cysteine.
(3) Can target and position the Golgi body
The cysteine fluorescent probe can be applied under the condition of physiological level, especially can target and position the Golgi apparatus, quickly measure, detect or screen cysteine in the Golgi apparatus, and can be applied to live cell fluorescence imaging.
(4) Good stability
The cysteine probe of the invention has good stability and can be stored and used for a long time.
(5) Simple synthesis
The cysteine fluorescent probe is simple to synthesize and is beneficial to commercial popularization and application.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1a fluorescence spectra before and after addition of cysteine (0-10. mu.M) to the probe (5. mu.M);
FIG. 1b working curve of probe (5. mu.M) for quantitative analysis of different concentrations of cysteine (0-10. mu.M);
FIG. 2 fluorescence intensity at 515nm as a function of time after addition of cysteine (20. mu.M) to the probe (5. mu.M).
FIG. 3 influence of substances commonly found in human body on fluorescence intensity of probe (5. mu.M). Wherein the numbers 1-23 are blank, proline, aspartic acid, serine, alanine, valine, arginine, DL-isoleucine, methionine, glutamine, leucine, glutamic acid, threonine, histidine, potassium ion, sodium ion, calcium ion, magnesium ion, bisulfite, sulfite, sulfate, ascorbic acid and cysteine (20 μ M) (except special indication, other analyte concentration is 100 μ M), and the analyte concentration is 1mM except special indication. The bar graph represents the fluorescence intensity values at 515nm for the probes in the presence of different analytes;
FIG. 4 effect of different analytes on the fluorescence spectrum of the probe (5. mu.M) with time.
FIG. 5 confocal microscopy was used to observe the co-localization ability of the probe (5. mu.M) to Golgi.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and should not be used to limit the scope of the present invention. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, belong to the scope of the present invention.
Example 1: synthesis of Compounds of formula (II)
The synthetic design route is as follows:
step a)
Step b)
Embodiment 1: dissolving 500mg (1.73mmol) of 4-trifluoromethyl-7-aminoquinoline compound and triethylamine in N, N-dimethylformamide, dropwise adding N, N-dimethylformamide solution containing 1, 1-thiocarbonyldiimidazole into the mixed solution, reacting at normal temperature for 12h, adding 132mg (1.73mmol) of propanethiol into the solution, reacting at normal temperature for 12h, extracting, and rotary-evaporating the solvent under reduced pressure. The crude product was subjected to column chromatography using a mixed system of petroleum ether and dichloromethane (v/v ═ 2:1) to give a pure product, 340mg of a white pure product, with a yield of 48%.
Embodiment 2: dissolving 500mg (1.73mmol) of 4-trifluoromethyl-7-aminoquinoline compound and triethylamine in N, N-dimethylformamide, dropwise adding N, N-dimethylformamide solution containing 1, 1-thiocarbonyldiimidazole into the mixed solution, reacting at normal temperature for 12h, adding 264mg (3.46mmol) of propanethiol into the solution, reacting at normal temperature for 12h, extracting, and rotary-evaporating the solvent under reduced pressure. The crude product was subjected to column chromatography using a mixed system of petroleum ether and dichloromethane (v/v ═ 2:1) to give a pure product, 420mg of a white pure product, with a yield of 60%.
Embodiment 3: dissolving 500mg (1.73mmol) of 4-trifluoromethyl-7-aminoquinoline compound and triethylamine in N, N-dimethylformamide, dropwise adding N, N-dimethylformamide solution containing 1, 1-thiocarbonyldiimidazole into the mixed solution, reacting at normal temperature for 12h, adding 396mg (5.19mmol) of propanethiol into the solution, reacting at normal temperature for 12h, extracting, and rotary-evaporating the solvent under reduced pressure. The crude product was subjected to column chromatography using a mixed system of petroleum ether and dichloromethane (v/v ═ 2:1) to give a pure product, 490mg of a white pure product, with a yield of 70%.
Embodiment 4: dissolving 500mg (1.73mmol) of 4-trifluoromethyl-7-aminoquinoline compound and triethylamine in N, N-dimethylformamide, dropwise adding N, N-dimethylformamide solution containing 1, 1-thiocarbonyldiimidazole into the mixed solution, reacting at normal temperature for 12h, adding 528mg (6.92mmol) of propanethiol into the solution, reacting at normal temperature for 12h, extracting, and rotary-evaporating the solvent under reduced pressure. The crude product was subjected to column chromatography using a mixed system of petroleum ether and dichloromethane (v/v ═ 2:1) to give a pure product, 520mg of a white pure product, with a yield of 75%.
Embodiment 5: dissolving 500mg (1.73mmol) of 4-trifluoromethyl-7-aminoquinoline compound and triethylamine in N, N-dimethylformamide, dropwise adding N, N-dimethylformamide solution containing 1, 1-thiocarbonyldiimidazole into the mixed solution, reacting at normal temperature for 12h, adding 528mg (6.92mmol) of propanethiol into the solution, reacting at normal temperature for 6h, extracting, and rotary-evaporating the solvent under reduced pressure. The crude product was subjected to column chromatography using a mixed system of petroleum ether and methylene chloride (e.g., v/v,2:1) to give a pure product in the form of 405mg of white pure product with a yield of 58%.
Example 2: testing the concentration gradient of fluorescent probes for cysteine
Preparing a plurality of parallel samples with the probe concentration of 5 mu M in a 10mL colorimetric tube, adding cysteine with different concentrations into the test system, shaking uniformly, and standing for 30 minutes. The above assay was performed in an ethanol-water-3: 7(10mM PBS, pH 7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were performed at 25 ℃.
The fluorescence intensity change was measured by fluorescence spectroscopy, and as is clear from FIG. 1a, the fluorescence intensity at 515nm gradually increased with increasing cysteine concentration. Furthermore, it can be seen from FIG. 1b that the fluorescence intensity of the fluorescent probe (5. mu.M) added with cysteine (0-10. mu.M) has a good linear relationship with the concentration of cysteine, which proves that the quantitative analysis of cysteine can be performed by the fluorescent probe.
Example 3: testing time dynamics of fluorescent probes
50 mu L of the probe stock solution is taken out and placed in a 10mL test system, 20 mu M of cysteine is added into the test system, and the change of the fluorescence intensity is tested by a fluorescence spectrometer immediately after the probe stock solution is uniformly shaken. The above assay was performed in an ethanol-water-3: 7(10mM PBS, pH 7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were performed at 25 ℃.
As is clear from FIG. 2, when cysteine was added, the fluorescence intensity reached a maximum value and remained unchanged after about 30min of detection, indicating that the probe reacted with cysteine rapidly, providing a rapid analytical method for cysteine determination.
Example 4: testing the selectivity of fluorescent probes for cysteine
The analytes were blank, proline, aspartic acid, serine, alanine, valine, arginine, DL-isoleucine, methionine, glutamine, leucine, glutamic acid, threonine, histidine, potassium, sodium, calcium, magnesium, bisulfite, sulfite, sulfate, ascorbic acid, cysteine, respectively (except for the specific indications, the analyte concentrations were 100 μ M). The bar graph represents the fluorescence intensity values of the probes at 515nm in the presence of different analytes. The above assay was performed in an ethanol-water-3: 7(10mM PBS, pH 7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were performed at 25 ℃.
Specifically, a plurality of parallel samples with a probe concentration of 5 μ M were placed in a 10mL cuvette, and then a certain amount of analyte was added, shaken up, and measured after 30 minutes. As is clear from FIG. 3, the probe has high selectivity for cysteine.
Example 5: testing the selectivity of fluorescent probes for cysteine
The fluorescence intensity of the analytes homocysteine (100. mu.M), hydrogen sulfide (100. mu.M), glutathione (1mM) and cysteine (20. mu.M) respectively, as a function of time, and the dotted plot represents the fluorescence intensity of the probe at 515nm in the presence of the different analytes. The above assay was performed in an ethanol-water-3: 7(10mM PBS, pH 7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were performed at 25 ℃.
Specifically, a plurality of parallel samples of 5 μ M probe concentration were placed in 10mL cuvettes, and then a certain amount of analyte was added, shaken, and measured every 3 minutes. As is clear from FIG. 4, the probe has high selectivity for cysteine.
Example 6: co-localization ability test of probes (5. mu.M) to Golgi apparatus
Hela cells were incubated with Cys for 30min and then with the probe and commercial Golgi probe (BODIPY TR ceramide) for 40 min. The co-localization ability of the probes was observed by confocal microscopy. As can be seen from FIG. 5, the overlapping effect of the probe and the Golgi apparatus is good, and the excellent capability of positioning the Golgi apparatus of the probe is shown.
Although the present invention has been described in the above-mentioned embodiments, it is to be understood that the present invention may be further modified and changed without departing from the spirit of the present invention, and that such modifications and changes are within the scope of the present invention.
Claims (8)
1. A compound having the structure:
2. a process for the preparation of a compound according to claim 1, characterized in that starting from 4-phenyl-2-trifluoromethyl-7-aminoquinoline, 1-thiocarbonyldiimidazole and propanethiol, the reaction is carried out according to the following reaction scheme:
3. the preparation method of claim 2, wherein 4-phenyl-2 trifluoromethyl-7 aminoquinoline and triethylamine are dissolved in N, N-dimethylformamide, a solution of N, N-dimethylformamide containing 1, 1-thiocarbonyldiimidazole is added dropwise to the above mixed solution, and then reaction is carried out at normal temperature for 6-24 hours, and then propanethiol is added to the above solution, wherein the molar ratio of 4-phenyl-2 trifluoromethyl-7 aminoquinoline to propanethiol is 1:1-1:6, and the reaction is continued at normal temperature for 6-24 hours, extraction is carried out, and the solvent is evaporated under reduced pressure to obtain a crude product; the crude product is continuously purified and separated to obtain the pure compound shown in the formula (II).
4. A fluorescent probe composition for applications in cellular imaging, fluorescent probes, laser dyes, fluorescent sensors, near infrared photodynamics, comprising a compound of claim 1.
5. The fluorescent probe composition of claim 4, wherein the fluorescent probe composition further comprises a solvent, an acid, a base, a buffer solution, or a combination thereof.
6. A method for detecting the presence of or determining the amount of cysteine in a sample for non-therapeutic or diagnostic purposes comprising:
a) contacting the compound of claim 1 with a sample to form a fluorescent compound;
b) determining the fluorescent properties of the fluorescent compound.
7. Use of a compound according to claim 1 for the preparation of a reagent for cellular fluorescence imaging.
8. The use of the compound of claim 1 in the preparation of a fluorescent probe targeted Golgi assay, detection or screening cysteine reagents.
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