CN110878049B - Preparation and application of fluorescent probe for specifically analyzing hydrogen sulfide in Golgi apparatus - Google Patents
Preparation and application of fluorescent probe for specifically analyzing hydrogen sulfide in Golgi apparatus Download PDFInfo
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Abstract
The invention relates to preparation and application of a fluorescent probe for specifically analyzing hydrogen sulfide in a Golgi apparatus, in particular to a fluorescent probe for naphthalimide compounds, which can be used as a hydrogen sulfide fluorescent probe, especially can be used for targeting positioning of the Golgi apparatus and is used for measuring, detecting or screening the hydrogen sulfide in the Golgi apparatus. Such probes can achieve at least one of the following technical effects: the selectivity is high, and hydrogen sulfide in a Golgi apparatus can be measured, detected or screened; the anti-interference capability is strong, and the interference of other substances in the life body corresponding to the detection of the probe can be prevented; the sensitivity is high, and the method is suitable for detecting trace hydrogen sulfide in a living body; simple synthesis and stable property, and is suitable for commercial popularization and use.
Description
Technical Field
The invention belongs to the field of fluorescent probes, and particularly relates to a fluorescent probe of a naphthalimide compound and application thereof in a method for measuring, detecting or screening hydrogen sulfide in Golgi apparatus and live cell fluorescence imaging; the invention also provides a method for preparing the fluorescent probe.
Background
The hydrogen sulfide is colorless gas with irritation and asphyxiation, the low-concentration contact only has the local irritation of respiratory tract and eyes, and the general action is obvious when the hydrogen sulfide is high in concentration, and the hydrogen sulfide is manifested as central nervous system symptom and asphyxiation symptom.
In view of this, it is extremely important and interesting to develop analytical methods that allow the effective detection of fluctuations in the content of hydrogen sulfide, in particular in certain organelles. Analytical methods reported today for detecting hydrogen sulfide include mercury methods, detector tube methods, methylene blue colorimetric methods, and the like. Fluorescent probes have been the focus of attention among these numerous detection methods due to their unique advantages. However, the fluorescent probes reported so far still have some problems, including poor selectivity, slow response speed, complex synthesis, and inability to detect and analyze hydrogen sulfide in specific organelles. Due to other components in vivo such as alanine (Ala), phenylalanine (Phe), methionine (Met), glycine (Gly), glutamic acid (Glu), arginine (Arg), lysine (Lys), tryptophan (Trp), and sulfate radical (SO)4 2-) Bisulfite (HSO)3 -) Chloride ion (Cl)-) Carbonate (CO)3 2-) Bicarbonate radical (HCO)3 -) Nitrate radical (NO)3 -) Sulfite (SO)3 2-) Hydrogen peroxide (H)2O2) Hypochlorite (ClO)-)And the like, which potentially interfere with the detection of hydrogen sulfide, and therefore, a fluorescent probe capable of measuring, detecting or screening hydrogen sulfide in the golgi, which is rapid, highly selective, highly sensitive, and simple in synthesis, has become a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention aims to provide a class of fluorescent probes for analyzing hydrogen sulfide in golgi with high selectivity, and their preparation methods and uses, and the fluorescent probes have the characteristics of simple synthesis, good selectivity, high sensitivity, and capability of measuring, detecting or screening hydrogen sulfide in golgi.
Specifically, the invention provides a compound having a structure represented by formula (I):
R1、R2、R3、R4、R5、R6、R7、R8and R9Is hydrogen atom, straight chain or branched chain alkyl, straight chain or branched chain alkoxy, sulfonic group, ester group, carboxyl; r1、R2、R3、R4、R5、R6、R7、R8And R9May be the same or different.
In some embodiments of the invention, the compound of the invention is R1、R2、R3、R4、R5、R6、R7、R8And R9A 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 comprises the following steps: dissolving a compound shown in a formula (III) and sodium azide in dimethyl sulfoxide (DMSO), heating and stirring until the reaction is finished, extracting and filtering reaction liquid to obtain a crude product, and separating and purifying to obtain a pure compound shown in a formula (I), wherein the reaction formula is as follows:
wherein: r1，R2，R3，R4，R5，R6，R7，R8And R9Is hydrogen atom, straight chain or branched chain alkyl, straight chain or branched chain alkoxy, sulfonic group, ester group, carboxyl; r1，R2，R3，R4，R5，R6，R7，R8And R9May be the same or different.
In some embodiments of the invention, the reaction time is from 6 to 48 hours.
In some embodiments of the invention, the molar ratio of the compound of formula (III) to sodium azide is from 1:1 to 10: 1.
In some embodiments of the invention, the heating reaction temperature is from 80 to 100 ℃.
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 dichloromethane and petroleum ether.
In some embodiments of the invention, R is1、R2、R3、R4、R5、R6、R7、R8And R9The compound of formula (III) which is a hydrogen atom and sodium azide are dissolved in dimethyl sulfoxide (DMSO) at a molar ratio of 1:1 to 1:5, and then heated and stirred for 10 to 16 hours. And (3) extracting and filtering the reaction liquid to obtain a crude product, and purifying and separating the crude product by using a mixed solvent (the volume ratio is 1:1-1:3) of dichloromethane and petroleum ether as an eluent through a chromatographic column to obtain the pure compound shown in the formula (I).
The invention also provides a fluorescent probe composition for measuring, detecting or screening hydrogen sulfide, 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 invention also provides a method of detecting the presence of hydrogen sulfide in a sample or determining the amount of hydrogen sulfide 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.
In some embodiments of the invention, the biological sample is golgi.
The invention also provides a kit for detecting the presence of hydrogen sulfide in a sample or determining the amount of hydrogen sulfide 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) in measuring, detecting or screening hydrogen sulfide by the targeted positioning Golgi apparatus.
Compared with the prior art, the invention has the following remarkable advantages and effects: the selectivity is high, and hydrogen sulfide in a Golgi apparatus can be specifically identified; the anti-interference capability is strong, and the interference of other substances in the life body corresponding to the detection of the probe can be prevented; the sensitivity is high, and the method is suitable for detecting trace hydrogen sulfide in a living body; simple synthesis and stable property, and is suitable for commercial popularization and use.
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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. 1(a) fluorescence spectra before and after addition of probe (5. mu.M) to hydrogen sulfide (0-100. mu.M);
FIG. 1(b) probe (5. mu.M) was used to quantify the working curves for different concentrations of hydrogen sulfide (0-30. mu.M);
FIG. 2 influence of substances commonly found in human body on fluorescence intensity of probe (5. mu.M). The bar graph represents the fluorescence intensity values of the probes at 550nm in the presence of different analytes;
FIG. 3 probes and different commercial organelle dyes were incubated on cells and images were taken using a confocal microscope.
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:
embodiment 1: 386mg (1mmol) of the compound shown in the formula (IV) and 65mg (1mmol) of sodium azide are dissolved in DMSO, the mixture is heated and stirred for 10 hours at 90 ℃, the reaction solution is extracted and filtered to obtain a crude product, and the crude product is purified and separated by a chromatographic column by using a mixed solvent (volume ratio is 1:1) of dichloromethane and petroleum ether as an eluent to obtain a pure compound shown in the formula (II). A dark yellow colour was obtained giving 235mg of the compound of formula (II) in 60% yield.
Embodiment 2: 386mg (1mmol) of the compound shown in the formula (IV) and 130mg (2mmol) of sodium azide are dissolved in DMSO, the mixture is heated and stirred for 11 hours at 90 ℃, the reaction solution is extracted and filtered to obtain a crude product, and the crude product is purified and separated by a chromatographic column by using a mixed solvent (volume ratio is 1:1) of dichloromethane and petroleum ether as an eluent to obtain a pure compound shown in the formula (II). 247mg of the compound of the formula (II) are obtained in 63% yield as dark yellow.
Embodiment 3: 386mg (1mmol) of the compound shown in the formula (IV) and 195mg (3mmol) of sodium azide are dissolved in DMSO, the mixture is heated and stirred for 12 hours at 90 ℃, the reaction solution is extracted and filtered to obtain a crude product, and the crude product is purified and separated by a chromatographic column by using a mixed solvent (volume ratio is 1:1) of dichloromethane and petroleum ether as an eluent to obtain a pure compound shown in the formula (II). 255mg of the compound of formula (II) are obtained in 65% yield as dark yellow.
Embodiment 4: 386mg (1mmol) of the compound shown in the formula (IV) and 260mg (4mmol) of sodium azide are dissolved in DMSO, the mixture is heated and stirred for 13 hours at 90 ℃, the reaction solution is extracted and filtered to obtain a crude product, and the crude product is purified and separated by a chromatographic column by using a mixed solvent (volume ratio is 1:1) of dichloromethane and petroleum ether as an eluent to obtain a pure compound shown in the formula (II). 267mg of the compound of the formula (II) were obtained in 68% yield.
Embodiment 5: 386mg (1mmol) of the compound shown in the formula (IV) and 325mg (5mmol) of sodium azide are dissolved in DMSO, the mixture is heated and stirred for 14 hours at 90 ℃, the reaction solution is extracted and filtered to obtain a crude product, and the crude product is purified and separated by a chromatographic column by using a mixed solvent (volume ratio is 1:1) of dichloromethane and petroleum ether as an eluent to obtain a pure compound shown in the formula (II). 290mg of the compound of formula (II) are obtained in 74% yield.
Example 2: testing the concentration gradient of fluorescent probes to Hydrogen sulfide
A plurality of parallel samples with the probe concentration of 5 mu M are arranged in a 10mL colorimetric tube, then hydrogen sulfide (0-100 mu M) with different concentrations is added into the test system, and the test system is shaken uniformly and then stands for 30 min. The above assay was performed in a pure water system (0.5mM PBS, pH 7.4), 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 550nm gradually increased with increasing hydrogen sulfide concentration. Furthermore, it can be seen from FIG. 1b that the fluorescence intensity of the fluorescent probe (5. mu.M) added with hydrogen sulfide (0-30. mu.M) shows a good linear relationship, which demonstrates that the hydrogen sulfide can be quantitatively analyzed by the fluorescent probe.
Example 3: testing the selectivity of fluorescent probes for hydrogen sulfide
The analytes include: 1 blank probe (5. mu.M), 2 Potassium ion (K)+) 3 calcium ion (Ca)2 +) 4 sodium ion (Na)+) 5 fluorine ion (F)-) 6 chloride ion (Cl)-) 7 Bromide ion (Br)-) 8 phenylalanine (Phe), 9 methionine (Met), 10 glycine (Gly), 11 glutamic acid (Glu), 12 arginine (Arg), 13 lysine (Lys), 14 tryptophan (Trp), 15 serine (Ser), 16 threonine (Thr), 17 aspartic acid (Asp), 18 proline (Pro), 19 leucine (Leu), 20 phosphate radical (PO)4 3-) 21 sulfate radical (SO)4 2-)22 cysteine (Cys), 23 Glutathione (GSH), 24 hydrogen sulfide (100. mu.M), the analyte concentration was 1mM unless otherwise noted. All test conditions were done in a pure water system (0.5mM PBS, pH 7.4), the probe used was the probe prepared in example 1, and all spectra were measured after 30 minutes of analyte addition at 25 ℃. Specifically, a portion of water was added followed by 0.5mL of PBS7.4(10mM) buffer, 100. mu.L of each of the above stock solutions (100mM) of analyte (2-23) was pipetted into the tube, and finally the volume was adjusted to 10mL with water. As a result, as shown in FIG. 2, FIG. 2 was a graph in which the fluorescence intensity at an emission wavelength of 550nm was collected. As can be seen from FIG. 2, the probe has good selectivity and can specifically recognize hydrogen sulfide.
Example 4: labeling experiments on different cells with probes and different commercial organelle dyes
The method comprises the following steps of firstly incubating HeLa cells for 30 minutes by using hydrogen sulfide (100 mu M), then adding a probe (10 mu M) and a commercial organelle dye (mitochondria, endoplasmic reticulum, lysosome and Golgi body) for incubating for 30 minutes, then washing for 3 times by using a phosphate buffer solution to reduce background fluorescence, imaging by using a confocal microscope, exciting the wavelength to 488nm by using a green channel, and collecting the wavelength to 510-590 nm; red channel: the mitochondria excitation wavelength is 578nm, and the collection wavelength is 590-640 nm; the excitation wavelength of the endoplasmic reticulum is 594nm, and the collection wavelength is 600-670 nm; the lysosome excitation wavelength is 559nm, and the collection wavelength is 585-620 nm; the Golgi emission wavelength is 633nm, and the collection wavelength is 634-740 nm. As can be seen from FIG. 3, the probe has strong tissue penetrability and can detect hydrogen sulfide in cells, and the overlapping effect of the probe and Golgi apparatus is best in the overlapping field and the red-green fluorescence overlapping coefficient by comparing with dye marks such as Golgi apparatus and the like, and the overlapping coefficients are mitochondria (0.26), endoplasmic reticulum (0.18), lysosome (0.33) and Golgi apparatus (0.94), and show the excellent capability of targeting and positioning the Golgi apparatus.
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 preparing a compound of claim 1, comprising the steps of: dissolving a compound shown in a formula (IV) and sodium azide in dimethyl sulfoxide, heating and stirring until the reaction is finished, extracting and filtering reaction liquid to obtain a crude product, and separating and purifying to obtain a pure compound shown in a formula (II), wherein the reaction formula is as follows:
3. the method of claim 2, comprising the steps of:
dissolving the compound shown in the formula (IV) and sodium azide in dimethyl sulfoxide at a molar ratio of 1:1-1:5, heating and stirring for 6-48 hours, extracting and filtering reaction liquid to obtain a crude product, and purifying and separating the crude product by using a chromatographic column by using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain a pure compound shown in the formula (II).
4. A fluorescent probe composition for measuring, detecting or screening hydrogen sulfide comprising the 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 hydrogen sulfide 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 a compound according to claim 1 for the preparation of a targeted-localization golgi assay, detection or screening agent for hydrogen sulfide.
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| CN104529893A (en) * | 2014-12-30 | 2015-04-22 | 中国科学技术大学 | Novel quinoline dye capable of being used as Golgi apparatus organelle probe |
| CN106867514A (en) * | 2015-12-11 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of small-molecule fluorescent probe and its synthetic method and application for ratio identification people's carbonic anhydrase |
| CN110407865A (en) * | 2019-08-02 | 2019-11-05 | 山东师范大学 | Formula (I) compound and the preparation method and application thereof based on benzsulfamide structure |
| CN110551056A (en) * | 2019-09-29 | 2019-12-10 | 山东师范大学 | Cyanine compound, preparation method and application in detection of Golgi pH |
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| CN104529893A (en) * | 2014-12-30 | 2015-04-22 | 中国科学技术大学 | Novel quinoline dye capable of being used as Golgi apparatus organelle probe |
| CN106867514A (en) * | 2015-12-11 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of small-molecule fluorescent probe and its synthetic method and application for ratio identification people's carbonic anhydrase |
| CN110407865A (en) * | 2019-08-02 | 2019-11-05 | 山东师范大学 | Formula (I) compound and the preparation method and application thereof based on benzsulfamide structure |
| CN110551056A (en) * | 2019-09-29 | 2019-12-10 | 山东师范大学 | Cyanine compound, preparation method and application in detection of Golgi pH |
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