CN118772016A - Fluorescent probe for detecting hydrogen sulfide targeting endoplasmic reticulum of cells and preparation method and application thereof - Google Patents
Fluorescent probe for detecting hydrogen sulfide targeting endoplasmic reticulum of cells and preparation method and application thereof Download PDFInfo
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Abstract
本发明公开了一种靶向细胞内质网的检测硫化氢的荧光探针及其制备方法与应用，荧光探针，其化学结构式如式(I)所示：该荧光探针不仅可以定量检测溶液体系中的硫化氢，而且能够用于活细胞内的硫化氢成像；有望在检测含硫化氢的生物样品中发挥作用，具有广阔的应用前景。
The present invention discloses a fluorescent probe for detecting hydrogen sulfide targeting the endoplasmic reticulum of a cell and a preparation method and application thereof. The fluorescent probe has a chemical structure as shown in formula (I): This fluorescent probe can not only quantitatively detect hydrogen sulfide in solution systems, but also can be used for hydrogen sulfide imaging in living cells. It is expected to play a role in the detection of biological samples containing hydrogen sulfide and has broad application prospects.
Description
Technical Field
The invention belongs to the technical field of organic micromolecular fluorescent probes, and in particular relates to a fluorescent probe for detecting hydrogen sulfide of a targeted cell endoplasmic reticulum, a preparation method and application thereof, wherein ((E) -2- (5, 5-dimethyl-3- (4-nitrosostyryl) cyclohex-2-ene-1-subunit) malononitrile taking nitroso as a hydrogen sulfide recognition group is used for detecting hydrogen sulfide in the cell endoplasmic reticulum.
Background
The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art.
Hydrogen sulfide (H 2 S) is the third endogenous gas signaling molecule discovered in recent years and is involved in a number of physiological activities in many tissues such as the cardiovascular and cerebrovascular system, the nervous system, the gastrointestinal digestive system, endocrine and immune systems. Abnormal hydrogen sulfide levels are closely related to the occurrence of various diseases such as vascular diseases, tumors, alzheimer's disease, diabetes, etc. The method has important significance in monitoring the concentration and distribution of endogenous hydrogen sulfide of organisms in real time, and is helpful for researching the physiological and pathological actions of the hydrogen sulfide.
However, due to the high volatility, high reactivity, and rapid catabolism of hydrogen sulfide, achieving its monitoring and detection in biological systems presents a number of serious challenges. The fluorescent probe method has great potential in hydrogen sulfide sensitive detection application due to the advantages of low cost, high biocompatibility, real-time sensing, high selectivity and the like, and has been widely paid attention by scientists in recent years. When constructing a fluorescent probe for hydrogen sulfide, the nitro group is a commonly used recognition group by utilizing the reducibility of hydrogen sulfide. However, the identification probes designed based on the principle have the defects of long response time, low sensitivity, high organic reagent content of a test system and the like, and development of new fluorescent probes is needed.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a fluorescent probe for detecting hydrogen sulfide by targeting an endoplasmic reticulum of a cell, and a preparation method and application thereof.
In order to achieve the above object, the present invention is realized by the following technical scheme:
in a first aspect, the invention provides a fluorescent probe for detecting hydrogen sulfide targeting an endoplasmic reticulum of a cell, wherein the chemical structural formula of the fluorescent probe is shown as a formula (I):
The chemical name of the fluorescent probe is: ((E) -2- (5, 5-dimethyl-3- (4-nitrosostyryl) cyclohex-2-en-1-ylidene) malononitrile (abbreviated to YNO) consists of the recognition group nitrosyl and the electron withdrawing fluorescent group dicyanoisophorone.
The fluorescence probe for detecting hydrogen sulfide of the targeting endoplasmic reticulum provided by the invention has no fluorescence; after reaction with hydrogen sulfide, the new product is obtained by reduction, nitroso becomes amino with strong electron pushing effect, an ICT is generated by forming a electron pushing-pulling structure, and strong fluorescence is emitted.
In a second aspect, the invention provides a preparation method of the fluorescent probe for detecting hydrogen sulfide targeting the endoplasmic reticulum of a cell, which comprises the following steps:
Heating and refluxing (3, 5-trimethylcyclohex-2-ene subunit) malononitrile and 4-formylphenyl potassium trifluoroborate for reaction to obtain an intermediate product;
Reacting the intermediate product with the tetrafluoroboric acid nitrite at 20-40 ℃ for 5-20min to obtain the fluorescent probe.
The chemical reaction equation is as follows:
In some embodiments, the temperature of the heated reflux reaction is 78-83 ℃ for a period of 10-15 hours. The solvent for heating reflux is ethanol.
In some embodiments, the catalyst during the heated reflux reaction is piperidine.
In some embodiments, after the intermediate product and the tetrafluoroboric acid are reacted, the reaction system is separated and purified by adopting flash column chromatography, and the chromatographic liquid is pure dichloromethane, thus obtaining the fluorescent probe.
In some embodiments, the molar ratio of (3, 5-trimethylcyclohex-2-enyl) malononitrile to the potassium 4-formylphenyl trifluoroborate is 1:0.8-1.2.
In some embodiments, the molar ratio of intermediate to nitrous tetrafluoroborate is 1:0.8-1.2.
Preferably, the molar ratio of intermediate to nitrous tetrafluoroborate is 1:1.
In a third aspect, the invention provides the use of the fluorescence probe for detecting hydrogen sulfide targeting the cytoplasmic reticulum in detecting hydrogen sulfide-containing samples.
In some embodiments, the hydrogen sulfide-containing sample is a cell or a cell solution.
The beneficial effects achieved by one or more embodiments of the present invention described above are as follows:
The fluorescent probe for detecting hydrogen sulfide can target an endoplasmic reticulum, detect the concentration of hydrogen sulfide in the endoplasmic reticulum, and is beneficial to researching the biological function of hydrogen sulfide in the endoplasmic reticulum. The probe is highly selectively acted with hydrogen sulfide, and along with the increase of the concentration of the hydrogen sulfide, the fluorescence emission intensity of the probe is gradually enhanced to a peak at 652nm and is in a linear relation in a certain range. The fluorescent probe not only can quantitatively detect hydrogen sulfide in a solution system, but also can be used for hydrogen sulfide imaging in living cells; is expected to play a role in detecting biological samples containing hydrogen sulfide, and has wide application prospect.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention.
FIG. 1 is a diagram showing a mechanism of recognition of a fluorescent probe and hydrogen sulfide according to the present invention.
FIG. 2 is a graph showing the selectivity of the response of a fluorescent probe according to the present invention to various analytes (e.g., ：F-,Br-,I-,CO3 2-,NO3 -,NO2 -,SCN-,HSO3 -,SO4 2-,CH3COO-,S2O3 2-,ClO-,H2O2,Cys,Hcy,GSH,PhSH) and a comparison of its interference resistance.
FIG. 3 is a graph showing the titration spectrum (panel a) and the linear relationship between the fluorescence intensity at 652nm and the NaSH concentration (panel b) of the fluorescent probe of the present invention.
FIG. 4 is a fluorescence imaging diagram of the exogenous hydrogen sulfide confocal fluorescence of Hela cells by using the fluorescent probe (5 mu M) according to the invention, and a red channel (600-700 nm), wherein: (a) is a cell image under the conditions shown; (b) Is a bar graph of red channel fluorescence intensity under conditions corresponding to (a).
FIG. 5 is a graph of fluorescence imaging of a fluorescent probe (5. Mu.M) of the present invention on hydrogen sulfide confocal fluorescence of HeLa cells, red channel (600-700 nm), wherein: (a) is a cell image under the conditions shown; (b) Is a bar graph of red channel fluorescence intensity under conditions corresponding to (a).
FIG. 6 is a schematic diagram of a fluorescent probe targeting the HeLa cells of the endoplasmic reticulum according to the present invention, wherein: (a) For the probe imaging diagram of the invention, lambda ex =405 nm, and the red channel is 600-700nm; (b) For a commodity dye ER-Tracker TM Red imaging diagram of targeting an endoplasmic reticulum, lambda ex =561 nm, and a Red channel of 561-700nm; (c) is a superposition of (a) and (b); (d) is a co-localization coefficient diagram (coefficient 0.94).
Detailed Description
It should be noted that the following detailed description is illustrative and is intended to provide further explanation of the invention. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The invention is further illustrated below with reference to examples.
Example 1
(3, 5-Trimethylcyclohex-2-enyl) malononitrile (313 mg,3.3 mmol) and potassium 4-formylphenyl trifluoroborate (636 mg,3 mmol) were dissolved in 25ml of ethanol, and 1 drop of piperidine was added dropwise thereto and heated under reflux for 12 hours. After the reaction is finished, cooling and standing to room temperature, carrying out suction filtration, washing filter residues with 1ml of ethanol for three times, and drying to obtain a yellow solid compound 3. Compound 3 (380 mg,1 mmol) was dissolved in 10ml of acetonitrile, and nitrotetrafluoroborate (117 mg,1 mmol) was added and reacted at room temperature for 10min. Flash column chromatography (pure dichloromethane as the chromatographic solution) after the reaction was completed gave a brown solid probe ((E) -2- (5, 5-dimethyl-3- (4-nitrosostyryl) cyclohex-2-en-1-ylidene) malononitrile (abbreviated YNO) in 83% yield.
Structure confirmation spectrogram data:
IR(KBr,cm-1):2228.45，1586.06，1109.06，832.76.
1H NMR(400MHz,DMSO-d6)δ8.29(d,J＝8.1Hz,2H),8.04(d,J＝8.2Hz,2H),7.98(d,J＝16.7Hz,1H),7.46(d,J＝16.5Hz,1H),1.83(s,6H).
13C NMR(101MHz,DMSO)δ177.38,174.33,164.41,144.63,141.70,131.27,121.69,120.09,112.96,112.13,111.03,102.66,100.18,55.99,25.42.
HRMS (ESI, M/z) [ M+H ] + found 317.1030, calculated [ C 18H13N4O2]+: 317.1034.
The preparation reaction of the fluorescent probe YNO is shown as follows:
Example 2
Test solutions (PBS buffer/1, 4-dioxane, v/v=8:2, ph=7.4) were prepared. To a 10mL volumetric flask containing 5. Mu.M of the probe, 50. Mu.M F-,Br-,I-,CO3 2-,NO3 -,NO2 -,SCN-,HSO3 -,SO4 2-,CH3COO-,S2O3 2-,ClO-,H2O2,Cys,Hcy,GSH,PhSH. were added with a micropipette, and the reaction was performed for 20 minutes, followed by fluorescence test.
The results show that the probe YNO of the present invention has good response and selectivity to hydrogen sulfide only and good interference immunity to other analytes, as shown in fig. 2.
Example 3
To a 10mL volumetric flask equipped with 5. Mu.M fluorescent probe YNO of the present invention, sodium hydrosulfide of gradient concentration of 0-16. Mu.M was added, respectively, with a microsyringe, and the reaction was performed for 20 minutes, followed by fluorescence test.
The result shows that the fluorescence intensity of the fluorescence probe YNO gradually increases along with the increase of the concentration of sodium hydrosulfide, and the fluorescence intensity reaches a peak at 652nm and has a linear relation with the concentration of hydrogen sulfide within a certain range, as shown in figure 3. It was confirmed that the fluorescent probe YNO of the present invention was able to quantitatively detect hydrogen sulfide at a low concentration.
Example 4
Intracellular fluorescence imaging test:
the laser scanning confocal microscope is set to have an excitation wavelength of 405nm and a red channel collection wavelength of 600-700nm.
After transfer of Hela cells to a small glass flask for incubation for 24 hours, the experiments were grouped.
Control group: cells were incubated with the fluorescent probe YNO (5. Mu.M) solution of the invention for 0.5 hours, then washed three times with PBS and then examined by imaging using a laser scanning confocal microscope. It can be seen that the red channel fluorescence of the cells of the control group was almost absent.
Test group: after incubating Hela cells for 0.5 hours with 5. Mu.M of the fluorescent probe YNO solution, incubation was continued for 1 hour with 100. Mu.M, 200. Mu.M, 500. Mu.M, 1000. Mu.M NaSH, respectively; imaging detection was performed using a laser scanning confocal microscope. It can be seen that the red fluorescence intensity is significantly increased gradually as the NaSH concentration increases, see fig. 4.
Or test group: the first group of cells was incubated with 5. Mu.M probe YNO min only as a blank; the second group of cells was pretreated with 200. Mu.M cysteine for 60 minutes and then treated with 5. Mu.M probe for 60 minutes; the third to five groups were pretreated with PAG (1 mM), AOAA (1 mM) and pag+aoaa for 60 min, followed by cysteine (200 μm) for 60 min and then incubated with YNO (5 μm) for 30min, respectively. Imaging detection was performed using a laser scanning confocal microscope. It can be seen that the second group has significantly increased fluorescence intensity compared to the blank group, indicating successful response of the probe to endogenous H 2 S. The third, fourth and fifth groups showed lower fluorescence intensities, indicating that endogenous H 2 S production was inhibited, see FIG. 5.
Example 5
Intracellular targeting fluorescence imaging assay:
HeLa cells were incubated with 5. Mu.M probe YNO for 30 minutes, then with the commercial dye ER-Tracker TM Red added to the endoplasmic reticulum for 30 minutes, and imaged with a laser scanning confocal microscope. It can be seen that the co-localization coefficient of probe YNO in the endoplasmic reticulum is 0.94, indicating that the prepared fluorescent probe YNO is capable of targeting the endoplasmic reticulum, see fig. 6.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
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