CN113698379A - Fluorescent probe for detecting hydrogen polysulfide and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for detecting hydrogen polysulfide and a preparation method and application thereof, wherein the fluorescent probe is an organic small molecular compound based on coumarin derivatives, and the structural formula is as follows:
the fluorescent probe can respond to H with high selectivity and high sensitivity2SnIn H2SnIn the presence, the fluorescence spectrum shows obvious new emission peaks and can be used for H in solution and cells2SnThe method can greatly reduce the interference of external detection conditions, and has higher detection speed and higher detection precision.
Description
Technical Field
The invention relates to a fluorescent probe and a preparation method and application thereof, in particular to a fluorescent probe for detecting hydrogen polysulfide and a preparation method and application thereof, belonging to the technical field of chemistry.
Background
As hydrogen sulfide (H)2S) directly oxidized form, hydrogen polysulfide (H)2Sn，n>1) Has nucleophilicity, oxidation resistance, cell protection and oxidation reduction. Hydrogen polysulfide can participate in a series of redox regulation in cells, and is closely related to the physiological and pathological functions of the cells. In addition to this, more and more of the physiological activities involved by hydrogen sulfide are actually mediated by hydrogen polysulfide. In the case of endogenous hydrogen polysulfides, it is produced endogenously by oxidation of hydrogen sulfide by endogenous Reactive Oxygen Species (ROS). It is therefore reasonable to conclude that hydrogen sulfide is only a marker released during the physiological activity of hydrogen polysulfide, which may be the actual signal molecule. A thorough understanding of the production, distribution and physiological function of hydrogen polysulfides in normal and disease states is of great importance in elucidating cell signaling mechanisms.
Because of the diversity and complexity of the environment in the organism, it is of great research value and significance to develop an analytical method with high selectivity and sensitivity to detect hydrogen polysulfide. The visualization research supported by fluorescence bioimaging technology plays a very important role in the field of life analysis. The advantages of high sensitivity, controllable switch operation, good selectivity, high biocompatibility and the like of the fluorescent probe are utilized, and real-time in-situ detection and observation are easy to realize.
The fluorescent probe for detecting hydrogen sulfide based on the 2, 4-dinitrobenzene response group is used for detecting hydrogen sulfide, and the method mainly utilizes nucleophilicity of the hydrogen sulfide to open an ether bond connected between the 2, 4-dinitrobenzene group and a fluorophore so as to release the fluorescent group and further achieve the effect of fluorescence change. In a neutral environment, hydrogen polysulfide is more nucleophilic than hydrogen sulfide, meaning it has a greater offensive power. However, these fluorescent probes did not take hydrogen polysulfide into consideration in the selective study, and none of the test probes responded to hydrogen polysulfide. Therefore, it is important to explore the selectivity of this group for hydrogen polysulfide. Meanwhile, the development of the current fluorescent probe capable of being applied to detecting hydrogen polysulfide mainly focuses on the development of a fluorophore, and the development of a specific response group of hydrogen polysulfide is less, so that the development of a new hydrogen polysulfide response group has important research value and development prospect.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide a fluorescent probe for detecting hydrogen polysulfide and a preparation method and application thereof.
In order to achieve the above object, the present invention adopts the following technical solutions:
a fluorescent probe for detecting hydrogen polysulfide is characterized in that the fluorescent probe is an organic small molecular compound based on coumarin derivatives, and the structural formula of the fluorescent probe is shown as the formula I:
formula I.
The preparation method of the fluorescent probe for detecting hydrogen polysulfide is characterized by comprising the following steps:
(1) fully dissolving a coumarin derivative fluorophore in acetonitrile, then adding 2, 4-dinitrochlorobenzene, after dissolving, dropwise adding N, N-diisopropylethylamine into the mixed solution, and heating, condensing and refluxing for 2 hours at the temperature of 80 ℃ in an oil bath;
(2) after the completion of the reaction monitored by thin layer chromatography, the mixed solution was cooled to room temperature and filtered by suction to obtain a white solid, i.e., the aforementioned fluorescent probe.
The method for producing the coumarin derivative is characterized in that the molar ratio of the coumarin derivative fluorophore to the 2, 4-dinitrochlorobenzene to the N, N-diisopropylethylamine is 1:2: 1.5.
The use of the aforementioned fluorescent probe for detecting hydrogen polysulfide is characterized by being used for detecting hydrogen polysulfide in a solution and cells.
The application is characterized in that the fluorescent probe is dissolved in dimethyl sulfoxide to prepare 10mM stock solution, the stock solution is stored in a medicine shade cabinet at 4 ℃, and during detection, the stock solution of the fluorescent probe is diluted by the dimethyl sulfoxide, and the working concentration of the stock solution is 10 mu M.
The aforementioned use is characterized in that the detection is carried out at pH =7.4, a mixed solution of HEPES buffer solution and DMF is used as a reaction system, and the volume ratio of the HEPES buffer solution to DMF is 9: 1.
The invention has the advantages that:
(1) the fluorescent probe provided by the invention adopts coumarin derivatives as a fluorescent parent, selects 2, 4-dinitrobenzene containing electrophilic sites as a modulating group in a photoinduced electron transfer process, and can respond to H with high selectivity and high sensitivity2SnIn H2SnIn the presence of the fluorescent dye, a fluorescence spectrum shows obvious new emission peak and can be used for H2SnThe method can be used for qualitative detection and quantitative detection, can greatly reduce the interference of external detection conditions, and has higher detection speed and higher detection precision;
(2) the fluorescent probe provided by the invention has lower toxicity to cells and good biocompatibility, and can be used for detecting H in solution2SnAlso, H in cells can be detected2SnCan be used for further study H2SnThe dynamic mechanism of the processes of generation, transportation, accumulation and the like in the environment and organisms is also helpful for clarifying H2SnBiological effects in physiopathological Processes and Studies H2SnA new mechanism for dynamic balancing.
Drawings
FIG. 1 is a scheme showing the synthesis of a fluorescent probe of formula I;
FIG. 2 is the probe BCC detection H2SnSchematic diagram of (1);
FIG. 3 is a chart of probing probes BCC versus H2SnExperimental results plot of selectivity of (a);
FIG. 4 shows probes BCC and H2SnResponse to a time-varying ultraviolet absorption spectrum;
FIG. 5 shows probes BCC and H2SnA plot of fluorescence intensity in response to time;
FIG. 6 is a graph showing the results of a cytotoxicity study of probe BCC on HepG2 cells;
FIG. 7 shows the use of the probe BCC for detecting endogenous and exogenous addition of H in HepG2 cells2SnConfocal microscopy of (1).
Detailed Description
The invention is described in detail below with reference to the figures and the embodiments.
First part, structure of fluorescent probe for detecting hydrogen polysulfide and preparation method thereof
1. Structure of fluorescent probe
The fluorescent probe for detecting hydrogen polysulfide provided by the invention is an organic small molecular compound based on coumarin derivatives, and the structural formula is shown as formula I:
formula I
2. Preparation method of fluorescent probe
Referring to fig. 1, the method for preparing the fluorescent probe shown in formula I specifically includes the following steps:
(1) fully dissolving a coumarin derivative fluorophore (28 mg, 0.1 mmol) in acetonitrile, adding 2, 4-dinitrochlorobenzene (40 mg, 0.2 mmol), dissolving, dropwise adding N, N-diisopropylethylamine (20 mg, 0.15 mmol) into the mixed solution, and heating and condensing under reflux at 80 ℃ in an oil bath for 2 hours;
(2) after the completion of the reaction was monitored by thin layer chromatography, the mixture was cooled to room temperature and filtered with suction to obtain a white solid (42 mg, 93.8%), which was the fluorescent probe of formula I (denoted as probe BCC).
The nmr spectrum of the white solid was as follows:
1H NMR（500MHz，CDCl3-d1）δ（ppm）：9.15（s，1H），8.95（d，J=2.7Hz，1H），8.40（dd，J=9.2，2.7Hz，1H），8.16（d，J=9.1Hz，1H），8.09–7.97（m，2H），7.54（d，J=9.0Hz，1H），7.40（dd，J=8.8，2.3Hz，1H），7.13（d，J=9.2Hz，1H），4.47（q，J=7.1Hz，2H），1.44（t，J=7.1Hz，3H）；
13C NMR（500MHz，CDCl3-d1）δ（ppm）：163.36，156.74，155.22，154.22，143.88，142.21，135.63，132.40，131.10，129.03，128.17，122.35，119.69，119.30，117.20，117.11，112.06，62.32，29.69，14.28。
second part, principle of BCC probe for detecting hydrogen polysulfide
As shown in FIG. 2, when the hydrogen polysulfide is detected by probe BCC, the probe BCC reacts with the hydrogen polysulfide to generate the coumarin derivative fluorophore, which results in the change of fluorescence intensity.
A mixed solution of HEPES buffer solution and N, N-Dimethylformamide (DMF) was used as a reaction system to prepare a reaction mixture of 100. mu.M hydrogen polysulfide and 10. mu.M BCC probe. And (3) respectively measuring the fluorescence intensity of the solution at different time points (0-60 min), and then respectively drawing by taking the wavelength and the light intensity value as an abscissa and an ordinate. In the presence of hydrogen polysulfide, the fluorescence intensity of probe BCC is gradually weakened at 440nm, and a new fluorescence emission peak appears at 530nm and is gradually strengthened, so that ratio-type fluorescence detection of hydrogen polysulfide is realized, the interference of external detection conditions can be greatly reduced, and the detection precision is improved.
The probe BCC can be used for detecting the level of hydrogen polysulfide inside and outside cells, and has important biological value and significance for deeply researching the processes of generation, transportation, accumulation and the like of the hydrogen polysulfide in a living body.
Third portion, selectivity of probe BCC to hydrogen polysulfide and spectral response
1. Selectivity of probe BCC to hydrogen polysulfide
The probe BCC is dissolved in dimethyl sulfoxide (DMSO) to prepare a probe BCC stock solution with the concentration of 10mM, and the stock solution is stored in a medicine shade cabinet at 4 ℃. In the test, probe BCC stock solution is diluted with DMSO to a concentration of 1mM as stock solution for spectrum test to explore the ultraviolet and fluorescence spectrum properties of probe BCC to hydrogen polysulfide. Deionized water is used as a solvent to prepare various ion solutions (Mg) with the concentration of 10mM2+、Na+、Zn2+、Cl-) Amino acid solutions (Hcy, Cys, GSH, Tyr, Ala, Gly, Thr) and H2SnSolution, Na2S solution and Na2S2O3And (3) solution. To simulate physiological experiments, experiments were all performed at pH =7.4 (DMF-HEPES, pH =7.4, v/v = 9/1). Mixing the above solutions with probe BCC, wherein the final concentration of probe BCC is 10.0 μ M and the concentration of the sample is 100 μ M, shaking up the solution, balancing for 60min, and pouring the solution into a fluorescence dish to measure fluorescence spectrum.
The selectivity of probe BCC to hydrogen polysulfide is shown in FIG. 3. Wherein: 1, comparison; 2, Na2S；3，Na2S2O3；4，Mg2+；5，Zn2+；6，Na+；7，Cl-；8，Cys；9，Hcy；10，GSH；11，Tyr；12，Thr；13，Gly；14，Ala；15，H2Sn。
As can be seen from the experimental results of FIG. 3, the probes BCC are coupled to H2SnHas ideal selective response and can not be interfered by other sulfides, biological thiol, active biological molecules, ions and the like. That is, the probe BCC has good selectivity for hydrogen polysulfide under physiological pH conditions.
2. Spectral response of probe BCC to hydrogen polysulfide
Dissolving the probe BCC in dimethyl sulfoxide (DMSO) to prepare a probe BCC stock solution with the concentration of 10mM, storing the probe BCC stock solution in a medicine cooling cabinet at 4 ℃, and diluting the probe BCC stock solution with DMSO to the concentration of 1mM during testing. A mixed solution (DMF-HEPES, pH =7.4, v/v = 9/1) composed of a HEPES buffer solution and DMF is used as a reaction system to prepare a reaction mixed solution of 10 mu M probe BCC and 100 mu M hydrogen polysulfide, the prepared reaction mixed solution is poured into a fluorescent dish to measure fluorescence spectra at different time points (0-60 min), and the prepared reaction mixed solution is poured into an ultraviolet absorption dish to measure ultraviolet absorption spectra at different time points (0-60 min).
(1) Probe BCC versus time-varying UV-Vis of hydrogen polysulfide
Probe BCC in the presence of H2SnThe ultraviolet absorption spectrum after the treatment is shown in FIG. 4. FromAs can be seen in fig. 4:
(i) the probe BCC has maximum absorption at 338nm when the probes BCC and H2SnAfter (100 mu M) reaction, a new absorption peak gradually appears at 388nm, and meanwhile, the absorption peak of the probe at 338nm gradually weakens, and the ultraviolet absorption has obvious change along with the reaction time (0-60 min);
(ii) probe BCC pair H2SnThe reaction of (A) is substantially complete in 60min, and on H2SnHas good ultraviolet absorption selectivity and regularity.
(2) Time-dependent fluorescence spectrum of probe BCC to hydrogen polysulfide
Probe BCC fluorescence intensity with H2SnThe time-varying fluorescence spectrum is shown in FIG. 5. As can be seen from fig. 5:
(i) probes BCC and H2SnAfter the reaction, the fluorescence intensity at 440nm corresponding to the probe BCC is gradually reduced, and simultaneously the newly appeared fluorescence emission peak at 530nm is gradually enhanced along with the lapse of the reaction time;
(ii) the peak of the probe BCC at 440nm and the peak at 530nm both stabilized near the 60min reaction time.
The experimental results of fig. 4 and 5 show that: probe BCC pair H2SnHas good selectivity and can be completed within 60min, and the probe BCC is suitable for further research of cells and organisms.
Fourth, experimental verification of cell biocompatibility by probe BCC
The biological safety of the probe BCC is detected by using a Cell Counting Kit-8 (CCK-8) reagent. Human liver cancer cells (HepG 2) were selected as the experimental cell line, and HepG2 cells were cultured in a 96-well plate at 100. mu.L per well (3000 cells/. mu.L). After 24h of cell culture in 96-well plates, probe BCC (0. mu.M, 10. mu.M, 15. mu.M, 20. mu.M, 25. mu.M, 30. mu.M, 35. mu.M, 40. mu.M and 50. mu.M) was added to each of the groups and incubated for 12 h. Then 10. mu.L of CCK-8 (Cell Counting Kit-8) solution was added to each well and incubated in an incubator for 4 hours. And measuring the absorbance of the sample at the wavelength of 450nm by using a microplate reader, and reflecting the survival rate of the cells through the difference of the absorbance.
The results of the cytotoxicity study of probe BCC on HepG2 cells are shown in FIG. 6. As can be seen from fig. 6: the probe BCC has lower toxicity to HepG2 cells, the survival rate of the HepG2 cells can still reach over 95 percent when the concentration of the probe BCC reaches 20 mu M, and the influence of the probe BCC on the cell survival rate is negligible when the probe BCC is used in a cell experiment and is treated for a short time at a working concentration of 10 mu M.
That is, the BCC probe has low toxicity to cells and good biocompatibility, and can be explored in the next step.
Fifth part, Probe BCC for detection of Hydrogen polysulfide in cells
HepG2 cells were pre-cultured in a confocal dish for 24h to adhere to the wall, HepG2 cells were incubated with 10 μ M probe BCC for 60min as a control group, and laser confocal imaging was performed under a laser confocal microscope (405 nm excitation wavelength, 500nm to 600nm fluorescence collection), with the imaging results shown as a in FIG. 7; to another set of HepG2 cells, 100. mu.M H was added2SnTo provide exogenous hydrogen polysulfide, incubated in an incubator for 30min, and then incubated with 10 μ M probe BCC for 60min for confocal laser imaging under a confocal laser microscope, the imaging results are shown in b of fig. 7.
Comparing a and b in fig. 7 shows that: the former has weak intracellular fluorescence, and the latter has significantly enhanced intracellular fluorescence.
As can be seen, the probe BCC can be used to detect hydrogen polysulfide endogenous and exogenous to cells.
It should be noted that the above-mentioned embodiments do not limit the present invention in any way, and all technical solutions obtained by using equivalent alternatives or equivalent variations fall within the protection scope of the present invention.
Claims (6)
1. A fluorescent probe for detecting hydrogen polysulfide is characterized in that the fluorescent probe is an organic small molecule compound based on coumarin derivatives, and the structural formula of the fluorescent probe is shown as the formula I:
formula I.
2. The method of claim 1 for preparing a fluorescent probe for detecting hydrogen polysulfide, comprising the steps of:
(1) fully dissolving a coumarin derivative fluorophore in acetonitrile, then adding 2, 4-dinitrochlorobenzene, after dissolving, dropwise adding N, N-diisopropylethylamine into the mixed solution, and heating, condensing and refluxing for 2 hours at the temperature of 80 ℃ in an oil bath;
(2) and after the reaction is monitored by thin-layer chromatography, cooling the mixed solution to room temperature, and performing suction filtration to obtain a white solid, namely the fluorescent probe.
3. The method of claim 2, wherein the molar ratio of the coumarin derivative fluorophore, 2, 4-dinitrochlorobenzene, and N, N-diisopropylethylamine is 1:2: 1.5.
4. Use of a fluorescent probe for the detection of hydrogen polysulfide according to claim 1, characterized in that it is used for the detection of hydrogen polysulfide in solutions and cells.
5. The use of claim 4, wherein the fluorescent probe is dissolved in dimethyl sulfoxide to prepare a 10mM stock solution, the stock solution is stored in a cool and cool cabinet with medicines at 4 ℃, and the stock solution is diluted with dimethyl sulfoxide to have a working concentration of 10 μ M during detection.
6. The use according to claim 4, wherein the detection is carried out at pH =7.4, and a mixed solution of HEPES buffer solution and DMF is used as a reaction system, and the volume ratio of the HEPES buffer solution to DMF is 9: 1.
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