CN110950877B - Double-detection fluorescent probe, preparation method and application thereof in detection of hydrogen sulfide and copper ions - Google Patents
Double-detection fluorescent probe, preparation method and application thereof in detection of hydrogen sulfide and copper ions Download PDFInfo
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Abstract
The invention provides a double-detection fluorescent probe, which has the molecular formula as follows: c43H39N9O5The preparation method of the probe comprises the following steps: dissolving the compound 2 in dry DMF, adding HOBt and EDCI at room temperature, stirring at room temperature for 30 min, adding the compound 1, stirring at room temperature overnight, after complete reaction, extracting and separating, removing the solvent to obtain a crude product, and separating by using a silica gel column to obtain the probe molecule. The probe can be applied to chemical sensing detection of hydrogen sulfide and copper ions in water environment and cells; the sensing detection comprises fluorescence detection, visual qualitative detection and cell imaging detection. The probe can be used for respectively detecting hydrogen sulfide and copper ions in cells and generating different fluorescent signals.
Description
Technical Field
The invention relates to a preparation method of a fluorescent probe capable of respectively detecting hydrogen sulfide and copper ions in cells by using a single molecular probe, belonging to the technical field of analytical chemistry.
Background
Hydrogen sulfide (H)2S) is the third cellular signaling molecule found after NO and CO, which plays a very important role in the human nervous system. In addition, hydrogen sulfide plays an extremely important role in regulating human physiological functions, for example, hydrogen sulfide can participate in hemoglobin modification, reduction of nitroso compounds in vivo, regulation of functions of various enzymes in vivo, and the like. Furthermore, abnormalities in hydrogen sulfide concentration have been shown to be closely related to numerous diseases, such as cirrhosisAlzheimer's disease, diabetes and Down's syndrome. The hydrogen sulfide also has the functions of efficiently regulating myocardial contractility, relaxing blood vessels, and stably and bidirectionally regulating blood pressure. The hydrogen sulfide can effectively remove hydrogen peroxide, superoxide anion, hypochlorous acid, peroxynitroso and the like. Therefore, the method has extremely important significance for detecting the concentration of the hydrogen sulfide in the organism.
Copper ions are a third type of trace element essential to the human body in addition to iron and zinc ions. Copper ions play an important role in a variety of physiological processes, and copper deficiency can lead to disturbances in growth and metabolism. Abnormal copper concentration in cells can lead to inhibition of neurological diseases such as Menkes 'syndrome, Wilson's disease, familial hereditary sclerosing of the spinal cord, Alzheimer's disease, and Prion's disease. The detection of copper ions by means of fluorescent molecular probes becomes a significant matter.
However, a single fluorescent probe for respectively detecting hydrogen sulfide and copper ions under different wave bands is lacked at present, and aiming at the current requirements, a fluorescent probe capable of respectively detecting hydrogen sulfide and copper ions in cells under different wavelengths is designed and synthesized, so that the problem of lacking of a detection tool for researching hydrogen sulfide and copper ions in cells is solved.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a double-detection fluorescent probe, a preparation method and application thereof in detecting hydrogen sulfide and copper ions, and the following aims are achieved:
(1) the catalyst has good selectivity to hydrogen sulfide and copper ions;
(2) intracellular hydrogen sulfide and copper ions can be detected separately.
In order to solve the technical problems, the invention adopts the following technical scheme:
the molecular structural formula of the designed fluorescent probe is as follows:
the fluorescent probe prepared by the invention is called D-CN, and the D-CN refers to the fluorescent probe with the structural formula below.
The synthetic route of the hydrogen sulfide and copper ion dual-detection fluorescent probe is as follows:
the synthesis of probe D-CN can be carried out in one step, wherein compounds 1 and 2 have been reported in the literature:
The preparation steps of the probe D-CN are as follows:
The molar ratio of the compound 2 to the compound 1 is 1.2: 1;
the molar ratio of the HOBt to the compound 1 is 1.2: 1;
the molar ratio of EDCI to compound 1 is 1.2: 1;
the molar volume ratio of the compound 2 to DMF is 0.511 mmol: 6 ml;
the application of the D-CN probe of the invention is as follows: the fluorescent probe can be applied to the respective sensing detection of the hydrogen sulfide and copper ion contents in water environment and biological cells; the sensing detection comprises fluorescence detection, visual qualitative detection and cell imaging detection.
Compared with the prior art, the invention has the beneficial effects that:
(1) the fluorescence detection of a single probe on various target molecules (hydrogen sulfide and copper ions) is realized, and in addition, different signals can be generated under different wavelengths for different target molecules;
the fluorescence detection is carried out, wherein when the molar ratio of H2S to D-CN is 0.9-10:1, the fluorescence intensity a.u. at 530nm is 200-;
The fluorescence intensity a.u. at 580nm is 60-1300 when the molar ratio of copper ions to D-CN is 0.9-10: 1.
(2) The invention realizes the selective specificity to hydrogen sulfide and copper ions and strong anti-interference ability of other molecules.
(3) The probe can be applied to detecting hydrogen sulfide and copper ions in cells, wherein the hydrogen sulfide can be imaged in a green channel under a fluorescence microscope, and the copper ions can be imaged in a red channel under the microscope, so that the probe has good signal resolution, and the direct interference of signals is reduced.
(4) The probe can obviously change the colors of hydrogen sulfide and copper ions in an aqueous solution, can show green light for the hydrogen sulfide in the aqueous solution and yellow light for the copper ions in the aqueous solution under the condition of irradiation of a hand-held ultraviolet lamp, and can carry out real-time qualitative visual colorimetry detection. Therefore, the invention is a simple, rapid and sensitive detection reagent for the specificity of the hydrogen sulfide and copper ions, and has wide application prospect in the field of biomolecule detection. The performance of which will be described in detail in the examples with reference to the accompanying drawings.
Drawings
FIG. 1 shows the preparation of probe D-CN in example 1 1An H NMR spectrum;
FIG. 2 is a fluorescent spectrum of probe D-CN after addition of hydrogen sulfide;
FIG. 3 is a fluorescent spectrum of probe D-CN after the addition of copper ions;
FIG. 4 is a bar graph of selectivity of probe D-CN to hydrogen sulfide at 530 nm;
FIG. 5 is a bar graph of the selectivity of probe D-CN to copper ions at 580 nm;
FIG. 6 is a graph showing the color change of the solution before and after addition of hydrogen sulfide and copper ions for probe D-CN under room light;
FIG. 7 is a graph showing the change in fluorescence color of the solution before and after addition of hydrogen sulfide and copper ions under ultraviolet light for the probe D-CN;
FIG. 8 is a graph of fluorescence imaging of hydrogen sulfide and copper ions with probe D-CN applied to cells;
wherein a-c are a bright field, green channel fluorescence imaging map and an overlay of the HeLa cells in the presence of only the fluorescent probe D-CN (5 mu M); d-f is a fluorescence imaging graph and an overlapping graph of a fluorescent probe D-CN (5 mu M) added into the HeLa cell and sodium sulfide (20 mu M) added into the HeLa cell in a bright field and a green channel; g-i is a bright field, red channel fluorescence imaging graph and an overlapping graph of the HeLa cells in the presence of only the fluorescent probe D-CN (5 mu M); j-l is a fluorescence imaging graph and an overlapping graph of a bright field and a green channel by adding copper chloride (20 mu M) after adding a fluorescent probe D-CN (5 mu M) into the HeLa cell.
Detailed Description
The invention is further illustrated by the following examples and figures, but is not limited by the following examples, which are numbers of compounds in the examples that are given in relation to the numbers of compounds in the schemes above.
The Chinese names of DMF, HOBt and EDCI are respectively N, N-dimethylformamide, 1-hydroxybenzotriazole,
1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride.
Example 1: synthesis procedure for Probe D-CN
Compound 2 (0.511 mmol) was dissolved in 6 mL of dry DMF, HOBt (0.511 mmol) and EDCI (0.511 mmol) were added at room temperature, and after stirring (1000 rpm) at room temperature for 30 min, compound 1 (0.426 mmol) was added to the system.
Stirring at room temperature (1000 r/min) overnight, detecting reaction by TLC plate, after reaction is completed, pouring the reaction solution into 20 mL water, extracting with 90mL ethyl acetate for three times, and combining three organic phases to obtain extract; the combined extracts were washed with water and brine (washing with a separatory funnel, separation of layers), the organic phase was dried over anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure to give a crude product, which was separated with a silica gel column, the silica gel particle size was 200-300 mesh, and the product D-CN 240 mg was obtained by eluting with an eluent (ratio dichloromethane/methanol =30: 1), the yield was 74%, calculated as Compound 1.
The above-mentioned yield was calculated by calculating the theoretical mass of the product of the complete reaction based on the number of moles of the compound 1 and dividing the mass of the product obtained by the theoretical mass of the product.
The end of the reaction was judged by checking on a TLC plate, and the end of the reaction was hardly checked in the case of Compound 1.
The prepared product has a hydrogen nuclear magnetic resonance spectrum as follows:
1H-NMR (400 MHz, DMSO-d 6) 8.55 (dd, J = 7.4, 1.2 Hz, 1H), 8.49 (d, J = 8.0 Hz, 1H), 8.44 (dd, J = 8.5, 1.2 Hz, 1H), 7.88 (dd, J = 8.5, 7.3 Hz, 1H), 7.82 – 7.72 (m, 2H), 7.49 (td, J = 6.0, 5.0, 3.4 Hz, 2H), 7.04 – 6.94 (m, 1H), 6.76 – 6.61 (m, 2H), 6.41 (d, J = 8.7 Hz, 1H), 6.36 (d, J = 5.4 Hz, 3H), 4.35 (s, 2H), 4.26 (t, J = 7.8 Hz, 2H), 3.60 (d, J = 5.5 Hz, 4H), 3.32 (t, J= 7.1 Hz, 5H), 3.28 – 3.10 (m, 6H), 2.75 (d, J = 8.1 Hz, 3H), 1.09 (t, J = 6.9 Hz, 6H);HRMS (ESI) m/z calcd for C43H40N9O5 [M+H]+: 762.3152; Found 762.3145.
example 2 application of fluorescent Probe D-CN in fluorescence detection of Hydrogen sulfide and copper ions
(1) Preparation of D-CN stock solution
7.6 mg of the D-CN solid prepared in example 1 is weighed and placed in a 10 mL volumetric flask, dissolved with DMF and brought to a volume of 10 mL to obtain a 1 mmol/L stock solution of D-CN.
(2) Dilution of water
Preparing 12 centrifuge tubes with the number of 1-12, taking out 30 mu L of centrifuge tubes from the stock solution, adding the centrifuge tubes into 12 centrifuge tubes, and diluting the centrifuge tubes with 2mL of 30% DMF and PBS buffer solution (0.1mol/L, pH = 7.4);
the 30% DMF and PBS means that the volume ratio of DMF to PBS is 30: 70.
(3) Adding H2S standard solution
Adding H2S standard solutions with different equivalents into a No. 1-12 centrifuge tube, and gradually increasing from 0 equivalent by 0.9 equivalent each time; that is, the H2S standard solution is not added into the No. 1 centrifuge tube, the amount of the H2S standard solution added into the No. 2 centrifuge tube is gradually increased, and the molar ratio of the H2S to the D-CN in the No. 2 centrifuge tube to the No. 12 centrifuge tube is 0.9:1, 1.8:1, 2.7:1, 3.6:1, 4.5:1, 5.4:1, 6.3:1, 7.2:1, 8.1:1, 9.0:1 and 9.9:1 respectively.
In FIG. 2, the fluorescence spectrum corresponds to centrifuge tubes 1-12 from bottom to top.
The above equivalent means H2The molar ratio of S to D-CN;
(4) constant volume
Diluting to 3 mL by using 30% DMF and PBS buffer solution;
(5) measuring fluorescence spectra
The change of the fluorescence spectrum (as shown in figure 2) is measured and excited at 440 nm, and the D-CN probe solution is shown to be accompanied by sodium sulfide (H)2S donor), the fluorescence peak at 530 nm gradually increased.
The same method can measure the fluorescence spectrum of the response of copper ions as shown in FIG. 3, and the fluorescence peak at 580 nm gradually increases with the increase of the copper ion concentration of the probe solution when the probe solution is excited by light at 530 nm. Therefore, the fluorescent probe can respectively respond to hydrogen sulfide and copper ions under different wavelengths to generate different response signals.
Example 3 Probe D-CN Selective test on Hydrogen sulfide at 530 nm
Taking out 30 mu L of the fluorescent probe stock solution in example 2, respectively adding the 30 mu L of the fluorescent probe stock solution into 19 centrifuge tubes with the volume of 5mL, diluting the mixture with 2 mL of PBS buffer solution containing 30% DMF, then respectively adding competitive molecule standard solutions into 17 centrifuge tubes, taking one of the competitive molecule standard solutions as a blank sample and adding hydrogen sulfide standard solution into the other centrifuge tube;
The molar ratio of the added hydrogen sulfide to the D-CN is 10: 1;
the molar ratio of the addition amount of the competitive molecules to the D-CN is 10: 1;
and (3) diluting the solution to 3mL by using 30% DMF and PBS buffer solution, reacting for 15 min, detecting the change of fluorescence emission spectrum of the solution, and performing spectrum test by using 440 nm as excitation light. As shown in figure 4, the probe has good selectivity on hydrogen sulfide at 530nm, other interferents hardly affect the spectrum of the probe, and the fluorescence spectrum of the probe at 530nm is obviously enhanced only after the hydrogen sulfide is added. Indicating that the probe has good selectivity for hydrogen sulfide at 530 nm.
Example 4: probe D-CN selectivity test for copper ions at 580nm
30 μ L of the fluorescent probe stock solution in example 2 was taken out and added into 17 centrifuge tubes of 5mL, and after diluting with 2 mL of PBS buffer solution containing 30% DMF, the interfering metal ions and molecules were added into 15 centrifuge tubes, one of the tubes was used as a blank sample, and no interfering substance was added, and the copper ion standard solution was added to one of the tubes. The volume is adjusted to 3mL by 30% DMF PBS buffer solution, and the change of fluorescence emission spectrum of the solution is detected after the reaction is carried out for 15 min. The spectral measurement was carried out with 550 nm as excitation light. As shown in FIG. 5, only the emission spectrum of the sample added with copper ions has obvious change, and other interfering ions can not change the spectrum of the probe at 580nm, which shows that the probe has good selectivity for copper ions at 580 nm.
The molar ratio of the addition amount of the interference metal ions and molecules to the D-CN is 10: 1;
the molar ratio of the addition amount of the copper ions to the D-CN is 10: 1.
Example 5: application of probe D-CN solution in visual qualitative detection of hydrogen sulfide and copper ions
2 ml of the stock solution of the fluorescent probe in example 2 was taken out and added to three cuvettes, the first cuvette was blank and nothing was added, the second cuvette was added with 10 molar equivalents of standard solution of sodium sulfide, the third cuvette was added with 10 molar equivalents of standard solution of copper chloride, and as a result of the experiment, it was found that the solution had a significant color change, the blank solution was colorless, the solution added with sodium sulfide appeared pale yellow, and the solution added with copper ions appeared pale red (fig. 6). With the irradiation of an ultraviolet lamp, the fluorescence emitted by the solution can be observed by naked eyes to be obviously changed, the blank solution presents light green, the solution added with sodium sulfide presents dark green, and the solution added with copper sulfide presents yellow (figure 7), which shows that D-CN is a fluorescent probe capable of visually distinguishing hydrogen sulfide from copper ions and realizing the distinguishing of hydrogen sulfide from copper ions by naked eyes.
Example 6: application of probe D-CN in imaging detection of hydrogen sulfide and copper ion cells
The application of the fluorescent probe D-CN obtained by the invention in HeLa cells for carrying out fluorescence imaging on hydrogen sulfide and copper ions comprises the following specific operation steps:
a5 μ L D-CN fluorescent probe was removed from the fluorescent probe stock solution of example 2, added to three HeLa cell-grown culture dishes (of which there was 1mL of cell culture medium), and the dishes were numbered. Adding 2 muL of PBS buffer solution into the first culture dish serving as a reference sample; 2 mu L of 10 mM sodium sulfide standard solution is added into the second culture dish. After incubation in a carbon dioxide incubator for 30 min, imaging was performed using a confocal microscope. And adding 2 mu L10 mM copper chloride standard solution into the third culture dish, culturing for 30 min in a carbon dioxide incubator, imaging by using a confocal microscope, and imaging the first culture dish at first. Fluorescence imaging of cells with green (500 nm-550 nm) and red (570 nm-620 nm) channels with 488 nm and 561 nm lasers, respectively, showed that in cells in a dish with only probe, no fluorescence was observed in both channels. Fluorescence emission can be observed in green channels in cells in a culture dish added with sodium sulfide; fluorescence emission was detected in the red channel in cells in a petri dish with copper chloride added; the D-CN fluorescent probe can perform fluorescence imaging on hydrogen sulfide and copper ions in different channels in cells.
Claims (6)
1. A dual detection fluorescent probe, characterized in that: the molecular formula of the probe is as follows: c43H39N9O5；
The structural formula of the probe is as follows:
；
the preparation method of the probe comprises the following steps: synthesizing the compound 1 and the compound 2 to obtain a fluorescent probe;
the structural formula of the compound 1 is as follows:
；
the structural formula of the compound 2 is as follows:
；
the preparation method of the probe comprises the following steps: dissolving the compound 2 in dry DMF, adding HOBt and EDCI at room temperature, stirring at room temperature for 30 min, adding the compound 1, stirring at room temperature overnight, after complete reaction, performing extraction separation, removing the solvent to obtain a crude product, and separating by using a silica gel column to obtain probe molecules;
the molar ratio of the compound 2 to the compound 1 is 1.2: 1; the molar ratio of the HOBt to the compound 1 is 1.2: 1; the molar ratio of EDCI to compound 1 is 1.2: 1; the molar volume ratio of the compound 2 to DMF is 0.511 mmol: 5-8 ml.
2. The use of the dual detection fluorescent probe of claim 1 in the preparation of a fluorescent probe for detecting hydrogen sulfide and copper ions, wherein:
the probe can be applied to chemical sensing detection of hydrogen sulfide and copper ions in water environment and cells; the chemical sensing detection is fluorescence detection.
3. The use of a dual detection fluorescent probe according to claim 1 in the preparation of a fluorescent probe for the detection of hydrogen sulfide and copper ions, wherein:
the probe can be applied to chemical sensing detection of hydrogen sulfide and copper ions in water environment; the chemical sensing detection is visual qualitative detection.
4. The use of the dual detection fluorescent probe of claim 1 in the preparation of a fluorescent probe for detecting hydrogen sulfide and copper ions, wherein:
the probe can be applied to water environment and intracellular chemical sensing detection of hydrogen sulfide and copper ions; the chemical sensing assay is a cellular imaging assay.
5. The use of the dual detection fluorescent probe of claim 2 in the preparation of a fluorescent probe for detecting hydrogen sulfide and copper ions, wherein: the fluorescence detection, H2When the molar ratio of S to the fluorescent probe is 0.9-10:1, the fluorescence intensity a.u. at 530nm is 200-1900;
when the molar ratio of the copper ions to the fluorescent probe is 0.9-10:1, the fluorescence intensity a.u. at 580nm is 60-1300.
6. The use of the dual detection fluorescent probe of claim 3 in the preparation of a fluorescent probe for detecting hydrogen sulfide and copper ions, wherein: the visual qualitative detection, H 2When the molar ratio of S to the fluorescent probe is 10:1, the solution is light yellow under indoor light, and is dark green under 365nm ultraviolet irradiation;
when the molar ratio of the copper ions to the fluorescent probe is 10:1, the solution is light red under indoor light, and is yellow under 365nm ultraviolet irradiation.
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| CN110950877A (en) | 2020-04-03 |
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