CN111808061B - Dual-channel fluorescent probe for distinguishing and detecting GSH and hydrogen polysulfide - Google Patents
Dual-channel fluorescent probe for distinguishing and detecting GSH and hydrogen polysulfide Download PDFInfo
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- CN111808061B CN111808061B CN202010668251.2A CN202010668251A CN111808061B CN 111808061 B CN111808061 B CN 111808061B CN 202010668251 A CN202010668251 A CN 202010668251A CN 111808061 B CN111808061 B CN 111808061B
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Abstract
The invention discloses a double channelDifferential detection of GSH and H2Sn(n>1) The fluorescent probe belongs to the technical field of chemical analysis and detection, and the molecular structural formula is as follows:
the probe emits green fluorescence after reacting with GSH, and H2SnAfter the reaction, red fluorescence was emitted. The probe can not only realize the detection of GSH and H2Sn(n>1) Meanwhile, the kit can distinguish detection, and has the characteristics of good selectivity, high sensitivity, wide pH working range and the like. Meanwhile, the probe can emit red fluorescence during detection and shows larger Stokes shift. These excellent properties indicate that the fluorescent probe has important application values in the fields of environment, biology and the like.
Description
Technical Field
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a two-channel simultaneous differential detection method for GSH and H2Sn(n>1) And the use of the probe in the detection of GSH and H2Sn(n>1) The use of (1).
Background
Active sulfur species (RSS) include Glutathione (GSH) and hydrogen polysulfide (H)2Sn，n>1) Plays an important role in regulating physiological and pathological processes of human bodies. GSH, as an antioxidant, protects cells from damage caused by harmful heavy metals, peroxides, and free radicals. Its abnormal level may cause diseases such as osteoporosis, cardiovascular disease and Alzheimer's disease. H2Sn(n>1) Exhibit high potency in regulating various physiological processes including activation of ion channels, transcription factors and tumor suppressors. In view of GSH and H2SnOf importance in redox biology, there is a great need to establish convenient detection methods for these species.
Fluorescent probes have become common methods for detecting biological thiols due to their advantages of convenient operation, nondestructive detection, high spatial-temporal resolution, and the like. In recent years, various methods have been developed for detecting GSH and H2Sn(n>1) The fluorescent probe of (1), but the probe of (2) is rarely capable of simultaneously detecting both of them separately. Chen et al (Analytical Chemistry, 2017,89(23),12984-2Sn(n>1) But the fluorescent probe emits light in the blue and green regions with a shorter wavelength. The red light or near infrared light has good organizationPenetrability, less background interference, and large stokes shift can reduce interference from self-absorption and autofluorescence to improve detection sensitivity. Currently, development of long wavelength emission and large stokes shift for differential detection of GSH and H2Sn(n>1) The fluorescent probes of (2) remain challenging.
Disclosure of Invention
To overcome the disadvantages of the prior art, it is an object of the present invention to provide a method for detecting GSH and H with high sensitivity and selectivity, and red light emission and large Stokes shift2Sn(n>1) The other purpose of the fluorescent probe is to provide a preparation method thereof.
The molecular structure of the fluorescent probe is as follows:
the fluorescent probe is prepared by the following reaction, and the synthesis process is as follows:
the specific synthesis method comprises the following steps: compound 4 and compound 8 are dissolved in anhydrous dichloromethane and 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 4-dimethylaminopyridine are added. Reacting at room temperature under the protection of nitrogen to obtain a crude product, and separating and purifying by silica gel column chromatography to obtain an orange yellow solid product, namely the probe.
The detection mechanism of the fluorescent probe of the invention is as follows:
when the fluorescent probe reacts with GSH, the site 1 is substituted by the sulfhydryl of the GSH, and green fluorescence is emitted. And H2SnDuring reaction, nucleophilic substitution reaction is firstly carried out on the probe site 1, then intramolecular cyclization reaction is carried out on the probe site 2, and red fluorescence is emitted.
H2S2Is the simplest hydrogen polysulfide species, and H2S2With other hydrogen polysulphides (H)2Sn，n>2) There is a dynamic equilibrium between them. Thus, this experiment was performed with H2S2Selection of Na for the subject2S2As H2SnThe source of (a).
The fluorescent probe is a dual-wavelength excitation type dual-channel distinguishing detection probe for detecting GSH and Na2S2In this case, the excitation wavelengths are set to correspond to the respective wavelengths. GSH-related test excitation wavelength set to 430nm, Na2S2The relevant test was set at 560 nm.
The maximum emission peak of the fluorescent probe of the invention after reaction with GSH is 530nm, and Na2S2The maximum emission peak after the reaction was 680 nm.
The fluorescent probe has good selectivity. The probe molecules were tested in 10mM PBS buffer containing 1.0mM CTAB at pH 7.4 at 25 ℃. After addition of 1.4 equivalent Glutathione (GSH), the fluorescence intensity increased 3-fold at the maximum emission wavelength of 530 nm. While adding other detection substances (NaCl, KCl, CaCl)2、ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、 Na2SO4、Na2S、H2O2L-Pro, L-Ser, L-Glu, DL-Tyr, Cys and Hcy), there was almost no increase in fluorescence.
The fluorescent probe has good selectivity. The probe molecules were tested in 10mM PBS buffer containing 1.0mM CTAB at pH 7.4 at 25 ℃. Adding 22 times of equivalent of sodium sulfide (Na)2S2) Thereafter, the fluorescence intensity at the maximum emission wavelength of 680nm increased by a factor of 27. While adding other detection substances (NaCl, KCl, CaCl)2、ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、 Na2SO4、Na2S、H2O2、L-Pro、L-Ser、L-Glu、DL-Tyr, Cys and Hcy), there was little increase in fluorescence.
The fluorescent probe has strong anti-interference capability and can be used for detecting other detection objects (NaCl, KCl and CaCl)2、 ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、Na2SO4、Na2S、H2O2L-Pro, L-Ser, L-Glu, DL-Tyr, Cys and Hcy) hardly affect the detection of Glutathione (GSH) and sodium persulfate (Na)2S2) The effect of (1).
After the fluorescent probe disclosed by the invention acts with Glutathione (GSH) added in an equivalent of 1.4 times respectively, the fluorescence is immediately enhanced and reaches a maximum value in 9 min. Adding 22 times of equivalent of sodium persulfate (Na)2S2) After this time, fluorescence immediately increased to a maximum at 30 min.
The fluorescent probe can be used for treating Glutathione (GSH) and sodium persulfate (Na)2S2) And respectively carrying out quantitative detection. The fluorescent probe has good linearity, and the linear correlation coefficients are respectively as follows: glutathione (GSH) R ═ 0.9994, sodium persulfate (Na)2S2)R＝0.9945。
The fluorescent probe has good cell membrane penetrability, and can be used for Glutathione (GSH) and sodium persulfate (Na) in cells2S2) Detection of (3).
The probe has wide pH application range, and can detect pH 7.0 to pH 10.0.
The probe molecule of the invention is sodium persulfate (Na)2S2) And has red light emission after response and larger Stokes shift. The Stokes shifts are 100nm and 120nm, respectively.
Drawings
Fig. 1 shows the change of fluorescence spectrum of the fluorescent probe of the present invention (10.0 μ M) after reacting with Glutathione (GSH) at different concentrations in a PBS buffer solution (10mM, pH 7.4, 1.0mM CTAB), with the wavelength on the abscissa and the fluorescence intensity on the ordinate.
FIG. 2 is a linear relationship of fluorescence intensity at 530nm with concentration during the action of the fluorescent probe of the present invention (10.0. mu.M) with Glutathione (GSH) in PBS buffer (10mM, pH 7.4, 1.0mM CTAB), with concentration on the abscissa and fluorescence intensity on the ordinate.
FIG. 3 shows fluorescent probes of the invention (10.0. mu.M) in PBS buffer (10mM, pH 7.4, 1.0mM CTAB) with different concentrations of sodium peroxosulfide (Na)2S2) The fluorescence spectrum after the action changes, the abscissa is the wavelength, and the ordinate is the fluorescence intensity.
FIG. 4 shows the reaction of the fluorescent probe of the present invention (10.0. mu.M) with sodium persulfate (Na) in PBS buffer (10mM, pH 7.4, 1.0mM CTAB)2S2) In the action process, the linear relation of the fluorescence intensity at 680nm along with time is shown, the horizontal coordinate is concentration, and the vertical coordinate is fluorescence intensity.
FIG. 5 shows the selectivity of the fluorescent probes of the present invention in PBS buffer (10mM, pH 7.4, 1.0mM CTAB) with GSH and other analytes (NaCl, KCl, CaCl)2、ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、Na2SO4、Na2S、 H2O2The ratio of fluorescence intensities (I) after the actions of L-Pro, L-Ser, L-Glu, DL-Tyr, Cys and Hcy)Probe+others/IProbe) A histogram.
FIG. 6 shows the selectivity of the fluorescent probe of the present invention in PBS buffer (10mM, pH 7.4, 1.0mM CTAB) and Na (10.0. mu.M)2S2And other analytes (NaCl, KCl, CaCl)2、ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、Na2SO4、Na2S、 H2O2The ratio of fluorescence intensities (I) after the actions of L-Pro, L-Ser, L-Glu, DL-Tyr, Cys and Hcy)Probe+others/IProbe) A histogram.
FIG. 7 is a graph showing interference resistance of the fluorescent probe of the present invention, Glutathione (GSH) and analytes (NaCl, KCl, CaCl)2、ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、Na2SO4、 Na2S、H2O2L-Pro, L-Ser, L-Glu, DL-Tyr, Cys and Hcy) in the presence of a fluorescent probe (10.0. mu.M) reacted with Glutathione (GSH) in PBS buffer (10mM, pH 7.4, 1.0mM CTAB)Probe+others+GSH/IProbe+GSH) A histogram.
FIG. 8 shows the interference resistance of the fluorescent probe of the present invention, sodium peroxosulfide (Na)2S2) With analytes (NaCl, KCl, CaCl)2、ZnCl2、MgCl2、NaClO、Na2S2O3、Na2SO3、NaHSO3、Na2SO4、 Na2S、H2O2L-Pro, L-Ser, L-Glu, DL-Tyr, Cys and Hcy) were combined with fluorescent probe in PBS buffer (10.0. mu.M, pH 7.4, 1.0mM CTAB) and sodium persulfate (Na) in the presence of the fluorescent probe2S2) Fluorescence intensity ratio (I) after EffectProbe+others+Na2S2/IProbe+Na2S2) A histogram.
FIG. 9 shows the change of fluorescence intensity at 530nm with time during the reaction of the fluorescent probe (10.0. mu.M) of the present invention with Glutathione (GSH) in PBS buffer (10mM, pH 7.4, 1.0mM CTAB), with time on the abscissa and fluorescence intensity on the ordinate.
FIG. 10 shows the fluorescent probe of the present invention (10.0. mu.M) in PBS buffer (10mM, pH 7.4, 1.0mM CTAB) with sodium persulfate (Na)2S2) The change of the fluorescence intensity at 680nm along with time in the action process, the abscissa is time, and the ordinate is the fluorescence intensity.
FIG. 11 shows fluorescence intensities of a fluorescent probe (10.0. mu.M) of the present invention before and after the interaction with Glutathione (GSH) in PBS buffer solutions of different pH values, with pH on the abscissa and fluorescence intensity on the ordinate.
FIG. 12 shows the reaction of fluorescent probes (10.0. mu.M) of the present invention with sodium persulfate (Na) in PBS buffer solutions of different pH values2S2) Fluorescence intensity before and after the action, the abscissa is pH, and the ordinate isThe coordinates are fluorescence intensity.
FIG. 13 shows the fluorescent probe of the present invention for detecting Glutathione (GSH) and sodium persulfate (Na) in RAW264.7 cells2S2) Confocal cell imaging. A1-A3 is the imaging effect of cells incubated with probes (10.0. mu.M) at 37 ℃ for 30 minutes. B1-B3 is the reaction of cells with sodium persulfate (Na) at 37 deg.C2S2) Imaging was performed by incubation at (220.0. mu.M) for 15 min and then with probe (10.0. mu.M) for 30 min. C1-C3 is the imaging effect of cells pretreated with N-ethylmaleimide (1mM) for 15 minutes at 37 ℃ and then incubated with probe (10.0. mu.M) for 30 minutes.
FIG. 14 shows the fluorescent probe of the present invention for detecting endogenous sodium persulfate (Na) in RAW264.7 cells2S2) Confocal cell imaging. A1-A3 is the imaging effect of cells incubated with Lipopolysaccharide (LPS) (1. mu.g/mL) for 8 hours at 37 ℃, then NEM (1mM) for 15 minutes, then cystine (200. mu.M) for 30 minutes, and finally probe (10.0. mu.M) for 30 minutes. B1-B3 is the imaging effect of cells treated with NEM (1mM) for 15 min at 37 ℃, then incubated with cystine (200. mu.M) for 30min, and finally incubated with probe (10.0. mu.M) for 30 min.
Detailed description of the preferred embodiment
Example 1: synthesis of Compound 2
Resorcinol (7.707g, 70.0mmol) and compound 1(0.979g, 3.5mmol) were dissolved in 10.0 mL acetonitrile and the mixture was stirred at 0 ℃ for 5 min. Sodium chlorite (1.112g, 12.3mmol) and sodium dihydrogen phosphate (1.896g, 15.8 mmol; dissolved in 1.5mL of water) were added to the above mixture. After stirring the reaction at 0 ℃ for 30 minutes, it was poured into 50mL of ice water. The mixture was acidified with 1mol/L hydrochloric acid solution to form a large amount of yellow precipitate. After washing with suction filtration and drying under vacuum, 0.751g of a tan solid was obtained as compound 2, yield: 76.2 percent.
Example 2: synthesis of Compound 3
Diphenyldiselenide (0.218g, 0.7mmol) and sodium borohydride (0.034g, 0.9mmol) were dissolved in 2.5mL of anhydrous ethanol. The mixture was stirred at room temperature for 10 minutes under nitrogen to give compound 3 as a colorless transparent solution. The product of the step can be directly used for the next step without purification.
Example 3: synthesis of Compound 4
Compound 2(0.180g, 0.6mmol) was dissolved in anhydrous N, N-dimethylformamide (5.0mL), and triethylamine (240.0. mu.L, 1.8mmol) was added as an acid-binding agent. Compound 3(0.110g, 0.7mmol) was then added and the reaction stirred at room temperature for 20 minutes. The mixture was then poured into 50mL of water and extracted with dichloromethane, the organic phase being retained. The organic solvent was removed under reduced pressure to give 0.243g of an orange solid as compound 4 in 98.0% yield.
Example 4: synthesis of Compound 6
Compound 5(2.018g, 12.6mmol) was weighed out and dissolved in 15.0mL of acetic anhydride, and malononitrile (1.413g, 21.4mmol) was added after stirring well. The solution was heated to 140 ℃ and reacted for 10 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and then 30.0mL of methanol was added. The reaction was stirred for 30 minutes while the temperature was raised to 50 ℃. The reaction mixture was spin dried to afford the crude product. The crude product was purified by column chromatography on silica gel (100-200 mesh) eluting with petroleum ether/dichloromethane (vol: 5/1). 1.031g of an orange solid is obtained as compound 6, 39.3% yield.
Example 5: synthesis of Compound 8
Compound 6(0.937g, 4.5mmol) and compound 7(0.611g, 5.0mmol) were dissolved in 15.0mL of toluene as a solvent, and after stirring well, 600.0. mu.L of acetic acid and 1.5mL of piperidine were added in this order. Under the protection of nitrogen, the reaction solution is heated to 112 ℃ for reflux, and stirred for reaction for 6 hours. After the reaction was completed, the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (100-200 mesh) eluting with dichloromethane/ethyl acetate (vol: 10/1). 0.600g of red solid was obtained as compound 8 in 42.7% yield.
Example 6: synthesis of Probe
Compound 4(0.835g, 2.0mmol), compound 8(0.687g, 2.2mmol), 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.421g, 2.2mmol) and 4-dimethylaminopyridine (0.269g, 2.2mmol) were each weighed out and dissolved in 5.0mL of dichloromethane. The reaction was carried out at room temperature for 5 hours under nitrogen protection. After the reaction was completed, the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (100-200 mesh) eluting with dichloromethane/ethyl acetate (vol: 10/1). 0.745g of an orange solid was obtained as a probe in 52.4% yield.
Example 7: probe molecule detection of Glutathione (GSH) and sodium sulfide (Na) in cell2S2) Application of
Endogenous GSH detection: RAW264.7 cells were first incubated with PBS buffer containing probes (10. mu.M) for 30 minutes. After washing the cells with PBS buffer for 3 times, the cell fluorescence imaging experiment was performed with a laser confocal fluorescence microscope. A green fluorescence signal can be observed, and the detection of the endogenous GSH of the cells is realized.
Exogenous Na2S2And (3) detection: RAW264.7 cells were first mixed with Na-containing cells2S2Incubate (220. mu.M) in PBS buffer for 15 minutes. The cells were then rinsed 3 times with PBS buffer and incubated with PBS buffer containing probes (10. mu.M) for 30 minutes. The cells were rinsed 3 times with PBS buffer and subjected to a cell fluorescence imaging experiment. Can observe red fluorescence signal to realize Na in cells2S2And (6) detecting.
Control experiment: RAW264.7 cells were pretreated for 15 minutes with N-ethylmaleimide (NEM, 1mM) in PBS buffer. The cells were then rinsed 3 times with PBS buffer and incubated with PBS buffer containing probes (10. mu.M) for 30 minutes. Finally, the cells were rinsed 3 times with PBS buffer for cytofluorescence imaging experiments. Neither the green channel nor the red channel had a significant fluorescence signal.
Example 8: probe molecule for detecting endogenous sodium persulfate (Na) in cells2S2) Application of
Endogenous Na2S2And (3) detection: RAW264.7 cells were incubated with 1. mu.g/mL Lipopolysaccharide (LPS) in PBS buffer for 8 hours. Then, the cells were rinsed 3 times with PBS buffer and pretreated for 15 minutes with PBS buffer containing NEM (1 mM). Next, the cells were rinsed 3 times with PBS buffer and incubated with cystine (200. mu.M) in PBS buffer for 30 minutes. Finally, the cells were rinsed 3 times with PBS buffer and incubated with PBS buffer containing probes (10. mu.M) for 30 minutes. By PAfter the cells were rinsed 3 times with BS buffer, the cell fluorescence imaging experiment was performed. Can observe red fluorescence signal to realize endogenous Na2S2And (6) detecting.
Control experiment: cells were first pretreated with NEM (1mM) in PBS buffer for 15 min. Then, the cells were rinsed 3 times with PBS buffer, and the cells were incubated with cystine (200. mu.M) containing PBS buffer for 30 minutes. Finally, the cells were rinsed 3 times with PBS buffer and incubated with PBS buffer containing probes (10. mu.M) for 30 minutes. After the cells were rinsed 3 times with PBS buffer, the cell fluorescence imaging experiment was performed. No significant fluorescence signal was generated.
Claims (1)
1. A dual-channel fluorescent probe for distinguishing and detecting GSH and hydrogen polysulfide has a structural formula as follows:
the detection system of the fluorescent probe comprises 10mM PBS buffer solution with pH 7.4 and 1.0mM CTAB, and the fluorescent probe is detected at 25 ℃; the maximum emission wavelengths of the fluorescent probes for detecting GSH and hydrogen polysulfide are 530nm and 680nm respectively.
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