CN110642857B - Difunctional fluorescent probe for detecting viscosity and pH, and preparation and application thereof - Google Patents
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N2021/6417—Spectrofluorimetric devices
- G01N2021/6421—Measuring at two or more wavelengths
Abstract
The invention discloses a bifunctional fluorescent probe for detecting viscosity and pH, and preparation and application thereof, wherein the structural formula of the bifunctional fluorescent probe is shown as a formula I:
the bifunctional fluorescent probe is used for detecting viscosity and pH in solution or cells. The invention prepares and provides a bifunctional probe capable of detecting viscosity and pH; the solution viscosity can be quantitatively detected; can be used for detecting the change of the viscosity and the pH value in the cell and provides a new detection technical means for researching the physiological action of the viscosity and the pH value in the cell.
Description
Technical Field
The invention relates to the field of fluorescent probes, in particular to a difunctional fluorescent probe for detecting viscosity and pH as well as a preparation method and application thereof.
Background
The stability of intracellular fluids is the basis for normal activity of living cells, and abnormal changes in intracellular fluids are associated with a number of dysfunctions and diseases. In particular, intracellular fluid viscosity plays a crucial role in controlling many diffusion-mediated cellular processes, including signaling and transport. In addition, intracellular viscosity has been shown to be a clear cause of atherosclerosis, hypertension, diabetes, alzheimer's disease, and cellular malignancies.
Intracellular pH plays an important role in many biological physiological processes, such as enzymatic activity, apoptosis, phagocytosis, and tumor growth. The intracellular pH of mammalian cells ranges from an acidic pH (4.5-5.5) to a slightly alkaline pH (8.0) in the mitochondria. Abnormalities in the pH of mammalian cells can lead to dysfunction of the cells, leading to the development of a variety of diseases, including cancer and alzheimer's disease.
In recent years, fluorescent probe technology has been widely used for detecting active substances or internal environments in cells/tissues due to its advantages of high sensitivity, simple operation, and little damage to biological samples. However, bifunctional probes capable of detecting viscosity and pH are currently scarce.
Disclosure of Invention
The invention designs and prepares the difunctional fluorescent probe for detecting the viscosity and the pH, provides a novel powerful analysis tool for researching the relation between the viscosity and the pH in cells and even tissues, and has very important significance.
The invention provides a bifunctional fluorescent probe for detecting viscosity and pH, which has a structural formula shown as a formula I:
the invention also provides a preparation method of the bifunctional fluorescent probe, which comprises the following steps:
under the protection of inert gas, adding a compound shown as a formula II, a compound shown as a formula III and sodium methoxide into a solvent for reaction, and separating and purifying reaction liquid to obtain the compound;
the reaction formula is as follows:
optionally, the mass ratio of the compound shown in the formula II, the compound shown in the formula III and sodium methoxide is 1: 1-1.2: 0.2-0.4.
Alternatively, the mass ratio of the compound represented by the formula II, the compound represented by the formula III and sodium methoxide is 1:1.2: 0.2.
alternatively, the separation and purification method may be as follows: and (3) concentrating the reaction solution under reduced pressure to remove the solvent, and purifying the crude product by using a column chromatography with ethyl acetate/petroleum ether (v/v, 1:5) mixed solution as a developing agent to obtain the target fluorescent probe (I).
The compound (III) of the present invention is a disclosed compound, and its preparation method can be referred to in the literature (Wu Y, Yu W T, Hou T C, et al. A selective and reactive fluorine album protocol for the determination of the raw album [ J ]. Chemical Communications,2014,50(78): 11507-11480.).
Compound (II) is commercially available.
Optionally, the solvent is acetonitrile.
Optionally, the reaction conditions are: stirring and reacting for 12-14 h at 30-40 ℃.
The invention also provides an application of the bifunctional fluorescent probe in solution or intracellular viscosity detection.
When the method is applied to the detection of the viscosity of the solution, the viscosity in the solution can be quantitatively detected, and the detection method comprises the following steps:
and adding the difunctional fluorescent probe into the solution to be detected, collecting the fluorescence intensity of the reaction solution under the conditions that the excitation wavelength is 480nm and the emission wavelength is 535nm after the reaction is finished, and calculating according to a standard curve to obtain the viscosity of the solution to be detected.
Optionally, the adding amount of the fluorescent probe in the solution to be detected is calculated by the ratio of the molar weight of the fluorescent probe to the viscosity of the solution: 0.005mM fluorescent probe: the viscosity of the solution is 100-950 CP.
Alternatively, the standard curve is prepared as follows:
and (3) respectively reacting the 0.005mM fluorescent probe with a solution with the viscosity of 100-950 CP, collecting the fluorescence intensity of the reaction solution under the excitation wavelength of 480nm and the emission wavelength of 535nm, and drawing by taking ln (fluorescence intensity) as a vertical coordinate and log (solution viscosity) as a horizontal coordinate to obtain a linear standard curve.
Optionally, the pH of the solution is around 7.4 at the time of detection.
When the method is applied to intracellular viscosity detection, the intracellular viscosity can be qualitatively detected, and the detection method comprises the following steps:
and (3) co-culturing the fluorescent probe and the cell to be detected, then performing fluorescent detection, and qualitatively detecting the viscosity change in the cell through the change of fluorescence brightness.
The invention also provides an application of the bifunctional fluorescent probe in solution or intracellular pH detection.
Optionally, the cell is human cervical cancer cell Hela cell.
The principle of the double-function fluorescence detection is as follows:
and (3) viscosity detection principle: the fluorescent probe shown in the formula (I) can limit the rotation of a carbon-carbon single bond of a structure in a solution with certain viscosity, so that the non-radiative energy of the probe is reduced, and the change of fluorescence from off to on is realized.
The pH detection principle is as follows: the gain and loss of protons from nitrogen atoms in benzimidazole affect the fluorescence intensity of probe (I).
Compared with the prior art, the invention has the beneficial effects that at least:
(1) the invention prepares and provides a bifunctional probe capable of detecting viscosity and pH;
(2) the fluorescent probe can carry out accurate quantitative detection on the viscosity of the solution;
(2) the fluorescent probe can be used for detecting the change of the viscosity and the pH value in the cell, and provides a new technical means for researching the physiological action of the viscosity and the pH value in the cell.
Drawings
FIG. 1 shows a nuclear magnetic hydrogen spectrum of the probe (I) prepared in example 1.
FIG. 2 is a nuclear magnetic carbon spectrum of probe (I) prepared in example 1.
Fig. 3 is a graph showing uv-vis absorption spectra of the probe (I) prepared in example 1 added to PBS buffer and Gly/PBS buffer (v/v ═ 9: 1).
Fig. 4 shows fluorescence emission spectra (pH 7.4) of probe (I) prepared in example 1 in Gly/PBS buffer (v/v ═ 1:9 to 9: 1).
Fig. 5 is a graph of the linear relationship (pH 7.4) of probe (I) prepared in example 1 in Gly/PBS buffer (v/v ═ 1:9 to 9: 1).
Fig. 6 shows fluorescence intensities of the probes (I) prepared in example 1 under DMSO/PBS buffer (pH 7.4, v/v 1/199) for fluorescence interference test of the related bioactive substances.
Fig. 7 is a graph showing uv-vis absorption spectra of the probe (I) prepared in example 1 under DMSO/different pH buffer (v/v-1/99).
Fig. 8 is a fluorescence emission spectrum of the probe (I) prepared in example 1 under DMSO/different pH buffer (v/v-1/99).
Fig. 9 is a curve fitted to the fluorescence intensity at 540nm of probe (I) prepared in example 1 in DMSO/different pH buffer (v/v-1/99).
FIG. 10 is an image of the cell viscosity of the probe (I) prepared in example 1.
FIG. 11 is a photograph showing a photograph of the pH of the cells of the probe (I) prepared in example 1.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1: preparation of Probe (I)
Compound II is available from Annagi.
Compound III is a disclosed compound, and is prepared by the method of the direct reference in this example (Wu Y, Yu W T, Hou T C, et al. A selective and reactive fluorine album protocol for the determination of the real album [ J ]. Chemical Communications,2014,50(78): 11507-11480.).
Adding a compound II, a compound III and sodium methoxide into an acetonitrile solvent under the protection of inert gas (nitrogen), wherein the mass ratio of the compound II to the compound III to the sodium methoxide is 1:1.2:0.2, the compound II is 1mmol, the using amount of acetonitrile is 10mL, stirring and reacting at 35 ℃ for 12h, concentrating the reactant under reduced pressure, and purifying by using silica column chromatography of ethyl acetate/petroleum ether (v/v, 1:5) to obtain a probe (I) (the yield is 60%), wherein the nuclear magnetic hydrogen spectrum is shown in figure 1, and the nuclear magnetic carbon spectrum is shown in figure 2.
1H NMR(500MHz,CDCl3)7.78(d,J＝13.0Hz,2H),7.63–7.43(d,J＝12.0Hz,,2H),7.06(m,2H),6.84(m,1H),3.39–3.31(m,4H),2.96(t,J＝6.4Hz,2H),2.82(t,J＝6.2Hz,2H),2.06–1.99(m,4H).13C NMR(500MHz,CDCl3)168.78,163.08,133.13,130.59,130.17,129.30,128.99,128.87,128.80,126.83,124.36,123.11,112.34,98.31,77.29,77.23,77.03,76.78,49.77,29.07,20.92。
Example 2: probe (I) (5 μ M) was tested for uv-vis absorption spectra in PBS and 90% volume fraction glycerol.
An amount of the probe (I) (prepared in example 1) was accurately weighed, a 1mM concentration of the probe stock solution was prepared with dimethyl sulfoxide, 2. mu.L of the solution was pipetted into 0.398mL of glycerol/PBS buffer (glycerol/PBS, v: v, 1:9) and then into a 96-well plate, and the UV-visible absorption spectrum of the probe (I) was measured.
The fluorescence spectrum is shown in FIG. 3. The experimental result shows that when the viscosity of the buffer solution is increased, the absorption of the probe (I) at 480nm is continuously enhanced, which indicates that the probe (I) has a recognition effect on the viscosity.
Example 3: the fluorescence property of the probe (I) was measured by changing the fluorescence intensity of the probe with the change of viscosity in DMSO/PBS buffer (v/v-1/199) at pH 7.4.
An amount of probe (I) (prepared in example 1) was accurately weighed, prepared into a probe stock solution with a concentration of 1mM using dimethyl sulfoxide, pipetted at 2. mu.L into 0.398mL of PBS buffer solutions with different viscosity values (final viscosity values of 100, 200, 300, 400, 500, 600, 700, 800, 950, respectively), added to a 96-well plate at 37 ℃ and the change in fluorescence intensity of probe (I) was measured and plotted as a correlation linear curve.
The fluorescence spectra are shown in FIGS. 4 and 5. The data show that as the viscosity of the buffer increases, the fluorescence intensity increases nearly 100-fold at an excitation wavelength of 480nm and an emission wavelength of 535 nm. Meanwhile, a linear relation graph is drawn by taking ln (fluorescence intensity) as a vertical coordinate and log (viscosity) as a horizontal coordinate, and the ln (fluorescence intensity) and the log (viscosity) have good linear relation (R)20.98), the probe is proved to have good detection effect.
Example 4: the probe (I) (5. mu.M) in the present invention was tested for fluorescence specificity under the conditions of DMSO/PBS buffer (pH 7.4, v/v 1/199)
An amount of compound (I) (prepared in example 1) was accurately weighed, prepared into a 1mM concentration probe stock solution using dmso, pipetted 2 μ L into 0.394mL, followed by 4 μ L of biologically relevant aqueous interferent solution (1-12, PBS, copper ion, calcium ion, zinc ion, iron ion, glucose, glutathione, homocysteine, cysteine, sodium bisulfate, hydrogen peroxide, t-butyl hydroperoxide, glycerol, final concentration all 1mM), and the fluorescence value was measured at 37 ℃. The fluorescence excitation wavelength is 480nm, and the emission wavelength is 530 nm.
The fluorescence spectrum is shown in FIG. 6. The experimental result shows that except glycerol, the fluorescence intensity of the compound (I) is basically not obviously changed in the presence of other related bioactive molecules, and the detection specificity is good.
Example 5: test of UV-visible absorption Spectroscopy of Probe (I) (5. mu.M) of the present invention in DMSO/PBS buffer (v/v. 1/199) at various pH values
An amount of the compound (I) prepared in example 1 was accurately weighed, prepared into a probe stock solution with a concentration of 1mM using dimethyl sulfoxide, and 2. mu.L of the solution was pipetted into 0.398mL of PBS buffers with different pH values (so that the final pH values in the buffers were from 2 to 10.5, respectively), added to a 96-well plate, and the change in the UV-visible absorption intensity was examined.
The fluorescence spectrum is shown in FIG. 7. The data show that compound (I) has a strong sensitivity to pH. Under acidic conditions, the optimal absorption peak is at 360nm, and the absorption intensity gradually increases along with the gradual increase of pH. Thus, the probe (I) has a pH recognition effect.
Example 6: the probe (I) (5. mu.M) of the present invention was subjected to fluorescence performance test at different pH values in DMSO/PBS buffer (v/v. 1/199)
A certain amount of the probe (I) was accurately weighed, prepared into a probe stock solution with a concentration of 1mM using dimethyl sulfoxide, and 2. mu.L of the probe stock solution was pipetted into 0.398mL of PBS buffers with different pH values (so that the final pH values in the buffers were from 2 to 10.5, respectively), added to a 96-well plate, and the fluorescence intensity was measured. The excitation wavelength was 430 nm.
The fluorescence spectra are shown in FIGS. 8 and 9. The data show that probe (I) has a recognition effect on pH, and as pH is gradually increased, the emission wavelength gradually increases at 540nm and a curve is fitted between pH and the fluorescence intensity of probe (I) at 540nm, and pKa of 8.13 is calculated, indicating that probe (I) has a response ability to pH.
Example 7 use of the Probe (I) of the present invention for viscosity measurement in cells.
A certain amount of the probe (I) was accurately weighed, a 10mM stock solution was prepared from dimethyl sulfoxide, and 2. mu.L of the solution was pipetted into 1.998mL of DMEM medium. Blank group: 1mL of the culture containing the probe (I) was added to Hela cells, incubated at 37 ℃ for 0.5h, washed twice with PBS, and experimental groups: incubating with commercial Nystatin (Nystatin) at 37 deg.C for 20min, washing twice with PBS, adding 1mL of the culture containing probe (I) to Hela cells, washing twice with PBS, and imaging cells with olympus Fluoview FV 1200 confocal microscope. The excitation wavelength of the confocal microscope is 488nm, and the emission and receiving wavelength range is 520-600 nm.
The fluorescence spectrum is shown in FIG. 10. The results of the experiment showed that the mean fluorescence intensity of the untreated cells was 14.069 and that the mean fluorescence intensity was 37.646 after the addition of nystatin to change the intracellular viscosity, indicating that the probe (I) can detect the change in the intracellular viscosity of Hela.
Example 8 use of the Probe (I) of the present invention for pH measurement in cells.
A certain amount of the probe (I) was accurately weighed and prepared into a 10mM stock solution with dimethyl sulfoxide. Cells were incubated at 37 ℃ for 20min using nigericin (0.5. mu. mol) DMEM ( pH 6, 9, respectively). Then 2 μ L of probe stock solution was added for incubation, and after incubation for half an hour, washed twice with 1mL PBS buffer, and finally fluorescence imaging was performed with olympus Fluoview FV 1200 confocal microscope. FIG. 10 is a diagram of the effect of confocal fluorescence imaging of cells: the excitation wavelength is 405nm, and the emission and receiving wavelength range is 530nm and 600 nm.
The fluorescence spectrum is shown in FIG. 11. The experimental results show that the fluorescence intensity of the cells at pH 9 is higher than that at pH 6, indicating that the probe (I) can detect the change of intracellular pH.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (1)
1. The application of the bifunctional fluorescent probe shown as the formula I in the preparation of a solution or an intracellular pH value detection reagent;
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| FR2989377B1 (en) * | 2012-04-12 | 2014-11-21 | Ecole Norm Superieure Lyon | ORGANIC FLUOROPHORES EMITTING IN THE SOLID STATE |
| CN108997255A (en) * | 2018-07-30 | 2018-12-14 | 河南师范大学 | A kind of vinyl ethers Hg2+Fluorescence probe and its preparation method and application |
| CN109761978A (en) * | 2019-01-18 | 2019-05-17 | 商丘师范学院 | A kind of near infrared fluorescent probe detecting benzenethiol and its synthetic method and application |
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| FR2989377B1 (en) * | 2012-04-12 | 2014-11-21 | Ecole Norm Superieure Lyon | ORGANIC FLUOROPHORES EMITTING IN THE SOLID STATE |
| CN108997255A (en) * | 2018-07-30 | 2018-12-14 | 河南师范大学 | A kind of vinyl ethers Hg2+Fluorescence probe and its preparation method and application |
| CN109761978A (en) * | 2019-01-18 | 2019-05-17 | 商丘师范学院 | A kind of near infrared fluorescent probe detecting benzenethiol and its synthetic method and application |
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