CN110818703B - Pyrrole-part cyanine derivative fluorescent probe and preparation method and application thereof - Google Patents
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Abstract
The invention providesA pyrrole-part cyanine derivative fluorescent probe and a preparation method and application thereof, wherein the chemical structural formula of the pyrrole-part cyanine derivative is as follows:
(ii) a The preparation method comprises the following steps: dissolving N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-formamide and N-ethylbenzothiazole iodide in an organic solvent; dripping piperidine into the obtained solution to be used as a catalyst, and then refluxing and stirring the solution at the temperature of 80 ℃ to react for 3 to 4 hours; and then cooling to room temperature, carrying out vacuum filtration, washing the obtained solid residue with ethanol, and recrystallizing with ethanol to obtain the pyrrole-part cyanine derivative fluorescent probe. The pyrrole-part cyanine derivative fluorescent probe can selectively react with hypochlorite under the condition of pure water phase physiology, the solution is yellow and faded, and meanwhile, green fluorescence is obviously weakened, and the pyrrole-part cyanine derivative fluorescent probe is particularly used as a fluorescent probe for conveniently detecting the hypochlorite in a cell lysosome.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a pyrrole-part cyanine derivative, and a preparation method and application thereof.
Background
Hypochlorous acid (HClO) is generally present in physiological environments in the form of hypochlorite (ClO-), has a bactericidal effect, and also has an immunological effect when microorganisms invade the body. However, excessive amounts of HClO produced in phagocytes can also be harmful to humans. There is evidence to suggest that hypochlorite is involved in inflammation in some tissues, and it is believed that hypochlorite released by neutrophils is involved in lung injury, rheumatoid arthritis, hepatic ischemia-reperfusion injury, and kidney disease. Intracellular excess hypochlorite is metabolized primarily by lysosomes, the concentration of which is closely related to the lysosomal redox balance. Hypochlorous acid is also a commonly used disinfectant in daily life. Therefore, the development of selective and sensitive tools for hypochlorite detection in biological samples is becoming increasingly important.
In recent years, fluorescent molecular probe technology has become an important means for detecting important metal ions, anions and small molecules due to its characteristics of high sensitivity, simple operation, low cost and the like. However, most of the existing hypochlorite fluorescent probes need an organic cosolvent (> 10%), and hypochlorite identification cannot be realized in a pure water phase, so that further practical application of the hypochlorite fluorescent probes is limited. And few reports are made on hypochlorite fluorescent probes for lysosome targeting.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
Aiming at the problems in the prior art, the invention synthesizes the hypochlorite fluorescent probe with high sensitivity and high selectivity by taking the excellent photochemical and photophysical characteristics of the merocyanine derivative as the fluorescent probe and introducing a morpholine ring as a positioning group of a lysosome. The probe can be applied to determination of hypochlorite in a pure water system, has a lysosome targeting function, and can be applied to detection of hypochlorite concentration in a lysosome.
The invention mainly aims to provide a pyrrole-part cyanine derivative fluorescent probe which can be used in a pure water system and a cell lysosome and has high sensitivity and good selectivity for hypochlorite; another purpose is to provide a preparation method and application of the fluorescent probe.
In order to achieve the purpose, the invention adopts the following technical scheme: a pyrrole-portion cyanine derivative fluorescent probe, wherein the pyrrole-portion cyanine derivative has the following structural formula:
the invention also provides a preparation method of the pyrrole-part cyanine derivative fluorescent probe, which comprises the following specific steps:
s1: dissolving N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-formamide and N-ethylbenzothiazole iodide in an organic solvent;
s2: dripping piperidine into the solution obtained in the step S1 as a catalyst, and refluxing for 3-4h at 80 ℃;
s3: and cooling the solution obtained in the step S2 to room temperature, carrying out suction filtration under reduced pressure, washing the obtained solid residue with ethanol, and recrystallizing with ethanol to obtain the pyrrole-part cyanine derivative fluorescent probe.
Further, the ethanol is absolute ethanol.
Further, the reflux stirring reaction time in step S2 was 3 hours.
Further, in step S2, the molar ratio of N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-carboxamide to piperidine was 1: 0.02.
Further, the molar ratio of N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-carboxamide and N-ethylbenzothiazole iodide salt added in step S1 is 1: 1.
Further, the specific preparation method comprises the steps of dissolving 2.79 g of N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-formamide (10 mmol) and 3.05 g N-ethylbenzothiazole iodide (10 mmol) in 0.05L of ethanol, dropwise adding 0.017 g of piperidine (0.2 mmol) serving as a catalyst, refluxing and stirring at 80 ℃ for 3-4h, cooling, standing to room temperature, carrying out vacuum filtration, and cleaning the obtained solid with ethanol to obtain the pyrrole-cyanine derivative fluorescent probe.
The invention also provides an application of the pyrrole-part cyanine derivative fluorescent probe, namely an application of the pyrrole-part cyanine derivative fluorescent probe as a hypochlorite fluorescent probe, in particular an application of the pyrrole-part cyanine derivative fluorescent probe as a fluorescent probe for detecting hypochlorite in HeLa living cell lysosomes.
Compared with the prior art, the invention has the advantages and positive effects that:
the pyrrole-part cyanine derivative fluorescent probe is prepared through condensation reaction, raw materials are easy to obtain, and synthesis and post-treatment methods are simple. Among various common anion and active oxygen species, hypochlorite shows higher fluorescence recognition performance. The probe does not need any organic solvent for assisting dissolution in the working environment, is very favorable for being applied to a biological system, and has wide potential application value.
Drawings
FIG. 1 shows the pyrrole-moiety cyanine derivative fluorescent probe prepared in example 1 of the present invention1H NMR spectrum;
FIG. 2 shows the pyrrole-moiety cyanine derivative fluorescent probe prepared in example 1 of the present invention13C NMR spectrum;
FIG. 3 is a mass spectrum of the pyrrole-merocyanine derivative fluorescent probe prepared in example 1 of the present invention;
FIG. 4 shows a pyrrole-moiety cyanine derivative fluorescent probe (1X 10) prepared in example 1 of the present invention-5mol/L) of citric acid-sodium citrate buffer solution (0.02 mol/L, pH = 4) was added to 1 × 10, respectively-4mol/L anion (AcO)−、Br−、Cl−、ClO−、ClO4 −、CN−、F−、H2PO4 −、HPO4 −、I−、PO4 3−、S2−And SO3 2−) Or active oxygen species (H)2O2、1O2OH, NO and O2 −) Ultraviolet (a) and fluorescence (b) spectrograms (excitation wavelength 465 nm);
FIG. 5 shows a pyrrole-moiety cyanine derivative fluorescent probe (1X 10) prepared in example 1 of the present invention-5mol/L) of citric acid-sodium citrate buffer solution (0.02 mol/L, pH = 4) titrated to different concentrations of ClO−The insets respectively show the linear change trend graphs of the absorbance at 465 nm and the fluorescence intensity at 520 nm along with the hypochlorite concentration (the excitation wavelength is 465 nm);
FIG. 6 shows pyrrole-moiety cyanine derivative fluorescent probe and ClO in HeLa cells−A fluorescence imaging map of; 1X 10 for HeLa cells-5Incubation with mol/L fluorescent probe for 30 min and addition of 1X 10-4 mol/L ClO−After further incubation for 30 min, laser confocal microscopy was performed using Olympus FV500-IX70The mirror performs fluorescence imaging.
Wherein: a is a fluorescence imaging diagram of the green channel of the fluorescence probe; b is the bright field diagram of the fluorescent probe; c is a picture obtained by superposing the bright field diagram and the fluorescence diagram of the fluorescent probe; d is the fluorescent probe + ClO−Green channel fluorescence imaging; e is the fluorescent probe + ClO−Imaging under bright field; f is the above fluorescent probe ClO−And (5) superposing the bright field image and the fluorescence image.
FIG. 7 is a photograph of co-staining fluorescence imaging of pyrrole-moiety cyanine derivative fluorescent probes with the commercial lysosomal localization dye LysoTracker Red in HeLa cells; 1X 10 for HeLa cells-5After co-incubation of the mol/L fluorescent probe with the LysoTracker Red for 30 minutes, fluorescence imaging was performed using an Olympus FV500-IX70 laser confocal microscope.
Wherein: a is a green channel fluorescence imaging graph; b is a red channel fluorescence imaging graph; c is a picture obtained by superposing the green channel and the red channel; d is a bright field diagram; e is a picture obtained by superposing a green channel, a red channel and a bright field; and f is an overlay of the green and red channel intensity distributions.
Detailed Description
The present invention is described in further detail below with reference to the drawings and specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The reagents and raw materials adopted by the embodiment of the invention are purchased from conventional markets.
Example 1
The preparation method of the pyrrole-portion cyanine derivative fluorescent probe of the embodiment is as follows:
dissolving 2.79 g of N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-formamide (10 mmol) and 3.05 g N-ethylbenzothiazole iodide (10 mmol) in 0.05L of ethanol, dropwise adding 0.017 g of piperidine (0.2 mmol) as a catalyst, refluxing and stirring at 80 ℃ for 3-4h, cooling and standing to room temperature, carrying out vacuum filtration, cleaning the obtained solid with ethanol, and recrystallizing with ethanol to obtain the pyrrole-part cyanine derivative fluorescent probe. The yield of the desired product was 82%.
The obtained pyrrole-portion cyanine derivatives were subjected to nmr analysis, and the results were as follows:
1H NMR (400 MHz, D2O), (ppm): 7.85-7.87 (1H, d, Ar-H), 7.75-7.77 (1H, d, Ar-H), 7.60-7.63 (d, 1H, CH=), 7.57-7.61 (1H, t, Ar-H), 7.45-7.49 (1H, t, Ar-H), 6.92-6.96 (1H, d, CH=), 4.47-4.52 (2H, q, CH2-CH3), 3.70-3.72 (4H, t, 2CH2), 3.43-3.47 (2H, t, CH2), 2.62-2.64 (6H, m, 3CH2), 2.28 (3H, s, CH3), 2.17 (3H, s, CH3), 1.40-1.43 (3H, t, CH3) The specific nmr hydrogen spectrum is shown in fig. 1;
13C NMR (400 MHz, DMSO-d 6 ) 170.35, 164.33, 142.46, 141.13, 135.51, 133.22, 129.44, 127.73, 127.36, 126.71, 124.41, 122.31, 115.84, 102.77, 66.75, 57.69, 53.63, 43.87, 36.26, 14.03, 13.59, 10.97. the specific NMR carbon spectrum is shown in FIG. 2; the specific mass spectrum is shown in FIG. 3.
Example 2
Determination of optical Properties of pyrrole-moiety cyanine derivatives on hypochlorite
The pyrrole-portion cyanine derivative prepared in example 1 was used as a fluorescent probe and was prepared in a citric acid-sodium citrate buffer solution (0.02 mol/L, pH = 4) at a molar concentration of 1 × 10-5mol/L solutions containing 1X 10 mol/L of the compound-4mol/L of an anion (AcO)−、Br−、Cl−、ClO−、ClO4 −、CN−、F−、H2PO4 −、HPO4 −、I−、PO4 3−、S2−And SO3 2−) Or active oxygen species (H)2O2、1O2OH, NO and O2 −) The same amount of the above fluorescent probe solution is added into the solution, and an ultraviolet-visible spectrophotometer or a fluorescence spectrometer is adopted for analysis (excitation wavelength is 465 nm), and the obtained ultraviolet and fluorescence spectrograms are shown in figure 4.As can be seen from FIG. 4, the pyrrole-part cyanine derivative prepared by the invention has a significant response to hypochlorite as a probe, and both an ultraviolet signal and a fluorescent signal can be used for rapidly identifying hypochlorite, while other ions are unchanged.
ClO can be obtained by calculation from the titration spectrum of FIG. 5−Detection limit of 1.65X 10-7mol/L, the linear detection ranges of the ultraviolet spectrum and the fluorescence spectrum are respectively 2.25 multiplied by 10-5-5.0×10-5mol/L and 10.0X 10-5-3.2×10-5mol/L, therefore, the pyrrole-part cyanine derivative prepared by the invention can be used for ultraviolet and fluorescence quantitative detection of hypochlorite.
Example 3
Detection experiment of intracellular hypochlorite by using pyrrole-part cyanine derivative fluorescent probe
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of protection is not limited thereto. The equivalents and modifications of the present invention which may occur to those skilled in the art are within the scope of the present invention as defined by the appended claims.
Claims (8)
1. A pyrrole-portion cyanine derivative fluorescent probe, which is characterized in that the pyrrole-portion cyanine derivative fluorescent probe has the following structural formula:
2. the method for preparing a pyrrole-moiety cyanine derivative fluorescent probe according to claim 1, characterized by comprising the steps of:
s1: dissolving N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-formamide and N-ethylbenzothiazole iodide in an organic solvent;
s2: dropwise adding piperidine into the solution obtained in the step S1 as a catalyst, and then refluxing and stirring at 80 ℃ for reaction for 3-4 h;
s3: and cooling the solution obtained in the step S2 to room temperature, carrying out suction filtration under reduced pressure, washing the obtained solid residue with ethanol, and recrystallizing with ethanol to obtain the pyrrole-part cyanine derivative fluorescent probe.
3. The method for preparing a pyrrole-moiety cyanine derivative fluorescent probe according to claim 2, characterized in that: the organic solvent in step S1 is absolute ethanol.
4. The method for preparing a pyrrole-moiety cyanine derivative fluorescent probe according to claim 2, characterized in that: the molar ratio of the N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-carboxamide to the N-ethylbenzothiazole iodide added in step S1 is 1: 1.
5. The method for preparing a pyrrole-moiety cyanine derivative fluorescent probe according to claim 2, characterized in that: the reflux stirring reaction time in the step S2 is 3 h.
6. The method for preparing a pyrrole-moiety cyanine derivative fluorescent probe according to claim 2, characterized in that: in the step S2, the molar ratio of N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-carboxamide to piperidine is 1: 0.02.
7. The method for preparing a pyrrole-moiety cyanine derivative fluorescent probe according to claim 2, characterized by comprising the steps of: dissolving 2.79 g N-morpholinoethyl-2, 4-dimethyl-5-formylpyrrole-3-formamide and 3.05 g of N-ethylbenzothiazole iodide in 0.05L of ethanol, dropwise adding 0.017 g of piperidine serving as a catalyst, refluxing and stirring at 80 ℃ for 3-4h, cooling and standing to room temperature, carrying out vacuum filtration, cleaning the obtained solid with ethanol, and recrystallizing with ethanol to obtain the pyrrole-part cyanine derivative fluorescent probe.
8. Use of the pyrrole-moiety cyanine derivative fluorescent probe according to claim 1 as a hypochlorite fluorescent probe in cell lysosome fluorescence imaging.
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