CN112266351A - Two-photon ratio fluorescent probe and preparation method and application thereof - Google Patents
Two-photon ratio fluorescent probe and preparation method and application thereof Download PDFInfo
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Abstract
The present disclosure provides a two-photon ratio fluorescent probe, a preparation method and an application thereof, wherein the chemical structure of the fluorescent probe is as follows:
compared with the traditional Golgi positioning group, the benzenesulfonyl amino group is used as the Golgi positioning group in the method, so that the fluorescent probe can be synthesized with low cost and high efficiency, and the effect of positioning the Golgi by the probe is better. The probe has good ratio type fluorescence response to solutions with different polarities, has good light stability, and can be used for detecting polarity changes in different solvent environments. The cytotoxicity is low, and the reagent has good biocompatibility, so that the reagent can be used for detecting the polarity of the golgi in living cells.
Description
Technical Field
The disclosure relates to a two-photon ratio fluorescent probe and a preparation method and application thereof.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
Acute Kidney Injury (AKI) refers to a clinical syndrome caused by rapid decline of renal function in a short time due to various causes, and pathophysiological mechanisms generally include processes of leukocyte infiltration, inflammatory factor production and release, free radical oxidation and the like. AKI is associated with high morbidity and mortality, is a critical condition in kidney disease, and may cause complete loss of kidney function if not discovered and effectively treated in time.
In biological systems, particularly at the cellular level, polarity determines the interactive activity of a large number of proteins and enzymes. In addition, abnormal changes in polarity are closely related to various diseases. The golgi apparatus is an organelle composed of many vesicles and mainly functions in secretion, and is a main site for protein secretion, transportation and assembly, and a large number of protein glycosylation modifications occur in the golgi apparatus. During the occurrence of AKI, synthesis and secretion of a large amount of protein are involved, and it is inevitable that the golgi apparatus, which is a site of protein processing and transport, plays an important role in the occurrence of AKI. The polarity of the golgi may change when AKI occurs. Therefore, it is necessary to develop a detection means for efficiently targeting golgi and quantitatively detecting the polarity change of golgi in situ.
The two-photon fluorescence imaging technology can be used for tomography of deep parts in biological tissues, has the advantages of higher spatial and temporal resolution, lower cell phototoxicity, capability of avoiding tissue autofluorescence and the like, and is widely applied to cell and living body imaging research in recent years. At present, no relevant report of developing a two-photon fluorescent probe for detecting the polarity of the Golgi apparatus is seen.
Disclosure of Invention
Aiming at the technical problems in the prior art, the invention provides a two-photon ratio fluorescent probe and a preparation method and application thereof.
To solve the above technical problem, one or more of the following embodiments of the present invention provide the following technical solutions:
in a first aspect, the present disclosure provides a two-photon ratiometric fluorescent probe TP-Golgi, which has the following chemical structure:
in a second aspect, the present disclosure provides a method for preparing the two-photon ratio type fluorescent probe, comprising the steps of:
3-ethyl-1, 1, 2-trimethyl-1H-benzo [ e ] indole iodide and p-aldehyde benzoic acid are used as raw materials to carry out condensation of methyl and aldehyde groups, and the reaction product and p-aminobenzene sulfonamide carry out amidation reaction of carboxyl and amino.
In a third aspect, the present disclosure provides the use of the above-described two-photon ratio type fluorescent probe for detecting polarity.
In a fourth aspect, the present disclosure provides the use of the above fluorescent probe in targeted detection of polarity or detection of golgi polarity.
In a fifth aspect, the disclosure provides an application of the fluorescent probe in preparing a target golgi polar fluorescent probe.
In a sixth aspect, the present disclosure provides an application of the above fluorescent probe in preparing a two-photon ratio fluorescence imaging polarity detection probe.
Compared with the prior art, one or more technical schemes of the invention have the following beneficial effects:
1. the present disclosure provides a ratiometric fluorescent probe as a highly efficient fluorescent probe targeting the cell golgi. Compared with the traditional Golgi positioning group, the benzenesulfonyl amino group is used as the Golgi positioning group in the method, so that the fluorescent probe can be synthesized with low cost and high efficiency, and the effect of positioning the Golgi by the probe is better.
2. The present disclosure provides a ratiometric fluorescent probe, which has a good ratiometric fluorescent response to solutions of different polarities, and has good photostability, and can be used to detect polarity changes in different solvent environments.
3. The ratiometric fluorescent probes in the present disclosure have low cytotoxicity and good biocompatibility, and thus can be used for polarity detection of golgi in living cells.
4. The ratiometric fluorescent probe disclosed by the disclosure has a two-photon imaging property, and the property enables the ratiometric fluorescent probe to realize the positioning of a golgi in a cell, reduce the phototoxic influence on the cell and living tissues and realize high-spatial-temporal resolution imaging of deep tissues in the living body. In addition, the probe is successfully applied to the detection of polarity in kidney tissues in an acute kidney injury mouse model.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a spectrum of a probe TP-Golgi prepared in example 1 of the present disclosure in a solution of different polarities, where a is an ultraviolet absorption spectrum and b is a fluorescence spectrum;
FIG. 2 is a graph showing the photostability characterization of the probe TP-Golgi prepared in example 1 of the present disclosure in different polar environments; 1-28 are GSH, Cys, Asn, Gln, Thr, Ser, t-BuOOH, CIlO-,O2 .-,1O2,H2O2,ROO.,ONOO-,Zn2+,Fe2 +,Cu2+,Mg2+,Ca2+,K+,Fe3+,Al3+,Cd2+,Li+,Mn2+,Cu+,Na+Ethyl acetate;
FIG. 3 is a diagram showing confocal images of fluorescence of cells after the probe TP-Golgi prepared in example 1 of the present disclosure is co-stained with different subcellular organelle localization dyes in human normal hepatocytes HL-7702, wherein a is Golgi dyes (the scales in the left, middle and right panels are consistent), b is mitochondrial dyes (the scales in the left, middle and right panels are consistent), c is lysosomal dyes (the scales in the left, middle and right panels are consistent), d is a graph showing the trend of fluorescence intensity of the probe TP-Golgi and Golgi dyes, e is a graph showing the trend of fluorescence intensity of the probe TP-Golgi and mitochondrial dyes, and f is a graph showing the trend of fluorescence intensity of the probe TP-Golgi and lysosomal dyes;
FIG. 4 is a confocal fluorescence imaging characterization diagram of the probe TP-Golgi prepared in example 1 of the present disclosure in the human normal hepatocyte HL-7702 and the human cervical cancer cell HeLa, FIGS. a-d are imaging characterization diagrams of the green channel, the red channel, the bright field and the ratio channel of the human normal hepatocyte HL-7702, FIGS. e-h are imaging characterization diagrams of the green channel, the red channel, the bright field and the ratio channel of the human cervical cancer cell HeLa, respectively, and i is a data output diagram of two cell ratio channels;
fig. 5 is a data output diagram of polar change and fluorescence intensity ratio of Golgi probe TP-Golgi in detecting kidney of normal mouse and acute kidney injury model mouse, fig. a-c are two-photon fluorescence imaging 3D characterization diagrams of kidney of normal mouse, fig. D-f are two-photon fluorescence imaging 3D characterization diagrams of kidney of acute kidney injury model mouse, fig. g is a data output diagram of fluorescence intensity ratio of two-photon imaging of kidney of two groups of mouse, and fig. h is a data diagram of serum creatinine level of normal mouse and acute kidney injury model mouse.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
In a first aspect, the present disclosure provides a two-photon ratiometric fluorescent probe TP-Golgi, which has the following chemical structure:
in a second aspect, the present disclosure provides a method for preparing the two-photon ratio type fluorescent probe, comprising the steps of:
3-ethyl-1, 1, 2-trimethyl-1H-benzo [ e ] indole iodide and p-aldehyde benzoic acid are used as raw materials to carry out condensation reaction of methyl and aldehyde group, and the reaction product and p-aminobenzene sulfonamide are subjected to amidation reaction of carboxyl and amino.
Starting material 3-ethyl-1, 1, 2-trimethyl-1H-benzo [ e ]]The chemical structural formula of the indole iodide is shown in the specification
The chemical structure of the raw material p-aldehyde benzoic acid is
The chemical structure of the raw material sulfanilamide is
The synthetic route is as follows:
in some embodiments, the condensation reaction of methyl groups with aldehyde groups is carried out at a temperature of from 70 to 90 ℃ for a time of from 3 to 12 hours.
Further, the condensation reaction of methyl and aldehyde group is carried out at the reaction temperature of 80 ℃ for 6 h.
In some embodiments, the environment of the condensation reaction of methyl groups with aldehyde groups is a basic environment.
Further, the pH value of the alkaline environment is 8-9.
Further, the basic environment is provided by piperidine.
Furthermore, the solvent of the reaction system of the condensation reaction is absolute ethyl alcohol.
In some embodiments, the conditions for the amidation reaction of a carboxyl group with an amino group are: heating to 60-80 deg.C in thionyl chloride, reacting for 1.5-5h, and reacting at room temperature for 10-14h under alkaline condition.
Further, the amidation reaction conditions of the carboxyl group and the amino group are as follows: firstly heating to 70 ℃ in thionyl chloride, reacting for 2h, and then reacting for 12h at room temperature under an alkaline condition.
Further, the solvent for the amidation reaction is acetonitrile.
In some embodiments, the molar ratio of 3-ethyl-1, 1, 2-trimethyl-1H-benzo [ e ] indole iodide, p-aldehyde benzoic acid, and aminobenzenesulfonamide is 1:1.5: 3-4.
In some embodiments, the amidation reaction is followed by column chromatography after removal of the solvent under reduced pressure.
Further, the developing solvent for column chromatography is a mixture of dichloromethane and methanol, and the volume ratio of the dichloromethane to the methanol is 10:1 and 20: 1.
In a third aspect, the present disclosure provides the use of the above-described two-photon ratio type fluorescent probe for detecting polarity.
In a polar environment, the energy difference delta E required for the probe TP-Golgi to generate pi → pi x transition is small, and the probability of the transition is increased, so that the fluorescence wavelength is red-shifted along with the increase of the polarity of the solvent, and the fluorescence intensity at the long wavelength is also enhanced. As the polarity of the solvent increases, the fluorescence emission wavelength of the probe is red-shifted from 440nm to 600nm, and the fluorescence intensity at 600nm is increased by about 19 times.
In a fourth aspect, the present disclosure provides the use of the above fluorescent probe in targeted detection of polarity or detection of golgi polarity.
In a fifth aspect, the disclosure provides an application of the fluorescent probe in preparing a target golgi polar fluorescent probe.
In a sixth aspect, the present disclosure provides an application of the above fluorescent probe in preparing a two-photon ratio fluorescence imaging polarity detection probe.
Example 1:
the synthesis process of the fluorescent probe comprises the following steps:
3-Ethyl-1, 1, 2-trimethyl-1H-benzo [ e ] indole iodide (0.50g,2mmol) and p-aldehyde benzoic acid (0.36g,2.4mmol) were weighed out and dissolved in 10mL of anhydrous ethanol, 10. mu.L of piperidine was added to provide an alkaline environment, the mixture was heated to 80 ℃ and reacted under reflux for 6 hours, and then 10. mu.L of acetic acid was added thereto and reacted for 10 minutes. After the reaction was stopped, the anhydrous ethanol was distilled off under reduced pressure, followed by reaction with dichloromethane: methanol 10:1 as a developing solvent was separated and purified by silica gel column chromatography to obtain compound 1(0.56g, 76%) as an orange solid intermediate.
Intermediate compound 1(0.13g,0.35mmol) was weighed out and dissolved in excess thionyl chloride (5.2mL,72mmol), and then 1-2 drops of DMF were added to assist dissolution and refluxed at 70 ℃ for 2 h. After completion of the reaction, excess solvent was removed, and the mixture was dissolved in 5mL of acetonitrile, and p-aminobenzenesulfonamide (0.24g,1.4mmol) and triethylamine (300. mu.L, 2.2mmol) were added to the solution to conduct a reaction at room temperature for 12 hours. After the reaction was stopped, acetonitrile and triethylamine were removed, followed by reaction with dichloromethane: methanol 20:1 as a developing solvent was separated and purified by silica gel column chromatography to obtain TP-Golgi as an orange solid (55mg, 30%).
Nuclear magnetic and mass spectrum characterization:
1H NMR(400MHz,DMSO)δ10.95(s,1H),8.63(d,J＝16.52Hz,1H),8.47(d,J＝2.7Hz,2H),8.45(d,J＝2.7Hz,2H),8.34(d,J＝8.9Hz,1H),8.25(d,J＝7.6Hz,2H),8.19(d,J＝8.9Hz,1H),8.07(d,J＝7.6Hz,2H),7.84(d,J＝5.3Hz,2H),7.80–7.78(t,J＝7.0Hz,1H),7.63(d,J＝8.2Hz,1H),7.34(d,J＝5.4Hz,2H),7.32–7.28(t,J＝7.0,1H),4.95(m,2H),2.07(s,6H),1.57(t,J＝14.7Hz,3H).13C NMR(101MHz,DMSO)δ182.58,165.47,151.47,142.48,139.72,139.46,138.56,137.93,137.88,133.88,131.71,130.79,130.55,129.10,129.02,128.00,127.18,126.95,123.76,120.63,114.38,113.86,54.63,49.04,43.43,29.48,29.14,25.71,22.54,14.63,14.41.HRMS(ESI)m/z:[M+]calculated for C31H30N3O3S+,524.2008found 524.2046.
effect experiment:
generally, the dye molecules can be dissolved in physiological saline, buffer solution or water-soluble organic solvent such as acetonitrile, dimethylsulfoxide, etc., and then added with appropriate buffer solution and other organic reagents for the test.
The photophysical properties of the probe TP-Golgi in water/dioxane mixed solution with different polarities (the polarity of the solution is adjusted by adjusting the volume fraction of water, the polarity is larger when the volume fraction of water is larger; in the examples, the mixed solution with the volume fraction of water being 10%, 20%, 40%, 60% and 80%) and a plurality of common organic reagents with different polarities (such as ethyl acetate, ethanol, methanol, water and the like) are respectively researched, and the probe TP-Golgi is used for two-photon fluorescence imaging experiments of living cells and acute kidney injury mice. The living cell staining method is to incubate the cultured cells in a culture solution containing probe molecules, remove the incubation solution after incubation for a certain time, and perform a two-photon and single-photon confocal imaging experiment. The mouse staining method is to inject the probe into the mouse body through tail vein, and after a period of time, the kidney of the mouse is subjected to in-situ two-photon fluorescence imaging.
Ultraviolet absorption, fluorescence emission and selectivity experiments of a probe TP-Golgi in solutions with different polarities:
the ultraviolet absorption and fluorescence response properties of the probe TP-Golgi in solutions of different polarities were studied. After the probe TP-Golgi (50 μ M) is added into the solutions with different polarities, the ultraviolet absorption spectrum of the probe is detected, and the fluorescence emission spectrum of the probe TP-Golgi (10 μ M) in the solutions with different polarities is detected by taking the maximum absorption wavelength as the excitation wavelength.
As shown in fig. 1a, the absorption spectrum of probe TP-Golgi (50 μ M) changes only slightly as the polarity of the solution increases (Δ f ═ 0.184-0.311). FIG. 1b shows fluorescence spectra of probe TP-Golgi (10. mu.M) in solutions of different polarity (. DELTA.f ═ 0.184-0.311). Under the excitation of 380nm light, the fluorescence intensity of the probe at 440nm gradually decreases and the fluorescence intensity at 600nm gradually increases with the increasing polarity. The above results show that the probe TP-Golgi has a fluorescence response with higher sensitivity to polarity, and the polarity can be quantitatively detected through ratiometric fluorescence.
FIG. 2 shows the fluorescent response of the probe TP-Golgi to various intracellular active substances. The active substances detected in the cells include various amino acids (GSH, Cys, Asn, Gln, Thr, Ser), active oxygen (t-BuOOH, CIlO)-,O2 .-，1O2，H2O2,ROO.，ONOO-) Metal ion (Zn)2+,Fe2+,Cu2+,Mg2+,Ca2+,K+,Fe3+,Al3+,Cd2+,Li+,Mn2+,Cu+,Na+) And the like. As shown in FIG. 2, the numbers 1-28 are GSH, Cys, Asn, Gln, Thr, Ser, t-BuOOH, CIlO-,O2 .-,1O2,H2O2,ROO.,ONOO-,Zn2+,Fe2+,Cu2+,Mg2+,Ca2+,K+,Fe3+,Al3+,Cd2+,Li+,Mn2+,Cu+,Na+And ethyl acetate.
Fluorescence intensity ratio FI of probe TP-Golgi in the presence of various intracellular active substances600nm/FI440nmSubstantially in accordance with the ratio FI of the fluorescence intensities in water only and in less polar ethyl acetate600nm/FI440nmIs obviously reduced. This result demonstrates that TP-Golgi has a better selective response to polarity than various biologically active substances and can be used to specifically detect changes in polarity in complex cells and in vivo.
Golgi targeting experiments of the probe TP-Golgi:
human normal liver cell HL-7702 was cultured in high-glucose DMEM medium. After the cells were incubated for 30min with 10. mu.M probes and 0.5. mu.M commercial dyes (including Golgi, mitochondria, lysosomes) to localize different subcellular organelles, the co-localization imaging experiment was performed using confocal laser microscopy. As shown in FIG. 3, the better the overlap of fluorescence sites, the more consistent the trend curve, indicating the better the co-localization effect of the probe. As shown in FIG. 3, the probe TP-Golgi exhibits excellent Golgi targeting ability.
A probe TP-Golgi performs single-photon and double-photon confocal fluorescence imaging experiment on living cells:
culturing human normal liver cell HL-7702 and human cervical cancer cell HeLa by high-sugar DMEM culture solution, respectively adding DMEM solution containing 10 μ M probe, incubating at 37 deg.C for 30min, washing the incubation solution, and performing single-photon and two-photon laser confocal fluorescence imaging. As can be seen from FIG. 4, the probe TP-Golgi can image under both single photon and two photon conditions. Wherein, fig. 4A is a single photon laser confocal fluorescence imaging graph and a fluorescence intensity ratio data output graph of the human normal hepatocyte HL-7702 and the human cervical carcinoma cell HeLa, and fig. 4B is a two-photon laser confocal fluorescence imaging graph and a fluorescence intensity ratio data output graph of the human normal hepatocyte HL-7702 and the human cervical carcinoma cell HeLa. The single photon excitation light is 405nm, the two-photon excitation light is 760nm, and fluorescence is collected at 430-500 nm and 550-650 nm. Probe for two-photon confocal fluorescence imaging experiments in the kidney of polar kidney injury model mice:
mice were injected with LPS intraperitoneally to induce acute kidney injury, and control mice were injected with the same amount of saline intraperitoneally. After 24 hours, the probe TP-Golgi (50. mu.M, 100. mu.L) was injected into the mice via the tail vein, and 30 minutes later, the mice were anesthetized with chloral hydrate and two-photon fluorescence imaging experiments were performed on mouse kidney tissue under excitation light of 760 nm. As shown in FIG. 5, a-b and d-e are two-photon fluorescence imaging graphs of kidney of mice in the control group and the polar kidney injury group, respectively, a c-f are two-photon fluorescence imaging ratio channel graphs of kidney of the two groups of mice, respectively, a g-g is a ratio channel data output graph, and a h-h is a serum creatinine content data graph of the two groups of mice. As can be seen from FIG. 5, under the excitation light of 760nm, the ratio FI of the fluorescence intensity at the kidney site of LPS-induced acute kidney injury model mouseRed/FIGreenHigher than the control group mice, the kidney polarity of the LPS-induced acute kidney injury model mice is higher than that of the control group mice. The serum creatinine content is one of the key indicators for the evaluation of acute kidney injury, and therefore, in order to determine that LPS-treated mice have acute kidney injury, commercial creatinine kit was used to detect creatinine in the mouse serumThe content of (a). As shown in the graph h, the detection result of the kit shows that the serum creatinine content of the mice in the LPS treatment group is obviously higher than that of the mice in the control group, which is consistent with the two-photon fluorescence imaging result. This indicates that TP-Golgi can be used as a ratio-type two-photon fluorescent probe for detecting polarity in a living body.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
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