CN117756762B - Preparation of coumarin derivatives and method for ratiometric detection of cysteine - Google Patents
Preparation of coumarin derivatives and method for ratiometric detection of cysteineInfo
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- CN117756762B CN117756762B CN202311756558.8A CN202311756558A CN117756762B CN 117756762 B CN117756762 B CN 117756762B CN 202311756558 A CN202311756558 A CN 202311756558A CN 117756762 B CN117756762 B CN 117756762B
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Abstract
本发明提供了一种香豆素衍生物的制备以及比率检测半胱氨酸的方法，属于香豆素衍生物技术领域。本发明提供的香豆素衍生物能实现靶向溶酶体，实现对溶酶体中Cys的检测，且其作为比率型探针，通过观察比率探针的两种无干扰荧光的比值，可以将浓度、仪器波动、背景荧光等干扰最小化，具有灵敏度高、选择性好、响应时间长等优点。
The present invention provides a method for preparing a coumarin derivative and detecting cysteine by ratiometry, belonging to the technical field of coumarin derivatives. The coumarin derivative provided by the present invention can target lysosomes and detect Cys in lysosomes. As a ratiometric probe, the ratio of two non-interfering fluorescence signals of the ratiometric probe can be observed to minimize interference from concentration, instrument fluctuations, and background fluorescence. The method exhibits advantages such as high sensitivity, good selectivity, and a long response time.
Description
Technical Field
The invention relates to the technical field of coumarin derivatives, in particular to a coumarin derivative, a preparation method and application thereof, and a method for detecting cysteine in a ratio.
Background
More and more studies indicate that lysosomes, as intracellular sensors, can receive signals from other organelles or metabolic pathways within the cell, and make adjustments and signal the cytoplasm and nucleus to regulate specific metabolic processes within the cell, maintaining acidic pH plays a critical role in both basic functions of degradation and circulation of the lysosomes. Cystinosis is the first described genetic disease caused by dysfunctions in lysosomal transport. Lysosomal cystine is a major source of intracellular cysteines, while entry of cysteines into lysosomes requires a pH gradient. Therefore, a fluorescent probe capable of accurately detecting the change of the content of the cysteine in the lysosome of the cell is designed, and the fluorescent probe has important research significance and application value for understanding the process of entering the cysteine into the lysosome and abnormal transportation function of the lysosome.
Disclosure of Invention
In view of the above, the present invention aims to provide a coumarin derivative, a preparation method and application thereof, and a method for detecting cysteine in a ratio. The coumarin derivative provided by the invention can target lysosomes and realize detection of Cys in lysosomes.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a coumarin derivative, which has a structure shown in a formula I:
the invention also provides a preparation method of the coumarin derivative, which comprises the following steps:
mixing 7- (diethylamino) coumarin with an organic solvent to obtain a 7- (diethylamino) coumarin solution;
mixing POCl 3 with an organic solvent to obtain a formylation reagent;
Dropwise adding the 7- (diethylamino) coumarin solution into the formylation reagent to perform formylation reaction to obtain 7- (diethylamino) coumarin-3-formaldehyde;
And mixing the 7- (diethylamino) coumarin-3-formaldehyde, 3-morpholine-3-oxo-propionitrile, piperidine and an organic solvent for Knoevenagel condensation reaction to obtain the coumarin derivative.
Preferably, the molar ratio of the 7- (diethylamino) coumarin to the POCl 3 is 1:2-1:3.
Preferably, the formylation reaction is carried out at a temperature of 55-65 ℃ for 8-16 hours.
Preferably, the molar ratio of the 7- (diethylamino) coumarin-3-formaldehyde to the 3-morpholine-3-oxopropionitrile is 1:1-1:2.
Preferably, the temperature of the Knoevenagel condensation reaction is 70-90 ℃ and the time is 4-6 hours.
The invention also provides the coumarin derivative disclosed by the technical scheme or the application of the coumarin derivative prepared by the preparation method disclosed by the technical scheme in qualitative detection of cysteine.
The invention also provides the coumarin derivative disclosed by the technical scheme or the application of the coumarin derivative prepared by the preparation method disclosed by the technical scheme in the ratio detection of cysteine.
The invention provides a method for detecting cysteine by ratio, which comprises the following steps:
Mixing a solution to be detected, a PBS buffer solution and a coumarin derivative solution, respectively carrying out fluorescence detection at 490nm and 572nm, and calculating the ratio of fluorescence intensity at 490nm and 572nm, wherein the coumarin derivative in the coumarin derivative solution is the coumarin derivative according to the technical scheme or the coumarin derivative prepared by the preparation method according to the technical scheme, and the solution to be detected contains cysteine;
And calculating the concentration of the cysteine in the solution to be detected by using a standard curve, wherein the standard curve takes the concentration of the cysteine as an abscissa and takes F 490/F572 as an ordinate.
Preferably, the pH value of the PBS buffer solution is 4.0-8.0.
Compared with the prior art, the coumarin derivative provided by the invention has the following advantages and effects:
the coumarin derivative provided by the invention can realize targeting lysosomes and detection of Cys in lysosomes, and can be used as a ratio probe, and the interference of concentration, instrument fluctuation, background fluorescence and the like can be minimized by observing the ratio of two non-interference fluorescence of the ratio probe, so that the coumarin derivative has the advantages of high sensitivity, good selectivity, long response time and the like.
The invention also provides a preparation method of the coumarin derivative, and the preparation method has the advantages of simple synthesis steps, low cost and low toxicity.
The invention also provides a method for detecting the cysteine by the ratio, which is simple and quick, can be realized by means of a fluorescence spectrometer, and has the advantages of obvious detection signal and strong specificity by adopting double-channel detection.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the coumarin derivative ECMA prepared in example 1;
FIG. 2 is a nuclear magnetic resonance spectrum of the coumarin derivative ECMA prepared in example 1;
FIG. 3 is a mass spectrum of the coumarin derivative ECMA prepared in example 1;
FIG. 4 is a graph showing fluorescence emission at 572nm for the coumarin derivatives ECMA and Cys;
FIG. 5 is a graph showing fluorescence emission at 490nm for the coumarin derivative ECMA with Cys;
FIG. 6 is a graph showing the linear relationship between the ECMA fluorescence intensity ratio (F 490/F572) of coumarin derivatives and Cys concentration;
FIG. 7 is a bar graph of fluorescence intensity change at 490nm for a coumarin derivative ECMA reacted with various interferents;
FIG. 8 is a kinetic graph of the effect of the coumarin derivative ECMA on Cys;
FIG. 9 is a graph showing fluorescence emission of the coumarin derivatives ECMA and Cys at different pH;
FIG. 10 is a graph showing fluorescence emission of the coumarin derivatives ECMA and Cys addition products with H 2O2 at 490 nm;
FIG. 11 is an image of a coumarin derivative ECMA assay Cys cells;
FIG. 12 is a cytogram of the effect of the coumarin derivatives ECMA and Cys adducts with H 2O2;
FIG. 13 is a chart of ECMA lysosomal localization of coumarin derivatives.
Detailed Description
The invention provides a coumarin derivative, which has a structure shown in a formula I:
The Chinese name of the coumarin derivative provided by the invention is (E) -3- (7- (diethylamino) -2-oxo-2H-chromen-3-yl) -2- (morpholin-4-formyl) acrylonitrile, the English name is (E) -3- (7- (diethylamino) -2-oxo-2H-chromen-3-yl) -2- (morpholine-4-carboyl) acrylic acid, the coumarin derivative is ECMA, and the probe is a lysosome-targeted ratio Cysteine (Cys) fluorescent probe, and has the advantages of high sensitivity, good selectivity and high response speed for lysosome Cysteine detection.
The invention also provides a preparation method of the coumarin derivative, which comprises the following steps:
mixing 7- (diethylamino) coumarin with an organic solvent to obtain a 7- (diethylamino) coumarin solution;
mixing POCl 3 with an organic solvent to obtain a formylation reagent;
Dropwise adding the 7- (diethylamino) coumarin solution into the formylation reagent to perform formylation reaction to obtain 7- (diethylamino) coumarin-3-formaldehyde;
And mixing the 7- (diethylamino) coumarin-3-formaldehyde, 3-morpholine-3-oxo-propionitrile, piperidine and an organic solvent for Knoevenagel condensation reaction to obtain the coumarin derivative.
In the present invention, all materials used are commercial products in the art unless otherwise specified.
The invention mixes 7- (diethylamino) coumarin with organic solvent to obtain 7- (diethylamino) coumarin solution.
In the present invention, the organic solvent is preferably N, N-Dimethylformamide (DMF).
In the present invention, the 7- (diethylamino) coumarin is preferably commercially available, and the CAS number is 20571-42-0.
Preferably, 0.48g of 7- (diethylamino) coumarin is mixed with 4mL of DMF.
POCl 3 is mixed with an organic solvent to obtain the formylation reagent.
In the invention, 0.6mLPOCl 3 drop is preferably added into 0.8mL DMF, and then stirred and mixed to obtain the formylation reagent.
The stirring time and the rotating speed are not particularly limited, and the raw materials can be uniformly mixed.
After 7- (diethylamino) coumarin solution and formylating reagent are obtained, the 7- (diethylamino) coumarin solution is dripped into the formylating reagent to carry out formylation reaction (Vilsmeier formylation reaction) to obtain 7- (diethylamino) coumarin-3-formaldehyde, and the principle of the formylation reaction is shown as the following formula:
In the invention, the molar ratio of the 7- (diethylamino) coumarin to the POCl 3 is preferably 1:2-1:3, and more preferably 1:2.8.
In the invention, the dripping speed is preferably 1-3 drops/second, and the dripping function is to prevent the reactant from agglomerating due to the formylation reaction, which is unfavorable for further reaction.
In the present invention, the temperature of the formylation reaction is preferably 55 to 65 ℃, more preferably 60 ℃, and the time is preferably 8 to 16 hours, more preferably 12 hours.
After the formylation reaction is finished, the formylation product is preferably obtained by quenching the formylation reaction with ice water, adjusting the pH value to 5-6, filtering the crude product, washing with water and drying in vacuum.
The specific modes of the quenching reaction, pH adjustment, filtration, water washing and vacuum drying are not particularly limited, and modes well known to those skilled in the art can be adopted. In a specific embodiment of the invention, the pH is preferably adjusted using sodium hydroxide solution, preferably at a concentration of 20wt%.
After 7- (diethylamino) coumarin-3-formaldehyde is obtained, the 7- (diethylamino) coumarin-3-formaldehyde, 3-morpholine-3-oxopropionitrile, piperidine and an organic solvent are mixed for Knoevenagel condensation reaction to obtain the coumarin derivative.
In the present invention, the 3-morpholin-3-oxopropionitrile is preferably commercially available, and the CAS number is 15029-32-0.
In the invention, the molar ratio of the 7- (diethylamino) coumarin-3-formaldehyde to the 3-morpholine-3-oxopropionitrile is preferably 1:1-1:2, more preferably 1:1.5.
In the present invention, the ratio of the amount of 7- (diethylamino) coumarin-3-carbaldehyde to the amount of piperidine is preferably 1 mmol/15. Mu.L.
In the present invention, the organic solvent is preferably absolute ethanol.
In the invention, the dosage ratio of the 7- (diethylamino) coumarin-3-formaldehyde to the absolute ethanol is preferably 1 mmol/10 mL.
In the invention, the temperature of the Knoevenagel condensation reaction is preferably 70-90 ℃, more preferably 80 ℃, and the time is preferably 4-6 h, more preferably 5h, and the principle of the Knoevenagel condensation reaction is shown as the following formula:
After the Knoevenagel condensation reaction is finished, the coumarin derivative is preferably obtained by natural cooling to room temperature, reduced pressure distillation and column chromatography separation in sequence.
The specific mode of the reduced pressure distillation is not particularly limited, and may be any mode known to those skilled in the art.
In the present invention, the eluent for the column chromatography is preferably a methanol-dichloromethane mixture, and the volume ratio of methanol to dichloromethane in the methanol-dichloromethane mixture is preferably 1:50.
The invention also provides the coumarin derivative disclosed by the technical scheme or the application of the coumarin derivative prepared by the preparation method disclosed by the technical scheme in qualitative detection of cysteine.
In the present invention, the application preferably includes the steps of:
After mixing the solution to be detected, the PBS buffer solution and the coumarin derivative solution, carrying out fluorescence detection, and if the fluorescence intensity at 572nm is reduced and the fluorescence intensity at 490nm is gradually increased, then the solution to be detected contains cysteine.
In the present invention, the pH of the PBS buffer solution is preferably 5.
The invention also provides the coumarin derivative disclosed by the technical scheme or the application of the coumarin derivative prepared by the preparation method disclosed by the technical scheme in the ratio detection of cysteine.
The invention also provides a method for detecting cysteine by ratio, which comprises the following steps:
Mixing a solution to be detected, a PBS buffer solution and a coumarin derivative solution, respectively measuring fluorescence detection at 490nm and 572nm, and calculating the ratio of fluorescence intensity at 490nm and 572nm, wherein the coumarin derivative in the coumarin derivative solution is the coumarin derivative according to the technical scheme or the coumarin derivative prepared by the preparation method according to the technical scheme, and the solution to be detected contains cysteine;
And calculating the concentration of the cysteine in the solution to be detected by using a standard curve, wherein the standard curve takes the concentration of the cysteine as an abscissa and takes F 490/F572 as an ordinate.
In the present invention, the pH of the PBS buffer solution is preferably 4.0 to 8.0, more preferably 5.0 to 7.0.
In the invention, the concentration of cysteine in the solution to be detected is preferably 0-200 mu M.
The method for obtaining the standard curve is not particularly limited in the present invention, and may be performed in a manner well known to those skilled in the art.
The methods provided by the present invention are described in detail below in conjunction with examples for further illustrating the invention, but they should not be construed as limiting the scope of the invention.
Example 1
Preparation and characterization of ECMA
0.6ML of POCl 3 was slowly added dropwise to 0.8mL of DMF at room temperature, stirred for 2 hours to prepare a formylating reagent, 7- (diethylamino) coumarin (0.48 g,2.2 mmol) was dissolved in 4mL of DMF and added dropwise to the formylating reagent to obtain a suspension. Reflux was performed at 60 ℃ for 12h. And after the reaction is finished, pouring the mixture into 200mL of ice water, and regulating the pH to 5-6 to obtain a large amount of precipitate. The crude product was filtered, washed with water and dried in vacuo to give 7- (diethylamino) coumarin-3-carbaldehyde as an orange solid. The crude product was used directly in the subsequent experiments without further purification.
7- (Diethylamino) coumarin-3-carbaldehyde (0.49 g,2 mmol) and 3-morpholino-3-oxopropanenitrile (0.46 g,3 mmol) were added to a round bottom flask containing 20mL absolute ethanol, followed by 30. Mu.L piperidine. Refluxing at 80 ℃ for 5h, cooling to room temperature, distilling under reduced pressure, and spin-removing the solvent to obtain a crude product. Then methanol/dichloromethane (1/50, v/v) was used as eluent, and separated by column chromatography to obtain an orange-red solid as the target probe, yield 0.32g, yield 41.9%.
Structural characterization:
Hydrogen spectrum ：1H NMR(600MHz,DMSO-d6)δ8.65(s,1H),7.97(s,1H),7.68(s,1H),7.59(d,J＝9.0Hz,1H),7.56(d,J＝9.0Hz,1H),7.44(s,1H),6.82(dd,J＝9.1,2.5Hz,1H),6.79(dd,J＝9.0,2.5Hz,1H),6.64(d,J＝2.6Hz,1H),6.59(d,J＝2.4Hz,1H),3.64-3.59(m,12H),3.53-3.49(m,12H),1.16-1.13(m,12H).( fig. 1).
Carbon spectrum ：13C NMR(151MHz,DMSO-d6)δ162.99,160.55,157.56,153.22,145.77,144.67,143.56,142.60,132.10,131.86,116.93,111.07,110.83,110.64,108.12,108.08,103.16,97.02,96.76,66.36,66.05,47.19,44.95,42.31,12.83.( fig. 2).
Mass spectrum [ m+h ] + theory 382.1761, test 382.1757 (fig. 3).
Example 2
Preparing a PBS buffer solution with pH=5, preparing a DMSO solution with 2mM ECMA, preparing a 20mM Cys aqueous solution, adding 2mL of the PBS buffer solution with pH=5 and 10 mu L of the ECMA DMSO solution into a fluorescence cuvette, and gradually increasing the fluorescence intensity at 572nm and 490nm along with the addition of Cys (0-200 mu M). The fluorescence emission diagrams are shown in fig. 4 and 5.
Example 3
A 20mM Cys solution was prepared with distilled water, a PBS buffer solution at ph=5 was added to a 2mL fluorescence cuvette, and fluorescence titration experiments were performed with different concentrations of Cys. The linear relationship between the Cys concentration and the fluorescence intensity ratio (F 490/F572) is obtained by measuring on a fluorescence spectrophotometer, plotting on an abscissa the Cys concentration and on an ordinate the F 490/F572. A plot of fluorescence intensity ratio (F 490/F572) versus Cys concentration is shown in FIG. 6.
Example 4
Preparing PBS buffer solution with pH=5, preparing DMSO solution with 2mM ECMA, preparing 20mM Cys water solution, adding PBS buffer solution with 2mLpH =5 and DMSO solution with 10 mu LECMA into a fluorescence cuvette, respectively adding other analytes with 10 times equivalent weight and Cys, gly, hcy, glu, pro, arg, asp, met, tyr, lys, lle, trp, ser, thr, his, leu, GSH, naHS and Cys water solution, detecting on a fluorescence spectrophotometer, and drawing a graph of fluorescence intensity change at 490nm after ECMA reacts with different analytes as shown in figure 7. Cys enhances the fluorescence intensity of the detection system at 490nm, and other analytes cause substantially no change in the fluorescence intensity of the detection system.
Example 5
When 10. Mu.L of ECMA in DMSO was added to 2mL of PBS and 200. Mu.M of Cys was added, the fluorescence intensity at 490nm began to rise immediately after the addition and reached equilibrium at about 300 s. The kinetics of ECMA-Cys action is shown in figure 8.
Example 6
Preparing PBS buffer solutions with different pH values, adding 2mL of PBS buffer solution and 10 mu L of ECMA DMSO solution into a cuvette, and detecting fluorescent signals of the probe, wherein the pH value is basically kept stable within a range of 4.0-8.0. Cys is added into the probe solution, and the fluorescence signal at 490nm is slowly increased between pH4.0 and 8.0. The fluorescence emission patterns of ECMA and Cys at different pH are shown in FIG. 9.
Example 7
2ML of PBS buffer solution with pH=5 and 10 mu L of ECMA DMSO solution are added into a cuvette, 200 mu M Cys is added, and then H 2O2 is gradually added into the reaction system, and the fluorescence intensity at 490nm is gradually reduced. The fluorescence emission diagram of ECMA and Cys addition products and H 2O2 acting at 490nm is shown in FIG. 10, which shows that ECMA can reversibly recognize Cys under the condition of pH=5, can reflect redox balance in real time, and when active oxygen substances such as hydrogen peroxide in the system are increased, the addition of the probe and the Cys can be reversely carried out, so that the fluorescence intensity at 490nm is reduced.
Example 8
Preparing PBS buffer solution with pH of 7.4, preparing DMSO solution with 2mM ECMA, preparing 20mM Cys aqueous solution, adding 10 mu L of the ECMA DMSO solution into 2mL of PBS buffer solution, adding the probe solution into HeLa cell culture solution to make the concentration of the probe solution be 10 mu M, incubating for 5min and 20min, and respectively collecting fluorescent signals of channels 1:542-602 nm (lambda ex =488 nm) (orange light) and channels 2:460-520 nm (lambda ex =405 nm) (blue light). Laser confocal fluorescence imaging showed that blue channel fluorescence increased and orange channel fluorescence decreased, indicating that the probe was able to detect endogenous cysteines in the lysosomes, see figure 11.
Example 9
Preparing PBS buffer solution with pH=7.4, preparing DMSO solution of 2mM ECMA, preparing H 2O2 aqueous solution of 20mM, adding 10 mu L of ECMA DMSO solution into 2mL of PBS buffer solution, adding the solution into HeLa cell culture solution, incubating for 10min at 37 ℃, adding H 2O2, increasing (0-10 min) with time, increasing fluorescence signal in orange channel, and obviously decreasing fluorescence signal in blue channel, as shown in figure 12.
Example 10
Preparing PBS buffer solution with pH of 7.4, preparing DMSO solution with 2mM ECMA, preparing 20mM Cys water solution, adding 10 mu L of the ECMA DMSO solution into 2mL of PBS buffer solution, adding the probe solution into HeLa cell culture solution to make the concentration of the probe solution 10 mu M, incubating the probe solution with HeLa cells at 37 ℃ for 10min, observing the system under a fluorescence imager, and then adding 0.2 mu M lysosome staining reagent LTR into the just-prepared system, and incubating the system at 37 ℃ for 30min. The system was observed under a fluorescence imager, and the co-localization ratio was calculated for the obtained fluorescence image with a co-localization coefficient of 0.90, see fig. 13.
The foregoing is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. It should be noted that modifications and adaptations to the present invention may occur to one skilled in the art without departing from the principles of the present invention and are intended to be comprehended within the scope of the present invention.
Claims (10)
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