CN111253420B - A kind of pyrene compound pH value fluorescent probe and its preparation method and application - Google Patents
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Abstract
本发明涉及一种芘类化合物pH值荧光探针及其制备方法和应用。本发明合成的芘类化合物，可以作为pH值荧光探针，用于检测体外和细胞内pH值，其发光能力随pH值的改变而变化。其原因是所述化合物中含有推拉电子体系，pH值的变化会引起推拉电子体系电荷的变化，从而使其荧光发生改变。本发明合成的芘类化合物，对pH的选择具有专一性，荧光信号受阴离子、阳离子、氨基酸和ROS的影响很小，检测结果可信度大大提高。本发明合成的芘类化合物pH值荧光探针，对于pH的检测的范围为4.0‑10.0。本发明合成的芘类化合物pH值荧光探针，可自主进入到细胞中，用于细胞内pH成像。所述荧光探针进入细胞后，在荧光显微镜下可以观察到细胞内pH变化的过程。
The present invention relates to a pyrene compound pH value fluorescent probe and its preparation method and application. The pyrene compounds synthesized in the present invention can be used as pH value fluorescent probes for detecting pH values in vitro and in cells, and the luminescence ability changes with the change of pH value. The reason is that the compound contains a push-pull electron system, and the change of pH value will cause the change of the charge of the push-pull electron system, thereby changing its fluorescence. The pyrene compounds synthesized by the invention have specificity for pH selection, the fluorescence signal is little affected by anions, cations, amino acids and ROS, and the reliability of the detection results is greatly improved. The pH value fluorescent probe of the pyrene compound synthesized in the present invention has a detection range of pH of 4.0-10.0. The pH value fluorescent probe of the pyrene compound synthesized in the present invention can enter into cells autonomously, and is used for intracellular pH imaging. After the fluorescent probe enters the cell, the process of intracellular pH change can be observed under a fluorescence microscope.
Description
Technical Field
The invention relates to a pyrene compound pH value fluorescent probe and a preparation method and application thereof.
Background
pH plays an important role in various physiological activities of cells, such as cell proliferation and apoptosis, multidrug resistance, ion transport, endocytosis and muscle contraction, vesicle transport, cell polarization, and the like. Changes in intracellular pH can affect the operation of intracellular signaling molecules, which in turn can affect intracellular signal transduction. Abnormal cell pH is associated with abnormalities in cell function, growth and division and is also observed in some related common diseases such as cancer and alzheimer's syndrome. In addition, cells from different organs have different pH values, which are also necessary for their maintenance of their normal physiological activities. Cellular dysfunction is often associated with abnormal pH in various organs. Therefore, the real-time and rapid monitoring of the change of intracellular pH plays an important role in understanding the mechanisms of many physiological functions in cells.
Compared with weak acid and weak base distribution methods, microelectrode methods, nuclear magnetic resonance methods and other methods, the fluorescence spectrum detection technology has the advantages of simplicity in operation, high response speed, high signal-to-noise ratio, high sensitivity, no damage to cells in most cases and the like, and is widely applied.
The detection mechanism of the pH fluorescent probe is mainly based on a photoinduced electron transfer mechanism, an intramolecular charge transfer mechanism, a fluorescence resonance energy transfer mechanism, an excimer/complex mechanism, an excited intramolecular proton transfer mechanism and other action mechanisms.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a pyrene compound pH value fluorescent probe and a preparation method and application thereof. The synthesized pyrene compound pH value fluorescent probe has the advantages that: has efficient selectivity to pH; the pH selection has a wide response range (pH is 4.0-10.0); the pyrene compound can realize ratio type fluorescence detection on pH; the pyrene compound can automatically permeate cell membranes into cells by being loaded by nano hydrogel.
The invention provides a pyrene compound, which has a structure shown in the following general formula (I):
wherein R is1、R2Identical or different, independently of one another, from the group consisting of hydroxyl, -NR4R5，R4、R5Identical or different, independently of one another, from C1-10An alkyl group; r3Is aryl, aryl optionally substituted with 1-4 substituents, said substituents being C1-10Alkyl radical, C1-10An alkoxy group.
According to the invention, the alkyl group represents a linear or branched alkyl group having 1 to 10 carbon atoms, preferably a linear or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, etc.
According to the present invention, the aryl group means a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and representative aryl groups include phenyl, naphthyl and the like.
According to the invention, R is3It may be an alkyl-substituted aryl group, such as an alkyl-substituted phenyl group, and in particular may be a phenyl group substituted with three tert-butyl groups.
Preferably, the structure of the pyrene compound is shown as the following formula (Ia):
the invention also provides a preparation method of the compound shown in the general formula (I), which comprises the following steps:
reacting a compound of formula (II), a compound of formula (III) with BR3(OR6)2To obtain a compound of formula (I), wherein R1、R2、R3As defined above, R6Is C1-6An alkyl group.
According to the invention, the aboveIn the reaction, the group R in the compound of the formula (II) and the compound of the formula (III) is firstly reacted1And R2(e.g., hydroxyl, amine) protection (e.g., using a silane group), reaction, and removal of the protecting group.
For example, when R is1And R2When all hydroxyl groups are present, the following specific preparation method can be adopted, including:
(a) reacting a compound represented by the formula (1) with BBr3Reacting to obtain a compound shown as a formula (2);
(b) reacting the compound shown in the formula (2) with tert-butyldimethylsilyl chloride to obtain a compound shown in a formula (3);
(c) reacting a compound represented by the formula (3) with BR3(OR6)2Carrying out a reaction in which R3As defined above, R6Is C1-6Alkyl to obtain a compound shown as a formula (4);
(d) removing the protecting group in the compound shown in the formula (4) to obtain a compound shown in the formula (I);
according to the invention, the solvent in step (a) is selected from dichloromethane.
According to the invention, the compound of formula (1) in said step (a) is reacted with BBr3In a molar ratio of 1: 3.
According to the invention, the reaction in step (a) is carried out under argon protection.
According to the invention, the temperature of the reaction in step (a) is between 0 and 20 ℃ and the reaction time is between 8 and 16h, for example 12 h.
According to the invention, the molar ratio of the compound shown in the formula (2) in the step (b) to the tert-butyldimethylsilyl chloride is 1: 1.5.
According to the present invention, imidazole is added as catalyst in said step (b) in an amount conventionally selected in the art.
According to the invention, the reaction in step (c) is carried out under argon protection.
According to the invention, the temperature of the reaction in step (c) is preferably lower than-40 ℃, for example-80 to-70 ℃, for example-78 ℃ and the reaction time is 8 to 12 hours.
According to the invention, the solvent in step (d) is selected from tetrahydrofuran.
According to the present invention, in the step (d), the reaction for removing the protecting group may be carried out, for example, in tetrabutylammonium fluoride.
The invention also provides application of the pyrene compound, which can be used as a pH value fluorescent probe for detecting the pH value.
According to the invention, the pH value fluorescent probe is used for intracellular pH imaging and detecting the change process of intracellular pH.
According to the invention, the pH fluorescent probe is used for detecting the pH value in an aqueous solution.
Preferably, the pH value fluorescent probe has a response range to pH of 4.0-10.0 in an aqueous solution.
The invention also provides a pH value fluorescent probe which comprises the pyrene compound.
According to the invention, the pyrene compound is loaded on the nano hydrogel.
The invention has the beneficial effects that:
1. the pyrene compound synthesized by the invention can be used as a pH value fluorescent probe for detecting the pH value in vitro and in cells, and the luminous capacity of the pyrene compound is changed along with the change of the pH value. The reason for this is that the compound contains a push-pull electron system, and the change in pH causes a change in charge of the push-pull electron system, thereby changing the fluorescence.
2. The pyrene compound synthesized by the invention has specificity on the selection of pH, the fluorescent signal is slightly influenced by anions, cations, amino acids and ROS, and the reliability of the detection result is greatly improved.
3. The synthesized pyrene compound pH value fluorescent probe has the pH value detection range of 4.0-10.0.
4. The synthesized pyrene compound pH value fluorescent probe can automatically enter cells and is used for intracellular pH imaging. After the fluorescent probe enters the cell, the process of intracellular pH change can be observed under a fluorescent microscope.
5. The synthesized pyrene compound pH value fluorescent probe has the advantages of high efficiency and specificity, light stability, wide response range and the like.
Drawings
FIG. 1 is a graph showing fluorescence spectra of NG-DPTB-OH prepared in example 4 in phosphate buffered solutions of different pH values as a function of pH.
FIG. 2 shows the reversible fluorescence change of NG-DPTB-OH prepared in example 4 in phosphate buffer solutions with different pH values.
FIG. 3 is a bar graph of interference detection of the NG-DPTB-OH probe prepared in example 4.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are only for illustrating the present invention and are not intended to limit the scope of the present invention. In addition, it should be understood that various changes or modifications can be made by those skilled in the art after reading the disclosure of the present invention, and such equivalents also fall within the scope of the invention.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; reagents, materials and the like used in the following examples are commercially available unless otherwise specified.
Example 1
Preparation of 6-bromo-1-hydroxypyrene (1-a) and 8-bromo-1-hydroxypyrene (1-b)
Under the protection of argon, 10g (0.032mol) of 6-bromomethoxypyrene and 8-bromomethoxypyrene and anhydrous dichloromethane (100mL) were added to a 250-mL round-bottom flask. Dropwise adding BBr under ice bath condition3(4mL) and reacted at room temperature for 12 hours. Washing with water after the reaction is finished, extracting with ethyl acetate and anhydrous MgSO4Drying, filtering, spin-drying, and adding acetic acidThe ethyl ester/petroleum ether was chromatographed on silica gel (volume ratio of ethyl acetate/petroleum ether 1:20) to give a white solid powder (9.1g, 95%).
Example 2
Preparation of 6-bromo-1-tert-butyldimethylsilyloxypyrene (2-a) and 8-bromo-1-tert-butyldimethylsilyloxypyrene (2-b)
7g of 6-bromo-1-hydroxypyrene and 8-bromo-1-hydroxypyrene prepared in example 1 (0.023mol), 6.5mL of t-butyldimethylsilyl chloride (0.035mol) and 4g of imidazole (0.059mol) were dissolved in 300mL of DMF. The reaction was carried out at room temperature for 2 hours, dried by spinning and chromatographed on a silica gel column using petroleum ether/dichloromethane (petroleum ether/dichloromethane ratio by volume 20:1) to give a yellow solid powder (9.7g, 100%).
Example 3
Preparation of bis (6- (dimethyl t-butylsiloxy) pyrene-1-yl) (2,4, 6-triisopropylphenyl) boron (3-a), bis (8- (dimethyl t-butylsiloxy) pyrene-1-yl) (2,4, 6-triisopropylphenyl) boron (3-b) and (6- (dimethyl t-butylsiloxy) pyrene-1-yl) (8- (dimethyl t-butylsiloxy) pyrene-1-yl) (2,4, 6-triisopropylphenyl) boron (3-c)
4g of 6-bromo-1-tert-butyldimethylsilyloxypyrene and 8-bromo-1-tert-butyldimethylsilyloxypyrene (9mmol) prepared in example 2 were dissolved in 50mL of degassed ether under an argon atmosphere, and a 1N-butyllithium solution in ethane (2.2M) was added thereto at-78 ℃ to slowly return to room temperature, followed by reaction for 2 hours, cooling again to-78 ℃ to which 0.45N of 2,4, 6-triisopropylphenylboronate was added thereto to slowly return to room temperature, followed by reaction overnight, dilution with dichloromethane, washing with water, drying with magnesium sulfate, and silica gel column chromatography using petroleum ether/ethyl acetate (petroleum ether/ethyl acetate volume ratio: 50:1) to obtain a yellow solid powder (5.1g, 60%).
Example 4
Preparation of bis (6-hydroxypyren-1-yl) (2,4, 6-triisopropylphenyl) boron, a compound of formula (Ia)
2g of the compounds (3-a), (3-b) and (3-c) (4mmol) prepared in example 3 and 3.6g of tetrabutylammonium fluoride (13mmol) were dissolved in 100ml of tetrahydrofuran solvent and reacted at room temperature for 2 hours. After the reaction, the reaction solution was neutralized with 2M diluted hydrochloric acid, washed with water, dried over anhydrous magnesium sulfate, filtered, spin-dried, and chromatographed on silica gel with petroleum ether/dichloromethane to give a yellow solid powder (2.9g, 99%) as formula (Ia) and designated DPTB-OH.
And (4) analyzing results:
HRMS(ESI)m/z[M-H]+calc.:647.31159found:647.31242.1H-NMR(400MHz,DMSO),δ:11.16(s,2H),8.66(d,2H,J＝9.2Hz),8.49(d,2H,J＝8Hz),8.42(d,2H,J＝9.2Hz),8.19(d,10H,J＝7.6Hz),7.15(s,2H),3.03(m,1H),2.90(m,2H),1.31(d,6H,J＝6.8Hz),0.93(s,6H,J＝6Hz),0.68(s,6H,J＝6Hz)。
example 5
DPTB-OH prepared in example 4 was used for pH detection:
the DPTB-OH is loaded by the polyurethane hydrogel, and the obtained product is recorded as NG-DPTB-OH, wherein the concentration of the DPTB-OH in the polyurethane hydrogel is 10-6M (mol/L). Preparing phosphate buffer solutions with different pH values (pH values are respectively 4,5,6,6.5,7,7.5,8,8.5,9 and 10), and finally measuring fluorescence spectra of the NG-DPTB-OH under different pH values, wherein the results are shown in figure 1, and the pH represented by curves from top to bottom at 550nm in figure 1 is 4,5,6,6.5,7,7.5,8,8.5,9 and 10 in sequence (in figure 1, the fluorescence spectra of the NG-DPTB-OH under the conditions of pH 4 and pH 5 are slightly overlapped, but the curve of pH 4 is positioned above the curve of pH 5); as can be seen from FIG. 1, the emission spectrum of NG-DPTB-OH is red-shifted with increasing pH, and the light emission intensity at 550nm gradually decreases, and the light emission color gradually changes from green to red. Further NG-DPTB-OH showed good reversibility between pH 4.0 and 9.0 (see FIG. 2). Furthermore, NG-DPTB-OH has specificity to the selection of pH, the fluorescent signal is slightly influenced by anions, cations, amino acids and ROS (reactive oxygen species, wherein GSH is glutathione, and Cys is cysteine), the reliability of the detection result is greatly improved, and specifically, as shown in FIG. 3, the fluorescence intensity ratio (I) of NG-DPTB-OH at two wavelengths is550nm/I650nm) No significant change occurred with the addition of each ion or molecule. Among them, calcium ion, copper ion, sodium ion, zinc ion and cysteine have a small influence on the ratio because the concentration of ions and molecules used in the in vitro detection is far higher than the concentration in the cell body and thus can be ignored.
Example 6
DPTB-OH prepared in example 4 was used for intracellular pH imaging:
the polyurethane hydrogel is used for loading DPTB-OH, and the concentration of the obtained NG-DPTB-OH is 10-6M, adjusting the pH value inside and outside the cell to be consistent by adding an ion carrier nigericin into a culture medium with high-concentration potassium ions. Finally, the fluorescence intensity in the cells in the green channel is measured to be weakened along with the increase of the pH; in contrast, the fluorescence intensity in the cells in the red channel increases with increasing pH. In addition, the change of pH value can be obviously seen from the comparison of the ratio picture of the fluorescence intensity of the green channel and the red channel and the false color bar.
Wherein, the red channel refers to the collected fluorescence intensity of 570-650nm waveband, and the green channel refers to the collected fluorescence intensity of 470-550nm waveband.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. 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.
Claims (13)
1. A pyrene compound has a structure shown in the following general formula (I):
wherein R is1、R2Same, selected from hydroxyl; r3Is aryl, aryl optionally substituted with 1-4 substituents, said substituents being C1-10Alkyl radical, C1-10An alkoxy group; the aryl group means a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.
2. The pyrene-based compound of claim 1, wherein R is3Is C1-10Alkyl-substituted phenyl.
3. The pyrene-based compound of claim 1, wherein R is3Is phenyl substituted with three tert-butyl groups.
4. The pyrene compound according to any one of claims 1 to 3, wherein the structure of the pyrene compound is represented by the following formula (Ia):
5. the method for producing pyrene compounds according to any one of claims 1 to 4, comprising the steps of:
reacting a compound of formula (II), a compound of formula (III) with BR3(OR6)2To obtain a compound of formula (I), wherein R1、R2、R3As defined in any one of claims 1 to 3, R6Is C1-6An alkyl group.
6. The process according to claim 5, wherein the reaction comprises reacting the compound of formula (II) with the group R of the compound of formula (III)1And R2Protection is carried out, the reaction is carried out again, and then the protecting group is removed.
7. The production method according to claim 5 or 6, wherein the following specific production method is employed, including:
(a) reacting a compound represented by the formula 1 with BBr3Reacting to obtain a compound shown as a formula 2;
(b) reacting the compound shown in the formula 2 with tert-butyldimethylsilyl chloride to obtain a compound shown in a formula 3;
(c) reacting a compound represented by the formula 3 with BR3(OR6)2Carrying out a reaction in which R3As defined above, R6Is C1-6Alkyl to obtain a compound shown as a formula 4;
(d) removing the protecting group in the compound shown in the formula 4 to obtain the compound shown in the formula (I).
8. The preparation method of claim 7, wherein the solvent in step (a) is selected from dichloromethane, the reaction temperature in step (a) is 0-20 ℃, and the reaction time is 8-16 h;
imidazole is added as a catalyst in the step (b);
the reaction temperature in the step (c) is lower than-40 ℃, and the reaction time is 8-12 h;
the solvent in step (d) is selected from tetrahydrofuran; in the step (d), the reaction for removing a protecting group is carried out in tetrabutylammonium fluoride.
9. Use of the pyrene compound according to any one of claims 1 to 4 as a pH fluorescent probe for detecting pH.
10. The use according to claim 9, wherein the pH fluorescent probe is used for intracellular pH imaging to detect the change process of intracellular pH.
11. The use according to claim 9, wherein the pH fluorescent probe is used for detecting pH in an aqueous solution.
12. A pH fluorescent probe comprising the pyrene compound according to any one of claims 1 to 4.
13. The pH fluorescent probe of claim 12, wherein the pyrene compound is supported on a nanohydrogel.
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