CN113563354A - Difunctional fluorescent probe for detecting alkaline pH and/or viscosity and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a bifunctional fluorescent probe for detecting alkaline pH and/or viscosity, and a preparation method and application thereof. The fluorescent probe is 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one. The invention uses 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxo-bicyclo [2.2.1] hepta-2-ylidene) methyl) benzaldehyde as a raw material to carry out condensation reaction with 1, 2, 3, 3-tetramethyl-3H-indole iodide to obtain 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one. The compound can sensitively detect alkaline pH and viscosity, is green fluorescent in an alkaline solution, and is red fluorescent in a high-viscosity medium, so the compound can be used as a dual-function fluorescent probe for detecting the alkaline pH and the viscosity, has good sensitivity, and has a potential application prospect.
Description
Technical Field
The invention belongs to the technical field of fine organic synthesis, and relates to a bifunctional fluorescent probe for detecting alkaline pH and/or viscosity, and a preparation method and application thereof.
Background
The microenvironment of a cell is an important factor influencing the physical or chemical behavior of surrounding molecules, and the stabilization of the microenvironment is an important condition for maintaining various functional activities of the cell. Viscosity is an important microenvironment parameter that controls almost all cell diffusion-mediated processes, such as intracellular/intercellular signal transduction, biomacromolecule interactions, and diffusion of cellular metabolites. Studies have shown that abnormal cell viscosity is a key indicator for diagnosing various diseases (such as atherosclerosis, diabetes, cancer). pH is another important microenvironment parameter, and a series of biological processes such as cell proliferation, apoptosis, endocytosis and the like all depend on the maintenance of pH homeostasis. Due to the uneven distribution of protons, different organelles and cytoplasm show different pH values, and the abnormal pH value of any cell region can cause cell dysfunction, thereby causing other diseases such as Alzheimer's disease, cancer and the like. Therefore, it is essential to develop a reliable and effective means to monitor changes in viscosity and pH during different physiological and pathological processes.
It is not feasible to use conventional pH meters and viscometers for measuring macroscopic volumes to determine pH and viscosity values in living cells. However, the fluorescence probe method has the advantages of simple operation, high sensitivity, fast response, high space-time resolution and the like, and is a powerful tool for in vivo detection. In recent years, many pH or viscosity sensitive fluorescent probes have been reported. In a specific microenvironment, two important parameters of pH and viscosity need to be considered simultaneously, which requires the cooperative work of a plurality of single-response fluorescent probes, and inevitably causes problems of different spectra clustering, different positioning and the like. In contrast, fluorescent probes that can simultaneously detect both pH and viscosity are more attractive, but few dual-response fluorescent probes are currently reported. In addition, most of the reported pH fluorescent probes respond only to acidity, and few of the reported fluorescent probes are capable of detecting alkaline pH. Therefore, the design and development of the bifunctional fluorescent probe capable of sensitively responding to the alkaline pH and the viscosity simultaneously has very important research significance.
Disclosure of Invention
Aiming at the defects in the prior art, the technical problem to be solved by the invention is to provide a bifunctional fluorescent probe for detecting alkaline pH and/or viscosity, and the use requirement for detecting alkaline pH and/or viscosity is met. The invention aims to provide a preparation method of the fluorescent probe. The invention also aims to solve the technical problem of providing the application of the bifunctional fluorescent probe.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the difunctional fluorescent probe for detecting the alkaline pH and the viscosity is 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one, and the structural formula is as follows:
the preparation method of the bifunctional fluorescent probe for detecting alkaline pH and viscosity comprises the step of carrying out condensation reaction on 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) methyl) benzaldehyde and 1, 2, 3, 3-tetramethyl-3H-indole iodide to obtain 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one.
The preparation method comprises the following specific steps:
(1) sequentially adding 1mmol of 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) methyl) benzaldehyde, 1mmol of 1, 2, 3, 3-tetramethyl-3H-indolium iodide, 30mL of anhydrous ethanol and 20 mu L of piperidine into a dry three-neck flask, and stirring and refluxing for 8 hours;
(2) the reaction solution was distilled under reduced pressure to remove ethanol to give a crude 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one, which was then separated by silica gel column (ethyl acetate/petroleum ether ═ 1/6, v/v) to give a pure 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one.
The 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one is applied to detection of alkaline pH and/or viscosity.
The 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one is applied to the preparation of a fluorescent probe.
The 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one is used as a fluorescent probe in the application of alkaline pH and/or viscosity.
Has the advantages that: compared with the prior art, the invention carries out condensation reaction on 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) methyl) benzaldehyde and 1, 2, 3, 3-tetramethyl-3H-indolium iodide to obtain 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indoline ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one. The compound can sensitively detect alkaline pH and viscosity, is green fluorescent in an alkaline solution, and is red fluorescent in a high-viscosity medium, so that the compound can be used as a bifunctional fluorescent probe for detecting alkaline pH and/or viscosity, and has potential application prospects.
Drawings
FIG. 1 is a graph of the fluorescence spectra of 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one in solutions of different alkaline pH;
FIG. 2 is a graph of the non-linear fit of the fluorescence intensity to pH for 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one;
FIG. 3 is a graph of the fluorescence spectra of 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one in media with different viscosities.
FIG. 4 is a plot of fluorescence intensity versus viscosity for 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with figures are described in detail below.
Example 1
Synthesis of 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one, reaction formula:
1mmol of 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxobicyclo [2.2.1]]Hept-2-ylidene) methyl) benzaldehyde, 1mmol of 1, 2, 3, 3-tetramethyl-3H-indolium iodide, 30mL of absolute ethanol and 20. mu.L of piperidine were added in this order to a dry three-necked flask, and stirring and refluxing were carried out for 8 hours. The reaction solution is subjected to reduced pressure distillation to remove ethanol to obtain 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline)]-6-yl) methylene) bicyclo [2.2.1]The crude hept-2-one was separated by silica gel column (ethyl acetate/petroleum ether: 1/6, v/v) to give light orange crystalsThe isomer 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indoline)]-6-yl) methylene) bicyclo [2.2.1]The yield of the pure hepta-2-ketone product is 75 percent, and the purity is 98 percent;1H NMR(600MHz，DMSO-d6)δ：7.41(s，1H)，7.33(d，J＝6Hz，2H)，7.08-7.12(m，3H)，7.00(s，1H)，6.78(t，J＝12Hz，1H)，6.75(d，J＝6Hz，1H)，6.58(d，J＝6Hz，1H)，5.83(d，J＝6Hz，1H)，3.15-317(m，1H)，2.66(s，3H)，2.13-2.16(m，1H)，1.74-1.78(m，1H)，1.41-1.45(m，1H)，1.32-1.36(m，1H)，1.21(s，3H)，1.10(s，3H)，0.97(s，3H)，0.91(s，3H)，0.72(s，3H)；13C NMR(150MHz，DMSO-d6)δ：206.12，155.17，148.19，136.59，132.11，129.60，128.99，127.94，127.66，126.69，121.93，120.36，119.51，119.33，115.43，107.30，105.01，60.19，56.74，51.95，48.90，46.74，30.63，28.98，26.12，20.63，20.24，18.43，14.53，9.74；HRMS(ESI+)：m/z calculated for C30H34NO2[M+H]+440.2585，found 440.2590。
example 2
Dissolving sodium hydroxide in a system of ethanol/water (v/v ═ 4/6), diluting to obtain alkaline solutions with different pH values (7.140, 7.451, 7.782, 7.995, 8.253, 8.534, 8.934, 9.156, 9.406, 9.752, 9.996, 10.365, 10.565, 10.88, 11.295, 11.709, 12.401), adding 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline)]-6-yl) methylene) bicyclo [2.2.1]Hept-2-one to give a final concentration of 1X 10-5And M. The 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indoline) was measured in solutions of different pH values]-6-yl) methylene) bicyclo [2.2.1]Fluorescence emission spectrum of hepta-2-one (FIG. 1), the result shows that the green fluorescence of the probe gradually increases with the increase of the alkalinity of the solution. The fluorescence intensity at 518nm was fitted non-linearly to the pH to give a curve as shown in FIG. 2, and further calculated to give a pKa value of 10.25. The fluorescence intensity at 518nm is linearly related to pH in the range of 9.406 to 11.295 for solution pH, and the linear equation is F518nm＝341.54pH-3041.73(R20.9724). Therefore, the probe can sensitively detect alkaline pH.
Example 3
Prepared by ethanol and glycerol with different volume ratios (V)Ethanol/V Glycerol10/0, 9.5/0.5, 9/1, 8.5/1.5, 8/2, 7.5/2.5, 7/3, 6.5/3.5, 6/4, 5.5/4.5, 5/5, 4.5/5.5, 4/6, 3.5/6.5, 3/7, 2.5/7.5, 2/8, 1.5/8.5, 1/9) and a viscosity of 1.14, 1.56, 2.12, 2.33, 3.43, 4.84, 6.54, 10.45, 13.3, 17.15, 22.2, 29.2, 44.4, 64.8, 94.0, 133.5, 204.5, 278.0, 392.0, 627.5cP, respectively, as measured with a viscometer. Adding 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline)]-6-yl) methylene) bicyclo [2.2.1]Hept-2-one to give a final concentration of 1X 10-5M, ultrasonic treatment for 5min to eliminate bubbles, and measuring that 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethyl spiro [ benzopyran-2, 2' -indoline) in systems with different viscosities]-6-yl) methylene) bicyclo [2.2.1]Fluorescence emission spectrum of heptan-2-one (FIG. 3), the result shows that the red fluorescence of the probe gradually increases with the increase of the system viscosity. The correlation curve of fluorescence intensity at 602nm with viscosity is shown in FIG. 4, and the viscosity ranges from 22.2 to 392.0cP, log I602nmIs linearly related to log eta, and the fitting curve is log I602nm＝0.4245logη+1.8270(R20.9968). Therefore, the probe can sensitively detect a change in viscosity.
Claims (6)
1. A bifunctional fluorescent probe for detecting alkaline pH and/or viscosity, characterized in that it has the structural formula:
2. the method of claim 1, wherein 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) methyl) benzaldehyde is condensed with 1, 2, 3, 3-tetramethyl-3H-indolium iodide to obtain 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] hept-2-one.
3. The method for preparing a bifunctional fluorescent probe for detecting alkaline pH and/or viscosity according to claim 2, comprising the following steps:
(1) sequentially adding 1mmol of 2-hydroxy-5- ((4, 7, 7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) methyl) benzaldehyde, 1mmol of 1, 2, 3, 3-tetramethyl-3H-indolium iodide, 30mL of anhydrous ethanol and 20 mu L of piperidine into a dry three-neck flask, and stirring and refluxing for 8 hours;
(2) the reaction solution was distilled under reduced pressure to remove ethanol to give a crude 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one, which was then separated by silica gel column (ethyl acetate/petroleum ether ═ 1/6, v/v) to give a pure 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one.
4. Use of 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one according to claim 1 for detecting alkaline pH and/or viscosity.
5. Use of 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one according to claim 1 for the preparation of a fluorescent probe.
6. Use of 1, 7, 7-trimethyl-3- ((1 ', 3', 3 '-trimethylspiro [ benzopyran-2, 2' -indolin ] -6-yl) methylene) bicyclo [2.2.1] heptan-2-one according to claim 1 as a fluorescent probe at alkaline pH and/or viscosity.
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| CN109232444A (en) * | 2018-11-20 | 2019-01-18 | 南京林业大学 | A kind of camphor base fluorescent probe and preparation method thereof for detecting hydrazine |
| CN110317199A (en) * | 2019-07-24 | 2019-10-11 | 南京林业大学 | A kind of australene basal cell nuclear fluorescence probe and its preparation method and application |
| CN110317158A (en) * | 2019-06-12 | 2019-10-11 | 兰州大学 | A kind of synthesis of double-mode optical probe indoles iodide and its detection to uns-dimethylhydrazine |
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| CN109232444A (en) * | 2018-11-20 | 2019-01-18 | 南京林业大学 | A kind of camphor base fluorescent probe and preparation method thereof for detecting hydrazine |
| CN110317158A (en) * | 2019-06-12 | 2019-10-11 | 兰州大学 | A kind of synthesis of double-mode optical probe indoles iodide and its detection to uns-dimethylhydrazine |
| CN110317199A (en) * | 2019-07-24 | 2019-10-11 | 南京林业大学 | A kind of australene basal cell nuclear fluorescence probe and its preparation method and application |
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