CN113666843A - Large-Stokes-shift fluorescent probe for detecting viscosity and preparation and application thereof - Google Patents

Large-Stokes-shift fluorescent probe for detecting viscosity and preparation and application thereof Download PDF

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CN113666843A
CN113666843A CN202110931389.1A CN202110931389A CN113666843A CN 113666843 A CN113666843 A CN 113666843A CN 202110931389 A CN202110931389 A CN 202110931389A CN 113666843 A CN113666843 A CN 113666843A
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fluorescent probe
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CN113666843B (en
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谢振达
吴柏旭
赖燕琴
黎兆凯
程翎
周弈宇
李铭敏
祝子坪
杨仲毅
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Zhejiang Luoxi Medical Technology Co ltd
Taizhou University
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Abstract

The application discloses a large Stokes displacement fluorescent probe for detecting viscosity, and preparation and application thereof, wherein the molecular formula of the probe is C26H24N2O, structural formula is shown as formula (I):
Figure DDA0003210904150000011
mixing the compound (2) and the compound (3), adding acetonitrile and piperidine, and heating the mixture under the protection of nitrogen to obtain a reaction solution; carrying out spin drying, separation and purification on the reaction liquid to prepare the large Stokes shift fluorescent probe;

Description

Large-Stokes-shift fluorescent probe for detecting viscosity and preparation and application thereof
Technical Field
The application relates to the field of small molecule fluorescent probes, in particular to a large Stokes shift fluorescent probe for detecting viscosity and preparation and application thereof.
Background
Viscosity plays a crucial role in the biological microenvironment. The viscosity of different regions of the cell varies widely and therefore also affects the diffusion of active molecules in the respective regions, such as signal transmission, substance transport, interactions between biochemical substances, etc. Abnormal levels of cell viscosity have been found in many studies to be often associated with various diseases such as cancer, cardiovascular disease, depression, diabetes and alzheimer's disease. Therefore, there is an urgent need to develop an effective tool for detecting viscosity change in cells, which has an important role in promoting disease prevention and developing clinical diagnosis.
Compared with other detection methods, fluorescent probes have been used for detecting viscosity values in cells/living bodies due to the advantages of simple preparation method, high sensitivity, living cell/living body visualization and the like. However, most of the viscosity fluorescent probes reported at present have the defect of small stokes shift, and are easy to have a serious self-quenching phenomenon, and the detection result is interfered by excitation light of an instrument, so that a large measurement error is caused.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a large Stokes shift fluorescent probe for detecting viscosity.
Large Stokes displacement fluorescent probe for detecting viscosity, and molecular formula of probe is C26H24N2O, structural formula is shown as formula (I):
Figure BDA0003210904130000021
the application also provides a preparation method of the large Stokes shift fluorescent probe, which comprises the following steps:
mixing the compound (2) and the compound (3), adding acetonitrile and piperidine, and heating the mixture under the protection of nitrogen to obtain a reaction solution; carrying out spin drying, separation and purification on the reaction liquid to prepare the large Stokes shift fluorescent probe;
Figure BDA0003210904130000022
the synthetic route is as follows:
Figure BDA0003210904130000023
optionally, the molar ratio of the compound (2), the compound (3) and the piperidine is 1: 1-1.5: 0.1.
optionally, the acetonitrile is used as a solvent.
Optionally, the reaction conditions for heating the mixture under the protection of nitrogen are as follows: reacting for 10-14 hours at 60-80 ℃.
Alternatively, the separation and purification method may be as follows: concentrating the reaction solution under reduced pressure, and separating and purifying by silica gel column chromatography, wherein the volume ratio of the eluent is 1:3 ethyl acetate: petroleum ether to obtain the fluorescent probe (I).
The compound (2) of the present application is a compound disclosed therein, and its preparation method can be referred to in the literature (Homma H, Harada S, Ito T, Kanda A, et al. an oral pharmaceutical synergistic reaction of beta-naphthols with diazoacetic acid using a solvent catalyst [ J ] Organic Letters,2020,22: 8132-.
The compound (3) of the present invention is a disclosed compound, and its preparation method can be referred to in the literature (Wu Y, Yu WT, Hou T C, et al. A selective and reactive fluorine album protocol for the determination of the raw album [ J ]. Chemical Communications,2014,50: 11507-11480.).
The application also provides an application of the large Stokes shift fluorescent probe in preparation of a viscosity detection product.
Optionally, the viscosity detection product is a viscosity detection reagent or a viscosity detection kit.
Optionally, the viscosity detection product is used to detect viscosity in cells or viscosity in solution.
Alternatively, the cell is human lung cancer cell a 549.
The application also provides an application of the large Stokes shift fluorescent probe in preparation of a fluorescent imaging product.
Optionally, the fluorescence imaging product is a fluorescence imaging reagent or a fluorescence imaging kit.
The fluorescent probe can be applied to the quantitative detection of the viscosity value of a solution, and the method comprises the following steps:
and adding the fluorescent probe into the solution to be detected, uniformly mixing, performing ultrasonic treatment, standing, collecting the fluorescence intensity of the solution at the excitation wavelength of 440nm and the emission wavelength of 628nm, and calculating according to a standard curve to obtain the viscosity value of the solution to be detected.
Optionally, the addition amount of the large stokes shift fluorescent probe capable of detecting viscosity in the solution to be detected is calculated by the ratio of the molar weight of the fluorescent probe to the viscosity in the solution: 0.005mM fluorescent probe: the viscosity is 1-109 cP. Under the proportioning condition, the fluorescence intensity at 628nm is taken as the ordinate and the solution viscosity is taken as the abscissa, and a linear relation graph is made, so that the fluorescence intensity and the solution viscosity have a good linear relation in the range of 1-109 cP, and the linear equation is as follows: y is 29.65x +711.47 (R)2＝0.999)。
Alternatively, the standard curve is prepared as follows:
and (3) respectively mixing the 0.005mM fluorescent probe with a solution with the viscosity of 1-109 cP, collecting the fluorescence intensity of the solution under the excitation wavelength of 440nm and the emission wavelength of 628nm, and drawing by taking the fluorescence intensity as a vertical coordinate and the solution viscosity as a horizontal coordinate to obtain a linear standard curve.
Optionally, the linear equation of the linear standard curve is: y is 29.65x +711.47 (R)2＝0.999)
Alternatively, the pH of the solution when the viscosity is measured is 7.4.
The fluorescent probes of the present application can also be used for the detection of viscosity changes in cells for non-diagnostic purposes. The viscosity change can be detected within the range of the excitation wavelength of 488nm and the emission and receiving wavelengths of 580-680 nm.
Alternatively, the cell is human lung cancer cell a 549.
Compared with the prior art, the invention has the beneficial effects that: the fluorescent probe provided by the invention has the advantages of simple preparation method, large Stokes shift property, capability of avoiding the interference of instrument exciting light and reducing detection errors, and can be used for detecting the change of solution and intracellular viscosity.
Drawings
FIG. 1 shows nuclear magnetic hydrogen spectra of the fluorescent probe (I) prepared in example 1.
FIG. 2 shows nuclear magnetic carbon spectrum of the fluorescent probe (I) prepared in example 1.
FIG. 3 is a graph showing UV-VIS absorption spectra of the probe (I) prepared in example 1 in various solvents.
FIG. 4 is a graph showing fluorescence spectra of the probe (I) prepared in example 1 in different solvents.
FIG. 5 is a graph showing fluorescence intensities of the probe (I) prepared in example 1 in different solvents at an excitation wavelength of 440nm and an emission wavelength of 628 nm.
FIG. 6 is a graph showing fluorescence spectra of probe (I) prepared in example 1 in glycerol-PBS solutions at different ratios.
FIG. 7 is a graph showing the linear relationship between the fluorescence intensity and the viscosity of the solution at an excitation wavelength of 440nm and an emission wavelength of 628nm for the probe (I) prepared in example 1.
FIG. 8 is a graph showing fluorescence intensities of the probe (I) prepared in example 1 at different pH values at an excitation wavelength of 440nm and an emission wavelength of 628 nm.
FIG. 9 is a graph of the anti-interference fluorescence intensity of probe (I) prepared in example 1.
FIG. 10 is an image of probe (I) prepared in example 1 in cells of different viscosities.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
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 application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
Example 1: preparation of fluorescent Probe (I)
Compound (2) (0.5mmol) and compound (3) (0.6mmol) were placed in a round bottom flask, followed by the addition of 5mL acetonitrile and piperidine (0.05mmol) and the mixture was heated under nitrogen for 12 hours at 70 ℃. And (3) spin-drying the reaction liquid, and separating and purifying by using a silica gel column chromatography, wherein the developing agent is ethyl acetate: petroleum ether was 1:3 (by volume), and a large Stokes shift fluorescent probe (I) was prepared (0.11g, 57.9% yield).
The synthetic route is as follows:
Figure BDA0003210904130000061
the nuclear magnetic hydrogen spectrum and the nuclear magnetic carbon spectrum of the large Stokes shift fluorescent probe (I) are respectively shown in FIG. 1 and FIG. 2.
1H NMR(400MHz,DMSO-d6)δ8.11–8.06(m,1H),7.90–7.79(m,3H),7.53–7.33(m,3H),7.22(dd,J＝8.9,2.6Hz,1H),6.90(s,1H),6.12(ddt,J＝17.2,10.5,5.3Hz,1H),5.47(dq,J＝17.2,1.7Hz,1H),5.31(dq,J＝10.5,1.5Hz,1H),4.71(dt,J＝5.4,1.6Hz,2H),2.60(d,J＝13.6Hz,4H),1.03(s,6H).13C NMR(101MHz,DMSO-d6)δ170.74,157.59,156.53,138.40,135.38,133.89,131.96,130.51,129.37,129.28,128.90,127.86,125.07,122.93,119.81,118.24,114.42,113.61,107.92,76.36,68.84,42.78,38.68,32.16,27.93.
Example 2: and (3) testing the ultraviolet visible light absorption intensity and the fluorescence intensity of the fluorescent probe (I) in different solvents.
Accurately weighing a certain amount of fluorescent probe (I), preparing mother liquor with the concentration of 10mM by using dimethyl sulfoxide, sucking 40 mu L by a liquid transfer gun, adding the mother liquor into 4mL of different solvents to be tested (1-13 are respectively 1, 4-dioxane, tetrahydrofuran, ethyl acetate, chloroform, dichloromethane, acetone, dimethyl sulfoxide, N-dimethylformamide, acetonitrile, methanol, water, ethanol and glycerol), shaking, mixing uniformly, adding into a cuvette, and testing by using an ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer respectively.
As shown in FIG. 3, the optimal absorption peak and the absorption intensity of the fluorescent probe (I) in different solvents are different, wherein the optimal absorption peak in glycerol is at 440 nm. From fig. 4 and 5, it is found that when fluorescence excitation scanning is performed at an excitation wavelength of 440nm, the fluorescence intensity of the probe in glycerol, which is a high viscosity solvent, is highest (emission peak is located at 628nm) compared to other low viscosity solvents. The data prove the capability of the fluorescent probe (I) to respond to the viscosity of the solution, the difference between an emission peak and an excitation peak is 188nm, and the fluorescent probe has the property of large Stokes shift.
Example 3: fluorescence spectra of fluorescent probes (I) in glycerol-PBS solutions at different ratios.
Accurately weighing a certain amount of fluorescent probe (I), preparing a mother solution with the concentration of 10mM by using dimethyl sulfoxide, sucking 40 mu L of the mother solution by using a pipette gun, adding the pipette probe into 4mL of glycerol-PBS solvents (10%, 20%, 40%, 50%, 70%, 80% and 90%) with different proportions (volume ratio), shaking, uniformly mixing, carrying out ultrasonic treatment, adding the mixture into a cuvette, and testing by using a fluorescence spectrophotometer.
As can be seen from FIG. 6, as the ratio of glycerol was increased, the viscosity of the solution was increased, and the fluorescence intensity obtained by scanning at an excitation wavelength of 440nm was increased. As can be seen from FIG. 7, the fluorescence intensity at 628nm is plotted as ordinate and the solution viscosity as abscissa, and the linear relationship between them is found to be a good linear relationship in the range of viscosity 1-109 cP, the linear equation: y is 29.65x +711.47 (R)20.999). Thus, it was confirmed that the probe (I) can quantitatively detect the solution viscosity by the change in fluorescence intensity at 628 nm.
Example 4: fluorescence spectroscopy of the fluorescent probe (I) in solutions of different pH.
Accurately weighing a certain amount of the fluorescent probe (I), preparing a mother solution with the concentration of 10mM by using dimethyl sulfoxide, sucking 40 mu L of the mother solution by using a pipette gun, adding the mother solution into 4mL of PBS (pH is 3.5, 4, 4.5, 5, 5.5, 6, 7, 7.4, 8, 8.5, 9 and 10), shaking, uniformly mixing, carrying out ultrasonic treatment, adding the mixture into a cuvette, and testing by using a fluorescence spectrophotometer.
As shown in FIG. 8, the change of fluorescence intensity of the probe is small with the change of pH, which proves that the pH of the solution does not substantially affect the detection of viscosity by the probe.
Example 5: and (3) testing the anti-interference capability of the fluorescent probe (I).
Accurately weighing a certain amount of fluorescent probe (I), preparing a mother solution with the concentration of 10mM by using dimethyl sulfoxide, sucking 40 mu L of the mother solution by a pipette gun, and adding the mother solution into 4mL of PBS (1 to 20 are Gu respectively) containing different analytes2+、Ni2+、K+、Sr2+、Cd2+、Ba2+、Zn2+、Mg2+、SO3 2-、NO3 2-、I-、HS-、HSO3 -、F-、：Cys、GSH、Hcy、ClO-、H2O2、ONOO-Glycerol), shaking, mixing, adding into a cuvette after ultrasonic treatment, and testing with a fluorescence spectrophotometer.
As shown in fig. 9, the addition of other analytes had little effect on the fluorescence intensity of the probes compared to glycerol, demonstrating that the probes have good interference rejection.
Example 6: the probe (I) of the present invention is analyzed by viscosity imaging in human lung cancer cells.
A549 (human lung cancer cells) was inoculated into a petri dish, cultured in a carbon dioxide incubator, and after 24 hours, the cells were divided into two groups: an experimental group, adding nystatin purchased from a reagent company into a culture dish, incubating for half an hour at 37 ℃, washing twice by using a fresh culture medium, then adding a probe (I) for incubating for half an hour, washing by using PBS, and imaging under a laser confocal microscope; control, without additional treatment, was incubated with probe (I) directly for half an hour, washed with PBS and imaged under confocal laser microscopy. Fluorescence channel: the excitation wavelength is 488nm, and the emission and receiving wavelength range is 580-680 nm. A confocal image of the cell is shown in FIG. 10.
The results show that the fluorescence intensity of the A549 cells is increased after the incubation of the nystatin compared with the control group, and the probe (I) can qualitatively detect the change of the viscosity in the A549 cells.
The above-mentioned embodiments only express several embodiments of the present application, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the concept of the present application, which falls within the scope of protection of the present application. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (10)

1. The large Stokes displacement fluorescent probe for detecting viscosity is characterized in that the molecular formula of the probe is C26H24N2O, structural formula is shown as formula (I):
Figure FDA0003210904120000011
2. the method of claim 1, comprising:
mixing the compound (2) and the compound (3), adding acetonitrile and piperidine, and heating the mixture under the protection of nitrogen to obtain a reaction solution; carrying out spin drying, separation and purification on the reaction liquid to prepare the large Stokes shift fluorescent probe;
Figure FDA0003210904120000012
3. the method according to claim 2, wherein the molar ratio of the compound (2), the compound (3) and the piperidine is 1: 1-1.5: 0.1; the acetonitrile is used as a solvent.
4. The preparation method according to claim 2, wherein the mixture is heated under the protection of nitrogen under the following reaction conditions: reacting for 10-14 hours at 60-80 ℃.
5. Use of the large stokes shift fluorescent probe of claim 1 in the preparation of a viscosity detection reagent or viscosity detection kit.
6. The use of claim 5, wherein the viscosity detection reagent or viscosity detection kit is used to detect the viscosity in a cell or the viscosity in a solution.
7. The use of claim 6, wherein the cell is human lung cancer cell A549.
8. Use of the large stokes shift fluorescent probe of claim 1 in the preparation of a fluorescent imaging reagent or fluorescent imaging kit.
9. A method for quantitatively determining the viscosity of a solution, comprising:
the large Stokes shift fluorescent probe as claimed in claim 1 is added into the solution to be measured, after uniform mixing, ultrasonic treatment and standing, the fluorescence intensity of the solution is collected at the excitation wavelength of 440nm and the emission wavelength of 628nm, and the viscosity value of the solution to be measured is calculated according to a standard curve.
10. The method as claimed in claim 9, wherein the addition amount of the large stokes shift fluorescent probe in the solution to be tested is calculated by the ratio of the molar amount of the fluorescent probe to the viscosity in the solution: 0.005mM fluorescent probe: the viscosity is 1-109 cP.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114933555A (en) * 2022-06-24 2022-08-23 西北大学 Near-infrared fluorescent probe for detecting micromolecular mercaptan and preparation method thereof
CN116283663A (en) * 2021-12-20 2023-06-23 洛兮医疗科技(杭州)有限公司 Difunctional near infrared fluorescent probe for detecting monoamine oxidase A and viscosity as well as preparation and application thereof

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CN109897625A (en) * 2017-12-08 2019-06-18 南京理工大学 Selective enumeration method cysteine fluorescence probe and its synthetic method and application
CN110642857A (en) * 2019-09-20 2020-01-03 台州学院 Difunctional fluorescent probe for detecting viscosity and pH, and preparation and application thereof
CN113045596A (en) * 2021-03-24 2021-06-29 台州学院 Peroxynitroso anion and viscosity dual-response type fluorescent probe and preparation and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109897625A (en) * 2017-12-08 2019-06-18 南京理工大学 Selective enumeration method cysteine fluorescence probe and its synthetic method and application
CN110642857A (en) * 2019-09-20 2020-01-03 台州学院 Difunctional fluorescent probe for detecting viscosity and pH, and preparation and application thereof
CN113045596A (en) * 2021-03-24 2021-06-29 台州学院 Peroxynitroso anion and viscosity dual-response type fluorescent probe and preparation and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116283663A (en) * 2021-12-20 2023-06-23 洛兮医疗科技(杭州)有限公司 Difunctional near infrared fluorescent probe for detecting monoamine oxidase A and viscosity as well as preparation and application thereof
CN114933555A (en) * 2022-06-24 2022-08-23 西北大学 Near-infrared fluorescent probe for detecting micromolecular mercaptan and preparation method thereof

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