CN111100184A - Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof - Google Patents
Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof Download PDFInfo
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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Abstract
The invention provides a fluorescent probe for detecting superoxide anion free radicals in peroxisomes and application thereof, and belongs to the technical field of detection and analysis. The invention designs a method for using caffeic acid as O2 ·‑The fluorescent probe for detecting superoxide anion free radicals, which takes small peptide (QSKL) as a target group of peroxisome, has the following structural formula:
the fluorescent probe is particularly suitable for detecting superoxide anions at the cellular structure level, particularly at the sub-cellular structure level (e.g., peroxisomes)The radical has good practical application value.
Description
Technical Field
The invention belongs to the technical field of detection and analysis, and particularly relates to a fluorescent probe for detecting superoxide anion free radicals in peroxisomes and application thereof.
Background
The information disclosed in this background of the invention is only for enhancement of understanding of the general background of the invention and is not necessarily to be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
Depression is a global mental disease with high morbidity, recurrence rate, mortality and disability rate, and seriously harms human health. Unfortunately, the current understanding of the pathophysiology of depression is still very poor. In order to effectively prevent and treat the depression, the occurrence and development process of the depression must be thoroughly understood. The two-photon fluorescence imaging technology has the advantages of high spatial resolution, small light damage to biological tissues, deeper tissue penetrating capacity and the like, and becomes an important imaging method for researching occurrence and development of biological events and diseases in cells and living bodies from the molecular level.
Peroxisomes, which are important organelles in cells, can produce Reactive Oxygen Species (ROS) and scavenge ROS, and play a crucial role in maintaining the redox balance in cells. Superoxide anion radical (O)2 ·-) Is the first ROS produced in the organism, and the content of the ROS directly represents the level of oxidative stress. Thus, O in peroxisomes was explored2 ·-The role in the development of depression is crucial to understanding the pathogenesis of depression. However, it is currently used for detecting O in peroxisomes2 ·-The tool (2) has not been reported.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a fluorescent probe for detecting peroxisome superoxide anion free radicals and application thereof. The invention designs a method for using caffeic acid as O2 ·-The fluorescent probe for detecting superoxide anion free radicals, which takes small peptide (QSKL) as a target group of peroxisome, is particularly suitable for cell structure level, particularly subcellular structureThe level (such as peroxisome) detects superoxide anion free radical, thus having good practical application value.
In order to achieve the technical purpose, the technical scheme adopted by the invention is as follows:
in a first aspect of the invention, a fluorescent probe is provided, which comprises caffeic acid and a small molecule peptide coupled with the caffeic acid.
The small molecule peptide is used as a positioning group for positioning peroxisome; preferably, the amino acid sequence of the small molecule peptide is selected from the group consisting of: comprises or consists of a sequence of QSKL (Gln-Ser-Lys-Leu); more preferably, the small molecule peptide amino acid sequence is QSKL.
Further, the structural formula of the fluorescent probe is as follows:
in a second aspect of the invention, there is provided the use of the above-described fluorescent probe for detecting superoxide anion radicals.
The application environment includes, but is not limited to, biological organs, tissues, cells, and subcellular structures.
Wherein the subcellular structure is a peroxisome.
In a third aspect of the present invention, there is provided a method for detecting superoxide anion radicals, the method comprising: and incubating the fluorescent probe and a sample to be detected together, and carrying out fluorescence imaging.
Wherein the incubation treatment conditions are as follows: the incubation temperature is 30-40 ℃, and the incubation time is 0.1-0.5 h.
The invention has the beneficial technical effects that:
the invention reports a fluorescent probe for detecting superoxide anion free radicals in a subcellular structure in a cell for the first time. The detection process does not need to add other chemical substances, has simple operation and small cytotoxicity and is beneficial to intracellular detection. Meanwhile, the fluorescent probe is simple to synthesize, sensitive in detection, high in speed and good in selectivity, and does not need to be incubated for a long time in the detection processAnd (5) breeding. The fluorescent probe of the invention realizes the imaging analysis of O in peroxisome in the brain of the tristimania mouse on the living body level2 ·-Thus, the method has good practical application value.
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 graph showing the optical properties of a fluorescent probe in example 1 of the present invention; wherein FIG. 1A shows the fluorescent probe in the presence of O2 ·-In the case of the sample, an absorption peak at about 370nm was observed; FIG. 1B shows fluorescent probes in the presence of O2 ·-Fluorescence intensity at 495nm under single photon 370nm excitation; FIG. 1C shows fluorescent probes in the presence of O2 ·-Fluorescence intensity at 495nm under two-photon 800nm excitation.
FIG. 2 is an image of a cell in example 1 of the present invention; wherein, FIG. 2A is an image of cells of a control group, which are incubated by adding probes into PC12 cells; FIG. 2B shows a stimulated group, in which PC12 cells were first stimulated with 2-Me to produce O2 ·-Adding a probe to incubate a cell imaging graph; FIG. 2C shows the clearance group, in which PC12 was first stimulated with 2-Me to generate O2 ·-Then adding a scavenger Tiron to remove O2 ·-Finally, adding a cell imaging graph after probe incubation; FIG. 2D is a graph showing the data output of the fluorescence intensity of FIGS. 2A, 2B, and 2C.
FIG. 3 is an image of a living body in embodiment 1 of the present invention; wherein, fig. 3A is a two-dimensional plan view of two-photon 3D imaging of normal mice after intraperitoneal injection of probes in a control group; FIG. 3B is a two-dimensional plan view of two-photon 3D imaging of depressed mice after intraperitoneal injection of a probe in an experimental group; FIG. 3C is a two-photon 3D imaging of FIG. 3A; FIG. 3D is a two-photon 3D imaging diagram of FIG. 3B; FIG. 3E is a graph of fluorescence intensity data output of FIGS. 3A and 3B.
FIG. 4 is a mass spectrum of the fluorescent probe in example 1 of the present invention.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. 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.
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 example embodiments according to the present application. 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.
The present invention will now be further described with reference to specific examples, which are provided for the purpose of illustration only and are not intended to be limiting. If the experimental conditions not specified in the examples are specified, the conditions are generally as usual or as recommended by the reagents company; reagents, consumables and the like used in the following examples are commercially available unless otherwise specified.
As previously mentioned, it is currently used for the detection of O in peroxisomes2 ·-The tool (2) has not been reported.
In view of this, the present invention provides a fluorescent probe for detecting superoxide anion radicals and applications thereof. The invention designs a method for using caffeic acid as O2 ·-The fluorescent probe for detecting superoxide anion free radicals, which takes small peptide (QSKL) as a target group of peroxisome, is particularly suitable for detecting superoxide anion free radicals at the cellular structure level, particularly the subcellular structure level (such as organelles).
In one exemplary embodiment of the present invention, a fluorescent probe is provided, which includes caffeic acid, and a small molecule peptide coupled to caffeic acid.
In yet another embodiment of the invention, the small molecule peptide is used as a targeting group for localization of peroxisomes; preferably, the amino acid sequence of the small molecule peptide is selected from the group consisting of: comprises or consists of a sequence of QSKL (Gln-Ser-Lys-Leu); more preferably, the small molecule peptide amino acid sequence is QSKL.
In another embodiment of the present invention, the structural formula of the fluorescent probe is as follows:
the positioning and identifying mechanism of the fluorescent probe is as follows: SKL (localization signal peptide PTS1) is a localization group of peroxisome, can specifically act with PEX protein on a peroxisome membrane, and enters the peroxisome interior through a transmembrane transport mode, thereby realizing the localization function.
When with O2 ·-During reaction, the catechol structure with caffeic acid residue as electron donor is changed into electron withdrawing catechol, and the electron distribution of the probe is changed to result in fluorescence change, so as to specifically detect O in peroxisome2 ·-The level of (c) varies.
It should be noted that, the sequence of the peroxisome localization signal peptide PTS1 is selected and obtained through research, caffeic acid is used as a fluorescence recognition group, and the caffeic acid is easily interfered by small molecular peptides of the localization group, so that the localization function of the caffeic acid on peroxisome is met when the localization group is selected, and the interference on the fluorescence recognition group is avoided, and therefore QSKL is selected as the localization group.
In another embodiment of the present invention, the fluorescent probe is used for detecting superoxide anion free radicals.
In yet another embodiment of the present invention, the application environment includes, but is not limited to, biological organs, tissues, cells and subcellular structures.
In yet another embodiment of the invention, the subcellular structure is a peroxisome.
In yet another embodiment of the present invention, there is provided a method for detecting superoxide anion radicals, the method comprising: and incubating the fluorescent probe and a sample to be detected together, and carrying out fluorescence imaging.
Wherein the incubation treatment conditions are as follows: the incubation temperature is 30-40 ℃, and the incubation time is 0.1-0.5 h.
The invention is further illustrated by the following examples, which are not to be construed as limiting the invention thereto. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The following examples are test methods in which specific conditions are indicated, and are generally carried out under conventional conditions. It should be noted that the fluorescent probe in this example was synthesized and provided by bio-engineering (shanghai) corporation, and its mass spectrum is shown in fig. 4.
Example 1
A fluorescent probe having the structure:
effect verification:
optical properties of embodiments of the present invention. Adding O2 ·-Thereafter, the probe (TCP) showed an absorption peak at about 370 nm. (FIG. 1A). As shown in FIG. 1B, under the excitation of a single photon at 370nm, the fluorescence intensity of TCP at 495nm is weak, and the fluorescence intensity of TCP is equal to that of 20 μ MO2 ·-After incubation together, the fluorescence intensity of the probe at 495nm was significantly increased, which was 4 times the initial fluorescence intensity. As shown in FIG. 1C, the fluorescence intensity of TCP at 495nm was enhanced by more than 8 times under two-photon 800nm excitation.
Experiments of embodiments of the invention in cells. We first used 0.1. mu.g/mL 2-Me (to cause oxidative stress in cells to produce O)2 ·-) PC12 cells were incubated for 15min, followed by addition of TCP (20. mu.M) followed by incubation for 30min, followed by washing off the extracellular residual probe with PBS and fluorescence imaging. We observed a three-fold increase in blue fluorescence intensity in the experimental group stimulated with 2-Me compared to the control group. To verify that the change in blue fluorescence signal was indeed due to O2 ·-Concentration of (2)Caused by the change, we used again the specific scavenger Tiron (scavenging O)2 ·-) The cells are treated and imaged after 30min, and the blue fluorescence intensity of the cells is obviously reduced. The above experimental results demonstrate that intracellular O can be observed by using the change in fluorescence intensity of TCP2 ·-The concentration of (c) was varied (as shown in fig. 2).
Experiments of the embodiments of the present invention in vivo. The normal mice and the depressed mice are injected with TCP (200 mu M) by intraperitoneal injection, and the brains of the mice are imaged by a two-photon microscope after 30 min. We found that the fluorescence intensity of the model group is obviously enhanced compared with that of the normal group, which indicates that the brain of the mouse with depression has O2 ·-The content was significantly increased (as shown in fig. 3). Through the experiments, the intracerebral O of the depressed mice is analyzed by fluorescence imaging for the first time2 ·-The level is obviously higher than that of normal mice. This result provides direct evidence for a positive correlation between oxidative stress and the extent of depression.
The invention is not the best known technology.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (10)
1. A fluorescent probe, which is characterized by comprising caffeic acid and a small molecule peptide coupled with the caffeic acid;
the small molecule peptide is used for positioning peroxisome.
2. The fluorescent probe of claim 1, wherein the amino acid sequence of the small molecule peptide is selected from the group consisting of: comprising or consisting of a sequence of QSKL.
3. The fluorescent probe of claim 1, wherein the fluorescent probe has the following structural formula:
4. use of the fluorescent probe according to any one of claims 1 to 3 for detecting superoxide anion radicals.
5. The use of claim 4, wherein the application environment includes, but is not limited to, biological individuals, organs, tissues, cells, and subcellular structures.
6. The use of claim 7, wherein the subcellular structure is peroxisome.
7. A method of detecting superoxide anion radicals, the method comprising: incubating the fluorescent probe according to any one of claims 1 to 3 with a sample to be tested for fluorescence imaging.
8. The method of claim 7, wherein the test sample includes, but is not limited to, biological individuals, organs, tissues, cells, and subcellular structures.
9. The method of claim 8, wherein the subcellular structure is a peroxisome.
10. The method of claim 7, wherein the incubation conditions are: the incubation temperature is 30-40 ℃, and the incubation time is 0.1-0.5 h.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114456079A (en) * | 2021-12-23 | 2022-05-10 | 山东师范大学 | Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator |
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| CN114456079A (en) * | 2021-12-23 | 2022-05-10 | 山东师范大学 | Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator |
| CN114456079B (en) * | 2021-12-23 | 2023-06-23 | 山东师范大学 | Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator |
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