CN113388389B - Fluorescent carbon nanodot, preparation method and application thereof in cell nucleus targeted imaging - Google Patents
Fluorescent carbon nanodot, preparation method and application thereof in cell nucleus targeted imaging Download PDFInfo
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Abstract
The invention discloses a fluorescent carbon nanodot, a preparation method and application thereof in cell nucleus targeted imaging, wherein the fluorescent carbon nanodot is prepared by taking phenylenediamine and alkyl primary amine hydrochloride as raw materials. The fluorescent carbon nanodots prepared by taking phenylenediamine and alkyl primary amine hydrochloride as raw materials have the property of self-targeting cell nucleus, and the addition of the alkyl primary amine hydrochloride can promote microwave-assisted solid-phase reaction to generate the fluorescent carbon nanodots, so that the problems of time consumption of synthesis steps, consumption of a large amount of organic solvents, complex post-treatment and the like are solved.
Description
Technical Field
The invention belongs to the technical field of nano materials, and relates to a fluorescent carbon nanodot, a preparation method and application thereof in cell nucleus targeted imaging.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
The nucleus is the largest and most prominent organelle in the cell, is the central regulator of cell heredity and metabolism, and plays an important role in various physiological processes such as cell proliferation, differentiation and signal transduction. Research shows that the change of chromatin degradation, scaffold protein disintegration and the like in cell nucleus is not only an obvious sign of apoptosis, but also has close relation with the canceration state of tumor cells. The nucleus, a closed membranous cell, contains most of the DNA. DNA in the nucleus can regulate gene expression and direct protein synthesis. The degradation and mutation of DNA will cause various gene related diseases. Therefore, the cell nucleus targeted fluorescence imaging plays a crucial role in cell state assessment, disease diagnosis, therapeutic measure preparation and the like.
Until now, various commercial dyes such as DAPI (4, 6-diamidine-2-phenylindole) have been developed for nuclear targeting imaging, and although these dyes can be prepared to be localized to the nuclear micro-area, they have the disadvantages of complex synthetic steps, high cost, high toxicity, etc. Therefore, the development of a fluorescent material with good biocompatibility, simple synthesis and low cost for the targeted imaging of cell nucleus is urgently needed. Fluorescent carbon nanodots, as a new member of the carbon nanomaterial family, are receiving wide attention due to their excellent optical properties, ecological friendliness, sustainability, and biocompatibility. These properties make it an effective alternative to the use of traditional commercial dyes in the biomedical field. However, the inventor researches and discovers that most of the carbon nanodots reported at present still need to be used for nuclear localization by means of a biological agent for targeting a nucleus, the carbon nanodots cannot be independently and directly localized to the nucleus, and most of the fluorescent carbon nanodots only contaminate cytoplasm when cells are imaged. The fluorescent carbon nanodots which rarely enter the cell nucleus can dip and dye the cytoplasm at the same time, so that specific dyeing of the cell nucleus cannot be realized, and the carbon nanodots also have the defects of time-consuming synthesis steps, consumption of a large amount of organic solvents, complex post-treatment and the like.
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a fluorescent carbon nanodot, a preparation method and application thereof in cell nucleus targeted imaging.
In order to achieve the purpose, the technical scheme of the invention is as follows:
on the one hand, the fluorescent carbon nanodot is prepared by taking phenylenediamine and alkyl primary amine hydrochloride as raw materials.
The inventor knows in previous research that when different phenylenediamines are subjected to solvent heat treatment, fluorescent carbon nanodots with different fluorescent colors can be obtained, for example, the carbon quantum dots obtained by the solvent heat treatment of the phenylenediamines, the m-phenylenediamine and the o-phenylenediamine can respectively emit red fluorescence, blue fluorescence and green fluorescence, and in order to adjust the fluorescence color to be better suitable for the fluorescence imaging of cell nucleus, the invention firstly adopts primary alkyl amine as another raw material to adjust the fluorescence color of the phenylenediamines carbon nanodots.
However, experiments show that the carbon nanodots cannot be obtained by using phenylenediamine and alkyl primary amine as raw materials. Experiments show that the carbon nanodots can be obtained by replacing alkyl primary amine with alkyl primary amine hydrochloride, and the obtained carbon nanodots and the carbon nanodots obtained by single phenylenediamine have different fluorescent colors, for example, the carbon nanodots obtained by using m-phenylenediamine and alkyl primary amine hydrochloride as raw materials emit green fluorescence, and the carbon nanodots obtained by using o-phenylenediamine and alkyl primary amine hydrochloride as raw materials emit red fluorescence.
When the obtained carbon nanodots are subjected to cell imaging, the fluorescent carbon nanodots obtained by the method have the property of self-targeting cell nucleus.
The methods for preparing the carbon nanodots are generally hydrothermal methods or solvothermal methods, and the methods have the defects of time-consuming synthesis steps, consumption of a large amount of organic solvents, complex post-treatment and the like. In another aspect, a method for preparing a fluorescent carbon nanodot comprises the step of carrying out microwave-assisted solid phase reaction on phenylenediamine and alkyl primary amine hydrochloride serving as raw materials to obtain the fluorescent carbon nanodot.
The microwave-assisted solid-phase reaction can greatly reduce the reaction time, so the preparation method adopts the microwave-assisted solid-phase reaction for preparation. However, in the present invention, when the microwave-assisted solid phase reaction is performed using phenylenediamine as a raw material, the phenylenediamine cannot react to produce carbon nanodots regardless of the time adjustment. Experiments show that the fluorescent carbon nanodots can be obtained by performing microwave-assisted solid phase reaction on the phenylenediamine and the alkyl primary amine hydrochloride serving as raw materials. It is shown that the addition of primary alkylamine hydrochloride can promote the generation of carbon nanodots and thus reduce the reaction time of the carbon nanodots when the microwave-assisted solid phase reaction is performed. Meanwhile, the defects of large consumption of organic solvent, complex post-treatment and the like are overcome.
In the third aspect, the fluorescent carbon nanodots are applied to nuclear fluorescence imaging.
In a fourth aspect, the reagent for fluorescent staining of cell nuclei comprises a fluorescent dye and a buffer solution, wherein the fluorescent dye is the fluorescent carbon nanodots.
The invention has the beneficial effects that:
(1) the invention can directly synthesize two carbon nano materials with different luminescent colors by utilizing the reaction of different phenylenediamine and primary amine hydrochloride.
(2) The invention adopts microwave-assisted solid phase synthesis, and has the advantages of rapid process, no solvent consumption, low energy consumption and little pollution.
(3) The fluorescent carbon nano material synthesized by the invention can rapidly enter cells and is self-targeted to cell nucleus.
(4) The synthesis method of the self-targeting cell nucleus fluorescent carbon nanomaterial provided by the invention is simple and convenient to operate, low in cost, strong in practicability, free of participation of any solvent, free of dependence on a reaction solvent, and suitable for mass production and industrial popularization.
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 transmission electron microscope image of a fluorescent carbon nanomaterial prepared in example 1 of the present invention;
FIG. 2 is a transmission electron microscope image of the fluorescent carbon nanomaterial prepared in example 2 of the present invention;
FIG. 3 is an X-ray powder diffraction pattern of a fluorescent carbon nanomaterial prepared in example 3 of the present invention;
FIG. 4 is an X-ray powder diffraction pattern of a fluorescent carbon nanomaterial prepared in example 4 of the present invention;
FIG. 5 is a graph showing the excitation (left) and emission (right) spectra of the fluorescent carbon nanomaterial prepared in example 3 of the present invention;
FIG. 6 is a graph showing the excitation (left) and emission (right) spectra of the fluorescent carbon nanomaterial prepared in example 4 of the present invention;
FIG. 7 is a fluorescence image of the fluorescent carbon nanomaterial prepared in example 1 of the present invention as a nuclear targeting probe;
FIG. 8 is a fluorescence image of the fluorescent carbon nanomaterial prepared in example 2 of the present invention as a nuclear targeting probe.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. 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 invention 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 exemplary embodiments according to the invention. 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.
In view of the fact that the existing carbon nanodots cannot be independently and directly positioned to cell nuclei, the invention provides fluorescent carbon nanodots, a preparation method and application of the fluorescent carbon nanodots in cell nucleus targeted imaging.
The invention provides a fluorescent carbon nanodot, which is prepared by taking phenylenediamine and alkyl primary amine hydrochloride as raw materials.
The fluorescent carbon nanodots prepared by using phenylenediamine and alkyl primary amine hydrochloride as raw materials not only change the original fluorescent color of the carbon nanodots prepared from phenylenediamine, but also have the property of self-targeting cell nucleus.
The primary alkylamine hydrochloride has the formula RNH2HCl, R is an alkyl group, such as methyl, ethyl, propyl, butyl, etc. R is preferably C1-C5 alkyl.
In some examples of this embodiment, the mass ratio of the phenylenediamine to the primary alkylamine hydrochloride is 1: 0.02-2.
In one or more embodiments, the reaction mass ratio of the m-phenylenediamine to the primary amine hydrochloride is 1: 0.02-2,
the reaction mass ratio of the o-phenylenediamine to the primary amine hydrochloride is 1: 0.05-0.5.
In some examples of this embodiment, the fluorescent carbon nanodots have a particle size of 1 to 10 nm. The smaller particle size is easier to enter the cell.
The invention also provides a preparation method of the fluorescent carbon nanodot, which comprises the step of carrying out microwave-assisted solid-phase reaction on phenylenediamine and alkyl primary amine hydrochloride serving as raw materials to obtain the fluorescent carbon nanodot.
According to the invention, the generation of the fluorescent carbon nanodots in the microwave-assisted solid phase reaction is promoted by adding the alkyl primary amine hydrochloride, so that the reaction time of the carbon nanodots is greatly reduced. Meanwhile, the problems of large organic solvent consumption, complex post-treatment and the like are solved.
In some examples of this embodiment, the reaction time is 0.5 to 10 min.
In some examples of this embodiment, the microwave-assisted pyrolysis reaction is performed after the phenylenediamine and the primary alkylamine hydrochloride are mixed uniformly.
In one or more embodiments, the mixing method is milling.
In some examples of this embodiment, the microwave has a power of 600W to 800W.
The selection of the alkyl primary amine hydrochloride and the proportion of the alkyl primary amine hydrochloride and the phenylenediamine are consistent with the above.
In a third embodiment of the invention, an application of the fluorescent carbon nanodots in nuclear fluorescence imaging is provided.
In a fourth embodiment of the invention, a nuclear fluorescent staining reagent is provided, which comprises a fluorescent dye and a buffer solution, wherein the fluorescent dye is the fluorescent carbon nanodots.
In order to make the technical solutions of the present invention more clearly understood by those skilled in the art, the technical solutions of the present invention will be described in detail below with reference to specific embodiments.
Example 1
Weighing 0.1g of m-phenylenediamine and 0.02g of methylamine hydrochloride, placing the m-phenylenediamine and the methylamine hydrochloride into a mortar, fully grinding and uniformly mixing, transferring the mixture into a 50mL beaker, placing the beaker into a microwave oven with the power of 700W for solid phase reaction, and obtaining the green fluorescent carbon nanodot after 1 minute.
Example 2
Weighing 0.8g of o-phenylenediamine and 0.4g of ethylamine hydrochloride, placing the o-phenylenediamine and the ethylamine hydrochloride into a mortar, fully grinding and uniformly mixing the o-phenylenediamine and the ethylamine hydrochloride, transferring the mixture into a 100mL beaker, placing the beaker into a microwave oven with the power of 700W for solid phase reaction, and obtaining the carbon nanodot with red fluorescence after 3 minutes.
Example 3
Weighing 0.6g of m-phenylenediamine and 0.2g of propylamine hydrochloride, placing the m-phenylenediamine and the propylamine hydrochloride into a mortar, fully grinding and uniformly mixing, transferring the mixture into a 100mL beaker, placing the beaker into a microwave oven with the power of 700W for solid phase reaction, and obtaining the green fluorescent carbon nanodot after 5 minutes.
Example 4
Weighing 0.1g of o-phenylenediamine and 0.05g of butylamine hydrochloride, placing the o-phenylenediamine and the butylamine hydrochloride into a mortar, fully grinding and uniformly mixing the materials, transferring the mixture into a 50mL beaker, placing the beaker into a microwave oven with the power of 700W for solid phase reaction, and obtaining the red fluorescent carbon nano material after 7 minutes.
As shown in fig. 1, which is a transmission electron microscope characterization chart of the green fluorescent carbon nanomaterial prepared in example 1, the synthesized carbon nanomaterial has uniform size and is approximately spherical; as shown in fig. 2, which is a transmission electron microscope characterization chart of the red fluorescent carbon nanomaterial prepared in example 2, the synthesized carbon nanomaterial has good monodispersity; the particle size of the synthesized fluorescent carbon nano material is less than 10nm and is carbon nanodots, so that the fluorescent carbon nano material is easy to enter cells.
Fig. 3 is an X-ray powder diffraction pattern of the green fluorescent carbon nanodots prepared in example 3, indicating that the synthesized material is an amorphous carbon structure; as shown in fig. 4, the X-ray powder diffraction pattern of the red fluorescent carbon nanodots prepared in example 4 proves that the synthesized material also has an amorphous carbon structure.
As shown in fig. 5, the optimal excitation wavelength and emission wavelength of the green fluorescent carbon nanodots prepared in example 3 were 460nm and 520nm, respectively; as shown in fig. 6, the optimal excitation and emission wavelengths of the red fluorescent carbon nanodots prepared in example 4 were 530nm and 600nm, respectively.
The nuclear staining experiment was performed in the following procedure: first, Hela cells were seeded on cell slides in 12-well plates containing 100 U.mL-1Penicillin and streptomycin and 10% fetal bovine serum, then in 5% CO2The incubator was humidified and incubated at 37 ℃ for 48 hours. The medium was replaced with a buffer solution containing green and red carbon nanodots at pH 3.5, and cultured for 20 min. Before imaging, 1mL of NaH at pH 3.5 was used2PO4 -The complex-loaded cells were washed 3 times with citrate buffer solution. Images were taken by fluorescence microscopy. As a result, as shown in fig. 7, the green fluorescent carbon nanodots prepared in example 1 can rapidly enter cells and target to the cell nucleus, and the cell nucleus is stained to emit high-resolution green fluorescence; as shown in fig. 8, the red fluorescent carbon nanodots prepared in example 2 can rapidly enter cells and target to the nucleus, staining the nucleus to emit bright red fluorescence.
Example 5
0.1g of o-phenylenediamine is weighed and placed in a microwave oven with the power of 700W for solid-phase reaction, and the fluorescent carbon nanodots cannot be obtained within 0.3 minute of reaction. And the product is subjected to fluorescence detection, and no fluorescence is generated.
Example 6
0.4g of m-phenylenediamine and 0.2g of methylamine hydrochloride are added with 20mL of water and subjected to hydrothermal reaction at 180 ℃ for 12 hours to obtain the green fluorescent carbon nanodots. The carbon nanodots have the property of self-targeting the nucleus, but are less effective than example 1 (still a small fraction of the carbon nanodots are located in the nucleus).
Example 7
0.4g of m-phenylenediamine is added into 20mL of ethanol, and the solvothermal reaction is carried out for 12 hours at 180 ℃ to obtain the carbon nanodots with blue fluorescence. The carbon nanodots do not have the property of self-targeting to the nucleus.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. 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 (11)
1. A preparation method of a fluorescent carbon nanodot is characterized in that phenylenediamine and alkyl primary amine hydrochloride are used as raw materials, and microwave-assisted solid phase reaction is carried out to obtain the fluorescent carbon nanodot.
2. The method for producing a fluorescent carbon nanodot according to claim 1, wherein the mass ratio of phenylenediamine to alkyl primary amine hydrochloride is 1:0.02 to 2.
3. The method for producing a fluorescent carbon nanodot according to claim 1, wherein the reaction mass ratio of m-phenylenediamine to primary amine hydrochloride is 1:0.02 to 2, and the reaction mass ratio of o-phenylenediamine to primary amine hydrochloride is 1:0.05 to 0.5.
4. The method for preparing the fluorescent carbon nanodots according to claim 1, wherein the fluorescent carbon nanodots have a particle size of 1 to 10 nm.
5. The method for preparing fluorescent carbon nanodots according to claim 1, wherein the reaction time is 0.5 to 10 min.
6. The method for preparing a fluorescent carbon nanodot according to claim 1, wherein the microwave-assisted pyrolysis reaction is performed after the phenylenediamine and the alkyl primary amine hydrochloride are uniformly mixed.
7. The method of preparing a fluorescent carbon nanodot according to claim 6, wherein the mixing method is milling.
8. The method of claim 6, wherein the microwave power is 600-800W.
9. A fluorescent carbon nanodot prepared by the preparation method of claim 1.
10. Use of the fluorescent carbon nanodots of claim 9 in nuclear fluorescence imaging.
11. A nuclear fluorescent staining reagent comprising a fluorescent dye and a buffer solution, the fluorescent dye being the fluorescent carbon nanodots of claim 9.
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